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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
$550,000
3 Beds ⋅ 2.1 Baths ⋅ 10602770 MLS
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 half bath. Upstairs, two bedrooms, a full bath, and a flexible loft serve as an office or guest space. Surrounded by mature timber and bordered by Villines Swamp to the north, the property teems with wildlife. Relax on the full-length front porch or the walk out deck by the 18 ft above-ground pool. A 24 x 22 metal-roof carport, a 40 x 24 climate-controlled metal building with roll-up doors and loft storage, and a 32 x 10 barn with a 32 x 22 covered area and chicken/duck pens offer ample utility. A great home for a tranquil, rural lifestyle.

9161 Whispering Pines Trail, 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
$510,000
4 Beds ⋅ 2.1 Baths ⋅ 10602163 MLS
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!

11397 Shiloh Drive, 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
$479,000
4 Beds ⋅ 4 Baths ⋅ 10599020 MLS
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 throughout the entire home. The updated kitchen featuring quartz counter tops tile back splash and stainless steel appliances brightens the space beautifully. Master Bedroom features walk-in closet and master bath with double vanities. Total of 3 br and 3ba in main home. Plus additional Rm that could be office or play Rm with access to walk in attic. Plenty of storage, separate laundry room leads to 2 car garage, wrap around deck and large yard. Mechanics delight! Car lift, engine stand, fans, deep sink & bathroom in detached garage. Mother-in-law suite features family Rm, kit, bed, bath & utility room.

24192 Twin 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
$456,500
5 Beds ⋅ 3 Baths ⋅ 10613459 MLS
Located in the established Windsor Woods community, this spacious 5-bedroom, 3-full-bath home offers a flexible layout and comfortable living with no HOA. The first floor features a primary suite and a guest bedroom, along with soaring cathedral ceilings that fill the home with natural light and create an open, airy feel. Upstairs offers three additional generously sized bedrooms with excellent storage, including a large walk-in attic with potential for future finished living space. Recent updates include brand-new carpet throughout, fresh paint, and many interior doors replaced for a refreshed interior. Enjoy relaxing or entertaining on the back deck overlooking a peaceful pond, complete with an awning perfect for summer BBQs and evenings outdoors. Conveniently located with a toll-free route to nearby military bases and easy access to the charming town of Windsor, Smithfield, and Downtown Suffolk, this home offers space, updates, and a prime location.

23068 Andrew Court, 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
$445,000
4 Beds ⋅ 3.1 Baths ⋅ 10613338 MLS
Lovely 4 bedroom 3.5 bathroom home located in the Holland Meadows neighborhood of Windsor. IN-Ground Swimming pool / Salt water / located in a cup-de-sac / white vinyl back yard. You will love the home and the neighborhood! Items to convey - all items to include all appliances to include the washer and dryer, 8'/8' garden shed . Tile showers / Granite island and vanities. electric fire place in great room. Windsor school system.

24401 John Henry Street, Windsor
$435,000
3 Beds ⋅ 2 Baths ⋅ 10601737 MLS
Well maintained ranch set back off the road. Centrally located and accessible to all of IOW County. Located on 7.5 acres-cleared home site with the remainder wooded. Gravel front circle driveway. Split floor plan with Primary bed/bath on one side-2 additional beds & bath on the other. Eat in kitchen with a nook off from it that could be an office or whatever you decide to make it. Screened back porch off of kitchen through French doors-Front porch already has a swing that is just waiting for you to come make it your own!

17359 Courthouse Highway, 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
$415,000
3 Beds ⋅ 2 Baths ⋅ 10613342 MLS
Set on a private 2-acre lot, this well-maintained brick home offers space, comfort, and efficiency. With 2,010 square feet of living space plus a sunroom and attached garage, there is room to spread out both inside and out. Enjoy outdoor living with a large back deck, patio off the sunroom, and a storage shed, all surrounded by peaceful privacy. Inside, the main living area features vaulted ceilings and abundant natural light, creating an open and inviting feel. The first floor includes a spacious bedroom and full bath, ideal for guests or main-level living. Enjoy the large laundry room off the garage with cabinets for storage. Upstairs you will find two generously sized bedrooms, a full bath, and ample storage. Recent updates include a roof less than two years old and solar panels that provide significant savings on the electric bill. With large rooms, a thoughtful layout, and a serene setting, this home offers the perfect blend of privacy, functionality, and long-term value.

14494 Bowling Green Road, Windsor
$410,000
3 Beds ⋅ 2 Baths ⋅ 10611881 MLS
Welcome to country living at its finest. This beautifully maintained 3-bedroom, 2-bath home offers 2,141 sq ft of spacious, comfortable living in the heart of Windsor. From the moment you arrive, you’ll feel the charm and warmth this property provides. The inviting front porch sets the stage for an ideal place to start or end your day with a glass of iced tea while taking in the gorgeous VA sunsets. Step inside to a stunning open floor plan designed for both everyday living and effortless entertaining. The flow from the living room to the dining area and kitchen makes gathering with family and friends easy and enjoyable. Whether you’re hosting a holiday meal or relaxing on a quiet evening, this layout offers flexibility and comfort. And the impressive bonus room—ideal as a 4th bedroom, home office, or flex space. A nice deck gives you the perfect spot for grilling, entertaining, or simply enjoying the fresh country air. This one truly blends comfort, style, and country charm!

10419 Sylvia Circle, 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
$400,000
3 Beds ⋅ 2 Baths ⋅ 10605877 MLS
Well cared for brick ranch located on a large corner lot with updated master bath, LVP flooring, and in-ground pool and 2 car detached garage. Any family will love the large sunroom and the large bonus/flex room which could be used for many purposes: workout area, office, home schooling, or playroom. Roof was installed in 2023. Very close to shopping and major roadways.

24441 Lovers Lane, Windsor
$389,900
3 Beds ⋅ 2.1 Baths ⋅ 10601814 MLS
Great Purchase Opportunity for a One Owner Home on a Cul-de-Sac Street with Limited Traffic. Recent Upgrades Include Wood Flooring Downstairs. Many Functions of Home are Wired for Convenience Utilizing the Alexa App. Relax on the Concrete Patio and Admire the Lush, Green Lawn in the Private Back Yard Enclosed by a Vinyl Privacy Fence. Lots of Convenient Storage in Garage with Lofts & Cabinets Plus a Work Bench. Great Location with Easy Access In & Out of the Neighborhood.

11361 Lena Rose Street, 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
$384,999
3 Beds ⋅ 2 Baths ⋅ 10615487 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.

10174 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
$378,000
4 Beds ⋅ 2.1 Baths ⋅ 10605816 MLS
Welcome home to this 4 bedroom 2.5 bath Ranch built in 1968 with various improvments throughout the years. Home is waterfront on a pond that is partially owned by the homes who's properties border it. Roof was replaced in 2015. One heat pump was replaced in late 2013 and the other around 2018 and both have recently been serviced. Water heater was replaced around 2020. Flooring in family room was replaced with tile in 2015. Dock on the pond was completely rebuilt and completed in 2023.

24420 Lovers Lane, 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.