28

Windsor, VA Homes for Sale

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  • /48

    $509,990 New Construction

    • 4 - 5 Beds
    • 2.5 - 3.5 Baths
    • 2,449 Sq Ft

    Raleigh Plan at Windsor Station, Windsor, VA 23487

    The Raleigh is a two-story, four-bedroom, two-and-a-half-bath home with a first-floor primary bedroom, formal dining room, two-story family room, and a kitchen with an island and pantry. The second floor features an upstairs loft area, three additional bedrooms, and a full bath.Options to personalize this home include an expanded loft area, an enclosed bonus room, a second primary bedroom

    Eastwood Homes Builder
    0 Shiloh Dr Unit 36498467, Windsor, VA 23487
  • /2

    $599,990 New Construction

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

    12199 Ava Ln, Windsor, VA 23487

    The Asheboro 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.

    Eastwood Homes Builder
    12199 Ava Ln, Windsor, VA 23487
  • /34

    $574,990 New Construction

    • 4 - 6 Beds
    • 3.5 - 4.5 Baths
    • 3,294 Sq Ft

    McDowell Plan at Windsor Station, Windsor, VA 23487

    The McDowell is a two-story, four-bedroom, three-and-a-half-bath home with a first-floor primary bedroom, formal dining room, two-story family room, kitchen with an island and pantry, and a separate breakfast area. The second floor features three spacious bedrooms and two additional baths, including a Jack-and-Jill bath between bedrooms two and three, an oversized open loft area, and an

    Eastwood Homes Builder
    0 Shiloh Dr Unit 36500947, Windsor, VA 23487
  • /48

    $514,990 New Construction

    • 4 - 5 Beds
    • 3 - 4 Baths
    • 2,430 Sq Ft

    Cypress Plan at Windsor Station, Windsor, VA 23487

    The Cypress is a two-story, four-bedroom, three-bath home with a formal dining room, a first-floor guest suite with a full bath, and a kitchen with an island and pantry. The second floor features the primary bedroom, two additional bedrooms, a hall bath, a convenient upstairs laundry room, and an oversized loft area. Options available to personalize your home include a sunroom, screen porch, or

    Eastwood Homes Builder
    0 Shiloh Dr Unit 36476046, Windsor, VA 23487
  • /70

    $534,990 New Construction

    • 3 - 4 Beds
    • 2.5 - 3.5 Baths
    • 2,583 Sq Ft

    Asheboro Plan at Windsor Station, Windsor, VA 23487

    The Asheboro is a three-bedroom, two-and-a-half-bath home with a first-floor primary bedroom, formal dining room, spacious family room, kitchen with island and pantry, and a Jack and Jill bath between bedrooms two and three. Options to personalize this home include an office with French doors, a sunroom, a covered porch or screen porch, a butler's pantry, a drop zone area, and upstairs options

    Eastwood Homes Builder
    0 Shiloh Dr Unit 36446317, Windsor, VA 23487
  • /62

    $579,990 New Construction

    • 5 - 6 Beds
    • 3 - 4 Baths
    • 3,483 Sq Ft

    Charleston Plan at Windsor Station, Windsor, VA 23487

    The Charleston is a stunning two-story, five-bedroom, three-bath home with formal living and dining rooms, a kitchen with an island and pantry, a first-floor guest suite with a full bath, an oversized entry from the garage, and a two-story family room. The second floor features four bedrooms, including the primary with two closets, a large laundry room, and an additional full bath.Options

    Eastwood Homes Builder
    0 Shiloh Dr Unit 36484718, Windsor, VA 23487
  • /2

    $549,990 New Construction

    • 4 Beds
    • 3 Baths
    • 2,438 Sq Ft

    12169 Ava Ln, Windsor, VA 23487

    The Cypress is a two-story, four-bedroom, three-bath home with a formal dining room, a first-floor guest suite with a full bath, and a kitchen with an island and pantry. The second floor features the primary bedroom, two additional bedrooms, a hall bath, a convenient upstairs laundry room, and an oversized loft area.

    Eastwood Homes Builder
    12169 Ava Ln, Windsor, VA 23487
  • /63

    $589,990 New Construction

    • 5 Beds
    • 4 - 4.5 Baths
    • 3,691 Sq Ft

    Roanoke Plan at Windsor Station, Windsor, VA 23487

    The Roanoke is a stunning two-story, five-bedroom, four-bath home with a formal dining room, a dedicated office space with French doors, a spacious family room, a kitchen with an island and pantry, and a first-floor guest suite with a full bath. The second floor features the primary suite with dual closets, three secondary bedrooms with walk-in closets, a hall bath, a shared Jack and Jill bath

