320

Luxury Homes for Sale in Annapolis, MD

Section Image Section Image
  • 5 Franklin St, Annapolis, MD 21401
    5 Franklin St, Annapolis, MD 21401
    5 Franklin St, Annapolis, MD 21401
    /47

    $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
    /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
  • 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
  • 3285 Harness Creek Rd, Annapolis, MD 21403
    3285 Harness Creek Rd, Annapolis, MD 21403
    3285 Harness Creek Rd, Annapolis, MD 21403
    /80

    $9,500,000

    • 6 Beds
    • 10 Baths
    • 10,745 Sq Ft

    3285 Harness Creek Rd, Annapolis, MD 21403

    Located on a private 2.5-acre lot in Wimbledon Farms, this waterfront estate home, designed by Cathy Purple Cherry and constructed by West River Builders, is truly a masterpiece in design and quality. The 3-level home – complete with elevator -- takes full advantage of its waterfront setting that includes 400 ft of shoreline. Facing Quiet Waters Park, the ever-changing view includes brilliant

    Agent Photo

    Reid Buckley

    Long & Foster Real Estate, Inc.

    3285 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
    /58

    $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
  • 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

    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
    /41

    $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

    Brad Kappel TTR Sotheby's International Realty

    1 Shipwright Harbor, Annapolis, MD 21401
  • 140 Spa Dr, Annapolis, MD 21403
    140 Spa Dr, Annapolis, MD 21403
    140 Spa Dr, Annapolis, MD 21403
    /89

    $4,600,000

    • 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

    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
    • 7 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
  • 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
  • 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
  • 16 Maryland Ave, Annapolis, MD 21401
    16 Maryland Ave, Annapolis, MD 21401
    16 Maryland Ave, Annapolis, MD 21401
    /94

    $3,449,000

    $400K PRICE DROP
    • 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
  • 48 E Lake Dr, Annapolis, MD 21403
    48 E Lake Dr, Annapolis, MD 21403
    48 E Lake Dr, Annapolis, MD 21403
    /27

    $3,395,000

    New Construction $200K PRICE DROP
    • 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
  • 203 Cape Saint John Rd, Annapolis, MD 21401
    203 Cape Saint John Rd, Annapolis, MD 21401
    203 Cape Saint John Rd, Annapolis, MD 21401
    /108

    $3,375,000

    • 5 Beds
    • 6.5 Baths
    • 7,230 Sq Ft

    203 Cape Saint John Rd, Annapolis, MD 21401

    Nestled in the serene enclave of Cape St. John, this exquisite coastal residence offers a harmonious blend of luxury and comfort, perfectly designed for an elevated lifestyle. Built in 2012, this stunning detached home showcases timeless architectural elegance with its brick and HardiPlank exterior, inviting you into a world of sophistication. Step inside to discover an expansive open floor plan

    Elizabeth Heinsohn Long & Foster Real Estate, Inc.

    203 Cape Saint John Rd, 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
  • 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 prestigious King George Street in the heart of Historic Annapolis, 238 King George Street represents an increasingly rare opportunity to acquire a beautifully reimagined residence in a location that simply cannot be replicated. The United States Naval Academy, State Circle, City Dock, waterfront dining, boutiques, galleries and yacht clubs are all just moments from the

    Wendy Oliver Coldwell Banker Realty

    238 King George St, Annapolis, MD 21401
  • 113 Bay Dr, Annapolis, MD 21403
    113 Bay Dr, Annapolis, MD 21403
    113 Bay Dr, Annapolis, MD 21403
    /52

    $2,795,000

    • 3 Beds
    • 2.5 Baths
    • 2,286 Sq Ft

    113 Bay Dr, Annapolis, MD 21403

    Live authentically. The Chesapeake Bay is the view, the backdrop and the reason to linger. From the covered bluestone porch, the horizon opens across the Bay with uninterrupted sky and water. Morning coffee, an afternoon breeze through open doors, evenings around the fire—the water sets the pace.Extensively renovated inside and out since 2019, this charming craftsman styled gem in the

