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Windsor, VA Houses for Sale

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  • /20

    $460,000 Open Sat 9AM - 12PM

    • 4 Beds
    • 3 Baths
    • 2,535 Sq Ft

    10455 Sylvia Cir, Windsor, VA 23487

    Welcome to this well-maintained transitional-style home located in the Windsor Woods subdivision in Windsor, Virginia. Built in 2006, this property offers over 2,500 sqft with four bedrooms, a loft, a dedicated office, and three full baths, creating flexible living options for today’s needs. The first-floor primary suite includes a handicap friendly walk-in shower and soaking tub, while an

    Agent Photo

    Mark Rusnak

    RE/MAX Allegiance

    (757) 919-3574

    10455 Sylvia Cir, Windsor, VA 23487
  • /10

    $714,900 New Construction

    • 4 Beds
    • 3 Baths
    • 2,901 Sq Ft

    47AC Holland Dr, Windsor, VA 23487

    WELCOME TO THE CAPRON, THE LATEST CREATION FROM SOUTHEASTERN VIRGINIA'S PREMIER RURAL CUSTOM HOME BUILDER. THE CAPRON CENTERS AROUND A BRIGHT, OPEN CONCEPT FLOOR PLAN THAT SEAMLESSLY INTEGRATES THE LARGE LIVING ROOM, DINING AREA, AND GOURMET KITCHEN COMPLETE WITH A GENEROUS ISLAND AND PLENTY OF STORAGE. BUILT IN BOOKSHELVES IN THE LIVING ROOM AND BOTH CHARM AND FUNCTION. WHETHER YOU'RE HOSTING A

    Agent Photo

    Dan Lawson

    Green Tree Real Estate Inc

    (757) 863-3867

    47AC Holland Dr, 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
  • /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

    $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
  • /32

    $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

    $598,990 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
  • /39

    $509,990 New Construction

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

    MM Windsor Station (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

    Lori Cutrell BHHS RW Towne Realty

    MM Windsor Station (Raleigh), Windsor, VA 23487
  • /32

    $519,990 New Construction

    • 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

    Lori Cutrell 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
  • /4

    $559,900 New Construction

    • 4 Beds
    • 3.5 Baths
    • 2,347 Sq Ft

    11563 Savannah St, Windsor, VA 23487

    This NEW Kestrel Ranch is move-in ready in June! Cozy cottage style on the outside leads to classic touches on the inside, with 2-panel interior doors with lever handles, shaker style cabinets with soft close and black hardware, granite countertops, double ovens and tile backsplash in the kitchen, with warm and low maintenance LVP in main living areas, LVT in baths and tile shower in the Primary

    Jamie Roser Wainwright Real Estate

    11563 Savannah St, Windsor, VA 23487
  • /39

    $544,990 New Construction

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

    MM Windsor Station (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

    Lori Cutrell BHHS RW Towne Realty

    MM Windsor Station (Davidson), Windsor, VA 23487
  • /6

    $589,900 New Construction

    • 4 Beds
    • 3.5 Baths
    • 2,618 Sq Ft

    12185 Ava Ln, Windsor, VA 23487

    This NEW Kestrel Ranch in Windsor Station is move-in ready in May! Beautiful Craftsman touches begin with the exterior stone columns and accents, to the interior doors, trim and shaker style cabinets. Warm and durable LVP is located in all main living spaces. The home features a thoughtful layout including 2 Bedrooms, Primary Suite with tile shower and two walk-in closets, half bath and open

    Jamie Roser Wainwright Real Estate

    12185 Ava Ln, Windsor, VA 23487
  • /37

    $534,990 New Construction

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

    MM Windsor Station (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

    Lori Cutrell BHHS RW Towne Realty

    MM Windsor Station (Asheboro), 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

    $548,990 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
  • /23

    $679,000 New Construction

    • 4 Beds
    • 3.5 Baths
    • 2,668 Sq Ft

    14002 Old Suffolk Rd, Windsor, VA 23487

    Beautiful new construction on a full acre featuring 4 bedrooms and 3.5 baths with high-end finishes throughout. The open-concept main living area showcases a stunning 20’ cathedral ceiling and flows into a designer kitchen with quartz countertops, custom cabinetry, an oversized 8’ island, and a walk-in pantry with butcher block shelving. The spacious primary suite offers a tiled shower and floor

    Anna Boyer Howard Hanna Real Estate Svcs.

