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$1,025,000
3 Beds ⋅ 3.1 Baths ⋅ 10607506 MLS
12-acres of exceptional beauty and privacy features a welcoming picket fence and crepe myrtles entrance. The driveway is flanked by scenic cotton fields leading to a picturesque 3-acre pond, fully stocked with fish! Custom all-brick home showcases mature trees, a peaceful setting, and spacious back porch w/ fans extending across the rear of the house overlooking the pond. Spacious entertaining patio and wood-burning fireplace creates a most relaxing ambiance. The property consists of 11 acres +1 adjoining acre. Impressive brick home welcomes guests with charming front porch, elegant foyer and complemented by extensive millwork and hdwd flrs throughout. The gourmet kitchen w/ black granite countertops has soft-close drawers and opens seamlessly into family room and dining room. 1st floor primary en-suite features marble backsplash and counter. Additional highlights include oversized 2-car detached garage /w office and storage, whole-house generator, geo-thermal H/A, and security system.

15023 Five Forks Road, Windsor
$694,258
5 Beds ⋅ 5 Baths ⋅ 10629562 MLS
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 ideal 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 office. Upstairs includes a generous loft, convenient laundry room, and a luxurious primary suite with dual vanities, a walk-in closet, and a tile shower. Enjoy small-town charm in Windsor with quick access to Route 460, shops, and dining. Thoughtfully crafted for comfort, style, and energy efficiency? This home truly has it all!

24248 Liam Court, Windsor
$675,000
4 Beds ⋅ 3.1 Baths ⋅ 10630267 MLS
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 with quartz countertops, while additional baths feature cultured marble. LVP flooring runs through the main areas with carpeted bedrooms for comfort. Curb appeal shines with white siding, board and batten accents, cedar posts and gables, and a striking mahogany front door. Black exterior/white interior windows complete the modern farmhouse feel. If you’re looking for space, style, and quality craftsmanship all in one, this home delivers.

14002 Old Suffolk Road, Windsor
$651,000
5 Beds ⋅ 5 Baths ⋅ 10636500 MLS
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 effortlessly into a classic kitchen. The main level offers a formal dining room, a family room, a dedicated laundry room, 2 full bathrooms, and a primary suite. Upstairs, you'll find two additional spacious secondary bedrooms and another full bath. Bonus Multi-Generational Living: Perched above the attached 3-car garage is fully equipped in-law suite, complete with its own kitchen, living room, bedroom, and full bathroom! Enjoy peaceful mornings on the charming front porch and upgrades to include a 15kW generator, 3-zone HVAC, new dishwasher, new well bladder, and a 1-year Cinch home warranty.

18513 Shady Pine Lane, Windsor
$602,902
4 Beds ⋅ 3 Baths ⋅ 10629546 MLS
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 powder room, an additional storage area instead of the pocket office, primary bath options, several kitchen layout options, a covered porch, sunroom, or screen porch options, and an optional second floor with loft, bedroom four and five, and storage options.

12348 Ava Lane, Windsor
$569,990
4 Beds ⋅ 3.1 Baths ⋅ 10631647 MLS
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! Enjoy Windsor's small-town vibes with rapid access to Route 460, local dining, and shopping. UP TO $20,000 IN CLOSING COSTS WITH SELLER APPROVED LENDER + MOVE IN PACKAGE!

12199 Ava Lane, Windsor
$549,000
4 Beds ⋅ 3.1 Baths ⋅ 10640852 MLS
Looking for the serenity and privacy of country living with the convenience and amenities of the suburbs? Look no further! This home boasts 1.94 acres, but is only minutes from Historical Downtown Smithfield's restaurants and shopping. Step inside and you will notice an open floor plan and a large eat in kitchen which are perfect for entertaining. The entire 2nd floor consists of a spacious bedroom, expansive walk in closet and a full bath. Your backyard offers endless possibilities with a deck, above ground pool, storage shed, and plenty of wide open space to make it your own. Schedule your showing today!

