40,686

Annapolis, MD Homes

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  • /20

    $390,000 Pending

    • 2 Beds
    • 2.5 Baths
    • 1,319 Sq Ft

    933 Breakwater Dr, Annapolis, MD 21403

    This spacious and well-maintained townhouse offers comfortable living in a highly desirable Annapolis location. The main level features a welcoming living room centered around a classic wood-burning fireplace, creating a warm focal point and cozy atmosphere, while the French doors provide access to the backyard, allowing natural light to fill the space while offering an easy transition to outdoor

    Agent Photo

    Scott Smolen

    RE/MAX Leading Edge

    (443) 323-0308

    933 Breakwater Dr, Annapolis, MD 21403
  • /39

    $3,150 per month

    • 3 Beds
    • 2 Baths
    • 1,555 Sq Ft
    • House for Rent

    1252 Creek Dr, Annapolis, MD 21403

    Stunning Oyster Harbor Rental – Coastal Charm Meets Comfort This gorgeous rental blends comfort, charm, and the best of coastal living. Nestled in the highly desirable Oyster Harbor community, residents enjoy water privileges and access to a sandy beach, picnic area, fishing pier, and playground—all just a short walk from the front door. Additional amenities include a community marina, boat ramp,

    Jessica Ricciardi Welder Keller Williams Flagship

    1252 Creek Dr, Annapolis, MD 21403
  • /33

    $1,161,840 Sold Dec 24, 2025

    103 Stilly Way, Annapolis, MD 21403

    • 5 Beds
    • 5.5 Baths
    • 5,200 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • $223/SF
    • 5 Days On Market

    Current Estimated Value $1,107,936

    Lennar Parkeside Preserve - Manor

    103 Stilly Way, Annapolis, MD 21403
    • /27

      Est $342,592 Not Listed For Sale

      169 Brightwater Dr, Annapolis, MD 21401

      • 3 Beds
      • 4 Baths
      • 1,452 Sq Ft
      • Built 2000
      169 Brightwater Dr, Annapolis, MD 21401

      Last Sold Summary

      • 2% Above List Price
      • $231/SF
      • 21 Days On Market

      Last Sold Price $335,000

      Last Listing Agent Daniel Register Creig Northrop Team of Long & Foster

  • /53

    $624,999 Pending

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

    2820 Pennypond Ln N, Annapolis, MD 21401

    OPEN HOUSE CANCELED. UNDER CONTRACT. Welcome to 2820 Pennypond Ln, a rare end-of-row townhome occupying a premium position within the neighborhood. The home is tucked against a private, natural buffer that provides a surprisingly peaceful and private setting not typically found in a townhome community. The home’s side-entry design enhances the sense of privacy, opening into a bright, voluminous

    Agent Photo

    Charles Dwayne Hoyt

    Berkshire Hathaway HomeServices PenFed Realty

    (410) 364-4389

    2820 Pennypond Ln N, Annapolis, MD 21401
  • /18

    $2,330 - $6,457 total monthly price

    Aventon Annapolis

    Studio - 2 Beds

    2553 Riva Rd, Annapolis, MD 21401

    Aventon Annapolis is where convenience, connectivity and comfort collide. Its where youre minutes from numerous shopping and dining options, downtown and the Chesapeake, and where the bustle of Baltimore and D.C. are an easy commute away. Its where your home is filled with modern high-end finishes and thoughtful details.

    2553 Riva Rd, Annapolis, MD 21401
  • /14

    $230,000 Sold May 30, 2025

    20 Amberstone Ct Unit B, Annapolis, MD 21403

    • 3 Beds
    • 2 Baths
    • 1,246 Sq Ft
    • Built 1995

    Last Sold Summary

    • $185/SF
    • 39 Days On Market

    Current Estimated Value $264,782

    Last Listing Agent Gina Gargeu Century 21 Downtown

    20 Amberstone Ct Unit B, Annapolis, MD 21403
    • /28

      Est $780,141 Not Listed For Sale

      380 Dewey Dr, Annapolis, MD 21401

      • 4 Beds
      • 2.5 Baths
      • 1,920 Sq Ft
      • Built 1962
      380 Dewey Dr, Annapolis, MD 21401

