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Annapolis, MD Homes for Sale with a Community Boat Dock

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  • 2978 Valley View Rd, Annapolis, MD 21401
    2978 Valley View Rd, Annapolis, MD 21401
    2978 Valley View Rd, Annapolis, MD 21401
    /61

    $975,000

    • 4 Beds
    • 3.5 Baths
    • 2,553 Sq Ft

    2978 Valley View Rd, Annapolis, MD 21401

    Nestled in the highly sought-after, water-privileged community of Cape St. John, this exceptional 4-bedroom, 3.5-bath residence, beautifully renovated in 2017, offers an ideal blend of luxury, comfort, and the coveted Chesapeake Bay lifestyle. Residents enjoy exclusive access to the South River, including a private beach, boat ramp, docks, pavilion, and playground. Whether spending the day on the

    Agent Photo

    Cheryl Jersey-Lecourt

    Long & Foster Real Estate, Inc.

    2978 Valley View Rd, Annapolis, MD 21401
  • 108 Maple Dr, Annapolis, MD 21403
    108 Maple Dr, Annapolis, MD 21403
    108 Maple Dr, Annapolis, MD 21403
    /62

    $674,900

    $25K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,140 Sq Ft

    108 Maple Dr, Annapolis, MD 21403

    New price! Welcome to 108 Maple Drive, a beautifully updated rancher in the sought-after waterfront community of Hillsmere Shores. Renovated throughout in 2016, this move-in ready home offers 3 bedrooms, 3 full baths, and the convenience of single-level living in one of Annapolis' most beloved neighborhoods. Inside, you'll find updated finishes, an inviting floor plan, and comfortable living

    Agent Photo

    Matthew Wyble

    Next Step Realty

    108 Maple Dr, Annapolis, MD 21403
  • 1098 Magothy Cir, Annapolis, MD 21409
    1098 Magothy Cir, Annapolis, MD 21409
    1098 Magothy Cir, Annapolis, MD 21409
    /52

    $1,300,000

    Coming Soon
    • 5 Beds
    • 3 Baths
    • 3,152 Sq Ft

    1098 Magothy Cir, Annapolis, MD 21409

    Welcome to this impressive 4,300-square-foot waterfront residence located on the scenic Little Magothy River, renowned among the 105 homes here as Annapolis's best-kept secret. This elegant home offers five bedrooms and three full bathrooms, designed to accommodate comfort and luxury. Enjoy expansive water views and effortless access to the Chesapeake Bay, making this an ideal property for

    Agent Photo

    Amy Juras

    Long & Foster Real Estate, Inc.

    1098 Magothy Cir, Annapolis, MD 21409
  • 2002 Dakota Place Unit 2A, Annapolis, MD 21403
    2002 Dakota Place Unit 2A, Annapolis, MD 21403
    2002 Dakota Place Unit 2A, Annapolis, MD 21403
    /28

    $650,000

    • 2 Beds
    • 2.5 Baths
    • 1,915 Sq Ft

    2002 Dakota Place Unit 2A, Annapolis, MD 21403

    Enjoy resort-style waterfront living with harbor and Chesapeake Bay views in the gated community of Chesapeake Harbour. This beautifully updated two-level residence offers the ideal blend of comfort, natural light, and low-maintenance coastal living. Freshly painted throughout with new carpet, the home features a thoughtfully designed floor plan with over 1,900 square feet of living space, an

    Brad Kappel TTR Sotheby's International Realty

    2002 Dakota Place Unit 2A, Annapolis, MD 21403
  • 6 President Point Dr Unit B3, Annapolis, MD 21403
    6 President Point Dr Unit B3, Annapolis, MD 21403
    6 President Point Dr Unit B3, Annapolis, MD 21403
    /38

    $1,025,000

    • 3 Beds
    • 2 Baths
    • 1,467 Sq Ft

    6 President Point Dr Unit B3, Annapolis, MD 21403

    Experience a hassle-free waterfront lifestyle at The Point on Spa Creek, where this stunning condo offers exceptionally easy living with picturesque views overlooking Historic Annapolis and Spa Creek. This spacious 2 bedroom 2 bath condo with flexible loft space features beautifully appointed rooms and is just steps away from the clubhouse, pool, dock, and scenic walking paths. The expansive

