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Windsor, VA Houses for Sale

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  • /30

    $588,900

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 2,342 Sq Ft

    47AC Holland Dr, Windsor, VA 23487

    WELCOME TO THE MAYFIELD, ANOTHER FABULOUS HOME FROM SUFFOLK & ISLE OF WIGHTS PREMIER CUSTOM BUILDER. THIS 4 BEDROOM, 2 1/2 BATH HOME IS LOADED WITH THE BUILDERS STANDARD FEATURES, WHICH MOST BUILDERS WOULD CONSIDER UPGRADES. FROM THE INVITING FRONT PORCH TO THE LARGE GREAT ROOM WITH VAULTED CEILINGS, THIS HOME IS MAGNIFICENT. IF YOU ARE LOOKING FOR AN OPEN CONCEPT PLAN WITH LARGE SPACES THAT MAKE

    Agent Photo

    Dan Lawson

    Green Tree Real Estate Inc

    (757) 906-3997

    47AC Holland Dr, Windsor, VA 23487
  • /6

    $499,900

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,979 Sq Ft

    MM Kestrel (Ranch) Windsor Station, Windsor, VA 23487

    Welcome to the NEW Kestrel Ranch Model in Windsor Station, which combines country-style living, spacious lots and nearby amenities of Suffolk! Pick your lot and exterior elevation to start your Dream Home with this 3 BR, 2.5 BA ranch, and customize up to 4 BRs, 3.5 BAs with Loft and back porch. 2 BRs with a Full BA are located separate from the Primary Suite. Open concept Kitchen/Family/Dining

    Jamie Roser Wainwright Real Estate

    MM Kestrel (Ranch) Windsor Station, 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
  • /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
  • /41

    $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
  • /27

    $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
  • /24

    $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
  • /38

    $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 NOW!! 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
  • /18

    $572,000

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 2,311 Sq Ft

    12236 Ava Ln, Windsor, VA 23487

    Welcome to Windsor Station! This stunning Halena model will be move-in ready this July and showcases beautiful Craftsman-style details from the exterior through every inch of the home. Inside, you’ll find durable LVP flooring throughout the main living areas and a thoughtfully designed layout featuring 4 bedrooms, including a spacious primary suite with a tile shower and walk-in closets. The

    Christopher Kostyrka RE/MAX Connect

    12236 Ava Ln, Windsor, VA 23487
  • /39

    $509,990

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 2,449 Sq Ft

    MM Raleigh, Windsor, VA 23487

    Discover luxury living in The Raleigh by Eastwood Homes at Windsor Station, a stunning two-story home designed for comfort and style. This spacious plan features four bedrooms and a sought-after first-floor primary suite for added convenience. The main level is ideal for entertaining, with a formal dining room and dramatic two-story family room flowing into a chef-inspired kitchen. Upstairs, a

    Lori Cutrell BHHS RW Towne Realty

    MM Raleigh, Windsor, VA 23487
  • /50

    $574,990

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

    MM Mcdowell, Windsor, VA 23487

    Welcome to The McDowell by Eastwood Homes at Windsor Station, a stunning two-story home designed for comfort, space, and modern living. This four-bedroom, 3.5-bath layout features a sought-after first-floor primary suite, elegant formal dining room, and a dramatic two-story family room that flows into a chef-inspired kitchen with island, pantry, and bright breakfast area perfect for everyday

    Lori Cutrell BHHS RW Towne Realty

    MM Mcdowell, Windsor, VA 23487
  • /23

    $265,900

    • 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
  • /39

    $544,990

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

    MM Davidson, Windsor, VA 23487

    Enter into The Davidson by Eastwood Homes at Windsor Station, a beautifully designed two-story home where space, comfort, and connection come together. With five bedrooms and three full baths, this inviting layout features elegant formal living and dining rooms, a bright, open kitchen with island, pantry, and breakfast area, and a spacious family room perfect for gathering and making memories. A

    Lori Cutrell BHHS RW Towne Realty

    MM Davidson, Windsor, VA 23487
  • /46

    $499,990

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

    MM Caldwell, Windsor, VA 23487

    Experience effortless living in The Caldwell by Eastwood Homes at Windsor Station, a beautifully designed ranch-style home offering comfort, flexibility, and modern convenience. This thoughtfully crafted floor plan features three spacious bedrooms, two full baths, and a first-floor primary suite with dual closets for added storage. Enjoy a bright, open layout with a formal dining room, expansive

    Lori Cutrell BHHS RW Towne Realty

    MM Caldwell, Windsor, VA 23487
  • /18

    $583,800

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 2,650 Sq Ft

    12177 Ava Ln, Windsor, VA 23487

    Welcome to Windsor Station! This stunning Oakville model will be move-in ready this August and showcases beautiful Craftsman-style details from the exterior through every inch of the home. Inside, you’ll find durable LVP flooring throughout the main living areas and a thoughtfully designed layout featuring 4 bedrooms, including a spacious primary suite with a tile shower and walk-in closets. The

    Wyndy Woods RE/MAX Connect

    12177 Ava Ln, Windsor, VA 23487
  • /34

    $270,000

    • 2 Beds
    • 1 Bath
    • 1,086 Sq Ft

    9545 Windsor Blvd, Windsor, VA 23487

    Charming rancher on almost 5 acres of land! This cute home features a completely freshly painted interior, beautifully refinished hardwoods, and brand-new LVP flooring in the kitchen and bathroom. The well-sized kitchen boasts ample counter space, plenty of room for dining, and opens seamlessly to both the living room and the side yard. Directly off the living room, you will find a versatile

