Annapolis MD 6+ Bedroom Real Estate, Homes, Condos for Sale

Welcome to a truly exceptional offering in St. Margarets Landing! Prime location meets turn-key design on a coveted corner lot, strategically hand-selected by the original owner for its sunlit openness, minimal pass-through traffic, and immediate gate access to neighborhood walking paths. Inside, real hardwood flooring spans the main level, upper level hallway, and all staircases. Spanning 6 total bedrooms and 4.1 baths, the flexible layout is designed for modern multi-generational living with two Primary Suite options —including a main-level primary featuring soaring vaulted ceilings, and an upper-level primary suite alongside 3 additional spacious bedrooms. NOTE FOR SHOWINGS: Tax records incorrectly reflect the finished lower-level square footage; the basement actually features an expansive 900 sq. ft. in-law / multi-generational suite with an outside private entrance, designed for complete flexibility, along with two massive dedicated storage areas (see floor plans in photos). The lovely main level flows seamlessly through a formal living room, great room with stone gas fireplace, breakfast area, large kitchen with plenty of counter space, formal dining area, laundry room, and garage entrance. Dual sliding glass doors off of the breakfast area lead to your outdoor retreat: a generous back deck and paver patio overlooking a fully vinyl-fenced backyard wrapped in mature, privacy-enhancing arborvitae trees and served by a 9-station irrigation system. Peace of mind is built right in, anchored by a roof replaced within the last five years and a full-home Generac backup generator that kicks on automatically in 30 seconds. Located in the top-rated Broadneck School District, 605 Lighthouse Landing also affords rapid access to premier private education including St. John the Evangelist, Severn School, The Key School, Indian Creek, and the U.S. Naval Academy. An ideal commuter hub close to major employers like Fort Meade, NSA Headquarters, defense tech corridors (Lockheed Martin, Northrop Grumman, Booz Allen), Luminis Health Anne Arundel Medical Center, and downtown Annapolis.

605 Lighthouse Landing Ln, Annapolis

Listing courtesy of Douglas Realty LLC. Contact: (866) 987-3937

$1,080,000

6 Beds ⋅ 5 Baths

Prepare to be absolutely wowed. Nestled in one of Annapolis's most sought-after communities, this stunning six-bedroom, four-and-a-half-bathroom Colonial has been completely and thoughtfully renovated from top to bottom, delivering a rare combination of timeless elegance, modern luxury and exceptional space across three beautifully finished levels. Step inside and immediately feel the difference. Rich hardwood floors flow throughout the entire main level, complemented by exquisite custom moldings and wainscoting that speak to the level of craftsmanship and attention to detail found at every turn. The main level offers an effortless and inviting flow designed for both everyday living and grand entertaining: a private home office, a gracious dining area, two distinct living spaces and a cozy gas fireplace. And then there's the kitchen. The ultimate chef's kitchen. Anchored by a breathtaking commercial-grade 48-inch GE Monogram gas range- GE's highest tier of luxury appliances- and boasting five ovens, this is a space that serious home cooks and entertainers dream about. No detail was overlooked, no compromise was made. This kitchen doesn't just function beautifully- it commands the room. Step outside to the beautiful deck, perfectly positioned for morning coffee, al fresco dining, or evening unwinding after a night of entertaining. Upstairs, the custom moldings and wainscoting continue, lending a sense of refined consistency and elegance throughout. Retreat to a truly spectacular primary bedroom sanctuary- a spacious, serene haven with its own additional living space, offering the kind of personal escape that makes coming home the best part of every day. Three additional bedrooms complete the upper level, including a private en suite and a generous full bathroom for guests or family. The lower level delivers even more, with two additional bedrooms and expansive recreational space that adapts beautifully to your needs- a home gym, media room, playroom, or guest retreat. The two-car garage adds everyday convenience and storage, while outside, the pergola brings it all together- a stunning, dedicated entertaining space that elevates outdoor living to match the luxury found within. Located just minutes from historic downtown Annapolis, premier dining, marinas, and major commuter routes to DC and Baltimore, 214 Bowen Court isn't just a home- it's a lifestyle.

