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Windsor, VA Homes for Sale

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  • 39 Bank St, Windsor, VA 23487
    39 Bank St, Windsor, VA 23487
    39 Bank St, Windsor, VA 23487
    /37

    $374,800

    • 4 Beds
    • 2.5 Baths
    • 2,800 Sq Ft

    39 Bank St, Windsor, VA 23487

    This beautifully renovated 2,800 sq. ft. home on 2.30 acres in the heart of Windsor is truly a must-see! Taken down to the studs & completely rebuilt, everything is NEW—roof, siding, windows, HVAC, plumbing, lighting, drywall, & flooring. The spacious layout offers a FIRST FLOOR primary suite with a full bath, a large living room, a cozy den, & a mudroom for added convenience. The stunning

    Agent Photo

    Rachel Beasley

    Own Real Estate LLC

    (757) 908-6315

    39 Bank St, Windsor, VA 23487
  • 31 Bank St, Windsor, VA 23487
    31 Bank St, Windsor, VA 23487
    31 Bank St, Windsor, VA 23487
    /41

    $474,900 New Construction

    • 4 Beds
    • 2.5 Baths
    • 1,425 Sq Ft

    31 Bank St, Windsor, VA 23487

    Pioneer Model to be built on 5.78 acres in the heart of Windsor!! This 4 bedroom home has it all. Front Porch leads into the foyer. On forward the Living room is open to Dining and Kitchen all with LVP flooring. Kitchen with granite counters, tile backsplash, SS appliances. Primary Bedroom is large with walk-in-closet & lovely bathroom with gorgeous vanity, tile flooring & nice shower. Bedrooms

    Agent Photo

    Rachel Beasley

    Own Real Estate LLC

    (757) 798-8402

    31 Bank St, Windsor, VA 23487
  • 18052 Foxfire Trail, Windsor, VA 23487
    18052 Foxfire Trail, Windsor, VA 23487
    18052 Foxfire Trail, Windsor, VA 23487
    /41

    $799,000 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,400 Sq Ft

    18052 Foxfire Trail, Windsor, VA 23487

    Hello Barndos! The Aspen Barndominium to be built on 21+ acres of wooded paradise. Customize this 4 bedroom 2.5 bath barndo w/ your style, colors & finishes w/ the builder. Stunning Covered Front Porch leads to the Open Great Room designed w/ 15+ ft vaulted ceiling for the perfect open Living, Dining and Kitchen space. Kitchen w/ Stainless Steel Appliances, granite counters, tile backsplash &

    Agent Photo

    Rachel Beasley

    Own Real Estate LLC

    (757) 863-1318

    18052 Foxfire Trail, Windsor, VA 23487
  • 10 Church St, Windsor, VA 23487
    10 Church St, Windsor, VA 23487
    10 Church St, Windsor, VA 23487
    /23

    $374,900

    • 3 Beds
    • 2.5 Baths
    • 2,000 Sq Ft

    10 Church St, Windsor, VA 23487

    Welcome Home to this Spacious and Beautiful Farm House on almost 1/2 an acre Nestled in the Heart of Windsor! Renovated to Include: Soft Close Shaker Style Cabinets, Granite Counters, Tiled Back Splash, Stainless Steel Appliances, Carpet, Paint, LVP Flooring, Upgraded Lighting and Fixtures! New Roof, HVAC and Most Windows are Brand New! Owners Retreat Offers a HUGE walk in Closet, Formal Dining

    Karen Swaney Salty Dog Realty LLC

    10 Church St, Windsor, VA 23487
  • 13067 Poor House Rd, Windsor, VA 23487
    13067 Poor House Rd, Windsor, VA 23487
    13067 Poor House Rd, Windsor, VA 23487
    /36

    $349,000

    • 3 Beds
    • 2 Baths
    • 1,515 Sq Ft

    13067 Poor House Rd, Windsor, VA 23487

    Welcome to this beautifully updated 3-bedroom, 2-bath rancher on a spacious lot! This home features a large remodeled interior, including a generous primary suite with private bath. Enjoy a bright, open layout with updated flooring, fixtures, and fresh paint throughout. The kitchen flows easily into the living and dining spaces, making it perfect for everyday living or entertaining. Step outside

