26

Annapolis, MD Homes for Sale with Acreage

Section Image Section Image
  • 15 E Nap Ln, Annapolis, MD 21409
    15 E Nap Ln, Annapolis, MD 21409
    15 E Nap Ln, Annapolis, MD 21409
    /13

    $1,100,000

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

    15 E Nap Ln, Annapolis, MD 21409

    Price Reduction: Motivated Seller BRING ALL OFFERS! 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

    Agent Photo

    Litra Simms

    Simms and Associates

    (443) 339-8629

    15 E Nap Ln, Annapolis, MD 21409
  • 3054 Rundelac Rd, Annapolis, MD 21403
    3054 Rundelac Rd, Annapolis, MD 21403
    3054 Rundelac Rd, Annapolis, MD 21403
    /49

    $4,350,000

    • 8 Beds
    • 9 Baths
    • 13,495 Sq Ft

    3054 Rundelac Rd, Annapolis, MD 21403

    Welcome to 3054 Rundelac Road, an extraordinary property offering the ultimate experience in waterfront luxury. Nestled on nearly four private acres on Aberdeen Creek, this estate is a timeless beauty, showcasing thoughtful design and exceptional amenities. The residence, spanning over 13,495 square feet with 7 bedrooms and 9 bathrooms, is a showcase of exquisite craftsmanship, featuring recent,

    Gail Chisholm Compass

    3054 Rundelac Rd, Annapolis, MD 21403
  • 1576 Bay Head Rd, Annapolis, MD 21409
    1576 Bay Head Rd, Annapolis, MD 21409
    1576 Bay Head Rd, Annapolis, MD 21409
    /67

    $3,325,000

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

    1576 Bay Head Rd, Annapolis, MD 21409

    Welcome to 1576 Bay Head Road, a breathtaking custom-built waterfront estate on the peaceful Little Magothy River offering over an acre of privacy, 6,700 square feet of refined luxury, and direct access to the Chesapeake Bay in under five minutes. Built in 2017 and designed for modern living, this residence perfectly balances year-round comfort, elegance, and effortless waterfront enjoyment.

    Wendy Oliver Coldwell Banker Realty

    1576 Bay Head Rd, Annapolis, MD 21409
  • 1715 Porters Hill Rd, Annapolis, MD 21401
    1715 Porters Hill Rd, Annapolis, MD 21401
    1715 Porters Hill Rd, Annapolis, MD 21401
    /53

    $3,995,000

    • 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

    Reid Buckley Long & Foster Real Estate, Inc.

    1715 Porters Hill Rd, Annapolis, MD 21401
  • 812 Coachway, Annapolis, MD 21401
    812 Coachway, Annapolis, MD 21401
    812 Coachway, Annapolis, MD 21401
    /63

    $3,499,999

    • 6 Beds
    • 7 Baths
    • 7,766 Sq Ft

    812 Coachway, Annapolis, MD 21401

    Wake up to Severn River views, not dock maintenance! 812 Coachway is an all-brick waterfront estate in The Downs on the Severn, offering 6 bedrooms, 7 baths, and over 7,500 square feet of refined indoor-outdoor living. Thoughtfully updated to merge timeless architecture with modern luxury, nearly every room frames stunning Severn River views. A two-story foyer leads to the office with custom

    Keisha McClain Hubble Bisbee Christie's International Real Estate

    812 Coachway, Annapolis, MD 21401
  • 778 Bon Haven Dr, Annapolis, MD 21401
    778 Bon Haven Dr, Annapolis, MD 21401
    778 Bon Haven Dr, Annapolis, MD 21401
    /95

    $2,800,000

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

    778 Bon Haven Dr, Annapolis, MD 21401

    Exquisite South River Waterfront Estate Experience waterfront living at its finest in this rare South River estate situated at the end of a quiet cul-de-sac. Elevated above the water on a private 1.07-acre lot with 132 feet of premier frontage, this stunningly remodeled 4,900+ sq. ft. rancher offers timeless elegance, modern sophistication, and panoramic river views from nearly every room. The

