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5-Bedroom Homes for Sale in Annapolis, MD

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  • 15 E Nap Ln, Annapolis, MD 21409
    15 E Nap Ln, Annapolis, MD 21409
    /2

    $1,300,500 Coming Soon

    • 5 Beds
    • 3 Baths
    • 5,465 Sq Ft

    15 E Nap Ln, Annapolis, MD 21409

    Coming Soon! Get ready to fall in love with this Annapolis gem Nestled in the sought-after Captain Cove neighborhood on a 1.21-acre wooded lot, this beautifully maintained home is minutes from downtown Annapolis.Unique features include a rooftop deck, expansive back decking, and a bonus treehouse that doubles as a fun space for children or a peaceful retreat for adults—perfect as a she shed or

    Agent Photo

    Litra Simms

    Simms and Associates

    (443) 339-8629

    15 E Nap Ln, Annapolis, MD 21409
  • 187 Browns Woods Rd, Annapolis, MD 21409
    187 Browns Woods Rd, Annapolis, MD 21409
    187 Browns Woods Rd, Annapolis, MD 21409
    /25

    $545,000 Open Sun 11AM - 1PM

    • 5 Beds
    • 2 Baths
    • 1,064 Sq Ft

    187 Browns Woods Rd, Annapolis, MD 21409

    Welcome to 187 Browns Woods Road – The Perfect Blend of Style, Space, and Versatility!Nestled in a peaceful Annapolis neighborhood, this beautifully updated rancher is the definition of move-in ready and packed with features that make it ideal for multi-generational living or anyone seeking flexible space. With 5 bedrooms, 2 full bathrooms, and two fully equipped kitchens, this home

    Agent Photo

    Dee Akindoyo

    Coldwell Banker Realty

    (410) 618-4239

    187 Browns Woods Rd, Annapolis, MD 21409
  • 120 Stilly Way, Annapolis, MD 21403
    120 Stilly Way, Annapolis, MD 21403
    120 Stilly Way, Annapolis, MD 21403
    /21

    $1,097,990 New Construction

    • 6 Beds
    • 5.5 Baths
    • 4,934 Sq Ft

    120 Stilly Way, Annapolis, MD 21403

    This expansive two-story home showcases a gracious design with abundant room to grow and entertain. Off the foyer is a formal dining room that complements the casual nook and breakfast room, plus a gourmet kitchen and a Great Room with a charming fireplace. On the second floor is a loft surrounded by three secondary bedrooms and a luxurious owner’s suite with a spa-style bathroom. A lower-level

    Agent Photo

    Terri Hill

    Builder Solutions Realty

    (410) 881-8195

    120 Stilly Way, Annapolis, MD 21403
  • 118 Stilly Way, Annapolis, MD 21403
    118 Stilly Way, Annapolis, MD 21403
    118 Stilly Way, Annapolis, MD 21403
    /21

    $1,065,990 New Construction

    • 5 Beds
    • 5.5 Baths
    • 4,934 Sq Ft

    118 Stilly Way, Annapolis, MD 21403

    Exuding grace at the moment of entry, this expansive two-story home features an open-plan layout ideal for modern living. A fireplace anchors the Great Room, which flows into the dining area and gourmet kitchen with a versatile island. Upstairs are three bedrooms, a loft suite sitting room, and a luxurious owner’s suite with spa-style bath. Extra space abounds with a main-level study, upstairs

    Agent Photo

    Terri Hill

    Builder Solutions Realty

    (410) 632-6668

    118 Stilly Way, Annapolis, MD 21403
  • 1486 Downham Market, Annapolis, MD 21401
    1486 Downham Market, Annapolis, MD 21401
    1486 Downham Market, Annapolis, MD 21401
    /106

    $3,250,000

    • 5 Beds
    • 4.5 Baths
    • 5,260 Sq Ft

    1486 Downham Market, Annapolis, MD 21401

    Introducing 1486 Downham Market—an architectural gem perched on a premier waterfront lot in the prestigious Downs on the Severn. This transitional-style contemporary offers sophisticated elegance with clean lines, refined finishes, and walls of glass that bring the outside in. With 5 bedrooms and 4.5 baths across three thoughtfully finished levels, every inch of this home was designed to impress.