      Last Sold Summary

      • 1% Below List Price
      • $411/SF
      • 46 Days On Market

      Last Sold Price $790,000

      Last Listing Agent Kevin Brown Long & Foster

  • /27

    $372,000 Under Contract

    • 2 Beds
    • 2 Baths
    • 1,440 Sq Ft

    2058 Quaker Way Unit 12, Annapolis, MD 21401

    Nestled within the serene Windgate Condominium community, this exquisite 2-bedroom, 2-bathroom, loft residence offers a harmonious blend of contemporary design and luxurious comfort. Spanning 1,440 square feet, this thoughtfully designed unit is perfect for those seeking an elevated lifestyle. As you step inside, you are greeted by an inviting open floor plan that seamlessly connects the living

    Agent Photo

    Bob Swarm

    Keller Williams Select Realtors of Annapolis

    (410) 896-6929

    2058 Quaker Way Unit 12, Annapolis, MD 21401
  • /50

    $2,550 per month

    • 2 Beds
    • 2 Baths
    • 1,096 Sq Ft
    • Condo for Rent

    2155 Scotts Crossing Ct Unit 101, Annapolis, MD 21401

    Beautifully renovated first floor condo conveniently located within walking distance to the hospital. The kitchen has butcher block counters and stainless steel appliances. Whole home has LVP flooring. Freshly painted home and updated light fixtures. Open floor plan with living room, dining area, and extra area for office/toy room. Large master bedroom with walk in closet and ensuite bath with

    Jamie Angichiodo RE/MAX Leading Edge

    2155 Scotts Crossing Ct Unit 101, Annapolis, MD 21401
  • /68

    $440,000 Sold Aug 29, 2025

    805 Coxswain Way Unit 205, Annapolis, MD 21401

    • 2 Beds
    • 2 Baths
    • 1,364 Sq Ft
    • Built 1991

    Last Sold Summary

    • $323/SF
    • 5 Days On Market

    Last Listing Agent Lori Marino Long & Foster Real Estate, Inc.

    805 Coxswain Way Unit 205, Annapolis, MD 21401
    • /40

      Est $1,630,468 Not Listed For Sale

      1483 Downham Market, Annapolis, MD 21401

      • 5 Beds
      • 3 Baths
      • 3,282 Sq Ft
      • Built 1980
      1483 Downham Market, Annapolis, MD 21401

      Last Sold Summary

      • 2% Above List Price
      • $489/SF
      • 1 Day On Market

      Last Sold Price $1,605,000

      Last Listing Agent Brad Kappel TTR Sotheby's International Realty

  • /86

    $1,350,000 Pending

    • 5 Beds
    • 2.5 Baths
    • 2,727 Sq Ft

    3130 Starboard Dr, Annapolis, MD 21403

    Welcome to your dream home nestled in the sought after water privileged community of Anchorage, where life meets comfort and recreation. This stunning 5 bedroom, 2.5 bath beauty is designed for both relaxation and entertainment, offering a perfect blend of modern updates and classic charm.Step inside to discover a bright and airy open concept living space, enhanced by an updated kitchen

    Agent Photo

    Cheryl Jersey-Lecourt

    Long & Foster Real Estate, Inc.

    (410) 904-6908

    3130 Starboard Dr, Annapolis, MD 21403
  • /53

    $1,411 - $4,195 per month

    Quiet Waters Landing

    1 - 3 Beds

    1293 Thom Ct, Annapolis, MD 21403

    Welcome to Quiet Waters Landing. Our gorgeous apartment community offers one, two, and three bedroom apartments ready for you to move in and call your own. From fantastic in-home features to convenient community amenities, we have it all. Schedule a personalized tour of Quiet Waters Landing and see for yourself.

    1293 Thom Ct, Annapolis, MD 21403
  • /81

    $3,295,000 Sold Apr 30, 2025

    204 Wardour Dr, Annapolis, MD 21401

    • 6 Beds
    • 6.5 Baths
    • 7,550 Sq Ft
    • Built 2012

    Last Sold Summary

    • $436/SF
    • 272 Days On Market

    Current Estimated Value $3,349,126

    Last Listing Agent Georgie Berkinshaw Coldwell Banker Realty

    204 Wardour Dr, Annapolis, MD 21401
    • /35

      Est $387,821 Not Listed For Sale

      1543 Star Pine Dr, Annapolis, MD 21409

      • 3 Beds
      • 2.5 Baths
      • 1,489 Sq Ft
      • Built 1985
      1543 Star Pine Dr, Annapolis, MD 21409

      Last Sold Summary

      • 1% Below List Price
      • $262/SF
      • 2 Days On Market

      Last Sold Price $390,000

      Last Listing Agent Patrick McCarthy RE/MAX

  • /53

    $850,000 Open Sat 11AM - 1PM

    • 4 Beds
    • 3.5 Baths
    • 2,282 Sq Ft

    152 Jefferson St, Annapolis, MD 21403

    RENOVATED EASTPORT GEM With MODERN COASTAL FINISHES! ABOUT THE HOME: 3 levels of luxury living featuring 4 Bedrooms and 3.5 Bathrooms. Open-concept main level with New Hickory hardwood floors and designer lighting throughout. THE GOURMET KITCHEN: Custom white Shaker cabinetry, modern black hardware, Quartz countertops, oversized center island, and premium stainless appliances with gas cooking.