17403 Carroll Bridge Road, Windsor
$507,000
5 Beds ⋅ 3 Baths ⋅ 10632279 MLS
Rare find in the highly sought-after Windsor Woods Community!! Situated on a 1 acre lot, this beautifully updated 5 bedroom, 3 full bath home offers the space, features, & value buyers are looking for — all under $500K. Major updates throughout the home include flooring, paint, carpet, appliances, pool improvements, garage floor epoxy, & a new fully renovated primary bathroom with soaking tub, walk in shower, updated vanity, & stylish finishes. Inside, you’ll love the soaring cathedral ceilings, open feel, & catwalk overlook full of character. The first floor primary suite plus an additional first floor bedroom & full bath offer flexibility for guests, office space, or multi generational living. Outside, enjoy an above ground pool, hot tub, newer pool deck, large driveway, & spacious yard with room to relax or entertain. Tons of storage & a neighborhood buyers are always asking for, this one checks the boxes!

11072 Wythe Drive, Windsor
$490,000
3 Beds ⋅ 2 Baths ⋅ 10626397 MLS
Welcome Home to 16290 Trump Town Road in Windsor, VA! Nestled on over 3 peaceful acres in Isle of Wight County, this well-built brick ranch offers the ultimate blend of space, privacy, and natural beauty. Boasting 3 bedrooms, 2 baths, and approx. 2,022 sq ft, the home features a comfortable layout with generously sized rooms and abundant natural light. Enjoy total peace of mind with a whole-home Generac generator. A standout feature for hobbyists is the oversized detached garage with large bays and a durable metal roof for vehicles, equipment, or a workshop! An additional carport provides even more covered parking. Step outside to enjoy tranquil pond views and expansive acreage, offering endless possibilities for outdoor living, gardening, or simply relaxing in your quiet country setting. With its solid construction and functional outbuildings, this well-maintained rural retreat is a must-see. Your country haven awaits!

16290 Trump Town Road, Windsor
$490,000
4 Beds ⋅ 3 Baths ⋅ 10625596 MLS
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 construction.Outside, the possibilities are endless with a detached shop/garage offering over 1,100 square feet, two additional sheds (one climate-controlled), and a carport, giving you all the space you need for hobbies, storage, or a home-based business.Enjoy the peace and privacy of country living while still being just a short drive to Smithfield, Windsor, Suffolk, and Newport News. This is the kind of property that doesn’t come around often. Space, charm, and versatility all in one!

17314 Jolly Circle, Windsor
$460,000
4 Beds ⋅ 3 Baths ⋅ 10631317 MLS
Welcome to this well-maintained transitional home in Windsor Woods in Windsor, Virginia. Built in 2006 and cared for by its original owner, this home offers over 2,500 square feet with four bedrooms, three full baths, a loft, and a dedicated office for flexible living. The first-floor primary suite features a handicap-friendly walk-in shower and soaking tub, while a secondary bedroom connects to a Jack-and-Jill bath. The Great Room area includes a cozy propane fireplace. Great for relaxing or entertaining. You also have two walk-in attics and a two-car garage for practical storage. Set on a fenced half-acre lot, the outdoor space includes pecan and fruit trees, a screened porch, deck, pergola, and two sheds. The roof was replaced in 2024, and the home has been carefully maintained by its original owner. Located in the Windsor School District with no HOA,

10455 Sylvia Circle, Windsor
$445,000
5 Beds ⋅ 2.1 Baths ⋅ 10618688 MLS
Welcome to this stunning 5 bed, 2.5 bath home in the desirable Holland Meadows community, built in 2020. This spacious home features an open floor plan with a living area that flows seamlessly into the open kitchen. The kitchen boasts a large island, granite countertops, stainless steel appliances, pantry, and plenty of cabinet space. A convenient mudroom adds organization. All bedrooms are generously sized, with the primary suite offering a large walk-in closet and a beautiful bathroom complete with a double vanity and an oversized walk-in shower. Step outside to enjoy a private patio and a large, fully fenced backyard—great for relaxing, hosting gatherings, or giving pets room to play. The home also includes a 2-car attached garage. Located in a highly rated school district and just minutes from shopping, dining, and major highways, this home offers a blend of comfort, convenience, and modern living.

