Windsor, VA Homes

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  $550,000

  • 3 Beds
  • 2.5 Baths
  • 1,742 Sq Ft

  9161 Whispering Pines Trail, Windsor, VA 23487

  Nestled in Isle of Wight County, Virginia, this 5.37-acre homestead is a serene escape, just 15 minutes from Smithfield and Windsor, with quick access to both US Route 460 and Route 17. The 1,742 sq ft log home boasts a first-floor primary bedroom with ensuite, an open living/dining area with a cozy fireplace and vaulted ceiling, a galley kitchen with ample pantry space, a utility room, and a

  

  Caleb Hooker

  Mossy Oak Properties/Land and Farms Realty

  (757) 551-3117

  9161 Whispering Pines Trail, Windsor, VA 23487
• Explore Windsor

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  $1,700 per month

  • 3 Beds
  • 2 Baths
  • 2,460 Sq Ft
  • House for Rent

  23 E Griffin St, Windsor, VA 23487

  Well Maintained Home on Nicely Landscaped Lot. 2 Car Detached Garage and Paved Driveway. Nice Sun Porch & Covered Patio. Outbuildings. Replacement Windows. All Showings Require Application With Income Verification For Pre-Qualification Prior to Scheduling.

  Dale Scott Scott & Assoc. Inc. Realtors

  23 E Griffin St, Windsor, VA 23487
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  $357,900 Sold Sep 15, 2025

  • 1,715 Sq Ft
  • $209/SF
  • 0 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1990

  203 Hidden Acres Cir, Windsor, VA 23487

  Classic Brick Ranch in the Heart of Windsor, Spacious & welcoming, this brick ranch offers approximately 1,800 Sq Ft. of comfortable living Featuring 3 bedrooms, 2 bathrooms, family room w/fireplace, formal dining room, & an eat-in kitchen, it's a wonderful blend of traditional style and practical layout.Set on a large half-acre lot, the home provides plenty of space indoors and out, great

  Ellen Drames BHHS RW Towne Realty

  203 Hidden Acres Cir, Windsor, VA 23487
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  Est $449,849 Not Listed For Sale

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

  13505 Shiloh Dr, Windsor, VA 23487

  13505 Shiloh Dr, Windsor, VA 23487
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  $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

  

  Rachel Beasley

  Own Real Estate LLC

  (757) 267-6687

  18101 Foxfire Trail, Windsor, VA 23487
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  $374,800 Sold Aug 15, 2025

  • 2,800 Sq Ft
  • $134/SF
  • 64 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1900

  39 Bank St, Windsor, VA 23487

  This beautifully renovated 2,800 sq. ft. home on 2.30 acres in the heart of Windsor is truly a must-see! Taken down to the studs & completely rebuilt, everything is NEW—roof, siding, windows, HVAC, plumbing, lighting, drywall, & flooring. The spacious layout offers a FIRST FLOOR primary suite with a full bath, a large living room, a cozy den, & a mudroom for added convenience. The stunning

  Rachel Beasley Own Real Estate LLC

  39 Bank St, Windsor, VA 23487
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  Est $219,553 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,088 Sq Ft

  7 Community Dr, Windsor, VA 23487

  7 Community Dr, Windsor, VA 23487
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  $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
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  $405,000 Sold Jul 28, 2025

  • 2,050 Sq Ft
  • $198/SF
  • 11 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2002

  22480 York Ct, Windsor, VA 23487

  Welcome to Windsor Woods! This charming 3-bedroom, 2-bath home sits on a spacious corner lot with no HOA. Inside you'll find an open-concept living, dining, and kitchen area, perfect for entertaining. The large FROG offers flexible space for a guest room, playroom, or office. The primary suite features an updated ensuite bath, walk-in closet, and bonus nook ideal for a home office or workout

  Anna Boyer Howard Hanna Real Estate Services

  22480 York Ct, Windsor, VA 23487
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  Est $250,235 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
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  $479,900

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

  24192 Twin Cir, Windsor, VA 23487

  You don't want to miss this unique property and all it offers! This property includes a warm and welcoming main home, 26x60 detached garage workshop w/ bathroom and attached mother in law apartment all on its own electric meter. Main home has an open floor plan and features family room w large wood burning fp, wood beams, dining area, 3/4 in. beautiful Australian cypress hardwood floors