    Wendy Oliver Coldwell Banker Realty

    1486 Downham Market, Annapolis, MD 21401
  • 917 Childs Point Rd, Annapolis, MD 21401
    917 Childs Point Rd, Annapolis, MD 21401
    917 Childs Point Rd, Annapolis, MD 21401
    /40

    $3,700,000

    • 5 Beds
    • 6 Baths
    • 6,094 Sq Ft

    917 Childs Point Rd, Annapolis, MD 21401

    This stunning waterfront retreat offers privacy, breathtaking views of Crab Creek and the South River, and a waterside pool. The newly extended pier can accommodate a 50' sailboat. South-facing exposure and walls of windows let in tons of natural light and the sunlight sparkles off the serene waters at the shoreline. The beautiful renovation by Gate One Builders and new hardwood flooring created

    Brad Kappel TTR Sotheby's International Realty

    917 Childs Point Rd, Annapolis, MD 21401
  • 3259 Chrisland Dr, Annapolis, MD 21403
    3259 Chrisland Dr, Annapolis, MD 21403
    3259 Chrisland Dr, Annapolis, MD 21403
    /46

    $1,550,000

    • 5 Beds
    • 3.5 Baths
    • 4,583 Sq Ft

    3259 Chrisland Dr, Annapolis, MD 21403

    Welcome Home to 3529 Chrisland Drive! This beautifully upgraded 5-bedroom, 4-bathroom is located in the highly desired neighborhood of Annapolis Cove, only minutes from downtown Annapolis. Enjoy stunning views of the water from all aspects of your new home. A gourmet open kitchen, family room, formal dining room, formal living room, sunroom, private office and half bath offer amazing living

    Michelle Kirby Coldwell Banker Realty

    3259 Chrisland Dr, Annapolis, MD 21403
  • 3209 Henson Ave, Annapolis, MD 21403
    3209 Henson Ave, Annapolis, MD 21403
    3209 Henson Ave, Annapolis, MD 21403
    /81

    $1,950,000

    • 5 Beds
    • 5.5 Baths
    • 4,348 Sq Ft

    3209 Henson Ave, Annapolis, MD 21403

    Perched above a quiet cove just minutes from downtown Annapolis, this refined Southern Colonial offers a rare combination of privacy, flexibility, and water views that will never be obstructed. With the Chesapeake Bay Foundation Nature Sanctuary directly across the creek, the setting is defined by light, sky, and uninterrupted natural beauty.\n\nGraciously scaled living and entertaining

    Brian Mayer Real Broker, LLC

    3209 Henson Ave, Annapolis, MD 21403
  • 3412 Hidden River View Rd, Annapolis, MD 21403
    3412 Hidden River View Rd, Annapolis, MD 21403
    3412 Hidden River View Rd, Annapolis, MD 21403
    /73

    $2,650,000

    • 5 Beds
    • 5.5 Baths
    • 5,671 Sq Ft

    3412 Hidden River View Rd, Annapolis, MD 21403

    CASUAL ELEGANCE BEST DESCRIBES THIS COASTAL STYLE HOME IN THE SOUGHT AFTER COMMUNITY OF FISHING CREEK FARM. THIS HOME IS AN ENTERTAINERS DREAM! THIS 5 BEDROOM, 5 BATH HOME HAS IT ALL! EXQUISITE DETAILS THROUGHOUT, RESORT STYLE HEATED POOL WITH WATERFALLS, OUTDOOR SHOWER, OUTDOOR FIREPLACE THAT LEADS TO A GREAT ENTERTAINING AREA UNDER THE DECK OFF THE POOL WITH WET BARS, HIGH TOPS, OUT DOOR TV'S,

    Pamela Tierney Coldwell Banker Realty

    3412 Hidden River View Rd, Annapolis, MD 21403
  • 2514 Lyon Dr, Annapolis, MD 21403
    2514 Lyon Dr, Annapolis, MD 21403
    2514 Lyon Dr, Annapolis, MD 21403
    /65

    $3,850,000

    • 6 Beds
    • 6.5 Baths
    • 5,678 Sq Ft

    2514 Lyon Dr, Annapolis, MD 21403

    Life will never be the same. This slick and sleek coastal contemporary is beautifully designed for optimal waterfront living. With six bedrooms (FIVE ensuites), six full baths and one half bath, waterviews are visible from nearly all living spaces and bedrooms (and three bathrooms, to be fair). Witness the walls of windows on the first level, facing the Chesapeake Bay to the East and Severn

