Annapolis Single Family Properties for Sale

Enjoy this large scenic lot w/ fully finished rancher & oversized 2 car garage just outside of downtown Annapolis. Open floor plan, cathedral ceilings, hardwood floors, skylights & more. Bulkheaded waterfront w/ 4 deep water slips. Main floor living, plus a walk out lower level. You will not want to miss this property!! It is truly one of a kind! Property needs updating. Call agent for details. Do not enter property without an appointment.

314 Kingsberry Dr, Annapolis

Listing courtesy of RE/MAX One. Contact:

$3,495,000

5 Beds ⋅ 7 Baths

Located in the coveted Wardour community, this stately home combines timeless architecture with an enviable walkable location near West Annapolis’ shops and restaurants and just minutes from downtown. With stunning curb appeal, spacious 0.55 acre lot, expansive front yard and water views from nearly every room in the home, this property offers a rare combination of privacy and community, where every day feels like a retreat yet conveniences are just minutes away. The main level welcomes with a gracious foyer flanked by formal living and dining rooms, highlighted by custom millwork, crown molding, wainscoting, and hardwood floors. The formal living room features a classic gas fireplace, while the private office with built-ins and the inviting family room with a coffered ceiling provide versatile spaces for work and relaxation. The gourmet kitchen impresses with high-end appliances, a large center island, casual dining area overlooking the backyard, and wet bar adjoining the dining room. A well-designed mudroom off the two-car garage and side entry enhances everyday function. Upstairs, three spacious ensuite bedrooms complement the luxurious primary suite, which offers a serene sitting room with gas fireplace, private balcony, and spa-like bath. The top floor is a flexible open space with full bath, perfect as an office, playroom, studio, or lounge. The lower level is an entertainer’s retreat with a full bar, open gathering space anchored by a wood-burning fireplace, and a room prepped to become a wine cellar. A full bath and additional bedroom complete this versatile level. Conveniently located to access Downtown Annapolis, head over the Bay Bridge to the Eastern shore or jump on Rt. 50 to get back to Washington, DC and just a few short blocks to West Annapolis' charming commercial district's restaurants & shops. Welcome Home!

219 Wardour Dr, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact:

$1,599,000

A Builder’s Personal Residence | A Signature Annapolis Home A rare opportunity to own the personal residence of a builder and an interior designer, whose expertise and craftsmanship are reflected throughout their exceptional Annapolis home. 3124 Starboard Drive represents their vision of quality, functionality, and enduring design—where no detail was overlooked and every improvement was thoughtfully executed. Known as one of the neighborhood’s exceptional residences, this home offers a level of craftsmanship and attention to detail that is difficult to replicate. From the quality of construction and materials to the thoughtful design choices, the property reflects the discerning standards of a professional who builds and renovates homes for a living. This extraordinary residential real estate transformation is the creation of Mac O’Brien, the owner of Great Eastern Contracting, and his wife Becca O’Brien from Intuitive Design. Together they joined forces and underwent a complete, down-to-the-studs renovation and expansion. They purchased this home in 2015 and over the course of time they turned a 2,000 square foot home into an over 3,700 square feet of luxurious, modern turnkey showpiece with no detail overlooked. This five-bedroom, four-bathroom residence, has an open and elegant floor plan flooded with natural light. The chef kitchen has a stunning 8.9’ x 6.9’ quartz Island countertop offering exceptional workspace and seating for five with striking oversized lantern-style pendant lamps. The Owner’s Suite Spa-inspired primary bath has a custom white double-vanity, luxurious marble countertops, polished brass fixtures, oversized mirrors, elegant glass pendant lighting and heated floors. The expansive walk-in shower is beautifully appointed in veined marble tile with a frameless glass enclosure, multiple shower fixtures and built-in niches, creating a sophisticated, resort-like retreat. The living and family rooms have gas fireplaces and built ins. In addition, the home features a recreation room, fully fenced backyard, a double garage converted into a conditioned and finished Golf simulator room, shed and golf-cart garage. Mechanical systems include a full-house back-up generator, dual zone HVAC systems, tankless water heater, RO water filtration in kitchen and below counter Scotsman Gourmet Ice Maker and water treatment with dual storage tanks, salinator, chlorinator, sediment filter and UV light. This residence was meticulously rebuilt in 2021 - walls, ceilings, floors, fixtures, electrical, and plumbing systems—all removed and replaced with high-end finishes and craftsmanship throughout. The result is a striking blend of contemporary comfort and timeless design. Located in the sought-after waterfront community of Anchorage, this distinctive residence combines sophisticated living with the relaxed character of an established Annapolis neighborhood, offering access to the community’s marina, pool, boat ramp and waterfront amenities.

3124 Starboard Dr, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

$535,000

NEW ROOF- 50 year shingle! Welcome to this spacious Colonial in the sought after water privileged community of Cape St. Claire. Step inside to a bright and inviting main level filled with natural light. The spacious living room opens to the updated kitchen featuring a new island with seating for three, new quartz countertops, freshly painted cabinetry, and a cozy breakfast nook overlooking the rear yard. A dining room addition provides plenty of space for gathering and entertaining with direct access to the rear deck and yard. A full bath on this level adds extra convenience. Upstairs, you will find three bedrooms and two full baths. The primary suite features vaulted ceilings, a walk in closet, and a private ensuite bath complete with a soaking tub and separate stall shower. Outside, the property has been freshly landscaped with a new parking pad and fresh grass seed throughout. The rear yard offers plenty of space to enjoy the outdoors, along with a large shed for additional storage. Cape St. Claire offers a sought after waterfront lifestyle just minutes from Annapolis. This established community along the Chesapeake Bay features community several beaches, parks, playgrounds, three marinas, boat ramps, and opportunities for boating, kayaking, fishing, and enjoying life on the water. Known for its strong sense of community, Cape St. Claire hosts neighborhood events throughout the year and offers convenient access to local shopping, dining, schools, and major commuter routes. It is a wonderful setting for buyers looking to enjoy the relaxed Chesapeake Bay lifestyle while remaining close to Annapolis and everything Anne Arundel County has to offer.

1161 Green Holly Dr, Annapolis

Listing courtesy of Cummings & Co. Realtors. Contact:

$1,275,000

6 Beds ⋅ 6 Baths

$25,000 towards closing for a contract by 10/15. New Construction - Under Roof but still time to pick some finishes! Built by Whitehall Building & Company, this exceptional new home offers luxury finishes, thoughtful design, and quality craftsmanship in one of Annapolis’s most sought-after locations. Tucked away like a private hidden gem, this home places you just a short stroll from the best of Eastport and Downtown Annapolis. Enjoy the waterfront, acclaimed dining, charming boutiques, historic streets, marinas, and the vibrant energy that make Annapolis such a special place to live. With both Eastport and Downtown right outside your door, this is a rare opportunity to experience brand-new luxury in a truly walkable Annapolis location. Visit Whitehall Building & Company for additional information and project details.

15 Elliott Rd, Annapolis

Listing courtesy of EXP Realty, LLC. Contact:

$750,000

This immaculate 3 bedroom, ranch-style residence built in 1995 boasts 1,795 sq. ft. of luxurious living space on the main level + a finished basement. Step inside to find an open floor plan adorned with crown moldings and gleaming wood floors creating an inviting atmosphere perfect for entertaining. The gourmet kitchen, complete with an island and table space, is a culinary enthusiast's dream. Host friends and family for Thanksgiving where you can serve large parties in your formal dining room. The main living area is huge, with high ceilings, built-in shelves and a cozy fireplace. Enjoy the private backyard from the enclosed brick patio room. The fully finished, walk out basement gives you even more space for relaxation or hobbies. Heritage Harbour is a 55+ community that is located close to shopping, AAMC, historic Annapolis and major commuter routes ad offers endless amenities, activities and groups to keep you busy having fun, making friends and staying active. Embrace the exclusive amenities that define this community, including an art studio, fitness center, and multiple pools-both indoor and outdoor. Engage in friendly competition on the pickleball courts or enjoy leisurely strolls along the scenic jog/walk paths. With private access to the South River, indulge in water activities like canoeing or kayaking just a mile away. The meticulously maintained grounds and community features, including a clubhouse and library, foster a sense of belonging and camaraderie. Experience the perfect blend of luxury and leisure in this exceptional property, where every day feels like a retreat.

2548 Mission Hills Ct, Annapolis

Listing courtesy of Next Step Realty, LLC.. Contact:

$869,000

Enjoy the convenience and charm of Eastport living at 827 Bay Ridge, just a short walk to local restaurants, shops, marinas, parks, and downtown Annapolis. This updated and well-maintained 3-bedroom, 3-full-bath home offers comfortable, flexible living space. The main level features two bedrooms and two full baths, inviting living areas, hardwood floors, and an updated kitchen with white cabinetry, granite countertops, and stainless steel appliances. Just off the living and dining areas, the screened porch overlooks the private backyard, creating the perfect spot to relax or entertain. The lower level provides additional living space with a third bedroom and full bath, ideal for guests, a private retreat, or a home office. Outdoor features include a welcoming front porch, rear patio, private backyard, and a driveway conveniently located behind the home, along with a storage shed. Whether you’re looking for a full-time residence or a weekend getaway, this turnkey home has everything that makes coastal living so desirable!

