29

Windsor, VA Homes for Sale

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  • 25452 Walters Hwy, Windsor, VA 23487
    25452 Walters Hwy, Windsor, VA 23487
    25452 Walters Hwy, Windsor, VA 23487
    /43

    $495,000

    • 5 Beds
    • 2 Baths
    • 2,500 Sq Ft

    25452 Walters Hwy, Windsor, VA 23487

    Looking for space and privacy? Look no further! This 5-bed, 2-bath, 2,500-square-foot rancher with both a 2-car attached garage and a large, oversized detached barn is the perfect combination. Sitting on exactly an acre, this home offers peace and quiet while being conveniently located near town.

    Jordan Cowles EXP Realty LLC

    25452 Walters Hwy, Windsor, VA 23487
  • 15023 Five Forks Rd, Windsor, VA 23487
    15023 Five Forks Rd, Windsor, VA 23487
    15023 Five Forks Rd, Windsor, VA 23487
    /50

    $1,200,000

    • 3 Beds
    • 3.5 Baths
    • 2,919 Sq Ft

    15023 Five Forks Rd, Windsor, VA 23487

    12-acres of exceptional beauty and privacy features a welcoming picket fence and crepe myrtles entrance. The driveway is flanked by scenic cotton fields leading to a picturesque 3-acre pond, fully stocked with fish! Custom all-brick home showcases mature trees, a peaceful setting, and spacious back porch w/ fans extending across the rear of the house overlooking the pond. Spacious entertaining

    Gayle Upchurch BHHS RW Towne Realty

    15023 Five Forks Rd, Windsor, VA 23487
  • .33 ac Central Hill Rd, Windsor, VA 23487
    .33 ac Central Hill Rd, Windsor, VA 23487
    .33 ac Central Hill Rd, Windsor, VA 23487
    /4

    $47,900

    • Land
    • 0.33 Acre
    • $145,152 per Acre

    .33 ac Central Hill Rd, Windsor, VA 23487

    They are two adjacent lots with about 14,500 sq ft- lot dimensions are approx (120 x 122)- Single family homes on either side of the lot -no water or sewer

    Jeanette McCallum Partners In Real Estate

    .33 ac Central Hill Rd, Windsor, VA 23487
  • 17314 Jolly Cir, Windsor, VA 23487
    17314 Jolly Cir, Windsor, VA 23487
    17314 Jolly Cir, Windsor, VA 23487
    /47

    $570,000

    • 4 Beds
    • 3 Baths
    • 1,749 Sq Ft

    17314 Jolly Cir, Windsor, VA 23487

    Experience the perfect blend of charm, space, and functionality with this beautifully crafted brick home set on 2.57 acres. Offering 4 bedrooms and 3 full baths, this residence features beautiful hardwood floors, a recently updated kitchen, and a spacious basement ideal for additional living or entertaining space. Outdoors, the property is a dream for hobbyists and collectors, boasting a

    Anna Boyer Howard Hanna Real Estate Services

    17314 Jolly Cir, Windsor, VA 23487
  • 18 B Ave, Windsor, VA 23487
    18 B Ave, Windsor, VA 23487
    18 B Ave, Windsor, VA 23487
    /28

    $232,900

    • 3,600 Sq Ft

    18 B Ave, Windsor, VA 23487

    Calling all investors and house hackers! This duplex is a fantastic opportunity for an investor or a buyer looking to build equity through renovations. This property is ready for its next chapter and offers incredible potential. Perfect for someone willing to put in the work, this property is being sold as-is, where-is, with the sellers making no repairs. The location is ideal in the heart of

    Lee Cross Cross Realty

    18 B Ave, Windsor, VA 23487
  • 11480 Blue Ridge Trail, Windsor, VA 23487
    11480 Blue Ridge Trail, Windsor, VA 23487
    11480 Blue Ridge Trail, Windsor, VA 23487
    /7

    $475,000

    • 3 Beds
    • 2.5 Baths
    • 1,876 Sq Ft

    11480 Blue Ridge Trail, Windsor, VA 23487

    Idyllic Farmstead Escape with Equine Facilities & Expansive ComfortWelcome to your private countryside haven—where timeless charm meets modern ease across 9.03 acres of rolling pastureland. This beautifully appointed 3-bedroom, 3-bath home offers a lifestyle of serenity, space, and opportunity.Inside, the generous living room invites connection and comfort, while the well-equipped