    Marcia Zercoe TTR Sotheby's International Realty

    2514 Lyon Dr, Annapolis, MD 21403
  • 201 Nottingham Hill, Annapolis, MD 21405
    201 Nottingham Hill, Annapolis, MD 21405
    201 Nottingham Hill, Annapolis, MD 21405
    /90

    $1,980,000

    • 5 Beds
    • 3 Baths
    • 2,353 Sq Ft

    201 Nottingham Hill, Annapolis, MD 21405

    PRICE REDUCTION - Exciting Opportunity in Sherwood Forest – Enjoy breathtaking panoramic water vistas of Brewers Pond and Round Bay on the Severn River. Observe Bald Eagles, Herons, and Osprey soaring amidst the stunning backdrop from your water view deck or spacious living room adorned with floor-to-ceiling windows. This elegantly designed home, nestled in the hillside, seamlessly blends modern

    Brian Wood Long & Foster Real Estate, Inc.

    201 Nottingham Hill, Annapolis, MD 21405
  • 1241 Cherry Tree Ln, Annapolis, MD 21403
    1241 Cherry Tree Ln, Annapolis, MD 21403
    1241 Cherry Tree Ln, Annapolis, MD 21403
    /47

    $2,675,000

    • 5 Beds
    • 5.5 Baths
    • 6,428 Sq Ft

    1241 Cherry Tree Ln, Annapolis, MD 21403

    Exquisite Savannah Style custom-built home in sought after, amenities-rich, Fishing Creek Farm community in Annapolis. This non-riparian waterfront home is nestled between 2 bodies of water providing endless water views from almost every room of the house. Wake up early to watch the wildlife and the sunrise over Cherry Tree Cove from the rear screened porch or enjoy peaceful water views and

    Brad Kappel TTR Sotheby's International Realty

    1241 Cherry Tree Ln, Annapolis, MD 21403
  • 934 Chesterfield Rd, Annapolis, MD 21401
    934 Chesterfield Rd, Annapolis, MD 21401
    934 Chesterfield Rd, Annapolis, MD 21401
    /73

    $1,950,000 New Construction

    • 6 Beds
    • 5.5 Baths
    • 5,636 Sq Ft

    934 Chesterfield Rd, Annapolis, MD 21401

    The One That Outshines Them All—Near Downtown AnnapolisThis stunning newly built colonial home is a true showcase of thoughtful design and refined craftsmanship, beautifully situated on 1.34 acres with no association fees to limit your lifestyle. From the rich French white oak flooring and custom stair railings to the intricate glass doorknobs and solid wood doors, every detail has been

    Bryan D. Gamble Gamble Realty, Inc

    934 Chesterfield Rd, Annapolis, MD 21401
  • Lynnfield, Annapolis, MD 21403
    Lynnfield, Annapolis, MD 21403
    Lynnfield, Annapolis, MD 21403
    /3

    $1,039,990 New Construction

    • 5 Beds
    • 5.5 Baths
    • 4,954 Sq Ft

    110 Stilly Way, Annapolis, MD 21403

    This exquisite three-story, 5-bedroom, 5.5-bathroom home offers 4,954 sq. ft. of sophisticated living space. Designed for modern living, the open-concept first floor features a Great Room with a central fireplace, seamlessly connecting to the dining areas and a chef-inspired kitchen with a versatile island. The upper level is home to three spacious bedrooms and a luxurious owner’s suite with a

    Lennar

    Lynnfield, Annapolis, MD 21403
  • 2644 Claibourne Rd, Annapolis, MD 21403
    2644 Claibourne Rd, Annapolis, MD 21403
    2644 Claibourne Rd, Annapolis, MD 21403
    /62

    $1,484,000 New Construction

    • 6 Beds
    • 4 Baths
    • 3,702 Sq Ft

    2644 Claibourne Rd, Annapolis, MD 21403

    AMAZING BRAND NEW WATER VIEW HOME - This stunning 6 bedroom, 4 full bathroom residence offers 3,702 sq ft of finished space with breathtaking views of Lake Heron and the Chesapeake Bay. 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. The main level showcases 9-foot ceilings and LVP hardwood floors

    Brian Wood Long & Foster Real Estate, Inc.