214 Bowen Ct, Annapolis

Listing courtesy of Engel & Volkers Annapolis. Contact: (443) 292-6767

$2,650,000

6 Beds ⋅ 6 Baths

Annapolis Stunning Coastal Colonial Waterfront Retreat where every day feels like a vacation. Perfectly positioned on the tranquil waters of the Chesapeake Bay tributaries, this extraordinary waterfront residence at 529 Lee Circle offers an exceptional blend of sophisticated coastal design and effortless indoor-outdoor living. Privately nestled among mature trees, the home enjoys a peaceful setting with panoramic water views, a private pier, a boat house and a floating dock, creating the ultimate Annapolis waterfront retreat. The impressive rear elevation is designed to embrace the waterfront lifestyle, featuring expansive walls of glass that flood the interiors with natural light while framing picturesque water views from nearly every level. Multiple outdoor living spaces—including a spacious waterside deck, an upper-level balcony, and an expansive lawn leading to the 114 feet shoreline—provide the perfect backdrop for entertaining or relaxing while enjoying spectacular sunsets. The boat house with lift, private pier, and protected water dockage offer immediate access to boating, paddleboarding, kayaking, and all the Chesapeake Bay has to offer. Whether departing for a day on the water or enjoying quiet evenings along the shoreline, this property delivers an unmatched waterfront experience. Architecturally, the home combines classic coastal elegance with contemporary comfort. Soft gray siding, crisp white trim, multiple gables, and oversized windows create a timeless façade that complements its natural surroundings. The residence offers approximately 6,000 square feet of living space with two owners suite (one on the main level), generous entertaining areas, multiple fireplaces, and luxurious accommodations designed for both everyday living and grand-scale gatherings. The home was originally built in 1965. In 2016 it went through a complete, down-to-the-studs renovation and expansion to the creation of stunning luxurious waterfront home. Custom-Built by Architect Teresa Todd and Timberlake Homes into a 6-bedroom and 5.5-bathroom residence. Located within the sought-after Hillsmere Shores community, residents enjoy a coveted Annapolis lifestyle with access to a private beach, marina, community pool, playgrounds, and convenient proximity to Historic Downtown Annapolis, waterfront dining, yacht clubs, and the U.S. Naval Academy. This is more than a waterfront home—it is a private Chesapeake Bay sanctuary where luxury, recreation, and timeless coastal beauty come together in one exceptional offering.

529 Lee Cir, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686

$499,900

6 Beds ⋅ 2 Baths

Welcome Home! This spacious 6-bedroom Split Foyer in the highly sought-after Cape St. Claire community offers Chesapeake Bay views from a prime location directly across the street from the water. With 3 bedrooms on the main level and 3 additional bedrooms on the lower level, this home provides exceptional flexibility for multi-generational living, guests, home offices, or growing households. The main level features a bright living room that flows into the dining area, kitchen, and a generously sized family/sunroom, creating an ideal space for both everyday living and entertaining. Two full bathrooms, abundant storage, and a functional layout offer comfort and convenience throughout. The lower level includes three additional bedrooms, a laundry room, storage room, and a large workshop with rear exterior access, perfect for hobbies, a home business, fitness space, or extra storage. Enjoy the unmatched amenities of Cape St. Claire, including community beaches, a fishing and crabbing pier, boat ramp, marina, playgrounds, and more. Conveniently located near shopping, dining, and everyday necessities, and just minutes from Downtown Annapolis. Commuters will appreciate the easy access to Route 50, I-97, Washington, D.C., Baltimore, and Fort Meade. A rare opportunity to enjoy Bay views, outstanding community amenities, and a fantastic location while creating the home of your dreams!

1247 River Bay Rd, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4107407100

$1,895,000

8 Beds ⋅ 6 Baths

Set on nearly two serene acres, this stately brick-front colonial commands attention with timeless curb appeal. Inside, a formal living room and a separate office or study offer refined spaces for quiet pursuits, while the expansive great room and adjoining den are connected by a dramatic double-sided fireplace, one of four throughout the home. The partially open layout flows with intention, suited to entertaining on a grand scale or gathering in comfort. A grand formal dining room is framed by a wall of windows overlooking the side garden, and the renovated cook's kitchen impresses with stainless appliances, dual wall ovens, a 36" professional series gas cooktop, and an oversized island. A separate breakfast area and a large rear deck extend the living space outdoors, overlooking the grounds and swimming pool. Upstairs, five bedrooms include an extraordinary owner's suite with a gas fireplace, walk-in closet, and a beautifully renovated bath with soaking tub. The lower level offers exceptional versatility with three additional bedrooms, a large living area or recreation room, two full baths, a renovated kitchen, and separate access, ideal for guests or extended family. A three-car garage completes the residence. Brice Manor resides within the Meadows Community, known for its oversized lots, lush lawns, and heritage trees. Tree-canopied streets and award-winning Blue-Ribbon schools define this secluded enclave, moments from the Severn River with easy access to West Annapolis, Eastport, and historic Annapolis.

234 Meadowgate Dr, Annapolis

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

$989,000

6 Beds ⋅ 4 Baths

Ready to move in and designed for modern living, this beautifully updated Germantown-Homewood home features six bedrooms plus flexible living spaces that can evolve with your needs. Whether used as home offices, guest accommodations, playroom, a fitness room, media room, or hobby space, every room offers exceptional versatility in one of Annapolis' most walkable locations. With over 3,100 finished square feet, the home has been thoughtfully updated with significant system improvements, including a new roof, HVAC, boiler, water heater, and natural gas line. A fully renovated walkout lower level with a kitchenette and full bath provides exceptional flexibility for guests, recreation, or additional living space. These extensive updates offer peace of mind while preserving the home's timeless character and charm. The covered front porch is made for morning coffee, evening conversations, and neighborhood gatherings, while parking for approximately eight vehicles makes entertaining effortless. Location is where this home truly shines. Nestled in the heart of Germantown-Homewood next to Busch Library and steps from the Poplar Trail, you'll enjoy an easy stroll to Ceremony Coffee, Black Market Bakers, Carlson's Donuts, Paul’s Cafe, West Street, neighborhood restaurants, and downtown Annapolis. It's also the perfect home base for Navy football Saturdays, Blues games, and hosting family and friends visiting Annapolis. Close to major highways for commuters. Originally built in 1938 as the historic Gables Tourist Home, the property still carries charming reminders of its past—including the numbered bedroom doors—while offering all the comforts of modern living. With no HOA and eligibility for the Admiral Heights Pool, this is a rare opportunity to enjoy space, character, and one of Annapolis' most walkable & accessible neighborhoods.