    Eastwood Homes Builder
    0 Shiloh Dr Unit 36445447, Windsor, VA 23487
  • /71

    $544,990 New Construction

    • 5 - 6 Beds
    • 3 - 4 Baths
    • 3,047 Sq Ft

    Davidson Plan at Windsor Station, Windsor, VA 23487

    The Davidson is a two-story, five-bedroom, three-bath home with a formal living room, formal dining room, spacious family room, kitchen with island and pantry, separate breakfast area, and first-floor guest suite with a full bath. The second floor features four bedrooms, including the primary bedroom with an attached, private primary bath, an additional full bath, a large laundry room, and a loft

    Eastwood Homes Builder
    0 Shiloh Dr Unit 36500583, 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
  • /23

    $332,800

    • 5 Beds
    • 3.5 Baths
    • 2,729 Sq Ft

    29 N Court St, Windsor, VA 23487

    Come see this 5 bedroom, 3.5 bath home in Windsor with detached garage and in-law suite.

    Kevin Pall Brooke Madison & Associates

    29 N Court St, Windsor, VA 23487
  • /39

    $509,990

    • 4 Beds
    • 3.5 Baths
    • 2,449 Sq Ft

    MM Raleigh, Windsor, VA 23487

    The Raleigh is a two-story, four-bedroom, two-and-a-half-bath home with a first-floor primary bedroom, formal dining room, two-story family room, and a kitchen with an island and pantry. The second floor features an upstairs loft area, three additional bedrooms, and a full bath .Options to personalize this home include an expanded loft area, an enclosed bonus room, a second primary bedroom

    Amanda Reyes BHHS RW Towne Realty

    MM Raleigh, Windsor, VA 23487
  • /32

    $519,990

    • 4 Beds
    • 2.5 Baths
    • 2,591 Sq Ft

    MM Windsor Station (Drexel), Windsor, VA 23487

    The Drexel is a two-story, four-bedroom, two-and-a-half-bath home with a formal living room, formal dining room, kitchen with island and a pantry, and a spacious great room. The second floor features four bedrooms, including the primary suite with a large closet, an upstairs laundry, an additional full bath, and a loft area. Options to personalize this home include a home office, bay window in

    Amanda Reyes BHHS RW Towne Realty

    MM Windsor Station (Drexel), Windsor, VA 23487
  • /10

    $499,990 New Construction

    • 3 - 5 Beds
    • 2 - 4 Baths
    • 2,071 Sq Ft

    Caldwell Plan at Windsor Station, Windsor, VA 23487

    The Caldwell is a ranch-style home with three bedrooms, two full baths, a first-floor primary bedroom with two closets, a convenient pocket office for a dedicated work or study-from-home space, a formal dining room, a spacious family room, and a kitchen with an island and pantry. Options available to personalize this home include an office instead of the formal dining room or bedroom two, a

    Eastwood Homes Builder
    0 Shiloh Dr Unit 36474900, Windsor, VA 23487
  • /39

    $544,990

    • 5 Beds
    • 3 Baths
    • 3,047 Sq Ft

    MM Davidson, Windsor, VA 23487

    The Davidson is a two-story, five-bedroom, three-bath home with a formal living room, formal dining room, spacious family room, kitchen with island and pantry, separate breakfast area, and first-floor guest suite with a full bath. The second floor features four bedrooms, including the primary bedroom with an attached, private primary bath, an additional full bath, a large laundry room, and a loft

    Amanda Reyes BHHS RW Towne Realty

    MM Davidson, Windsor, VA 23487
  • /37

    $534,990

    • 3 Beds
    • 2.5 Baths
    • 2,583 Sq Ft

    MM Asheboro, Windsor, VA 23487

    The Asheboro at Windsor Station is a three-bedroom, two-and-a-half-bath home with a first-floor primary bedroom, formal dining room, spacious family room, kitchen with island and pantry, and a Jack and Jill bath between bedrooms two and three. Options to personalize this home include an office with French doors, a sunroom, a covered porch or screen porch, a butler's pantry, a drop zone area, and

    Shane Fuson BHHS RW Towne Realty

    MM Asheboro, 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
  • /47

    $545,000

    • 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 massive

    Anna Boyer Howard Hanna Real Estate Svcs.

    17314 Jolly Cir, Windsor, VA 23487
  • /40

    $430,000

    • 3 Beds
    • 2 Baths
    • 2,010 Sq Ft

    14494 Bowling Green Rd, Windsor, VA 23487

    Set on a private 2-acre lot, this well-maintained brick home offers space, comfort, and efficiency. With 2,010 square feet of living space plus a sunroom and attached garage, there is room to spread out both inside and out. Enjoy outdoor living with a large back deck, patio off the sunroom, and a storage shed, all surrounded by peaceful privacy. Inside, the main living area features vaulted

    Anna Boyer Howard Hanna Real Estate Svcs.