    Agent Photo

    Kara Leddy

    Coldwell Banker Realty

    (443) 201-7578

    152 Jefferson St, Annapolis, MD 21403
  • /23

    $7,800 per month

    • 3 Beds
    • 3 Baths
    • 2,500 Sq Ft
    • House for Rent

    117 Bay Dr, Annapolis, MD 21403

    This lovely home has unsurpassed views of the Bay. Located in popular Bay Ridge, with beaches, marina, pool, recreation, play areas. Open layout with updated first floor primary bedroom, newly renovated primary ensuite with shower and soaking tub overlooking Chesapeake Bay, gleaming wood floors, upper and lower decks to enjoy beautiful sunrises and sunsets. Carport, off-street parking spacious

    Lauren Emrick Innovative Properties, Inc.

    117 Bay Dr, Annapolis, MD 21403
  • /2

    $739,000 Sold Mar 03, 2026

    1101 Little Magothy View, Annapolis, MD 21409

    • 3 Beds
    • 3.5 Baths
    • 2,882 Sq Ft
    • Built 1954

    Last Sold Summary

    • 1% Below List Price
    • $256/SF
    • 5 Days On Market

    Current Estimated Value $728,349

    Last Listing Agent David Orso Berkshire Hathaway HomeServices PenFed Realty

    1101 Little Magothy View, Annapolis, MD 21409
    • /23

      Est $249,095 Not Listed For Sale

      121 Merryman Ct, Annapolis, MD 21401

      • 2 Beds
      • 1.5 Baths
      • 992 Sq Ft
      • Built 1973
      121 Merryman Ct, Annapolis, MD 21401

      Last Sold Summary

      • 2% Above List Price
      • $247/SF
      • 1 Day On Market

      Last Sold Price $245,000

      Last Listing Agent Amy Clune Hartman Realty, LLC.

  • /17

    $349,990 Pending

    • 1,122 Sq Ft

    2052 Quaker Way Unit 7, Annapolis, MD 21401

    This charming condo in the heart of Annapolis offers the perfect blend of comfort and convenience. With its modern finishes and spacious layout, you’ll find a cozy retreat that’s ideal for both relaxing and entertaining.Key Features: Bright and airy living space with large windows that flood the home with natural light.Well-appointed kitchen with updated appliances and ample storage,

    Agent Photo

    Nicholas Badalian

    Fathom Realty MD, LLC

    (410) 364-4941

    2052 Quaker Way Unit 7, Annapolis, MD 21401
  • /50

    $2,095 - $6,001 per month

    Stone Point Apartments

    1 - 3 Beds

    116 Stone Point Dr, Annapolis, MD 21401

    Resort living, Annapolis style. Discover the essentials of living well at Stone Point Apartments. Here, you'll enjoy an unparalleled mix of luxury, convenience and recreation, including a spectacular 10,000 sq. ft. clubhouse with swimming and hydrotherapy pools. With one-, two- and three-bedroom floor plans (some with lofts and dens) to choose from, you'll think you've arrived at a five-star

    116 Stone Point Dr, Annapolis, MD 21401
  • /50

    $650,000 Sold Mar 06, 2026

    100 Severn Ave Unit 206, Annapolis, MD 21403

    • 2 Beds
    • 2 Baths
    • 1,104 Sq Ft
    • Built 1976

    Last Sold Summary

    • 6% Below List Price
    • $589/SF
    • 17 Days On Market

    Current Estimated Value $690,457

    Last Listing Agent Gwin Hunt TTR Sotheby's International Realty

    100 Severn Ave Unit 206, Annapolis, MD 21403
    • /48

      Est $549,282 Not Listed For Sale

      229 Wintergull Ln, Annapolis, MD 21409

      • 4 Beds
      • 2.5 Baths
      • 2,024 Sq Ft
      • Built 2001
      229 Wintergull Ln, Annapolis, MD 21409

      Last Sold Summary

      • $272/SF
      • 2 Days On Market

      Last Sold Price $550,000

      Last Listing Agent Barbara McCaffrey Redfin Corp

  • /41

    $1,999,995 Under Contract

    • 6 Beds
    • 3.5 Baths
    • 5,068 Sq Ft

    107 W Bay View Dr, Annapolis, MD 21403

    Situated on the South River with sweeping water views all the way to the Chesapeake Bay, this Nantucket-inspired waterfront home presents a rare opportunity to create something truly special in one of Annapolis’ most coveted waterfront settings. Set on approximately 0.43 acres with more than 5,000 square feet of living space, the home offers 6 bedrooms and 3.5 baths across two levels. The size of

    Agent Photo

    Reid Buckley

    Long & Foster Real Estate, Inc.