    Brad Kappel TTR Sotheby's International Realty

    6 President Point Dr Unit B3, Annapolis, MD 21403
  • 2035 Maidstone Farm Rd, Annapolis, MD 21409
    2035 Maidstone Farm Rd, Annapolis, MD 21409
    2035 Maidstone Farm Rd, Annapolis, MD 21409
    /72

    $8,750,000

    • 5 Beds
    • 6.5 Baths
    • 7,105 Sq Ft

    2035 Maidstone Farm Rd, Annapolis, MD 21409

    Commanding extraordinary panoramic Chesapeake Bay views from its south-facing setting, this exceptional waterfront estate offers 210 feet of shoreline on 3.10 private acres in the exclusive Maidstone Farm community. Designed to embrace its remarkable waterfront setting, the residence captures sweeping, unobstructed views from nearly every principal room, with magnificent sunrises, vibrant

    Georgie Berkinshaw Coldwell Banker Realty

    2035 Maidstone Farm Rd, Annapolis, MD 21409
  • 1000 Lakeview Ln, Annapolis, MD 21409
    1000 Lakeview Ln, Annapolis, MD 21409
    1000 Lakeview Ln, Annapolis, MD 21409
    /44

    $700,000

    • 3 Beds
    • 2 Baths
    • 2,000 Sq Ft

    1000 Lakeview Ln, Annapolis, MD 21409

    Wake up to exceptional views of the Magothy and Lake Claire from this meticulously maintained raised rancher in the highly sought-after waterfront community of Cape St. Claire. Recent renovations have been completed, allowing a new family to move right in and begin enjoying everything this property has to offer. With the community marina just a block away, you'll enjoy the rare combination of

    Matthew Arnold Real Broker, LLC

    1000 Lakeview Ln, Annapolis, MD 21409
  • 726 Hillcrest Dr, Annapolis, MD 21409
    726 Hillcrest Dr, Annapolis, MD 21409
    726 Hillcrest Dr, Annapolis, MD 21409
    /57

    $659,000

    • 3 Beds
    • 2.5 Baths
    • 2,681 Sq Ft

    726 Hillcrest Dr, Annapolis, MD 21409

    Welcome to this beautifully updated and meticulously maintained home in the highly sought-after water-privileged community of Cape St. Claire! Offering the perfect blend of comfort, style, and energy efficiency, this move-in-ready gem features an updated kitchen, an expansive primary suite with an enlarged spa-like bath, a cozy family room with a fireplace, a finished walk-out lower level, a

    Antonia Barry Coldwell Banker Realty

    726 Hillcrest Dr, Annapolis, MD 21409
  • 5 Market Quay, Annapolis, MD 21401
    5 Market Quay, Annapolis, MD 21401
    5 Market Quay, Annapolis, MD 21401
    /78

    $3,499,000

    Open Thu 5PM - 7PM $251K 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
  • 3403 Hidden River View Rd, Annapolis, MD 21403
    3403 Hidden River View Rd, Annapolis, MD 21403
    3403 Hidden River View Rd, Annapolis, MD 21403
    /50

    $1,750,000

    • 4 Beds
    • 5 Baths
    • 3,836 Sq Ft

    3403 Hidden River View Rd, Annapolis, MD 21403

    Experience the best of Annapolis living in the sought-after, amenities-rich community of Fishing Creek Farm. Perfectly positioned to capture beautiful water views and surrounded by lush lawns and mature landscaping, this handsome brick-front Colonial offers a rare combination of timeless architecture, flexible living spaces, and an exceptional neighborhood lifestyle. A gracious foyer welcomes you

    Brad Kappel TTR Sotheby's International Realty

    3403 Hidden River View Rd, Annapolis, MD 21403
  • 621 Harbor Dr, Annapolis, MD 21403
    621 Harbor Dr, Annapolis, MD 21403
    621 Harbor Dr, Annapolis, MD 21403
    /85

    $1,500,000

    • 5 Beds
    • 3.5 Baths
    • 3,620 Sq Ft

    621 Harbor Dr, Annapolis, MD 21403

    Sunsets, Water Views & Effortless Coastal Living in HillsmerePerfectly positioned on one of the quietest streets in Hillsmere, this exceptional residence offers breathtaking water views of Lake Hillsmere in the foreground and the South River beyond—without the expense of waterfront taxes.Designed to embrace its spectacular setting, the home is oriented to the west, delivering

    Sandra K. Libby Long & Foster Real Estate, Inc.

