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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

$565,000
3 Beds ⋅ 3 Baths ⋅ 10596299 MLS
Custom-built and thoughtfully designed, this 3-bedroom, 3-bath home blends modern efficiency with serene country living. Featuring a beautifully remodeled bathroom, heated tile floors, and energy-saving geothermal heating and cooling, comfort is built into every detail. The spacious primary suite offers a handicap-accessible American Standard Liberation Tub for easy, spa-like relaxation. Outdoor enthusiasts will love the saltwater inground pool and 9.5+ wooded acres—perfect for hiking, fishing, hunting, or simply enjoying nature in total privacy. A 1,500 SF detached garage provides ample space for storage, hobbies, or a full workshop. Plus, the large unfinished walk-in attic holds incredible potential to be converted into a 4th bedroom, office, or bonus room. This rare property combines privacy, luxury, and functionality—ideal for anyone seeking peaceful living with room to grow. Come experience the best of both comfort and the outdoors!

6728 Mill Creek Drive, Isle of Wight - South

$560,000
4 Beds ⋅ 3 Baths ⋅ 10617899 MLS
Beautifully updated 4-bedroom, 3-bath home with over 3,000 sq. ft on 3.55 peaceful acres! Features include fresh paint, new carpet, updated light fixtures, outlets, and switches, plus gorgeous hardwood floors downstairs. The spacious layout offers a large FROG with walk in closet—perfect as a bonus room, office, or guest suite. Outside, enjoy a detached garage with workshop, one-stall stable with additional storage, hay hut, chicken coop, and a partially wooded lot that provides space and privacy with a large in-ground pool with covered pergola to relax on summer days. The property also boasts fruit trees and berry plants, including 2 peach, 3 Granny Smith apple, strawberries, 1 blueberry, about 10 blackberries, and 7 raspberries and 1 fig tree. A rare find combining modern updates, country charm, and room to grow! Don't miss the opportunity to call this your new home!

7013 Mill Creek Drive, 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

$544,000
3 Beds ⋅ 2 Baths ⋅ 10595064 MLS
Custom built brick beauty on 6 acres! Discover comfort, privacy and charm in this beautiful crafted 3 bedroom, 2 bath brick home nestled on 6 serene acres. Custom built offers timeless elegance with gleaming wood floors & plantation blinds. The heart of the spacious eat-in-kithen, great for family meals or entertaining. Adjoining dining room offers extra space for gatherings and holidays. Primary suite is a true retreat featuring jetted soaking tub, ceramic flooring, double vanity and huge walk in closet. The attic has 1300 undeveloped sq ft in the walk up attic, permanent stairs and floored- great for storage or future expansion. All brick exterior for durability & low maintenance. Peaceful wooded surroundings offering space & seclusion. Don't miss your chance to own this beautiful blend of comfort and country living in the Carrsville School District!

29139 Holly Run 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

$490,000
3 Beds ⋅ 2.1 Baths ⋅ 10597385 MLS
Discover your new home in Isle of Wight County, Virginia, where this charming 3-bedroom, 2.5-bathroom residence spans 1,792sqft on a sprawling 14.961-acre lot. Great for those craving serene country living, it’s just 25 minutes from Wakefield, Smithfield, and the greater Hampton Roads area. The open-concept first floor features an open kitchen with a pantry, full appliances, and a breakfast area leading into the living room. A bonus room and half bath add flexibility multiple uses. Upstairs, the 16x16 primary bedroom offers an ensuite with dual vanities, a jetted tub, and a tiled shower. Two additional bedrooms (12x12 and 12x10) and a full bathroom provide ample space. A 437sqft attached garage adds convenience. Outside, a serene pond and towering oaks create a picturesque front yard, while the vast acreage is greatl for a farmette, gardening, or hunting. Storage includes a 9x16 metal shed, a 20.5x18 carport, and a 23x13 workshop with a wood-burning stove, porch, and covered storage.

15316 Rattlesnake Trail, Isle of Wight - South

$480,000
4 Beds ⋅ 2.1 Baths ⋅ 10598484 MLS
If you’ve been dreaming of a little more space and a lot more peace, this charming country home might be just what you’ve been waiting for. Nestled on 1.5 acres, this 2,516 sq ft retreat offers plenty of room to spread out while still feeling cozy and welcoming. With 4 spacious bedrooms, 2.5 bathrooms, and a first-floor primary suite with private en-suite bath, comfort comes naturally. A main-level laundry room adds convenience, while a wood-burning fireplace and an additional electric fireplace create warmth and character. You’ll also find an office, a rec room, ceiling fans throughout, and high-speed internet to keep you connected. Recent updates include a new roof (2017) and HVAC (2020). Outside, enjoy a large detached garage/workshop, plus RV storage with electric and septic hookups. Tucked away on a private lane and surrounded by nature, this home is the perfect blend of charm, comfort, and modern updates.

26413 Sparrow Lane, Isle of Wight - South

$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, Isle of Wight - South

$475,000
4 Beds ⋅ 2.2 Baths ⋅ 10605408 MLS
Beautifully updated Cape Cod on 1.24 acres of peaceful country living! This 4-bedroom, 2 full & 2 half-bath home features a flowing & flexible main living area with a formal dining that can easily be an office, large great room w/cozy fireplace open to the eat in kitchen & cooking area for entertaining. The FROG is the 4th bedroom. Enjoy a brand-new kitchen w/updated cabinets, counters, flooring, & appliances. Fresh paint throughout & some new flooring. The large primary suite includes a walk-in closet & private bath. A convenient mudroom off the garage has a washer, dryer, & half bath. 2 car side loading garage & plenty of parking for all your toys! Relax or entertain by the above-ground pool with oversized deck—perfect for enjoying starlit country nights. Pool recently closed by Oliver Pools. Easy 45-minute commute to Petersburg, Richmond, or Virginia Beach via Route 460. Welcome Home!

7363 Mill Creek 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

$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, 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

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.