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Colonial Homes for Sale in Annapolis, MD

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  • /68

    $890,000

    $100K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,542 Sq Ft

    1469 Pleasant Lake Rd, Annapolis, MD 21409

    PRICE REDUCTION!OPEN HOUSE SATURDAY 8/15/2026 from 12-2pm!Rarely does a home offer this combination of privacy, space, water access, and convenience. Set on more than half an acre in the desirable Pleasant Plains community, this exceptional property features neighborhood beach access, a heated and cooled three-car garage, and highly sought-after Broadneck schools—all just minutes from

    Kevin Stodd EXP Realty, LLC

    1469 Pleasant Lake Rd, Annapolis, MD 21409
  • /42

    $1,285,000

    • 3 Beds
    • 2.5 Baths
    • 1,928 Sq Ft

    1105 Boucher Ave, Annapolis, MD 21403

    Nestled in the heart of Eastport, this thoughtfully designed 3-bedroom, 2.5-bath home offers the perfect combination of comfortable living, modern updates, and one of Annapolis' most sought-after walkable locations. Complete with a rare detached two-car garage, this is an exceptional opportunity to enjoy the Eastport lifestyle in an established neighborhood that continues to attract significant

    Teresa Klem Long & Foster Real Estate, Inc.

    1105 Boucher Ave, Annapolis, MD 21403
  • /98

    $1,699,000

    Open Sat 12PM - 2PM $101K PRICE DROP
    • 5 Beds
    • 5.5 Baths
    • 4,648 Sq Ft

    1322 Windsor Ridge Ln, Annapolis, MD 21409

    ** PRICE IMPROVEMENT** GREAT OPPORTUNITY TO OWN A PRIVATE LUXURY ESTATE ON THE BROADNECK PENINSULA!! Built in 2001, this stately brick Koch Colonial offers 4,648 square feet above grade and is nestled on a private 5.73-acre cul-de-sac lot in the highly sought-after Broadneck School District, delivering the perfect blend of luxury, privacy, and timeless elegance. Featuring a stunning 2022 gourmet

    Elizabeth DuLaney EXP Realty, LLC

    1322 Windsor Ridge Ln, Annapolis, MD 21409
  • /103

    $1,500,000

    New Construction
    • 5 Beds
    • 4.5 Baths
    • 5,437 Sq Ft

    1907 Mackiebeth Ct, Annapolis, MD 21401

    This is a rare opportunity to own a newly built, beautifully designed home on a large lot in an established neighborhood-with nature at your doorstep and everything Annapolis has to offer just minutes away. This home is ready to go and can do a quick occupancy! With a stunning Colonial architectural style, this beautiful home offers 5-bedrooms and 4.5-baths and sits on the last available lot in

    Marilyn Hendley EXP Realty, LLC

    1907 Mackiebeth Ct, Annapolis, MD 21401
  • /83

    $3,000,000

    • 5 Beds
    • 2 Baths
    • 5,522 Sq Ft

    1979 Baltimore Annapolis Blvd, Annapolis, MD 21409

    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

    Alison Wisnom Coldwell Banker Realty

    1979 Baltimore Annapolis Blvd, Annapolis, MD 21409
  • /25

    $1,199,500

    Open Sat 11AM - 2PM
    • 5 Beds
    • 5 Baths
    • 5,086 Sq Ft

    1711 Ritchie Hwy, Annapolis, MD 21409

    Beautiful colonial home in the perfect Annapolis location. Nestled 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

    Kay Millett Taylor Properties

    1711 Ritchie Hwy, Annapolis, MD 21409
  • /38

    $949,000

    Open Fri 12:30PM - 2:30PM $51K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 2,912 Sq Ft

    112 Speicher Dr, Annapolis, MD 21401

    Turn key and thoughtfully updated, this 5-bedroom, 4.5-bath single-family home offers a rare combination of spacious living, modern upgrades, and resort-style outdoor amenities in Annapolis. This impressive property features an attached two-car garage, a private in-ground pool, and a pool house. In addition, there is a rear entry 2 bedroom apartment with its own private deck.The spacious

    Christine Leonard Redfin Corp

    112 Speicher Dr, Annapolis, MD 21401
  • /41

    $835,000

    • 3 Beds
    • 2.5 Baths
    • 1,512 Sq Ft

    16 Woodlawn Ave, Annapolis, MD 21401

    Tucked into Homewood, just beyond the brick sidewalks of Historic Downtown Annapolis, 16 Woodlawn Avenue is a residence taken down to the studs and rebuilt in 2019, blending all the comforts of modern design with the historic charm of Homewood. A traditional front porch, turned white columns and soft buttery siding announce the home from the street while a long driveway offers the rare luxury of