    621 Harbor Dr, Annapolis, MD 21403
  • 3728 Ramsgate Dr, Annapolis, MD 21403
    3728 Ramsgate Dr, Annapolis, MD 21403
    3728 Ramsgate Dr, Annapolis, MD 21403
    /68

    $6,995,000

    • 4 Beds
    • 5.5 Baths
    • 5,771 Sq Ft

    3728 Ramsgate Dr, Annapolis, MD 21403

    Set on a spectacular point of land where the South River meets the Chesapeake Bay, this extraordinary waterfront estate captures some of the most breathtaking views in Annapolis. With coveted southern exposure, the property is immersed in sunlight from dawn to dusk, creating an ever-changing backdrop of sparkling water, passing sailboats, and panoramic Chesapeake vistas. Completely reimagined in

    Brad Kappel TTR Sotheby's International Realty

    3728 Ramsgate Dr, Annapolis, MD 21403
  • 1047 Little Magothy View, Annapolis, MD 21409
    1047 Little Magothy View, Annapolis, MD 21409
    1047 Little Magothy View, Annapolis, MD 21409
    /85

    $825,000

    • 3 Beds
    • 2.5 Baths
    • 2,892 Sq Ft

    1047 Little Magothy View, Annapolis, MD 21409

    Welcome home to this one of a kind three bedroom, two and a half bath rancher on a double lot in sought after Cape St Claire. One level living at it's finest, with a huge sunroom with vaulted ceiling on one wing, and the bedrooms on the other wing of this sprawling rancher. This property has been lovingly maintained by the owners, with the addition of the sunroom, powder room, laundry room, and

    Christopher Fuller Long & Foster Real Estate, Inc.

    1047 Little Magothy View, Annapolis, MD 21409
  • 1848 Cherry Rd, Annapolis, MD 21409
    1848 Cherry Rd, Annapolis, MD 21409
    1848 Cherry Rd, Annapolis, MD 21409
    /56

    $875,000

    $20K PRICE DROP
    • 6 Beds
    • 3 Baths
    • 3,150 Sq Ft

    1848 Cherry Rd, Annapolis, MD 21409

    Some addresses just make life better. This one is tucked back in Beechwood on the Burley — a sought-after water-privileged community in St. Margarets, with private access to Burley Creek for kayaking, canoeing, and boating, plus a community pier, dock slips, and picnic area steps from your door. Downtown Annapolis is less than 2 miles away, yet the setting feels genuinely private, sheltered under

    Emily Marsh Engel & Völkers Annapolis

    1848 Cherry Rd, Annapolis, MD 21409
  • 819 Janice Dr, Annapolis, MD 21403
    819 Janice Dr, Annapolis, MD 21403
    819 Janice Dr, Annapolis, MD 21403
    /42

    $1,125,000

    $70K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 4,043 Sq Ft

    819 Janice Dr, Annapolis, MD 21403

    Striking modern craftsman located in Eastport! This beautifully constructed home boasts 3 levels of living space including the finished basement with great room, bonus room and full bath. The community of Green Acres is a private, water privileged neighborhood with a waterfront park just steps from the home. Located on Back Creek the residents enjoy boat slips, canoe/kayak storage and vibrant

    Brad Kappel TTR Sotheby's International Realty

    819 Janice Dr, Annapolis, MD 21403
  • 310 Epping Way, Annapolis, MD 21401
    310 Epping Way, Annapolis, MD 21401
    310 Epping Way, Annapolis, MD 21401
    /42

    $1,100,000

    • 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
  • 700 N Holly Dr, Annapolis, MD 21409
    700 N Holly Dr, Annapolis, MD 21409
    700 N Holly Dr, Annapolis, MD 21409
    /53

    $1,075,000

    Open Sun 2PM - 4PM $24K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,072 Sq Ft

    700 N Holly Dr, Annapolis, MD 21409

    Don’t miss this rarely available 4-bedroom, 2.5-bath Colonial in the highly sought-after, water-privileged community of Amberley. Fresh paint and abundant natural light create a warm and inviting atmosphere throughout. The kitchen is filled with natural light and offers gray-toned cabinetry, recessed lighting, a sunny breakfast area, and peaceful tree-lined views. Perfect for both everyday living