11492 Savannah Street, Windsor
$420,000
3 Beds ⋅ 2 Baths ⋅ 10626972 MLS
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 or just enjoying quiet evenings outside. Solid brick construction means low maintenance. Detached garage/workshop. Conveniently located near local shops, schools, and an easy drive to surrounding areas, this home blends small-town charm with practical living. Move-in ready with room to make it your own!

24347 Lovers Lane, Windsor
$419,900
3 Beds ⋅ 2 Baths ⋅ 10625835 MLS
Welcome home to this beautifully laid-out 3-bedroom, 2-bath property tucked away on a quiet, private street. The spacious primary suite is a true retreat, featuring an en-suite bath, walk-in closet, and additional flex space perfect for a home office, nursery, or cozy sitting area. The open-concept kitchen, living, and dining areas create an inviting flow that’s ideal for both everyday living and entertaining. Step outside to enjoy the large, nearly half-acre lot offering plenty of room to relax, play, or garden. The oversized garage with double doors provides excellent space for vehicles, hobbies, or extra storage. If you’re looking for privacy, space, and functionality all in one, this home is a must-see!

16 Holland Drive, Windsor
$400,000
4 Beds ⋅ 2 Baths ⋅ 10645219 MLS
Welcome home to this beautifully updated brick ranch nestled in the charming small town of Windsor, where neighbors quickly become friends and community feels like family. Thoughtfully upgrades throughout, this move-in-ready home features new flooring and fresh paint, creating a bright and inviting atmosphere.The updated kitchen offers new countertops, stainless steel appliances, and a functional layout that's perfect for everyday living or entertaining. Major improvements provide peace of mind, including new windows, a new HVAC system, and updated electrical in the detached garage.Step outside to the fully fenced backyard—an ideal space for summer cookouts, family gatherings, or simply letting kids and pets play freely. Whether you're searching for the comfort of small-town living or a home that's been thoughtfully updated, this Windsor gem is ready to welcome you home.

17 Randolph Drive, Windsor
$400,000
10628666 MLS

8450 Windsor Boulevard, Windsor
$384,999
3 Beds ⋅ 2 Baths ⋅ 10624837 MLS
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. A designer lighting package enhances the bright, airy feel of every room. Step outside to a large fenced backyard, ideal for entertaining, or play. Conveniently located with quick access to Route 460, and just minutes from shopping, dining, and commuter routes. Don’t miss this opportunity to own a new construction home in Hampton Roads with high-end finishes and exceptional convenience.

10176 Bank Street, Windsor
$384,900
3 Beds ⋅ 2 Baths ⋅ 10627003 MLS
Sprawling brick ranch in the heart of Windsor sits on .91 AC! Lots of privacy! Convenient to town yet tucked away on a quiet st with no thru traffic. Home has insulated tilt windows, arch shingle roof, thermal sheet insul of entire attic, lg bedrooms, sprawling rear yard to incl wooded areas, central vac, sec sys, whole house attic fan & more. Easy to show! Wood burning fireplace works well but conveys AS-IS. 3 sheds in rear yard. Lg white shed has 100 amp panel, TV & mini fridge that convey!