827 Bay Ridge Ave, Annapolis

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$725,000

This spacious split-level home set on over a third of an acre features three main-floor bedrooms, two full baths (one of which is ensuite to the primary bedroom), and hardwood flooring. The vaulted living/dining room opens to a big deck overlooking a fully-fenced back yard. Downstairs, the fourth bedroom can be used as a TV room, office, or home gym. The lower-level includes a spacious family room with wood-burning fireplace, half bath, bonus room, laundry room, and plenty of storage space. The family room opens to the back yard. Numerous property improvements include a newer HVAC (2024), kitchen appliances (2022), replacement windows and sliding doors, and fresh paint throughout. The roof and gutters are less than five years old. Admiral Heights is a popular water-privileged community close to the Navy Marine Corps Stadium and just a mile and a half from downtown Annapolis. The neighborhood consists of more than 600 homes and features community amenities including a pool, a swim club, docks, parks, and kayak/canoe storage on Weems Creek. NOTE: Home is empty - many photos show virtual staging. Also, seller conducted a thorough home inspection in September 2026; a copy of this report is available upon request.

424 Halsey Rd, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact:

$550,000

5 Beds ⋅ 2 Baths

Welcome home to Cape St. Claire! Offering plenty of space inside and out, this beautifully updated rancher features a fully finished basement, five bedrooms, two full baths, and an open-concept layout designed for comfortable living. The main level showcases laminate wood floors, a gorgeous kitchen with granite counters, 42-inch cabinets and recessed lighting, plus three bedrooms and a full bath with convenient dual entry to the primary bedroom. Downstairs, you’ll find a large family room, two additional bedrooms, another full bath, laundry room, abundant storage, and walk-out access to the yard with a new awning. Whether you're relaxing on the front porch, grilling on the rear deck, or gathering around a fire pit in the spacious side yard, this home is ready to be enjoyed! Roof was replaced in 2021*********Cape St Claire amenities include, beaches, fishing/crabbing pier, boat ramp, playgrounds, marina, & more. Broadneck School District. Close to shops and restaurants. Mins from Downtown Annapolis, and easy access for commuter routes to Washington, Baltimore, and close to FtMeade. Great location, minutes from downtown Annapolis, and good commuter location with quick access to Rt 50 & I-97 close to Washington or Baltimore***BE SURE TO CHECK OUT THE VIRTUAL FLOOR PLAN TOUR

1230 Hilltop Dr, Annapolis

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$574,990

Imagine starting your morning with coffee in a sun-filled room, looking out over a peaceful backyard framed by trees. Later, you could launch a kayak, head to the community beach, take a walk through Quiet Waters Park, or be in downtown Annapolis in minutes. This is the lifestyle that makes Hillsmere Shores so special. Set near the Chesapeake Bay and the mouth of the South River, this updated 3-bedroom, 2.5-bath home blends comfort, character, and flexibility in one of Annapolis’s most loved waterfront communities. Inside, a thoughtful renovation created spaces that feel open, warm, and easy to enjoy. The expanded kitchen features a center island, eat-in area, custom tile backsplash, solid wood cabinetry, and plenty of room to gather. The primary suite was also expanded and now offers a sitting area, large walk-in closet, brand-new carpeting, and a beautifully renovated bath. But the room you may never want to leave is the four-season sunroom. Fresh paint, new luxury vinyl plank flooring, and views of the fenced backyard make it the perfect place to relax in every season.The finished lower level gives you even more room to spread out. Use it as a recreation room, office, gym, creative space, or potential fourth bedroom. A classic brick fireplace with an insert creates the perfect backdrop for cozy evenings, and a half bath adds extra convenience. Outside, the backyard offers privacy, trees, and room to enjoy the outdoors. And then there’s Hillsmere Shores itself: a private marina, boat ramps, kayak and canoe launch, community beach, swimming pool, playgrounds, picnic areas, and recreation spaces—all just minutes from downtown Annapolis, Key School, and Quiet Waters Park. This isn’t just Annapolis living. This is Chesapeake Bay living at its best.

416 Walnut Dr, Annapolis

Listing courtesy of Keller Williams Flagship. Contact:

$2,199,000

Welcome to one of Annapolis’ most sought-after water-access communities, where timeless character meets extensive, thoughtful improvements. Since 2022, the sellers have invested extensively in enhancing the home's living spaces, major systems, and outdoor setting, while carefully preserving its original character. Major improvements include a beautifully reimagined kitchen, renovated primary and secondary baths, updated bedrooms, custom millwork and library built-ins, upgraded electrical and lighting, and extensive interior and exterior painting. Additional enhancements include updates to the home's heating systems, whole-house water filtration, and a thoughtfully redesigned family room with an inviting stove and improved flow throughout the main level. Outside, the transformation is equally impressive. Extensive professional landscaping and hardscaping have created a private, beautifully designed setting featuring a stone patio, firepit, landscape lighting, lush gardens, and multiple spaces for outdoor entertaining. A garage provides coveted off-street parking, with ample street parking available for guests. The list of improvements goes well beyond what can be captured here. This is a home that truly deserves to be experienced in person to appreciate the care, attention, and investment that have gone into it. Living in Wardour is about much more than the home. Residents enjoy access to private community beaches, kayak storage, wooded trails, and waterfront pathways—all just minutes from the heart of Annapolis. The neighborhood offers an exceptional combination of convenience and lifestyle, with a Blue Ribbon elementary school, coffee shop, ice cream shop, brewery, café, grocery store, upscale dining, and numerous neighborhood restaurants close by. Downtown Annapolis and Navy-Marine Corps Memorial Stadium are both within walking distance, while nearby Route 50 provides easy access to Washington, D.C., Baltimore, and the Eastern Shore. Beautifully updated, meticulously landscaped, and ideally located, this is a wonderful opportunity to enjoy the best of the Annapolis lifestyle in one of its most desirable communities.

102 Melvin Ave, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

$565,000

Tucked away down a tree-lined driveway on over half an acre, 1365 Moyer Road offers a rare combination of privacy, thoughtful updates, and convenient access to everything Annapolis has to offer. Located just off Arundel on the Bay Road, this beautifully renovated home is minutes from downtown Annapolis, Quiet Waters Park, local marinas, and the Chesapeake Bay. Inside, the home feels bright and refreshed with luxury vinyl plank flooring, fresh paint, and an updated kitchen featuring stylish cabinetry, countertops, and sink. The upper level includes three spacious bedrooms and two updated full baths, including a private primary suite with its own bath and direct access to the rear deck. The lower level provides additional living space with a fireplace, third full bath, and flexible bonus room ideal for a home office, gym, playroom, or guest space. Outside, enjoy a newer deck overlooking the fully fenced 0.65-acre backyard with plenty of room for entertaining, pets, recreation, or boat storage. Additional 2026 improvements include a new water pressure tank, serviced well, updated doors, and numerous updates throughout the home. Private, move-in ready, and ideally located near the water and downtown Annapolis, 1365 Moyer Road is ready for its next owner.

1365 Moyer Rd, Annapolis

Listing courtesy of Cummings & Co. Realtors. Contact:

$975,000

Welcome to 98 Monticello Avenue, a charming Murray Hill residence that captures the character and ease of the Annapolis lifestyle. From the moment you step inside, a welcoming entryway sets the tone for a home filled with warmth, natural light and thoughtful spaces throughout. The main level offers a comfortable living room centered around a beautiful fireplace, creating an inviting place to gather and unwind. The adjacent kitchen is bright and beautifully appointed with hardwood flooring, a cooktop and a cozy breakfast nook. A convenient half bath completes the main level, while a spacious deck extends the living space outdoors and overlooks the fully fenced backyard- an ideal setting for morning coffee, entertaining, or enjoying time outdoors. Upstairs, three generously sized bedrooms share a full bath, offering comfortable accommodations for family and guests. Continue to the upper level to discover additional flexible space that can easily adapt to your lifestyle—whether used as a home office, playroom, creative space or additional storage. The lower level adds even more versatility with a full bathroom, laundry area and abundant storage, providing valuable functionality rarely found in a home of this character. Set in the highly desirable Murray Hill neighborhood, this water-oriented location offers easy access to Spa Creek and the waterfront lifestyle that makes Annapolis so special, while remaining just moments from downtown. Enjoy convenient access to the Naval Academy, local restaurants, shops, parks and the many experiences that define the Annapolis lifestyle. A home with timeless charm, flexible living spaces, outdoor living and an exceptional location, all within one of Annapolis' most beloved neighborhoods. PHOTO DISCLOSURE: Photo #1 has been AI-enhanced for marketing purposes. The fireplace flames were digitally added and are not intended to represent or warrant the condition, functionality, or operability of the fireplace.

