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10007 Old Myrtle Road, Isle of Wight - South
$197,500
3 Beds ⋅ 2 Baths ⋅ 10652506 MLS
Get in touch with country living with this 3 bedroom, 2 bath home. Add your personal touches & get your garden started. Convenient location to Tidewater area EZ commute. Top rated Carrsville Elementary School located only a few miles away. Priced to sell ! Please compare to what's available in this price range. No restrictions on use of land other than public ordinances-say goodbye to HOAs. Sit our in your own yard and star gaze with maybe a bon fire cooking hot dogs on a stick over the open fire. Blackwater river which is a scenic river located only a few miles away with a public launch area in Franklin (about 10 miles).

10007 Old Myrtle Road, Isle of Wight - South
19251 Tomlin Hill Drive, Isle of Wight - South
$419,000
3 Beds ⋅ 2 Baths ⋅ 10650453 MLS
Welcome to your Zuni retreat at 19251 Tomlin Hill Dr! This beautifully updated 3 bedroom, 2 bathroom home blends modern comfort with an incredible outdoor lifestyle. Inside, enjoy a bright kitchen with a farmhouse sink, vaulted ceilings in the primary bedroom, a home office with built-ins. New can lights installed (2024). Big-ticket items are completely covered: brand-new HVAC & mini-split (6/2026), new water heater (2/2020), and an upgraded septic/drainfield (2019). The massive detached garage boasts polished concrete floors. Entertain effortlessly in your backyard oasis! The re-decked back porch with new stairs/railings (2023) flows into a gorgeous pergola (2020) and a brand-new outdoor bar/cooking area (2025). Surrounded by nature, you'll be greeted by unique wildlife like otters, turtles, frogs, and birds right in your own yard. This home is fully turnkey and ready for its next chapter. Schedule your tour today before it's gone!

19251 Tomlin Hill Drive, Isle of Wight - South
18688 Orbit Road, Isle of Wight - South
$110,000
3 Beds ⋅ 1 Baths ⋅ 10650876 MLS
Attention Investors, Rehabbers & DIY Buyers! Opportunity to restore and build equity with this 3-bedroom, 1-bath ranch situated on a spacious 2 acre wooded lot in Isle of Wight County. Offering approximately 1152 sq. ft., this home features a functional single-level layout with a family room, kitchen, and first-floor primary bedroom. The level lot provides plenty of outdoor space and privacy with mature trees surrounding the property. Home needs repairs and updates throughout and is ready for your vision and creativity. Ideal for investors seeking their next flip, rental opportunity, or buyers looking for a project with upside potential. Property being sold strictly AS IS, WHERE IS. Seller will not make any repairs, inspections or provide utilities. Buyer to perform all due diligence.

18688 Orbit Road, Isle of Wight - South
24370 John Henry Street, Isle of Wight - South
$426,300
4 Beds ⋅ 2.1 Baths ⋅ 10654550 MLS
Welcome to 24370 John Henry Street in Windsor! Built in 2016, this well-maintained 4-bedroom home offers approximately 2,018 square feet of living space with a layout designed for everyday living and entertaining. The spacious kitchen provides room for gathering and flows into the main living areas, while generously sized bedrooms offer flexibility for a variety of needs. Situated on approximately one-third of an acre, the back yard is bordered with a beautiful tree line for a little privacy on one side as well as a flagpole centered in the front yard! Along with an attached garage for parking and additional storage the current owners have upgraded that space with a mini split system to allow for convenient flexibility of use. This beautiful home is ready for it's next chapter, come see all it has to offer.

24370 John Henry Street, Isle of Wight - South
27098 Colosse Road, Isle of Wight - South
$615,000
4 Beds ⋅ 2.1 Baths ⋅ 10648740 MLS
Country living with room to roam! This spacious 3,300+ sq. ft. home is nestled on 2.16 acres and offers the perfect setup for those looking to enjoy a little more space and a lot more freedom.The barn offers endless possibilities for animals, hobbies, & storage. The property allows horses, cows, donkeys, chickens, and more! Inside, you’ll find a fairly open floor plan with the primary suite conveniently located downstairs, along with tons of storage throughout. Step outside and enjoy the expansive wrap-around front porch, a bright sunroom that is great for entertaining. If you’ve been dreaming of country living with plenty of space for the whole family—and your four-legged friends—this one is worth a look!