53 Pine Lane, Windsor
$380,000
3 Beds ⋅ 2 Baths ⋅ 10641944 MLS
Hunter's paradise on 5.93 private acres! Zoned Rural Residential, this peaceful property offers the perfect blend of privacy, comfort, and country living. Surrounded by abundant wildlife, it's an ideal retreat for hunters, nature lovers, or anyone looking to escape the hustle and bustle. Enjoy your morning coffee on the full-length front porch while watching deer, birds, and other wildlife. The approximately 1-acre fenced yard is perfect for pets, gardening, or outdoor activities. A detached garage/workshop with upper-level storage provides plenty of room for projects, equipment, or recreational gear. Chickens and horses are welcome, making this property well-suited for a rural lifestyle. The nearly 1,500-square-foot ranch features an open-concept living and dining area with vaulted ceilings and a centrally located wood stove, creating a warm and inviting gathering space. Ceiling fans throughout add year-round comfort. The spacious kitchen includes granite countertops, a pantry, and ample cabinet and counter space. Down the hall are three bedrooms, including a first-floor primary suite with a private bath featuring a relaxing jetted tub. Additional features include a 27.5 kW automatic whole-house generator, providing dependable backup power for added peace of mind. If you've been searching for acreage, privacy, abundant wildlife, and the comforts of country living, this exceptional property is ready to welcome you home.

9269 Whispering Pines Trail, Windsor
$370,000
3 Beds ⋅ 1.1 Baths ⋅ 10624428 MLS
This well-maintained home blends classic charm, full of character, and thoughtful updates offering plenty of space both inside and out right in the heart of Windsor! You’ll find a gorgeous interior featuring a dedicated dining room, three generous bedrooms, and an additional versatile room perfect for a home office, playroom, or flex space. A large living space also leads to an updated kitchen showcasing beautiful soapstone countertops that add timeless style and durability. Outside, the spacious, fully fenced backyard provides plenty of room to relax, entertain, or play. A long driveway offers parking for at least five vehicles and leads to a huge two-car detached garage. The rear half was beautifully redone into a workshop in 2022—perfect for hobbies, projects, or extra storage. Major improvements also include a new roof, crawl space work, gutters, and a brand-new back deck all completed in 2025. Don’t miss the opportunity to make this phenomenal property your next home!

24 N Court Street, Windsor
$355,000
4 Beds ⋅ 2 Baths ⋅ 10639208 MLS
This house has it all - land, charm and updates throughout! 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 bring your toothbrush. Picture starting your morning with coffee in the sunroom or reading a book by the cozy fireplace; either way, it’ll likely be the best part of your day. Schedule your showing today.

26 N Court Street, Windsor
$354,999
3 Beds ⋅ 2.1 Baths ⋅ 10619079 MLS
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 with quick access to Route 460, and just minutes from shopping, dining, and commuter routes. Don’t miss this opportunity to own a new construction home in Hampton Roads with high-end finishes and exceptional convenience.

105 S Court Street, Windsor
$340,000
4 Beds ⋅ 1 Baths ⋅ 10624604 MLS
This home features 4 spacious bedrooms and a large full size bathroom, home is move-in ready with thoughtful upgrades throughout. Recent improvements include some Fresh interior paint creates a bright, welcoming atmosphere, kitchen has newer appliances, kitchen cabinets and floor, some rooms have new carpet, roof only 2 years old, newer huge 2 car bay garage/workshop. Nice real hardwood floors. Backyard fenced in, two sheds for outside equipment storage. Envision the added comfort and value with the possibility of adding a full bathroom to the primary. Right in the heart of Windsor. This home will not disappoint.

25 E Griffin Street, Windsor
$335,000
3 Beds ⋅ 2.1 Baths ⋅ 10628745 MLS
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.

24456 Walters Highway, Windsor
$320,000
2 Beds ⋅ 1 Baths ⋅ 10634365 MLS
Modern Luxury Meets Country Living in Windsor! Experience the perfect blend of high-end style and rural tranquility on this stunning 1.5-acre home. This meticulously renovated 2-bedroom, 1-bath home offers "new everything," providing total peace of mind and upscale comfort. Step into a bright interior featuring a chef’s kitchen with premium appliances and a spa-like bath. Thoughtfully designed for efficiency, the layout includes a dedicated laundry room and a functional mudroom. Move in with zero worries thanks to a new roof, HVAC, siding, and energy-efficient windows. Built for the hobbyist or craftsman, the property boasts a massive 3-stall pole barn with a spacious attached workshop. Whether you need room for equipment, animals, or creative projects, this acreage delivers. Don't miss out—schedule your private tour today and see this gem in person!

