Annapolis 5 Bedroom Properties for Sale

Some homes offer a change of scenery. Others offer an entirely different perspective. Tucked away on 2.75 wooded acres bordering the Sherwood Forest Nature Preserve, 929 Sherwood Forest Road is a refreshing departure from the expected. Mature trees, natural beauty, and an exceptional sense of privacy create a setting that feels worlds away, yet remains just minutes from the heart of Annapolis. It's a rare balance of seclusion, convenience, and character. Inside, the home is every bit as compelling as its surroundings. Soaring vaulted ceilings, expansive windows, and a thoughtfully connected floor plan create an immediate sense of openness, with natural light and wooded views taking center stage. At the heart of the home, a beautifully designed kitchen makes a statement with a quartz waterfall island, a quartz backsplash, and a custom, handcrafted Italian induction range and oven. Envisioned for everyday living and effortless entertaining, the kitchen flows seamlessly into the main gathering spaces, including an inviting family room anchored by a wood-burning fireplace. Multiple decks extend the living experience outdoors. The upper level continues the home's inviting atmosphere, with the primary suite and additional bedrooms offering comfortable accommodations and flexibility for family or other evolving needs. The primary suite brings an entirely different level of comfort to everyday living. A beautifully renovated en-suite bath with dual vanities and an oversized shower creates a spa-like experience, while a spacious walk-in closet adds thoughtful functionality. The true standout is a private balcony overlooking the wooded landscape, where the natural surroundings become an extension of your own personal retreat. With more than 4,600 square feet of finished living space, there's room to entertain, create, unwind, and everything in between. The finished walkout lower level offers additional space for recreation and guests, while a detached custom studio presents an inspiring opportunity for a private office, creative retreat, or something entirely your own. An attached two-car garage adds everyday convenience without compromising the home's distinctive character. Beyond its architectural appeal, the property has benefited from substantial improvements, including a new roof (2020), a new front porch (2022), a new HVAC system (2025), and all-new electrical throughout. The septic system was also professionally pumped in 2025, further reflecting the care and attention invested in the home. 929 Sherwood Forest Road is more than a beautiful place to call home. It's an opportunity to experience Annapolis living from an entirely different perspective.

929 Sherwood Forest Rd, Annapolis

Listing courtesy of Keller Williams Realty Centre. Contact:

$749,999

Welcome home to this charming Waterview colonial in sought after Cape St Clarie community. Enjoy your morning coffee or an evening beverage on your expansive deck while taking in the views of the Little Magothy River. This home has so many wonderful features. The main level as you enter the home has a separate living area with a dining area right off that. The large gourmet kitchen will be the heart of the home with the sprawling open floor plan. Off the family room you step out to the spacious deck and enjoy the river views year-round. The upper level boasts 3 ample sized bedrooms, with the primary enjoying its own primary bath. If that wasn't enough, the lower level has another whole separate living area, with a kitchen, full bath, laundry, 2 bedrooms, a living room and its own separate entrance from the main level of the house. The exterior has a great, fenced yard for the family and the pets to enjoy, there is even an above ground pool for summertime enjoyment. The community has a beach, clubhouse and boat slips available for an additional fee. Don't miss out for a chance to own in this community!

962 Woodland Cir, Annapolis

Listing courtesy of Rosendale Realty. Contact:

$625,000

Beautifully Updated 5-Bedroom Home in The Landings of Annapolis! Welcome to 7 Landings Court, where spacious living, modern updates, and fantastic community amenities come together! This beautifully updated home offers 5 bedrooms, 3.5 bathrooms, and approximately 2,500 square feet of finished living space across three levels. Step inside to discover a thoughtfully designed floor plan featuring a convenient main-level bedroom, perfect for guests, a home office, or flexible living arrangements. The brand-new kitchen showcases all-new cabinetry and appliances, creating a fresh, inviting space for everyday living and entertaining. Upstairs, you’ll find three generously sized bedrooms and two full bathrooms, including a private primary suite. The finished lower level provides even more versatile living space, complete with a fifth bedroom, full bathroom, and plenty of room for recreation, entertaining, or relaxation. Enjoy outdoor living at its finest with a charming covered front porch, an expansive approximately 40-foot-wide rear deck, and a spacious, fully fenced backyard offering endless possibilities for entertaining, gardening, or simply unwinding. A two-car driveway provides convenient off-street parking. Located in the desirable Landings community, residents enjoy access to wonderful amenities, including a swimming pool, tennis courts, and pickleball courts, with an HOA fee of $140/Month. With five bedrooms, extensive updates, flexible living spaces, and outstanding community amenities, this Annapolis home offers an exceptional opportunity. Make sure to book your showing before its gone!