1422 West St, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686

$12,950,000

6 Beds ⋅ 9 Baths

Imagine arriving home each day to a place where the pace slows, the views stretch for miles, and every amenity for recreation, relaxation, and entertaining is right outside your door. Tucked away along the Chesapeake Bay, this extraordinary waterfront retreat offers a lifestyle that few properties can match, a private oasis where luxury and nature exist in perfect balance. Originally constructed by the renowned Pyramid Builders and later transformed through an extraordinary $7 million top-to-bottom renovation, also completed by Pyramid Builders, the estate has been reimagined to an uncompromising standard. Every space, finish, and amenity was thoughtfully designed and curated to create a residence that is as functional as it is beautiful, blending timeless craftsmanship with modern luxury. State of the art features include the Crestron Home Automation and integrated Lutron lighting systems while the modern luxuries entail top of the line Miele appliances including a built-in coffee maker, microwave and convection oven, BlueStar range, radiant heated floors in all bedroom bathrooms and much more. Here, days can begin with coffee overlooking the pond and its abundant wildlife, followed by a swim in the heated saltwater pool, a match on the tennis or pickleball court, a workout in the gym, or a stroll down to the sandy beach. Evenings are spent gathered with family and friends around the pool and hot tub, watching the game on the hydraulic television that rises from the landscape, enjoying a glass of wine from the tasting room, or simply taking in the stars above the Bay. The ever-changing waterfront scenery, southern exposure, and remarkable sense of privacy create a backdrop that feels more like a luxury resort than a private residence. Designed for those who believe home should be a destination, the property offers an incredible collection of indoor and outdoor amenities rarely found in a single estate. Tennis, pickleball, basketball, a climbing wall, playground, in-ground trampoline, expansive lawns, sandy beach, pond with fountain, indoor racquetball court with basketball and volleyball capabilities, golf simulator, game room, fitness center, indoor lap pool, infrared sauna, wine tasting and cellar area, and countless spaces to gather ensure there is always something to enjoy for every generation. The residence itself is beautifully designed and thoughtfully appointed, with spacious living and entertaining areas, a wraparound screened porch that embraces the waterfront setting, private ensuite bedrooms throughout, and a dedicated guest or in-law suite that welcomes family and friends in comfort and style. Abundant storage, an attached two-car garage, and a detached garage with additional space for vehicles, golf carts, recreational equipment, and storage provide the functionality expected of a property of this caliber. What makes this estate truly special is not simply the remarkable list of amenities—it is the feeling it creates. The extraordinary combination of peace, beauty, privacy, and convenience is increasingly difficult to find. Just minutes from Annapolis, yet seemingly a world away, this is the kind of property where children spend their days outdoors, guests never want to leave, and every sunset reminds you why you chose to call it home. A rare opportunity to own a true Chesapeake Bay waterfront compound where every day feels like a vacation, every detail has been thoughtfully considered, and the lifestyle is every bit as exceptional as the home itself. Welcome Home!

2045 Maidstone Farm Rd, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600

$1,295,000

6 Beds ⋅ 6 Baths

Set on a private .75-acre lot backing to the 14th hole of the Navy Golf Course, this exceptional home is located in a prime Broadneck School District location just minutes from Downtown Annapolis. The backyard is what truly sets this property apart. With a screened-in porch, fire pit, multiple seating areas, basketball and pickleball court, full playground, and expansive lawn, it feels more like your own private park than a typical backyard. Whether hosting a crowd, watching the kids play, or enjoying a quiet evening outdoors, this is really a magical setting. Inside, 9-foot ceilings, generous room sizes, custom finishes, and abundant natural light create comfortable living spaces throughout. A main-level bedroom and full bath offer flexibility for guests or multi-generational living. The walk-out lower level includes a family room, bar, office, gym, and dedicated playroom. Additional features include Hardiplank siding, a two-car garage, and ample side parking for several cars in the driveway. A voluntary Pendennis Mount HOA of just $50 per year provides water access on the Severn River near the Severn Inn. Homes offering this combination of outdoor space, recreation, privacy, and convenience are few and far between.