    Sheena Saydam Keller Williams Capital Properties

    700 N Holly Dr, Annapolis, MD 21409
  • 1486 Downham Market, Annapolis, MD 21401
    1486 Downham Market, Annapolis, MD 21401
    1486 Downham Market, Annapolis, MD 21401
    /113

    $3,250,000

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

    1486 Downham Market, Annapolis, MD 21401

    1486 Downham Market is the ultimate Annapolis deep-water estate—designed for those who demand luxury, security, and boating excellence. Perfectly positioned at the mouth of Clements Creek—one of the safest hurricane holes on the Severn River—this home pairs architectural brilliance with one of the region’s most coveted waterfront settings. A commanding 180’ pier with three boat slips, 50-amp

    Wendy Oliver Coldwell Banker Realty

    1486 Downham Market, Annapolis, MD 21401
  • 755 Fairview Ave Unit 755 D, Annapolis, MD 21403
    755 Fairview Ave Unit 755 D, Annapolis, MD 21403
    755 Fairview Ave Unit 755 D, Annapolis, MD 21403
    /39

    $549,995

    • 3 Beds
    • 2 Baths
    • 1,295 Sq Ft

    755 Fairview Ave Unit 755 D, Annapolis, MD 21403

    $ 25,000.00 PRICE REDUCTION --WELCOME HOME!This beautifully Renovated Eastport Marina Condo with Deeded 30’ Slip A 54 & Waterfront Pool.This 3-bed, 2-bath end-unit condo in sought-after Severn House Condominiums blends coastal charm with modern luxury. Nearly every detail has been refreshed or rebuilt—new electrical, premium hardwood flooring throughout, added in-unit laundry, and a fully

    Carey Laycock RE/MAX Leading Edge

    755 Fairview Ave Unit 755 D, Annapolis, MD 21403
  • 3115 Starboard Dr, Annapolis, MD 21403
    3115 Starboard Dr, Annapolis, MD 21403
    /2

    $965,750

    Coming Soon
    • 5 Beds
    • 3 Baths
    • 2,900 Sq Ft

    3115 Starboard Dr, Annapolis, MD 21403

    A spectacular home is about to hit the market in one of Annapolis' most sought-after waterfront communities. Welcome to 3115 Starboard Drive in Anchorage—an expansive, beautifully renovated residence featuring 5 generous bedrooms, 3 full baths, rich hardwood floors, two fireplaces, a spacious two-car garage, and a stunning screened porch designed for effortless year-round enjoyment. Perfectly

    Wendy Oliver Coldwell Banker Realty

    3115 Starboard Dr, Annapolis, MD 21403
  • 844 Harbor View Terrace, Annapolis, MD 21409
    844 Harbor View Terrace, Annapolis, MD 21409
    844 Harbor View Terrace, Annapolis, MD 21409
    /70

    $1,175,000

    $75K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 2,920 Sq Ft

    844 Harbor View Terrace, Annapolis, MD 21409

    Previous Buyers move from California fell through. Home is back on the market and ready for you! Wake up to panoramic views of the Magothy River from this beautifully updated home in the sought-after waterfront community of Cape St. Claire. Expansive windows fill the home with natural light while showcasing breathtaking water views from many of the primary living spaces. The stunning remodeled

    Brooke Austin-McAdam TTR Sotheby's International Realty

    844 Harbor View Terrace, Annapolis, MD 21409
  • 1603 Winchester Rd, Annapolis, MD 21409
    1603 Winchester Rd, Annapolis, MD 21409
    1603 Winchester Rd, Annapolis, MD 21409
    /39

    $2,500,000

    New Construction
    • 6 Beds
    • 6.5 Baths
    • 6,709 Sq Ft

    1603 Winchester Rd, Annapolis, MD 21409

    READY TO BUILD NOW!! Introducing an exceptional opportunity to build your dream home with a local custom home builder on a rare 2.19-acre homesite in the highly sought-after water-privileged community of Winchester on the Severn—a neighborhood where everyday living feels like a vacation. This thoughtfully designed custom home will offer over 6,700 square feet of finished living space, featuring 6

    Scott Schuetter Berkshire Hathaway HomeServices PenFed Realty

    1603 Winchester Rd, Annapolis, MD 21409
  • 1739 Vineyard Trail, Annapolis, MD 21401
    1739 Vineyard Trail, Annapolis, MD 21401
    1739 Vineyard Trail, Annapolis, MD 21401
    /78

