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Windsor, VA Homes for Sale with Acreage

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  • 8368 Whispering Pines Trail, Windsor, VA 23487
    8368 Whispering Pines Trail, Windsor, VA 23487
    8368 Whispering Pines Trail, Windsor, VA 23487
    /48

    $400,000

    $75K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,208 Sq Ft

    8368 Whispering Pines Trail, Windsor, VA 23487

    Welcome to Whispering Pines Trail, a rare opportunity to own a beautifully updated home on 4.46 private acres in Windsor. This 3-bedroom, 2-bath home offers 2,208 square feet of move-in ready living space with a fully updated kitchen, renovated primary bath, new flooring, paint, and trim throughout. The spacious upstairs family room is wired for surround sound and projector, with the screen

    Agent Photo

    Leslie Brennan

    Aweigh Real Estate

    8368 Whispering Pines Trail, Windsor, VA 23487
  • Lot 3 Joyners Bridge Rd, Windsor, VA 23487
    Lot 3 Joyners Bridge Rd, Windsor, VA 23487
    Lot 3 Joyners Bridge Rd, Windsor, VA 23487
    /30

    $1,150,000

    New Construction
    • 3 Beds
    • 3 Baths
    • 2,430 Sq Ft

    Lot 3 Joyners Bridge Rd, Windsor, VA 23487

    Welcome to approximately 12 acres on Joyners Bridge Road in Windsor, Virginia, offering the perfect blend of a quiet rural setting while remaining conveniently located to everyday amenities. The Town of Windsor provides local shopping, services, schools, parks, and community conveniences, while nearby Suffolk offers additional shopping, dining, entertainment, and services. The property provides

    Agent Photo

    Brian Simon

    Fit Realty

    Lot 3 Joyners Bridge Rd, Windsor, VA 23487
  • 12 Ac Tar Rd, Windsor, VA 23487
    12 Ac Tar Rd, Windsor, VA 23487
    12 Ac Tar Rd, Windsor, VA 23487
    /4

    $268,000

    • Land
    • 12.26 Acres
    • $21,860 per Acre

    12 Ac Tar Rd, Windsor, VA 23487

    Wonderful Opportunity in Isle of Wight County! This Property Consists Primarily of Cropland, with Some Wooded Acreage Along the Southern Portion of the Property. The Property Offers Approximately 1,073.68 Feet of Road Frontage Along Tar Road and Approximately 523.78 Feet Along Pope Swamp Trail, This Property Provides Excellent Access and Potential for a Variety of Uses.

    Durwood Scott Scott & Assoc. Inc. Realtors

    12 Ac Tar Rd, Windsor, VA 23487
  • 13134 Shiloh Dr, Windsor, VA 23487
    13134 Shiloh Dr, Windsor, VA 23487
    13134 Shiloh Dr, Windsor, VA 23487
    /44

    $609,000

    • 3 Beds
    • 2.5 Baths
    • 4,037 Sq Ft

    13134 Shiloh Dr, Windsor, VA 23487

    Country living at its finest! Beautiful home located on 1 acre; conveniently located near Hwy 460 for an easy commute to anywhere in Hampton Roads. This home is ready for entertaining with a salt water inground pool, fire pits, gazebo, and composite deck off of the back of the home. Inside the home you'll find an open floor plan downstairs with a lovely family room, open to a spacious kitchen

    Amy Willette Cross Realty

    13134 Shiloh Dr, Windsor, VA 23487
  • 25092 Tyler Dr, Windsor, VA 23487
    25092 Tyler Dr, Windsor, VA 23487
    25092 Tyler Dr, Windsor, VA 23487
    /47

    $549,500

    $76K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,567 Sq Ft

    25092 Tyler Dr, Windsor, VA 23487

    Make this your home with your personal touches! $25,000 credit paid at closing to be used at buyers discretion for property upgrades/flooring/paint/closing costs (subject to lender approval) etc. One year home warranty of buyers choice up to $700. Instant equity potential! Appraised 2026 $600K. 4.71 acres & no HOA in Windsor VA. 1994 brick home offering classic durability & modern efficiency.

    Tracy Pudder World Class Realty

    25092 Tyler Dr, Windsor, VA 23487
  • 15+AC Courthouse Hwy, Windsor, VA 23487
    15+AC Courthouse Hwy, Windsor, VA 23487
    15+AC Courthouse Hwy, Windsor, VA 23487
    /3

    $200,000

    • Land
    • 17.69 Acres
    • $11,306 per Acre

    15+AC Courthouse Hwy, Windsor, VA 23487

    Great opportunity to purchase almost 20 acres of land in the town of Windsor VA. There is an easement that gives 50' of road frontage the land is zoned Residential.

    JR Doughty 1st Class Real Estate Norfolk

    15+AC Courthouse Hwy, Windsor, VA 23487
Virginia Isle Of Wight County

Homes for Sale with Acreage in Windsor, VA

Home Prices in Windsor, VA

The median home sale price in Windsor, VA is $378,000, up 66% year-over-year. Homes in Windsor sell in 39 days on average, compared to the national average of 55 days.

Home Price Trends

Median Sale Price
$378,000
Median Single Family Sale Price
$484,500
Median 2 Bedroom Sale Price
$269,000
Average Price Per Sq Ft
$215
Number of Homes for Sale
6
Last 12 months Home Sales
59
Months of Supply
7.10
Median List Price
$455,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
66%
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