Refine Search
Map
Sort by
16 Holland Drive, 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
14494 Bowling Green Road, Isle of Wight - South
$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, Isle of Wight - South
10419 Sylvia Circle, Isle of Wight - South
$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, 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
8450 Windsor Boulevard, Isle of Wight - South
$400,000
10628666 MLS

8450 Windsor Boulevard, Isle of Wight - South
11361 Lena Rose Street, Isle of Wight - South
$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, 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
10176 Bank Street, 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
10174 Bank Street, Isle of Wight - South
$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, Isle of Wight - South
53 Pine Lane, 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
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
24420 Lovers Lane, Isle of Wight - South
$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, 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
24 N Court Street, 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
31016 Walters Highway, 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
31165 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
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
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
105 S Court Street, Isle of Wight - South
$354,999
3 Beds ⋅ 2.1 Baths ⋅ 10619079 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. The upgraded windows and spray foam insulation make for a calm home! A designer lighting package enhances the bright, airy feel of every room. 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.

105 S Court Street, Isle of Wight - South
6043 W Blackwater Road, Isle of Wight - South
$350,000
2 Beds ⋅ 1 Baths ⋅ 10592981 MLS
Dreaming of country living? Walk into this charming brick ranch on 9.3 acres with instant Equity! With 2 cozy bedrooms and a spacious living room complete with a fireplace, it's the perfect blend of comfort and rustic charm. Bring your horses, goats, or donkeys - the fenced pasture is ready for them. Grow your own produce in the garden and enjoy fresh eggs from your chicken coops. Whether you're starting a hobby farm or just wanting room to breathe, this property is a rare find that combines functionality with rural serenity.

6043 W Blackwater Road, Isle of Wight - South
914 Wilson Road, Isle of Wight - South
$349,800
3 Beds ⋅ 1.1 Baths ⋅ 10625520 MLS
Remodeled 3 bd/2 ba home (2023) roof, siding, updated systems (electrical, plumbing, HVAC), & a converted garage w/ extra laundry & bathrooms. Kitchen has solid wood cabinets, marble counters, apron sink, stainless appliances, & a pot filler. Hardwood floors, a master suite w/ walk-in closet & bath w/double floating vanity, & heated whirlpool tub w/tiled surround. Fenced yard, decks, sheds

914 Wilson Road, Isle of Wight - South
112 S Court Street, Isle of Wight - South
$345,000
3 Beds ⋅ 2.1 Baths ⋅ 10606672 MLS
Step inside this beautifully crafted custom home featuring premium finishes typically found in luxury properties. From the moment you enter, you'll notice the 9-foot ceilings, elegant knock-down textured walls, and abundant recessed lighting that create a bright, open feel. The kitchen is a showstopper with slab granite countertops, custom cabinetry, and a full stainless-steel appliance package. Enjoy thoughtful design touches throughout — tile floors and surrounds in the bathrooms, custom vanities, and a tray ceiling in the primary suite add timeless sophistication. The attached garage provides convenience, while quality craftsmanship and attention to detail make this home stand out as one of Windsor’s best values. If you’ve been searching for move-in ready at an affordable price, look no further. Schedule your showing today!

112 S Court Street, Isle of Wight - South
6473 Pressley Way, Isle of Wight - South
$345,000
3 Beds ⋅ 2.1 Baths ⋅ 10598466 MLS
Home is 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. Pictures are of similar model. taxes to be determined

6473 Pressley Way, Isle of Wight - South
25 E Griffin Street, Isle of Wight - South
$340,000
4 Beds ⋅ 1 Baths ⋅ 10624604 MLS
This home features 4 spacious bedrooms and a large full size bathroom, home is move-in ready with thoughtful upgrades throughout. Recent improvements include some Fresh interior paint creates a bright, welcoming atmosphere, kitchen has newer appliances, kitchen cabinets and floor, some rooms have new carpet, roof only 2 years old, newer huge 2 car bay garage/workshop. Nice real hardwood floors. Backyard fenced in, two sheds for outside equipment storage. Envision the added comfort and value with the possibility of adding a full bathroom to the primary. Right in the heart of Windsor. This home will not disappoint.

25 E Griffin Street, Isle of Wight - South
24456 Walters Highway, Isle of Wight - South
$335,000
3 Beds ⋅ 2.1 Baths ⋅ 10628745 MLS
Nice 3 Bedroom, 2.5 Bath home on large corner lot. Stainless Steel Side by Side Refrigerator, Stainless Steel Range and Dishwasher. 2 car attached garage, Privacy Fenced backyard, Deck. Zoned HVAC. Convenient location for schools, employment, shopping and commuting.

24456 Walters Highway, Isle of Wight - South
12387 Old Suffolk Road, Isle of Wight - South
$330,000
4 Beds ⋅ 2 Baths ⋅ 10619973 MLS
Welcome home to this beautiful ranch-style home perfectly situated on 1.30+ acres, offering exceptional space to spread out, entertain, and enjoy peaceful outdoor living. Inside this well maintained home, you’ll find 4 good sized bedrooms and 2 full bathrooms, along with bright and welcoming living and dining areas designed for both comfortable everyday living and entertaining. The home features a tasteful blend of carpet and laminate flooring, a spacious primary owner’s suite with a double vanity, and a separate laundry room for added functionality. Step outside to a huge backyard with endless possibilities—great for hosting gatherings, gardening, or simply unwinding in your own private retreat. Conveniently located just 5 minutes from downtown Windsor, 10 minutes from the interstate, and centrally positioned near Smithfield, Suffolk, Franklin and Chesapeake. Land, space, and location—this home has it all. Schedule your private showing today and don’t miss this great opportunity!

12387 Old Suffolk Road, Isle of Wight - South
26288 Colosse Road, Isle of Wight - South
$330,000
2 Beds ⋅ 2 Baths ⋅ 10612104 MLS
FSBO

26288 Colosse Road, Isle of Wight - South
32022 Jenkins Mill Road, Isle of Wight - South
$329,999
3 Beds ⋅ 2 Baths ⋅ 10603093 MLS
This Oasis in Isle of Wight County is the perfect place to call home. This ranch on 3.86 acres is partially cleared and partially wooded. Built in 2018, Major Systems including roof and hvac are only 7 years young! This home features an open floor plan with amazing natural light, a large kitchen with island, Primary bathroom with double sinks, and freshly cleaned carpets! Get ready to call this one home!

32022 Jenkins Mill 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
11115 Dunston Drive, Isle of Wight - South
$315,000
3 Beds ⋅ 2 Baths ⋅ 10639269 MLS
Completely renovated, beautiful ranch on 1.35 acres. Country living at it's best. So quiet, yet minutes from the highway! This home boasts new siding, new roof, and new HVAC. The open brand new kitchen has granite counters and SS appliances. There are 2 living spaces as well as 2 brand new bathrooms. All new paint, flooring and lighting through out.

11115 Dunston Drive, 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.