    (443) 291-5158

    107 W Bay View Dr, Annapolis, MD 21403
  • /12

    $2,100 per month

    • 1 Bed
    • 1 Bath
    • 600 Sq Ft
    • Condo for Rent

    126 Prince George St Unit 4, Annapolis, MD 21401

    The heart of Annapolis 1 street from the harbor. This 2nd floor 1 bedroom / 1 bath aprox 600SQ condo has been renovated with new paint, carpet and new kitchen. Split hvac system, so you will control your own ac/heat. Washer/Dryer in the unit. Secure building with locked entry. 1 flight of stairs no one sharing walls with. Water included and wifi for $40 a month

    Nathan Johnson Keller Williams Capital Properties

    126 Prince George St Unit 4, Annapolis, MD 21401
  • /10

    $5,950,000 Sold Apr 15, 2026

    287 State St Unit 2, Annapolis, MD 21403

    • 3 Beds
    • 3 Baths
    • 2,949 Sq Ft
    • Built 2022

    Last Sold Summary

    • $2,018/SF
    • 0 Days On Market

    Last Listing Agent Ryan Turner Coldwell Banker Realty

    287 State St Unit 2, Annapolis, MD 21403
    • /71

      Est $1,006,285 Not Listed For Sale

      7 Hill St, Annapolis, MD 21401

      • 4 Beds
      • 2.5 Baths
      • 2,538 Sq Ft
      • Built 1920
      7 Hill St, Annapolis, MD 21401

      Last Sold Summary

      • 6% Above List Price
      • $374/SF
      • 107 Days On Market

      Last Sold Price $950,000

      Last Listing Agent Bob Chew Samson Properties

  • /61

    $1,500,000

    • 4 Beds
    • 5 Baths
    • 3,393 Sq Ft

    190 Duke of Gloucester St, Annapolis, MD 21401

    Historic charm and everyday comfort come together beautifully in this spacious Victorian in the heart of downtown Annapolis. From the wide front porch—perfect for slow morning coffee or unwinding at the end of the day—to the sun-filled interior, this home offers the rare combination of character, scale, and convenience. With four finished levels, 4 bedrooms, 3 full baths, 2 half baths, and a

    Agent Photo

    Shane Hall

    Compass

    (410) 397-7573

    190 Duke of Gloucester St, Annapolis, MD 21401
  • /19

    $2,473 - $12,886 per month

    Mariner Bay at Annapolis Town Center

    1 - 3 Beds

    1910 Towne Centre Blvd, Annapolis, MD 21401

    For those who are going places in life, there's Mariner Bay at Annapolis Town Center. Welcome to the only luxury high-rise apartment community in Maryland's capital city surrounded by a neighborhood of upscale shopping and dining. From the latest boutique fashions to the freshest organic produce, the hottest restaurants to the most relaxing spa treatments-every convenience imaginable is just

    1910 Towne Centre Blvd, Annapolis, MD 21401
  • /15

    $602,602 Sold Mar 31, 2026

    78 Old Mill Bottom Rd N, Annapolis, MD 21409

    • 2 Beds
    • 2 Baths
    • 1,621 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • $372/SF
    • 364 Days On Market

    The Christopher Companies Element at Mill Creek

    78 Old Mill Bottom Rd N, Annapolis, MD 21409
    • /54

      Est $1,825,944 Not Listed For Sale

      1270 Swan Dr, Annapolis, MD 21409

      • 5 Beds
      • 4.5 Baths
      • 2,848 Sq Ft
      • Built 1971
      1270 Swan Dr, Annapolis, MD 21409

      Last Sold Summary

      • 6% Below List Price
      • $685/SF
      • 137 Days On Market

      Last Sold Price $1,950,000

      Last Listing Agent Steve Podwojski ABR

  • /37

    $315,000

    • 1 Bed
    • 1 Bath
    • 756 Sq Ft

    796 Fairview Ave Unit 796 F, Annapolis, MD 21403

    Welcome to effortless waterfront living in the sought-after Severn House community! This charming 1-bedroom, 1-bath condo offers the perfect blend of tranquility and Annapolis lifestyle—whether you're paddleboarding out for your morning coffee, hopping on the water taxi for an evening in town, or enjoying sunset cruises from your own rented boat slip. Spend your days lounging by the waterfront