7 Landings Ct, Annapolis

Listing courtesy of Alberti Realty, LLC. Contact:

$1,499,000

Unique opportunity to own a brand-new home with builder’s warranty on 1.4 acres in an established Annapolis community. Just 5 minutes from Annapolis shopping. Welcome to 1907 Mackiebeth Court, an exceptional new construction home in the established Twin Hills neighborhood of Annapolis. Offering over 5,000 square feet of finished living space on a private 1.4-acre lot backing to a wooded area, this 5-bedroom, 4.5-bathroom home presents a rare opportunity in the Annapolis market. Built by local builder Howmar Homes, the property showcases craftsmanship, thoughtful design, and premium finishes that go well beyond typical builder-grade construction. The light-filled main level features an open floor plan centered around a gourmet kitchen with quartzite countertops, an oversized island, and premium Samsung & Maytag appliances. The kitchen flows seamlessly into the family room with 10-foot ceilings and a gas fireplace, while the morning room and expansive conservatory provide additional spaces for entertaining and everyday living. Upstairs, the spacious primary suite features a private sitting area, dual walk-in closets, and a luxurious bathroom with a soaking tub, walk-in shower, dual vanities, and separate water closets. Convenient upper-level laundry adds everyday practicality. The finished walkout lower level includes a large recreation room, fifth bedroom, full bathroom, and additional unfinished storage space. Outside, the expansive property offers plenty room to enjoy the outdoors. The approved grading plan includes an optional in-ground pool and patio space, offering exciting opportunities to further enhance the home's outdoor living spaces. Additional features include a side-entry three-car garage and a one-year builder warranty from Howmar Homes. With very few newly constructed homes in the Annapolis area offering this combination of finished square footage, acreage, and elevated craftsmanship, 1907 Mackiebeth Court is a truly unique opportunity. Enjoy the space and privacy of a large property just minutes from downtown Annapolis, waterfront attractions, shopping, and dining.

1907 Mackiebeth Ct, Annapolis

Listing courtesy of Douglas Realty LLC. Contact:

$700,000

5 Beds ⋅ 3 Baths

Stunning, updated home on a spacious .6-acre lot located just 2 miles from historic downtown Annapolis. The main level boasts beautifully refinished hardwood floors, updated eat-in kitchen, and a separate dining room. The bright living room with a wood-burning fireplace flows effortlessly toward outdoor living, featuring a spacious screened-in porch that exits to a large back deck. A desirable main-floor bedroom with a full ensuite bathroom offers ultimate convenience. Upstairs, you will find three additional hardwood-floored bedrooms sharing a tastefully updated full bathroom. The versatile basement provides a flexible space perfect for a rec room or fifth bedroom, complete with a full bath, laundry, and ample storage. The expansive, private backyard completes this property with a detached one-car garage and an additional separate storage shed.

1925 Fairfax Rd, Annapolis

Listing courtesy of RE/MAX Leading Edge. 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:

$550,000

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:

$525,000

$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. PROPERTY IS SOLD AS IS, WHERE IS, AND HOW IT IS. THE POOL MOTOR IS NOT FUNCTIONING. GAS LINE EXISTS BUT IS NOT CONNECTED TO THE GAS COMPANY; THAT IS AN OPTION FOR THE BUYER TO ACTIVATE.

391 Hilltop Ln, Annapolis

Listing courtesy of Deausen Realty. Contact:

$2,395,000

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:

$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:

$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:

$1,300,000

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:

$950,000

Newly and beautifully built in 2026, this stone-accented detached Calvert Model by Dorsey Family Homes offers 3,081 finished square feet and is ideally positioned on a quiet cul-de-sac in desirable Rolling Knolls. Offering a sleek, contemporary design and a bright, airy atmosphere, the home provides a sophisticated foundation for any aesthetic. Abundant natural light complements 9-foot ceilings, a refined mix of hardwood flooring and carpet, recessed lighting, crown molding, wainscoting, and spacious open living areas throughout. // Step inside the impressive two-story foyer, where doors open to a private library or home office. Across the foyer, the elegant formal dining room is illuminated by a statement chandelier. Ahead, the heart of the home unfolds into a spacious open-concept great room, featuring a comfortable family room with a gas fireplace and mantel, a cozy breakfast area with sliding glass doors ready for future outdoor living additions, and the beautifully appointed kitchen. // The gourmet eat-in kitchen is designed for both everyday living and effortless entertaining, featuring a generous center island with breakfast bar seating, upgraded countertops, crisp white cabinetry, stainless steel appliances, and a spacious walk-in pantry. Just off the kitchen, find a powder room and a convenient drop zone providing organized storage near the garage entry. Also located on the main level is a private bedroom or versatile bonus room with a walk-in closet, ideal for guests or multigenerational living arrangements. // Upstairs, four generously sized bedroom suites provide comfortable private retreats. The expansive owner’s suite features an elegant tray ceiling, dual walk-in closets—including an exceptionally large one—and a luxurious ensuite bathroom with a Roman soaking tub, dual-sink vanity, walk-in shower, and private water closet. Two secondary bedrooms share a thoughtfully designed dual-entry full bathroom with dual sinks, while the fourth enjoys its own private ensuite bath. All three secondary bedrooms feature walk-in closets, providing abundant storage. A centrally located laundry room completes the upper level. The walk-out lower-level basement offers a versatile blank canvas, ready to be customized to suit your lifestyle. Work is currently underway to finish the basement and create an additional bedroom, full bathroom, recreation room, and a deck, with all improvements expected to be completed by the end of this year. // Outside, the spacious backyard offers a peaceful, tree-lined backdrop and plenty of room to create your ideal outdoor retreat. The attached two-car garage includes a rough-in for an electric vehicle charging station, while the asphalt driveway provides additional parking.