98 Monticello Ave, Annapolis

Listing courtesy of Engel & Volkers Annapolis. Contact:

$525,000

5 Beds ⋅ 2 Baths

$10,000.00 seller closing help Like-new look, new windows, new appliances, new HVAC system, new Central unit, new cabinets, fully updated from top to bottom. Nestled in the serene community of Primrose Acres, this exquisite split foyer home offers a perfect blend of modern luxury and timeless charm. With a major renovation slated for 2026, this property is poised to become a stunning showcase of contemporary living, while still retaining its classic appeal. As you approach the home, you'll be greeted by a beautifully landscaped exterior that exudes warmth and sophistication. The fiberglass siding not only enhances the aesthetic appeal but also ensures durability and energy efficiency. The inviting entrance leads you into a spacious layout, where natural light pours in through energy-efficient bay and bow windows, creating a bright and airy atmosphere throughout. The heart of this home is its expansive outdoor space, featuring a personal in-ground pool that promises endless summer enjoyment. The level lot, spanning 0.15 acres, provides ample room for outdoor gatherings, gardening, or simply basking in the sun. Inside, the home boasts five generously sized bedrooms and two full bathrooms, offering plenty of space for relaxation and privacy. The hardwood and tile flooring throughout adds a touch of elegance, while the basement, complete with a walkout entrance, presents an opportunity for additional living space or a creative retreat. The property is equipped with modern green energy-efficient features, including an advanced HVAC system and energy-efficient lighting, ensuring comfort while being mindful of the environment. The thoughtful design extends to the laundry area, conveniently located in the basement with hookups for both a washer and dryer. Located just minutes from major transportation routes, including commuter rail stations and bus stops, this home offers easy access to the surrounding area, making it ideal for those who appreciate both tranquility and convenience. This residence is more than just a house; it's a lifestyle. With its luxurious features, prime location, and the promise of a stunning renovation, this property invites you to envision a life of comfort and elegance. Experience the best of Primrose Acres and make this exceptional home your own. THE POOL MOTOR IS NOT FUNCTIONING.

391 Hilltop Ln, Annapolis

Listing courtesy of Deausen Realty. Contact:

$799,900

4 Beds ⋅ 2 Baths

Why pay for someone else's vision when you can create your own? Discover the possibilities at 356 Severn Road in the sought-after private, gated waterfront community of Epping Forest on the Severn River! Offered at $799,900, with a contractor's renovation estimate of approximately $249,000, imagine creating your own beautifully updated retreat for a combined estimated purchase and renovation investment of approximately $1.05 million! Be sure to explore the VIRTUAL RENOVATION CONCEPT DESIGN photos displayed alongside the current-condition photos! These renderings showcase what this home COULD become with thoughtful renovations, creative vision, and investment. A contractor's renovation estimate and additional renovation concepts are available for review. Situated on a rare, relatively level 0.24-acre lot just steps from the waterfront clubhouse, marina, tennis courts, and community amenities, this property offers an exceptional combination of location, space, and potential. Featuring approximately 2,784 finished above-grade square feet, 4 bedrooms, 2 full baths, flexible main-level living spaces, and a 2-car garage, there's plenty of room to reimagine and personalize. Originally built as a cottage in 1930 and expanded in the 1980s, the home retains charming original features, including a stone propane gas fireplace with built-ins. An oversized eat-in kitchen, spacious dining room with vaulted ceiling and exposed beam, versatile family room, and additional flex space provide exciting renovation possibilities. Upstairs, skylights bring in natural light, and the primary bedroom opens to a deck with peek-a-boo Severn River views. New sliding doors were installed in 2024. Additional features include dual-zone HVAC, privately operated community water system, BAT septic system, and a greenhouse and pond that convey AS-IS. Location. Lifestyle. Exciting After-Repair Value (ARV) Potential! With beautifully renovated homes throughout Epping Forest providing inspiration, this property presents an opportunity to transform an existing home, personalize the finishes, and potentially build equity. Buyers are encouraged to evaluate the projected investment and after-repair value based on comparable sales and their renovation plans. And then there's the Epping Forest lifestyle! Enjoy the community beach, waterfront clubhouse with restaurant and bar, an improved marina currently under construction, tennis courts, walking trails, boat ramp, community chapel, and year-round social activities, including the beloved Fourth of July fireworks celebration. Bring your imagination, explore the renovation concepts, and discover what 356 Severn Road COULD become! An opportunity to create your own renovated home in one of Annapolis' most distinctive waterfront communities. Virtual renovation renderings are conceptual only and depict improvements not completed. Contractor's estimate is subject to scope, conditions, and actual costs. Renovation feasibility and ARV are not guaranteed. Property offered AS-IS. Epping Forest is a private, gated waterfront community and Special Tax District (annual $1,760.43) with binding Rules and Regulations. Schedule your tour today!

356 Severn Rd, Annapolis

Listing courtesy of EXP Realty, LLC. Contact:

$489,909

Welcome to this beautifully renovated 3-bedroom, 2-full-bath single-family home in the desirable Arundel on the Bay community. This move-in-ready home features a spacious kitchen with quartz countertops, stainless steel appliances, upgraded cabinetry, and coffered ceilings complemented by abundant recessed lighting. The property sits on a 7,300-square-foot lot with a nice-sized yard and a Trex deck, perfect for outdoor entertaining and relaxing. The home is conveniently located just steps from a large community playground, making it especially convenient for families. Enjoy the benefits of this water-privileged community, including access to the beach and boat slips. The HOA is voluntary, providing flexibility while still offering access to community amenities.

3458 Newport Ave, Annapolis

Listing courtesy of RE/MAX Galaxy. Contact:

$2,395,000

5 Beds ⋅ 5 Baths

NEW PRICE MARKET ALIGNMENT - A FRESH OPPORTUNITY IN MURRAY HILL! A rare opportunity in the heart of Murray Hill! Welcome to 8 Brooke Avenue, a stunning 2015 Traynor Brothers-built Craftsman offering nearly 5,000 square feet of beautifully finished living space just steps from Downtown Annapolis. Combining timeless architecture, exceptional craftsmanship, and the space and amenities today's luxury buyer desires, this extraordinary home features 5 bedrooms, 5 full baths, a main-level office/optional 6th bedroom, three finished levels, and an oversized 2-car garage all on a flat 0.18-acre lot. The attention to detail begins at the curb with HardiePlank siding, AZEK trim, cultured stone, tapered Arts & Crafts columns, hand-built wood brackets, a Brazilian cherry front porch, and brick-paver driveway and walkway. Step inside to a light-filled, open floor plan showcasing white oak flooring, plantation shutters, custom hardwood trim and moldings, wainscoting, coffered ceilings, and a striking gas fireplace with custom architectural mantel. Designed for entertaining, the gourmet kitchen centers around a generous granite island and features high-end stainless appliances, oversized subway tile, and a Bertazzoni 36" six-burner gas range with wok burner. A walk-in butler's pantry with custom hardwood shelving and barn-style door provides exceptional storage, while the spacious mudroom with built-in cubbies makes everyday living effortless. Just beyond, a screened porch creates the perfect setting for morning coffee, dinner with friends, or relaxing outdoors. Upstairs, the luxurious primary suite feels like a private retreat with a vaulted ceiling, two generous walk-in closets with custom built-ins, and a spa-inspired bath featuring a soaking tub, double vanity, and oversized three-head shower. Three additional bedrooms and two additional full baths complete the sleeping quarters. Even the laundry room has been thoughtfully designed—a large, updated, light-filled space with higher ceilings, generous storage, and a utility sink, making everyday functionality feel anything but ordinary. The finished walk-out lower level adds another dimension to the home with a spacious recreation area, additional bedroom, full bath, flex/play space, abundant storage, and direct access to a shaded brick-paver patio. An additional outdoor firepit gathering area creates yet another inviting place to entertain, unwind, and enjoy evenings with family and friends. And then there is the location. Walk to Downtown Annapolis, the U.S. Naval Academy, waterfront, restaurants, shops, and everything that makes this city so special. At the end of the street, enjoy access to Old Woman's Cove and Spa Creek, grab your kayak or paddleboard and be on the water in minutes. Few homes in Murray Hill and the surrounding area offer this combination of nearly 5,000 finished square feet, newer Craftsman construction, exceptional architectural detail, garage parking, multiple outdoor living spaces, water access, and walkability. Come experience 8 Brooke Avenue and discover a home and an Annapolis lifestyle that is truly something special.

8 Brooke Ave, Annapolis

Listing courtesy of EXP Realty, LLC. Contact:

$1,295,000

Welcome to your future home in water-privileged Beacon Hill, where coastal living meets quality new construction. Set on a half-acre lot with a circular driveway, this to-be-built residence will be finished with durable Hardie Plank siding and architectural shingles for lasting beauty and low maintenance. The inviting design features a beautiful porch that wraps around to create a lovely seating area just outside the family room. Inside, 10-foot ceilings and luxury vinyl plank flooring create an airy, elegant main level with an open floor plan made for easy living and more formal entertaining if desired. The gourmet kitchen will inspire any home chef with quartz countertops, stainless steel appliances, and a generous pantry. A main-level bedroom offers flexibility for guests, multi-generational living, or single-level convenience. Upstairs, the primary suite is an oasis, complete with a gas fireplace, a luxurious bath, a walk-in closet, and private access to the veranda, the perfect spot for morning coffee or evening relaxation. Two additional bedrooms share a full bath, while an upstairs library provides a quiet space to read, work, or unwind. The laundry is conveniently located upstairs. A large shed adds valuable storage for kayaks, paddleboards, tools, and more. Don't miss the chance to tweak the options on the home you've been dreaming of in this exceptional waterside neighborhood! Beacon Hill has two access points for the Chesapeake Bay, and one is directly across from this property. It’s an easy commute into downtown Annapolis as well as to commute routes 50 and 97. Schools include Cape St. Claire elementary, Magothy River middle, and Broadneck high school.