    Michele Deckman TTR Sotheby's International Realty

    16 Woodlawn Ave, Annapolis, MD 21401
  • /51

    $2,295,000

    $155K PRICE DROP
    • 5 Beds
    • 4 Baths
    • 3,178 Sq Ft

    83 Market St, Annapolis, MD 21401

    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

    Elizabeth Dooner Coldwell Banker Realty

    83 Market St, Annapolis, MD 21401
  • /50

    $685,000

    $10K PRICE DROP
    • 2 Beds
    • 1.5 Baths
    • 1,040 Sq Ft

    34 Pinkney St, Annapolis, MD 21401

    This is the perfect pied-à-terre and an excellent investment property with its extremely successful long-term rental history! Lots of recent updates, including New HVAC -2025 and new metal roof- 2020. Cozy living room flows to the dining with fun shiplap walls and built-in seating. The well-planned renovated kitchen has access to the private brick courtyard, just the right size for a lovely

    Alex Tower Sears TTR Sotheby's International Realty

    34 Pinkney St, Annapolis, MD 21401
  • /47

    $585,000

    Open Sat 10AM - 12PM
    • 3 Beds
    • 2.5 Baths
    • 2,050 Sq Ft

    1055 Sun Valley Dr, Annapolis, MD 21409

    Welcome to 1055 Sun Valley Drive, a beautifully cared‑for Colonial in Cape St. Claire that blends thoughtful updates, flexible living space, and Broadneck Peninsula convenience. This 3BR/2.5BA home offers approximately 2,050 finished square feet. Built in 1989, the property is newer than many surrounding homes and features public water/sewer, electric heat, and an attached garage.The heart of

    Loren Edelstein Long & Foster Real Estate, Inc.

    1055 Sun Valley Dr, Annapolis, MD 21409
  • /62

    $559,900

    • 4 Beds
    • 4 Baths
    • 2,044 Sq Ft

    633 Snow Goose Ln, Annapolis, MD 21409

    Exceptional 4-story townhome in the highly sought-after, water-privileged community of Woods Landing! Thoughtfully renovated from top to bottom, this beautifully appointed home offers the perfect blend of timeless style, functional living, and an unbeatable location.From the moment you step inside, you'll appreciate the light-filled interior, soaring 9-foot ceilings, gorgeous updated

    GABRIELLA VIDRO Douglas Realty, LLC

    633 Snow Goose Ln, Annapolis, MD 21409
  • /69

    $599,000

    • 4 Beds
    • 2.5 Baths
    • 1,880 Sq Ft

    402 S Cherry Grove Ave, Annapolis, MD 21401

    Welcome to Heritage, a sought-after Annapolis community where space, comfort, and convenience come together! This beautifully refreshed three-level Colonial offers four bedrooms, multiple living spaces, a huge fully fenced backyard, and an impressive list of recent updates—making it truly move-in ready.Step inside to fresh paint, new carpet and LVP flooring, updated fixtures and hardware,

    Michelle Triolo Compass

    402 S Cherry Grove Ave, Annapolis, MD 21401
  • /71

    $475,000

    Open Sun 4PM - 6PM $25K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,880 Sq Ft

    1099 Linden Tree Dr, Annapolis, MD 21409

    Welcome to 1099 Linden Tree Drive, an incredible opportunity to own a four-bedroom, two-full-bath colonial in the desirable waterfront community of Cape St. Claire! Offering approximately 1,880 finished square feet, this home provides a functional layout with plenty of room for everyday living, working from home and entertaining. Several important updates have already been completed, including a

    Juliet Brooke Samson Properties

    1099 Linden Tree Dr, Annapolis, MD 21409
  • /70

    $899,900

    Open Sat 11AM - 1PM
    • 4 Beds
    • 3.5 Baths
    • 3,920 Sq Ft

    810 Moran Dr, Annapolis, MD 21401

    Welcome home! 810 Moran Drive is a beautifully updated home in the highly desirable Monticello community, offering over 3,900 finished square feet of thoughtfully designed living space in one of Annapolis' most convenient locations. Just minutes from Historic Downtown Annapolis, the Naval Academy, shopping, dining, commuter routes, and waterfront attractions, this home perfectly blends comfort,

    Kellie Gough McLendon Long & Foster Real Estate, Inc.

    810 Moran Dr, Annapolis, MD 21401
  • /10

    $439,500

    Coming Soon Sep 11
    • 2 Beds
    • 2.5 Baths
    • 1,934 Sq Ft

    2700 Summerview Way Unit 304, Annapolis, MD 21401

    More info and photos coming soon!

