128

Homes for Sale in 21401

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  • 202 Wardour Dr, Annapolis, MD 21401
    202 Wardour Dr, Annapolis, MD 21401
    202 Wardour Dr, Annapolis, MD 21401
    /59

    $1,599,000

    $1M PRICE DROP
    • 5 Beds
    • 2 Baths
    • 2,100 Sq Ft

    202 Wardour Dr, Annapolis, MD 21401

    Welcome to 202 Wardour Drive! This classic 1940 Dutch Colonial offers timeless character, generous living space, and an unbeatable Annapolis location. Situated on a quarter acre lot with large front yard, the south facing location ensures sunny days ahead! Located in the elegant Wardour community which reflects the naturalistic style of its designer, Frederick Law Olmstead, Jr, with its mature

    David Orso Berkshire Hathaway HomeServices PenFed Realty

    202 Wardour Dr, Annapolis, MD 21401
  • 146 Duke of Gloucester St, Annapolis, MD 21401
    146 Duke of Gloucester St, Annapolis, MD 21401
    146 Duke of Gloucester St, Annapolis, MD 21401
    /58

    $1,950,000

    $50K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,042 Sq Ft

    146 Duke of Gloucester St, Annapolis, MD 21401

    Price improvement!!! Welcome to 146 Duke of Gloucester Street! As you approach the home, a welcoming front porch will greet you, offering a place to sit and take in all that Annapolis has to offer. Nestled in the heart of historic Annapolis, this beautifully appointed 4-bedroom, 3.5-bath residence seamlessly blends timeless charm with modern sophistication. Rich in character and thoughtfully

    Rob Carter Douglas Realty, LLC

    146 Duke of Gloucester St, Annapolis, MD 21401
  • 4 Shiley St, Annapolis, MD 21401
    4 Shiley St, Annapolis, MD 21401
    4 Shiley St, Annapolis, MD 21401
    /13

    $3,090,000

    New Construction $195K PRICE DROP
    • 5 Beds
    • 5.5 Baths
    • 5,312 Sq Ft

    4 Shiley St, Annapolis, MD 21401

    This exceptional TO-BE-BUILT opportunity awaits in the coveted West Annapolis community —a rare 0.61-acre offering with endless potential. The custom new build was designed to seamlessly incorporate onto the expansive lot, providing your dream residence in one of the area’s most sought-after neighborhoods. The approved civil engineering plans by Drum, Loyka & Associates, LLC and architectural

    Brad Kappel TTR Sotheby's International Realty

    4 Shiley St, Annapolis, MD 21401
  • 603 Burtons Cove Way Unit 9, Annapolis, MD 21401
    603 Burtons Cove Way Unit 9, Annapolis, MD 21401
    603 Burtons Cove Way Unit 9, Annapolis, MD 21401
    /33

    $327,900

    $12K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,114 Sq Ft

    603 Burtons Cove Way Unit 9, Annapolis, MD 21401

    Welcome home to this bright, beautifully updated 2-bedroom, 2-bathroom condo nestled in the highly sought-after Windgate community of Annapolis! Perfectly positioned just minutes from historic downtown, the U.S. Naval Academy, and major commuter routes (Route 50/I-97), this move-in-ready home offers the ultimate blend of low HOA fee ($320/month), convenience and low-maintenance

    Robert Shaw Taylor Properties

    603 Burtons Cove Way Unit 9, Annapolis, MD 21401
  • 708 Sydney Terrace, Annapolis, MD 21401
    708 Sydney Terrace, Annapolis, MD 21401
    708 Sydney Terrace, Annapolis, MD 21401
    /47

    $715,000

    $23K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,296 Sq Ft

    708 Sydney Terrace, Annapolis, MD 21401

    ** This stunning 3-bedroom, 3-full-bath detached home in Heritage Harbor is a true GEM!**Main Level laminated wood flooring throughout the living room- dinning room and Kitchen.The Kitchen features Elegant gold-and-white granite countertops. A cozy matching granite table that seats three. Brand new white cabinets adorned with gold knobs and pull handles. Complete with modern stainless