1546 Shipsview Rd, Annapolis

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$799,000

Welcome home to lucky number 777 with over 3,000 finished square feet. You will fall in love with this very well maintained four bedroom, two & a half bath, colonial with a two car garage in sought after Cape St Claire. This property is made for entertaining large gatherings, with so much space to spread out! Wood floors throughout most of the main level, from the foyer to the spacious living room with a fireplace, into the formal dining room, and through the eat in kitchen. The cozy family room sits off from the kitchen and dining room. And, from the dining room step out to a wonderful enclosed porch with access to decks from both sides of the room. Upstairs find four ample sized bedrooms, with a huge primary bedroom with not only an attached bath and two walk-in closets, but a very large bonus room with so many options for use. The other three bedrooms share a the hall full bath, and the laundry is on the bedroom level for convenience. The back yard is fully fenced and ready to accommodate a large gathering or just enjoy the private setting as you relax in the fully functioning hot tub. New in summer of 2026 - roof, two HVAC system, and water heater****** Cape St Claire amenities include, beaches, fishing/crabbing pier, boat ramp, playgrounds, marina, & more. Broadneck School District. Close to shops and restaurants. Mins from Downtown Annapolis, and easy access for commuter routes to Washington, Baltimore, and close to Ft Meade. Great location, minutes from downtown Annapolis, and good commuter location with quick access to Rt 50 & I-97 close to Washington or Baltimore

777 Windgate Dr, Annapolis

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$859,000

NEWLY UPDATED! NEW BATHROOMS, GARAGE, and A BONUS 3rd FLOOR ROOM. Boasting 1,670 sq. ft. of finished historic charm, this 1905 Homewood treasure sits on a rare, oversized 0.26-acre lot! Offering space and flexibility nearly impossible to find this close to City Dock. While the main house charms with high ceilings, refinished hardwoods, and a light-filled 3-seasons wrap-around porch, the true crown jewel is the backyard oasis. Surrounded by stunning, mature trees and a double oversized lot as well as a brand NEW GARAGE WITH ELECTRICITY! Walk to the Navy Stadium, local cafes, and the Poplar Trail. Note on Square Footage: Finished square footage has been updated to 1,670 sq. ft. based on recent agent measurements. Public tax records currently reflect inaccurate historical data (1,442 sq. ft.) and do not fully capture the complete finished living area.

21 Woodlawn Ave, Annapolis

Listing courtesy of Real Broker, LLC - Annapolis. Contact:

$2,995,000

3 Beds ⋅ 4 Baths

A rare waterfront setting just off the Severn River, 1800 River Watch Lane is positioned on a private peninsula with more than 450 feet of shoreline along Luce Creek, offering exceptional privacy, sweeping water views and approximately 8 feet of protected deep water at the pier. From here, the Severn River is moments away and downtown Annapolis is an easy boat ride, an extraordinary setting for anyone who wants to make the Chesapeake Bay lifestyle part of everyday life. Approached by a long private drive and circular pea-stone courtyard, the extensively renovated residence sits high above the water, surrounded by mature trees and landscaping. Designed primarily on one level, the home takes full advantage of its elevated setting, with water views filling nearly every room and expansive outdoor living spaces overlooking the creek. At the center of the home, the dramatic living room pairs a wood-paneled cathedral ceiling with a floor-to-ceiling stone fireplace and an entire wall of glass facing the water. Doors open to a broad Ipe deck spanning the waterside of the home, creating a natural extension of the living space. Morning coffee overlooking the creek, dinner outside with friends or an evening in the hot tub all unfold against the backdrop of the water. The open layout continues into the dining and family areas, where cathedral ceilings, a gas fireplace and panoramic views create relaxed spaces equally suited to entertaining and everyday living. The adjoining chef's kitchen features marbled Silestone countertops, an extensive suite of Miele appliances, including double wall ovens, warming drawer and induction cooktop, along with a large walk-in pantry. The home's private spaces are equally thoughtful. A dedicated office with built-ins and an adjoining den or bedroom offer flexibility for working from home or accommodating guests. An architecturally distinctive, skylit hexagon hall leads to the bedroom wing and the waterside primary suite, a serene retreat with a gas fireplace, tray ceiling and oversized walk-in closet. The spa-inspired primary bath features a soaking tub positioned toward the view, large walk-in shower, double vanity and private sauna. Two additional bedrooms, including one ensuite, another full bath, separate laundry room and powder room complete the living spaces. Hardwood flooring, generous windows and clean contemporary finishes carry throughout the home, while a well-appointed mudroom connects to the oversized two-car garage. Outside is where the property becomes truly exceptional. The elevated homesite provides privacy and long views across Luce Creek, while a private funicular makes the trip from the house to the shoreline effortless. At the water, a substantial private pier with two boat lifts and approximately 8 feet MLW provides the kind of deep-water access that is increasingly difficult to find. The protected waters of Luce Creek offer an ideal home base for your boat, with the Severn River just beyond and the Chesapeake Bay easily accessible. Spend the morning on the water, cruise into downtown Annapolis for lunch or dinner, or simply enjoy the activity along the creek from the deck above. Despite its remarkably private setting, 1800 River Watch Lane remains convenient to downtown Annapolis as well as major routes to Baltimore, BWI, Washington, D.C. and the Eastern Shore. With its combination of substantial shoreline, protected deep water, immediate Severn River access, privacy and proximity to Annapolis, 1800 River Watch Lane offers a waterfront lifestyle that is increasingly hard to replicate.

1800 River Watch Ln, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact:

$1,700,000

Experience the ultimate walkable lifestyle in the heart of Downtown Annapolis with this charming traditional home in the Historic District, where timeless character meets modern comfort. Built in 1900, this inviting residence captures the quintessential charm of Annapolis while offering thoughtful updates and the conveniences of contemporary living. Steps away from the welcoming front porch you'll find boutique shops, waterfront dining, historic landmarks, and the U.S. Naval Academy. Inside, original hardwood floors and classic architectural details create a warm and inviting atmosphere. The layout features three bedrooms, two full bathrooms, and a half bath. The main level offers comfortable living and entertaining spaces along with a welcoming kitchen, while a carefully renovated room addition provides valuable additional living space. The primary bathroom has been beautifully styled with a luxurious spa-like feel, creating a peaceful retreat at the end of the day. Outdoor living is equally inviting, with a private patio and lush turf yard overlooking Cumberland Court—an ideal setting for morning coffee, al fresco dining, summer gatherings, or simply enjoying the charm of downtown living. Surrounded by the history, culture, shops, restaurants, and waterfront that make the Historic District so special, this distinctive home offers an authentic Annapolis lifestyle, blending historic charm, modern comfort, exceptional walkability, and an unusually generous amount of private parking.

219 King George St, Annapolis

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$540,000

Welcome to 1182 Bay Highlands Drive in Annapolis! This solid home offers a great opportunity for buyers looking to make a property their own in an established Annapolis community. The major systems have been replaced within the past few years, providing a strong foundation for future improvements. Price is reflective of the current condition of the home. The home is ready for updating and TLC, including cosmetic improvements to the kitchen, baths, flooring, and finishes. With the major systems already addressed, buyers can focus on renovations and personal touches to bring out the home's full potential. The asking price is reflective of the home's current condition and the updates needed. Property is being sold strictly "AS IS." Seller will make no repairs. A great opportunity for buyers with vision who want to customize a solid home and build equity in Annapolis.

1182 Bay Highlands Dr, Annapolis

Listing courtesy of CENTURY 21 New Millennium. Contact:

$929,000

Experience resort like living in the water-oriented community of Oyster Harbor! Why choose between elegance and Chesapeake living when you can have both?! This stunning property offers the perfect blend of style and comfort with the ease of access to a plethora of sought after water-oriented community amenities! The main level features a beautiful, open kitchen with walk-in pantry, stainless steel appliances, center island, and large eat-in space. The living room is truly the heart of the home featuring a cozy gas/propane fireplace- perfect for gathering for cozy evenings at home. The upper floor is home to all four bedrooms- two of which have attached bathrooms and walk-in closets- and the upper level laundry adds convenience to daily living. The attached garage, with space for two vehicles and additional storage, provides practicality without compromising on style with a large driveway making it easy for guest parking. One of the standout features of this property is the spacious deck and large backyard- indoor/ outdoor living at its finest! The community of Oyster Harbor offers an exclusive lifestyle for water enthusiasts, with opportunities for boating, fishing, and enjoying the natural beauty of the bay. Enjoy easy access to many community amenities including: a large beach with gazebo, two tot lots (one on the beach!), three community marinas, boat ramp, fishing pier, kayak storage, and more! This home is not just a residence; it's a gateway to a lifestyle of luxury and leisure. Experience the perfect blend of modern amenities and serene surroundings in this exceptional Oyster Harbor property.