    Jason Donovan RE/MAX Leading Edge

    2700 Summerview Way Unit 304, Annapolis, MD 21401
  • /44

    $489,000

    • 2 Beds
    • 1 Bath
    • 1,190 Sq Ft

    1005 Hyde Park Dr, Annapolis, MD 21403

    Welcome to this lovely 2-bedroom, 1-bathroom home in the heart of Annapolis, offering classic charm and modern updates throughout. Featuring beautiful hardwood floors and a traditional layout, this home provides comfort and functionality in every room. The updated kitchen boasts a center island, granite and a spacious pantry all perfect for meal prep or casual dining. The bathroom has been

    Michael Simi Douglas Realty LLC

    1005 Hyde Park Dr, Annapolis, MD 21403
  • /95

    $1,550,000

    $50K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,788 Sq Ft

    718 Whitehall Beach Rd, Annapolis, MD 21409

    Price Improvement and Exceptional Value! A rare opportunity to own over 2 private acres in one of Annapolis’ most desirable waterfront communities. Complete with a private tennis court and backing to a sprawling horse farm, this exceptional property offers the perfect blend of privacy, recreation, and the Chesapeake lifestyle. Nestled in the sought-after Whitehall Beach neighborhood, residents

    Joanna Dalton Coldwell Banker Realty

    718 Whitehall Beach Rd, Annapolis, MD 21409
  • /53

    $849,999

    $25K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,340 Sq Ft

    1070 Foxcroft Run, Annapolis, MD 21401

    Tucked away on a quiet, wooded homesite, this beautiful 4BR/3.5BA single-family home offers the perfect combination of privacy, space, and natural beauty. Sunlight fills all three finished levels, creating a bright and inviting atmosphere throughout.The upper level features three bedrooms, including a spacious primary suite with a beautiful luxury bath, dressing room, new wood flooring,

    Louis Pope Trademark Realty, Inc

    1070 Foxcroft Run, Annapolis, MD 21401
  • /43

    $1,199,000

    • 3 Beds
    • 4 Baths
    • 1,476 Sq Ft

    145 Prince George St, Annapolis, MD 21401

    Welcome to 145 Prince George St., a distinctive historic home that blends classic architectural character with thoughtful modern updates. From its welcoming front porch and slate roof to its original wood details and spacious interior, this home offers a rare combination of charm, character, and versatility. The main level features beautiful wood floors and an inviting floor plan designed for

    Dan Iampieri RE/MAX Aspire

    145 Prince George St, Annapolis, MD 21401
  • /12

    $385,000

    • 3 Beds
    • 2.5 Baths
    • 1,516 Sq Ft

    95 Harbour Heights Dr, Annapolis, MD 21401

    PHOTOS COMING . This sun-filled home is located in the lovely Harbour Heights. Awaiting your special touch, this home features hardwood floors, crown molding, granite kitchen counters, stainless steel appliances and a deck that backs to trees. The Owner's suite has vaulted ceilings and a spacious walk-in closet. Close to restaurants and shopping, Rt 50 and minutes from downtown Annapolis and

    Novera King Samson Properties

    95 Harbour Heights Dr, Annapolis, MD 21401
  • /135

    $1,999,900

    • 4 Beds
    • 4.5 Baths
    • 3,062 Sq Ft

    120 Island View Dr, Annapolis, MD 21401

    Prepare to be amazed by this rare waterfront opportunity offering 4 bedrooms, 4.5 baths with over 3000 square feet of living space with approximately 270-degree panoramic views of Gingerville Creek. Situated at the end of a quiet cul-de-sac, this exceptional property combines luxury, privacy, and an unbeatable location just minutes from Annapolis. Commuters will love the convenience of being just

    Boyd Grainger Pearson Smith Realty, LLC

    120 Island View Dr, Annapolis, MD 21401
  • /81

    $500,000

    • 4 Beds
    • 2.5 Baths
    • 2,738 Sq Ft

    318 Beach Dr, Annapolis, MD 21403

    This 4-bedroom, 2.5-bath detached Colonial in Hillsmere Estates offers a spacious three-level layout with an eat-in kitchen, family room, sunroom, fenced backyard, and partially finished walkout lower level. Additional features include a primary suite with a private bath and sitting area, a wood-burning fireplace, hardwood flooring, an asphalt driveway, and access to community beaches, picnic

    Lee Tessier EXP Realty, LLC

    318 Beach Dr, Annapolis, MD 21403
  • /25

    $265,000

    $29K PRICE DROP
    • 2 Beds
    • 2 Baths

    5 Silverwood Cir Unit 1, Annapolis, MD 21403

    1312 Square Ft Condo in Fairwinds of Annapolis ***NEW HVAC November 2024*** NEW LIGHTING 2024***NEW ELECTRICAL PANEL 2026 ***New shower glass door in master bathroom Popular Fairwinds Condo is a great place to live!! Two Bedroom Two Bath WITH DEN condominium ! Newer stainless steel appliances ! Freshly painted 2026 ! Luxury Vinyl thru living areas and carpet in bedrooms! Lots of closets and