1903 Baltimore Annapolis Blvd, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686

$1,850,000

6 Beds ⋅ 5 Baths

Located in Annapolis' Historic District, this 4 story home offers a rare opportunity to own a spacious residence within walking distance of the water, City Dock, shops, restaurants, and local attractions. Featuring 6 bedrooms and 4.5 bathrooms, the home is filled with original character, including hardwood flooring and original doors throughout. The oversized living room features a gas fireplace and provides plenty of space for gathering and entertaining. Just off the kitchen, a deck overlooks the backyard with walkways, established gardens, and a fish pond, creating a peaceful outdoor setting in the heart of downtown Annapolis. A welcoming front porch with a porch swing offers another place to relax and enjoy the neighborhood. With central air conditioning, three finished levels, and ample parking, this property combines historic charm with conveniences that are often difficult to find in this location. The home is ready for its next owner to update and personalize while preserving its unique character and historic appeal.

87 Shipwright St, Annapolis

Listing courtesy of RE/MAX Executive. Contact:

$6,500,000

7 Beds ⋅ 9 Baths

A truly iconic Annapolis offering, this extraordinarily rare waterfront estate is gracefully set on 7.5 remarkably private acres, showcasing what may be the most breathtaking panoramic views in all of Annapolis. With endless, horizon-stretching vistas that evoke the feel of an oceanfront retreat, the Chesapeake Bay unfolds before you with the Bay Bridge creating a dramatic backdrop in the distance, while Annapolis’ beloved summer sailboat races become part of your everyday scenery. A setting of this magnitude—offering serenity, privacy, and commanding water views—is simply irreplaceable. Encompassing more than 9,000 square feet, this grand residence was thoughtfully designed to maximize its extraordinary setting, with jaw-dropping water views greeting you the moment you step through the front door and drawing your eye through the soaring two-story family room straight to the Chesapeake beyond. The architectural footprint and flow are exceptional, creating the perfect canvas for a visionary buyer to elevate this estate into a world-class showpiece. The main level is anchored by an expansive waterfront primary retreat, a sanctuary unto itself featuring dual walk-in closets, a spa-inspired bath with a jetted soaking tub, oversized skylit shower, separate vanities, a bidet, and a private spiral staircase leading directly to the lower-level fitness and hot tub retreat. Two additional generously sized en suite bedrooms with walk-in closets are also conveniently located on the main level, along with a richly appointed study/library, elegant formal dining room, spacious kitchen with island and breakfast area, plus an additional family gathering space designed for effortless everyday living and entertaining. Upstairs, two exceptional en suite bedrooms each offer walk-in closets, fireplaces, private waterfront balconies, and spectacular elevated views that feel suspended above the Bay. The walkout lower level is equally impressive, designed for entertaining and multigenerational flexibility, featuring expansive recreation spaces opening directly to the waterfront patio, plus a fully self-contained in-law or au pair apartment complete with its own kitchen, family room, full bath, separate entrance, and—of course—those same extraordinary views. What sets this offering even further apart is the remarkable future potential already in motion. With public sewer and an extraordinary 7.5-acre footprint, the possibilities are nearly limitless. Seller-approved county plans—transferable to the next owner—dramatically accelerate the vision, including plans for shoreline improvements, tree clearing to further expand views, bank reshaping, revetment enhancements, a new tram and stair access to the pier, a widened driveway with a new entrance feature, a detached guest house with its own private entrance from Lyons Dr, a pickleball court, a gazebo, and additional grounds enhancements. This is more than a home—it is one of Annapolis’ most extraordinary legacy properties, offering a once-in-a-generation opportunity to create an unparalleled waterfront masterpiece.

2562 Carrollton Rd, Annapolis

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$3,849,000

6 Beds ⋅ 5 Baths

A truly exceptional historic residence is now available in the heart of downtown Annapolis. Welcome to 16 Maryland Avenue, a distinguished circa-1830 Greek Revival home masterfully restored in collaboration with the renowned Hammond-Wilson Architects. Perfectly positioned just steps from State Circle and the United States Naval Academy, this iconic three-story brick property seamlessly blends timeless architectural beauty with sophisticated modern livability. The main property features 4,474 square feet of refined above-grade living space, complemented by a fully legal, licensed lower-level apartment that offers immense versatility for multi-generational living or premium rental income. In total, the property features six bedrooms, 4.5 bathrooms, and beautifully curated living spaces defined by rich period details, soaring ceilings, and remarkable craftsmanship. Six fully rebuilt, functional wood-burning fireplaces (three equipped with gas starters) serve as stunning architectural focal points throughout the home. Equally captivating are the enchanting outdoor spaces. Here, manicured grounds, lush landscaping, vibrant flower beds, and a serene koi pond create a private garden retreat rarely found downtown. Set on a prime 7,324-square-foot lot along one of the city’s most coveted historic streets, the property offers tranquility just moments from the waterfront and bustling downtown scene. Zoned as a two-family residence, this remarkable property represents a rare, premium investment or a luxurious private estate. Residents will enjoy an unmatched lifestyle, surrounded by boutique shopping, acclaimed waterfront dining, art galleries, historic landmarks, and the unmistakable charm of Annapolis Harbor. Elegant, iconic, and rich with history, 16 Maryland Avenue represents downtown Annapolis living at its absolute finest.