1326 Harbor Rd, Annapolis

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$1,700,000

Come see this beautiful one-of-a-kind WATERFRONT property! Complete waterfront view from both levels of this home and every room. True master bedroom and large enough to fit a king-size bedroom suite and private bathroom. Covered patio to enjoy the view in every weather type! Large windows throughout the home brings in natural light while keeping the waterfront setting front and center. There are fireplaces on each level. Swim all year round with this heated indoor pool and hot tub. Dock rental slips are available for owners for a $500 fee for deep water (6ft) or lower water slips for $200 (3ft) with electricity. This property can have a personal pier added not to mention Just steps away from the community beach and docks. Arundel on the Bay also offers a community beach and an established waterfront neighborhood just minutes from everything Annapolis has to offer.

1323 Magnolia Ave, Annapolis

Listing courtesy of Keller Williams Select Realtors of Annapolis. Contact:

$574,900

4 Beds ⋅ 2 Baths

Price Improvement Incredibly maintained home in the sought-after water-privileged community of Beechwood on the Burley. This two-level home offers comfortable living, a spacious outdoor setting, and an ideal Broadneck Peninsula location just minutes from downtown Annapolis and with easy access to Route 50. The established community offers water access, a marina, playground, and peaceful neighborhood setting, with convenient back-road access to downtown Annapolis. Inside, the home has been well maintained and thoughtfully updated with refinished hardwood floors, fresh paint, updated lighting, and new carpet. The upper level features a comfortable open-concept layout with a living room that flows into the dining area and kitchen. Granite countertops, beautiful cabinetry, and a center island with seating create a welcoming kitchen with plenty of workspace. Sliding glass doors open to a composite deck overlooking the flat, fully fenced backyard, where mature landscaping provides privacy and a lovely backdrop for outdoor living. The primary suite features a private ensuite bath, accompanied by two additional bedrooms and a full hall bath. The lower level adds valuable living space with a family room centered around a propane gas fireplace, an office/fourth bedroom, laundry room, and access to the attached garage. Ample storage throughout adds to the home's everyday functionality. Beechwood on the Burley is a voluntary HOA community with access to a waterfront park, community dock with slips, playground, and picnic area along the water. The neighborhood's quiet roads and surrounding farmland create a peaceful setting for walking, running, and cycling, while the home's location provides easy access to Annapolis, Broadneck schools, shopping, dining, and major commuter routes.

626 Edwards Rd, Annapolis

Listing courtesy of Monument Sotheby's International Realty. Contact:

$879,000

Welcome Arundel on the Bay - a water oriented lifestyle community offering access to kayaking, paddle-boarding, beach and playground. All this with close proximity to shopping, restaurants, parks and downtown Annapolis. The quiet and calm neighborhood offers an island-like feeling. And this striking 3-story home is absolutely MOVE-IN READY! Gracious and plentiful windows leave you appreciating the timeless perennial gardens, majestic trees and peeks at Fishing Creek from multiple locations. As Fall arrives the "peeks" will become relaxing and lovely views! A bright and open floorplan features architectural lines and high ceilings which enhance the home's airy, gallery-like feel. Stunning wood floors offer warmth and continue the feeling of openness. We hope you like to cook and entertain - this Kitchen makes it not only possible but inviting and engaging. Extend your morning or evening and take a step out to the private back Deck tucked in to give you an intimate feeling with a lovely pergola and hanging lights. And it is only one of three Decks. The Primary Suite is magazine worthy - morning coffee on your Deck with lovely views or an evening toast to the day. Two more very spacious Bedrooms and updated Bath complete the 2nd Floor. And then the 3d Floor is worthy of the term "RETREAT". A wall of floor to ceiling windows with a side view of Fishing Creek and views of the trees and gardens below is icing on the cake! Amazing Community Features: Magnolia Avenue Beach, Newport Avenue Community Pier, Linden Avenue Recreational Pier, Redwood Avenue launching pier/boat ramp, and playgrounds.

3401 Saratoga Ave, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

$924,990

Huge Price Drop + $5,000 Closing Help! New Construction Colonial Ready by End of Year* New pictures coming soon!!! Schaefer Homes presents this stunning new Colonial in the prestigious Oyster Harbor community, with completion targeted for the end of 2026. Set on a sprawling 0.62-acre lot, it offers rare space and privacy, with plenty of room for a garden retreat, entertaining terrace, or open yard. The thoughtful floor plan includes 5 spacious bedrooms and 3.5 baths, plus a showstopping gourmet kitchen with upgraded design features and premium finishes. With its classic vinyl siding exterior and modern new-construction interior, this home blends timeless charm with the quality craftsmanship Schaefer Homes is known for. Oyster Harbor is a serene, exclusive community and one of the area’s most sought-after addresses. Don’t wait. Schedule your private appointment today! *Closing cost assistance terms and conditions apply.

3268 Kitty Duvall Dr, Annapolis

Listing courtesy of Blackwell Real Estate, LLC. Contact:

$850,000

Welcome to 327 Beach Drive, where thoughtful design, quality craftsmanship, and the relaxed Annapolis lifestyle come together in the heart of Hillsmere Shores a waterfront community. Completely transformed with a warm, modern aesthetic, this 4-bedroom, 3-bath home offers approximately 2,450 square feet of beautifully finished living space. From the moment you arrive, the crisp white board-and-batten exterior and inviting curb appeal set the tone. Inside, brand-new natural birch flooring, solid wood interior doors, crown molding, recessed lighting, and carefully selected finishes create a bright, cohesive feel throughout the main level. The open living spaces are designed for both everyday living and entertaining, highlighted by a custom shiplap fireplace that adds warmth and character. The kitchen flows naturally into the surrounding living and dining areas, creating an easy gathering space at the center of the home. A fully permitted addition created a stunning primary suite that feels like a private retreat, complete with a spacious bedroom, walk-in closet, and beautifully finished luxury bath. The additional main-level bedrooms are complemented by a custom-designed hall bathroom with timeless finishes and attention to detail. The finished lower level adds even more flexibility with a fourth bedroom, full bath, home office, additional living space, laundry, and storage—ideal for guests, working from home, or creating a separate recreation area. Outside, the large, level .41-acre lot is fully fenced and offers exceptional space for entertaining, pets, play, or gardening. A low-maintenance Trex patio extends the living space outdoors and provides the perfect setting for summer dinners, grilling, and relaxing with friends. Located in sought-after Hillsmere Shores with access to the community’s waterfront lifestyle and amenities of marinas, beach and pool, 327 Beach Drive offers the rare combination of a beautifully renovated home, generous outdoor space, flexible living areas, and an Annapolis location that makes it easy to enjoy everything the area has to offer. https://hillsmereshores.org/pool/ This isn’t simply an updated home—it has been thoughtfully redesigned for the way you want to live.

327 Beach Dr, Annapolis

Listing courtesy of RE/MAX United Real Estate. Contact:

$725,000

1 Beds ⋅ 2 Baths

A unique mixed-use opportunity in the heart of Annapolis! Located in the Arts District, 232 West Street offers the flexibility of commercial and residential use in a convenient location close to Downtown Annapolis, Navy-Marine Corps Memorial Stadium, and the U.S. Naval Academy. Renovated in 2018, the property is currently configured for residential use with one bedroom and one and a half baths. Skylights and abundant natural light create a bright, welcoming feel throughout. The updated kitchen features white cabinetry, stainless steel appliances, a subway tile backsplash, and an island with seating, while hardwood floors add warmth and character. The spacious primary bedroom offers two closets and direct access to a private deck. The adjoining bathroom features a dual-sink vanity and a shower with dual shower heads. A separate studio in the rear provides additional flexible space with a variety of potential uses. The fenced yard adds privacy and creates a nice connection between the property, outdoor space, and the studio, while a shed provides additional storage. In-home laundry and a tankless water heater add to the property's conveniences. Situated on an approximately 2,700-square-foot lot, the property also offers potential for future expansion, subject to applicable zoning and approvals. Enjoy a prime West Street location with easy access to Downtown Annapolis, City Dock, restaurants, and shops, along with convenient access to Routes 50 and 97. A versatile property with a unique combination of location, character, and flexibility.