    Candice Vande Brake Surry Side Realty

    13067 Poor House Rd, 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

    $525,000

    • Land
    • 18 Acres
    • $29,678 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
  • 432 Bracey Cir, Windsor, VA 23487
    432 Bracey Cir, Windsor, VA 23487
    432 Bracey Cir, Windsor, VA 23487
    /8

    $54,900

    • 1 Bed
    • 1 Bath
    • 672 Sq Ft

    432 Bracey Cir, Windsor, VA 23487

    This beautiful 1 bedroom / 1 bath home is located on a quiet corner lot overlooking the pond.

    Tammy Newsom Clydes Dale

    432 Bracey Cir, Windsor, VA 23487
  • 24465 Curve Dr, Windsor, VA 23487
    24465 Curve Dr, Windsor, VA 23487
    24465 Curve Dr, Windsor, VA 23487
    /19

    $199,900

    • 3 Beds
    • 1.5 Baths
    • 926 Sq Ft

    24465 Curve Dr, Windsor, VA 23487

    Great Purchase Opportunity for a 3 Bedroom, 1.5 Bath Home with a Detached Garage in Town of Windsor Priced Below $200,000. Home has Vaulted Ceilings that Provides an Open Concept. Detached Garage with Power. Brand New Heat Pump in November, 2024. Relax on the Brick Patio in Back Yard.

    Dale Scott Scott & Assoc. Inc. Realtors

    24465 Curve Dr, Windsor, VA 23487
  • 66 Church St, Windsor, VA 23487
    66 Church St, Windsor, VA 23487
    66 Church St, Windsor, VA 23487
    /3

    $199,000

    • Land
    • 26 Acres
    • $7,710 per Acre

    66 Church St, Windsor, VA 23487

    25.81 acres in the Town of Windsor Va. divided into 5 parcels. Approximately 11 acres are in wetland. for more information Contact owners rep. Peter Acker (757-818-4527)

    James Acker Acker Real Estate Service

    66 Church St, Windsor, VA 23487
  • .71 Ac E Windsor Blvd, Windsor, VA 23487
    .71 Ac E Windsor Blvd, Windsor, VA 23487
    .71 Ac E Windsor Blvd, Windsor, VA 23487
    /9

    $175,000

    • Land
    • 0.71 Acre
    • $245,098 per Acre

    .71 Ac E Windsor Blvd, Windsor, VA 23487

    *FRONTAGE ON MAJOR HWY. ENTRANCE FROM ADJACENT PROPERTY IS AVAILABLE WHICH WOULD NOT REQUIRE TURN LANE.**SEE ATTACHED SURVEY.

    Durwood Scott Scott & Assoc. Inc. Realtors

    .71 Ac E Windsor Blvd, Windsor, VA 23487
  • Lot 11 Walters Hwy, Windsor, VA 23487
    Lot 11 Walters Hwy, Windsor, VA 23487
    /2

    $30,000

    • Land
    • 0.16 Acre
    • $187,500 per Acre

    Lot 11 Walters Hwy, Windsor, VA 23487

    This is 1 of 8 contiguous lots in Windsor. Preference is to sell all 8 as a package, or 2 lot (back to front) pairs. See attachment for more details to aid in your due diligence. Directions: From Smithfield, head south on 258, through Windsor, right on Bear Trap. From Suffolk - West on 460, right on 258, through Windsor, right on Bear Trap

    Robert Pickles KW Coastal Chesapeake Virginia LLC

    Lot 11 Walters Hwy, Windsor, VA 23487
  • Lot 10 Walters Hwy, Windsor, VA 23487
    Lot 10 Walters Hwy, Windsor, VA 23487
    /2

