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Luxury Homes for Sale in Annapolis, MD

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  • 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
  • 5 Franklin St, Annapolis, MD 21401
    5 Franklin St, Annapolis, MD 21401
    5 Franklin St, Annapolis, MD 21401
    /46

    $12,500,000

    • 5 Beds
    • 6.5 Baths
    • 5,993 Sq Ft

    5 Franklin St, Annapolis, MD 21401

    A rare opportunity on Spa Creek, this fully reimagined Murray Hill residence offers an extraordinary waterfront lifestyle just moments from downtown Annapolis. Completed in late 2023 after a full ground-up rebuild, the home spans 5,900+ sq. ft. of impeccably crafted living space, where natural materials, refined architectural details, and top-tier systems create a seamless blend of comfort and

    Brad Kappel TTR Sotheby's International Realty

    5 Franklin St, Annapolis, MD 21401
  • 8 Spa View Cir, Annapolis, MD 21401
    8 Spa View Cir, Annapolis, MD 21401
    8 Spa View Cir, Annapolis, MD 21401
    /58

    $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
  • 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
  • 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
  • 125 S Winchester Rd, Annapolis, MD 21409
    125 S Winchester Rd, Annapolis, MD 21409
    125 S Winchester Rd, Annapolis, MD 21409
    /47

    $7,500,000

    $1M PRICE DROP
    • 5 Beds
    • 7 Baths
    • 11,269 Sq Ft

    125 S Winchester Rd, Annapolis, MD 21409

    This Severn River estate is a rare opportunity to own one of the area’s most spectacular properties. Showcasing a negative-edge pool with beach entry and hot tub, 2 private piers to accommodate a variety of vessel sizes including a 100 ft slip, sprawling yard and sweeping views of the river and Naval Academy Bridge. Imagine waking each morning to the sun sparkling off the Severn, its reflection

    Brad Kappel TTR Sotheby's International Realty

    125 S Winchester Rd, Annapolis, MD 21409
  • 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
  • 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
  • 1524 Cedar Lane Farm Rd, Annapolis, MD 21409
    1524 Cedar Lane Farm Rd, Annapolis, MD 21409
    1524 Cedar Lane Farm Rd, Annapolis, MD 21409
    /50

    $6,995,000

    • 7 Beds
    • 5.5 Baths
    • 9,024 Sq Ft

    1524 Cedar Lane Farm Rd, Annapolis, MD 21409

    Escape to another world with this striking French modern waterfront estate. Exquisitely sited on a premium and private 4.15 acre lot with 600 feet of impressively rip-rapped water frontage, coveted waterfront pool, tennis court and picturesque views of the serene waters of Whitehall Creek. This ultra-luxe 9,000+ square-foot, 7 bedroom, 5.5 bathroom custom built home has been completely renovated.

    Brad Kappel TTR Sotheby's International Realty

    1524 Cedar Lane Farm Rd, Annapolis, MD 21409
  • 2562 Carrollton Rd, Annapolis, MD 21403
    2562 Carrollton Rd, Annapolis, MD 21403
    2562 Carrollton Rd, Annapolis, MD 21403
    /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
  • 1 Shipwright Harbor, Annapolis, MD 21401
    1 Shipwright Harbor, Annapolis, MD 21401
    1 Shipwright Harbor, Annapolis, MD 21401
    /39

    $5,675,000

    $223K PRICE DROP
    • 3 Beds
    • 3.5 Baths
    • 3,108 Sq Ft

    1 Shipwright Harbor, Annapolis, MD 21401

    Stately French Villa on Spa Creek in downtown Annapolis! This jewel box of a home was designed and built by a renowned local architect as the culmination of an award-winning career. Offered completely turn-key, this exceptional residence conveys fully furnished and thoughtfully appointed—including furniture, fully equipped kitchen, linens, etc —allowing you to arrive with nothing more than a

    Brad Kappel TTR Sotheby's International Realty

    1 Shipwright Harbor, Annapolis, MD 21401
  • 17151717 Porters Hill Rd, Annapolis, MD 21401
    17151717 Porters Hill Rd, Annapolis, MD 21401
    17151717 Porters Hill Rd, Annapolis, MD 21401
    /37

    $4,950,000

    • 7 Beds
    • 7 Baths
    • 7,500 Sq Ft

    17151717 Porters Hill Rd, Annapolis, MD 21401

    Ideally situated on the banks of Luce Creek with sweeping views down the Severn River, 1715-1717 Porters Hill Road is a unique heritage property with over a century of history. Set on a 2.96 acre lot with 429 ft of waterfrontage, the property is comprised of two separate parcels and includes a large, hard-to-find boathouse that provides both charm and utility for all your waterfront adventures.

