32

Annapolis, MD Homes for Sale with Acreage

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  • /56

    $1,000,000

    • 4 Beds
    • 4 Baths
    • 3,200 Sq Ft

    2977 Southaven Dr, Annapolis, MD 21401

    This stunning log home on 2.48 scenic acres (with the potential to subdivide) offers the perfect blend of rustic elegance and thoughtful upgrades. Surrounded by lush landscaping, the property provides treetop views and a glimpse of the water during the winter months. The impressive two-story living room showcases a dramatic wood-burning fireplace and flows effortlessly into the dining area and

    Agent Photo

    Scott Smolen

    RE/MAX Leading Edge

    (410) 846-6686

    2977 Southaven Dr, Annapolis, MD 21401
  • /2

    $1,300,500 Coming Soon

    • 5 Beds
    • 3 Baths
    • 5,465 Sq Ft

    15 E Nap Ln, Annapolis, MD 21409

    Coming Soon! Get ready to fall in love with this Annapolis gem Nestled in the sought-after Captain Cove neighborhood on a 1.21-acre wooded lot, this beautifully maintained home is minutes from downtown Annapolis.Unique features include a rooftop deck, expansive back decking, and a bonus treehouse that doubles as a fun space for children or a peaceful retreat for adults—perfect as a she shed or

    Agent Photo

    Litra Simms

    Simms and Associates

    (443) 339-8629

    15 E Nap Ln, Annapolis, MD 21409
  • /58

    $1,250,000

    • 3 Beds
    • 2.5 Baths
    • 2,926 Sq Ft

    210 Providence Rd, Annapolis, MD 21409

    This modern ('85) 4 bedroom/2 full- 1 half- bath home, sits on the largest lot (1.5 acres) in the coveted Providence community, borders the USNA Golf Course, and is the largest estate lot currently available in Annapolis. The lucky buyer will become a member of the private Providence Club, a $10 million "clubhouse" which includes an 8-year new clubhouse, pool and kids play area all with

    Jonathan Scheffenacker Redfin Corp

    210 Providence Rd, Annapolis, MD 21409
  • /65

    $735,000

    • 3 Beds
    • 3.5 Baths
    • 2,540 Sq Ft

    515 Corbin Pkwy, Annapolis, MD 21401

    Come see this great 3 bedroom, 3.5 bath rancher set on 2 acres located in the highly sought after neighborhood of Rolling hills located close to Historic Annapolis and convenient to shopping, restaurants and health care! The beautiful spacious kitchen is a welcoming place for entertaining and is complete with a large island with a cooktop with a downdraft, stainless steel appliances that include

    Lynn Ikle Redfin Corp

    515 Corbin Pkwy, Annapolis, MD 21401
  • /121

    $5,250,000

    • 5 Beds
    • 3.5 Baths
    • 3,945 Sq Ft

    917 Arbutus Rd, Annapolis, MD 21403

    Welcome to 917 Arbutus Road—an extraordinary waterfront property nestled on 5 private acres with deep water on Crab Creek minutes from downtown Annapolis. This mid-century modern home offers over 3656 SF of light-filled living space, with soaring ceilings, expansive glass walls, and panoramic views of water and nature. The main level boasts four bedrooms and open-concept living areas designed

    Georgie Berkinshaw Coldwell Banker Realty

    917 Arbutus Rd, Annapolis, MD 21403
  • /106

    $3,250,000

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

    1486 Downham Market, Annapolis, MD 21401

    Prepare to be captivated by 1486 Downham Market, a striking architectural masterpiece perched on one of the most coveted deep-water lots in Annapolis. Perfectly situated at the mouth of Clements Creek—widely regarded as one of the safest and most protected hurricane holes on the Severn—this estate delivers a rare blend of natural beauty, luxury, and marine excellence. With a commanding 180-foot