    Bev Langley Coldwell Banker Realty

    5 Silverwood Cir Unit 1, Annapolis, MD 21403
  • /48

    $699,000

    $26K PRICE DROP
    • 4 Beds
    • 5 Baths
    • 2,500 Sq Ft

    103 Norma Aly, Annapolis, MD 21403

    Some homes ask you to spend your weekends maintaining them. This one gives your weekends back. Imagine finishing work on Friday, closing the garage door, and deciding whether the evening calls for dinner in Eastport, cocktails downtown, a concert at City Dock, or simply inviting friends over because your house was built for exactly that. The heart of the home is a kitchen that doesn't hide the

    Wendy Oliver Coldwell Banker Realty

    103 Norma Aly, Annapolis, MD 21403
  • /92

    $3,849,000

    • 6 Beds
    • 4.5 Baths
    • 4,474 Sq Ft

    16 Maryland Ave, Annapolis, MD 21401

    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

    Joanna Dalton Coldwell Banker Realty

    16 Maryland Ave, Annapolis, MD 21401
  • /46

    $2,685,000

    $295K PRICE DROP
    • 5 Beds
    • 4.5 Baths
    • 5,082 Sq Ft

    3733 Thomas Point Rd, Annapolis, MD 21403

    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

    Brad Kappel TTR Sotheby's International Realty

    3733 Thomas Point Rd, Annapolis, MD 21403
  • /35

    $539,000

    • 3 Beds
    • 2.5 Baths
    • 1,524 Sq Ft

    1529 Ritchie Ln, Annapolis, MD 21401

    Nestled in the sought-after Southwoods community just off West Street, this beautifully updated single-family home offers the perfect blend of comfort, style, and convenience with easy access to everything Annapolis has to offer. Inside, luxury vinyl plank flooring flows throughout the inviting two-story floor plan featuring arched entryways, a cozy fireplace, and flexible living spaces designed

    Dee Dee Miller Paul Wesley Real Estate

    1529 Ritchie Ln, Annapolis, MD 21401
  • /40

    $1,575,000

    • 4 Beds
    • 3.5 Baths
    • 2,372 Sq Ft

    268 King George St, Annapolis, MD 21401

    Nestled along one of the most prestigious streets in Historic Annapolis, 268 King George Street presents a rare opportunity to own a beautifully renovated residence just steps from the U.S. Naval Academy, St. John's College, City Dock, Main Street, Spa Creek, and the Chesapeake Bay. Offering the perfect blend of historic charm and sophisticated modern living, this exceptional home places you at

    Carol Snyder Monument Sotheby's International Realty

    268 King George St, Annapolis, MD 21401
  • /56

    $1,294,880

    New Construction $89K PRICE DROP
    • 6 Beds
    • 4 Baths
    • 3,702 Sq Ft

    2644 Claibourne Rd, Annapolis, MD 21403

    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

    George Bailey Keller Williams Flagship

    2644 Claibourne Rd, Annapolis, MD 21403
  • /35

    $429,000

    $6K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,810 Sq Ft

    73 Gentry Ct, Annapolis, MD 21403

    A rare find in the heart of Annapolis! This truly move-in ready home features three bedrooms, two and half baths, and a modern kitchen with new electric range and generous living space throughout. Many major improvements have been completed for you within the past five years, providing added peace of mind. These include a new roof, LVP flooring throughout the main level, a basement waterproofing

    Jonathan Minerick Homecoin.com

    73 Gentry Ct, Annapolis, MD 21403
  • /2

    $1,250,000

    Open House 9/26 Coming Soon Sep 25
    • 5 Beds
    • 6 Baths
    • 6,244 Sq Ft

    912 Plattner Ct, Annapolis, MD 21401

    Welcome to 912 Plattner Court in Annapolis’s Overlook at Broad Creek neighborhood, an elegant stone-front Colonial offering 5 bedrooms, 4.5 baths, and approximately 4,400 square feet above grade. Set on a half-acre of manicured grounds backing to forest land, the home features a spacious main level primary suite, a 20-by-40-foot Gunite pool with waterfall, and abundant indoor and outdoor living

    Richard Thompson Long & Foster Real Estate, Inc.

    912 Plattner Ct, Annapolis, MD 21401
  • /47

    $1,950,000

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

    192 Duke of Gloucester St, Annapolis, MD 21401

    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

    Hanh Pham Samson Properties

    192 Duke of Gloucester St, Annapolis, MD 21401

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