    Agent Photo

    Reid Buckley

    Long & Foster Real Estate, Inc.

    17151717 Porters Hill Rd, Annapolis, MD 21401
  • 140 Spa Dr, Annapolis, MD 21403
    140 Spa Dr, Annapolis, MD 21403
    140 Spa Dr, Annapolis, MD 21403
    /6

    $4,600,000

    Coming Soon
    • 5 Beds
    • 3.5 Baths
    • 5,095 Sq Ft

    140 Spa Dr, Annapolis, MD 21403

    An extraordinary opportunity to own one of Annapolis’ most distinctive waterfront properties, offering some of the finest views on Spa Creek and the rare privilege of owning your own private marina in your backyard with dockside parking. Perfectly positioned to capture breathtaking panoramic vistas, this elegant Nantucket-inspired residence is filled with natural light, featuring walls of glass

    Agent Photo

    Biana Arentz

    Coldwell Banker Realty

    140 Spa Dr, Annapolis, MD 21403
  • 217 Lockwood Ct, Annapolis, MD 21403
    217 Lockwood Ct, Annapolis, MD 21403
    217 Lockwood Ct, Annapolis, MD 21403
    /66

    $4,500,000

    $495K PRICE DROP
    • 5 Beds
    • 4 Baths
    • 4,107 Sq Ft

    217 Lockwood Ct, Annapolis, MD 21403

    There are places where you visit the water, and there are places where the water becomes part of your everyday life. Perfectly positioned along the shores of Spa Creek in the heart of Eastport, this exceptional waterfront residence offers a front-row seat to one of Annapolis' most coveted lifestyles. Imagine stepping from your back door onto your private pier, casting off for an evening cruise, a

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

    217 Lockwood Ct, Annapolis, MD 21403
  • 14 E Lake Dr, Annapolis, MD 21403
    14 E Lake Dr, Annapolis, MD 21403
    14 E Lake Dr, Annapolis, MD 21403
    /49

    $3,997,000

    • 5 Beds
    • 6 Baths
    • 6,234 Sq Ft

    14 E Lake Dr, Annapolis, MD 21403

    Bay Ridge Waterfront! Built by Pilli Custom Homes and beautifully curated by Erin Paige Pitts Interiors, this exceptional waterfront residence blends timeless architecture, impeccable craftsmanship, and extraordinary attention to detail. Rich custom millwork, extensive crown molding, elegant wainscoting, and coffered ceilings create an atmosphere of refined luxury throughout. A welcoming

    Brad Kappel TTR Sotheby's International Realty

    14 E Lake Dr, Annapolis, MD 21403
  • 1100 Magothy Cir, Annapolis, MD 21409
    1100 Magothy Cir, Annapolis, MD 21409
    1100 Magothy Cir, Annapolis, MD 21409
    /46

    $3,850,000

    New Construction Open Sat 11AM - 1PM
    • 5 Beds
    • 4.5 Baths
    • 4,822 Sq Ft

    1100 Magothy Cir, Annapolis, MD 21409

    Discover the pinnacle of contemporary waterfront living in this extraordinary new construction residence by Cypress Homes, perfectly sited on a spectacular peninsula along the picturesque Little Magothy River. Surrounded by water on two sides and offering a rare 525 feet of waterfrontage, this remarkable property captures sweeping panoramic views extending across the Magothy River to the

    Brad Kappel TTR Sotheby's International Realty

    1100 Magothy Cir, Annapolis, MD 21409
  • 16 Maryland Ave, Annapolis, MD 21401
    16 Maryland Ave, Annapolis, MD 21401
    16 Maryland Ave, Annapolis, MD 21401
    /92

    $3,849,000

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

    16 Maryland Ave, Annapolis, MD 21401

    A truly exceptional historic residence is now available in the heart of downtown Annapolis. Welcome to 16 Maryland Avenue, a distinguished circa-1830 Greek Revival home masterfully restored in collaboration with the renowned Hammond-Wilson Architects. Perfectly positioned just steps from State Circle and the United States Naval Academy, this iconic three-story brick property seamlessly blends

    Joanna Dalton Coldwell Banker Realty

    16 Maryland Ave, Annapolis, MD 21401
  • 1715 Porters Hill Rd, Annapolis, MD 21401
    1715 Porters Hill Rd, Annapolis, MD 21401
    1715 Porters Hill Rd, Annapolis, MD 21401
    /52