    Steven Knopf Engel & Völkers Annapolis

    778 Bon Haven Dr, Annapolis, MD 21401
  • 1486 Downham Market, Annapolis, MD 21401
    1486 Downham Market, Annapolis, MD 21401
    1486 Downham Market, Annapolis, MD 21401
    /106

    $3,250,000

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

    1486 Downham Market, Annapolis, MD 21401

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

    Wendy Oliver Coldwell Banker Realty

    1486 Downham Market, Annapolis, MD 21401
  • 343 Dubois Rd, Annapolis, MD 21401
    343 Dubois Rd, Annapolis, MD 21401
    343 Dubois Rd, Annapolis, MD 21401
    /50

    $1,999,000 New Construction

    • 4 Beds
    • 3.5 Baths
    • 3,716 Sq Ft

    343 Dubois Rd, Annapolis, MD 21401

    TO-BE-BUILT. Construction has not started. Photos are of a previously built home by Builder. Choose your options and finishes. Sales includes 2 parcels 341 & 343 Dubois Rd. Located in picturesque Annapolis, MD this one-of-a-kind property will sit on a 1.3 acre double lot and will feature a main level owner's suite and high end finishes throughout. Optional features include a gourmet kitchen with

    Adam Ellison Long & Foster Real Estate, Inc.

    343 Dubois Rd, Annapolis, MD 21401
  • 621 Wood Lot Trail Rd, Annapolis, MD 21401
    621 Wood Lot Trail Rd, Annapolis, MD 21401
    621 Wood Lot Trail Rd, Annapolis, MD 21401
    /44

    $894,900

    • 5 Beds
    • 3.5 Baths
    • 3,970 Sq Ft

    621 Wood Lot Trail Rd, Annapolis, MD 21401

    This is the one you've been waiting for! First open house scheduled for Sunday, November 23, 2025 from 2-4pm. Come visit this well maintained, 5 bedroom, 3 and 1/2 bath gorgeous home located on 1.43 acres in the sought after community of The Ridges! This lovely home is situated in a wooded wonderland while still being close to all that Annapolis has to offer! As you enter, you'll immediately note

    Kathryn Sullivan RE/MAX Distinctive Real Estate, Inc.

    621 Wood Lot Trail Rd, Annapolis, MD 21401
  • 2203 Mulberry Hill Rd, Annapolis, MD 21409
    2203 Mulberry Hill Rd, Annapolis, MD 21409
    2203 Mulberry Hill Rd, Annapolis, MD 21409
    /19

    $1,350,000

    • 3 Beds
    • 2.5 Baths
    • 1,994 Sq Ft

    2203 Mulberry Hill Rd, Annapolis, MD 21409

    Bring your personal touch to this waterfront get away and enjoy the waterfront lifestyle! Waterfront Suisse Chalet on Mill Creek – Annapolis, MD Experience the perfect blend of charm, comfort, and waterfront living in this spacious 3-bedroom, 2.5-bath Suisse Chalet nestled on scenic Mill Creek, just off the Chesapeake Bay and Severn River. Located on Mulberry Hill Road in Annapolis, this

    Tommy Eicher Coldwell Banker Realty

    2203 Mulberry Hill Rd, Annapolis, MD 21409
  • 1635 N Winchester Rd, Annapolis, MD 21409
    1635 N Winchester Rd, Annapolis, MD 21409
    1635 N Winchester Rd, Annapolis, MD 21409
    /71

    $1,247,900

    • 5 Beds
    • 4 Baths
    • 3,660 Sq Ft

    1635 N Winchester Rd, Annapolis, MD 21409

    A Rare Exceptional Retreat in Winchester Estates — Annapolis, MDWelcome to an extraordinary custom-built residence where timeless elegance meets unparalleled serenity. Set on a magnificently landscaped, park-like acre, this 5-bedroom, 4-bath estate offers a level of privacy and tranquility seldom found so close to the heart of downtown Annapolis. Nestled within the prestigious Winchester

    Ana Lopez Equity Property Investments

    1635 N Winchester 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

    $8,750,000

    • 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
  • 1814 Pleasant Plains Rd, Annapolis, MD 21409
    1814 Pleasant Plains Rd, Annapolis, MD 21409
    1814 Pleasant Plains Rd, Annapolis, MD 21409
    /82