232 West St, Annapolis

Listing courtesy of Engel & Volkers Annapolis. Contact:

$614,900

There's a version of Annapolis living where you don't have to choose between being close to everything and having room to enjoy being home. With a VA assumable loan at an interest rate of approximately 2.7%–2.8%, qualified buyers may also have an opportunity to secure financing at a rate that's difficult to find in today's market. This updated 3-bedroom, 2-bath home sits in a residential setting just minutes from downtown Annapolis, the Naval Academy, Eastport, marinas, restaurants, and shopping, while offering something that can be hard to find this close to the city: real outdoor space. Step outside and the fully fenced backyard speaks for itself. A covered deck flows to the patio and firepit, creating a space for morning coffee, dinner outside, a quiet evening by the fire, or hosting when you want to. Inside, the home balances comfort and function. Both baths feature updated showers, and the fireplace anchors the main living area. The partially finished basement with a bar adds flexible space for entertaining, movie nights, or whatever fits the way you live. The updates go beyond cosmetic. The covered deck and roofs on both the home and garage were replaced in 2021, the fence was added in 2024, and a new front porch, mailbox, walkway, and water heater followed in 2025. The detached garage adds parking and storage, with room for a workshop. Close to the energy of Annapolis, with plenty of room to unwind when you get home. VA loan assumption is subject to loan servicer approval, buyer qualification, and applicable requirements.

1033 Hyde Park Dr, Annapolis

Listing courtesy of Real Broker, LLC - Annapolis. Contact:

$925,000

Welcome to 1422 Bay Head Road, a true Annapolis oasis offering flexible living space, thoughtful updates, and exceptional outdoor amenities. The upper level features four bedrooms, including a large primary suite with barn siding accents, a custom closet, and an ensuite bath with a large soaking tub and separate shower. Three additional bedrooms share a hall bathroom. The main level includes a living room, dining room, and kitchen with stainless steel appliances, granite countertops, and a center island. The family room features a fireplace and provides a comfortable space for everyday living and entertaining. The finished lower level adds even more versatility with a family room, custom bar, and a large storage room. Outside, enjoy professionally landscaped grounds, a large deck overlooking the built-in pool and spa, and convenient access to a full bathroom with shower. A generous yard with firepit creates an inviting setting for outdoor gatherings. The property also includes a greenhouse/chicken coop. The community offers nearby water access for kayaks and canoes and is close to parks and walking trails B&O bike trail, golf cart to Podickory Point Yacht & Beach Club. Conveniently located with easy access to Route 50, the Bay Bridge, and downtown Annapolis.

1422 Bay Head Rd, Annapolis

Listing courtesy of RE/MAX United Real Estate. Contact:

$1,675,000

5 Beds ⋅ 3 Baths

Ideally situated on the corner of Prince George & College Ave(across from St Johns College), this distinguished residence is tucked in the heart of Historic Downtown Annapolis. This exceptional home offers the charm of an Historic home built circa 1800's with modern conveniences. Soaring ceilings and windows create sun-drenched rooms with beautiful views of the grounds at St. Johns College. This home was built for entertaining. It has amazing flow to entertain your guests for a dinner party. Take a short walk to outdoor dining on West Street during "Dinner Under the Stars" or host friends for all the amazing Downtown events like Midnight Madness. This home is in the heart of it all! The electrical and plumbing was updated in 1990, new hot water heater in 2024, 2 heat pumps in 2025 and new Shake Shingle roof in 2026. There are 4 bedrooms and 2 full baths on the second floor with a bonus room on the third floor great for guests or office. All this just 1.5 blocks from the Naval Academy and steps to the shops and amazing restaurants Annapolis has to offer! There is driveway with private parking for 2 cars and plenty of street parking for guests. Walk to City Dock for morning coffee and watch the boats pass by or sit in the morning room and enjoy your coffee looking over the grounds of St. Johns. This is an amazing house in an amazing location with all that Annapolis has to offer.

250 Prince George St, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

$1,395,000

4 Beds ⋅ 5 Baths

Highly desirable Eastport location just a short walk to Historic Annapolis, the U.S. Naval Academy, vibrant restaurants, boutique shops, and multiple marinas. This rare offering features essentially two separate homes on one property, creating an exceptional opportunity for multi‑generational living, guest accommodations, potential rental income, or a private studio/office retreat. The beautifully updated three‑level Cape Cod has been thoughtfully expanded and modernized. It features a gourmet kitchen, hardwood floors, two generous bedrooms, and 2.5 bathrooms. The main level office provides flexibility and can easily function as an additional bedroom. Every level blends comfort with style, offering bright spaces and quality finishes throughout. At the rear of the property sits an eclectic secondary structure with two cozy bedrooms and two full baths. Its lower level includes garage space and abundant storage ideal for bikes, paddleboards, tools, or seasonal items. Outdoor living shines here: a spacious deck and stone patio create inviting spaces for entertaining, grilling, or unwinding in a peaceful setting. With numerous exterior upgrades and a location that captures the best of Eastport living, this property is truly one of a kind.

1030 Boucher Ave, Annapolis

Listing courtesy of Curtis Real Estate Company. Contact:

$650,000

Welcome to 953 Mastline Drive, a spacious ranch style home in the highly sought after 55+ community of Heritage Harbour. Offering just under 2,000 square feet, three bedrooms, two full bathrooms, and a two car garage, this home provides easy single level living with plenty of space to enjoy. Inside, fresh paint and brand new carpet give the home a clean, refreshed feel throughout. Generous living and dining areas offer flexibility for everyday life and entertaining, while the primary suite features its own private bathroom. Updated windows and HVAC, along with new insulation, add to the improvements already completed, allowing you to move right in while still having the opportunity to personalize the home over time. Heritage Harbour offers an impressive collection of amenities, including indoor and outdoor pools, a fitness center, tennis and pickleball courts, a nine hole golf course, community Lodge, library, and an extensive calendar of clubs, activities, and social opportunities. Shopping, dining, healthcare, and everyday conveniences are nearby, with easy access to Routes 50 and 97 and Historic Downtown Annapolis just a short drive away. Combining a spacious ranch layout, valuable updates, and the active lifestyle of one of the Annapolis area’s most established 55+ communities, 953 Mastline Drive is ready to welcome its next owner.

953 Mastline Dr, Annapolis

Listing courtesy of Next Step Realty, LLC.. Contact:

$735,000

Nestled in the sought-after community of Hunt Meadow, and on a quiet cul-de-sac, this perfectly-kept colonial home offers the right blend of comfort and privacy. Featuring 4 bedrooms and 2.5 baths, a family room with a cozy fireplace, raised hearth and framed in brick. Vaulted ceilings, and custom oak hardwood floors. The kitchen features stainless steel appliances, granite counter tops and modern plank flooring. The entire second level, stairs, and living room feature all NEW carpeting. The primary bedroom has a spacious en-suite bath. Two additional bedrooms and an additional full bath are on this level. The finished basement offers additional space for recreation with a Movie Room featuring a large TV screen, movie projector and stereo system that all conveys with the property. A walk-in cedar-lined storage closet, a laundry room with front-load washer and dryer, and a fourth bedroom. The exterior features a brand NEW deck, and fire pit - ideal for enjoying the quiet outdoors. The back yard is private, partly wooded, and has trails leading from it for exploration. The garage is equipped with shelves and a workbench for projects. Residents enjoy access to community amenities such as the large outdoor pool, tennis courts, and scenic jog/walk paths that connect to Quiet Waters Park. The neighborhood is well-maintained, with sidewalks for leisurely strolls. Lots of community spirit here with swim meets, 5k runs, food trucks, holiday celebrations and other get-togethers. Hunt Meadow is just minutes from downtown Annapolis and convenient to Rts. 97 and 50

303 Riding Ridge Rd, Annapolis

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$1,300,000

A rare opportunity to own a fully metered triplex in the heart of Downtown Annapolis where historic charm, prime location, and remarkable versatility come together. Steeped in character and offering exceptional flexibility, this distinctive property presents an array of possibilities for both lifestyle and investment. With separately metered electricity, the property can be enjoyed as a multigenerational residence, with each family member having their own private space; an owner-occupied home with additional rental income from the remaining units; or a pure investment property with multiple income producing residences. For those envisioning something truly extraordinary, the entire building could be transformed back into a stunning single-family home. With original architecture and showcasing hardwood floors throughout, this property strikes the perfect balance between historic character and modern livability. The first floor features two bedrooms, each with an en-suite bath, kitchen, and living room, ideal for an owner-occupant or long-term tenant. The second floor offers one bedroom, a full bath, kitchen, living room, and access to a private balcony. The third floor impresses with two bedrooms, a full bath, kitchen, and living room, plus its own private balcony. An unfinished basement provides excellent storage space. A fenced backyard complete with a paver patio, provides an outdoor retreat ideal for relaxing or entertaining. Add to that the coveted off-street parking, a true rarity in Downtown Annapolis, and this property is as practical as it is beautiful. Whether you're an investor seeking immediate income potential, a buyer looking to offset your mortgage, or a multigenerational family wanting separate yet connected living spaces, this home checks every box. All of this just steps from the vibrant shops, restaurants, waterfront, and history that make Downtown Annapolis truly one of a kind.

