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31397 Lelia Lane, Isle of Wight - South
$219,800
3 Beds ⋅ 2 Baths ⋅ 10641867 MLS
Country Living with Endless Potential! Nestled in a rural setting, this single-story mobile home offers the perfect opportunity for homeowners looking to create their own country retreat. Situated on a spacious lot surrounded by open skies and natural beauty, this property provides a little privacy, tranquility, and room to grow. Inside, you’ll find a functional floor plan ready for your personal touches and updates. Whether you’re looking for a starter home, rental investment, or weekend getaway, this property presents endless possibilities to make it your own. Enjoy the freedom of rural living with outdoor space for gardening, hobbies, pets, recreational vehicles, or future improvements. If you’ve been searching for an affordable property with character, space, and unlimited potential, this is an opportunity you won’t want to miss. Schedule your showing today and imagine the possibilities!

31397 Lelia Lane, Isle of Wight - South

17 Randolph Drive, Isle of Wight - South
$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, Isle of Wight - South

18513 Shady Pine Lane, Isle of Wight - South
$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, Isle of Wight - South

27384 Colosse Road, Isle of Wight - South
$550,000
4 Beds ⋅ 2.1 Baths ⋅ 10633586 MLS
Spacious 4 Bedroom, 2 1/2 Bath Cape Cod on 3.63 Acres with Several Outbuildings. Relax and Enjoy the Solitude of Your Property on the Large Front Porch or the 800+ SF Composite Deck with Storage Underneath. Additional Space Provided Year Round in the Rear Sunroom. Stay Cool Over the Summer in the Above Ground Pool. Large Kitchen with Dining Area and Pantry. Bring Your Animals for the 5 Stall Barn with Tack Room & Hay Loft, Chicken Coop, Run In Shed & Fenced Pasture. 35' x 24' RV and Equipment Shelter Provides Much Versatility. Additional Shed with Workbench is Ideal Workshop. Peace of Mind Provided by the Propane Fueled 20KW Stand By Generator. Paved Driveway and Deep Well. Many Recent Upgrades to Home Include LVP Flooring, New Windows, HVAC, Master Bath and Roof. Served by Desired Windsor & Carrsville School Zones. Just Minutes from Conveniences in Town of Windsor. Closing Costs. * ATTENTION VETERANS: 2.625% Qualifying VA Assumable Mortgage Available. Contact Agent for Details.

27384 Colosse Road, Isle of Wight - South

14002 Old Suffolk Road, Isle of Wight - South
$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, Isle of Wight - South

14242 Trump Town Road, Isle of Wight - South
$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, Isle of Wight - South

15023 Five Forks Road, Isle of Wight - South
$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, Isle of Wight - South

7445 Mill Creek Drive, Isle of Wight - South
$226,000
1 Beds ⋅ 1 Baths ⋅ 10635794 MLS
Totally awesome opportunity to own a barn-dominium with huge garage in prime location. Come home to this peaceful country setting you will feel like you are on vacation! Located on the back of a 1-Acre lot so you can build your dream home when ready. The layout downstairs can be changed for the kitchen to be in the front of the house and a large living room to the back. Or just add more cabinets to the empty wall in the kitchen area. Upstairs has a great balcony to enjoy morning coffee and watch the deer in the field. Amazing garage with two roll up doors and a large workshop for whatever hobbies you enjoy. Multiple places to park all your play toys! Only 7 minutes to town with stores and eateries! Location is less than an hour to the beach, bases, shipyards and all Hampton Roads. Come check it out.

7445 Mill Creek Drive, Isle of Wight - South

10455 Sylvia Circle, Isle of Wight - South
$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, Isle of Wight - South

29527 Walters Highway, Isle of Wight - South
$389,000
4 Beds ⋅ 3 Baths ⋅ 10629251 MLS
Welcome home to this beautifully renovated all-brick ranch, perfectly situated on a spacious .69-acre lot! This move-in ready home offers 4 bedrooms, including two with private en-suite baths, providing flexibility for guests or multi-generational living. The open-concept living room and kitchen create a bright and inviting space. A separate den with a cozy fireplace adds the perfect spot to relax and unwind or give the kids a dedicated space. Step outside to enjoy the large, fenced-in backyard with plenty of room to play, garden, or host gatherings. Located in a desirable school district, this home offers the best of country living while still being just a short commute to all that Hampton Roads has to offer.

29527 Walters Highway, Isle of Wight - South

11072 Wythe Drive, Isle of Wight - South
$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, Isle of Wight - South

2.41AC Carrsville Highway, Isle of Wight - South
$20,000
10630301 MLS
Discover your own private escape on this 2.41-acre heavily wooded parcel tucked away in the peaceful countryside of Carrsville. With RAC zoning (Rural Agricultural-Conservation), this property offers incredible flexibility for a wide range of uses—whether you're looking to build a home, invest in land, create a private retreat, or start your homestead dream. The property borders railroad tracks along the rear of the property. Conveniently located with access to major roads, yet secluded enough for true peace and quiet. Whether you're a builder, a family looking for space, an investor seeking affordable land, or someone ready to unplug and live simply—this property has the versatility and potential you’re looking for. GPS to 32405 Bobcat Lane which will take you to the parcel at Carrsville Hwy (DO NOT go back to the Bobcat Lane address as this is only for locating property and the house is not part of the sale and private property.

2.41AC Carrsville Highway, Isle of Wight - South

13421 Shiloh Drive, Isle of Wight - South
$270,000
2 Beds ⋅ 2 Baths ⋅ 10627541 MLS
Private sanctuary cabin-inspired home nestled on a lush, one acre lot. Offering the perfect blend of peaceful country living and modern convenience, this home provides breathtaking woodland views and a layout designed for effortless relaxation. Enjoy county living inside Isle of Wight County - just a quick ride to Windsor shopping and restaurants. Duel Primary Suites providing ultimate privacy and comfort for residents and guest alike. Ensuites, open to the heart of the home, open concept living space framed by large windows that bring the beauty of the outdoors inside. The living area flows onto a large wrap around back deck creating a seamless transition for living and entertaining. The roof is < 12 years old. Property includes a 400 sq ft detached garage perfect for storage, cars or woodshop. Current brown light fixture in main living space between ceiling fans does not convey. Call or text listing agent for a property website or to schedule a private tour.

13421 Shiloh Drive, Isle of Wight - South

8277 Mill Creek Drive, Isle of Wight - South
$300,000
3 Beds ⋅ 1.1 Baths ⋅ 10631384 MLS
PRIDE OF OWNERSHIP SHINES in this stunningly transformed Zuni retreat! What once was a traditional galley kitchen has been masterfully reimagined into a breathtaking open-concept living and kitchen area, creating a seamless flow for modern life. No detail has been overlooked, from the fully updated bathrooms to the brand-new flooring and fresh professional paint throughout. Set on a sprawling 1.25-acre lot, this property is a rare find for those needing serious space. It features dual outbuildings: a huge, attached garage for everyday convenience plus a massive, detached workshop for projects, car restoration, or a home business. This turnkey home is move-in ready and located in the Windsor School District, offering peace and quiet while remaining near to US-460 for an easy commute to Suffolk, Smithfield, and Franklin. With a fully updated interior and unparalleled exterior storage, you truly don't want to miss this one!

8277 Mill Creek Drive, Isle of Wight - South

24347 Lovers Lane, Isle of Wight - South
$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, Isle of Wight - South

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.

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