    $30,000

    • Land
    • 0.16 Acre
    • $187,500 per Acre

    Lot 10 Walters Hwy, Windsor, VA 23487

    This is 1 of 8 contiguous lots in Windsor. Preference is to sell all 8 as a package, or 2 lot (back to front) pairs. See attachment for more details to aid in your due diligence. Directions: From Smithfield, head south on 258, through Windsor, right on Bear Trap. From Suffolk - West on 460, right on 258, through Windsor, right on Bear Trap

    Robert Pickles KW Coastal Chesapeake Virginia LLC

    Lot 10 Walters Hwy, Windsor, VA 23487
  • Lot 9 Walters Hwy, Windsor, VA 23487
    Lot 9 Walters Hwy, Windsor, VA 23487
    /2

    $30,000

    • Land
    • 0.16 Acre
    • $187,500 per Acre

    Lot 9 Walters Hwy, Windsor, VA 23487

    This is 1 of 8 contiguous lots in Windsor. Preference is to sell all 8 as a package, or 2 lot (back to front) pairs. See attachment for more details to aid in your due diligence. Directions: From Smithfield, head south on 258, through Windsor, right on Bear Trap. From Suffolk - West on 460, right on 258, through Windsor, right on Bear Trap

    Robert Pickles KW Coastal Chesapeake Virginia LLC

    Lot 9 Walters Hwy, Windsor, VA 23487
  • LOT 8 Walters Hwy, Windsor, VA 23487
    LOT 8 Walters Hwy, Windsor, VA 23487
    /2

    $30,000

    • Land
    • 0.17 Acre
    • $176,471 per Acre

    LOT 8 Walters Hwy, Windsor, VA 23487

    This is 1 of 8 contiguous lots in Windsor. Preference is to sell all 8 as a package, or 2 lot (back to front) pairs. See attachment for more details to aid in your due diligence. Directions: From Smithfield, head south on 258, through Windsor, right on Bear Trap. From Suffolk - West on 460, right on 258, through Windsor, right on Bear Trap

    Robert Pickles KW Coastal Chesapeake Virginia LLC

    LOT 8 Walters Hwy, Windsor, VA 23487
  • Lot 24 Walters Hwy, Windsor, VA 23487
    Lot 24 Walters Hwy, Windsor, VA 23487
    /2

    $30,000

    • Land
    • 0.18 Acre
    • $166,667 per Acre

    Lot 24 Walters Hwy, Windsor, VA 23487

    This is 1 of 8 contiguous lots in Windsor. Preference is to sell all 8 as a package, or 2 lot (back to front) pairs. See attachment for more details to aid in your due diligence. Directions: From Smithfield, head south on 258, through Windsor, right on Bear Trap. From Suffolk - West on 460, right on 258, through Windsor, right on Bear Trap

    Robert Pickles KW Coastal Chesapeake Virginia LLC

    Lot 24 Walters Hwy, Windsor, VA 23487
  • Lot 23 Walters Hwy, Windsor, VA 23487
    Lot 23 Walters Hwy, Windsor, VA 23487
    /2

    $30,000

    • Land
    • 0.17 Acre
    • $176,471 per Acre

    Lot 23 Walters Hwy, Windsor, VA 23487

    This is 1 of 8 contiguous lots in Windsor. Preference is to sell all 8 as a package, or 2 lot (back to front) pairs. See attachment for more details to aid in your due diligence. Directions: From Smithfield, head south on 258, through Windsor, right on Bear Trap. From Suffolk - West on 460, right on 258, through Windsor, right on Bear Trap

    Robert Pickles KW Coastal Chesapeake Virginia LLC

    Lot 23 Walters Hwy, Windsor, VA 23487
  • Lot 22 Walters Hwy, Windsor, VA 23487
    Lot 22 Walters Hwy, Windsor, VA 23487
    /2

    $30,000

    • Land
    • 0.16 Acre
    • $187,500 per Acre

    Lot 22 Walters Hwy, Windsor, VA 23487

    This is 1 of 8 contiguous lots in Windsor. Preference is to sell all 8 as a package, or 2 lot (back to front) pairs. See attachment for more details to aid in your due diligence. Directions: From Smithfield, head south on 258, through Windsor, right on Bear Trap. From Suffolk - West on 460, right on 258, through Windsor, right on Bear Trap