    Drew Cheely Joyner Fine Properties

    9545 Windsor Blvd, 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
  • /50

    $589,990

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

    MM Roanoke, Windsor, VA 23487

    Welcome to The Roanoke by Eastwood Homes at Windsor Station, a beautifully designed two-story home where style, comfort, and modern living come together. This four-bedroom, three-bath layout features an open-concept design with a spacious family room that flows effortlessly into a chef inspired kitchen with an expansive island, granite countertops, and smartly crafted cabinetry. Perfect for

    Lori Cutrell BHHS RW Towne Realty

    MM Roanoke, 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, only finishing touches remain!! 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

    Jamie Roser Wainwright Real Estate

    11563 Savannah St, Windsor, VA 23487
  • /46

    $589,990

    New Construction $9K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,201 Sq Ft

    12199 Ava Ln, Windsor, VA 23487

    Move in Ready-Quick Close for this Stunning Asheboro Ranch floorplan at Windsor Station! Features a 1st-floor primary retreat, formal dining, and a gourmet kitchen with Quartz counter tops and island. LVP and extensive trim package in main living areas. Perfect layout: Jack & Jill bath serves bedrooms 2/3, while the upstairs loft and 4th bedroom offer the perfect getaway. Space for everyone!

    Lori Cutrell BHHS RW Towne Realty

    12199 Ava Ln, Windsor, VA 23487
  • /50

    $650,000

    • 5 Beds
    • 5 Baths
    • 3,868 Sq Ft

    18517 Shady Pine Ln, Windsor, VA 23487

    Escape to your own private 14.84-Acre wooded retreat in Windsor! Discover ultimate privacy and timeless charm in this 5-bedroom, 5-bath Cape Cod Farmhouse. Nestled on 14.84 beautifully wooded acres, this estate blends grand architecture with cozy, functional living. The heart of the home features an open living room boasting vaulted ceilings and a dramatic two-story fireplace that flows

    Lori Bauer Long & Foster Real Estate Inc.

    18517 Shady Pine Ln, 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
  • /21

    $539,990

    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
  • /48

    $615,000

    $10K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,567 Sq Ft

    25092 Tyler Dr, Windsor, VA 23487

    3 bed 2.5 bath brick home, wooded 4.71 ac lot. 2 car attached garage. Large, detached 2 story garage. Geo-thermal system keeps utilities low. System installed 1994. Unit replaced last year. New deck. Mud room, study, half bath off of kitchen. Kitchen opens to huge dining/great room with fireplace. Large sunroom on back of home. Front door foyer. Above garage finished rooms. Large enough for

    Tracy Pudder World Class Realty

    25092 Tyler Dr, Windsor, VA 23487
  • /44

    $375,000

    • 4 Beds
    • 2 Baths
    • 1,955 Sq Ft

    26 N Court St, Windsor, VA 23487

    Looking for more land, a house with charm and plenty of space for entertaining? Well - look no further! This 4 bedroom property has all of that and more! On just under an acre of land, the whimsy of this house, coupled with the thoughtful updates throughout, make this the perfect place to call home. Freshly painted, new refrigerator, new dishwasher, and curated updates, all you have to do is

    Margo Savage A Better Way Realty Inc.

    26 N Court St, Windsor, VA 23487
  • /18

    $549,000

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 2,311 Sq Ft

    11564 Savannah St, Windsor, VA 23487

    Welcome to Windsor Station! This stunning Halena model, elevation B,will be move-in ready this August and showcases beautiful Craftsman-style details from the exterior through every inch of the home. Inside, you’ll find durable LVP flooring throughout the main living areas and a thoughtfully designed layout featuring 4 bedrooms, including a spacious primary suite with a tile shower and walk-in

    Christopher Kostyrka RE/MAX Connect

    11564 Savannah St, Windsor, VA 23487
  • /50

    $459,999

    $5K PRICE DROP
    • 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
  • /32

    $519,990

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

    MM 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 Drexel, Windsor, VA 23487
  • /50

    $579,990

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

    MM Charleston, Windsor, VA 23487

    Discover The Charleston by Eastwood Homes at Windsor Station, a stunning two-story home designed for elevated living, comfort, and versatility. This spacious five-bedroom, three-bath layout features elegant formal living and dining rooms, a dramatic two-story family room, and an open kitchen with island and pantry perfect for entertaining and everyday moments. A first-floor guest suite with full

    Lori Cutrell 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
  • /27

    $514,990

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

    MM Cypress (Windsor Station), Windsor, VA 23487

    Discover The Cypress by Eastwood Homes at Windsor Station, where modern elegance meets timeless charm. This beautifully designed four-bedroom, three-bath home features a flexible first-floor guest suite and a well-appointed kitchen with a large island and walk-in pantry perfect for entertaining and everyday living. Upstairs, enjoy an expansive loft for a media room or play space, along with a

    Lori Cutrell BHHS RW Towne Realty

    MM Cypress (Windsor Station), Windsor, VA 23487
  • /37

    $534,990

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

    MM Asheboro, Windsor, VA 23487

    Discover The Asheboro by Eastwood Homes at Windsor Station, a thoughtfully designed home that blends comfort, style, and modern convenience. This three-bedroom, 2.5-bath ranch features a desirable split floor plan, with the first-floor primary suite positioned away from the secondary bedrooms for added peace and relaxation. The home also offers a formal dining room, spacious great room, and an

    Lori Cutrell BHHS RW Towne Realty

    MM Asheboro, Windsor, VA 23487
  • /34

    $450,000

    • 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

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.

Single Family Home Prices in Windsor, VA

Single Family Home Price Trends

Median Home Price
$450,000
Median 3-Bedroom Home Price
$387,449
Median 4-Bedroom Home Price
$517,490
Median 5-Bedroom Home Price
$544,990
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