    2644 Claibourne Rd, Annapolis, MD 21403
  • 1165 Neptune Place, Annapolis, MD 21409
    1165 Neptune Place, Annapolis, MD 21409
    1165 Neptune Place, Annapolis, MD 21409
    /78

    $785,000

    • 5 Beds
    • 3.5 Baths
    • 3,424 Sq Ft

    1165 Neptune Place, Annapolis, MD 21409

    Welcome to this stunning and spacious colonial nestled in one of the area's most sought-after water-privileged neighborhoods! This gorgeous home offers the perfect blend of timeless elegance and modern comfort, with generous living spaces and upscale finishes throughout.Step inside to find a grand foyer, formal living and dining rooms, and a large, sun-filled family room with a cozy

    Amy Juras Long & Foster Real Estate, Inc.

    1165 Neptune Place, Annapolis, MD 21409
  • 917 Arbutus Rd, Annapolis, MD 21403
    917 Arbutus Rd, Annapolis, MD 21403
    917 Arbutus Rd, Annapolis, MD 21403
    /121

    $5,250,000

    • 5 Beds
    • 3.5 Baths
    • 3,945 Sq Ft

    917 Arbutus Rd, Annapolis, MD 21403

    Welcome to 917 Arbutus Road—an extraordinary waterfront property nestled on 5 private acres with deep water on Crab Creek minutes from downtown Annapolis. This mid-century modern home offers over 3656 SF of light-filled living space, with soaring ceilings, expansive glass walls, and panoramic views of water and nature. The main level boasts four bedrooms and open-concept living areas designed

    Georgie Berkinshaw Coldwell Banker Realty

    917 Arbutus Rd, Annapolis, MD 21403
  • 1014 St Charles Dr, Annapolis, MD 21409
    1014 St Charles Dr, Annapolis, MD 21409
    1014 St Charles Dr, Annapolis, MD 21409
    /28

    $739,900

    • 5 Beds
    • 3 Baths
    • 3,312 Sq Ft

    1014 St Charles Dr, Annapolis, MD 21409

    This beautifully updated 5-bedroom, 3-full bath home offers the perfect combination of charm, space, and modern updates. Freshly painted throughout with gleaming hardwood floors and brand-new carpet, this home is truly move-in ready.The bright, updated kitchen is ideal for cooking and entertaining, while the family room with sunroom area provides a versatile space for relaxing or

    John Burgess Samson Properties

    1014 St Charles Dr, Annapolis, MD 21409
  • 46 Boxwood Rd, Annapolis, MD 21403
    46 Boxwood Rd, Annapolis, MD 21403
    46 Boxwood Rd, Annapolis, MD 21403
    /47

    $599,900

    • 5 Beds
    • 3 Baths
    • 2,928 Sq Ft

    46 Boxwood Rd, Annapolis, MD 21403

    ***MULTIPLE OFFERS RECEIVED. HIGHEST AND BEST OFFER AND TERMS DUE TUESDAY 7/22/2025 AT 5PM***Welcome to your dream home in the heart of Annapolis, where spacious living meets modern style and convenience. This stunning 5-bedroom, 3-bathroom split foyer has been thoughtfully reimagined with high-end finishes, offering the perfect blend of elegance and functionality. Upstairs, you’re

    Melissa Menning Alberti Realty, LLC

    46 Boxwood Rd, Annapolis, MD 21403
  • 901 Chesterfield Rd, Annapolis, MD 21401
    901 Chesterfield Rd, Annapolis, MD 21401
    901 Chesterfield Rd, Annapolis, MD 21401
    /62

    $499,900

    • 5 Beds
    • 3 Baths
    • 1,724 Sq Ft

    901 Chesterfield Rd, Annapolis, MD 21401

    Welcome Home to 901 Chesterfield Road!! This Beautifully updated Single family home located in Annapolis has the space you need to create a life you desire. Boasting an array of sleek finishes throughout this 5 Bedroom, 3 Bathroom home has so much to offer!! The main level offers an open concept layout featuring spacious living room, dining area, 3 entry level bedrooms, 2 full bathrooms, and

    Lois Alberti Alberti Realty, LLC

    901 Chesterfield Rd, Annapolis, MD 21401
  • 219 Bowen Ct, Annapolis, MD 21401
    219 Bowen Ct, Annapolis, MD 21401
    219 Bowen Ct, Annapolis, MD 21401
    /58