    $1,950,000

    • 4 Beds
    • 3 Baths
    • 2,890 Sq Ft

    1739 Vineyard Trail, Annapolis, MD 21401

    Stunning offering in gated Epping Forest! This mid-century modern waterfront sanctuary rises above Saltworks Creek on a quiet protected cove all on a .34 Acre lot—where timeless design meets an ethereal, peaceful connection to the water and outside. Originally built in 1978, the almost 3600 sq. ft residence recently underwent a comprehensive renovation inside and out while honoring Mid-Century

    Christy Bishop Berkshire Hathaway HomeServices PenFed Realty

    1739 Vineyard Trail, Annapolis, MD 21401
  • 410 Walnut Dr, Annapolis, MD 21403
    410 Walnut Dr, Annapolis, MD 21403
    410 Walnut Dr, Annapolis, MD 21403
    /42

    $464,000

    • 3 Beds
    • 1 Bath
    • 1,368 Sq Ft

    410 Walnut Dr, Annapolis, MD 21403

    A CHERISHED FAMILY CLASSIC IN WATERFRONT HILLSMERE ESTATES! 410 Walnut Road presents a rare opportunity in one of Annapolis’s most coveted water-privileged communities. Lovingly maintained by the same family, this home serves as a beautiful foundation for your future memories and personal design touches. Three bedrooms with a traditional layout which include rich hardwood flooring, adding a layer

    Linda Pelton Taylor Properties

    410 Walnut Dr, Annapolis, MD 21403
  • 48 E Lake Dr, Annapolis, MD 21403
    48 E Lake Dr, Annapolis, MD 21403
    48 E Lake Dr, Annapolis, MD 21403
    /28

    $1,895,000

    • Land
    • 9,583 Sq Ft
    • $8,613,636 per Acre

    48 E Lake Dr, Annapolis, MD 21403

    Once-in-a-Lifetime Opportunity to Build Your Dream Waterfront Home in Bay Ridge. See potential plans in the pictures and meet the builder to discuss your dream home or bring your own builder. Don't miss your chance to own the last remaining waterfront lot in the prestigious and highly sought-after Bay Ridge community. This is a rare opportunity to design and build your dream home on a premium lot

    Colleen Smith EXP Realty, LLC

    48 E Lake Dr, Annapolis, MD 21403
  • 930 Astern Way Unit 510, Annapolis, MD 21401
    930 Astern Way Unit 510, Annapolis, MD 21401
    930 Astern Way Unit 510, Annapolis, MD 21401
    /50

    $289,000

    $11K PRICE DROP
    • 1 Bed
    • 1.5 Baths
    • 1,152 Sq Ft

    930 Astern Way Unit 510, Annapolis, MD 21401

    Price Improvement! Welcome to 930 Astern Way — now featuring a brand-new HVAC system and a new improved price! This completely renovated, spacious 1-bedroom, 11⁄2-bath condominium is located in the sought-after 55+ community of Heritage Harbour and offers modern comfort with worry-free, low-maintenance living. The open floor plan creates a bright and airy atmosphere, with abundant natural light

    Jack Papaleonti Academy Realty Inc.

    930 Astern Way Unit 510, Annapolis, MD 21401
  • 117 Sunset Dr, Annapolis, MD 21403
    117 Sunset Dr, Annapolis, MD 21403
    117 Sunset Dr, Annapolis, MD 21403
    /81

    $874,900

    Open Sun 1PM - 3PM
    • 3 Beds
    • 2.5 Baths
    • 2,400 Sq Ft

    117 Sunset Dr, Annapolis, MD 21403

    Experience the best of the Annapolis maritime lifestyle in this beautifully renovated coastal-inspired home, ideally located in the sought-after Hillsmere Shores community one block from the marina, private beach, waterfront playground/parks, community pool, and boat ramp. Thoughtfully redesigned with high-end finishes throughout, this turnkey home offers the perfect blend of style, flexibility,

    Kate Hopkins Coldwell Banker Realty

    117 Sunset Dr, Annapolis, MD 21403
  • 1812 Shore Dr, Annapolis, MD 21401
    1812 Shore Dr, Annapolis, MD 21401
    1812 Shore Dr, Annapolis, MD 21401
    /101

