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$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, Windsor
$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, Windsor
$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, Windsor
$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, Windsor
$349,900
3 Beds ⋅ 2.1 Baths ⋅ 10598890 MLS
Welcome Home to this Spacious and Beautiful Farm House on almost 1/2 an acre Nestled in the Heart of Windsor! Renovated to Include: Soft Close Shaker Style Cabinets, Granite Counters, Tiled Back Splash, Stainless Steel Appliances, Carpet, Paint, LVP Flooring, Upgraded Lighting and Fixtures! New Roof, HVAC and Most Windows are Brand New! Owners Retreat Offers a HUGE walk in Closet, Formal Dining Room, Large Eat in Kitchen and Family Room! Detached Garage! All This A Short Distance to Ample Shopping, Dining, Entertainment and the Interstate!!

10 Church Street, Windsor
$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, Windsor
$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, Windsor
$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, Windsor
$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, Windsor
$330,000
2 Beds ⋅ 2 Baths ⋅ 10612104 MLS
FSBO

26288 Colosse Road, Windsor
$329,900
3 Beds ⋅ 2 Baths ⋅ 10588604 MLS
Welcome to this beautifully updated 3-bedroom, 2-bath rancher on a spacious lot! This home features a large remodeled interior, including a generous primary suite with private bath. Enjoy a bright, open layout with updated flooring, fixtures, and fresh paint throughout. The kitchen flows easily into the living and dining spaces, making it perfect for everyday living or entertaining. Step outside to a large back deck, small screened-in porch, and a yard with plenty of room to roam. Major updates include a new roof and new HVAC, offering peace of mind and energy efficiency. Located in a quiet neighborhood close to schools, shopping, and Route 258, this home is move-in ready and full of charm!

13067 Poor House Road, Windsor
$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, Windsor
$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, Windsor
$315,000
3 Beds ⋅ 2 Baths ⋅ 10639118 MLS
Come and make your new home in Windsor Virginia, voted the friendliest community by Nextdoor for 2026. For Sale is this approximately 1250 square foot 3 bedroom two bath Ranch home. This home sits on a .34 acre corner lot in a quite established non-HOA neighborhood. The home sits on a crawl space and has had plumbing, electrical and HVAC upgrades in the past. The property had a 16x20 one car oversized metal garage which has power and HVAC. It also has a 12x10 shed that has electricity. This home is in close proximity to retail establishments, library, and parks in town. Two Isle of Wight County schools, Windsor High and Windsor Middle, are also nearby to this home.

24129 Johnson Avenue, Windsor
$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, Windsor
$315,000
3 Beds ⋅ 2 Baths ⋅ 10606032 MLS
Step inside and feel instantly at home. This beautifully updated 3-bedroom 2-bath home is designed to bring people together with its open, bright floor plan, filled with natural light and thoughtful details. Whether it's morning coffee in the kitchen showcasing newer cabinets and counters or cozy evenings in the living room, every space invites comfort and connection. Set on 1 full acre, roof replaced 3 years ago, HVAC 3 years old, Water Heater 3 years old, well has filtration system, septic pumped and inspected 3yrs ago, crawl space inspected Aug 25, clear letter provided by Seller. Remaining updates were completed within the last 6 months, ie, whole house repaint and new trim package. This home is move-in ready.

13350 Shiloh Drive, Windsor
$310,000
3 Beds ⋅ 1.1 Baths ⋅ 10639587 MLS
This charming farmhouse sits on a generous corner lot of more than an acre and has been updated over the years with replacement windows, HVAC, an upstairs half bath, and an improved downstairs bath. The 2+ car oversized detached garage and 30x40 metal workshop/garage offer abundant workspace and storage. Located in a sought-after school district, this home offers peaceful country living just 10 minutes from Smithfield or Windsor. Truly a must-see property.

17009 Florida Avenue, Windsor
$301,000
3 Beds ⋅ 2 Baths ⋅ 10634180 MLS
Beautifully maintained and thoughtfully updated 3-bedroom, 2-bath ranch situated on a scenic and spacious 0.94-acre lot in Windsor. This inviting home features a functional open layout with a bright family room, eat-in kitchen, and a generously sized primary suite complete with a private full bath. Two additional well-proportioned bedrooms and a second full hallway bath provide plenty of space for family or guests. The oversized garage offers exceptional storage and flexibility, with ample room for vehicles, hobbies, projects, or a workshop setup. You'll enjoy the expansive backyard with peaceful country views and plenty of room to relax, entertain, or garden. Perfect for those seeking the tranquility of country living while still being conveniently close to shopping, dining, and other modern amenities. Recent updates include a new HVAC system (2024) and new gutter system (2026).