    $865,000

    • 5 Beds
    • 4.5 Baths
    • 4,601 Sq Ft

    219 Bowen Ct, Annapolis, MD 21401

    Welcome to your dream home in the coveted Bowen Manor neighborhood! This beautifully customized Jamison model is a rare find, offering exceptional design, luxurious upgrades, and a prime location near downtown Annapolis.Step inside to discover a gourmet chef’s kitchen that’s sure to impress, featuring top-of-the-line stainless steel GE Monogram appliances—including a gas cooktop with center

    Jennifer Chino Compass

    219 Bowen Ct, Annapolis, MD 21401
  • 2 River Dr, Annapolis, MD 21403
    2 River Dr, Annapolis, MD 21403
    2 River Dr, Annapolis, MD 21403
    /50

    $4,950,000

    • 6 Beds
    • 4.5 Baths
    • 3,818 Sq Ft

    2 River Dr, Annapolis, MD 21403

    2 River with its stunning water views of the Severn River and of the Chesapeake Bay epitomizes the Annapolis Lifestyle! Located in this beloved multi-generational community of Bay Ridge, this exquisitely renovated classic home seamlessly blends the timeless updates and fabulous original detail such as leaded glass windows and brass chandeliers. The main level has the most incredible, breezy

    Alex Tower Sears TTR Sotheby's International Realty

    2 River Dr, Annapolis, MD 21403
  • 553 Choptank Cove Ct, Annapolis, MD 21401
    553 Choptank Cove Ct, Annapolis, MD 21401
    553 Choptank Cove Ct, Annapolis, MD 21401
    /47

    $1,100,000

    • 5 Beds
    • 4 Baths
    • 3,569 Sq Ft

    553 Choptank Cove Ct, Annapolis, MD 21401

    English Tudor featuring a stone front patio for nature lovers and bird watchers. Surrounded by large trees for tons of shade and a 45 foot rear deck for large gatherings and rear lawn for play areas. Almost 4000 square feet of living space plus an oversized garage 24x25 with a floored attic space above for expansion or storage. The great room has cathedral ceilings, wood beams and wide

    Linda Patterson Long & Foster Real Estate, Inc.

    553 Choptank Cove Ct, Annapolis, MD 21401
  • 2000 Monticello Dr, Annapolis, MD 21401
    2000 Monticello Dr, Annapolis, MD 21401
    2000 Monticello Dr, Annapolis, MD 21401
    /51

    $1,125,000 Open Sun 12PM - 2PM

    • 6 Beds
    • 6.5 Baths
    • 6,612 Sq Ft

    2000 Monticello Dr, Annapolis, MD 21401

    Welcome to this exceptional former model home in the prestigious Monticello enclave—ideally located just moments from Annapolis’ finest dining, shopping, and commuter routes. This residence showcases endless upgrades and over 6,700 square feet of refined living across three spacious levels, blending timeless elegance with cutting-edge comfort.A dramatic two-story foyer with striking

    Peggy Love Long & Foster Real Estate, Inc.

    2000 Monticello Dr, Annapolis, MD 21401
  • 3117 Port Way, Annapolis, MD 21403
    3117 Port Way, Annapolis, MD 21403
    3117 Port Way, Annapolis, MD 21403
    /60

    $847,000

    • 5 Beds
    • 3 Baths
    • 2,288 Sq Ft

    3117 Port Way, Annapolis, MD 21403

    Annapolis Hidden Gem in the Sought-After Anchorage Waterfront Community: Welcome to 3117 Port Way, a beautifully updated home nestled in the highly desirable Anchorage Waterfront community of Annapolis. This spacious 5-bedroom, 3-bathroom residence offers approximately 2,400 square feet of open-concept living space on a 0.34-acre lot, complete with a partially fenced backyard and invisible

    Ani Gonzalez-Brunet Coldwell Banker Realty

    3117 Port Way, Annapolis, MD 21403
  • 86 Summerfield Dr, Annapolis, MD 21403
    86 Summerfield Dr, Annapolis, MD 21403
    86 Summerfield Dr, Annapolis, MD 21403
    /28