135 Conduit St, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact:

$789,900

Don't delay - grab your agent and schedule a tour today! Welcome to 2691 Claibourne Road, beautifully presented and ready to impress in the sought-after water-privileged community of Annapolis Roads. This spacious 4-bedroom, 3.5-bath Colonial offers a flexible floor plan, finished lower level, two-car garage and inviting indoor and outdoor spaces designed for everyday living and entertaining. Step inside to hardwood floors and light-filled living spaces that flow comfortably throughout the main level. The updated kitchen features granite countertops and opens to the home's gathering areas, while separate living and dining rooms provide plenty of room for entertaining. Just beyond, the screened-in porch overlooks the peaceful, wooded backyard and offers the perfect spot for morning coffee, outdoor dining or relaxing at the end of the day. Upstairs, the spacious primary suite features a vaulted ceiling, oversized walk-in closet and private bath with a sunken tub and separate shower. Three additional bedrooms and a full hall bath complete the upper level. Downstairs, the finished lower level adds even more flexibility with a family/rec room, full bath and generous storage—ideal for guests, a home office, workout space or additional living area. Additional features include a whole-house generator, newer heat pump, water-softening system, two-car garage and custom shed with electricity. Fresh landscaping and new mulch enhance the home's curb appeal, while the wooded backyard provides a private setting for relaxing and entertaining. Just a short walk down Claibourne Road, take in beautiful sights of Lake Heron—one more reminder of the special setting that surrounds this home. Annapolis Roads residents enjoy an exceptional water-privileged lifestyle with access to the community's private beach, boat ramp, piers, waterfront pavilion and picnic area, playground, fire pit, kayak storage, walking trails and neighborhood events. All of this is just minutes from Downtown Annapolis, shopping, dining and commuter routes. Beautifully staged, refreshed and ready for its next chapter—come experience 2691 Claibourne Road for yourself!

2691 Claibourne Rd, Annapolis

Listing courtesy of EXP Realty, LLC. Contact:

$500,000

4 Beds ⋅ 2 Baths

Inside the Annapolis city limits on a cul-de-sac, this Dutch Colonial pairs four bedrooms and two full baths with a fully fenced yard and about 1,928 finished square feet on three levels. A bedroom and full bath on the main level give guests their own space or make room for a home office, and three more bedrooms and a second full bath are upstairs. The fully finished basement adds room for a rec room, gym, or office. End the day in the steam shower with full body sprays, then light the wood-burning fireplace and let the blower carry the heat through the room. Out back, a deck steps down to the fenced yard, and a shed adds storage. The driveway parks two cars. Wilshire sits off Forest Drive, a short drive from the trails and waterfront at Quiet Waters Park, the restaurants of Eastport, the Annapolis Maritime Museum, and City Dock. Route 50 and the Bay Bridge put Washington, DC, Baltimore, and the Eastern Shore within reach, for the commute or for the weekend. Ask your agent about a lender closing-cost credit of up to $2,000 for applications by December 31, 2026, and no lender fees on VA loans.

1017 Hyde Park Dr, Annapolis

Listing courtesy of EXP Realty, LLC. Contact:

$9,500,000

6 Beds ⋅ 10 Baths

Located on a private 2.5-acre lot in Wimbledon Farms, this waterfront estate home, designed by Cathy Purple Cherry and constructed by West River Builders, is truly a masterpiece in design and quality. The 3-level home – complete with elevator -- takes full advantage of its waterfront setting that includes 400 ft of shoreline. Facing Quiet Waters Park, the ever-changing view includes brilliant fall foliage, deer by the water’s edge, and osprey circling overhead. Stroll down to the 100 ft private pier with deep-water slips. There’s 7 ft water depth at the dock; Harness Creek is a recognized hurricane hole so this is the perfect spot for boats to ride out a storm. The 20 ft x 40 ft saltwater pool has a spacious ipe deck and two Hanso pergolas provide shade with wonderful water views. Six bedrooms, each with a private ensuite bath, a gourmet kitchen, and wrap-around screen porches and decks provide space for both casual living and grand entertaining. Upon entering, there is a gracious paneled foyer that opens to the living room. With Brazilian cherry floors, a gas fireplace with marble surround, and built-in bookcases, this room has fabulous water views and opens to one of the screened porches on this level that invite outdoor living. To the right is the heart of the home – the great room. It includes a just remodeled chef’s kitchen with multiple work areas, a family room, and the dining area. The kitchen includes Taj Mahal leathered countertops, two wall ovens, two Bosch dishwashers, a warming drawer, instant hot dispenser, Wolf 5-burner gas cooktop, and KitchenAid side-by-side refrigerator. There’s also a wet bar with beverage cooler. The family room has a wood-burning fireplace with raised hearth and stone surround; there’s also a spacious workspace with built-in bookshelves. The dining area overlooks the water, and there’s access to both screened porches. The main level also features a fabulous guest suite: there is a large bedroom with water views, walk-in closet, and a private bath with radiant heated floor. In addition, there are two powder rooms and a mudroom with three closets and an abundance of storage space. The main level has 10 ft ceilings and 8 ft interior doors. Upstairs, the primary suite is an owner’s dream escape. There’s a spacious bedroom with water views, dark cherry floors and a gas fireplace. The study, with wet bar, built-in shelves and file drawers, leads to a small reading room – with water views. The spa-like bathroom, with radiant heated floor, includes a separate water closet room, jetted tub with marble surround, oversized steam shower, and separate vanities. Step onto the private screened porch to enjoy a cup of coffee in the morning. The primary suite also includes two large walk-in closets and a laundry room. There are three additional water view bedrooms on the second floor, each with private bathroom and walk-in closet. The main laundry is in a dedicated room with ample storage. There’s also a walk-in cedar closet. All of the bedrooms and closets that have carpeting were re-carpeted in 2026. The walk-out lower level has a huge game room that includes a big screen TV, wet bar, and full bathroom. From here, you can step out to the bluestone patio that leads up to the pool. There is a half-bath off the patio, accessible for pool visitors. The 6th bedroom with ensuite bathroom also has peaceful views, and multiple closets. The main utility room houses the commercial grade water treatment system. It has a garage door for easy access to boat supplies and equipment servicing. A secondary utility room houses the elevator mechanism and reverse osmosis treatment system. A third unfinished area has the camera and internet systems. This exceptional home offers sophisticated waterfront living just minutes from the heart of Annapolis and the Chesapeake Bay. The year-round beauty of this scenic setting and unrivaled design is truly unsurpassed!

3285 Harness Creek Rd, Annapolis

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$2,795,000

Live authentically. The Chesapeake Bay is the view, the backdrop and the reason to linger. From the covered bluestone porch, the horizon opens across the Bay with uninterrupted sky and water. Morning coffee, an afternoon breeze through open doors, evenings around the fire—the water sets the pace. Extensively renovated inside and out since 2019, this charming craftsman styled gem in the sought-after Bay Ridge Community offers easy one-floor living and a natural connection to the outdoors. Windows and skylights, French doors and Phantom screens invite the sunshine and bay breeze inside. New Café Elite appliances, induction cooktop, and laundry. Freshly painted, craftsman style trim, molding and shiplap accents. Open floor plan with wide plank hickory flooring. Set on a generous .31 are lot, the flat, manicured backyard leaves plenty of room for games, children and pets. Low-maintenance Ipe deck and rear entry porch made for entertaining. Ample storage for water toys, paddle boards and bikes. Outdoor shower adding another practical touch to life by the water. Oversized parking pad for guests. Detached 2 car garage/studio, heated and cooled, skylight and separate personnel door offers flex space for home gym, office or guests. Functional updates include architectural shingle roofs, Pella windows, Hardie siding, hurricane French doors, blown attic insulation and generator hook- up. Then there is Bay Ridge itself—a walkable waterfront community with the quiet, unhurried character of a New England shore town. Tree lined streets, community beaches, deep water marina, pool and clubhouse are part of the fabric, while effortless biking connects the neighborhood to shoreline points along the South and Severn Rivers. A coveted pool bond conveys. Eastport, with its waterfront restaurants, marinas and distinctly maritime character, is close by, as are the Annapolis Maritime Museum & Park and Quiet Waters Park, with miles of trails and waterfront access. Historic downtown Annapolis, City Dock and the U.S. Naval Academy bring dining, shopping, sailing, history and the traditions of one of the country's most distinctive institutions at your doorstep. Zippy routes south to Washington, DC and Northern Virginia, north toward Baltimore, and across the Chesapeake Bay Bridge to Maryland’s Eastern Shore. BWI Airport and the Amtrak/MARC station are under 35 minutes away. Chesapeake Bay cottage lifestyle with the water in front of you, a community around you and the region within easy reach. Cultivate your existence. The art of uniting human and home.