2175 Glencrest Cir, Annapolis

Listing courtesy of Keller Williams Lucido Agency. Contact:

$649,000

Refined city living meets effortless Annapolis charm in this exceptional end-unit townhome, perfectly positioned in the heart of the Arts District. From this coveted location, some of Downtown Annapolis’ best restaurants, boutiques, Maryland Hall for the Creative Arts, Spa Creek waterfront, scenic trails, playgrounds, and Navy Stadium are all just moments away. The complimentary City Circulator makes exploring the waterfront and City Dock remarkably easy, while convenient access to Route 50 keeps commuting a breeze. Spanning approximately 3,400 square feet over four beautifully finished levels, this sophisticated residence offers an exceptional combination of space, versatility, and custom character. Fresh interior paint creates a crisp, inviting backdrop, while upgraded lighting and carefully selected wallpaper accents in the primary suite and powder room bring an elevated designer aesthetic to the home. The main level is designed for both everyday living and entertaining, with an open-concept floor plan, dramatic ceilings, and an abundance of natural light. The gracious living room centers around a gas fireplace, creating a warm and inviting gathering space. The adjoining kitchen features granite countertops, stainless steel appliances, a substantial center island with seating and storage, and effortless connection to the dining area. Upstairs, the private primary suite offers a serene retreat complete with a generous walk-in closet and beautifully appointed en suite bath featuring a soaking tub, dual vanity, and separate shower. Two additional bedrooms, a full bath, and conveniently located laundry complete the second level. The extraordinary top-floor loft expands the possibilities even further, featuring vaulted ceilings, exceptional storage, a full bath, and a dedicated brand new heating and cooling mini-split system. Equally suited for a second primary suite, guest quarters, home office, creative studio, or comfortable lounge, this versatile space adapts beautifully to a variety of lifestyles. The fully finished lower level adds another dimension to the home with an additional bedroom, full bath, and egress window, offering an ideal private retreat for guests, a home office, recreation space, or extended-stay accommodations. The property also includes two assigned parking spaces, complemented by additional community parking. With its distinctive end-unit setting, impressive scale, thoughtful custom finishes, and enviable proximity to the very best of Downtown Annapolis, this is a home that delivers the quintessential Annapolis lifestyle - with room to live, work, entertain, and enjoy it all. Welcome Home!

101 Carraway Ln, Annapolis

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

$1,125,000

Beautiful colonial home in the perfect Annapolis location on over an acre of private, tree-lined grounds. This charming property offers a peaceful retreat while remaining conveniently close to everything Annapolis has to offer. Enjoy easy access to Route 50 and just minutes from the U.S. Naval Academy, downtown Annapolis, dining, shopping, and more. This beautifully maintained residence features 5 spacious bedrooms and 5 bathrooms (3 full and 2 partial), formal living and dining room offering comfort, flexibility, and room to entertain. Step outside to a large back deck - perfect for entertaining guests or unwinding in a peaceful, private setting. The partially finished basement provides excellent versatility, featuring two bonus rooms, a walk-out entrance, and ample storage space. Gym equipment conveys, providing a ready-to-use home fitness area. A standout feature is the expansive two-level in-law suite with its own private entrance. This flexible space can be configured as a one- or two-bedroom apartment and includes a full kitchen, laundry, living area, and enclosed dining space that can also function as a home office - perfect for extended family, guests, or potential rental income. Additional highlights include: new kitchen, new carpet in the bedrooms and living room, new gutters with screens. Recently replaced 75 gallon water heater, roof, HVAC system. A 240 V Electric vehicle charger in the two-car garage. Ample parking for an RV, boat, and multiple vehicles. The land offers privacy and natural beauty surrounded by protected woodland. The possibility to build an Accessory Dwelling Unit (ADU) on property. Conveniently located near Route 50, this property offers the perfect balance of tranquility and convenience within the sound of colors at the Naval Academy. Agent-owner.

1711 Ritchie Hwy, Annapolis

Listing courtesy of Taylor Properties. Contact:

$950,000

Don’t miss this opportunity to own a stunning Colonial in the highly sought-after Bowen Manor community of Annapolis. Offering over 4,500 square feet of beautifully appointed living space. This is a fantastic opportunity to own one of the biggest, and most private lots in the neighborhood. Perfectly positioned with desirable southeast exposure, this exceptional home is bathed in natural sunlight from morning through early evening. Step inside the grand foyer and discover an open-concept floor plan featuring soaring ceilings, rich Brazilian tigerwood hardwood flooring, elegant architectural columns, custom plantation shutters, and extensive decorative moldings. The formal dining room is designed to impress with a tray ceiling, crown molding, and chair rail, while the adjacent living room is filled with natural light from expansive windows. At the heart of the home is the gourmet kitchen, complete with a large center island with breakfast bar seating, granite countertops, Viking microwave and dishwasher, French door refrigerator, walk-in pantry, and a sun-filled breakfast room with direct access to the expansive rear deck. The adjoining family room showcases a dramatic floor-to-ceiling stone fireplace, creating the perfect gathering space. A private home office and powder room complete the main level. Retreat upstairs to the luxurious primary suite featuring a tray ceiling, oversized walk-in closet, and a beautifully remodeled spa-inspired bath with dual granite vanities, jetted soaking tub, frameless tiled shower with built-in seating and decorative inlay, private water closet, and tray ceiling. Spacious secondary bedrooms provide generous accommodations for family and guests. The fully finished lower level offers exceptional flexibility with a large recreation and entertainment area, fifth bedroom, a renovated full bath, utility/storage room with durable epoxy flooring, and access to the garage. Outdoor living is equally impressive. Relax or entertain on the expansive tiered deck featuring Bose outdoor speakers and smart under-deck lighting, then step down to the custom stone patio overlooking a private, fully fenced backyard surrounded by mature trees and open green space. An 11-zone irrigation system services the front flower beds and both front and rear lawns for effortless landscaping. Thoughtful updates and premium features include a Trane two-stage HVAC system (2024), Hot Water Heater (2026), smart Yale front door lock, dual smart thermostats, Wi-Fi-enabled garage door opener, epoxy garage flooring, 5.1 surround sound ceiling speakers in the living room, GE Smart washer and dryer (2021), and a professionally soft-washed exterior completed in 2026. Enjoy an unbeatable location just minutes from Routes 50 and 97, Mike's Crab House, South River marinas, Annapolis Town Center, Festival at Riva, Annapolis Mall, multiple grocery stores, restaurants, and more. Outdoor enthusiasts will appreciate being just minutes from Riva Park, Quiet Waters Park, and Davidsonville Park. Luxury finishes, modern smart-home technology, an exceptional outdoor living experience, and one of Annapolis' most convenient locations combine to make this remarkable Bowen Manor residence truly one of a kind. This home won't last long!

206 Bowen Ct, Annapolis

Listing courtesy of Redfin Corp. Contact:

$1,295,000

PRICE HAS BEEN REDUCED!! Rare Opportunity to own a newer home tucked away on a private cul-de-sac just a short stroll from everything Downtown Annapolis has to offer. Completed in 2022, this exceptional home showcases top of the line finishes throughout. Designer kitchen with Quartz countertops, custom cabinetry and high end GE Cafe appliances. Wide Plank hardwood floors throughout the main and upper levels. 9 foot ceilings and custom moldings. Recessed lights throughout the home. Low Maintenance Hardie Plank siding and Anderson Windows. Main level has an open floor plan with office area perfect for those that work from home. Upper level features 4 generous sized bedrooms. Primary Bedroom has cathedral ceilings, massive his and her walk in closets. Lower level is finished with indestructible Luxury Vinyl Plank floors. In the lower level there is a room perfect for a gym or 5th bedroom (there is an egress window). The .25 acre lot has community space next to it that provides extra yard space for kids to use. 2 Car attached garage with a rough in for EV Charger. Sellers recently installed Solar Panels. Energy costs are VERY minimal. Terrapin Station is a prime location. The Navy Stadium is just around the corner. Walkable to Historic Annapolis, US Naval Academy and tons of restaurants. Steps from the Poplar Path which has numerous playgrounds and the Michael Busch Annapolis Library off it. Come live the Annapolis lifestyle!

111 Ellershaw Ct, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

$750,000

2.625% Assumable FHA loan! Significant Price Improvement! Priced to sell, incredible value and opportunity. Excellent Condition. Welcome to this beautifully maintained custom built Tudor Style home in this small coastal community. NO HOA!! Pride of ownership shows! With a primary suite on the main level and another primary suite on the upper level, this home is perfect for Multi-Generational Living and Accessibility! The upper level features 3 spacious bedrooms and 2 full baths; the main level has 1 large bedroom with a full bath and walk-in shower; and the lower level has another full bath and several areas to make additional bedrooms. The huge 1,100 sqft finished lower level has multiple rooms including a large rec room that can fit a pool table, games and a bar area; plus a family room or theatre room and private entrance! There is even space for a kitchenette! There are so many possibilities with this extra space including an apartment or in-law suite! The home is filled with natural light and scenic views throughout. Situated on almost a half of acre and only 2 blocks to the Chesapeake Bay! The lush backyard is fully fenced in and ready for entertaining and evening dinners on the updated trex deck! The lot next to the home is a county preserved wooded lot that offers privacy and attracts wildlife. Oyster Harbor offers the best of Coastal Maryland living—just minutes from historic downtown Annapolis, top-rated restaurants, shopping, and commuter routes. The home has been well cared for and maintained; only two owners since it was built! Recent updates include: HVAC, water heater, main level LVP floors that are very durable, trex deck and renovated front porch with tile, custom plantation shutters, renovated primary suite and luxury full bath, front load w/d, professionally cleaned, professionally landscaped, backyard drainage system...and more! Sellers are MOTIVATED and ready for another family to make this their home! MOVE-IN READY AND A MUST-SEE! You won't find many homes with this lot size and location for this price. Don't miss this great opportunity! Schedule your showing today.