    $414,900

    • 5 Beds
    • 2 Baths
    • 2,340 Sq Ft

    86 Summerfield Dr, Annapolis, MD 21403

    ANNAPOLIS lifestyle in this 3 Level Cape Cod, boasting 5 Bedrooms and 2 full Bathrooms. The Beautiful interior showcases contemporary finishes and a thoughtful layout that maximizes both style and functionality. The custom kitchen with quartz countertops, stainless-steel appliances and attractive cabinetry enhances your cooking and gathering experience. Complete with a traditional floor plan

    Barry Lagemann Keller Williams Flagship

    86 Summerfield Dr, Annapolis, MD 21403
  • 1524 Cedar Lane Farm Rd, Annapolis, MD 21409
    1524 Cedar Lane Farm Rd, Annapolis, MD 21409
    1524 Cedar Lane Farm Rd, Annapolis, MD 21409
    /50

    $6,995,000

    • 7 Beds
    • 5.5 Baths
    • 9,024 Sq Ft

    1524 Cedar Lane Farm Rd, Annapolis, MD 21409

    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.

    Brad Kappel TTR Sotheby's International Realty

    1524 Cedar Lane Farm Rd, Annapolis, MD 21409
  • 712 Pearson Point Place, Annapolis, MD 21401
    712 Pearson Point Place, Annapolis, MD 21401
    712 Pearson Point Place, Annapolis, MD 21401
    /44

    $950,000

    • 5 Beds
    • 4.5 Baths
    • 5,184 Sq Ft

    712 Pearson Point Place, Annapolis, MD 21401

    Nestled in sought-after Kingsport, this impeccably maintained residence offers a rare combination of comfort, style, and convenience. Kingsport residents enjoy exclusive access to a private pool, community dock, and beautifully landscaped walking trails—perfect for morning jogs, evening strolls, or weekend paddle-boarding adventures.This expansive home features five generously sized

    Amber Krause TTR Sotheby's International Realty

    712 Pearson Point Place, Annapolis, MD 21401
  • 130 Great Lake Dr, Annapolis, MD 21403
    130 Great Lake Dr, Annapolis, MD 21403
    130 Great Lake Dr, Annapolis, MD 21403
    /71

    $650,000

    • 5 Beds
    • 2.5 Baths
    • 2,014 Sq Ft

    130 Great Lake Dr, Annapolis, MD 21403

    PRIVATE WATER COMMUNITY! 5 BEDROOM 2.5 FULL BATH BRICK HOME SITS ON .42 ACRE LOT IN SOUGHT AFTER HILLSMERE ESTATES! FRESHLY PAINTED THROUGHOUT! UPPER LEVEL HARDWOOD FLOORS HAVE BEEN REFINISHED! UPDATED KITCHEN W/ SS APPLIANCES, QUARTZ COUNTER TOPS, TILED BACKSPLASH, TABLE SPACE W/ BREAKFAST BAR & RECESSED LIGHTING. LIVING ROOM HAS BRICK FIREPLACE AND MANTEL, HARDWOOD FLOORS, BAY WINDOW W/

    Jennifer Drennan Taylor Properties

    130 Great Lake Dr, Annapolis, MD 21403
  • 52 Primrose Hill Ln, Annapolis, MD 21403
    52 Primrose Hill Ln, Annapolis, MD 21403
    52 Primrose Hill Ln, Annapolis, MD 21403
    /64

    $999,999

    • 5 Beds
    • 4.5 Baths
    • 3,978 Sq Ft

    52 Primrose Hill Ln, Annapolis, MD 21403

    NEW PRICE! Live the Annapolis lifestyle just close enough to enjoy in-town living, but tucked away in a quiet little enclave avoiding all the noise and parking challenges in town. The current homeowner refers to Primrose Hill as a serene little gem. Walk to coffee shops and dining hot spots, launch the boat or hop on the water taxi right up the street. This distinguished Georgian-style home

    Michele Deckman TTR Sotheby's International Realty

    52 Primrose Hill Ln, Annapolis, MD 21403
  • 3015 Friends Rd, Annapolis, MD 21401
    3015 Friends Rd, Annapolis, MD 21401
    3015 Friends Rd, Annapolis, MD 21401
    /43

    $3,250,000

    • 6 Beds
    • 6.5 Baths
    • 4,750 Sq Ft

    3015 Friends Rd, Annapolis, MD 21401

    3015 Friends Road is perched on a stunning point of land where the South River meets the protected waters of Boyds Cove. The views down the South River towards the Chesapeake Bay are truly endless! This custom-built home with 456 ft of waterfrontage is everything you’d hope for in a modern waterfront retreat. Built in 2021, it blends contemporary design with the relaxed elegance of coastal living

    Reid Buckley Long & Foster Real Estate, Inc.

