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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
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
4393 Cox Street, Isle of Wight - South
$217,000
3 Beds ⋅ 1 Baths ⋅ 10626921 MLS
Great Home in Quiet and Established Community of Walters. Served by Desired Windsor & Carrsville School Districts. Move In Ready with Newly Remodeled and Updated Kitchen & Bathroom. New Carpet in Spacious Living Room & Bedrooms Over Wood Floors. Laundry / Mud Room Provides Good Additional Space. Vinyl Replacement Windows. Relax on the New Front Porch or Rear Patio. 18' x 20' Concrete Block Detached Garage / Workshop. Fenced In Backyard & Deep Well.

4393 Cox Street, Isle of Wight - South
TBD W Norfolk & Western Street, Isle of Wight - South
$159,000
10626137 MLS
B-1 Zoned Parcel with a Commercial Building in the Town of Windsor with Visibility and Exposure to Windsor Blvd (Highway 460). Near a Busy 6 Way Stoplight Intersection. Building has 2 Bay Doors, 2 Passage Access Doors & an Office Area. The Portion of the Lot Fronting on Norfolk & Western Street is Fenced. Adjoining & Other Businesses in Area Include Gas Station/Convenience Store, Professional Offices, Hair & Tanning Salon, Restaurants, Retail, Car Wash, Laundromat, Self Storage & Hardware Store. Great Purchase Opportunity for a Variety of Business Uses in a Growing Community.

TBD W Norfolk & Western Street, Isle of Wight - South
32033 Jenkins Mill Road, Isle of Wight - South
$177,500
3 Beds ⋅ 1 Baths ⋅ 10624590 MLS
This home is nestled on an acre lot in a rural setting and within the sought out Carrsville Elementary School district! It features 3 bedrooms, 1 bathroom, vinyl replacement windows, eat-in kitchen, and a new water heater. This property offers a blank slate, so you can easily make it your own! The home is being sold strictly as is, but any lender required repairs will be considered. Call today to schedule a showing!

32033 Jenkins Mill Road, Isle of Wight - South
15.9AC Ecella Road, Isle of Wight - South
$180,000
10615184 MLS
Discover nearly 16 acres of pristine farmland, the perfect canvas for your custom dream home or a premier equestrian estate. This expansive lot is mostly cleared and ready for development, featuring mature tree lines on two sides for natural privacy. Experience the quintessential peace and tranquility of country living without sacrificing convenience; you are located just off Rt. 460, less than 7 minutes from Windsor’s schools and shops, and only 22 minutes from the charm of Smithfield. With an easy commute to local military bases and major hubs like Chesapeake, Newport News, and Petersburg in under an hour, this property offers the best of rural serenity and city accessibility.

15.9AC Ecella Road, Isle of Wight - South
54 Pine Lane, Isle of Wight - South
$315,000
3 Beds ⋅ 2 Baths ⋅ 10627016 MLS
Welcome to this charming 3-bedroom, 2-bath brick rancher in the heart of Windsor, VA! Situated on a 0.42-acre end-of-street lot, this move-in-ready home offers 1,557 sq. ft. of comfortable living space. Highlights include a spacious, light-filled sunroom overlooking a private, fenced backyard-perfect for relaxing or entertaining. This well-maintained home features a 1-car attached garage, pull-down attic stairs for extra storage, a functional whole house fan, and the convenience of public water and sewer. Located in the sought-after Isle of Wight County school district, you are minutes from local parks, shopping, and dining. Enjoy the best of small-town living with a seamless commute to Suffolk, Smithfield, and the greater Hampton Roads area via Rt. 460 and Rt. 258. This property offers the ideal blend of classic character and modern ease. Schedule your private tour today and see why life is better in Windsor!

54 Pine Lane, Isle of Wight - South
30174 Walters Highway, Isle of Wight - South
$250,000
3 Beds ⋅ 1 Baths ⋅ 10625720 MLS
Newly Renovated Brick Ranch with Attached Carport offering the serene view of farm land surrounding the home. Home has Deep Well, Septic System, Electric, HVAC, Windows, Foundation Vents, Kitchen, Bathroom, Flooring, Water Heater, Gutter Guards, Rear Deck all updated in 2024.Easy commute and only min to schools and shopping. Located in the Carrsville Elementary & Windsor High School Districts. This home is an absolute gem and offers an additional den or 3rd bedroom. This home is Move in Ready!

30174 Walters Highway, 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
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
203 Council Road, Isle of Wight - South
$165,000
3 Beds ⋅ 2 Baths ⋅ 10617464 MLS
Welcome to the cozy 3 bedroom, 2 bathroom ready for its new owner. Perfect as a starter home or an investment property, this property offers comfort and potential. Schedule your private showing today.

203 Council Road, Isle of Wight - South
1379 Moonlight Road, 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
8450 Windsor Boulevard, Isle of Wight - South
$400,000
10628666 MLS

8450 Windsor Boulevard, 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
11492 Savannah Street, 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
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
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
20460 Sand Pit Road, Isle of Wight - South
$111,000
3 Beds ⋅ 2 Baths ⋅ 10593080 MLS
Your opportunity to escape the city and own your own home on approximately 2.53 acres in the peaceful area of Zuni. The home is set back off the road and surrounded by trees and nature. This home offers 3 bedrooms, 2 bathrooms, 1600 sq ft of living space with a gas fireplace in the family room and decorative wall dividers throughout providing a look of elegance. The primary bedroom offers a large bathroom with double sink vanities, soaking tub and a separate shower. Off of the Family Room you will find the Sunroom and also a screened in porch to the side of house. Case# 541-738561 IE (Insured Escrow) Subject to Appraisal. Property is Owned by the US Dept. of HUD. Seller makes no representations or warranties as to the property condition. HUD Homes are Sold "AS IS". Equal Housing Opportunity. Seller may contribute up to 3% for buyers closing costs upon buyer request.