  Julie d Crist RE/MAX Capital

  24192 Twin Cir, Windsor, VA 23487
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  $750,000 Sold Jul 11, 2025

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

  • 377 Days On Market

  48.8ac Murphy Mill Rd, Windsor, VA 23487

  This beautiful 48.8 acres of waterfront property along Lake Burnt Mills in Isle of Wight County is waiting for your new dream home or retreat! The property is being offered for purchase in its entirety or the opportunity to purchase one of the two 24+/- acre parcels preliminary approved for subdivision. The property features over 5000 feet of lakefront along Lake Burnt Mills. This beautiful

  Caleb Hooker Mossy Oak Properties/Land and Farms Realty

  48.8ac Murphy Mill Rd, Windsor, VA 23487
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  Est $421,267 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
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  $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
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  $449,500 Sold Jul 07, 2025

  • 2,296 Sq Ft
  • $196/SF
  • 23 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1959

  10421 Central Hill Rd, Windsor, VA 23487

  Embrace the tranquility of country living in this beautifully maintained brick ranch, set on nearly 3 acres of land. This spacious home offers 4 bedrooms, 2.5 baths, and 2,296 square feet of comfortable living space. The large living room is perfect for relaxing or entertaining, while the updated kitchen (renovated in 2019) featuring a double oven—makes cooking a joy. Step outside to the

  Anna Boyer Howard Hanna Real Estate Services

  10421 Central Hill Rd, Windsor, VA 23487
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  Est $297,350 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
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  $525,000 Pending

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

  11397 Shiloh Dr, Windsor, VA 23487

  Totally refreshed and updated. Sparkling in ground pool, large deck. Room to park all the fun stuff. Better than new and at an amazing price!

  April Partida RE/MAX Alliance

  11397 Shiloh Dr, Windsor, VA 23487
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  $459,900 Sold Jun 30, 2025

  • 2,774 Sq Ft
  • $166/SF
  • 7 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1993

  213 Robinson Way, Windsor, VA 23487

  Discover this well-appointed 4-bedroom, 2.5-bath home in the sought-after Hidden Acres neighborhood of Windsor. Boasting a spacious and functional layout, the home features a large living room, dining room, and a comfortable family room—fantastic for both everyday living and entertaining. You will also find a spacious kitchen with plenty of counter and storage space, great for preparing meals and

  Dayana Cervantes Thrive Realty

  213 Robinson Way, Windsor, VA 23487
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  Est $1,081,204 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
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  $435,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,876 Sq Ft

  32 N Court St, Windsor, VA 23487

  DO NOT LET THIS OPPORTUNITY GET AWAY! This home has LOTS of potential to customize and make it personal for your taste. This is a well built home with steel beam under the home and lots of quality! 4 Bedroom BRICK Colonial with 2 car attached brick carport, copper gutters, large yard and deck etc. on the exterior and Large kitchen, lots of cabinets, eat in area, utility room, hardwood floors,

  S Dane Scott Scott & Assoc. Inc. Realtors

  32 N Court St, Windsor, VA 23487
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  $590,000 Sold Jun 26, 2025

  • 1,760 Sq Ft
  • $335/SF
  • 269 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2024

  15338 Everets Rd, Windsor, VA 23487

  Welcome home to your charming Isle of Wight farmhouse. Built in 2023, you will find the convenience of today and simplicity of years gone by. This nature lover's paradise is awaiting you to explore over 10 acres. Keep your hay dry in the 20 x 40 metal barn. Come inside to feel the warmth of the wood burning fireplace. The open floor plan is designed for sharing meals, laughter and unforgettable

  Melissa Boyce EXP Realty LLC

  15338 Everets Rd, Windsor, VA 23487
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  Est $1,081,204 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
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  $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
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  $397,500 Sold Jun 13, 2025

  • 1,986 Sq Ft
  • $200/SF
  • 88 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2020

  12005 Lena Rose St, Windsor, VA 23487

  Discover the perfect blend of modern convenience and small-town charm in this newer-built 4-bed, 2.5-bath home. If you're looking for a move-in-ready home—this is it! With a relaxed HOA, you can store your RV or boat at home, and no storage fees. The oversized driveway ensures ample parking for all your vehicles. The kitchen flows seamlessly into the living and dining areas, creating an