    Rita Cordova Taylor Properties

    708 Sydney Terrace, Annapolis, MD 21401
  • 5 Market Quay, Annapolis, MD 21401
    5 Market Quay, Annapolis, MD 21401
    5 Market Quay, Annapolis, MD 21401
    /78

    $3,250,000

    $500K PRICE DROP
    • 4 Beds
    • 4.5 Baths
    • 3,036 Sq Ft

    5 Market Quay, Annapolis, MD 21401

    Welcome home. Perfectly positioned at the end of Market Street, this rare waterfront residence offers an exceptional blend of privacy, design and an impeccable lock and leave lifestyle. Located within an intimate six residence enclave, this fully reimagined contemporary brick townhome captures sweeping views of Spa Creek from every level, delivering a front row experience to Annapolis’ most

    Kathleen Moore Engel & Völkers Annapolis

    5 Market Quay, Annapolis, MD 21401
  • 349 Sherwood Trail, Annapolis, MD 21401
    349 Sherwood Trail, Annapolis, MD 21401
    349 Sherwood Trail, Annapolis, MD 21401
    /49

    $2,395,000

    $155K PRICE DROP
    • 3 Beds
    • 5 Baths
    • 3,185 Sq Ft

    349 Sherwood Trail, Annapolis, MD 21401

    Perched above the Severn River in the gated waterfront community of Epping Forest, this exceptional property captures sweeping water views and effortless indoor/outdoor living just minutes from downtown Annapolis. Thoughtfully designed with an open floor plan and walls of windows, the home is filled with natural light, high ceilings, custom millwork and seamless sightlines to the Severn river

    Brad Kappel TTR Sotheby's International Realty

    349 Sherwood Trail, Annapolis, MD 21401
  • 87 Shipwright St, Annapolis, MD 21401
    87 Shipwright St, Annapolis, MD 21401
    87 Shipwright St, Annapolis, MD 21401
    /38

    $1,600,000

    $250K PRICE DROP
    • 6 Beds
    • 4.5 Baths
    • 2,744 Sq Ft

    87 Shipwright St, Annapolis, MD 21401

    **Price Improvement! ** Now offered at **$1,600,000**.Take another look at 87 Shipwright Street. In addition to the significant price reduction, several important improvements have recently been completed. The roof has been inspected, and minor repairs have been made. The kitchen floor has been repaired, eliminating the previous sag, and the crawlspace has been professionally remediated,

    Catherine Watson - Bye RE/MAX Executive

    87 Shipwright St, Annapolis, MD 21401
  • 20 Shaw St, Annapolis, MD 21401
    20 Shaw St, Annapolis, MD 21401
    20 Shaw St, Annapolis, MD 21401
    /40

    $999,500

    $151K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,500 Sq Ft

    20 Shaw St, Annapolis, MD 21401

    Imagine walking one block to a delightful waterside park and launching a kayak or hopping on a water taxi? Or walk two blocks to a hot new Annapolis restaurant or a classic rock and roll concert? Nestled in the heart of downtown Annapolis in the highly sought-after neighborhood of Murray Hill, this charming Colonial, originally built in 1925 and extensively remodeled in 2016, offers the perfect

    Kate Hopkins Coldwell Banker Realty

    20 Shaw St, Annapolis, MD 21401
  • 113 Sellew Rd, Annapolis, MD 21401
    113 Sellew Rd, Annapolis, MD 21401
    113 Sellew Rd, Annapolis, MD 21401
    /51

    $1,351,875

    New Construction
    • 3 Beds
    • 5 Baths
    • 3,100 Sq Ft

    113 Sellew Rd, Annapolis, MD 21401

    Private Tours and showroom appointments are now available by appointment! Delivery expected to begin December 2026. This listing is for an end unit home on Lot 14. Sturbridge Homes is offering a generous pre-completion incentive package for early buyers. Submit your deposit now to lock in current pricing! Welcome to Towne Row - A community of 18 Luxury Townhomes in the Annapolis Town Center

    Alison Wisnom Coldwell Banker Realty

    113 Sellew Rd, Annapolis, MD 21401
  • 805 Spa Rd, Annapolis, MD 21401
    805 Spa Rd, Annapolis, MD 21401
    805 Spa Rd, Annapolis, MD 21401
    /47