    Wendy Oliver Coldwell Banker Realty

    1486 Downham Market, Annapolis, MD 21401
  • /40

    $3,700,000

    • 5 Beds
    • 6 Baths
    • 6,094 Sq Ft

    917 Childs Point Rd, Annapolis, MD 21401

    This stunning waterfront retreat offers privacy, breathtaking views of Crab Creek and the South River, and a waterside pool. The newly extended pier can accommodate a 50' sailboat. South-facing exposure and walls of windows let in tons of natural light and the sunlight sparkles off the serene waters at the shoreline. The beautiful renovation by Gate One Builders and new hardwood flooring created

    Brad Kappel TTR Sotheby's International Realty

    917 Childs Point Rd, Annapolis, MD 21401
  • /85

    $5,950,000

    • 4 Beds
    • 7 Baths
    • 7,684 Sq Ft

    1864 Milvale Rd, Annapolis, MD 21409

    A Rare Opportunity on Milvale Road and Mill Creek.This exceptional waterfront property, crafted by renowned builder Lynbrook Homes and thoughtfully designed by architect Vince Green, offers a rare blend of luxury and serenity. The open-concept floor plan is designed to maximize the sweeping, panoramic views of Mill Creek, with western exposure providing breathtaking sunsets

    Glenn Sutton TTR Sotheby's International Realty

    1864 Milvale Rd, Annapolis, MD 21409
  • /126

    $4,450,000

    • 6 Beds
    • 9 Baths
    • 12,374 Sq Ft

    840 Childs Point Rd, Annapolis, MD 21401

    One-of-a-kind Waterfront Luxury in Annapolis, Maryland! Secluded on 2.59 lush, park-like acres along the shores of one of the Chesapeake Bay’s most serene and protected tributaries, this exceptional estate offers an unparalleled blend of privacy, elegance, and premier waterfront living rarely found in Annapolis. From the moment you arrive down the tree-lined drive, a sense of calm and

    David Orso Berkshire Hathaway HomeServices PenFed Realty

    840 Childs Point Rd, Annapolis, MD 21401
  • /67

    $2,695,000

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

    2680 Claibourne Ct, Annapolis, MD 21403

    Nestled on Chase Pond along the serene shores of the Chesapeake Bay, 2680 Claibourne Court offers an unparalleled waterfront living experience. This meticulously renovated coastal contemporary-style residence boasts 5 bedrooms, 4 full bathrooms, and seamlessly blends luxury with comfort. Set on a generous 2.62-acre waterfront lot, the property features a private pier with boat lifts and a beach,

    Doc Keane Washington Fine Properties, LLC

    2680 Claibourne Ct, Annapolis, MD 21403
  • /128

    $3,100,000

    • 5 Beds
    • 4.5 Baths
    • 6,412 Sq Ft

    856 St Edmonds Place, Annapolis, MD 21401

    Welcome to 856 St Edmonds Place! Have it all with stunning views from nearly every room, deep water, privacy, and a spacious floorplan for multi generational living! Spectacular custom built waterfront home in the sought after Downs community of Annapolis! Breathtaking views await you from every corner of this updated and well conceived home. Dramatic details throughout highlight the open

    James Schaecher Keller Williams Flagship

    856 St Edmonds Place, Annapolis, MD 21401
  • /44

    $2,245,000

    • 3 Beds
    • 2.5 Baths
    • 3,243 Sq Ft

    2908 Southwater Point Dr, Annapolis, MD 21401

    Fabulous waterfront "Deck Home" with heated saltwater pool and unprecedented views across Broad Creek out to the South River. This special residence located in the Southwater Point enclave of waterfront homes offers the perfect elevation to oversee the stunning sunset and water views. The layout of the home is perfectly designed to enjoy the ever changing scenery from almost every room in the

    Brad Kappel TTR Sotheby's International Realty

    2908 Southwater Point Dr, Annapolis, MD 21401
  • /33

    $2,350,000 New Construction

    • 4 Beds
    • 4.5 Baths
    • 3,803 Sq Ft

    1634 P 269 Orchard Beach Rd, Annapolis, MD 21409

    **TEAR DOWN/NEW BUILD PACKAGE** The homesite sits on an elevated 3 acres offering expansive views of Mill Creek and is surrounded by mature trees for a serene, private setting. Take advantage of water views without the cost of waterfront taxes! Three marinas are just minutes from your doorstep, making this an ideal location for boating enthusiasts. The proposed Luxury Wye Mills model features an