    $1,300,000

    • 5 Beds
    • 2 Baths
    • 1,919 Sq Ft

    1814 Pleasant Plains Rd, Annapolis, MD 21409

    RANCHER & DETACHED APARTMENT DWELLING on 3.92 WOODED ACRES WITH ACCESS 15' RIGHT OF WAY TO SCENIC BURLEY CREEK! PRIVACY & SERENITY mere minutes from Downtown City Dock Harbor and the Bay! Pier with 15’ right of way from Burley Lane to a 35' wide fee simple area along Burley Creek and Chesapeake boating access via Whitehall Bay. Sprawling stone Rancher boasting organic hardwoods, abundant windows

    Karlton Morris Long & Foster Real Estate, Inc.

    1814 Pleasant Plains Rd, Annapolis, MD 21409
  • 1814 & 1836 Pleasant Plains & Cherry Rd, Annapolis, MD 21409
    1814 & 1836 Pleasant Plains & Cherry Rd, Annapolis, MD 21409
    1814 & 1836 Pleasant Plains & Cherry Rd, Annapolis, MD 21409
    /82

    $1,300,000

    • 5 Beds
    • 2 Baths
    • 1,919 Sq Ft

    1814 & 1836 Pleasant Plains & Cherry Rd, Annapolis, MD 21409

    RANCHER & DETACHED APARTMENT DWELLING on 3.92 WOODED ACRES WITH ACCESS 15' RIGHT OF WAY TO SCENIC BURLEY CREEK! PRIVACY & SERENITY mere minutes from Downtown City Dock Harbor and the Bay! Pier with 15’ right of way from Burley Lane to a 35' wide fee simple area along Burley Creek water frontage and Chesapeake boating access via Whitehall Bay. Sprawling stone Rancher boasting organic hardwoods,

    Karlton Morris Long & Foster Real Estate, Inc.

    1814 & 1836 Pleasant Plains & Cherry Rd, Annapolis, MD 21409
  • 1836 Cherry Rd, Annapolis, MD 21409
    1836 Cherry Rd, Annapolis, MD 21409
    1836 Cherry Rd, Annapolis, MD 21409
    /82

    $1,300,000

    • Land
    • 3.92 Acres
    • $331,633 per Acre

    1836 Cherry Rd, Annapolis, MD 21409

    RANCHER & DETACHED APARTMENT DWELLING on 3.92 WOODED ACRES WITH ACCESS 15' RIGHT OF WAY TO SCENIC BURLEY CREEK! PRIVACY & SERENITY mere minutes from Downtown City Dock Harbor and the Bay! Pier with 15 right of way from Burley Lane to a 35' wide fee simple area along Burley Creek and Chesapeake boating access via Whitehall Bay. Sprawling stone Rancher boasting organic hardwoods, abundant windows

    Karlton Morris Long & Foster Real Estate, Inc.

    1836 Cherry Rd, Annapolis, MD 21409
  • 767 Bon Haven Dr, Annapolis, MD 21401
    767 Bon Haven Dr, Annapolis, MD 21401
    767 Bon Haven Dr, Annapolis, MD 21401
    /50

    $1,195,000

    • 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
  • 1900 Carrollton Rd, Annapolis, MD 21409
    1900 Carrollton Rd, Annapolis, MD 21409
    1900 Carrollton 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
  • 856 St Edmonds Place, Annapolis, MD 21401
    856 St Edmonds Place, Annapolis, MD 21401
    856 St Edmonds Place, Annapolis, MD 21401
    /129

    $3,100,000

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

    856 St Edmonds Place, Annapolis, MD 21401

    **Open house Saturday, Nov 22, 11-1 pm** 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

    James Schaecher Keller Williams Flagship

    856 St Edmonds Place, Annapolis, MD 21401
  • 2762 Bon Haven Ln, Annapolis, MD 21401
    2762 Bon Haven Ln, Annapolis, MD 21401
    2762 Bon Haven Ln, Annapolis, MD 21401
    /73