3280 Arundel On The Bay Rd, Annapolis

Listing courtesy of The KW Collective. Contact:

1979 Baltimore Annapolis Blvd, Annapolis

$3,000,000

A truly extraordinary opportunity awaits in one of Annapolis' most coveted waterfront locations. Situated in the historic Ferry Farms neighborhood, 1979 Baltimore Annapolis Boulevard is one of only thirteen homes positioned directly across the Severn River from the U.S. Naval Academy, offering uninterrupted panoramic views that have captivated generations. Imagine enjoying the Blue Angels soaring overhead each May from your own front lawn or dock—an experience few will ever call home. Rich in architectural character, the residence showcases the craftsmanship and charm of its era, including original hardwood floors, a classic wood-burning fireplace, vintage kitchen, inviting sunroom, screened porch, and period details that create a warm sense of history. The home's generous square footage spans three levels, blending the original residence with a substantial 2015 addition that expanded both its living space and functionality while preserving its unique personality. For buyers with vision, this property presents an exceptional opportunity to create a landmark waterfront residence tailored to today's lifestyle. Architectural renderings, renovation plans, a professional landscape design, and contractor cost estimates are available to help bring that vision to life, allowing the next owner to build upon an already remarkable foundation. The original home includes a main-level bedroom and full bath, while the upper level offers four additional bedrooms, including a primary suite with a private balcony overlooking the water. The 2015 addition introduced a spacious three-car garage, an expansive loft, and an additional bedroom perfect for guests, a home office, or a studio. A future bathroom has already been considered, with a rough-in located beneath the connecting section of the second floor. The lower level offers even more possibilities, featuring a second wood-burning fireplace, laundry area, utility space, and an impressive workshop with soaring ceilings and direct access to the garage and backyard—ideal for craftspeople, hobbyists, or future finished living space. Outside, the waterfront amenities are equally compelling. The private deep-water pier and bulkhead, completed in 2003, feature approximately 10 feet of water depth, a 40,000-pound boat lift, a 15,000-pound lift, and two 1,500-pound personal watercraft lifts, making this an outstanding property for serious boaters. A built-in outdoor barbecue and expansive waterfront setting invite effortless entertaining and relaxed evenings watching sailboats drift past the Academy. Properties of this caliber, location, and potential rarely become available. Whether thoughtfully restoring its historic character, executing the available renovation plans, or creating a legacy waterfront estate of your own design, this is a once-in-a-generation opportunity to own an irreplaceable piece of Annapolis waterfront in one of its most prestigious and tightly held neighborhoods.

1979 Baltimore Annapolis Blvd, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

$2,999,900

Seller financing available — an exceptional opportunity to own a distinguished Annapolis waterfront estate. Beautifully situated on 1.86 private acres in the prestigious Downs on the Severn, 1486 Downham Market offers a rare combination of protected deep water, gracious living and the extraordinary pleasures of life along the Severn River. With captivating water views, an impressive private pier and more than 5,200 square feet of beautifully appointed living space, this exceptional property offers a lifestyle to be enjoyed for generations. For the discerning boating enthusiast, the waterfront is truly remarkable. Positioned at the mouth of Clements Creek, a naturally protected harbor, the property features an impressive 180-foot private pier with three slips, 50-amp shore power, reinforced pilings ready for lifts, full riparian rights and approximately 11 feet of mean low water. Whether enjoying an afternoon on the Chesapeake Bay, an evening cruise along the Severn or the simple pleasure of having your yacht just steps from home, this setting is nothing short of extraordinary. Inside, walls of glass frame beautiful water views and fill the residence with natural light. Soaring ceilings, rich hardwood floors, elegant finishes and a striking two-sided stone fireplace create an atmosphere of warmth and sophistication. The beautifully appointed gourmet kitchen, featuring commercial-grade appliances, gas cooking and generous gathering spaces, is equally suited for intimate evenings and memorable celebrations. Imagine Thanksgiving overlooking the water, Christmas beside the fireplace and summer evenings entertaining friends on the expansive decks as boats make their way home. Here, every season offers something beautiful to enjoy. The luxurious waterfront primary suite provides a peaceful sanctuary with its own sitting room, fireplace, custom walk-in closet and beautifully appointed spa bath. Generously proportioned additional bedrooms welcome family and guests, while the finished walk-out lower level offers a recreation room, wet bar, wine storage, fitness room, fifth bedroom and full bath. A glass-enclosed sunroom overlooking the water provides another inviting place to relax and appreciate the surroundings. Outdoor living is equally exceptional. Expansive multi-level decks invite elegant entertaining, leisurely dining and quiet mornings overlooking the harbor. Nearly two acres of beautifully landscaped grounds offer privacy and serenity within one of Annapolis' most desirable waterfront communities. Recent improvements, including a new septic system and advanced whole-house water treatment with reverse osmosis and ultraviolet purification, provide additional comfort and peace of mind. Residents of Downs on the Severn enjoy access to two private marinas, a waterfront clubhouse, swimming pool, tennis and pickleball courts, all conveniently located near Historic Annapolis, wonderful restaurants and shopping, and major commuter routes to Baltimore and Washington, D.C. A magnificent deep-water setting, an extraordinary private pier and a beautifully appointed home designed to embrace the waterfront lifestyle. At 1486 Downham Market, the beauty of the Severn River is not simply a view. It is a way of life.