    $3,750,000

    $200K PRICE DROP
    • 4 Beds
    • 6 Baths
    • 6,594 Sq Ft

    1715 Porters Hill Rd, Annapolis, MD 21401

    Ideally situated on the banks of Luce Creek with sweeping views down the Severn River, 1715 Porters Hill Road is a unique heritage property with over a century of history. Set on a 1.7 acre lot with 265 ft of waterfrontage, the property includes a large, hard-to-find boathouse that provides both charm and utility for all your waterfront adventures. The private pier has 7+ ft water depth and can

    Agent Photo

    Reid Buckley

    Long & Foster Real Estate, Inc.

    1715 Porters Hill Rd, Annapolis, MD 21401
  • 1668 Homewood Landing Rd, Annapolis, MD 21409
    1668 Homewood Landing Rd, Annapolis, MD 21409
    1668 Homewood Landing Rd, Annapolis, MD 21409
    /27

    $3,595,000

    New Construction
    • 6 Beds
    • 5.5 Baths
    • 5,718 Sq Ft

    1668 Homewood Landing Rd, Annapolis, MD 21409

    An extraordinary opportunity to create the luxury waterfront estate you've always envisioned. Perfectly positioned on a spectacular homesite offering approximately 120 feet of pristine shoreline and 8 feet of mean low water, this exceptional to-be-built custom residence by Whitehall Building & Co. combines timeless architecture, uncompromising craftsmanship, and an unparalleled waterfront

    Colleen Smith EXP Realty, LLC

    1668 Homewood Landing Rd, Annapolis, MD 21409
  • 48 E Lake Dr, Annapolis, MD 21403
    48 E Lake Dr, Annapolis, MD 21403
    48 E Lake Dr, Annapolis, MD 21403
    /21

    $3,595,000

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 4,029 Sq Ft

    48 E Lake Dr, Annapolis, MD 21403

    Once-in-a-Lifetime Opportunity to Build Your Dream Waterfront Home in Bay Ridge. Don't miss your chance to own the last remaining waterfront lot and be in your new home by next boating season in the prestigious and highly sought-after Bay Ridge community. This is a rare opportunity to work with the builder to design and build your dream home on a premium lot offering 57 feet of serene waterfront

    Colleen Smith EXP Realty, LLC

    48 E Lake Dr, Annapolis, MD 21403
  • 5 Market Quay, Annapolis, MD 21401
    5 Market Quay, Annapolis, MD 21401
    5 Market Quay, Annapolis, MD 21401
    /78

    $3,499,000

    $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
  • 9 Shipwright St, Annapolis, MD 21401
    9 Shipwright St, Annapolis, MD 21401
    9 Shipwright St, Annapolis, MD 21401
    /46

    $3,495,000

    • 3 Beds
    • 2.5 Baths
    • 2,621 Sq Ft

    9 Shipwright St, Annapolis, MD 21401

    Quintessential downtown Annapolis waterfront home on the sparkling waters of Spa Creek! This amazing property combines the best of both worlds; the charming historic feel of a downtown Annapolis home with the premier waterfront lifestyle that every resident is looking for. Nestled on a quiet street, this home is the perfect size for an easy to own, lock up and go property. With 3 bedrooms and 2.5

    Brad Kappel TTR Sotheby's International Realty

    9 Shipwright St, Annapolis, MD 21401
  • 1800 River Watch Ln, Annapolis, MD 21401
    1800 River Watch Ln, Annapolis, MD 21401
    1800 River Watch Ln, Annapolis, MD 21401
    /69

    $3,195,000

    $300K PRICE DROP
    • 3 Beds
    • 4,223 Sq Ft

    1800 River Watch Ln, Annapolis, MD 21401

    Set on a private peninsula with more than 450 feet of water frontage on Luce Creek, just off the Severn River, 1800 River Watch Lane offers a rare combination of modern sophistication and effortless single-level living. Meticulously renovated by the current owners, this contemporary rambler embraces water views from nearly every room. Guests arrive via a long, private drive and circular pea-stone

    Doc Keane Washington Fine Properties, LLC

    1800 River Watch Ln, 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
  • 1979 Baltimore Annapolis Blvd, Annapolis, MD 21409
    1979 Baltimore Annapolis Blvd, Annapolis, MD 21409
    1979 Baltimore Annapolis Blvd, Annapolis, MD 21409
    /83