    Rachel Best RE/MAX Leading Edge

    1634 P 269 Orchard Beach Rd, Annapolis, MD 21409
  • /46

    $1,299,999

    • 5 Beds
    • 4 Baths
    • 2,700 Sq Ft

    767 Bon Haven Dr, Annapolis, MD 21401

    Discover luxurious living in this exceptional 4-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
  • /73

    $945,000

    • 4 Beds
    • 3 Baths
    • 4,592 Sq Ft

    2020 John Hanson Overlook, Annapolis, MD 21401

    Welcome home to this gorgeous 4-bedroom, 3-bath home in the sought-after North River Forest neighborhood. Situated on over an acre, this property features a bright, open floor plan with two first-floor bedrooms and a full bath, plus a spacious family room with soaring ceilings, skylights, and beautiful hardwood floors.The eat-in chef’s kitchen is a dream—complete with a gas cooktop,

    Barry Weller Barry Weller Properties, LLC

    2020 John Hanson Overlook, Annapolis, MD 21401
  • /63

    $1,670,000

    • 3 Beds
    • 2.5 Baths
    • 3,106 Sq Ft

    2908 Southwater Point Dr, Annapolis, MD 21401

    Welcome to your South River waterfront dream home! This stunning contemporary offers over 3,000 square feet of beautifully designed living space, featuring 3 bedrooms, 2.5 bathrooms, hardwood floors, neutral tones, and high-end finishes throughout. Greeted by an abundance of natural light and sweeping river views, the open-concept living area features an electric fireplace and flows seamlessly

    David Orso Berkshire Hathaway HomeServices PenFed Realty

    2908 Southwater Point Dr, Annapolis, MD 21401
  • /74

    $1,295,000 Open Fri 5PM - 7PM

    • 4 Beds
    • 3.5 Baths
    • 3,480 Sq Ft

    1580 Keswick Place, Annapolis, MD 21401

    ** Price Improvement! **Welcome to this exceptional residence in the highly coveted Downs on the Severn community, known for its premier amenities and serene setting. Enjoy access to the newly renovated marina with floating dock, kayak storage, boat launch, community clubhouse and pool, tennis courts, tot lots, walking trails, and more! The gourmet kitchen features granite countertops,

    Bob Chew Samson Properties

    1580 Keswick Place, Annapolis, MD 21401
  • /54

    $930,000

    • 3 Beds
    • 3 Baths
    • 2,868 Sq Ft

    1634 Orchard Beach Rd, Annapolis, MD 21409

    An incredible opportunity with endless potential awaits! This 3-bedroom, 3-bath home sits on an elevated 3 acres, offering expansive views of Mill Creek and is surrounded by mature trees for a serene, private setting. Whether you're looking to enjoy the existing solidly built home, renovate, or expand - this property provides the space and flexibility to create your dream retreat. Take advantage

    Rachel Best RE/MAX Leading Edge

    1634 Orchard Beach 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
  • /50

    $8,995,000

    • 7 Beds
    • 9 Baths
    • 12,200 Sq Ft

    1900 Carrollton Rd, Annapolis, MD 21409

    Rare opportunity for a true legacy property on the Severn River! Built by Pilli Custom Homes, this home is a masterpiece of craftsmanship. Wake up every morning to the everchanging scenery out your windows, step out onto your private balcony with a freshly brewed coffee from your in-room coffee bar, feeling the gentle river breeze as you watch sailboats drift by. Make your way down via the

    Brad Kappel TTR Sotheby's International Realty

    1900 Carrollton Rd, Annapolis, MD 21409
  • /35

    $3,800,000

    • 5 Beds
    • 3 Baths
    • 2,775 Sq Ft

    1741 Holly Beach Farm Rd, Annapolis, MD 21409

    Rare Waterfront Opportunity! Escape to your waterfront farmhouse retreat. Nestled on 3.5 picturesque acres overlooking the tranquil waters of protected Moss Pond, this charming historic property offers big views of and direct access to the Chesapeake Bay. Originally part of a working thoroughbred racehorse farm, this home is surrounded by parkland and privacy while still close to the city.