    $1,149,000

    $51K PRICE DROP
    • 5 Beds
    • 4 Baths
    • 3,240 Sq Ft

    1812 Shore Dr, Annapolis, MD 21401

    Enjoy unobstructed views of Saltworks Creek from this ideally situated home in the sought-after, water-privileged community of Severn Grove—just minutes from downtown Annapolis. Thoughtfully designed across three spacious levels, the home offers an open, light-filled floor plan that seamlessly blends everyday comfort with effortless entertaining, all defined by picturesque water views. The main

    Day Weitzman Coldwell Banker Realty

    1812 Shore Dr, Annapolis, MD 21401
  • 312 Severn Ave Unit W-401, Annapolis, MD 21403
    312 Severn Ave Unit W-401, Annapolis, MD 21403
    312 Severn Ave Unit W-401, Annapolis, MD 21403
    /49

    $485,000

    • 1 Bed
    • 1 Bath
    • 660 Sq Ft

    312 Severn Ave Unit W-401, Annapolis, MD 21403

    Perched on the top floor of The Tecumseh, Maryland’s first condominium building, this two-level loft offers beautiful water views and an exceptional Eastport lifestyle. W401 overlooks Spa Creek with views of Ego Alley, the community marina, and Severn Avenue. This 1-bedroom, 1-bath residence features an open-concept main level with living and dining areas, a well-equipped kitchen, mechanical

    Ashley Stanwick Coldwell Banker Realty

    312 Severn Ave Unit W-401, Annapolis, MD 21403
  • 3344 Harness Creek Rd, Annapolis, MD 21403
    3344 Harness Creek Rd, Annapolis, MD 21403
    3344 Harness Creek Rd, Annapolis, MD 21403
    /50

    $10,850,000

    • 4 Beds
    • 7 Baths
    • 8,264 Sq Ft

    3344 Harness Creek Rd, Annapolis, MD 21403

    An extraordinary expression of waterfront luxury, this architecturally significant estate represents a rare convergence of world class design, craftsmanship, and lifestyle. Located within the prestigious enclave of Wimbledon Farms, surrounded by grand estates and moments from local vineyards and equestrian facilities, the residence was masterfully conceived by acclaimed architect Scarlett

    Brad Kappel TTR Sotheby's International Realty

    3344 Harness Creek Rd, Annapolis, MD 21403
  • 2045 Maidstone Farm Rd, Annapolis, MD 21409
    2045 Maidstone Farm Rd, Annapolis, MD 21409
    2045 Maidstone Farm Rd, Annapolis, MD 21409
    /50

    $12,950,000

    • 6 Beds
    • 9 Baths
    • 15,859 Sq Ft

    2045 Maidstone Farm Rd, Annapolis, MD 21409

    Imagine arriving home each day to a place where the pace slows, the views stretch for miles, and every amenity for recreation, relaxation, and entertaining is right outside your door. Tucked away along the Chesapeake Bay, this extraordinary waterfront retreat offers a lifestyle that few properties can match, a private oasis where luxury and nature exist in perfect balance. Originally constructed

    Brad Kappel TTR Sotheby's International Realty

    2045 Maidstone Farm Rd, Annapolis, MD 21409
  • 2186 Chesapeake Harbour Dr E, Annapolis, MD 21403
    2186 Chesapeake Harbour Dr E, Annapolis, MD 21403
    2186 Chesapeake Harbour Dr E, Annapolis, MD 21403
    /55

    $1,595,000

    • 3 Beds
    • 3.5 Baths
    • 2,307 Sq Ft

    2186 Chesapeake Harbour Dr E, Annapolis, MD 21403

    Set elegantly along the marina within the prestigious Chesapeake Harbour, this waterfront townhouse presents a refined composition of craftsmanship, material integrity, and coastal elegance. Moments from the historic charm of Annapolis and the open horizon of the Chesapeake Bay, the residence captures a rare harmony between luxury living and a serene waterfront setting.The interiors reveal a

    Alexander Esfahani Coldwell Banker Realty - Washington

    2186 Chesapeake Harbour Dr E, Annapolis, MD 21403
  • 278 Hillsmere Dr, Annapolis, MD 21403
    278 Hillsmere Dr, Annapolis, MD 21403
    278 Hillsmere Dr, Annapolis, MD 21403
    /14

    $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
  • 2900 Shipmaster Way, Annapolis, MD 21401
    2900 Shipmaster Way, Annapolis, MD 21401
    2900 Shipmaster Way, Annapolis, MD 21401
    /43

    $285,000

    • 2 Beds
    • 2 Baths
    • 1,018 Sq Ft

    2900 Shipmaster Way, Annapolis, MD 21401

    Welcome to this beautifully updated end-unit condo in the desirable Clipper Cay building of Heritage Harbour! Featuring luxury vinyl plank flooring and professional staging, this move-in-ready home offers both style and convenience. One of its most sought-after features is the private exterior entrance, allowing you to access the condo directly from the parking lot without going through the

    Jack Papaleonti Academy Realty Inc.