1486 Downham Market, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

$1,998,000

5 Beds ⋅ 7 Baths

Welcome to this exceptional custom-built estate set on 3.1 acres in Wyatts Hill community. Offering three finished levels of thoughtfully designed living space, this five-bedroom, seven-bathroom home combines timeless architecture, modern updates, and resort-inspired outdoor living. A grand two-story foyer welcomes you with a sweeping curved staircase and soaring ceilings. The main level is designed for both everyday living and entertaining, featuring a formal dining room, private office, dramatic two-story family room with a fireplace, and a sunroom connected by French doors that fills the home with natural light. The gourmet kitchen serves as the heart of the home with an oversized center island, custom cabinetry, granite countertops, a spacious breakfast area, and a butler’s pantry, creating an ideal space for gatherings large and small. The main level also features a spacious primary suite with an en-suite bath, providing flexibility for a variety of living arrangements. An additional office, laundry room, and powder room complete the main level. Upstairs, a second primary suite offers a private retreat with a sitting area and en-suite bath. Three additional bedrooms each feature their own private en-suite bathrooms, providing comfort and privacy throughout the upper level. The walkout lower level expands the home’s living and entertaining space with a large recreation room, second kitchen, half bath, and abundant storage. Completed in 2023, the backyard was transformed into an exceptional outdoor living space featuring a heated saltwater pool, expansive patio, outdoor fireplace, and a fully equipped outdoor kitchen designed for entertaining and enjoying an outdoor lifestyle. Recent improvements include a new roof (2025), two new HVAC systems (2022), new wood front and garage doors, a Tesla EV charger, and a lawn irrigation system. Located in the desirable Wyatts Hill community with no HOA, this home offers convenient access to Historic Annapolis, BWI Airport, Fort Meade, Baltimore, Washington, D.C., and major commuter routes including I-97 and Route 50.

1614 Annesley Ct, Annapolis

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

$4,600,000

140 SPA DRIVE YOUR HOME. YOUR MARINA. YOUR ANNAPOLIS. A PRIVATE 14-SLIP MARINA IN YOUR OWN BACKYARD—ON SPA CREEK IN ANNAPOLIS. An exceptionally rare opportunity to own a waterfront residence with its own 14-slip marina on one of Annapolis’ most treasured waterways. Set along approximately 90 feet of Spa Creek waterfront, 140 Spa Drive combines an extraordinary boating lifestyle with a distinctive total five-bedroom residence, panoramic water views and dockside parking—all in a residential setting. For the serious boater, yachtsman or family who wants room for more than one boat, this is a property unlike almost anything else in Annapolis. Step from your home to your marina, welcome friends and family by water, or simply enjoy watching life on Spa Creek from nearly every level of the residence. The Nantucket-inspired home is designed around the water, with walls of glass and more than 100 windows filling the interiors with natural light and capturing sweeping Spa Creek views. Multiple balconies and an expansive waterside terrace create wonderful spaces for entertaining, dining outdoors or simply enjoying the ever-changing waterfront. The home offers approximately 5,095 square feet of finished living space, including approximately 3,295 square feet above grade and an additional approximately 1,800-square-foot finished lower level. Five bedrooms, generous living spaces and flexible guest or in-law accommodations make the property equally suited to everyday living and extended family gatherings. Outside, the marina becomes an extension of the home. Fourteen slips, approximately 90 feet of waterfront, dockside parking and a waterside workshop create an exceptional setting for those whose life revolves around the water. Located at the protected upper reaches of Spa Creek, the property is just a few minute boat ride from downtown Annapolis Harbor. This isn’t simply a waterfront home. It’s an opportunity to own an Annapolis boating lifestyle that would be extraordinarily difficult to duplicate. 140 Spa Drive — where your backyard is your marina.

140 Spa Dr, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

$2,495,000

Life takes on a different pace in Oakwood, where the calm waters of Fishing Creek and the South River provide an idyllic backdrop and effortless access to the Chesapeake Bay. With 93 feet of shoreline, a private pier with multiple slips, and a substantial 25,000-pound boat lift, this property is perfectly suited for boating enthusiasts and those who appreciate the beauty and tranquility of the Chesapeake lifestyle. Designed for both everyday comfort and effortless entertaining, the home offers an inviting open floor plan with seamless flow between the gourmet kitchen with center island, sunroom, soaring two-story living room, and adjacent family room. Walls of windows frame picturesque water views and fill the home with natural light. A versatile main-level room with an adjoining full bath provides ideal space for guests, a private office, or flexible living needs. Upstairs, the spacious primary suite serves as a peaceful retreat with abundant windows capturing the ever-changing waterfront scenery, a walk-in closet, and an ensuite bath featuring dual vanities, a large shower, and a relaxing soaking tub. Two additional bedrooms share an ensuite bath and a fourth bedroom provides plenty of space for family and friends. The expansive space above the garage has been transformed into a fun Margaritaville-inspired bar and game room complete with a full bath. This exceptional area offers endless possibilities and could easily become a second primary suite, private guest quarters, or an in-law suite. Outside, multiple entertaining spaces invite gatherings with family and friends while the lush lawn gently transitions to the water's edge. Whether hosting summer celebrations, launching a boat for a day on the Bay, or simply unwinding as the sun reflects across Fishing Creek, this property offers a lifestyle that feels like a vacation every day. A side-entry two-car garage and spacious driveway complete this exceptional waterfront offering in one of Annapolis Neck's most desirable communities. Welcome Home!