17050 Florida Avenue, Windsor
$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, Windsor
$270,000
2 Beds ⋅ 2 Baths ⋅ 10627541 MLS
Private sanctuary cabin-inspired home nestled on a lush, one acre lot. Offering the perfect blend of peaceful country living and modern convenience, this home provides breathtaking woodland views and a layout designed for effortless relaxation. Enjoy county living inside Isle of Wight County - just a quick ride to Windsor shopping and restaurants. Duel Primary Suites providing ultimate privacy and comfort for residents and guest alike. Ensuites, open to the heart of the home, open concept living space framed by large windows that bring the beauty of the outdoors inside. The living area flows onto a large wrap around back deck creating a seamless transition for living and entertaining. The roof is < 12 years old. Property includes a 400 sq ft detached garage perfect for storage, cars or woodshop. Current brown light fixture in main living space between ceiling fans does not convey. Call or text listing agent for a property website or to schedule a private tour.

13421 Shiloh Drive, Windsor
$268,000
2 Beds ⋅ 2 Baths ⋅ 10598195 MLS
Brick ranch with lots of potential. 2 BR, 2 BA with a large addition not included in the square footage. Could be sunroom, workout room or primary suite. Update to your own taste. Detached Garage & large side yard. New Replacement Windows.

24167 Lovers Lane, Windsor
$250,000
3 Beds ⋅ 2 Baths ⋅ 10620920 MLS
Come see this beautiful home located in Isle of Wight in Windsor that sits on a large corner lot! This 3 Bedroom 2 bathroom home is a must see! It has been upgraded!! LVP throughout the home. Updated kitchen with a large island! The primary bedroom has a large bathroom and walk in closet! The laundry room leads you outside to a perfect yard for entertaining! The fire pit area is a must see! Don't miss the large lot and the detached one car garage. The home features a brand new roof, with newer siding, windows and doors! You don't want to miss this home! Make it your first stop!!

17009 Mt Olive Ave, Windsor
$248,000
5 Beds ⋅ 3.1 Baths ⋅ 10611576 MLS
Come see this 5 bedroom, 3.5 bath home in Windsor with detached garage and in-law suite.

29 N Court Street, Windsor
$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, Windsor
$225,000
3 Beds ⋅ 2 Baths ⋅ 10614591 MLS

16 W Windsor Boulevard, Windsor
$199,000
2 Beds ⋅ 1 Baths ⋅ 10654705 MLS

44 W Windsor Boulevard, Windsor
$199,000
2 Beds ⋅ 1 Baths ⋅ 10654693 MLS

42 W Windsor Boulevard, Windsor
$191,000
10607727 MLS
Own the veritable Pecan 'Tree of Life'. This majestic tree is likely to harken back to the end of the Civil War. Humbly consider the ages these trees stood unwavering as the world around them turned. Imagine the possibilities that this unique property offers. Perhaps use the existing structure as the canvas for your dream home. Repurpose the rough-sawn timbers to add character and nostalgia when building your country estate. Property is aspiration- ready with a 200 amp electrical panel, deep well and existing septic system. The adjoining fields offer the potential to earn passive income thru leasing to local farmers. If you're seeking an escape from city life and yearn for a more peaceful lifestyle, plant your roots here. Bring your horses, building plans, imagination and look to the beauty and serene landscape for inspiration.

15045 Trump Town Road, Windsor
$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, Windsor
$178,000
3 Beds ⋅ 1.1 Baths ⋅ 10595195 MLS
Great Purchase Opportunity for a 3 Bedroom, 1.5 Bath Home with a Detached Garage in Town of Windsor. Home has Vaulted Ceilings that Provides an Open Concept and Versatile Floor Plan. Detached Garage with Power. Brand New Heat Pump in November, 2024. Relax on the Brick Patio in Back Yard.

24465 Curve Drive, Windsor

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.