Annapolis, MD Homes for Sale with Garage

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  $845,000

  $154K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 1,506 Sq Ft

  278 Hillsmere Dr, Annapolis, MD 21403

  Serious price adjustment. Location, location, location! Stay tuned for new interior photos. This home is located in the highly desirable Hillsmere Shores community, offering a private beach, community pool, marina, and multiple launch areas for boats, kayaks, canoes, and paddleboards — the perfect setting for anyone who loves life on the water. The home features four spacious bedrooms and three

  Tommy Eicher Coldwell Banker Realty

  278 Hillsmere Dr, Annapolis, MD 21403
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  $2,980,000

  • 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
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  $745,000

  $30K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 4,497 Sq Ft

  211 N Pindell Ave, Annapolis, MD 21401

  Tucked just off Poplar Trail, 211 Pindell Avenue is a classic brick rancher that lives far larger than expected—4,497 square feet of light-filled, entertainer-ready space waiting to be enjoyed. Inside, walls of oversized windows pour sunshine across hardwood floors and custom trim. The living room rises to a vaulted ceiling anchored by a wood-burning fireplace, while the dining room charms with a

  June Steinweg Long & Foster Real Estate, Inc.

  211 N Pindell Ave, Annapolis, MD 21401
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  $499,900

  $75K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,390 Sq Ft

  1407 Brenwoode Rd, Annapolis, MD 21409

  "NOW OFFERED AT $499,900 — A rare opportunity to own over 2,000 square feet on the Broadneck Peninsula for under $500,000." NOW OFFERED AT $499,900 — One of the best values on the Broadneck Peninsula! This spacious split-level home offers over 2,000 square feet of living space in one of Annapolis' most desirable waterfront-oriented communities. Featuring 3 bedrooms, 2 full baths, and a finished

  Andrea Scheidt Engel & Völkers Annapolis

  1407 Brenwoode Rd, Annapolis, MD 21409
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  $1,348,880

  New Construction $35K 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 corner lot and

  George Bailey Keller Williams Flagship

  2644 Claibourne Rd, Annapolis, MD 21403
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  /23

  $315,000

  • 1 Bed
  • 1.5 Baths
  • 1,000 Sq Ft

  7101 Bay Front Dr Unit 202, Annapolis, MD 21403

  Experience the Baywoods lifestyle from Unit #202, a beautifully located 1BR/1.5BA cooperative residence in the sought-after Baywoods community of Annapolis. Nestled along the beautiful Chesapeake Bay, Baywoods offers residents the perfect blend of waterfront beauty, maintenance-free living, and a vibrant retirement lifestyle. Unit #202 is ideally located in the North Tower, just steps from the

  Ruth McGovern Long & Foster Real Estate, Inc.

  7101 Bay Front Dr Unit 202, Annapolis, MD 21403
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  $499,999

  $25K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,485 Sq Ft

  1915 Towne Centre Blvd Unit 502, Annapolis, MD 21401

  This exceptional 5th-floor condo offers a one-of-a-kind, unique floor plan with breathtaking panoramic views and an abundance of natural light from its sunny southern exposure. Featuring two generously sized bedrooms with expansive closets, this upscale residence combines comfort and style. Inside, you’ll find beautiful hardwood floors, soaring 10-foot ceilings, and elegant granite countertops

  David Yee Coldwell Banker Realty

  1915 Towne Centre Blvd Unit 502, Annapolis, MD 21401
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  $650,000

  $9K PRICE DROP

  • 5 Beds
  • 3.5 Baths
  • 3,326 Sq Ft

  2576 Hidden Cove Rd Unit 154, Annapolis, MD 21401

  Hidden Cove has no Age Restrictions. Fully updated and move-in ready, this impressive 5-bedroom, 3.5-bath home offers a finished lower level complete with a bedroom and full bath—ideal for guests, extended living, or a private retreat. The 2022 renovated kitchen is the heart of the home, featuring quartz countertops, soft-close cabinetry, and premium Samsung appliances, seamlessly connecting to

  Debra Gasch Redfin Corp

  2576 Hidden Cove Rd Unit 154, Annapolis, MD 21401
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  $475,000

  • 1 Bed
  • 1 Bath
  • 839 Sq Ft

  5 Park Place Unit 431, Annapolis, MD 21401

  Discover the perfect blend of comfort and convenience in this charming 1-bedroom, 1-bathroom condo, ideally situated in the vibrant Park Place community. Built in 2007, this unit features an entry-level bedroom and elevators in the building for easy access. Faces West for sunset views. Enjoy modern living with a fully equipped kitchen boasting a built-in microwave, gas oven/range, dishwasher, and

  Elizabeth Heinsohn Long & Foster Real Estate, Inc.

