27

Annapolis, MD Homes for Sale with Acreage

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  • 1717 Porters Hill Rd, Annapolis, MD 21401
    1717 Porters Hill Rd, Annapolis, MD 21401
    1717 Porters Hill Rd, Annapolis, MD 21401
    /27

    $1,300,000

    • 3 Beds
    • 2 Baths
    • 1,800 Sq Ft

    1717 Porters Hill Rd, Annapolis, MD 21401

    Welcome to 1717 Porters Hill Road, a light-filled contemporary home designed around volume and a seamless connection to its natural surroundings. Framed by expansive windows and soaring architectural lines, the home offers a fresh, airy interior where natural light moves beautifully throughout the day.Inside, the main living spaces unfold with an open floor plan that feels both modern and

    Agent Photo

    Reid Buckley

    Long & Foster Real Estate, Inc.

    1717 Porters Hill Rd, Annapolis, MD 21401
  • 1639 Colbert Rd, Annapolis, MD 21409
    1639 Colbert Rd, Annapolis, MD 21409
    1639 Colbert Rd, Annapolis, MD 21409
    /9

    $999,999

    New Construction Coming Soon Nov 1
    • 4 Beds
    • 3.5 Baths
    • 2,400 Sq Ft

    1639 Colbert Rd, Annapolis, MD 21409

    ALL PARTIES MUST SIGN HOLD HARMLESS AGREEMENT AND RETURN TO LISTING AGENT PRIOR TO ACCESSING THE PROPERTY. Welcome to an exceptional opportunity to build your dream waterfront estate at 1639 Colbert Road, Annapolis, MD 21409. Nestled on 5 private waterfront acres, this rare homesite offers the perfect blend of peaceful seclusion, natural beauty, and the convenience of Annapolis living.The

    Agent Photo

    Mada Nalley

    Douglas Realty, LLC

    1639 Colbert Rd, 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
  • 979 Bramleigh Ln, Annapolis, MD 21401
    979 Bramleigh Ln, Annapolis, MD 21401
    979 Bramleigh Ln, Annapolis, MD 21401
    /53

    $1,125,000

    • 4 Beds
    • 3.5 Baths
    • 4,080 Sq Ft

    979 Bramleigh Ln, Annapolis, MD 21401

    Welcome to this exceptional single-family home nestled in one of Annapolis' most desirable neighborhoods. Offering more than 4,000 square feet of thoughtfully designed living space, this beautiful residence features 4 spacious bedrooms, 3.5 bathrooms, and an ideal layout for both everyday living and entertaining. Step inside to an inviting open floor plan highlighted by a dramatic two-story great

    Robert Breeden Berkshire Hathaway HomeServices Homesale Realty

    979 Bramleigh Ln, Annapolis, MD 21401
  • 767 Bon Haven Dr, Annapolis, MD 21401
    767 Bon Haven Dr, Annapolis, MD 21401
    767 Bon Haven Dr, Annapolis, MD 21401
    /55

    $1,050,000

    $125K PRICE DROP
    • 5 Beds
    • 4 Baths
    • 3,255 Sq Ft

    767 Bon Haven Dr, Annapolis, MD 21401

    Discover luxurious living in this exceptional 5-bedroom, 4-bathroom home nestled on a full acre in an exclusive WATER ACCESS community. This meticulously crafted residence seamlessly blends elegant design with modern comfort, offering the perfect retreat for those seeking both tranquility and sophistication. The expansive one-acre lot offers endless possibilities for outdoor enjoyment, including

    Sean O'Connor Coldwell Banker Realty

    767 Bon Haven Dr, Annapolis, MD 21401
  • 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
  • 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
  • 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
  • 19 W Severn Ridge Rd, Annapolis, MD 21409
    19 W Severn Ridge Rd, Annapolis, MD 21409
    19 W Severn Ridge Rd, Annapolis, MD 21409
    /14

    $999,900

    Coming Soon Sep 12
    • 3 Beds
    • 4 Baths
    • 2,460 Sq Ft

    19 W Severn Ridge Rd, Annapolis, MD 21409

    Welcome to your private Annapolis retreat!Situated on a generous 1.4-acre lot, this quintessential Cape Cod offers the perfect blend of privacy, modern comfort, and convenience. Being just steps to the water and bikeable to Downtown Annapolis, this property is an ideal commuter's oasis.Step inside to discover an inviting, open floor plan designed for effortless living and entertaining.

    Tonia Falkowski Engel & Völkers Annapolis

    19 W Severn Ridge Rd, Annapolis, MD 21409
  • 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
  • 1353 Yorktown Rd, Annapolis, MD 21409
    1353 Yorktown Rd, Annapolis, MD 21409
    1353 Yorktown Rd, Annapolis, MD 21409
    /39

    $1,150,000

    New Construction $50K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,100 Sq Ft

    1353 Yorktown Rd, Annapolis, MD 21409

    Escape to your New Sanctuary on a 1.17 Acre Lot. Welcome to the Birch Model, one of our premier homes designed for those who desire the best in space, style, and comfort. This home offers everything you need for luxurious living.UP TO 5 Bedrooms: Perfect for large families or those who enjoy hosting guests, each bedroom is spacious and thoughtfully designed.UP TO 4.5 Bathrooms: Enjoy the

    Elizabeth Warren The Pinnacle Real Estate Co.