    14494 Bowling Green Rd, Windsor, VA 23487
  • /50

    $589,990

    • 5 Beds
    • 4 Baths
    • 3,691 Sq Ft

    MM Roanoke, Windsor, VA 23487

    Welcome to the Roanoke by Eastwood Homes at Windsor Station! This beautifully designed two-story home offers 4 bedrooms, 3 baths, and an open concept great for modern living. The spacious family room flows seamlessly into the designer kitchen featuring a large island, quartz countertops, and upgraded cabinetry. A first-floor guest suite with a full bath adds flexibility for guests or a home

    Shane Fuson BHHS RW Towne Realty

    MM Roanoke, 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
  • /46

    $499,990

    • 3 Beds
    • 2 Baths
    • 2,071 Sq Ft

    MM Caldwell, Windsor, VA 23487

    The Caldwell is a ranch-style home with three bedrooms, two full baths, a first-floor primary bedroom with two closets, a convenient pocket office for a dedicated work or study-from-home space, a formal dining room, a spacious family room, and a kitchen with an island and pantry. Options available to personalize this home include an office instead of the formal dining room or bedroom two, a

    Amanda Reyes BHHS RW Towne Realty

    MM Caldwell, Windsor, VA 23487
  • /50

    $574,990

    • 4 Beds
    • 3.5 Baths
    • 3,294 Sq Ft

    MM Mcdowell, Windsor, VA 23487

    The McDowell at Windsor Station is a two-story, four-bedroom, three-and-a-half-bath home with a first-floor primary bedroom, formal dining room, two-story family room, kitchen with an island and pantry, and a separate breakfast area. The second floor features three spacious bedrooms and two additional baths, including a Jack-and-Jill bath between bedrooms two and three, an oversized open loft

    Shane Fuson BHHS RW Towne Realty

    MM Mcdowell, Windsor, VA 23487
  • /50

    $579,990

    • 5 Beds
    • 3 Baths
    • 3,483 Sq Ft

    MM Charleston, Windsor, VA 23487

    The Charleston at Windsor Station is a stunning two-story, five-bedroom, three-bath home with formal living and dining rooms, a kitchen with an island and pantry, a first-floor guest suite with a full bath, an oversized entry from the garage, and a two-story family room. The second floor features four bedrooms, including the primary with two closets, a large laundry room, and an additional full

    Shane Fuson BHHS RW Towne Realty

    MM Charleston, Windsor, VA 23487
  • /65

    $519,990 New Construction

    • 4 - 5 Beds
    • 2.5 - 3.5 Baths
    • 2,591 Sq Ft

    Drexel Plan at Windsor Station, Windsor, VA 23487

    The Drexel is a two-story, four-bedroom, two-and-a-half-bath home with a formal living room, formal dining room, kitchen with island and a pantry, and a spacious great room. The second floor features four bedrooms, including the primary suite with a large closet, an upstairs laundry, an additional full bath, and a loft area. Options to personalize this home include a home office, bay window in

    Eastwood Homes Builder
    0 Shiloh Dr Unit 36487210, 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
  • /50

    $450,000 Open Sun 2PM - 4PM

    • 5 Beds
    • 3 Baths
    • 2,797 Sq Ft

    23068 Andrew Ct, Windsor, VA 23487

    Located in the established Windsor Woods community, this spacious 5-bedroom, 3-full-bath home offers a flexible layout and comfortable living with no HOA. The first floor features a primary suite and a guest bedroom, along with soaring cathedral ceilings that fill the home with natural light and create an open, airy feel. Upstairs offers three additional generously sized bedrooms with excellent

    Amanda Emanuel BHHS RW Towne Realty

    23068 Andrew Ct, Windsor, VA 23487
  • /7

    $425,000

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

    11480 Blue Ridge Trail, Windsor, VA 23487

    NEW PRICE ADJUSTMENT ! 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

    Donnie Upton Upton Realty

    11480 Blue Ridge Trail, Windsor, VA 23487

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.

Frequently Asked Questions

What is the average home price in Windsor, VA?
Homes for sale in Windsor, VA have an average home price of $430,823.
How many homes have sold over the last 12 months in Windsor, VA?
58 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 23487, 23434, 23898, 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 $435,000. If you put a 20% down payment of $87,000 and had a 30-year fixed mortgage with an interest rate of 6.21%, your estimated principal and interest payment would be $2,130 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $91K a year to afford the median home price in Windsor. Learn how much home you can afford with our Home Affordability Calculator.
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

Housing Trends

Median Sale Price
$389,450
Median Single Family Sale Price
$435,000
Average Price Per Sq Ft
$202
Number of Homes for Sale
25
Last 12 months Home Sales
58
Months of Supply
5.20
Median List Price
$435,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
34%
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