    David Orso Berkshire Hathaway HomeServices PenFed Realty

    1741 Holly Beach Farm Rd, Annapolis, MD 21409
  • /68

    $3,475,000

    • 6 Beds
    • 5.5 Baths
    • 6,732 Sq Ft

    1576 Bay Head Rd, Annapolis, MD 21409

    Boating season is here! Incredible opportunity - Seller will hold a 10% second mortgage at 5.87% for five years if you are putting a minimum of 20% down! Welcome to 1576 Bay Head Road, an exceptional waterfront estate where luxury living meets the ultimate Chesapeake Bay lifestyle. Perfectly situated on a private one-acre lot along the calm, protected waters of the Little Magothy River, this

    Wendy Oliver Coldwell Banker Realty

    1576 Bay Head Rd, Annapolis, MD 21409
  • /112

    $6,750,000

    • 6 Beds
    • 8.5 Baths
    • 11,045 Sq Ft

    803 Coachway, Annapolis, MD 21401

    This Severn River Waterfront Estate is a rare and breathtaking Annapolis retreat. Experience the ultimate in waterfront living in this exquisite residence, a true masterpiece offering unparalleled panoramic water views. Nestled on a pristine one-acre site in the prestigious Point of The Downs, this custom-built legacy home has been meticulously updated to perfection, creating the ideal setting

    Georgie Berkinshaw Coldwell Banker Realty

    803 Coachway, Annapolis, MD 21401
  • /41

    $6,498,000

    • 5 Beds
    • 5.5 Baths
    • 6,911 Sq Ft

    205 Winchester Beach Dr, Annapolis, MD 21409

    Winchester-on-the-Severn Waterfront! This modern home is only surpassed by the all encompassing, elevated views of the Severn River. Exquisite finishes are the hallmark of this elegant 5 bedroom 5.5 bath brick home where no details were compromised in presenting a home of distinction. Floor to ceiling sliding LaCantina glass doors blur the line of indoor and outdoor living and showcase the

    Brad Kappel TTR Sotheby's International Realty

    205 Winchester Beach Dr, Annapolis, MD 21409
  • /49

    $19,995,000

    • 7 Beds
    • 13 Baths
    • 35,435 Sq Ft

    1604 Winchester Rd, Annapolis, MD 21409

    THE FRIARY a Trophy property in a league of its own! Set on 23 private acres overlooking a gracious bend of the Severn River with 1,500ft of prime waterfrontage, just minutes from downtown Annapolis and less than an hour from the nation's capital, lies one of the most distinctive estates offered for sale on the East Coast. A true architectural masterpiece, this exquisite 35,000+ sqft

    Brad Kappel TTR Sotheby's International Realty

    1604 Winchester Rd, Annapolis, MD 21409
  • /72

    $1,379,000

    • 3 Beds
    • 2 Baths
    • 1,809 Sq Ft

    2762 Bon Haven Ln, Annapolis, MD 21401

    Welcome to this waterfront ranch home in the highly sought-after community of Bon Haven, situated on over an acre of serene land along the beautiful South River. This renovated gem, complete with a new private pier and boat access, offers an idyllic lifestyle for water enthusiasts and nature lovers alike. This property is back on the market due to financing falling through for the

    Donna Baldino Keller Williams Select Realtors of Annapolis

    2762 Bon Haven Ln, Annapolis, MD 21401
  • /34

    $1,325,000

    • 6 Beds
    • 4.5 Baths
    • 6,196 Sq Ft

    1707 Ritchie Hwy, Annapolis, MD 21409

    Back on the Market!Escape to your own private Estate. 6100+ sqf of finished space with 2.2 acres of land in the most desirable location of Annapolis. 6 Bedrooms, 4.5 Bathrooms, with > 1000sqf for Master Suite. Two Fireplaces. Move-in condition. Potential for subdivision (check with engineer/county). A stone's throw to downtown without the city taxes. Across from B&A bike