    2900 Shipmaster Way, Annapolis, MD 21401
  • 54 Decatur Ave, Annapolis, MD 21403
    54 Decatur Ave, Annapolis, MD 21403
    54 Decatur Ave, Annapolis, MD 21403
    /63

    $980,000

    Coming Soon
    • 3 Beds
    • 2 Baths
    • 2,035 Sq Ft

    54 Decatur Ave, Annapolis, MD 21403

    Don't MISS this RARE OPPORTUNITY IN THE VERY POPULAR COMMUNITY OF BAY RIDGE. .7460 Acres ! Make this PROPERTY Your Own! USE YOUR IMAGINATION! THE BAY RIDGE LIFESTYLE IS UNMATCHED IN ALL OF MARYLAND! SUPERIOR WATER ACCESS, STEPS TO COMMUNITY POOL/CLUBHOUSE W/ WATERCRAFT STORAGE RACKS , PRIVATE COMMUNITY BEACHES! & THE BIG WOODS "BAY RIDGE CONSERVATION AREA” W/TRAILS AND ACCESS TO BLACKWALNUT

    Gary Schneider Long & Foster Real Estate, Inc.

    54 Decatur Ave, Annapolis, MD 21403
  • 7101 Bay Front Dr Unit 202, Annapolis, MD 21403
    7101 Bay Front Dr Unit 202, Annapolis, MD 21403
    7101 Bay Front Dr Unit 202, Annapolis, MD 21403
    /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
  • 2020 Quay Village Ct Unit T1, Annapolis, MD 21403
    2020 Quay Village Ct Unit T1, Annapolis, MD 21403
    2020 Quay Village Ct Unit T1, Annapolis, MD 21403
    /45

    $700,000

    • 1 Bed
    • 1 Bath
    • 1,000 Sq Ft

    2020 Quay Village Ct Unit T1, Annapolis, MD 21403

    OPEN Sunday 10 -12 NOOON === WATERFRONT= ONE BEDROOM "C" FLOOR PLAN = EXTRA WIDE CONDO: Four pane sliders in living room and there are 4 glass pane windows in master bedroom == Master has a private exit door to a beach front patio == Front row seats for the Blue Angels flyover and weekly regatta races ... Amenities galore with two community pools / pool house complexes - one directly on the bay

    Candice Friday Coastal Realty Maryland

    2020 Quay Village Ct Unit T1, Annapolis, MD 21403
  • 529 Lee Cir, Annapolis, MD 21403
    529 Lee Cir, Annapolis, MD 21403
    529 Lee Cir, Annapolis, MD 21403
    /105

    $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
  • 703 Glendon Ave, Annapolis, MD 21403
    703 Glendon Ave, Annapolis, MD 21403
    703 Glendon Ave, Annapolis, MD 21403
    /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
  • 1709 Point no Point Dr, Annapolis, MD 21401
    1709 Point no Point Dr, Annapolis, MD 21401
    1709 Point no Point Dr, Annapolis, MD 21401
    /38

    $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
Maryland Anne Arundel County Annapolis

Real Estate & Homes for Sale in Annapolis, MD

Home Prices in Annapolis, MD

The median home sale price in Annapolis, MD is $632,500, up 2% year-over-year. Homes in Annapolis sell in 36 days on average, compared to the national average of 57 days.

Home Price Trends

Median Sale Price
$632,500
Median Single Family Sale Price
$839,900
Median Townhouse Sale Price
$456,000
Median 2 Bedroom Sale Price
$457,000
Median 1 Bedroom Sale Price
$429,750
Average Price Per Sq Ft
$360
Number of Homes for Sale
287
Last 12 months Home Sales
1,320
Months of Supply
2.60
Median List Price
$651,250
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
2%

Popular Home Searches in Annapolis, MD

In Annapolis, waterfront living and historic charm are top priorities, especially near Eastport and the historic district.

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