  5 Park Place Unit 431, Annapolis, MD 21401
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  $2,650,000

  • 6 Beds
  • 4.5 Baths
  • 5,918 Sq Ft

  529 Lee Cir, Annapolis, MD 21403

  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

  Ani Gonzalez-Brunet Coldwell Banker Realty

  529 Lee Cir, Annapolis, MD 21403
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  /53

  $2,950,000

  New Construction

  • 4 Beds
  • 3.5 Baths
  • 4,466 Sq Ft

  703 Glendon Ave, Annapolis, MD 21403

  TO BE BUILT, luxury home on Back Creek adjacent to Eastport. Quiet dead end street. Only steps away from the community marina with deep water slips. Permits in process for home and private pier. Primary suite on the main level. 5075 sq/ft of finished living space. Intentionally designed large home that can also live small when guests are away. 5br 4.5 Bath with 2 car garage. Offering includes 10'

  Colleen Smith EXP Realty, LLC

  703 Glendon Ave, Annapolis, MD 21403
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  $1,899,900

  Open Sun 12PM - 2PM $100K PRICE DROP

  • 4 Beds
  • 4 Baths
  • 3,620 Sq Ft

  3712 Gateshead Dr, Annapolis, MD 21403

  Price reduced, incredible price for Waterfront in prestigious Watergate! Check the comps! Overlooking the protected “hurricane hole” of Watergate Harbor with direct access to the South River near Thomas Point, 3712 Gateshead Drive offers the ultimate lifestyle with waterviews from every room in the home. Located on a street with homes valued at $4 million to $7 million, you get the waterfront

  Melissa Murray Compass

  3712 Gateshead Dr, Annapolis, MD 21403
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  $775,000

  $25K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,464 Sq Ft

  1709 Point no Point Dr, Annapolis, MD 21401

  Major $25,000 price improvement — an incredible opportunity to own a private contemporary retreat in Annapolis! Tucked into one of the area’s most peaceful and private wooded settings, 1709 Point No Point Road offers a rare combination of total seclusion and unbeatable convenience. From the moment you arrive, the striking contemporary architecture, soaring skylights, and walls of windows connect

  Whitney Ward Berkshire Hathaway HomeServices PenFed Realty

  1709 Point no Point Dr, Annapolis, MD 21401
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  /39

  $865,000

  • 5 Beds
  • 4.5 Baths
  • 3,586 Sq Ft

  730 Crisfield Way, Annapolis, MD 21401

  Welcome to Kingsport—where timeless elegance meets waterfront living. Nestled within this coveted, water-privileged community, this exceptional 5-bedroom, 4.5-bath residence offers a seamless blend of sophistication, comfort, and everyday luxury.A grand entry welcomes you with rich hardwoods and graceful architectural details, leading to a formal oval dining room, refined living room, and a

  Amanda Callahan Long & Foster Real Estate, Inc.

  730 Crisfield Way, Annapolis, MD 21401
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  $1,100,000

  • 4 Beds
  • 4.5 Baths
  • 4,032 Sq Ft

  216 Bowen Ct, Annapolis, MD 21401

  Stately brick traditional in sought-after Bowen Manor community. - Turn key,move- in ready just minutes from Historic Annapolis, major commuter routes, and marinas. Offering spacious, bright living throughout. Built with numerous custom upgrades and additions by the original owner, this beautifully maintained residence combines timeless elegance with thoughtful design and very low maintenance

  Connie Cadwell Coldwell Banker Realty

  216 Bowen Ct, Annapolis, MD 21401
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  /54

  $6,500,000

  • 7 Beds
  • 8.5 Baths
  • 9,026 Sq Ft

  2562 Carrollton Rd, Annapolis, MD 21403

  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

  Scott Schuetter Berkshire Hathaway HomeServices PenFed Realty

  2562 Carrollton Rd, Annapolis, MD 21403
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  $300,000

  • 1 Bed
  • 1 Bath
  • 1,000 Sq Ft

  7101 Bay Front Dr Unit 301, Annapolis, MD 21403

  Perhaps the finest Annapolis has to offer...A premiere, resort style retirement living option for those 60+ Time to let someone one else take care of the daily cooking and cleaning, you only need to relax, socialize with your friends and enjoy all Annapolis, Md has to offer! One monthly fee takes care of ALL utilities, daily meal, weekly cleaning, taxes, insurance, garage parking,

  Diane Gavin Coldwell Banker Realty

  7101 Bay Front Dr Unit 301, Annapolis, MD 21403
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  $989,000

  • 8 Beds
  • 4 Baths
  • 3,108 Sq Ft

  1422 West St, Annapolis, MD 21401

  One of Homewood’s most distinctive homes, this 8-bedroom, 4-bath residence offers over 3,100 square feet and a truly unique story. Once known as the “Gables Tourist Home” Bed & Breakfast, the property (built in 1938) still carries subtle nods to its past—including the numbered bedroom doors—while the current owners have thoughtfully updated the interiors and major systems for comfortable modern

  Rachel Holmes Coldwell Banker Realty

  1422 West St, Annapolis, MD 21401
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  $698,999

  $21K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,723 Sq Ft

  78 Old Mill Bottom Rd N Unit 211, Annapolis, MD 21409

  PRICE IMPROVEMENT! MOTIVATED SELLERS!! Experience refined living in this stunning second-floor corner residence, a brand-new 2024-built condominium offering 1,723 square feet of beautifully designed living space filled with natural light. Formerly the community’s model home, this exceptional residence showcases designer finishes, thoughtful upgrades, and meticulous attention to detail throughout.

  Shannon Thayer Douglas Realty, LLC

  78 Old Mill Bottom Rd N Unit 211, Annapolis, MD 21409

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