    $1,199,000

    • 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 buyer! As you

    Donna Baldino Keller Williams Select Realtors of Annapolis

    2762 Bon Haven Ln, Annapolis, MD 21401
  • 1444 Whitehall Rd, Annapolis, MD 21409
    1444 Whitehall Rd, Annapolis, MD 21409
    1444 Whitehall Rd, Annapolis, MD 21409
    /7

    $739,900

    • Land
    • 1.49 Acres
    • $496,577 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
  • 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
  • 1907 Mackiebeth Ct, Annapolis, MD 21401
    1907 Mackiebeth Ct, Annapolis, MD 21401
    1907 Mackiebeth Ct, Annapolis, MD 21401
    /6

    $1,575,000 New Construction

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

    1907 Mackiebeth Ct, Annapolis, MD 21401

    PHOTOS TO BE UPDATED THROUGHOUT BUILDING PROCESS!! 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 set to be completed by year end, 2025. With a stunning Colonial architectural style, this beautiful home offers 5-bedrooms and

    Marilyn Hendley EXP Realty, LLC

    1907 Mackiebeth Ct, Annapolis, MD 21401
  • 3182 Harness Creek Rd, Annapolis, MD 21403
    3182 Harness Creek Rd, Annapolis, MD 21403
    3182 Harness Creek Rd, Annapolis, MD 21403
    /129

    $10,250,000 New Construction

    • 4 Beds
    • 5.5 Baths
    • 5,375 Sq Ft

    3182 Harness Creek Rd, Annapolis, MD 21403

    Incredible value for this newly completed waterfront estate — now offered at $10,250,000. This brand-new, never-lived-in residence offers an exceptional opportunity to own a luxury home on 1.04 acres along the protected waters of Aberdeen Creek, just ten minutes from Annapolis City Dock.Designed by Hammond Wilson Architects and built by award-winning Pyramid Builders, the home was created to

    Georgie Berkinshaw Coldwell Banker Realty

    3182 Harness Creek Rd, Annapolis, MD 21403
  • 934 Chesterfield Rd, Annapolis, MD 21401
    934 Chesterfield Rd, Annapolis, MD 21401
    934 Chesterfield Rd, Annapolis, MD 21401
    /73

    $1,895,000 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
  • 1632 Winchester Rd, Annapolis, MD 21409
    1632 Winchester Rd, Annapolis, MD 21409
    1632 Winchester Rd, Annapolis, MD 21409
    /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
  • 2638 Greenbriar Ln, Annapolis, MD 21401
    2638 Greenbriar Ln, Annapolis, MD 21401
    /2

    $350,000

    • 4 Beds
    • 2 Baths
    • 2,606 Sq Ft

    2638 Greenbriar Ln, Annapolis, MD 21401

    REAL ESTATE AUCTION featuring ON SITE and SIMULCAST ONLINE BIDDING!! Online Bidding Opens - Thursday, November 20, 2025. Live On Site Auction - Friday, November 21, 2025 at 12:00 noon. List price is opening bid only. Partition related sale of a sprawling ranch home needing renovation in a well demanded area of Annapolis. The home is conveniently located close to Forest Drive, groceries, shopping,

    Charles Billig A.J. Billig & Company

    2638 Greenbriar Ln, Annapolis, MD 21401
Maryland Anne Arundel County Annapolis

Homes for Sale with Acreage in Annapolis, MD

Home Trends in Annapolis, MD

On average, homes in Annapolis, MD sell after 33 days on the market compared to the national average of 53 days. The median sale price for homes in Annapolis, MD over the last 12 months is $619,900, up 3% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$619,900
Median Single Family Sale Price
$799,995
Median Townhouse Sale Price
$442,500
Median 2 Bedroom Sale Price
$410,000
Median 1 Bedroom Sale Price
$453,700
Average Price Per Sq Ft
$355
Number of Homes for Sale
240
Last 12 months Home Sales
1,271
Months of Supply
2.30
Median List Price
$629,949
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
3%

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

In Annapolis, there are currently 26 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.

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 © 2025 CoStar Group