    1353 Yorktown Rd, Annapolis, MD 21409
  • 500 Sara Dr, Annapolis, MD 21401
    500 Sara Dr, Annapolis, MD 21401
    500 Sara Dr, Annapolis, MD 21401
    /35

    $1,750,000

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

    500 Sara Dr, Annapolis, MD 21401

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

    Brad Kappel TTR Sotheby's International Realty

    500 Sara Dr, Annapolis, MD 21401
  • 1322 Windsor Ridge Ln, Annapolis, MD 21409
    1322 Windsor Ridge Ln, Annapolis, MD 21409
    1322 Windsor Ridge Ln, Annapolis, MD 21409
    /98

    $1,699,000

    Open Sat 12PM - 2PM $101K PRICE DROP
    • 5 Beds
    • 5.5 Baths
    • 4,648 Sq Ft

    1322 Windsor Ridge Ln, Annapolis, MD 21409

    ** PRICE IMPROVEMENT** GREAT OPPORTUNITY TO OWN A PRIVATE LUXURY ESTATE ON THE BROADNECK PENINSULA!! Built in 2001, this stately brick Koch Colonial offers 4,648 square feet above grade and is nestled on a private 5.73-acre cul-de-sac lot in the highly sought-after Broadneck School District, delivering the perfect blend of luxury, privacy, and timeless elegance. Featuring a stunning 2022 gourmet

    Elizabeth DuLaney EXP Realty, LLC

    1322 Windsor Ridge Ln, 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
  • 1907 Mackiebeth Ct, Annapolis, MD 21401
    1907 Mackiebeth Ct, Annapolis, MD 21401
    1907 Mackiebeth Ct, Annapolis, MD 21401
    /103

    $1,500,000

    New Construction
    • 5 Beds
    • 4.5 Baths
    • 5,437 Sq Ft

    1907 Mackiebeth Ct, Annapolis, MD 21401

    This is a rare opportunity to own a newly built, beautifully designed home on a large lot in an established neighborhood-with nature at your doorstep and everything Annapolis has to offer just minutes away. This home is ready to go and can do a quick occupancy! With a stunning Colonial architectural style, this beautiful home offers 5-bedrooms and 4.5-baths and sits on the last available lot in

    Marilyn Hendley EXP Realty, LLC

    1907 Mackiebeth Ct, Annapolis, MD 21401
  • 1711 Ritchie Hwy, Annapolis, MD 21409
    1711 Ritchie Hwy, Annapolis, MD 21409
    1711 Ritchie Hwy, Annapolis, MD 21409
    /14

    $1,199,500

    Open Sat 11AM - 2PM
    • 5 Beds
    • 5 Baths
    • 5,086 Sq Ft

    1711 Ritchie Hwy, Annapolis, MD 21409

    Beautiful colonial home in the perfect Annapolis location. Nestled on over an acre of private, tree-lined grounds, this charming property offers a peaceful retreat while remaining conveniently close to everything Annapolis has to offer. Enjoy easy access to Route 50 and just minutes from the U.S. Naval Academy, downtown Annapolis, dining, shopping, and more. This beautifully maintained residence

    Kay Millett Taylor Properties

    1711 Ritchie Hwy, Annapolis, MD 21409
  • 3249 Arundel on The Bay Rd, Annapolis, MD 21403
    3249 Arundel on The Bay Rd, Annapolis, MD 21403
    3249 Arundel on The Bay Rd, Annapolis, MD 21403
    /83

    $895,000

    $5K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 4,288 Sq Ft

    3249 Arundel on The Bay Rd, Annapolis, MD 21403

    Welcome to 3249 Arundel On The Bay Road, an exceptional custom contemporary estate situated on over one private acre in one of Annapolis’ most exclusive waterfront communities. Appraised at $1,097,000 in January 2026, this remarkable property offers an incredible opportunity for instant equity while delivering the luxury lifestyle today's discerning buyers seek. A dramatic two-story foyer

    Montaz McCray Keller Williams Capital Properties

    3249 Arundel on The Bay Rd, Annapolis, MD 21403
  • 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
  • 718 Whitehall Beach Rd, Annapolis, MD 21409
    718 Whitehall Beach Rd, Annapolis, MD 21409
    718 Whitehall Beach Rd, Annapolis, MD 21409
    /95

    $1,550,000

    $50K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,788 Sq Ft

    718 Whitehall Beach Rd, Annapolis, MD 21409

    Price Improvement and Exceptional Value! A rare opportunity to own over 2 private acres in one of Annapolis’ most desirable waterfront communities. Complete with a private tennis court and backing to a sprawling horse farm, this exceptional property offers the perfect blend of privacy, recreation, and the Chesapeake lifestyle. Nestled in the sought-after Whitehall Beach neighborhood, residents