    Robert Pickles KW Coastal Chesapeake Virginia LLC

    Lot 22 Walters Hwy, Windsor, VA 23487
  • Lot 21 Walters Hwy, Windsor, VA 23487
    Lot 21 Walters Hwy, Windsor, VA 23487
    /2

    $30,000

    • Land
    • 0.18 Acre
    • $166,667 per Acre

    Lot 21 Walters Hwy, Windsor, VA 23487

    This is 1 of 8 contiguous lots in Windsor. Preference is to sell all 8 as a package, or 2 lot (back to front) pairs. See attachment for more details to aid in your due diligence.Directions: From Smithfield, head south on 258, through Windsor, right on Bear Trap. From Suffolk - West on 460, right on 258, through Windsor, right on Bear Trap

    Robert Pickles KW Coastal Chesapeake Virginia LLC

    Lot 21 Walters Hwy, Windsor, VA 23487
Virginia Windsor

Real Estate & Homes for Sale in Windsor, VA

Why Live in Windsor

Windsor, located at the junction of Route 460 and Route 258, is a small rural town 12 miles west of Suffolk. Known for its peaceful and friendly atmosphere, Windsor offers a mix of single-family homes, including 1920s farmhouses, 1960s ranch styles, and modern traditional homes from the 2000s. Many properties feature large lots of half an acre or more, with home sizes ranging from 1,000 to 2,900 square feet. Dining options along U.S. Route 460 include local favorites like Anna’s Ristorante and El Rodeo, while grocery needs can be met at the nearby Food Lion. For shopping beyond groceries, The Sassy Sisters offers antiques and home décor. Windsor Elementary, rated highly by Niche, serves the local children, along with Tyler Middle and Windsor High School, both of which also receive good ratings. Outdoor activities are centered around Robinson Park, which features a playground and picnic shelter, and the Windsor Public Library. Community events such as free concerts at Garis Park and the annual Christmas parade foster a strong sense of local spirit. Heritage Park hosts the Isle of Wight County Fair and Fourth of July fireworks. Despite its historical ties to transportation, Windsor lacks public transit, making car travel essential for residents.
Learn more about living in Windsor

Frequently Asked Questions

What is the average home price in Windsor, VA?
Homes for sale in Windsor, VA have an average home price of $372,091.
How many homes have sold over the last 12 months in Windsor, VA?
51 homes have sold in Windsor, VA over the last 12 months.
Is Windsor, VA a safe city?
In general, the safest neighborhood in Windsor, VA with lower crime scores is Southern Isle of Wight.
What are the most popular zip codes in Windsor, VA?
The most popular zip codes in Windsor, VA include 23434, 23435, 23321, 23666 and 23430.
What are the most popular neighborhoods in Windsor, VA?
The most popular neighborhood in Windsor, VA with the most homes for sale is Southern Isle of Wight.
How much do you need to make to afford a house in Windsor?
The median home price in Windsor is $363,000. If you put a 20% down payment of $72,600 and had a 30-year fixed mortgage with an interest rate of 6.77%, your estimated principal and interest payment would be $1,890 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $81K a year to afford the median home price in Windsor.
How are the schools in Windsor, VA?
Windsor, VA has highly rated public and private schools. Some of the best schools in Windsor based on Niche Grades are Carrsville Elementary School, Windsor Elementary School and Georgie D. Tyler Middle School. The neighborhood in Windsor with the highest rated schools is Southern Isle of Wight. Browse all the schools in Windsor, VA to learn more.

Home Trends in Windsor, VA

On average, homes in Windsor, VA sell after 40 days on the market compared to the national average of 50 days. The median sale price for homes in Windsor, VA over the last 12 months is $360,000, up 3% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$360,000
Median Single Family Sale Price
$361,000
Average Price Per Sq Ft
$195
Number of Homes for Sale
24
Last 12 months Home Sales
51
Months of Supply
5.60
Median List Price
$363,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
3%
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