  Amanda Emanuel BHHS RW Towne Realty

  12005 Lena Rose St, Windsor, VA 23487
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  Not Listed For Sale

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

  00 Walter Hwy - Hwy 258 Hwy S, Windsor, VA 23487
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  $239,900

  • 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
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  $415,000 Sold Jun 13, 2025

  • 2,323 Sq Ft
  • $179/SF
  • 106 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2005

  12296 Keaton Ave, Windsor, VA 23487

  This beautiful home sits on an elevated, private lot in a quiet neighborhood located in the Town of Windsor. This property features a nice front porch and a rear patio for relaxing. Conveniently located near Hwy 460 and minutes away from Hwy 58. Do not let this rare purchase opportunity get away!

  Durwood Scott Scott & Assoc. Inc. Realtors

  12296 Keaton Ave, Windsor, VA 23487
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  Not Listed For Sale

  00 Walters Hwy, Windsor, VA 23487

  00 Walters Hwy, Windsor, VA 23487
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  $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
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  $299,000 Sold Jun 03, 2025

  • 1,188 Sq Ft
  • $252/SF
  • 10 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1963

  23081 Courthouse Hwy, Windsor, VA 23487

  Move-in ready and full of charm! This spacious home features 3 bedrooms, 2 full baths, and a smart split floor plan with the private primary suite on one side and additional bedrooms on the other. A flexible bonus room off the kitchen is perfect as a dining area, mudroom, office, or playroom. Enjoy peaceful mornings on the large front porch and host gatherings on the expansive back deck. Sitting

  Morgan Wood Liz Moore & Associates LLC

  23081 Courthouse Hwy, Windsor, VA 23487
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  Est $202,764 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 400,792 Sq Ft

  12 Community Dr, Windsor, VA 23487

  12 Community Dr, Windsor, VA 23487
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  $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
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  $465,000 Sold May 01, 2025

  • 1,980 Sq Ft
  • $235/SF
  • 60 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2012

  17214 Woodland Dr, Windsor, VA 23487

  Welcome to your Dream Home In Windsor Your personal oasis awaits, nestled on five acres yet only ten minutes to town. Relax on your 20ft x 6 deep front porch, enjoy your thoughtfully renovated open concept floorpan, kitchen with new quartz countertops, updated cabinets and large center island with room for multiple barstools.Spacious laundry for all your storage/laundry needs.Split bedroom

  Tammy Glover Fathom Realty

  17214 Woodland Dr, Windsor, VA 23487
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  Est $335,279 Not Listed For Sale

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

  24125 Butler Ave, Windsor, VA 23487

  24125 Butler Ave, Windsor, VA 23487
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  /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
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  $197,000 Sold Apr 04, 2025

  • 1,670 Sq Ft
  • $118/SF
  • 14 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1945

  46 N Court St, Windsor, VA 23487

  Investor Special or Buyer wanting sweat equity! This 1 story located on approx .5 acre lot home has 1640 sf, 3 bedrooms, 1 bath, Great room, Living room, eat in kitchen, spare room or office, laundry/pantry closet, side patio, 360sf detached garage and fenced rear yard. Great opportunity to live in the country and make this home your own. Home is being sold "as is".

  Kimberly Harrah 1st Class Real Estate Coastal Breeze

  46 N Court St, Windsor, VA 23487
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  Est $283,670 Not Listed For Sale

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

  16 Roberts Ave, Windsor, VA 23487

  16 Roberts Ave, Windsor, VA 23487
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  $344,000

  • 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
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  $429,900 Sold Mar 11, 2025

  • 2,808 Sq Ft
  • $153/SF
  • 35 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 2021

  12001 Lena Rose St, Windsor, VA 23487

  Welcome to your dream home nestled in a highly sought-after neighborhood. This stunning home sits on 0.43 ac lot, providing space for outdoor activities and relaxation in a completely fenced backyard. Freshly painted throughout , this property features an open floor plan that's great for entertaining and daily family life. With 5 BR and 3 BA, including a bedroom and bath on the first floor, this

  Candace Saunders 1st Class Real Estate Riverside

  12001 Lena Rose St, Windsor, VA 23487
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  /2

  Est $317,074 Not Listed For Sale

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

  9 Holland Dr, Windsor, VA 23487

  9 Holland Dr, Windsor, VA 23487

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