3733 Thomas Point Rd, Annapolis

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

$1,119,000

Escape to your New Sanctuary on a 1.17 Acre Lot. Welcome to the Birch Model, one of our premier homes designed for those who desire the best in space, style, and comfort. This home offers everything you need for luxurious living. 5 Bedrooms: Perfect for large families or those who enjoy hosting guests, each bedroom is spacious and thoughtfully designed. 4.5 Bathrooms: Enjoy the convenience of four full bathrooms and a powder room, providing ample space and privacy for everyone. Extra Storage Space: Keep your home organized with plenty of storage throughout, including a dedicated storage room! Walk-In Pantry: A spacious pantry provides ample storage for all your kitchen essentials and more. Butler’s Bar: Entertain in style with a dedicated butler’s bar, perfect for serving drinks and hors d’oeuvres. Dedicated Office: An ideal space for working from home, studying, or managing household affairs. Open and Inviting Layout: The Birch Model features a seamless flow between the kitchen, dining, and living areas, perfect for both everyday living and entertaining. Luxurious Owner’s Suite: Retreat to your private haven, featuring a spacious bedroom, a spa-like en suite bathroom, and a large walk-in closet. Optional Upgrades and Customizations: Personalize your Birch Model with a variety of finishes, fixtures, and additional features to make it truly your own. The Birch Model offers unparalleled luxury and space, making it the perfect home for those who want it all. Discover what makes this home truly exceptional. Contact us today to schedule a tour and learn more about available customization options!

1353 Yorktown Rd, Annapolis

Listing courtesy of The Pinnacle Real Estate Co.. Contact:

$1,549,000

Welcome to 202 Wardour Drive! This classic 1940 Dutch Colonial offers timeless character, generous living space, and an unbeatable Annapolis location. Situated on a quarter acre lot with large front yard, the south facing location ensures sunny days ahead! Located in the elegant Wardour community which reflects the naturalistic style of its designer, Frederick Law Olmstead, Jr, with its mature trees, meandering roads and preserved open spaces that foster community connection. Inside, the home features five bedrooms, two bathrooms, gorgeous oak floors (recently refinished in 2026), fireplace, bright sun-porch and large 12x 32 back deck. The south-facing orientation fills the home with natural light, creating a bright and cheerful atmosphere throughout. Recent improvements include freshly painted interior and exterior spaces, a newer roof approximately four years old, new porch benches, and a beautifully installed brick paver sidewalk that enhances the home’s curb appeal. A long driveway and rear detached garage provide ample parking and storage. Residents benefit from access to seven community beach areas and a shaded walking trail traversing the neighborhood, that provide a tranquil retreat for adults and a natural wonderland to explore. Conveniently located within walking distance of the local elementary school, Navy Stadium, Annapolis Street shopping and dining, Historic Downtown Annapolis and offers easy access to Rt. 50 for commuters. With classic architecture, spacious interiors, abundant natural light, and an exceptional in-town location close to everything Annapolis has to offer, this is a rare opportunity to own in one of the area’s most beloved neighborhoods. Schedule your private tour today!

202 Wardour Dr, Annapolis

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$7,775,000

5 Beds ⋅ 7 Baths

Now offered at $7,775,000, this 3.1-acre direct-waterfront estate on the Chesapeake Bay represents an incredible luxury buying opportunity. Masterfully crafted by ABS Architects and built in 2019, reproducing this residence of over 10,000 total square feet today would carry a significantly higher price tag and would mean enduring a daunting 3-year build time alongside unpredictable construction costs. Sited on a rare, south-facing lot with 210 feet of private shoreline in the exclusive Maidstone Farm community, the property captures commanding, panoramic views from nearly every principal room with immediate kayak and paddleboard launch access right from your spacious waterfront lawn. Designed as a generational gathering spot for holidays and special occasions, the home blends grand architectural details—including 10-foot ceilings, coffered ceilings, and extensive molding—with a layout built for world-class entertaining. Outdoor living centers around a resort-style, heated saltwater pool, waterside verandas, and covered porches that seamlessly transition indoors. At the heart of the residence is a chef's dream kitchen featuring two oversized islands, Eucalyptus cabinetry, a La Cornue range, and dual Sub-Zero refrigerators. The home features a private primary suite with a barrel-vaulted ceiling, sitting area, sweeping views, and an oversized walk-in closet, alongside 4 additional custom-tiled ensuite bedrooms. Designed with provisions for a future elevator, the layout also includes a four-car garage and a versatile finished space above complete with a full bath, perfect for an exercise room or home theater. For ultimate boating convenience, the estate includes ownership of a protected, deep-water pier (6–7' MLW) with a 10,000-lb boat lift just a short, three-minute drive away on Burley Creek—giving you wide-open bay vistas alongside protected deep water. Beyond the 7,105 finished above-grade square feet, a 3,700-square-foot unfinished lower level features high ceilings, offering an incredible footprint ready to be transformed into your own customized space. Complete with 6-zone HVAC, spray foam insulation, a full-home Control4 automation system, and a commercial-grade Kohler backup generator with a 2,000-gallon propane tank, this turnkey estate is located just minutes from downtown Annapolis.