27098 Colosse Road, Isle of Wight - South
11572 Savannah Street, Isle of Wight - South
$655,132
5 Beds ⋅ 4 Baths ⋅ 10622802 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!

11572 Savannah Street, Isle of Wight - South
5041 Pruden Road, Isle of Wight - South
$370,000
3 Beds ⋅ 2.1 Baths ⋅ 10648093 MLS
"Brand New COMPLETE! Beautiful custom 3 bedroom, 2.5 bath by Daniels Construction. This lovely home features a primary ensuite and walk-in closet, cozy wall-to-wall carpet, gorgeous tile flooring and QUARTZ counter-tops. Open & spacious floor plan features kitchen with 42-inch upper cabinets with easy close drawers/ doors, stainless steel appliances; Ceiling fans featured throughout. 9-foot ceilings downstairs. Heated LED mirrors with lights; 2-car attached garage. Double hung windows, tons of upgrades on 5+ acres!

5041 Pruden Road, Isle of Wight - South
17479 Courthouse Highway, Isle of Wight - South
$605,000
4 Beds ⋅ 2.1 Baths ⋅ 10648830 MLS
The one you've been waiting for! Your very own country oasis situated on 3.62 acres of land just 15 minutes from Downtown Smithfield/Mainstreet. Home features a formal dining room, beautifully updated kitchen with eat in area, as well as a huge living room with built-in bookshelves. Enjoy quiet evenings on the large back deck, or morning coffee on the wrap around front porch. In addition to the 2 car attached garage the property also features a large detached 5 car covered storage shed, and 2 car enclosed metal storage building with 9k pound auto lift and additional electric panel. New deep water well installed late 2023. This updated home is ready for a new family!

17479 Courthouse Highway, Isle of Wight - South
32229 Walters Highway, Isle of Wight - South
$275,000
3 Beds ⋅ 1 Baths ⋅ 10647162 MLS
Well-maintained, move-in ready, brick ranch situated on a spacious country lot with an additional parcel included! Recent updates include beautiful, refinished hardwood floors, fresh paint in & out, new metal roof, new windows, new well, and new kitchen appliances. The large kitchen provides plenty of cabinet and counter space, while the in-unit laundry adds everyday convenience. Outside, you'll find both an attached carport and a detached garage, offering ample parking, storage, or workshop space. Enjoy the privacy of country living while remaining just a short drive from shopping, dining, major highways and other amenities. A great opportunity for anyone looking for a starter or downsizer home with valuable updates and plenty of outdoor space!!

32229 Walters Highway, Isle of Wight - South
21483 Chestnut Lane, Isle of Wight - South
$380,000
3 Beds ⋅ 2 Baths ⋅ 10650026 MLS
Built in 2015 with a 3rd bedroom conversion later, the home and setting is awesome! Country living with all the feel of a new modern day home. Just under 6 acres, the home is ready and don't forget your farm animals. The property is fully fenced around the perimeter and into 4 sections making it easy to divide the animals if needed. You can let your dog out to roam free in the entire yard! Abundant wildlife throughout as much of the trees on the property consist of mature white and red oaks. Private Road access off of Highway 460 and just minutes from local stores. Rare opportunity for a newer home with acreage. Goat shed & pen, dog pen and chicken house & pen. Feed shed, well shed Playset conveys. Covered back porch, Peach, Apple & Pear trees. Granite counter tops in kitchen and too many other feature and items to list.

21483 Chestnut Lane, Isle of Wight - South
8482 Cut Thru Road, Isle of Wight - South
$450,000
3 Beds ⋅ 2 Baths ⋅ 10640067 MLS
Nestled on 1.63 acres in the quiet community of Zuni, this beautifully maintained home offers the perfect blend of charm, comfort, and space. The current owners have meticulously cared for the property, restoring its warm, inviting character and creating a place that truly feels like home.Step inside to find gorgeous hardwood floors that add timeless appeal throughout the living spaces. The desirable open floor plan provides the perfect setting for entertaining family and friends, while also offering enough room for everyone to enjoy their own space when needed.Whether you're gathering around for holidays, hosting weekend get-togethers, or simply enjoying a peaceful evening at home, this property delivers the flexibility and comfort today's buyers are looking for. Situated on over an acre and a half, you'll appreciate the privacy, tranquility, and room to enjoy country living while still being within reach of everyday conveniences.This is more than just a house, its home!