    $1,148,000

    $147K PRICE DROP
    • 9 Beds
    • 4.5 Baths
    • 2,800 Sq Ft

    805 Spa Rd, Annapolis, MD 21401

    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

    Stephanie Henry Bennett Realty Solutions

    805 Spa Rd, Annapolis, MD 21401
  • 2161 Scotts Crossing Ct Unit 30, Annapolis, MD 21401
    2161 Scotts Crossing Ct Unit 30, Annapolis, MD 21401
    2161 Scotts Crossing Ct Unit 30, Annapolis, MD 21401
    /32

    $364,900

    Coming Soon Sep 10
    • 3 Beds
    • 2 Baths
    • 1,328 Sq Ft

    2161 Scotts Crossing Ct Unit 30, Annapolis, MD 21401

    Step into this beautifully maintained top-floor 3-bedroom, 2-bath condo in the desirable Scott’s CrossingCondominiums, offering over 1,320 square feet and a prime location just minutes from the vibrant charm ofdowntown Annapolis. As you enter, you're welcomed by fresh paint throughout (2026), a foyer with aconvenient coat closet, and elegant column accents that open into a bright and

    Sheena Saydam Keller Williams Capital Properties

    2161 Scotts Crossing Ct Unit 30, Annapolis, MD 21401
  • 75 Shipwright St, Annapolis, MD 21401
    75 Shipwright St, Annapolis, MD 21401
    75 Shipwright St, Annapolis, MD 21401
    /94

    $1,449,000

    $101K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 2,557 Sq Ft

    75 Shipwright St, Annapolis, MD 21401

    75 Shipwright Street is an enchanting Victorian semi-detached home located in the heart of the Historic District of downtown Annapolis. This is a rare opportunity to own a five-bedroom historic home directly across from St. Mary's School (Pre-K-12), allowing students to walk to class while enjoying all that Historic Annapolis has to offer. Built around 1910, this four-level residence offers a

    Norman Lee III Anne Arundel Properties, Inc.

    75 Shipwright St, Annapolis, MD 21401
  • 709 Great Bay Ave, Annapolis, MD 21401
    709 Great Bay Ave, Annapolis, MD 21401
    709 Great Bay Ave, Annapolis, MD 21401
    /10

    $322,400

    • 3 Beds
    • 2 Baths
    • 1,381 Sq Ft

    709 Great Bay Ave, Annapolis, MD 21401

    Built in 1996 and located in the Annapolis Walk neighborhood, this attached townhome offersapproximately 1381 finished square feet, three bedrooms, two full baths and rear patio area. Thishome sits on an approximate 1300 sqft lot.

    Dana Rowell RealHome Services and Solutions, Inc.

    709 Great Bay Ave, Annapolis, MD 21401
  • 138 Cranes Crook Ln, Annapolis, MD 21401
    138 Cranes Crook Ln, Annapolis, MD 21401
    138 Cranes Crook Ln, Annapolis, MD 21401
    /57

    $619,000

    Open Sat 1PM - 3PM
    • 4 Beds
    • 3.5 Baths
    • 2,550 Sq Ft

    138 Cranes Crook Ln, Annapolis, MD 21401

    "Like Living in a Tree House!" Nestled in the serene community of Riva Trace, this exquisite end-unit townhouse offers supreme privacy with its enchanting gardens and lush landscaped, irrigated surround. Once inside, you will enjoy 2,550 sq. ft. of thoughtfully designed living space on 3 levels, including four spacious bedrooms(three up & 1 down) and 3.5 bathrooms. The home features a classic

    Yael Beckman Coldwell Banker Realty

    138 Cranes Crook Ln, Annapolis, MD 21401
  • 1430 Catlyn Place, Annapolis, MD 21401
    1430 Catlyn Place, Annapolis, MD 21401
    1430 Catlyn Place, Annapolis, MD 21401
    /29

    $644,900

    • 4 Beds
    • 2.5 Baths
    • 2,156 Sq Ft

    1430 Catlyn Place, Annapolis, MD 21401

    You Will Fall In Love with this Huge, 4 Bedroom 2.5 Bath home in the Wonderful Sought after Heritage Community! 2 Family Rooms, Dining Room, Custom Tile bath, Just re-sanded Stunning Hardwood Floors throughout the main level, Master Bedroom with an ensuite bath and walk-in custom shower, New Beautiful Flooring in the lower-level Family Room, Great Rear Deck overlooking the large, fenced backyard