    $3,000,000

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

    1979 Baltimore Annapolis Blvd, Annapolis, MD 21409

    A truly extraordinary opportunity awaits in one of Annapolis' most coveted waterfront locations. Situated in the historic Ferry Farms neighborhood, 1979 Baltimore Annapolis Boulevard is one of only thirteen homes positioned directly across the Severn River from the U.S. Naval Academy, offering uninterrupted panoramic views that have captivated generations. Imagine enjoying the Blue Angels soaring

    Alison Wisnom Coldwell Banker Realty

    1979 Baltimore Annapolis Blvd, Annapolis, MD 21409
  • 1486 Downham Market, Annapolis, MD 21401
    1486 Downham Market, Annapolis, MD 21401
    1486 Downham Market, Annapolis, MD 21401
    /87

    $2,999,900

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

    1486 Downham Market, Annapolis, MD 21401

    There are waterfront homes...and then there are waterfront estates that redefine luxury. Welcome to 1486 Downham Market, an extraordinary deep-water retreat in the prestigious Downs on the Severn, where timeless architecture, exceptional craftsmanship, and one of the finest protected waterfront settings in the region come together to create a home that is truly without equal. Perfectly positioned

    Wendy Oliver Coldwell Banker Realty

    1486 Downham Market, Annapolis, MD 21401
  • 238 King George St, Annapolis, MD 21401
    238 King George St, Annapolis, MD 21401
    238 King George St, Annapolis, MD 21401
    /53

    $2,950,000

    • 4 Beds
    • 5 Baths
    • 3,750 Sq Ft

    238 King George St, Annapolis, MD 21401

    Perfectly positioned on one of the most coveted streets in Historic Annapolis, just steps from State Circle, the United States Naval Academy, City Dock, waterfront dining, boutiques, and yacht clubs, 238 King George Street offers a rare opportunity to own a completely reimagined luxury residence in the heart of Maryland’s capital city. Blending timeless historic charm with the modern conveniences

    Wendy Oliver Coldwell Banker Realty

    238 King George St, Annapolis, MD 21401
  • 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
  • 202 Wardour Dr, Annapolis, MD 21401
    202 Wardour Dr, Annapolis, MD 21401
    202 Wardour Dr, Annapolis, MD 21401
    /59

    $2,765,000

    • 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
  • 3733 Thomas Point Rd, Annapolis, MD 21403
    3733 Thomas Point Rd, Annapolis, MD 21403
    3733 Thomas Point Rd, Annapolis, MD 21403
    /46

    $2,685,000

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

    3733 Thomas Point Rd, Annapolis, MD 21403

    Life takes on a different pace in Oakwood, where the calm waters of Fishing Creek and the South River provide an idyllic backdrop and effortless access to the Chesapeake Bay. With 93 feet of shoreline, a private pier with multiple slips, and a substantial 25,000-pound boat lift, this property is perfectly suited for boating enthusiasts and those who appreciate the beauty and tranquility of the

    Brad Kappel TTR Sotheby's International Realty

    3733 Thomas Point Rd, Annapolis, MD 21403
  • 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
  • 62 Southgate Ave, Annapolis, MD 21401
    62 Southgate Ave, Annapolis, MD 21401
    62 Southgate Ave, Annapolis, MD 21401
    /75

    $2,400,000

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

    62 Southgate Ave, Annapolis, MD 21401

    Nestled on one of the most picturesque streets in Annapolis, this utterly charming Murray Hill home blends timeless character with thoughtful modern updates. A welcoming wraparound porch overlooks the beautifully landscaped front yard, complete with a stunning dogwood tree, while the fenced backyard offers a private courtyard patio that's perfect for outdoor entertaining. A rare 24' x 22'

    Mary Kay Gordon Coldwell Banker Realty

    62 Southgate Ave, 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
  • 327 Riverview Trail, Annapolis, MD 21401
    327 Riverview Trail, Annapolis, MD 21401
    327 Riverview Trail, Annapolis, MD 21401
    /42

    $2,349,000

    $146K PRICE DROP
    • 3 Beds
    • 3.5 Baths
    • 1,831 Sq Ft

    327 Riverview Trail, Annapolis, MD 21401

    Picturesque Craftsman-style waterfront cottage in Epping Forest! Mornings begin with coffee on the porch as the water glistens across Saltworks Creek and stretches out to the Severn River, while evenings are spent gathered by the firepit, watching boats drift by under painted skies. Welcome to effortless waterfront living in the private, gated community of Epping Forest where every day feels like