8482 Cut Thru Road, Isle of Wight - South
28000 Walters Highway, Isle of Wight - South
$190,000
3 Beds ⋅ 1 Baths ⋅ 10649488 MLS
Great investment opportunity in Walters! Spacious 2.28acre country property offers potential for buyers looking for a renovation project, investment property or chance to bring a home back to life! This property is in fixer upper condition and will require some repairs and updates, making it ideal for someone ready to put in the work and add the value! Situated in a peaceful rural setting, the property offers plenty of potential and room to make your own. Additional room downstairs can make a 4th bedroom! Whether you're an investor looking for your next project or a buyer searching for an affordable property with possibilities, this one is worth a look!

28000 Walters Highway, Isle of Wight - South
23 Roberts Avenue, Isle of Wight - South
$200,000
2 Beds ⋅ 1 Baths ⋅ 10658834 MLS

23 Roberts Avenue, Isle of Wight - South
56 Church Street, Isle of Wight - South
$200,000
2 Beds ⋅ 1 Baths ⋅ 10658830 MLS

56 Church Street, Isle of Wight - South
24 W Windsor Boulevard, Isle of Wight - South
$875,000
10658821 MLS
Large 4300 SF Commercial Building located on busy Route 460 in the Town of Windsor. Building has option for many uses to include Convenience Store (original use), Retail, Office, Auction House (current use), Restaurant and others. Large parking lot in front and additional parking on the left side as well as room for expansion.

24 W Windsor Boulevard, Isle of Wight - South
22392 Barrett Town Road, Isle of Wight - South
$365,000
3 Beds ⋅ 2.1 Baths ⋅ 10654613 MLS

22392 Barrett Town Road, Isle of Wight - South
44 W Windsor Boulevard, Isle of Wight - South
$199,000
2 Beds ⋅ 1 Baths ⋅ 10654705 MLS

44 W Windsor Boulevard, Isle of Wight - South
42 W Windsor Boulevard, Isle of Wight - South
$199,000
2 Beds ⋅ 1 Baths ⋅ 10654693 MLS

42 W Windsor Boulevard, Isle of Wight - South
9269 Whispering Pines Trail, Isle of Wight - South
$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, Isle of Wight - South
24248 Liam Court, Isle of Wight - South
$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, Isle of Wight - South
200 Winchester Place, Isle of Wight - South
$545,000
4 Beds ⋅ 2.1 Baths ⋅ 10642345 MLS
This well-maintained 4-bedroom, 2.5-bath home offers the perfect blend of comfort, function, and lifestyle in a desirable no HOA community. Inside find beautiful updates, generous living spaces, and tons of storage. The home features updated flooring, remodeled bathrooms, a bright sunroom, and thoughtful improvements throughout. Outside is where this property truly shines. Relax and enjoy your own backyard retreat with a saltwater inground pool, deck, sunroom, and a 20’ x 12’ Olde Hickory workshop. The driveway includes RV/camper parking with a 30-amp plug-in, making it ideal for travelers, hobbyists, or anyone needing extra space. Located close to the charm and convenience of downtown Smithfield, shopping, dining, restaurants, medical facilities, and the new hospital area, this home also offers an easy commute to Harbour View, the Peninsula, and nearby military bases. Ready for a fast close!

200 Winchester Place, Isle of Wight - South
338 S Church Street, Isle of Wight - South
$860,000
4 Beds ⋅ 3.1 Baths ⋅ 10632427 MLS
This 4 bedrooms, 3.5 bath home has been completely restored with modern electrical, plumbing, HVAC, and so many more elegant finishes that complement the historic bones, with all the modern amenities. This unique floor plan allows for multiple living areas, and a Main bedroom retreat that will have you cozying up to the fireplace (1 of 4 active; 8 total), or lounging on one of 3 balconies all day long. The ground floor off of the garage is currently set up as a successful vacation rental, but would also make a lovely in law suite or man cave; while the top floor boasts a great room with a full kitchen, and butlers pantry. Several options to insert an elevator at your leisure. Home is near downtown shops, bars, and restaurants as well as nestled between two bridges to access Windsor castle park. Enjoy views of Windsor castle park and tidal Little Creek, just past the lush English Garden, designed with low maintenance in mind.

338 S Church Street, Isle of Wight - South
29 N Court Street, Isle of Wight - South
$248,000
5 Beds ⋅ 3.1 Baths ⋅ 10611576 MLS
Come see this 5 bedroom, 3.5 bath home in Windsor with detached garage and in-law suite.

29 N Court Street, Isle of Wight - South
5133 Joyners Bridge Road, Isle of Wight - South
$576,784
4 Beds ⋅ 3.1 Baths ⋅ 10649157 MLS
WELCOME TO THE SOMERTON III, A WONDERFUL FLOOR PLAN FROM SUFFOLK & ISLE OF WIGHTS PREMIER RURAL CUSTOM BUILDER. THIS HOME HAS A LARGE OPEN, FLOWING FLOOR PLAN, A BEAUTIFUL DOWNSTAIRS PRIMARY BEDROOM AND ALSO HAS A 2ND DOWNSTAIRS IN-LAW SUITE. ARE YOU TIRED OF LOOKING AT HOMES IN COOKIE CUTTER NEIGHBORHOODS WITH TINY YARDS AND HOMEOWNERS ASSOCIATIONS? HOW ABOUT SOMETHING DIFFERENT? GIVE US A CALL. WE BUILD ON LARGE COUNTRY STYLE LOTS AND ALL OF OUR HOMES ARE LOADED WITH AMAZING STANDARD FEATURES. CALL TODAY, WE WOULD LOVE THE OPPORTUNITY TO SHOW YOU HOW EASY AND AFFORDABLE NEW CONSTRUCTION CAN BE.

5133 Joyners Bridge Road, Isle of Wight - South
27175 Walters Highway, Isle of Wight - South
$375,000
3 Beds ⋅ 2 Baths ⋅ 10628033 MLS
Private country living on 6.2 acres! This 3-bedroom, 2-bath brick rancher offers 1,632 sq ft with a spacious layout and plenty of room to enjoy the outdoors. Features include a cozy wood-burning fireplace, sunroom perfect for relaxing year-round, and beautifully refinished wood floors (2026). Recent updates also include a new roof in 2026. The detached 1-car garage provides additional storage or workspace. Enjoy peace and privacy with no HOA while still having plenty of space for hobbies, gardening, or simply unwinding in your own secluded setting.

27175 Walters Highway, Isle of Wight - South
4312 Stevens Drive, Isle of Wight - South
$636,300
5 Beds ⋅ 4.1 Baths ⋅ 10629517 MLS
Beautiful custom home on 1.6 acres featuring a spacious, gourmet kitchen with custom cabinetry and new appliances. The home offers wood floors throughout, extensive crown molding and chair railing, two dens, a formal dining room, and a primary bedroom suite conveniently located downstairs.Upstairs includes four additional bedrooms and two full baths, providing plenty of space for family or guests. A separate apartment with bathroom sits above the two-car garage, complete with a private entrance-ideal for in-laws, guests, or rental income. The property also includes an attached one-car garage, giving you a total of three garage spaces. This home blends craftsmanship, comfort, and versatility on a generous 1.6-acre lot.

4312 Stevens Drive, Isle of Wight - South
26 N Court Street, Isle of Wight - South
$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, Isle of Wight - South
21418 Tan Road, Isle of Wight - South
$735,000
4 Beds ⋅ 3.1 Baths ⋅ 10642761 MLS
Welcome to your own private retreat in the heart of Smithfield! Nestled on 3.2 beautiful acres, this spacious 4-bedroom, 3.5-bath home offers the perfect blend of country living and modern convenience. Featuring two true primary suites. One on the first floor and one upstairs, this home is ideal for multi-generational living, guests, or added flexibility. Need to work from home? You’ll love the dedicated office, while the enclosed sunroom provides the perfect space to relax and enjoy peaceful views year-round. The location is hard to beat. Enjoy the privacy and tranquility of the countryside while being just 4 miles from Riverside Hospital, shopping, dining, and all that Smithfield has to offer. If you’ve been searching for space, versatility, and an unbeatable location, this is the one you’ve been waiting for.

21418 Tan Road, Isle of Wight - South
24129 Johnson Avenue, Isle of Wight - South
$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, Isle of Wight - South
12348 Ava Lane, Isle of Wight - South
$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, 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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