    Donna Reichert Keller Williams Flagship

    1430 Catlyn Place, Annapolis, MD 21401
  • 607 Melvin Ave, Annapolis, MD 21401
    607 Melvin Ave, Annapolis, MD 21401
    607 Melvin Ave, Annapolis, MD 21401
    /58

    $899,000

    • 2 Beds
    • 2 Baths
    • 1,102 Sq Ft

    607 Melvin Ave, Annapolis, MD 21401

    Open House Saturday July 11th, 11AM - 1PM! Come Join us to see this adorable bungalow in a prime West Annapolis Location! Easy one-level living with a great fenced-in yard and a large, detached garage. Super fun, walkable location—catch Navy Midshipmen football games or stroll to Chessie’s Wharf, Positano’s, Bean Rush Cafe, Always Ice Cream Company & more! Just a short distance to Downtown

    Joanna Dalton Coldwell Banker Realty

    607 Melvin Ave, Annapolis, MD 21401
  • 11 S Acton Place, Annapolis, MD 21401
    11 S Acton Place, Annapolis, MD 21401
    11 S Acton Place, Annapolis, MD 21401
    /75

    $7,250,000

    $749K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,658 Sq Ft

    11 S Acton Place, Annapolis, MD 21401

    Perfectly positioned along the waterfront in the prestigious Murray Hill neighborhood of Annapolis, this extraordinary estate represents a rare opportunity to own a fully reimagined luxury residence where privacy, walkability, boating lifestyle, and architectural sophistication converge in one of the East Coast’s most coveted waterfront settings. RenownedBohan Contracting has been extensively

    Shawn Martin Real Broker, LLC

    11 S Acton Place, Annapolis, MD 21401
  • 1915 Towne Centre Blvd Unit 915, Annapolis, MD 21401
    1915 Towne Centre Blvd Unit 915, Annapolis, MD 21401
    1915 Towne Centre Blvd Unit 915, Annapolis, MD 21401
    /54

    $719,900

    $30K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,616 Sq Ft

    1915 Towne Centre Blvd Unit 915, Annapolis, MD 21401

    Now priced at $719,900—reduced from $749,900—and including a $5,000 seller credit toward closing costs, this stunning Bridgeport model condo offers unmatched value in the Grandview community.Experience breathtaking views from this stunning Bridgeport model condo in the highly sought-after Grandview community! This beautifully designed home features an open-concept floor plan with gleaming

    Agnes Kongas-Sawera RE/MAX Leading Edge

    1915 Towne Centre Blvd Unit 915, Annapolis, MD 21401
  • 4 Shiley St, Annapolis, MD 21401
    4 Shiley St, Annapolis, MD 21401
    4 Shiley St, Annapolis, MD 21401
    /14

    $1,495,000

    $380K PRICE DROP
    • Land
    • 26,571 Sq Ft
    • $2,450,820 per Acre

    4 Shiley St, Annapolis, MD 21401

    An exceptional opportunity awaits in coveted West Annapolis—a rare 0.61-acre offering with endless potential. Whether you envision a thoughtful renovation or a custom new build, this expansive lot provides the perfect canvas to create your dream residence in one of the area’s most sought-after neighborhoods. Approved civil engineering plans by Drum, Loyka & Associates, LLC and architectural

    Brad Kappel TTR Sotheby's International Realty

    4 Shiley St, Annapolis, MD 21401
  • 31 College Ave, Annapolis, MD 21401
    31 College Ave, Annapolis, MD 21401
    31 College Ave, Annapolis, MD 21401
    /35

    $580,000

    $19K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 632 Sq Ft

    31 College Ave, Annapolis, MD 21401

    NEW PRICE — REDUCED $580,000! An incredible opportunity to own one of the best values in Historic Downtown Annapolis. Property can convey FULLY FURNISHED, offering a truly turnkey opportunity! Location, location, location! Enjoy the best of Historic Downtown Annapolis from this charming one-level condo at 31 College Avenue, ideally situated just steps from the U.S. Naval Academy and St. John’s

