Isle of Wight - South Homes with Wooded View

Welcome to the enchanting Isle of Wight, Virginia, a hidden gem nestled in the heart of Isle of Wight County. Known for its serene landscapes and rich history, this charming city offers a perfect blend of rural tranquility and modern conveniences. With its picturesque scenery, Isle of Wight is a haven for those seeking a peaceful lifestyle surrounded by nature.

One of the standout features of this area is the abundance of homes with wooded views. Imagine waking up each morning to the soft rustle of leaves and the gentle chirping of birds, all while enjoying the breathtaking sights of lush greenery right outside your window. These wooded properties not only provide a sense of privacy and seclusion but also create a serene backdrop for your daily life. Whether you’re sipping coffee on your porch or hosting a gathering in your backyard, the beauty of nature will be your constant companion.

Isle of Wight is also rich in historical charm, with quaint towns and vibrant communities that celebrate the area’s heritage. Residents enjoy access to local parks, outdoor recreational activities, and a welcoming atmosphere that fosters connections with neighbors. The close-knit community, combined with the stunning natural surroundings, makes Isle of Wight an ideal place to call home.

If you’re looking for a tranquil retreat with stunning wooded views, the Isle of Wight is waiting for you. Discover your dream home in this idyllic locale and experience the perfect blend of nature and community living. Your peaceful oasis awaits!

Newest Isle of Wight - South Homes with Wooded View

$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

$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

$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

$190,000

3 Beds ⋅ 1 Baths ⋅ 10649488 MLS

Great investment opportunity in Walters! Spacious 2.28acre country property offers potential for buyers looking for a renovation project, investment property or chance to bring a home back to life! This property is in fixer upper condition and will require some repairs and updates, making it ideal for someone ready to put in the work and add the value! Situated in a peaceful rural setting, the property offers plenty of potential and room to make your own. Additional room downstairs can make a 4th bedroom! Whether you're an investor looking for your next project or a buyer searching for an affordable property with possibilities, this one is worth a look!

28000 Walters Highway, Isle of Wight - South

$524,990

4 Beds ⋅ 3 Baths ⋅ 10649300 MLS

Looking for a new home and MOVE-IN READY! This is the one! Welcome to The Cypress at Windsor Station where modern sophistication meets timeless charm. This thoughtfully designed 4-bedroom, 3-bathroom home offers incredible flexibility, featuring a desirable first-floor guest suite and an open gourmet kitchen equipped with a central island, upgraded quartz surfaces, and gas range. Upstairs, a massive loft creates the perfect space for a media room or play area. The second floor also hosts a private primary retreat to include upgraded luxury shower with glass doors en suite, two additional bedrooms, guest bath with double bowl sinks and a dedicated laundry room. