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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, 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
$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
$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
$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
$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
$650,000
4 Beds ⋅ 3.2 Baths ⋅ 10621435 MLS
Custom built and tucked away on 5 wooded acres this retreat offers privacy, space, and everyday comfort located just over the Surry line while still only minutes from downtown Smithfield. An open floor plan, beautiful wood floors, and an eat-in kitchen make the home feel warm and functional for daily life and entertaining. Step outside and you’ll see why this one stands out: a large screened porch and deck, a welcoming front porch, an inground pool, and even a chicken coop for a little homestead charm. The layout includes two en suite bedrooms, offering flexible options for guests, multigenerational living, or a private in-law suite. Secluded setting, thoughtful design, and room to breathe, this is country living with town conveniences close by.

1379 Moonlight Road, 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
$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
$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
$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, 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
$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
$510,000
3 Beds ⋅ 2 Baths ⋅ 10632439 MLS
If you’ve been looking for space, privacy, and room to spread out this one is worth a look! This 3-bedroom, 2-bath, one-story home offers 1,984 square feet and sits on 10 acres in desirable Isle of Wight County. No neighbors right on top of you - just a quiet, peaceful setting. There’s a large vinyl and Trex deck out back, perfect for relaxing or entertaining. The detached metal 2-car garage has power and water, giving you plenty of space for projects or storage. One other great convenience is the whole house generator. For animal lovers, the heated and cooled kennel includes a 30x70 chain link dog run, with a tall pole barn attached which is great for boats, equipment, or even an RV.

2215 Joyners Bridge Road, 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
$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
$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, 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
$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, 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
$400,000
10628666 MLS

8450 Windsor Boulevard, 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
$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, Isle of Wight - South
$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, 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
$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
$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, Isle of Wight - South
$370,000
4 Beds ⋅ 4.1 Baths ⋅ 10613799 MLS
Nestled on a beautiful corner lot just over an acre, this spacious brick ranch offers 4 bedrooms and 4.5 baths, along with an additional living space that could serve as a 5th bedroom. The large kitchen features generous counter space and two cooktops, perfect for meal prep and entertaining. Enjoy both a sizable living room and a comfortable family room, giving you plenty of space to spread out with more than 2,800 square feet of living area. Outside, relax on the large back deck overlooking the in-ground pool and fenced backyard. A storage shed adds convenience for yard tools and pool accessories. This property is an ideal blend of space, comfort, and outdoor enjoyment. Carrsville and Windsor School district!

31016 Walters Highway, Isle of Wight - South
$369,000
4 Beds ⋅ 2 Baths ⋅ 10615865 MLS
Welcome home to this thoughtfully updated classic 2464 sq ft 4 bedroom 2 full bath tri-level, perfectly situated on a full 1-acre lot. This home offers space, flexibility, and timeless appeal with the right mix of traditional charm and modern updates — truly move-in ready. Interior Highlights include Updated kitchen with soft-close Shaker cabinets, granite countertops, stainless steel appliances & subway-tile backsplash, Fresh interior paint (2026), New carpet padding & luxury vinyl plank flooring (2026), Upgraded lighting & fixtures, Updated electrical & plumbing (2020), New windows (2020), NewRoof (2020), New HVAC (2020) Living Spaces include Flexible floor plan with a family room/ separate den; Separate dining room ; Comfortable owner’s retreat. Step onto the rear deck overlooking an expansive one-acre yard — a place for play, pets, gardening, or simply enjoying that peaceful country feel, while still being convenient to local amenities.

31165 Walters Highway, Isle of Wight - South
$365,000
3 Beds ⋅ 2.1 Baths ⋅ 10654613 MLS

22392 Barrett Town Road, 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.