    Joanna Dalton Coldwell Banker Realty

    31 College Ave, Annapolis, MD 21401
  • 2052 Quaker Way Unit 10, Annapolis, MD 21401
    2052 Quaker Way Unit 10, Annapolis, MD 21401
    2052 Quaker Way Unit 10, Annapolis, MD 21401
    /23

    $345,000

    • 2 Beds
    • 2 Baths
    • 1,113 Sq Ft

    2052 Quaker Way Unit 10, Annapolis, MD 21401

    Welcome to this beautifully updated two-bedroom, two-bath condo, offering a fresh, modern feel and an incredibly convenient Annapolis location. Recent improvements include light tan luxury vinyl plank flooring throughout the entire unit, new hardware, and a completely renovated kitchen designed with both style and functionality in mind.The brand-new kitchen features custom 42-inch

    Justin Disborough Samson Properties

    2052 Quaker Way Unit 10, Annapolis, MD 21401
  • 371 Carriage Park Way, Annapolis, MD 21401
    371 Carriage Park Way, Annapolis, MD 21401
    371 Carriage Park Way, Annapolis, MD 21401
    /17

    $1,157,456

    $125K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 6,724 Sq Ft

    371 Carriage Park Way, Annapolis, MD 21401

    Foreclosure opportunity in sought-after Annapolis! Spacious 4BR/3.5BA Colonial with over 4,500 sq ft of living space. Features include multiple living areas, large kitchen footprint, finished lower level, and generous bedroom sizes. Private backyard with in-ground pool ready to be restored. Excellent potential for renovation or investment. Convenient to shopping, dining, major routes, and

    Christopher Guldi Keller Williams Flagship

    371 Carriage Park Way, Annapolis, MD 21401
  • 310 Epping Way, Annapolis, MD 21401
    310 Epping Way, Annapolis, MD 21401
    310 Epping Way, Annapolis, MD 21401
    /42

    $1,050,000

    $50K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,036 Sq Ft

    310 Epping Way, Annapolis, MD 21401

    Tucked within the gated waterfront community of Epping Forest, this charming Craftsman bungalow captures the ease and appeal of Annapolis waterfront living with the rare advantage of true one-level living. Perfectly positioned on one of the community’s largest and flattest lots, the property offers a difficult-to-find combination of privacy, outdoor space, and low-maintenance comfort just moments

    Brad Kappel TTR Sotheby's International Realty

    310 Epping Way, Annapolis, MD 21401
  • 1614 Annesley Ct, Annapolis, MD 21401
    1614 Annesley Ct, Annapolis, MD 21401
    1614 Annesley Ct, Annapolis, MD 21401
    /46

    $2,250,000

    Open Thu 4PM - 7PM
    • 5 Beds
    • 7 Baths
    • 8,278 Sq Ft

    1614 Annesley Ct, Annapolis, MD 21401

    Welcome to this exceptional custom-built estate set on 3.1 acres in Wyatts Hill community. Offering three finished levels of thoughtfully designed living space, this five-bedroom, seven-bathroom home combines timeless architecture, modern updates, and resort-inspired outdoor living. A grand two-story foyer welcomes you with a sweeping curved staircase and soaring ceilings. The main level is

    Brad Kappel TTR Sotheby's International Realty

    1614 Annesley Ct, Annapolis, MD 21401
  • 8 Constitution Square, Annapolis, MD 21401
    8 Constitution Square, Annapolis, MD 21401
    8 Constitution Square, Annapolis, MD 21401
    /26

    $995,000

    $33K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,751 Sq Ft

    8 Constitution Square, Annapolis, MD 21401

    Live the ultimate Downtown Annapolis lifestyle at 8 Constitution Square. Tucked away on a quiet, neighborly cul-de-sac in Murray Hill, this home offers a seamless blend of tranquility and effortless downtown walkability. Skip the parking headaches of historic downtown. Here, you'll enjoy your own private driveway on a low traffic street, giving you a true neighborhood feel right in the heart of