    Donnie Upton Upton Realty

    11480 Blue Ridge Trail, Windsor, VA 23487
  • 10 Church St, Windsor, VA 23487
    10 Church St, Windsor, VA 23487
    10 Church St, Windsor, VA 23487
    /24

    $349,900

    • 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
  • 24465 Curve Dr, Windsor, VA 23487
    24465 Curve Dr, Windsor, VA 23487
    24465 Curve Dr, Windsor, VA 23487
    /19

    $182,000

    • 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. Home has Vaulted Ceilings that Provides an Open Concept and Versatile Floor Plan. 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
  • 13067 Poor House Rd, Windsor, VA 23487
    13067 Poor House Rd, Windsor, VA 23487
    13067 Poor House Rd, Windsor, VA 23487
    /34

    $329,900

    • 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

    $395,000

    • Land
    • 17.69 Acres
    • $22,329 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
  • .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

    $25,000

    • Land
    • 0.16 Acre
    • $156,250 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

    $25,000

    • Land
    • 0.16 Acre
    • $156,250 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

    $25,000

    • Land
    • 0.16 Acre
    • $156,250 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

    $25,000

    • Land
    • 0.17 Acre
    • $147,059 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

    $25,000

    • Land
    • 0.18 Acre
    • $138,889 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

    $25,000

    • Land
    • 0.17 Acre
    • $147,059 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

    $25,000

    • Land
    • 0.16 Acre
    • $156,250 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

    $25,000

    • Land
    • 0.18 Acre
    • $138,889 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
  • 12199 Ava Ln, Windsor, VA 23487
    12199 Ava Ln, Windsor, VA 23487
    12199 Ava Ln, Windsor, VA 23487
    /45

    $599,990 New Construction

    • 4 Beds
    • 3.5 Baths
    • 3,201 Sq Ft

    12199 Ava Ln, Windsor, VA 23487

    The Asheboro in Windsor Station is a four-bedroom, three-and-a-half-bath home featuring a first-floor primary bedroom, formal dining room, spacious family room, kitchen with an island and pantry, and a Jack-and-Jill bath between bedrooms two and three. The second floor features a loft, an additional bedroom, and a full bathroom. Receive up to $15,000 in closing costs!

    Shane Fuson BHHS RW Towne Realty

    12199 Ava Ln, Windsor, VA 23487
Virginia Isle Of Wight County Windsor

Real Estate & Homes for Sale in Windsor, VA

Why Live in Windsor

Windsor, Virginia, located at the junction of Route 460 and Route 258, is a small rural town 12 miles west of Suffolk. Known for its peaceful atmosphere and friendly community, Windsor offers a traditional small-town American lifestyle. Homebuyers can choose from a variety of single-family homes, including 1920s farmhouses, 1960s ranch styles, and modern homes from the 2000s, many of which sit on large lots. Windsor Elementary is highly rated, making the town appealing for families. Dining options include local favorites like Anna’s Ristorante, known for its award-winning pizza, and the popular El Rodeo Mexican restaurant. For shopping, residents can visit The Sassy Sisters for antiques and home décor. Outdoor activities are centered around Robinson Park, which features a playground and picnic shelter, and the nearby Windsor Public Library. Community events such as free concerts at Garis Park, the annual Christmas parade, and the Isle of Wight County Fair at Heritage Park foster a strong sense of local spirit. While Windsor lacks public transit, its location provides convenient access to the Hampton Roads region, making it a practical choice for commuters.

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 $408,622.
How many homes have sold over the last 12 months in Windsor, VA?
50 homes have sold in Windsor, VA over the last 12 months.
What are the most popular zip codes in Windsor, VA?
The most popular zip codes in Windsor, VA include 23487, 23898, 23434, 23315 and 23437.
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 $396,250. If you put a 20% down payment of $79,200 and had a 30-year fixed mortgage with an interest rate of 6.17%, your estimated principal and interest payment would be $1,940 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $83K 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 Windsor Elementary School, Carrsville 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 38 days on the market compared to the national average of 53 days. The median sale price for homes in Windsor, VA over the last 12 months is $393,250, up 55% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$393,250
Median Single Family Sale Price
$397,500
Average Price Per Sq Ft
$203
Number of Homes for Sale
25
Last 12 months Home Sales
50
Months of Supply
6.00
Median List Price
$396,250
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
55%
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