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Chester, MD Homes for Sale with Acreage

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  • 2855 Cox Neck Rd, Chester, MD 21619
    2855 Cox Neck Rd, Chester, MD 21619
    2855 Cox Neck Rd, Chester, MD 21619
    /78

    $1,195,000

    $55K PRICE DROP
    • 4 Beds
    • 4.5 Baths
    • 4,413 Sq Ft

    2855 Cox Neck Rd, Chester, MD 21619

    Located in the prestigious Southwind community, a penisula between Crab Alley Bay & Cox Creek, this elegant contemporary ranch-style home offers an unparalleled lifestyle of luxury and comfort. Spanning over 4,400 sq. ft. of finished space, the interior boasts elegant marble flooring, complemented by crown moldings and built-ins that enhance its sophisticated charm. The gourmet kitchen, featuring

    Tricia Wilson Wilson Realty & Staging LLC

    2855 Cox Neck Rd, Chester, MD 21619
  • 300 Woods Point Rd, Chester, MD 21619
    300 Woods Point Rd, Chester, MD 21619
    300 Woods Point Rd, Chester, MD 21619
    /17

    $2,840,000

    Open Thu 6PM - 8:30PM Coming Soon
    • 3 Beds
    • 2 Baths
    • 1,704 Sq Ft

    300 Woods Point Rd, Chester, MD 21619

    Privacy without isolation. This property will change your mind it you think you need 10 or 20 acres to have wide open spaces and not have neighbors breathing down your neck! Two separate living quarters, each with unobstructed views and up to date amenities. Discover a captivating blend of traditional charm and vintage cape cod in the primary 3-bedroom, 2-bathroom residence, recently updated in

    Elinor Warring Tidewater Properties

    300 Woods Point Rd, Chester, MD 21619
  • 330 Serenity Ln, Chester, MD 21619
    330 Serenity Ln, Chester, MD 21619
    330 Serenity Ln, Chester, MD 21619
    /50

    $5,900,000

    • 7 Beds
    • 9 Baths
    • 9,974 Sq Ft

    330 Serenity Ln, Chester, MD 21619

    Designed to rival a private resort, the outdoor spaces were made for celebrating with family and friends. Sweeping water views set the stage for unforgettable gatherings. The waterfront pool features a cascading natural rock waterfall with a bench tucked underneath and a generous shallow sun shelf. A beautifully appointed pool house offers a covered summer kitchen, bar, seating area and full bath

    Brad Kappel TTR Sotheby's International Realty

    330 Serenity Ln, Chester, MD 21619
  • 2513 Cecil Dr, Chester, MD 21619
    2513 Cecil Dr, Chester, MD 21619
    2513 Cecil Dr, Chester, MD 21619
    /60

    $1,350,000

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

    2513 Cecil Dr, Chester, MD 21619

    The locals called it Keister's Folly. In the mid-1940s, Dr. Keister built a barn on Kent Island overlooking Cox Creek, hoping to raise Black Angus cattle on 25 acres. The acreage was too small for the endeavor — but the barn he built was extraordinary. In the early 1960s, the developer of the Harbor View community converted it into a residence. The current owners' family purchased it in 1965 and

    David Moore Real Broker, LLC

    2513 Cecil Dr, Chester, MD 21619
  • 315 Bentons Pleasure Rd, Chester, MD 21619
    315 Bentons Pleasure Rd, Chester, MD 21619
    /2

    $629,900

    Coming Soon
    • 3 Beds
    • 2 Baths
    • 1,688 Sq Ft

    315 Bentons Pleasure Rd, Chester, MD 21619

    9999

    Douglas Kayhoe Douglas Realty LLC

    315 Bentons Pleasure Rd, Chester, MD 21619
  • 114 Cedar Rd, Chester, MD 21619
    114 Cedar Rd, Chester, MD 21619
    114 Cedar Rd, Chester, MD 21619
    /97

    $375,000

    Open Sat 4PM - 6PM
    • 3 Beds
    • 2 Baths
    • 3,128 Sq Ft

    114 Cedar Rd, Chester, MD 21619

    AGENTS - PLEASE VIEW AGENT REMARKS IN BRIGHT MLS. Discover your private sanctuary on this sprawling 1-acre lot. This meticulously maintained residence with over 3,000 SF of total living space blends modern comfort with rare functional space. Inside, you’ll find fresh updates and an expanded, bespoke master suite designed for total relaxation. The true highlight is the property’s versatility:

    Tom Atwood Keller Williams Legacy

    114 Cedar Rd, Chester, MD 21619
Maryland Queen Anne's County Chester

Homes for Sale with Acreage in Chester, MD

Home Prices in Chester, MD

The median home sale price in Chester, MD is $665,000, up 17% year-over-year. Homes in Chester sell in 306 days on average, compared to the national average of 57 days.

Home Price Trends

Median Sale Price
$665,000
Median Single Family Sale Price
$709,900
Median Townhouse Sale Price
$365,000
Median 2 Bedroom Sale Price
$606,250
Median 1 Bedroom Sale Price
$284,500
Average Price Per Sq Ft
$305
Number of Homes for Sale
91
Last 12 months Home Sales
225
Months of Supply
4.90
Median List Price
$682,450
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
17%
How to Buy a Home How to Finance a Home How to Sell a Home

In Chester, there are currently 6 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 Chester, MD offer the flexibility to tailor your living experience to your preferences. Browse the selection of homes for sale with land in Chester and discover the potential and freedom that comes with owning your own piece of property.

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