16 Maryland Ave, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686

$950,000

6 Beds ⋅ 6 Baths

Two houses for the price of one! 704 Caleb Lane includes an amazing garden apartment, perfect for an in-law or au pair! It is beautifully maintained and loaded with recent updates in the highly sought-after, amenity-rich Kingsport community of Annapolis. The spacious, open floor plan is enhanced by the many value-added updates in the home, including the renovated kitchen, roof (2022), HVAC systems (2025 and 2022), and water heater (2022). The light-filled walk-out lower level is a complete in-law/au pair suite that includes a kitchen, both a full AND a half bath, a 2nd laundry, and not one but two bedrooms! A huge bonus and sheer perfection for guests, multigenerational living, a theater room, or an extended entertaining space. The stunning main-level kitchen is designed to impress, featuring sparkling granite countertops, a massive center island, custom cabinetry, and convenient access via a fun and functional secondary staircase. The kitchen opens seamlessly to the dramatic two-story Great Room, highlighted by a cozy gas fireplace, soaring windows, and elegant custom wood blinds that run throughout the main level. Beautifully maintained hardwood floors run throughout the home, adding warmth and timeless appeal. Outside, the pristine driveway with ample parking and an oversized two-car garage with built-in cabinets and fantastic storage space for gardening, landscaping, and recreational needs. Situated on nearly a quarter-acre lot, the property is the best location in the neighborhood, just two short blocks from the community pool, clubhouse, playgrounds, water access for kayaking and fishing, and scenic walking and biking trails. This exceptional property offers the perfect blend of comfort, elegance, and convenience. Located only 10 minutes from Downtown Annapolis, this home provides the tranquility of private community living without sacrificing easy access to shopping, dining, and waterfront attractions. This elegant home truly checks every box — offering exceptional space, thoughtful upgrades, outstanding community amenities, and an unbeatable Annapolis location.

704 Caleb Ln, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600

$2,950,000

6 Beds ⋅ 5 Baths

PRICE REDUCTION 245K! Welcome to 1588 Eaton Way, an extraordinary, waterfront Chesapeake Bay retreat offering the very best of Annapolis living. Located in the highly coveted Downs on the Severn neighborhood, this custom California Deck‑style home spans 7,000+ square feet on 2 private acres with deep‑water access (6+ ft MLW) and stunning views of Clements Creek. Designed as a true waterfront estate, this home blends architectural character, thoughtful modernization, and resort‑style amenities—perfect for boating enthusiasts and those seeking a refined Bay lifestyle. Waterfront features a private dock with 50‑amp power boat lift configured for a 21’ vessel (parts available for jet skis or other boat sizes). Deep‑water slips at dock that are over 8 feet+ mean low. The Polaris utility vehicle conveys for easy waterfront access (and snow plow attachments included). Host all your gatherings at the park like waterfront dock. This home is truly special & unique compared to most other waterfront homes! There have been major improvements in this 6-bedroom waterfront home. There are water views from nearly every room! This home features Hardie Plank siding with vinyl‑wrapped trim in 2024, new roof system in 2021— not just shingles, and four new garage doors & openers. There is a Sub‑Zero refrigerator/freezer installed in 2021, updated dock electrical & lift adjustments, new wood‑burning stove at lower‑level club/bar. The primary suite bath was a complete down‑to‑the‑studs renovation featuring steam shower, deep soaking tub, towel warmer, and Onii toilet/bidet. The Jack‑and‑Jill bath renovated with Jacuzzi tub, rain shower, hand shower, and towel warmer. This home has a beautiful, private layout that combines style & comfort for everyone. The interior highlights are custom architectural design with knotty pine ceilings throughout, two‑sided stacked‑stone wood‑burning fireplace. There is a fully updated kitchen, central vacuum system with outlets throughout home and garages, central audio system with controls indoors and out, and RV‑sized garage with power! The upper garage equipped with hot & cold water plus floor drains—perfect for year‑round vehicle care! Where else can you find that? There have been several updates on the home at 1588 Eaton Way. The kitchen has instant hot water dispenser. The updated outdoor lighting is new. There is restored hardwood flooring throughout home, and new carpeting. The systems in the home have all been meticulously maintained. There are all new skylights and most all of the windows & some doors throughout the home! There is professionally maintained 12‑zone irrigation system for upper and lower lawns and is seasonally serviced. This tranquil Severn River location offers breathtaking water views, abundant wildlife, and easy access to downtown Annapolis, the Chesapeake Bay, and major commuter routes—without sacrificing privacy or serenity. 1588 Eaton Way is a rare opportunity to own a meticulously maintained, deep‑water estate in one of Annapolis’ most prestigious waterfront communities. The Downs on the Severn features two community marinas, an outdoor community swimming pool with swim team, tennis courts, pickle ball, and a clubhouse for year-round socials. There are also tot lots for the little ones, and a little library. The Downs is an easy commute to Baltimore, DC and the beaches. The airport is less than 30-minute drive. This is truly a resort vacation at home in the Downs on the Severn! HOME IS BEING SOLD AS IS. Contact listing agent for details!