    Agent Photo

    Jennifer Marsh

    Cummings & Co. Realtors

    (443) 364-2372

    796 Fairview Ave Unit 796 F, Annapolis, MD 21403
  • /11

    $1,850 per month

    • 1 Bath
    • 850 Sq Ft
    • Condo for Rent

    1072 River Bay Rd Unit BASEMENT, Annapolis, MD 21409

    ***Waterfront*** Cape St. Claire - Basement Flat Freshly painted 1 bedroom Basement FLAT – 1 large room with kitchen, bathroom and closet on waterfront property at the end of River Bay Road. Unit faces STUNNING panoramic views of the Magothy River and Chesapeake Bay. Flat has separate dual heating and cooling wall unit. Property has 4 total units, private dock and common area basement with coin

    Georgia Lightfoot Innovative Properties, Inc.

    1072 River Bay Rd Unit BASEMENT, Annapolis, MD 21409
  • /41

    $1,425,000 Sold Apr 29, 2025

    144 Charles St, Annapolis, MD 21401

    • 4 Beds
    • 3.5 Baths
    • 2,089 Sq Ft
    • Built 1900

    Last Sold Summary

    • $682/SF
    • 5 Days On Market

    Current Estimated Value $1,370,608

    Last Listing Agent Kate Hopkins Coldwell Banker Realty

    144 Charles St, Annapolis, MD 21401
    • /40

      Est $3,405,825 Not Listed For Sale

      1291 Hollywood Ave, Annapolis, MD 21403

      • 6 Beds
      • 4.5 Baths
      • 6,788 Sq Ft
      • Built 2000
      1291 Hollywood Ave, Annapolis, MD 21403

      Last Sold Summary

      • 3% Below List Price
      • $516/SF
      • 0 Days On Market

      Last Sold Price $3,500,000

      Last Listing Agent Brad Kappel TTR Sotheby's International Realty

  • /46

    $3,145,000

    • 3 Beds
    • 2.5 Baths
    • 2,570 Sq Ft

    3307 Harness Creek Rd, Annapolis, MD 21403

    Welcome to 3307 Harness Creek Road: a Nantucket style, coastal home set on a private peninsula with spectacular water views, a serene backyard oasis and two deep-water piers on protected Harness Creek. This waterside gem, with 190 ft of waterfrontage, is situated directly across from Quiet Waters Park and offers quick access to the South River and the Chesapeake Bay.Inside, you’re greeted by

    Agent Photo

    Reid Buckley

    Long & Foster Real Estate, Inc.

    (410) 762-4260

    3307 Harness Creek Rd, Annapolis, MD 21403
  • /50

    $1,628 - $2,638 total monthly price

    Bayshore Landing

    1 - 2 Beds

    988 Spa Rd, Annapolis, MD 21403

    Bayshore Landing is a unique picturesque community with all the conveniences and amenities you would find at a beautiful resort. Here you can enjoy the tranquil pool and sundeck. Find yourself fully rejuvenated after a workout in our fully updated equipped fitness center. Enjoy a cup of coffee, tea, or cocoa in the cozy clubhouse. Enjoy a walk through the community on the paved walking paths. You

    988 Spa Rd, Annapolis, MD 21403
  • /40

    $1,098,000 Sold Jan 05, 2026

    168 Green St, Annapolis, MD 21401

    • 3 Beds
    • 2.5 Baths
    • 1,922 Sq Ft
    • Built 1885

    Last Sold Summary

    • $571/SF
    • 32 Days On Market

    Current Estimated Value $1,055,146

    Last Listing Agent Luke Rozansky Compass

    168 Green St, Annapolis, MD 21401
    • /54

      Est $497,672 Not Listed For Sale

      1560 Ritchie Ln, Annapolis, MD 21401

      • 2 Beds
      • 3.5 Baths
      • 2,335 Sq Ft
      • Built 1986
      1560 Ritchie Ln, Annapolis, MD 21401

      Last Sold Summary

      • 7% Above List Price
      • $199/SF
      • 2 Days On Market

      Last Sold Price $465,000

      Last Listing Agent Melissa Chick Engel & Völkers Annapolis

Showing Results 41 - 80, Page 2 of 18

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