2,717

Windsor, VA Homes

Section Image Section Image Section Image
  • /8

    $999,000 Pending

    • 4 Beds
    • 2.5 Baths
    • 2,374 Sq Ft

    18101 Foxfire Trail, Windsor, VA 23487

    WELCOME HOME! This home boasts all of the luxury and space you could ever dream of, all while being on 21+ acres of your own wooded paradise. Aspen Barndo

    Agent Photo

    Rachel Beasley

    Shoreline Realty

    (757) 267-6687

    18101 Foxfire Trail, Windsor, VA 23487
  • /5

    $1,200 per month

    • 1 Bed
    • 1 Bath
    • 1,500 Sq Ft
    • Condo for Rent

    18059 Foxfire Trail, Windsor, VA 23487

    Property Id: 1260993If you like to live in the country with nature around, this is the home for you. This finished apartment over a 3-car garage (FROG) is extremely private, modern with a beautiful landscape. The home itself is more than 1,500 square feet, clean, with open floor plan that offers plenty of sunlight, in a quiet, safe neighborhood in Isle of Wight County, Windsor, VA. Only

    18059 Foxfire Trail, Windsor, VA 23487
  • 8561 Peanut Dr, Windsor, VA 23487

    $540,000 Sold Aug 18, 2025

    8561 Peanut Dr, Windsor, VA 23487

    • 4 Beds
    • 2.5 Baths
    • 3,165 Sq Ft
    • Built 1985

    Last Sold Summary

    • $171/SF
    • 8 Days On Market

    Current Estimated Value $542,809

    Last Listing Agent Jimmy Auvil 1st Advantage Realty LLC

    8561 Peanut Dr, Windsor, VA 23487
    • /20

      Est $454,655 Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 2,656 Sq Ft

      10431 Sylvia Cir, Windsor, VA 23487

      10431 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
  • 46 N Court St, Windsor, VA 23487