    Mary Saba Keller Williams Select Realtors of Annapolis

    1707 Ritchie Hwy, Annapolis, MD 21409
  • /7

    $749,900

    • Land
    • 1.49 Acres
    • $503,289 per Acre

    1444 Whitehall Rd, Annapolis, MD 21409

    1.485 acre RLD zoned parcel/ lot available adjacent to McDonald's, Wendy's. Potential uses include daycare, veterinarian, assisted living, club, group home, kennel, plant nursery, produce stand, etc. All utilities are available. Easy access on and off of Rt. 50. Refer to documents section.

    Timothy Hogan Hogan Companies Residential

    1444 Whitehall Rd, Annapolis, MD 21409
  • /2

    $575,000

    • Land
    • 8 Acres
    • $71,875 per Acre

    0 Bay Head Rd, Annapolis, MD 21409

    Build your dream home using your builder or ours! This is truly an amazing 6.7 acre (+/- NOTE THE TAX RECORD IS WRONG) estate-home lot in a beautiful part of the County. The shared portion of the driveway (which connects to the 9+ acre lot behind it) is cleared. Perc is approved. File your grading and building permits and get going!

    Scott Saunders Coldwell Banker Waterman Realty

    0 Bay Head Rd, Annapolis, MD 21409
  • /73

    $1,950,000 New Construction

    • 6 Beds
    • 5.5 Baths
    • 5,636 Sq Ft

    934 Chesterfield Rd, Annapolis, MD 21401

    The One That Outshines Them All—Near Downtown AnnapolisThis stunning newly built colonial home is a true showcase of thoughtful design and refined craftsmanship, beautifully situated on 1.34 acres with no association fees to limit your lifestyle. From the rich French white oak flooring and custom stair railings to the intricate glass doorknobs and solid wood doors, every detail has been

    Bryan D. Gamble Gamble Realty, Inc

    934 Chesterfield Rd, Annapolis, MD 21401
  • /30

    $4,950,000 New Construction

    • 5 Beds
    • 4.5 Baths
    • 5,000 Sq Ft

    1632 Winchester Rd, Annapolis, MD 21409

    Don't miss this incredible opportunity to build your dream luxury estate home on this amazing private 3.3 acre homesite with amazing waterviews and privacy. Tucked away back off of your 1/4 mile private driveway which sets the tone as you approach your very own oasis. Come witness our vision and be a part of creating a generational estate that Annapolis rarely sees. The main level boasts

    Colleen Smith EXP Realty, LLC

    1632 Winchester Rd, Annapolis, MD 21409
  • /57

    $800,000 Open House 9/06

    • 5 Beds
    • 4.5 Baths
    • 4,084 Sq Ft

    1583 Keswick Place, Annapolis, MD 21401

    Property is being offered at Public Auction by Witman Auctioneers, Inc. to settle an Estate. List Price of $800,000 is opening bid-Estate of Geoffrey J. Dive - ONLINE PUBLIC REAL ESTATE AUCTIONLOCATION: 1583 Keswick Place “The Downs”, Annapolis, MD 21401Severn Downs Community- Anne Arundel County(The Downs – Lot 187 Sc 12) Thursday, September 18, 2025Real Estate 6:00 PM ***

    Zachary Shelley Streett Hopkins Real Estate, LLC

    1583 Keswick Place, Annapolis, MD 21401

Home Trends in Annapolis, MD

Housing Trends

Median Sale Price
$550,000
Median Single Family Sale Price
$1,033,403
Median Townhouse Sale Price
$574,500
Median 2 Bedroom Sale Price
$470,000
Median 1 Bedroom Sale Price
$489,900
Average Price Per Sq Ft
$382
Number of Homes for Sale
39
Last 12 months Home Sales
326
Months of Supply
1.40
Median List Price
$600,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-3%
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