Isle of Wight - South Real Estate

Welcome to the enchanting Isle of Wight, Virginia, a hidden gem nestled in the heart of Isle of Wight County. This charming region is steeped in history and natural beauty, making it an ideal location for those seeking a serene lifestyle with a touch of Southern charm.

Isle of Wight is known for its picturesque landscapes, including lush forests, rolling hills, and the stunning shores of the James River. Residents enjoy a peaceful ambiance, with ample opportunities for outdoor activities such as hiking, fishing, and boating. The area's rich natural resources provide a perfect backdrop for family picnics, weekend getaways, or simply unwinding after a long day.

History enthusiasts will appreciate the county's deep roots, with landmarks dating back to the 17th century. The Isle of Wight County Museum offers a glimpse into the past, showcasing artifacts and exhibits that tell the story of this vibrant community. The historic town of Smithfield, located nearby, is famous for its charming streets, delightful shops, and the iconic Smithfield Ham.

The community is also known for its friendly atmosphere and strong sense of belonging. With a mix of local businesses, schools, and recreational facilities, Isle of Wight offers a nurturing environment for families and individuals alike.

Whether you’re drawn to the stunning landscapes, rich history, or the warm community spirit, Isle of Wight, Virginia, is a place where you can truly feel at home. Explore the possibilities of living in this delightful area and discover the perfect blend of tranquility and tradition.

Newest Listings in Isle of Wight - South

$375,000

3 Beds ⋅ 2.1 Baths ⋅ 10652037 MLS

Sitting on over half an acre, this upcoming new construction home offers a lot size that's hard to come by and plenty of room to grow into. Featuring granite countertops throughout, tray ceilings that add an elegant touch, and stainless steel appliances in the open kitchen. With 3 bedrooms, 2.5 bathrooms, a 1-car attached garage, and 1,616 sq ft of living space, it's the perfect blend of modern convenience and style. Purchase without the worry of repairs. Don't miss out on the opportunity to make this your dream home! *Pictures of like model. House is currently being built.

6295 Carrsville Highway, Isle of Wight - South

$434,900

4 Beds ⋅ 2.1 Baths ⋅ 10652786 MLS

Welcome to Holland Meadows! This beautifully maintained 4-bedroom, 2.5-bath home with a 2-car garage offers the perfect blend of space, comfort, and style. The open-concept floor plan is ideal for both everyday living and entertaining, featuring granite countertops, stainless steel appliances, and abundant living space. The spacious primary suite boasts a large walk-in closet and a private bath with double vanities and an oversized walk-in shower. Generously sized secondary bedrooms complete the upstairs space. Step outside and enjoy peaceful wooded views from the private fully fenced backyard, creating the perfect retreat at the end of the day. Just minutes from downtown Windsor. Don't miss your opportunity to make this beautiful home yours!

12015 Lena Rose Street, Isle of Wight - South

$225,000

3 Beds ⋅ 2 Baths ⋅ 10652506 MLS

Get in touch with country living with this 3 bedroom, 2 bath home. Add your personal touches & get your garden started. Convenient location to Tidewater area EZ commute. Top rated Carrsville Elementary School located only a few miles away. Priced to sell ! Please compare to what's available in this price range. No restrictions on use of land other than public ordinances-say goodbye to HOAs. Sit our in your own yard and star gaze with maybe a bon fire cooking hot dogs on a stick over the open fire. Blackwater river which is a scenic river located only a few miles away with a public launch area in Franklin (about 10 miles).

10007 Old Myrtle Road, Isle of Wight - South

$425,000

4 Beds ⋅ 2 Baths ⋅ 10651468 MLS

Sold as Is - Where Is, Seller to make no repairs. Fixer upper with tons of potential. Located at the end of a culdesac in beautiful Holland Meadows backyard facing woods. Utilities are off. Buyers responsibility to turn utilities on/off if interested for inspection. Mechanics in the home may or may not work, seller is unsure as it was tenant occupied. Will not qualify for VA/FHA. Cash or renovation loans only.

24408 John Henry Street, Isle of Wight - South

$439,900

4 Beds ⋅ 2.1 Baths ⋅ 10651476 MLS

Come out to the country! You will enjoy country living in this beautiful home with 4 bedrooms, 2 1/2 baths, private primary bedroom and bathroom downstairs. Tankless water heater, new HVAC installed in 2025, oak hardwood flooring, granite counter tops in kitchen, solid wood kitchen cabinets, open floor plan, vaulted ceilings in family room and large screened porch. Barn in back of home will be sold "As Is condition.

19428 Tomlin Hill Drive, Isle of Wight - South

$609,000

3 Beds ⋅ 2.1 Baths ⋅ 10650991 MLS

Country living at its finest! Beautiful home located on 1 acre; conveniently located near Hwy 460 for an easy commute to anywhere in Hampton Roads. This home is ready for entertaining with a salt water inground pool, fire pits, gazebo, and composite deck off of the back of the home. Inside the home you'll find an open floor plan downstairs with a lovely family room, open to a spacious kitchen with stainless steel appliances, separate dining room, large bedrooms w/ 1st floor large primary en-suite. Upstairs is a large finished room with endless opportunities for more entertainment with a pool table, area for watching your favorite sports, perfect for a home school family to have a library and plenty of space for learning and activities, or perfect space for your favorite hobbies. This is a home you do not want to miss seeing. Schedule your appointment TODAY!!!