    $197,000 Sold Apr 04, 2025

    46 N Court St, Windsor, VA 23487

    • 3 Beds
    • 1 Bath
    • 1,670 Sq Ft
    • Built 1945

    Last Sold Summary

    • $118/SF
    • 14 Days On Market

    Current Estimated Value $226,158

    Last Listing Agent Kimberly Harrah 1st Class RE Coastal Breeze

    46 N Court St, Windsor, VA 23487
    • /25

      Est $177,342 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 900 Sq Ft

      11161 Old Suffolk Rd, Windsor, VA 23487

      11161 Old Suffolk Rd, 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
  • 4 Watson St, Windsor, VA 23487

    $330,000 Sold Mar 27, 2025

    4 Watson St, Windsor, VA 23487

    • 4 Beds
    • 2 Baths
    • 1,476 Sq Ft
    • Built 1956

    Last Sold Summary

    • $224/SF
    • 44 Days On Market

    Current Estimated Value $327,406

    Last Listing Agent Lisa Barber RE/MAX Country to Coast

    4 Watson St, Windsor, VA 23487
    • /2

      Est $208,048 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 960 Sq Ft

      13540 Bowling Green Rd, Windsor, VA 23487

      13540 Bowling Green Rd, 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
  • /3

    $150,000 Sold Nov 13, 2025

    66 Church St, Windsor, VA 23487

    • Land
    • 25.81 Acres
    • $5,812 per Acre

    Last Sold Summary

    • 25% Below List Price
    • 178 Days On Market

    Current Estimated Value $165,437

    Last Listing Agent Jim MARTIN Acker Real Estate Service

    66 Church St, Windsor, VA 23487
    • /36

      Est $291,366 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,424 Sq Ft

      8747 Fire Tower Rd, Windsor, VA 23487

      8747 Fire Tower Rd, 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
  • 216 Robinson Way, Windsor, VA 23487

    $610,000 Sold Jun 30, 2025

    216 Robinson Way, Windsor, VA 23487

    • 5 Beds
    • 2.5 Baths
    • 3,529 Sq Ft
    • Built 1996

    Last Sold Summary

    • $173/SF
    • 29 Days On Market

    Current Estimated Value $618,512

    Last Listing Agent Jay Hassell Keller Williams Realty Twn Ctr

    216 Robinson Way, Windsor, VA 23487
    • /45

      Est $1,967,472 Not Listed For Sale

      • 5 Beds
      • 6 Baths
      • 6,369 Sq Ft

      24073 Lawrence Haven Ln, Windsor, VA 23487

      24073 Lawrence Haven 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
  • 67 E Windsor Blvd, Windsor, VA 23487

    $299,900 Sold Sep 26, 2025

    67 E Windsor Blvd, Windsor, VA 23487

    • 3 Beds
    • 1 Bath
    • 1,313 Sq Ft
    • Built 1969

    Last Sold Summary

    • $228/SF
    • 27 Days On Market

    Current Estimated Value $299,443

    Last Listing Agent Lacey Whitaker Iron Valley Real Estate HR

    67 E Windsor Blvd, Windsor, VA 23487
    • /23

      Est $452,156 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,400 Sq Ft

      13505 Shiloh Dr, Windsor, VA 23487

      13505 Shiloh Dr, 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
  • 48.8ac Murphy Mill Rd, Windsor, VA 23487

    $750,000 Sold Jul 11, 2025

    48.8ac Murphy Mill Rd, Windsor, VA 23487

    • Land
    • 48.8 Acres
    • $15,369 per Acre

    Last Sold Summary

    • 10% Below List Price
    • 377 Days On Market

    Last Listing Agent Caleb Hooker MOP Land and Farms Realty

    48.8ac Murphy Mill Rd, Windsor, VA 23487
    • /2

      Est $437,968 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,156 Sq Ft

      18223 Pope Swamp Trail, Windsor, VA 23487

      18223 Pope Swamp Trail, 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
  • 10419 Sylvia Cir, Windsor, VA 23487

    $410,000 Sold Jan 23, 2026

    10419 Sylvia Cir, Windsor, VA 23487

    • 3 Beds
    • 2 Baths
    • 2,141 Sq Ft
    • Built 2005

    Last Sold Summary

    • $191/SF
    • 12 Days On Market

    Last Listing Agent Connie Melton Iron Valley Real Est Norfolk

    10419 Sylvia Cir, Windsor, VA 23487
    • /130

      Est $1,967,472 Not Listed For Sale

      • 5 Beds
      • 6 Baths
      • 6,369 Sq Ft

      24073 Lawrence Haven Ln, Windsor, VA 23487

      24073 Lawrence Haven Ln, 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
  • 203 Hidden Acres Cir, Windsor, VA 23487

    $357,900 Sold Sep 15, 2025

    203 Hidden Acres Cir, Windsor, VA 23487

    • 3 Beds
    • 2 Baths
    • 1,715 Sq Ft
    • Built 1990

    Last Sold Summary

    • $209/SF
    • 0 Days On Market

    Current Estimated Value $360,489

    Last Listing Agent Ellen Drames BHHS RW Towne Realty

    203 Hidden Acres Cir, Windsor, VA 23487
    • /17

      Not Listed For Sale

      00 Walter Hwy - Hwy 258 Hwy S, Windsor, VA 23487

      00 Walter Hwy - Hwy 258 Hwy S, 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
  • 24441 Lovers Ln, Windsor, VA 23487

    $400,000 Sold Nov 14, 2025

    24441 Lovers Ln, Windsor, VA 23487

    • 3 Beds
    • 2 Baths
    • 2,000 Sq Ft
    • Built 1977

    Last Sold Summary

    • $200/SF
    • 9 Days On Market

    Current Estimated Value $398,500

    Last Listing Agent Diane Pearman The Real Estate Group

    24441 Lovers Ln, Windsor, VA 23487
    • /17

      Not Listed For Sale

      00 Walters Hwy, Windsor, VA 23487

      00 Walters Hwy, Windsor, VA 23487
  • /39

    $509,990 New Construction

    • 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
  • 11397 Shiloh Dr, Windsor, VA 23487

    $510,000 Sold Nov 10, 2025

    11397 Shiloh Dr, Windsor, VA 23487

    • 4 Beds
    • 2.5 Baths
    • 2,300 Sq Ft
    • Built 2009

    Last Sold Summary

    • $222/SF
    • 5 Days On Market

    Current Estimated Value $503,170

    Last Listing Agent April Partida RE/MAX Alliance

    11397 Shiloh Dr, Windsor, VA 23487
    • /10

      Est $358,640 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,454 Sq Ft

      24125 Butler Ave, Windsor, VA 23487

      24125 Butler Ave, 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

    Amanda Reyes BHHS RW Towne Realty

    MM Windsor Station (Drexel), Windsor, VA 23487
  • 24465 Curve Dr, Windsor, VA 23487

    $178,000 Sold Dec 15, 2025

    24465 Curve Dr, Windsor, VA 23487

    • 3 Beds
    • 1.5 Baths
    • 926 Sq Ft
    • Built 1955

    Last Sold Summary

    • $192/SF
    • 103 Days On Market

    Last Listing Agent Dale Scott Scott & Assoc. Inc. Realtors

    24465 Curve Dr, Windsor, VA 23487
    • /2

      Est $289,441 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,375 Sq Ft

      16 Roberts Ave, Windsor, VA 23487

      16 Roberts Ave, 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
  • 16196 Quaker Pointe, Windsor, VA 23487

    $916,650 Sold Aug 20, 2025

    16196 Quaker Pointe, Windsor, VA 23487

    • 4 Beds
    • 2.5 Baths
    • 4,100 Sq Ft
    • Built 2008

    Last Sold Summary

    • $224/SF
    • 7 Days On Market

    Current Estimated Value $906,619

    Last Listing Agent Stacy Ryan Howard Hanna Real Estate Svcs.

    16196 Quaker Pointe, Windsor, VA 23487
    • /2

      Est $347,012 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,713 Sq Ft

      9 Holland Dr, Windsor, VA 23487

      9 Holland Dr, Windsor, VA 23487

Showing Results 1 - 40, Page 1 of 18

Home Trends in Windsor, VA

Housing Trends

Median Sale Price
$405,000
Median Single Family Sale Price
$449,750
Average Price Per Sq Ft
$205
Number of Homes for Sale
28
Last 12 months Home Sales
51
Months of Supply
6.60
Median List Price
$445,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
42%
How to Buy a Home How to Finance a Home How to Sell a Home