    Agent Photo

    Elizabeth Atwood

    Krauss Real Property Brokerage

    113 Bay Dr, Annapolis, MD 21403
  • 507 First St, Annapolis, MD 21403
    507 First St, Annapolis, MD 21403
    507 First St, Annapolis, MD 21403
    /41

    $2,695,000

    • 4 Beds
    • 3.5 Baths
    • 3,947 Sq Ft

    507 First St, Annapolis, MD 21403

    Celebrate the Eastport lifestyle in this beautifully crafted home, where classic Craftsman character meets the comfort and ease of newer construction. Built in 2016 and lightly lived in, the home captures everything that makes Eastport so desirable, from its welcoming front porch, charming architectural details, and beautifully curated landscaping to a location just steps from marinas,

    Brad Kappel TTR Sotheby's International Realty

    507 First St, Annapolis, MD 21403
  • 703 Glendon Ave, Annapolis, MD 21403
    703 Glendon Ave, Annapolis, MD 21403
    703 Glendon Ave, Annapolis, MD 21403
    /53

    $2,695,000

    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 close to starting to build, just need your tweaks and finishes. 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

    Colleen Smith EXP Realty, LLC

    703 Glendon Ave, 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
  • 4 Ridge Rd, Annapolis, MD 21401
    4 Ridge Rd, Annapolis, MD 21401
    4 Ridge Rd, Annapolis, MD 21401
    /70

    $2,499,500

    Open Sat 12PM - 1:30PM Coming Soon Sep 24
    • 6 Beds
    • 5.5 Baths
    • 5,065 Sq Ft

    4 Ridge Rd, Annapolis, MD 21401

    There are houses that simply check the boxes, and then there are houses that have a sense of place. Tucked away at the end of a quiet street in the coveted Wardour neighborhood, this beautifully crafted custom home is filled with the details that make a house memorable: gorgeous millwork, custom built-ins, gracious rooms, beautiful gardens and spaces designed for both gathering and

    Heather Perkins Cummings & Co. Realtors

    4 Ridge Rd, 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

    $2,495,000

    $485K 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
  • 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
  • 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
  • 62 Southgate Ave, Annapolis, MD 21401
    62 Southgate Ave, Annapolis, MD 21401
    62 Southgate Ave, Annapolis, MD 21401
    /71

    $2,250,000

    $150K PRICE DROP
    • 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
  • 1614 Annesley Ct, Annapolis, MD 21401
    1614 Annesley Ct, Annapolis, MD 21401
    1614 Annesley Ct, Annapolis, MD 21401
    /46

    $2,250,000

    • 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
  • 120 Island View Dr, Annapolis, MD 21401
    120 Island View Dr, Annapolis, MD 21401
    120 Island View Dr, Annapolis, MD 21401
    /135

    $1,999,900

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

    120 Island View Dr, Annapolis, MD 21401

    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 panoramic views of Gingerville Creek. Situated at the end of a quiet cul-de-sac, this exceptional property combines luxury, privacy, and an unbeatable location just minutes from Annapolis. Commuters will love the convenience of being just

    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 14 residential lots.

    Alex Tower Sears TTR Sotheby's International Realty

    1016 E College Pkwy, 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

    Please see virtual house showcase listing from Zillow and read house bio in documents.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

    Christy Bishop Berkshire Hathaway HomeServices PenFed Realty

    1739 Vineyard Trail, 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
  • 192 Duke of Gloucester St, Annapolis, MD 21401
    192 Duke of Gloucester St, Annapolis, MD 21401
    192 Duke of Gloucester St, Annapolis, MD 21401
    /47