13134 Shiloh Drive, Isle of Wight - South

$589,900

4 Beds ⋅ 3.1 Baths ⋅ 10651093 MLS

WELCOME HOME TO THE KESTREL RANCH IN WINDSOR! Discover the perfect blend of small town charm, modern comfort and beautiful new construction, all with convenient access to Suffolk, Smithfield and the greater Hampton Roads area. This thoughtfully designed home features shaker style cabinetry with soft close doors and drawers, granite countertops, tile backsplash, double wall ovens, luxury vinyl plank flooring and a cozy fireplace with built ins. The spacious primary suite offers a beautifully tiled walk in shower, while two additional bedrooms are conveniently located on the first floor. Upstairs, a private second living room area and the fourth bedroom with full bath creates the perfect space for guests, family or a home office. Situated on a oversized homesite, enjoy outdoor living from the covered rear porch and patio.

12185 Ava Lane, Isle of Wight - South

$405,000

4 Beds ⋅ 2.1 Baths ⋅ 10650799 MLS

Welcome home to 316 A Pocahontas Ave, where modern luxury meets warm, everyday comfort. Built in 2023 with over $17,000 in builder upgrades, this 4-bedroom, 2.5-bath sanctuary is completely move-in ready and conveniently located minutes from major regional employers, Downtown Franklin, and US-58.Step inside to an open layout with 9-foot ceilings, crown molding, and durable LVP hardwood floors. Unwind under elegant coffered ceilings, or gather in the gourmet kitchen showcasing 42-inch soft-close cabinets, granite countertops, a tile backsplash, and stainless steel appliances.Upstairs, your primary suite serves as a peaceful retreat with vaulted ceilings, his and her closets, dual vanities, a jetted tub, and a walk-in shower. The second full bathroom in the hallway also features its own dual vanity, making morning routines effortless for family and guests. Outside, relax or host friends on your private 10' x 12' deck. Schedule your tour today!

316 A Pocahontas Avenue, Isle of Wight - South

$60,000

3 Beds ⋅ 2 Baths ⋅ 10650676 MLS

Investor special! Value in the land. Sold AS-IS, WHERE IS. Seller to make no repairs. Sign hold harmless prior to showing. Property being sold by a court ordered and approved conservator.

9324 Windsor Boulevard, Isle of Wight - South

$429,900

3 Beds ⋅ 2 Baths ⋅ 10650453 MLS

Welcome to your Zuni retreat at 19251 Tomlin Hill Dr! This beautifully updated 3 bedroom, 2 bathroom home blends modern comfort with an incredible outdoor lifestyle. Inside, enjoy a bright kitchen with a farmhouse sink, vaulted ceilings in the primary bedroom, a home office with built-ins. New can lights installed (2024). Big-ticket items are completely covered: brand-new HVAC & mini-split (6/2026), new water heater (2/2020), and an upgraded septic/drainfield (2019). The massive detached garage boasts polished concrete floors. Entertain effortlessly in your backyard oasis! The re-decked back porch with new stairs/railings (2023) flows into a gorgeous pergola (2020) and a brand-new outdoor bar/cooking area (2025). Surrounded by nature, you'll be greeted by unique wildlife like otters, turtles, frogs, and birds right in your own yard. This home is fully turnkey and ready for its next chapter. Schedule your tour today before it's gone!

19251 Tomlin Hill Drive, Isle of Wight - South

$599,000

4 Beds ⋅ 3.1 Baths ⋅ 10650017 MLS

Welcome to Windsor Station! Built by Taylor Construction, this stunning Helena model is now move-in ready and showcases beautiful Craftsman-style details from the exterior through every inch of the home. Inside, you’ll find durable LVP flooring throughout the main living areas and a thoughtfully designed layout featuring 4 bedrooms, including a spacious primary suite with a tile shower and walk-in closets. The open-concept kitchen is perfect for entertaining, complete with granite countertops, stainless steel appliances, and a seamless flow into the family and dining areas. The first floor also includes a convenient half bath and a versatile flex room, ideal for a home office or additional living space. Take advantage of closing cost assistance when using the preferred lender and settlement company. Call today and be settled into your new home just in time to enjoy the fall. MOVE IN READY ** NEW CONSTRUCTION! $$$ Builder offering $15,000 in CCA, plus an additional $10,000 in flex dollars, to be used for upgrades or interest rate buy down on your mortgage. $$$

12163 Ava Lane, Isle of Wight - South

$405,000

3 Beds ⋅ 2 Baths ⋅ 10650026 MLS

Built in 2015 with a 3rd bedroom conversion later, the home and setting is awesome! Country living with all the feel of a new modern day home. Just under 6 acres, the home is ready and don't forget your farm animals. The property is fully fenced around the perimeter and into 4 sections making it easy to divide the animals if needed. You can let your dog out to roam free in the entire yard! Abundant wildlife throughout as much of the trees on the property consist of mature white and red oaks. Private Road access off of Highway 460 and just minutes from local stores. Rare opportunity for a newer home with acreage. Goat shed & pen, dog pen and chicken house & pen. Feed shed, well shed Playset conveys. Covered back porch, Peach, Apple & Pear trees. Granite counter tops in kitchen and too many other feature and items to list.

21483 Chestnut Lane, Isle of Wight - South

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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.