1588 Eaton Way, Annapolis

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

$850,000

6 Beds ⋅ 3 Baths

Some addresses just make life better. This one is tucked back in Beechwood on the Burley — a sought-after water-privileged community in St. Margarets, with private access to Burley Creek for kayaking, canoeing, and boating, plus a community pier, dock slips, and picnic area steps from your door. Downtown Annapolis is less than 2 miles away, yet the setting feels genuinely private, sheltered under a canopy of mature trees on a generous 0.7-acre lot. The house itself offers a rare combination: five bedrooms a, an open kitchen-to-family-room layout, a potential main-level bedroom and full bath ideal for guests or multigenerational living, a kitchen island, and built-in Bose surround sound with TV that conveys. A dedicated main-floor den gives you the flexibility to work from home without sacrificing living space. The two-car attached garage with four additional driveway spaces means there is always room for boats, bikes, kayaks, and company. Launch your boat from the private community ramp with quick access to Burley Creek and the Severn River, enjoy the community pier and waterfront playground, and experience the Annapolis lifestyle at its finest with easy access to restaurants, shopping, and marinas by both boat and car. Whether you are upsizing into a home that finally fits the whole family, seeking a place to launch a kayak on a Tuesday morning before work, or looking for a Chesapeake Bay-area property that gives you space without sacrificing proximity to Annapolis, this home delivers on all counts. Come see it before summer is in full swing!

1848 Cherry Rd, Annapolis

Listing courtesy of Engel & Volkers Annapolis. Contact: (443) 292-6767

$1,950,000

6 Beds ⋅ 4 Baths

Welcome to the Thomas Hyde House – a rare opportunity to own a piece of Annapolis history in the heart of downtown. Built in 1769, this impeccably restored Federal- style property blends 18th-century charm with modern luxury. Perfectly situated on sought- after Duke of Gloucester Street, this vibrant and colorful home offers stunning views of the Maryland State House and extremely rare off-street parking for 6+ vehicles. Originally configured as office space, the residence has been reimagined into six spacious bedrooms and four full baths across two beautifully fully remodeled levels, with the potential for third floor updating plus a large basement with ample storage and updating space. The first floor offers true single level living with a primary suite and second bedroom, while the second level features four additional bedrooms and a convenient laundry area. No detail has been overlooked – from new appliances, countertops, and cabinetry to frameless glass showers, ceramics, extensive trim and molding, recessed lighting, fresh interior and exterior paint, new plumbing/electric and sprinkler system, updated flooring, freshly painted standing seam roof/front dormers and more. The result is a turnkey home where historic character meets modern sophistication & luxury. The property is offered with negotiable furnishings, electronics and art, The Thomas Hyde House is as versatile as it is fun and captivating. Just steps from downtown Annapolis shopping, dining, yacht clubs, local marinas & major commuter routes. Whether as a primary residence, investment property, or distinctive downtown retreat. schedule your showing today.

192 Duke Of Gloucester, Annapolis

Listing courtesy of Samson Properties. Contact: 3017555613

$2,500,000

6 Beds ⋅ 7 Baths

READY TO BUILD NOW!! Introducing an exceptional opportunity to build your dream home with a local custom home builder on a rare 2.19-acre homesite in the highly sought-after water-privileged community of Winchester on the Severn—a neighborhood where everyday living feels like a vacation. This thoughtfully designed custom home will offer over 6,700 square feet of finished living space, featuring 6 bedrooms, 6 full baths, and 1 half bath, along with a 3-car garage, blending timeless craftsmanship with modern luxury and functionality. The main level is designed with both comfort and entertainment in mind, showcasing an open-concept floor plan anchored by a gourmet kitchen featuring high-end appliances, an expansive workspace, and seamless flow into gathering spaces. A beautifully appointed butler’s pantry includes a built-in ice maker and is complemented by a walk-in pantry, demonstrating the careful attention to detail found throughout the home. A rare main-level bedroom with en suite bath, along with a dedicated private office, provides exceptional flexibility for guests, multi-generational living, or work-from-home convenience. Upstairs, you’ll find four generously sized bedrooms, each offering its own walk-in closet and own en suite bathroom —a rare and highly desirable feature. The primary suite serves as a luxurious retreat, complete with separate his-and-hers walk-in closets and a spa-inspired bathroom featuring a soaking tub and oversized walk-in shower. The finished lower level is designed for entertainment and relaxation, featuring a spacious recreation room, a dedicated theater room, and an optional bar area with its own pantry and possible wine storage room. An additional en suite bedroom on this level makes the space ideal for extended guests, in-laws, or a live-in nanny. Set on an exceptionally rare 2.19-acre homesite, the property offers endless possibilities for outdoor living, including space approved for a future pool, pickleball court, or custom outdoor entertainment retreat of your choice —creating the ultimate private backyard oasis. Life in Winchester on the Severn offers an unmatched lifestyle. Simply hop on your golf cart and head to one of the finest community beaches on the Severn River, where residents enjoy a playground, pavilion, sandy beach, swimming pier, kayak and paddleboard storage and launch, boat ramp, and breathtaking sunsets over the water. This is an extremely rare opportunity to create a custom residence in one of the area’s most desirable water-privileged communities—where luxury, space, and lifestyle come together seamlessly.