    Whitney Jerdal Compass

    8 Constitution Square, Annapolis, MD 21401
  • 8 Spa View Cir, Annapolis, MD 21401
    8 Spa View Cir, Annapolis, MD 21401
    8 Spa View Cir, Annapolis, MD 21401
    /56

    $11,500,000

    $1M PRICE DROP
    • 5 Beds
    • 5.5 Baths
    • 6,061 Sq Ft

    8 Spa View Cir, Annapolis, MD 21401

    Experience one of the few Annapolis waterfront estates where you can leave your private dock and arrive at City Dock in minutes. Ideally situated on Spa Creek, this exceptional property captures the essence of Annapolis waterfront living with panoramic water views, unobstructed views of the Annapolis skyline, and endless opportunities for boating, kayaking, paddleboarding, and entertaining.

    Georgie Berkinshaw Coldwell Banker Realty

    8 Spa View Cir, Annapolis, MD 21401
  • 622 Wayward Dr, Annapolis, MD 21401
    622 Wayward Dr, Annapolis, MD 21401
    622 Wayward Dr, Annapolis, MD 21401
    /44

    $600,000

    $25K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,240 Sq Ft

    622 Wayward Dr, Annapolis, MD 21401

    Welcome home to this beautifully renovated split-level in a sought-after community! Featuring a bright, open floor plan with quality finishes throughout, this move-in ready home offers wood floors, an updated kitchen, and fully renovated baths. The three-bedroom layout provides comfortable living spaces designed for today's lifestyle.Nestled on a private, wooded 0.40-acre lot backing to

    Kimberly O'Connor Coldwell Banker Realty

    622 Wayward Dr, Annapolis, MD 21401
  • 3 Rosewood St, Annapolis, MD 21401
    3 Rosewood St, Annapolis, MD 21401
    3 Rosewood St, Annapolis, MD 21401
    /25

    $1,350,000

    • 6 Beds
    • 5.5 Baths
    • 2,922 Sq Ft

    3 Rosewood St, Annapolis, MD 21401

    New construction from acclaimed local builder, Sturbridge Homes! This spectacular home offers over 3,900 square feet of finished space in the heart of Annapolis's Homewood neighborhood, close to all of the entertainment and enjoyment available in our historic town. Located near the new Annapolis Public Library, Maryland Hall, Annapolis Town Center, and the Naval Academy Stadium, this home is

    Alison Wisnom Coldwell Banker Realty

    3 Rosewood St, Annapolis, MD 21401
  • 500 Sara Dr, Annapolis, MD 21401
    500 Sara Dr, Annapolis, MD 21401
    500 Sara Dr, Annapolis, MD 21401
    /35

    $1,750,000

    $500K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 4,771 Sq Ft

    500 Sara Dr, Annapolis, MD 21401

    Set back off the road on a quiet cul-de-sac in the coveted Saefern community, this contemporary home offers peaceful water views, a private wooded setting, and endless potential to make it your own. Whether you're looking to move right in and enjoy the home as it is or reimagine the space into your dream retreat, this property presents an incredible opportunity in one of Annapolis' most

    Brad Kappel TTR Sotheby's International Realty

    500 Sara Dr, Annapolis, MD 21401
  • 112 Speicher Dr, Annapolis, MD 21401
    112 Speicher Dr, Annapolis, MD 21401
    112 Speicher Dr, Annapolis, MD 21401
    /38

    $949,000

    $51K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 2,912 Sq Ft

    112 Speicher Dr, Annapolis, MD 21401

    Nestled in the serene enclave of Corbin Park, this exquisite Colonial-style residence offers a harmonious blend of elegance and comfort, perfect for those seeking a luxurious lifestyle. With 2,912 square feet of thoughtfully designed living space, the main home features 3 spacious bedrooms and 2 and a half bathrooms, ensuring ample room for relaxation and entertainment. The separate attached

    Christine Leonard Redfin Corp

    112 Speicher Dr, Annapolis, MD 21401
  • 924 Shipmaster Ct, Annapolis, MD 21401
    924 Shipmaster Ct, Annapolis, MD 21401
    924 Shipmaster Ct, Annapolis, MD 21401
    /70

    $540,000

    • 2 Beds
    • 2 Baths
    • 1,634 Sq Ft

    924 Shipmaster Ct, Annapolis, MD 21401

    Buyers' plans changed; your lucky day is now available.Enjoy easy, one-level living in this beautifully maintained end-unit home in Heritage Harbour, Annapolis’ premier 55+ community. Tucked along a peaceful, tree-lined street and conveniently located near the community center, this inviting 2-bedroom, 2-bath home with a den and spectacular four-season sunroom offers comfort, privacy, and an

    Michele Cordle Long & Foster Real Estate, Inc.