    Brad Kappel TTR Sotheby's International Realty

    327 Riverview Trail, 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
  • 500 Sara Dr, Annapolis, MD 21401
    500 Sara Dr, Annapolis, MD 21401
    500 Sara Dr, Annapolis, MD 21401
    /35

    $2,250,000

    • 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
  • 1614 Annesley Ct, Annapolis, MD 21401
    1614 Annesley Ct, Annapolis, MD 21401
    1614 Annesley Ct, Annapolis, MD 21401
    /46

    $2,250,000

    Open Sun 11AM - 2PM
    • 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
  • 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

    $1,999,999

    • 4 Beds
    • 3.5 Baths
    • 3,042 Sq Ft

    146 Duke of Gloucester St, Annapolis, MD 21401

    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 updated throughout, this

    Rob Carter Douglas Realty, LLC

    146 Duke of Gloucester St, Annapolis, MD 21401
  • 120 Island View Dr, Annapolis, MD 21401
    120 Island View Dr, Annapolis, MD 21401
    120 Island View Dr, Annapolis, MD 21401
    /94

    $1,999,900

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

    120 Island View Dr, Annapolis, MD 21401

    COMING SOON – Available August 16, 2026! Floor plans, and a full virtual tour are coming soon. The current online photos are only a preview of what is truly one of the most spectacular waterfront properties to hit the market this year. Prepare to be amazed by this rare waterfront opportunity offering 4 bedrooms, 4.5 baths with over 3000 square feet of living space with approximately 270-degree

    Boyd Grainger Pearson Smith Realty, LLC

    120 Island View Dr, Annapolis, MD 21401
  • 1016 E College Pkwy, Annapolis, MD 21409
    1016 E College Pkwy, Annapolis, MD 21409
    /2

    $1,995,000

    • Land
    • 23.33 Acres
    • $85,512 per Acre

    1016 E College Pkwy, Annapolis, MD 21409

    23-acre parcel zoned primarily R-1, with some O-S. Preliminary engineering work indicates the property can be subdivided and coul support multiple residential lots. The concept drawing attached.

    Alex Tower Sears TTR Sotheby's International Realty

    1016 E College Pkwy, Annapolis, MD 21409

Showing Results 1 - 40, Page 1 of 8

Maryland Anne Arundel County

Real Estate & Homes for Sale in Annapolis, MD

Frequently Asked Questions

What is the average home price in Annapolis, MD?
Homes for sale in Annapolis, MD have an average home price of $963,847.
How many homes have sold over the last 12 months in Annapolis, MD?
1,314 homes have sold in Annapolis, MD over the last 12 months.
What is the average household income in Annapolis, MD?
The average household income in Annapolis, MD is $125K.
Is Annapolis, MD a safe city?
In general, the safest neighborhoods in Annapolis, MD with lower crime scores are Parole, Victor Haven, Eastport, Tyler Heights-Primrose Acres and West Annapolis-Wardour.
What are the most popular zip codes in Annapolis, MD?
The most popular zip codes in Annapolis, MD include 21403, 21401, 21037, 21409 and 21012.
What are the most popular neighborhoods in Annapolis, MD?
The most popular neighborhoods in Annapolis, MD with the most homes for sale are Parole, Victor Haven, Eastport, Downtown Annapolis and Forest Villa.
How much do you need to make to afford a house in Annapolis?
The median home price in Annapolis is $655,000. If you put a 20% down payment of $131,000 and had a 30-year fixed mortgage with an interest rate of 6.69%, your estimated principal and interest payment would be $3,380 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $145K a year to afford the median home price in Annapolis. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Annapolis is $125K.
How are the schools in Annapolis, MD?
Annapolis, MD has highly rated public and private schools. Some of the best schools in Annapolis based on Niche Grades are Key School, St Martins Lutheran Church School and Saint Andrew's Day School. The neighborhoods in Annapolis with the highest rated schools are Parole, Victor Haven and Eastport. Browse all the schools in Annapolis, MD to learn more.

Home Prices in Annapolis, MD

The median home sale price in Annapolis, MD is $636,250, up 4% year-over-year. Homes in Annapolis sell in 36 days on average, compared to the national average of 56 days.

Home Price Trends

Median Sale Price
$636,250
Median Single Family Sale Price
$849,000
Median Townhouse Sale Price
$465,000
Median 2 Bedroom Sale Price
$454,950
Median 1 Bedroom Sale Price
$403,750
Average Price Per Sq Ft
$360
Number of Homes for Sale
272
Last 12 months Home Sales
1,314
Months of Supply
2.50
Median List Price
$655,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
4%

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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