20460 Sand Pit Road, Isle of Wight - South
40 Holland Lane, Isle of Wight - South
$275,000
2 Beds ⋅ 1 Baths ⋅ 10623729 MLS
Charming brick ranch filled with ample natural light. The home offers a spacious living room, a cozy family room with fireplace, and an eat-in kitchen. The floorplan provides a great flow for everyday living and entertaining. Outside, enjoy a huge yard and a large detached garage offering plenty of room for storage, or hobbies. Schedule your private tour today!

40 Holland Lane, Isle of Wight - South
31242 Holly Run Drive, Isle of Wight - South
$302,000
10603712 MLS
Great opportunity for 22.69 acres within Isle of Wight County. Build your dream home on this large property with the ability to house horses and livestock, or use it for recreational purposes. With over 530 feet of state road frontage, nearly 16 acres of cropland, and the remainder in towering pines and mixed hardwoods, it allows for numerous options on how you can enjoy this acreage. Great residential and recreational value. Close proximity to Franklin and Windsor where you can enjoy restaurants and shopping.

31242 Holly Run Drive, 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
23227 Stave Mill Road, Isle of Wight - South
$150,000
2 Beds ⋅ 1 Baths ⋅ 10624403 MLS
Great Purchase Opportunity for a Starter, Retirement Home or Investment Property. Home Sits on a 1 Acre Lot with Mature Woods on Rear of the Property and it is Served by a Deep Well. Located Just Outside the Town of Windsor and Convenient to Many Amenities in the Area. Home has Vinyl Replacement Windows and a Heat Pump.

23227 Stave Mill Road, 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
24401 John Henry Street, Isle of Wight - South
$445,000
4 Beds ⋅ 3.1 Baths ⋅ 10613338 MLS
Lovely 4 bedroom 3.5 bathroom home located in the Holland Meadows neighborhood of Windsor. IN-Ground Swimming pool / Salt water / located in a cup-de-sac / white vinyl back yard. You will love the home and the neighborhood! Items to convey - all items to include all appliances to include the washer and dryer, 8'/8' garden shed . Tile showers / Granite island and vanities. electric fire place in great room. Windsor school system.

24401 John Henry Street, Isle of Wight - South
Lot 23 Lovers Lane, Isle of Wight - South
$60,000
10622931 MLS
This vacant residential lot offers the perfect opportunity to create a custom home in an established neighborhood with a peaceful, small-town atmosphere. Enjoy paved road frontage and convenient access to local schools, shopping and commuter routes to the greater Hampton Roads area. Whether you're ready to build now or planning for the future, this property provides the ideal setting to bring vision to life.

Lot 23 Lovers Lane, Isle of Wight - South
8480 Green Level Road, Isle of Wight - South
$68,000
4 Beds ⋅ 1 Baths ⋅ 10614666 MLS
This could be your opportunity to own a home in the Ivor area. The property needs TLC but has great potential. Enjoy country living in this quaint home on close to 3/4-acres. With 4 bedrooms and 1 bathroom this open concept living room/ kitchen could be yours. Case#541-958970 IE (Insured Escrow) Subject to Appraisal. Property is Owned by the US Dept. of HUD. Seller makes no representations or warranties as to the property condition. HUD Homes are Sold "AS IS". Equal Housing Opportunity. Seller may contribute up to 3% for buyers closing costs upon buyer request.

8480 Green Level Road, Isle of Wight - South
18423 Tomlin Hill Drive, Isle of Wight - South
$300,001
10615182 MLS
Amazing 34 acres of pristine farmland, the perfect site for your custom dream home or a premier equestrian estate. This expansive lot is mostly cleared and ready for development, featuring mature tree lines for natural privacy around the property. Experience the quintessential peace and tranquility of country living without sacrificing convenience; you are less than 10 minutes from Windsor’s schools and shops, and only 20 minutes from the charm of Smithfield. With an easy commute to local military bases and major hubs like Chesapeake, Newport News, and Petersburg in under an hour, this property offers the best of rural serenity and city accessibility. Enjoy starlit nights that surpass planetarium skies and no traffic noise! Welcome home to the country life!

18423 Tomlin Hill Drive, Isle of Wight - South
30715 Hunt Club Road, Isle of Wight - South
$245,000
3 Beds ⋅ 2 Baths ⋅ 10618052 MLS
Welcome to peaceful country living. This 3 bed/2 bath ranch-style home sits on a spacious half-acre lot, offering a great blend of privacy, comfort, & convenience. Inside you'll find a functional single-level layout w/comfortable living spaces superb for everyday living or entertaining. The generous lot provides plenty of room to enjoy the outdoors. This home offers a quiet, rural feel while still providing easy access to nearby towns, highways, and everyday essentials. A few of the new things are: Central HEAT/AC-2020, Roof-2020, Well Pump-2024 Don't miss the opportunity to make this your home!

30715 Hunt Club Road, Isle of Wight - South
18 B Avenue, Isle of Wight - South
$230,000
10601198 MLS
Calling all investors and house hackers! This duplex is a fantastic opportunity for an investor or a buyer looking to build equity through renovations. This property is ready for its next chapter and offers incredible potential. Perfect for someone willing to put in the work, this property is being sold as-is, where-is, with the sellers making no repairs. The location is ideal in the heart of Windsor, just within a mile of restaurants, shopping, and veterinary care, making it a convenient and desirable area. Whether you’re looking for your next project or a home to make your own, this is a great chance to create something special. Don’t miss out on this opportunity!

18 B Avenue, Isle of Wight - South
23068 Andrew Court, 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

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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