    14002 Old Suffolk Rd, Windsor, VA 23487
  • /50

    $589,990 New Construction

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

    MM Windsor Station (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

    Lori Cutrell BHHS RW Towne Realty

    MM Windsor Station (Roanoke), Windsor, VA 23487
  • /46

    $499,990 New Construction

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

    MM Windsor Station (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

    Lori Cutrell BHHS RW Towne Realty

    MM Windsor Station (Caldwell), Windsor, VA 23487
  • /50

    $574,990 New Construction

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

    MM Windsor Station (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

    Lori Cutrell BHHS RW Towne Realty

    MM Windsor Station (McDowell), 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
  • /32

    $354,999 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,480 Sq Ft

    105 S Court St, Windsor, VA 23487

    New construction with premium upgrades by an award-winning builder-move-in ready and built to impress! This modern home offers spacious open living, upgraded LVP flooring, elegant granite countertops, and upgraded cabinetry throughout. The upgraded windows and spray foam insulation make for a calm home! A designer lighting package enhances the bright, airy feel of every room. Conveniently located

    Ralph Harvey ListWithFreedom.com Inc

    105 S Court St, Windsor, VA 23487
  • /49

    $499,000

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

    17314 Jolly Cir, Windsor, VA 23487

    Tucked away on 2.57 beautiful acres, this one-of-a-kind property offers the perfect blend of space, charm, and functionality. With over 2,500 square feet of living space, the home features 4 bedrooms and 3 full baths, including a convenient first-floor primary suite. Gorgeous hardwood floors run throughout, and the home is filled with character and unique details you just don’t find in newer

    Anna Boyer Howard Hanna Real Estate Svcs.

    17314 Jolly Cir, Windsor, VA 23487
  • /23

    $299,900

    • 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
  • /37

    $325,000

    • 3 Beds
    • 2.5 Baths
    • 1,600 Sq Ft

    24456 Walters Hwy, Windsor, VA 23487

    Nice 3 Bedroom, 2.5 Bath home on large corner lot. Stainless Steel Side by Side Refrigerator, Stainless Steel Range and Dishwasher. 2 car attached garage, Privacy Fenced backyard, Deck. Zoned HVAC. Convenient location for schools, employment, shopping and commuting.

    S Dane Scott Scott & Assoc. Inc. Realtors

    24456 Walters Hwy, Windsor, VA 23487
  • /50

    $464,999

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

    25253 Kelsie St, Windsor, VA 23487

    Beautiful home located in a sought-after Windsor neighborhood, set on a private wooded lot with a spacious backyard ideal for relaxing and entertaining. This well-designed home offers 5 bedrooms and 3 full baths, providing space and flexibility for today’s lifestyle. The main level features wood flooring and abundant natural light. The kitchen includes a large center island, quartz countertops,

    Charles Nash EXP Realty LLC

    25253 Kelsie St, Windsor, VA 23487
  • /50

    $579,990 New Construction

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

    MM Windsor Station (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

    Lori Cutrell BHHS RW Towne Realty

    MM Windsor Station (Charleston), Windsor, VA 23487
  • /28

    $420,000

    • 3 Beds
    • 2 Baths
    • 1,754 Sq Ft

    24347 Lovers Ln, Windsor, VA 23487

    Welcome to easy, one-level living in the heart of Windsor! This well-maintained brick ranch offers 3 bedrooms and 2 full baths on a spacious 0.43-acre lot. Inside, you’ll find a comfortable layout with plenty of natural light, a functional kitchen, and cozy living spaces great for everyday life or hosting friends and family. The large yard gives you room to spread out—whether it’s adding a garden

    Hillary Kaufman 1st Class RE Barn Door Homes

    24347 Lovers Ln, Windsor, VA 23487
  • /13

    $214,999

    • 3 Beds
    • 1 Bath
    • 1,104 Sq Ft

    17036 N Carolina Ave, Windsor, VA 23487

    Quiet Country Living with Modern Comforts Enjoy peaceful country living in this well-maintained home featuring a spacious open floor plan designed for comfortable everyday living and easy entertaining. Updated windows and HVAC provide energy efficiency and year-round comfort. This home offers 3 bedrooms plus a flexible office that can serve as a 4th bedroom, guest room, or hobby space. The full

    Robert Thompson EXP Realty LLC

    17036 N Carolina Ave, 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.

Home Trends in Windsor, VA

Housing Trends

Median Sale Price
$398,750
Median Single Family Sale Price
$447,250
Average Price Per Sq Ft
$204
Number of Homes for Sale
32
Last 12 months Home Sales
58
Months of Supply
6.60
Median List Price
$437,450
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
40%
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