2035 Maidstone Farm Rd, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

$925,000

Rare waterfront redevelopment opportunity in Annapolis. The existing structure is a complete shell and requires a full renovation or rebuild. Ideal for investors, builders, or buyers looking to design and construct a custom waterfront home from the ground up. Located along the protected waters of Oyster Cove, the property includes a deep-water pier and boat house. The existing footprint and favorable waterside placement offer strong potential to maximize views and overall design. Convenient access to the Chesapeake Bay and close proximity to Historic Downtown Annapolis by both land and water. Enjoy boating, sailing, and easy access to surrounding waterfront destinations throughout the region. Property is being sold strictly as-is. A unique opportunity for those ready to take on a full redevelopment project in a prime waterfront setting.

1254 Washington Dr, Annapolis

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

$9,998,000

5 Beds ⋅ 6 Baths

NEW PRICE — $9,998,000. A rare opportunity to acquire an extraordinary Annapolis waterfront estate, now thoughtfully repositioned for today’s discerning buyer. Set along 168' of Spa Creek waterfront, this approximately 6,000 SF residence is privately positioned within an exclusive enclave of just three homes. The private deep-water dock offers approximately 8' MLW and accommodates a 60–70' sailboat or yacht with wide beam. Cruise to City Dock and downtown restaurants in minutes, or enjoy panoramic water and unobstructed Annapolis skyline views from home, including front-row views of the Blue Angels, fireworks and annual boat parade. The heated saltwater pool, expansive Ipe deck and beautifully landscaped grounds create exceptional waterfront entertaining. Meticulously maintained and extensively renovated by Pyramid Builders, the architecturally distinctive residence features a dramatic marble foyer, floor-to-ceiling windows, solid wood doors, rich stained black oak flooring and two striking gas fireplaces. The sophisticated white kitchen features Sub-Zero refrigeration, a eight-burner Viking cooktop, high-gloss Premier cabinetry and Neolith porcelain countertops, complemented by designer lighting and a striking floating staircase. A private speakeasy with a custom marble-topped bar creates an intimate setting for cocktails and entertaining. The residence offers 4–5 bedrooms and 5 full and 1 half baths, including a first-floor bedroom suite. A two-car garage, generous parking and private pier complete this exceptional Murray Hill waterfront offering. Enjoy deep-water boating, resort-style outdoor living, sophisticated entertaining and downtown Annapolis—all from one extraordinary private setting.

8 Spa View Cir, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

$2,295,000

This exceptional Historic District home combines the charm of a classic Annapolis address with a substantial 2026 renovation in all the right places. A stunning new kitchen, custom wet bar, expanded pantry area, completely reimagined third floor, new full bath, and New HVAC system bring modern function and style to this timeless home. Water access is at the end of the block, Acton's Cove waterfront park is around the corner, and City Dock, Main Street, restaurants, shops, and the Naval Academy are all within easy walking distance. Easy parking on quiet Market Street. The new kitchen features custom cabinetry, Taj Mahal quartzite countertops, ceramic tile backsplash, unlacquered brass hardware, designer lighting, and a full suite of GE Monogram appliances. The expanded pantry area offers plenty of storage, a separate freezer, and ice maker, while the custom wet bar includes reeded glass cabinetry, brass detailing, a dedicated sink, and generous storage for entertaining. A full-width screened porch spans the front of the home, while 10-foot ceilings, original architectural details, and multiple gathering spaces create warmth and character throughout. The main level includes a paneled office, formal living and dining rooms, and a casual family room that opens to the eat-in kitchen and rear patio with gazebo. Seasonal water views can be enjoyed from several rooms. Upstairs, the primary suite offers winter water views, dual organized closets, and an updated bath. A 2nd bedroom with hall bath and laundry room are located on this level. The 3rd floor has been completely reimagined to create 3 additional rooms with built-in storage and a beautiful new full bath featuring classic finishes, custom millwork, and quartz countertops. A rare opportunity to enjoy the character of Historic Annapolis with the benefits of a major recent renovation, all tucked on a quiet street in the heart of the Historic District. Water access is just steps away, downtown Annapolis is an easy walk, and everyday convenience is rarely this effortless.

83 Market St, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

$1,049,000