113 Bay Dr, Annapolis

Listing courtesy of Krauss Real Property Brokerage. Contact:

$1,875,000

***Owner financing available at 6%*** Experience the best of the Annapolis lifestyle from this beautifully reimagined coastal Craftsman in the heart of Eastport. Ideally located within walking distance of downtown Annapolis, the waterfront, restaurants, shops, yacht clubs, marinas, and the many neighborhood amenities that make Eastport one of the area's most desirable communities, this extensively renovated home offers an exceptional combination of location, character, and modern comfort. Offering approximately 4,099 square feet of finished living space, the home features three bedrooms, a dedicated office, four bathrooms, and a versatile floor plan designed for both everyday living and entertaining. A welcoming front porch sets the tone, while James Hardie siding, Andersen 400 Series windows, low-maintenance exterior materials, and extensive improvements provide the benefits of a thoughtfully updated home while preserving its classic Eastport character. Inside, hardwood floors, high ceilings, substantial trim work, a fireplace creates warmth and architectural interest. Generous living and dining spaces flow naturally into the kitchen and family room, creating an inviting setting for entertaining or relaxed everyday living. Dual staircases provide access from both the front and rear portions of the home and add a distinctive architectural element to the floor plan. Upstairs, the spacious primary suite serves as a private retreat with a spa-inspired bath featuring a soaking tub, frameless glass shower, and dual vanity. Two additional bedrooms provide comfortable accommodations, while a separate office offers an ideal space for working from home. Convenient second-floor laundry completes the upper level. The fully finished lower level significantly expands the home's versatility, offering generous space for a recreation room, home gym, media room, or potential fourth bedroom. Full egress provides added flexibility for buyers who need additional sleeping accommodations, while ample storage enhances the functionality of the space. Outside, a large rear deck overlooks the generously sized yard, providing plenty of room for outdoor dining, entertaining, gardening, or simply relaxing at home. Three off-street parking spaces are an exceptional convenience in Eastport, while the property also offers potential for a future garage, accessory dwelling unit, and/or pool, subject to applicable approvals. Beyond the property itself is the lifestyle that makes this location so special. Leave the car at home and explore Eastport's restaurants, marinas, yacht clubs, and waterfront destinations, or stroll across the Spa Creek Bridge into historic downtown Annapolis and City Dock. Spend the morning on the water, meet friends for dinner in Eastport, or walk downtown for an evening along the harbor—all just minutes from your front door. 400 Jefferson Street offers the space and amenities of a substantially renovated home paired with the walkability, waterfront culture, and unmistakable character of Eastport. This is Annapolis living at its best.

400 Jefferson St, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact:

$1,250,000

Welcome to 700 Miller Road. Discover a truly special property tucked away on a private road, yet just minutes away from historic downtown Annapolis. Located less than a 5-minute walk from the Naval Academy Marine Corps Stadium, this beautifully renovated 2026 home offers the rare combination of privacy, convenience and Annapolis charm. Set on a generous .598-acre tract, the property backs-up to Tawes Gardens, that gives the home a tranquil and private setting. The home has been completely renovated in 2026, both inside and out, offering thoughtful updates while maintaining the integrity of the community. Enjoy the best of Annapolis, all within walking distance or true city living just a short drive away. Welcome home to 700 Miller Road. Ask about great below market seller financing.

700 Miller Rd, Annapolis

Listing courtesy of Cottage Street Realty LLC. Contact:

$1,495,000

A significant price reduction has been made on this stunning home! Rarely does a home of this historical significance become available in the heart of Historic Annapolis. Believed to date to the late 17th century, the extraordinary residence is among the city's oldest surviving homes, seamlessly blending centuries of architectural heritage with sophisticated modern living. Perched at the water end of Market St overlooking Spa Creek and parking on both sides of street, this home is instantly recognizable by its iconic red standing-seam roof and timeless presence. Rich in character, the interior showcases exposed original beams, soaring ceilings, abundant natural light, and thoughtfully designed living spaces that honor the home's remarkable past while embracing contemporary comfort. A nationally recognized renovation in 1977 by Gate One Builders, transformed the residence into a one of a kind masterpiece, preserving its historic integrity while creating an open, light filled floor plan unlike any other in Annapolis. The beautifully appointed Kitchen, inviting living and dining areas, combination gas and wood burning fireplaces and a tranquil large Sunroom addition all flow effortlessly to a private walled courtyard, an intimate outdoor retreat ideal for entertaining or quiet relaxation and completely fenced in. Features 2 ensuite Bedrooms and a 3rd enclosed Bedroom easily adapted into a private home office or gym while still preserving the home's architectural flow. Water Views of Spa Creek, exceptional craftsmanship, and architectural details at every turn make this home as captivating as it is livable. Adding to its rarity are amenities seldom found with the Historic District, including two covered off street parking spaces and an unparalleled waterfront setting just moments from City Dock, the USNA, fine dining, boutiques, galleries and yacht club. Whether enjoyed as a full time residence or an exceptional Annapolis retreat, 100 Market Street represents a once in a generation opportunity to own an irreplaceable piece of the city's history, where more than three centuries of heritage meet the very best of coastal luxury living.

100 Market St, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

$899,999

Take advantage of an ASSUMABLE 2.25% VA LOAN!!!! Do NOT have to be a VA buyer!!! Nestled in the charming Admiral Heights neighborhood, this stunning split-level home exudes warmth and character, inviting you to experience its unique design and craftsmanship. Built with everyone in mind, this residence boasts timeless appeal with its classic brick-and-vinyl siding exterior, harmoniously blending with the lush surroundings. Step inside to discover a spacious layout that offers both comfort and functionality. With five generous bedrooms and three and a half bathrooms, this home is perfect for those who appreciate space and versatility. The heart of the home features a cozy fireplace, creating an inviting atmosphere for gatherings and quiet evenings alike. The partially finished basement provides endless possibilities, whether you envision a workshop, a play area, or additional storage. The expansive lot offers ample outdoor space for relaxation and recreation, while the community pool adds a refreshing touch for those warm summer days. Parking is a breeze with an attached carport and additional driveway space, ensuring convenience for you and your guests. This home is not just a place to live; it's a sanctuary where cherished memories are made. Experience the perfect blend of classic design and modern living in this delightful Admiral Heights gem. Don't miss the opportunity to make this house your home!

13 Rickover Ct, Annapolis

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$650,000

RARE OPPORTUNITY! TWO HOMES ON ONE LOT IN EASTPORT! This versatile property offers an exceptional combination of character, functionality, and flexibility with a renovated 2-bedroom, 1.5-bath main home PLUS a separate 1-bedroom, 1-bath guest house. The main residence features gleaming hardwood floors, a cozy fireplace, and a spacious kitchen with abundant counter space, a large peninsula, and stainless-steel appliances. The inviting layout provides comfortable living spaces while retaining the charm and character buyers love. The detached guest house is a standout feature, offering a private bedroom, full bath, living room, washer/dryer, and separate utilities. Ideal for guests, extended family, a private home office, or other flexible living arrangements. Enjoy the outdoors in the pleasant, tree-lined backyard, enclosed by a privacy fence. A 1+ car garage and shed provide plenty of room for parking, storage, hobbies, and outdoor equipment. Located conveniently to the restaurants, shops, waterfront, and attractions of Eastport and Downtown Annapolis, this property puts you close to everything while offering the flexibility of two separate living spaces. Notable recent improvements include: New roof and skylights (2023) New driveway (2022) Guest house electrical wiring (2022) New dishwasher (2024) Two homes. One lot. Endless possibilities. A unique opportunity in a highly desirable Annapolis location!

906 Jackson St, Annapolis

Listing courtesy of EXP Realty, LLC. Contact:

$879,990

Ameri-Star Homes is proud to offer this exceptional opportunity to build a brand-new Craftsman-style home on a beautiful 9,225-square-foot corner homesite in the sought-after waterfront community of Cape St. Claire in Annapolis. For A Limited Time - Builder is offering $25,000 towards Financing, Closing Costs or Options, with the use of the builder’s approved lender and title company! The exciting Bancroft model offers approximately 2,472 square feet of above-grade living space and is thoughtfully appointed with the quality features and finishes today’s homebuyers desire. Enjoy a spacious 12’ x 16’ sunroom, 9-foot ceilings on the main level, engineered hardwood flooring throughout the entire first floor, granite or quartz kitchen countertops, and upgraded cabinetry with soft-close doors and drawers. Additional included features include ceramic tile in the bathrooms and laundry room, stainless steel kitchen appliances, a washer and dryer package, upgraded Craftsman-style moldings, Craftsman newel posts with oak handrails and black iron pickets, stone exterior accents, architectural roof shingles, a Wi-Fi-enabled garage door opener, a sodded lawn, a generous landscaping package, and so much more. Best of all, these exceptional features are included as standard! There is also plenty of opportunity to expand your living space with available options, including a finished recreation room, additional basement bedroom, and full bathroom, all available at an additional cost. Come home and enjoy the incredible lifestyle and amenities offered in this water-privileged community. Cape St. Claire offers three community beaches, community docks, a fishing and crabbing pier, picnic areas, boat launches, playgrounds, baseball fields, basketball courts, marinas, boat ramp and slips, a community clubhouse, and an outdoor pool available with membership. Conveniently located with easy access to Annapolis, Baltimore, and Washington, D.C., this is a rare opportunity to enjoy new construction in the desirable Cape St. Claire community. A home you will be proud to come home to! Photos and images shown may be representative of the builder’s work, craftsmanship, and quality and may include optional features not included in the base price. Prices, terms, conditions, features, and availability are subject to change without prior written notice.

1049 Sun Valley Dr, Annapolis

Listing courtesy of Douglas Realty LLC. Contact:

$629,900