    924 Shipmaster Ct, Annapolis, MD 21401
  • 100 Market St, Annapolis, MD 21401
    100 Market St, Annapolis, MD 21401
    100 Market St, Annapolis, MD 21401
    /69

    $1,625,000

    • 2 Beds
    • 2.5 Baths
    • 2,245 Sq Ft

    100 Market St, Annapolis, MD 21401

    Rarely does a home of this historical significance become available in the heart of Historic Annapolis. Believed to date to the late 17th century, the extraordinary residence is among the city's oldest surviving homes, seamlessly blending centuries of architectural heritage with sophisticated modern living. Perched at the water end of Market St overlooking Spa Creek, this home is instantly

    Moe Farley Coldwell Banker Realty

    100 Market St, Annapolis, MD 21401
  • 16 Woodlawn Ave, Annapolis, MD 21401
    16 Woodlawn Ave, Annapolis, MD 21401
    16 Woodlawn Ave, 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
  • 729 Crisfield Way, Annapolis, MD 21401
    729 Crisfield Way, Annapolis, MD 21401
    729 Crisfield Way, Annapolis, MD 21401
    /58

    $865,000

    Open Sat 12PM - 2PM Coming Soon Sep 10
    • 4 Beds
    • 4.5 Baths
    • 4,691 Sq Ft

    729 Crisfield Way, Annapolis, MD 21401

    Stunning and spacious home located in the sought-after, amenity-rich community of Kingsport! Offering approximately 4,600 square feet of beautifully finished living space, this home delivers an exceptional combination of size, style, updates, and value. The sellers have thoughtfully refreshed the home throughout, highlighted by a completely updated kitchen featuring new appliances, quartz

    Scott Schuetter Berkshire Hathaway HomeServices PenFed Realty

    729 Crisfield Way, Annapolis, MD 21401
  • 83 Market St, Annapolis, MD 21401
    83 Market St, Annapolis, MD 21401
    83 Market St, 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
  • 34 Pinkney St, Annapolis, MD 21401
    34 Pinkney St, Annapolis, MD 21401
    34 Pinkney 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
  • 126 Spring Place Way, Annapolis, MD 21401
    126 Spring Place Way, Annapolis, MD 21401
    126 Spring Place Way, Annapolis, MD 21401
    /46

    $554,900

    $14K PRICE DROP
    • 3 Beds
    • 3.5 Baths
    • 2,323 Sq Ft

    126 Spring Place Way, Annapolis, MD 21401

    Nestled in the charming community of Riva Trace, this delightful townhouse offers a perfect blend of comfort and convenience. Built in 1990, this traditional-style home features a classic brick front and wood siding, exuding warmth and character from the moment you arrive. With 2,323 square feet of thoughtfully designed living space, this residence is ideal for those seeking a cozy retreat in a

    Christine Zeng ExecuHome Realty

    126 Spring Place Way, Annapolis, MD 21401
  • 402 S Cherry Grove Ave, Annapolis, MD 21401
    402 S Cherry Grove Ave, Annapolis, MD 21401
    402 S Cherry Grove Ave, Annapolis, MD 21401
    /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
  • 1915 Towne Centre Blvd Unit 513, Annapolis, MD 21401
    1915 Towne Centre Blvd Unit 513, Annapolis, MD 21401
    1915 Towne Centre Blvd Unit 513, Annapolis, MD 21401
    /62

    $549,000

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

    1915 Towne Centre Blvd Unit 513, 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 (no carpet), soaring 10-foot ceilings, elegant granite

    David Yee Coldwell Banker Realty

    1915 Towne Centre Blvd Unit 513, Annapolis, MD 21401

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