    $1,950,000

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

    192 Duke of Gloucester St, Annapolis, MD 21401

    Welcome to the Thomas Hyde House – a rare opportunity to own a piece of Annapolis history in the heart of downtown. Built in 1769, this impeccably restored Federal- style property blends 18th-century charm with modern luxury. Perfectly situated on sought- after Duke of Gloucester Street, this vibrant and colorful home offers stunning views of the Maryland State House and extremely rare off-street

    Hanh Pham Samson Properties

    192 Duke of Gloucester St, Annapolis, MD 21401
  • 400 Jefferson St, Annapolis, MD 21403
    400 Jefferson St, Annapolis, MD 21403
    400 Jefferson St, Annapolis, MD 21403
    /40

    $1,925,000

    Open Sat 1PM - 3PM $25K PRICE DROP
    • 4 Beds
    • 4 Baths
    • 4,099 Sq Ft

    400 Jefferson St, Annapolis, MD 21403

    ***Owner financing available at 6%***Experience the best of the Annapolis lifestyle from this beautifully reimagined coastal Craftsman in the heart of Eastport. Ideally located within walking distance of downtown Annapolis, the waterfront, restaurants, shops, yacht clubs, marinas, and the many neighborhood amenities that make Eastport one of the area's most desirable communities, this

    Brad Kappel TTR Sotheby's International Realty

    400 Jefferson St, 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
  • 820 Bay Ridge Ave, Annapolis, MD 21403
    820 Bay Ridge Ave, Annapolis, MD 21403
    820 Bay Ridge Ave, Annapolis, MD 21403
    /48

    $1,875,000

    • 4 Beds
    • 4.5 Baths
    • 3,900 Sq Ft

    820 Bay Ridge Ave, Annapolis, MD 21403

    There is something unmistakably special about life in Eastport—and 820 Bay Ridge Ave captures it beautifully. Set within coveted Sailor’s Quay, this exceptional residence offers more than 4,000 square feet of sophisticated living across four beautifully finished levels, combining timeless architecture, thoughtful customization, and an effortless coastal sensibility just moments from the heart of

    Wendy Oliver Coldwell Banker Realty

    820 Bay Ridge Ave, Annapolis, MD 21403

Showing Results 1 - 40, Page 1 of 8

Maryland Anne Arundel County

Real Estate & Homes for Sale in Annapolis, MD

Annapolis, MD Home Prices vs. Nearby Neighborhoods

Annapolis, MD Parole Victor Haven Eastport Forest Villa
Median Home Price
$660,000
$575,000
$482,000
$767,500
$688,000
Median Sale Price
$640,000
+3% YoY
$560,000
+1% YoY
$465,000
+8% YoY
$665,000
-21% YoY
$650,000
-5% YoY
Avg. Price per Square Foot
$357
$304
$363
$511
$414
Median Single Family Price
$845,000
$815,000
$624,900
$997,500
$844,950
Median Townhouse Price
$474,000
$522,450
$445,000
$577,000
$485,750
Median Condo Price
$415,000
$360,000
$405,000
$541,500
$630,000
Total Active Listings
320 listings
56 listings
35 listings
33 listings
27 listings
Market Conditions
3 Months of Supply
Seller's Market
2 Months of Supply
Seller's Market
5 Months of Supply
Balanced Market
4 Months of Supply
Seller's Market
4 Months of Supply
Seller's Market

Frequently Asked Questions

What is the average home price in Annapolis, MD?
Homes for sale in Annapolis, MD have an average home price of $930,230.
How many homes have sold over the last 12 months in Annapolis, MD?
1,299 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.
What are the most popular zip codes in Annapolis, MD?
The most popular zip codes in Annapolis, MD include 21403, 21401, 20708, 21037 and 21409.
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 $660,000. If you put a 20% down payment of $132,000 and had a 30-year fixed mortgage with an interest rate of 6.31%, your estimated principal and interest payment would be $3,270 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $140K 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.

Popular Home Searches in Annapolis, MD

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

How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group