    3015 Friends Rd, Annapolis, MD 21401
  • 840 Childs Point Rd, Annapolis, MD 21401
    840 Childs Point Rd, Annapolis, MD 21401
    840 Childs Point Rd, Annapolis, MD 21401
    /126

    $4,450,000

    • 6 Beds
    • 9 Baths
    • 12,374 Sq Ft

    840 Childs Point Rd, Annapolis, MD 21401

    One-of-a-kind Waterfront Luxury in Annapolis, Maryland! Secluded on 2.59 lush, park-like acres along the shores of one of the Chesapeake Bay’s most serene and protected tributaries, this exceptional estate offers an unparalleled blend of privacy, elegance, and premier waterfront living rarely found in Annapolis. From the moment you arrive down the tree-lined drive, a sense of calm and

    David Orso Berkshire Hathaway HomeServices PenFed Realty

    840 Childs Point Rd, Annapolis, MD 21401
  • 1900 Carrollton Rd, Annapolis, MD 21409
    1900 Carrollton Rd, Annapolis, MD 21409
    1900 Carrollton Rd, Annapolis, MD 21409
    /50

    $8,995,000

    • 7 Beds
    • 9 Baths
    • 12,200 Sq Ft

    1900 Carrollton Rd, Annapolis, MD 21409

    Rare opportunity for a true legacy property on the Severn River! Built by Pilli Custom Homes, this home is a masterpiece of craftsmanship. Wake up every morning to the everchanging scenery out your windows, step out onto your private balcony with a freshly brewed coffee from your in-room coffee bar, feeling the gentle river breeze as you watch sailboats drift by. Make your way down via the

    Brad Kappel TTR Sotheby's International Realty

    1900 Carrollton Rd, Annapolis, MD 21409
  • 806 Coachway, Annapolis, MD 21401
    806 Coachway, Annapolis, MD 21401
    806 Coachway, Annapolis, MD 21401
    /43

    $7,850,000

    • 5 Beds
    • 8 Baths
    • 12,635 Sq Ft

    806 Coachway, Annapolis, MD 21401

    Welcome to your luxury waterfront sanctuary on the Severn River, located in the highly coveted Downs on the Severn community of Annapolis. This extraordinary estate offers unmatched amenities including a private sport court, heated saltwater pool, and private pier with a tram to easily transport you and your guests to the water’s edge for unforgettable days on the Bay. Inside, the craftsmanship

    Brad Kappel TTR Sotheby's International Realty

    806 Coachway, Annapolis, MD 21401
  • 1741 Holly Beach Farm Rd, Annapolis, MD 21409
    1741 Holly Beach Farm Rd, Annapolis, MD 21409
    1741 Holly Beach Farm Rd, Annapolis, MD 21409
    /35

    $3,800,000

    • 5 Beds
    • 3 Baths
    • 2,775 Sq Ft

    1741 Holly Beach Farm Rd, Annapolis, MD 21409

    Rare Waterfront Opportunity! Escape to your waterfront farmhouse retreat. Nestled on 3.5 picturesque acres overlooking the tranquil waters of protected Moss Pond, this charming historic property offers big views of and direct access to the Chesapeake Bay. Originally part of a working thoroughbred racehorse farm, this home is surrounded by parkland and privacy while still close to the city.