14242 Trump Town Road, Windsor
$315,000
3 Beds ⋅ 2 Baths ⋅ 10639269 MLS
Completely renovated, beautiful ranch on 1.35 acres. Country living at it's best. So quiet, yet minutes from the highway! This home boasts new siding, new roof, and new HVAC. The open brand new kitchen has granite counters and SS appliances. There are 2 living spaces as well as 2 brand new bathrooms. All new paint, flooring and lighting through out.

11115 Dunston Drive, Windsor
$315,000
3 Beds ⋅ 2 Baths ⋅ 10639118 MLS
Come and make your new home in Windsor Virginia, voted the friendliest community by Nextdoor for 2026. For Sale is this approximately 1250 square foot 3 bedroom two bath Ranch home. This home sits on a .34 acre corner lot in a quite established non-HOA neighborhood. The home sits on a crawl space and has had plumbing, electrical and HVAC upgrades in the past. The property had a 16x20 one car oversized metal garage which has power and HVAC. It also has a 12x10 shed that has electricity. This home is in close proximity to retail establishments, library, and parks in town. Two Isle of Wight County schools, Windsor High and Windsor Middle, are also nearby to this home.

24129 Johnson Avenue, Windsor
$315,000
3 Beds ⋅ 2 Baths ⋅ 10627016 MLS
Welcome to this charming 3-bedroom, 2-bath brick rancher in the heart of Windsor, VA! Situated on a 0.42-acre end-of-street lot, this move-in-ready home offers 1,557 sq. ft. of comfortable living space. Highlights include a spacious, light-filled sunroom overlooking a private, fenced backyard-perfect for relaxing or entertaining. This well-maintained home features a 1-car attached garage, pull-down attic stairs for extra storage, a functional whole house fan, and the convenience of public water and sewer. Located in the sought-after Isle of Wight County school district, you are minutes from local parks, shopping, and dining. Enjoy the best of small-town living with a seamless commute to Suffolk, Smithfield, and the greater Hampton Roads area via Rt. 460 and Rt. 258. This property offers the ideal blend of classic character and modern ease. Schedule your private tour today and see why life is better in Windsor!

54 Pine Lane, Windsor
$310,000
3 Beds ⋅ 1.1 Baths ⋅ 10639587 MLS
This charming farmhouse sits on a generous corner lot of more than an acre and has been updated over the years with replacement windows, HVAC, an upstairs half bath, and an improved downstairs bath. The 2+ car oversized detached garage and 30x40 metal workshop/garage offer abundant workspace and storage. Located in a sought-after school district, this home offers peaceful country living just 10 minutes from Smithfield or Windsor. Truly a must-see property.

17009 Florida Avenue, Windsor
$301,000
3 Beds ⋅ 2 Baths ⋅ 10634180 MLS
Beautifully maintained and thoughtfully updated 3-bedroom, 2-bath ranch situated on a scenic and spacious 0.94-acre lot in Windsor. This inviting home features a functional open layout with a bright family room, eat-in kitchen, and a generously sized primary suite complete with a private full bath. Two additional well-proportioned bedrooms and a second full hallway bath provide plenty of space for family or guests. The oversized garage offers exceptional storage and flexibility, with ample room for vehicles, hobbies, projects, or a workshop setup. You'll enjoy the expansive backyard with peaceful country views and plenty of room to relax, entertain, or garden. Perfect for those seeking the tranquility of country living while still being conveniently close to shopping, dining, and other modern amenities. Recent updates include a new HVAC system (2024) and new gutter system (2026).

17050 Florida Avenue, Windsor

Some listings may be duplicated in the search results due to the co-mingling of listings from more than one multiple listing service. Should there be different listing information between the duplicated listings; user is advised to verify the accuracy of the listing information before making any financial decisions.