    Joanna Dalton Coldwell Banker Realty

    718 Whitehall Beach Rd, Annapolis, MD 21409
  • 2203 Mulberry Hill Rd, Annapolis, MD 21409
    2203 Mulberry Hill Rd, Annapolis, MD 21409
    2203 Mulberry Hill Rd, Annapolis, MD 21409
    /46

    $1,350,000

    • 3 Beds
    • 2.5 Baths
    • 4,400 Sq Ft

    2203 Mulberry Hill Rd, Annapolis, MD 21409

    Welcome to a waterfront retreat where timeless coastal living meets modern luxury. Perfectly positioned on approximately one private acre along the tranquil waters of Mill Creek with direct access to the Chesapeake Bay, this custom-built home offers the exceptional lifestyle that Annapolis is known for. Designed to capture breathtaking water views from nearly every room, this beautifully

    Ms. Kristina Boyd Keller Williams Preferred Properties

    2203 Mulberry Hill Rd, Annapolis, MD 21409
  • 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
  • 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
  • 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
  • 1812 Millridge Ct, Annapolis, MD 21409
    1812 Millridge Ct, Annapolis, MD 21409
    1812 Millridge Ct, Annapolis, MD 21409
    /60

    $1,250,000

    Coming Soon Sep 7
    • 4 Beds
    • 3 Baths
    • 3,555 Sq Ft

    1812 Millridge Ct, Annapolis, MD 21409

    Set on 2.5 beautifully landscaped acres in the desirable community of The Meadows, this distinctive three-sided brick home offers an impressive combination of privacy, spacious one-level living, custom features, and exceptional indoor and outdoor entertaining spaces. With four generously sized bedrooms and three full baths on the main level, the home provides a versatile floor plan rarely found

    Michele Cordle Long & Foster Real Estate, Inc.

    1812 Millridge Ct, Annapolis, MD 21409
  • 1838 Brett Ct, Annapolis, MD 21401
    1838 Brett Ct, Annapolis, MD 21401
    1838 Brett Ct, Annapolis, MD 21401
    /44

    $645,000

    Open Sun 1PM - 3PM $30K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,270 Sq Ft

    1838 Brett Ct, Annapolis, MD 21401

    This adorable split level home is located on a cul-de-sac in ROLLING HILLS! The sellers just had the interior painted, carpets replaced on the main and upper levels, and the vanity replaced in the primary bath—all on top of existing updates throughout. A generous asphalt driveway and meandering paver walkway create a wonderful first impression. Once inside, you'll find hardwood floors, a bright

    Jenn Klarman Long & Foster Real Estate, Inc.

    1838 Brett Ct, Annapolis, MD 21401
  • 1197 Carrs Rd, Annapolis, MD 21409
    1197 Carrs Rd, Annapolis, MD 21409
    1197 Carrs Rd, Annapolis, MD 21409
    /7

    $564,999

    Coming Soon Sep 11
    • 3 Beds
    • 2 Baths
    • 1,092 Sq Ft

    1197 Carrs Rd, Annapolis, MD 21409

    COUNTRY LIVING MEETS ANNAPOLIS CONVENIENCE! Welcome to this unique and peaceful 1-acre retreat tucked away just minutes from Sandy Point State Park and offering easy access toward Annapolis, the Bay Bridge and beyond. Beautifully landscaped grounds create a private, resort-like setting with mature greenery, hardscape walkways, a newer Trex deck installed within the past year, and a beautiful

    Maria Palacios Keller Williams Flagship

    1197 Carrs 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
Maryland Anne Arundel County

Homes for Sale with Acreage in Annapolis, MD

Home Prices in Annapolis, MD

The median home sale price in Annapolis, MD is $640,000, up 4% year-over-year. Homes in Annapolis sell in 35 days on average, compared to the national average of 55 days.

Home Price Trends

Median Sale Price
$640,000
Median Single Family Sale Price
$834,400
Median Townhouse Sale Price
$465,000
Median 2 Bedroom Sale Price
$450,000
Median 1 Bedroom Sale Price
$453,700
Average Price Per Sq Ft
$356
Number of Homes for Sale
292
Last 12 months Home Sales
1,311
Months of Supply
2.70
Median List Price
$651,250
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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In Annapolis, there are currently 27 homes for sale with acreage, providing ample space for homeowners to customize their living environment, whether for expansive gardens, outdoor entertaining, or enhanced privacy. Whether you're in search of a spacious family home with plenty of room to roam, a property ripe for development, or simply seeking space and tranquility, homes for sale with acreage in Annapolis, MD offer the flexibility to tailor your living experience to your preferences. Browse the selection of homes for sale with land in Annapolis and discover the potential and freedom that comes with owning your own piece of property.

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