1603 Winchester Rd, Annapolis

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$1,198,000

9 Beds ⋅ 5 Baths

NEW PRICE! Welcome to 805 Spa rd., an amazing investment opportunity in the desirable Murray Hill community in Annapolis! Murray Hill is probably the best residential neighborhood in the city with single-family homes, and walkable to downtown. This 9-bedroom, 4.5 bath, triplex home has been completely renovated! There is ample parking for up to 8 cars. This home offers rental potential with 3 separate units under 1 roof. This property could be short or long-term rental investment, a multi-generational home, or owner-occupied housing hack, which enables the owner to live in one side and rent out the other sides to pay and qualify for the mortgage. There are 3 units, Unit 1 has 4 beds, 2.5 baths, unit 2(in the back) has 3 beds, 1bath, and the basement has 2 bed, 1 ba. All have separate entrances. The entire house has been completely renovated with all new wiring, plumbing, 3 new kitchens and 4.5 new baths, new HVAC,2nd unit new hot water heater, sprinkler system all units, granite counter tops, stainless steel appliances, all new flooring throughout and enclosed porch with all new windows.

805 Spa Rd, Annapolis

Listing courtesy of Bennett Realty Solutions. Contact: 3016464047

$1,199,000

6 Beds ⋅ 5 Baths

Tranquility and nature awaits you in this timeless all-brick estate, thoughtfully designed for both everyday living and MULTI-GENERATIONAL l flexibility — offering the rare feeling of living in your own private retreat while still being just minutes from the heart of Annapolis. With over 5,500 square feet, multiple private living areas, and the potential for dual primary-style suites, this home is perfectly suited for extended family living, an au pair setup, long-term guests, or evolving household needs. A long private drive opens to a circular driveway welcoming you home to a picturesque landscape filled with mature trees and open space. Complete with a three-car garage and separate shed, there’s plenty of room for vehicles, hobbies, storage, and weekend projects. Your home unfolds with beautifully designed living space, where hardwood floors, freshly painted interiors, abundant natural light, and generous room sizes create a warm and inviting atmosphere. The main level offers two spacious living areas, both with cozy fireplaces, a formal dining room, and a private office that could easily function as a main-level bedroom — creating additional flexibility for guests or multi-generational living needs. The second level features four spacious bedrooms and three full baths, along with a large bonus room over the garage offering endless possibilities for a playroom, studio, secondary living area, or potential second primary suite. The expansive primary retreat is complete with its own fireplace and large private bath featuring a soaking tub, separate shower, and dual vanity. The third upper level provides two additional bedrooms and a full bath, creating a private retreat ideal for guests, an au pair suite, or extended family. The finished lower level adds even more versatility with a large recreation room, exercise space, abundant storage, and walkout access to a second patio leading to the generous backyard. The lower backyard offers a secluded setting perfect for bonfires, s’mores, and evenings gathered with friends and family under the trees. Your outdoor experience continues with an expansive deck overlooking 2.25 private acres of surrounding woodland — an ideal setting for summer dinners, quiet mornings with coffee, or simply decompressing while listening to nature. Fresh eggs await from your very own chicken coop — and the chickens can convey if buyers wish. Perfectly positioned for your private oasis, yet just minutes from Annapolis, the Naval Academy, commuter routes, and local shopping. WATER ACCESS AND MARINAS JUST MINUTES AWAY- 3 MILES! A rare opportunity to enjoy space, privacy, flexibility, and nature while staying connected to everything the Annapolis area has to offer.

962 Coachway, Annapolis

Listing courtesy of Compass. Contact: (410) 429-7425

$1,328,491

6 Beds ⋅ 4 Baths

Waterfront Views - Annapolis Roads Community! AMAZING BRAND NEW WATER VIEW HOME in a desirable Annapolis, MD location! This stunning 6 bedroom, 3 full bathroom residence offers multigenerational living plus all the amenities of Annapolis Roads . Ask about the lock and leave lifestyle. Situated in the sought-after Annapolis Roads community, the home occupies a premium 20,125 sq ft corner lot and features a 2-car side load garage. Special features include Special financing 2/1/buydown at 4.5 % Included two year lawn maintenance 9-foot ceilings and LVP hardwood floors throughout Gourmet kitchen with stainless steel appliances, 42-inch white maple cabinets, large island and quartz countertops A spacious great room centers around an inviting fireplace Formal dining room, living room Main level 6th bedroom/den/office option, full bathroom Conveniently located laundry room near the garage entrance 6 bedrooms and 3 full bathrooms Expansive primary suite with a bonus room perfect for an office, gym, or reading room Luxurious primary bathroom showcasing a quartz double bowl vanity, ceramic tile throughout, soaking tub and a large glass shower A secondary suite bedroom and bath are located down the hall Three additional bedrooms and a full bathroom complete this level For future expansion, the home includes a 1,717 sq ft unfinished basement ready for customization. Act now to own this home.