    David Orso Berkshire Hathaway HomeServices PenFed Realty

    1741 Holly Beach Farm Rd, Annapolis, MD 21409
  • 2680 Claibourne Ct, Annapolis, MD 21403
    2680 Claibourne Ct, Annapolis, MD 21403
    2680 Claibourne Ct, Annapolis, MD 21403
    /67

    $2,695,000

    • 5 Beds
    • 4 Baths
    • 3,415 Sq Ft

    2680 Claibourne Ct, Annapolis, MD 21403

    Nestled on Chase Pond along the serene shores of the Chesapeake Bay, 2680 Claibourne Court offers an unparalleled waterfront living experience. This meticulously renovated coastal contemporary-style residence boasts 5 bedrooms, 4 full bathrooms, and seamlessly blends luxury with comfort. Set on a generous 2.62-acre waterfront lot, the property features a private pier with boat lifts and a beach,

    Doc Keane Washington Fine Properties, LLC

    2680 Claibourne Ct, Annapolis, MD 21403
  • 746 Warren Dr, Annapolis, MD 21403
    746 Warren Dr, Annapolis, MD 21403
    746 Warren Dr, Annapolis, MD 21403
    /47

    $524,900 Open Sun 12PM - 3PM

    • 5 Beds
    • 1.5 Baths
    • 1,200 Sq Ft

    746 Warren Dr, Annapolis, MD 21403

    Price Reduced! Welcome to 746 Warren Drive Annapolis, Maryland —nestled just a block and a half from Back Creek in the highly desirable Greenacres community of Eastport. This charming 5-bedroom, 1.5-bath home sits on a generous lot along a quiet street, offering both privacy and water access. Enjoy first-floor living with a freshly painted interior and exterior, brand new carpet

    Brian Jacobs Coldwell Banker Realty

    746 Warren Dr, Annapolis, MD 21403
  • 1576 Bay Head Rd, Annapolis, MD 21409
    1576 Bay Head Rd, Annapolis, MD 21409
    1576 Bay Head Rd, Annapolis, MD 21409
    /68

    $3,475,000

    • 6 Beds
    • 5.5 Baths
    • 6,732 Sq Ft

    1576 Bay Head Rd, Annapolis, MD 21409

    Boating season is here! Incredible opportunity - Seller will hold a 10% second mortgage at 5.87% for five years if you are putting a minimum of 20% down! Welcome to 1576 Bay Head Road, an exceptional waterfront estate where luxury living meets the ultimate Chesapeake Bay lifestyle. Perfectly situated on a private one-acre lot along the calm, protected waters of the Little Magothy River, this

    Wendy Oliver Coldwell Banker Realty

    1576 Bay Head Rd, Annapolis, MD 21409
  • 803 Coachway, Annapolis, MD 21401
    803 Coachway, Annapolis, MD 21401
    803 Coachway, Annapolis, MD 21401
    /112

    $6,750,000

    • 6 Beds
    • 8.5 Baths
    • 11,045 Sq Ft

    803 Coachway, Annapolis, MD 21401

    This Severn River Waterfront Estate is a rare and breathtaking Annapolis retreat. Experience the ultimate in waterfront living in this exquisite residence, a true masterpiece offering unparalleled panoramic water views. Nestled on a pristine one-acre site in the prestigious Point of The Downs, this custom-built legacy home has been meticulously updated to perfection, creating the ideal setting

    Georgie Berkinshaw Coldwell Banker Realty

    803 Coachway, Annapolis, MD 21401
  • 201 Janwall St, Annapolis, MD 21403
    201 Janwall St, Annapolis, MD 21403
    201 Janwall St, Annapolis, MD 21403
    /35

    $550,000

    • 6 Beds
    • 2 Baths
    • 2,039 Sq Ft

    201 Janwall St, Annapolis, MD 21403

    Sellers prefer Original Title & Escrow, LLC. Welcome to this beautifully maintained corner ranch in Eastport, MD, with easy access to Downtown Annapolis. No HOA fees! The bathrooms have been remodeled, and the appliances are stainless steel. This home offers two levels of comfortable living space, with three bedrooms and a full bathroom on the upper level, and the same living space in the

    Madeleine Melgar Alltrade Real Estate

    201 Janwall St, Annapolis, MD 21403

Showing Results 1 - 40, Page 1 of 2

Maryland Annapolis

5-Bedroom Homes for Sale in Annapolis, MD

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In Annapolis, there are currently 56 5-bedroom homes for sale, offering expansive and versatile living spaces suitable for larger families or those desiring ample room for guests, home offices, or recreational areas. These properties provide flexibility and comfort, with generous bedroom counts accommodating various living arrangements and lifestyle needs. Whether you're in search of a spacious single-family home, a luxurious estate, or a custom-built residence with five or more bedrooms, there are options to cater to different lifestyles. Explore the selection of 5-bedroom homes for sale in Annapolis and find the perfect place to meet your needs.

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