2644 Claibourne Rd, Annapolis

Listing courtesy of Keller Williams Flagship. Contact:

$4,950,000

7 Beds ⋅ 7 Baths

Ideally situated on the banks of Luce Creek with sweeping views down the Severn River, 1715-1717 Porters Hill Road is a unique heritage property with over a century of history. Set on a 2.96 acre lot with 429 ft of waterfrontage, the property is comprised of two separate parcels and includes a large, hard-to-find boathouse that provides both charm and utility for all your waterfront adventures. The private pier has 8+ ft water depth and can accommodate a large vessel as well as an assortment of smaller boats. The tram makes access to the water effortless, and the entire property enjoys exceptional privacy. Steeped in its storied past yet thoughtfully updated for modern living, this retreat captures the perfect balance of historic charm and casual elegance. The heart of the main home is a sunlit great room with original log walls and quarried stone fireplace, a vaulted ceiling, and expansive windows which frame water views at every turn. An adjoining den, with separate entrance option, is a perfect place to relax. This could easily become another main level bedroom with ensuite bathroom. The kitchen is striking under its vaulted ceiling accented by exposed beams. The custom cabinetry and generous island give the space so much functionality while maintaining the artisanal character. The kitchen opens to the dining area overlooking the water. Step outside and you’re embraced by nature: multiple porches and decks overlook lush, manicured grounds that lead down to the water’s edge. The main-level primary suite is a true sanctuary, designed for privacy and tranquility. The bedroom, with a vaulted ceiling, has a screened porch overlooking the water. Two expansive walk-in closets offer custom organization systems that would make a clothing connoisseur smile. The spa-like bathroom gets lots of natural light from the windows that frame the water, and the freestanding soaking tub is situated to enjoy this view. A dual-sink vanity, heated floors, and generous walk-in shower with a built-in bench make getting ready feel effortless and luxurious. A dedicated laundry area just off the hallway makes day-to-day living very easy. Part of the primary suite is a gracious office with gas fireplace and outdoor access. This is a totally flexible space: install a wall of bookshelves and you’d have a lovely library. Upstairs, there are two generously sized bedrooms. One has water views and a waterside balcony; the other overlooks the lush landscaping out front. There is a hall bathroom. A separate guest bedroom suite above the garage, complete with its own living area and luxe bathroom, is ideal for visiting friends and family who desire more privacy. The second home, on the 1717 lot, offers a contemporary setting with clean lines and spacious deck. The dramatic two-story family room facing the kitchen means tons of natural light for the entire house. The main level has a bedroom and full bathroom, and there are two more bedrooms upstairs that share a hall bath. The walk-out lower level features a rec room and a large utility/storage area. The Historical Context: Originally built in the 1880s, the log house on 1715 was one of three identical structures used as hunting lodges. The logs from this original lodge were re-sized to create the current great room. The construction of the log house is one of great craftmanship, including sizing each log to be approximately the same diameter as others. It's amazing that 1715-1717 has such easy access to downtown Annapolis by car or boat, and for those who commute to DC or Baltimore, Route 50 is less than 10 minutes. This incredible heritage property, encompassing almost three acres, two dwellings and a deep-water pier with boathouse, is the ultimate Annapolis retreat.

17151717 Porters Hill Rd, Annapolis

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

$6,995,000

7 Beds ⋅ 6 Baths

Escape to another world with this striking French modern waterfront estate. Exquisitely sited on a premium and private 4.15 acre lot with 600 feet of impressively rip-rapped water frontage, coveted waterfront pool, tennis court and picturesque views of the serene waters of Whitehall Creek. This ultra-luxe 9,000+ square-foot, 7 bedroom, 5.5 bathroom custom built home has been completely renovated. It is evident from the moment you walk in the front door that no expense was spared with this stunning home. Curated with premium quality, top of the line materials, combined with the tranquil views, exquisite design, and top-tier finishes, 1524 Cedar Lane Farm Road is truly one-of-a-kind and showcases unparalleled craftsmanship. The property both inside and out is an absolute entertainer's dream. The lush lawn and landscaping gracefully extends to the water's edge and leads to the well-appointed multi-slip IPE pier with boat lifts, 2 jet ski lifts, upgraded power, water and great lighting including underwater LED fishing lights. Inside, this stunning home boasts an awe-inspiring Great Room with soaring ceilings, architectural beams, and panoramic water views and features brushed Teak hardwood flooring, renovated high-end gourmet Kitchen with marble counters, 10 burner Wolf range, 5 fireplaces, Restoration Hardware lighting, renovated bathrooms throughout and much more! Fall asleep to captivating, sweeping views from the Primary's suite, enjoy watching the early morning wildlife activity on the water. Located on Whitehall Creek which flows out to Whitehall Bay and beyond to the Chesapeake Bay, you are perfectly located to take advantage of the Bay's best cruising and fishing areas. Attractive destinations such as the Annapolis Harbor, Baltimore's Inner Harbor, St. Michaels, Oxford, and Solomon's Island are only a short cruise away and just minutes from accessing Rt. 50 and 97 which provides direct access to Baltimore, BWI, Ft. Meade/NSA and Washington, DC., or head over the Bay Bridge to the Eastern Shore for a quick beach vacation. Welcome Home!

1524 Cedar Lane Farm Rd, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600

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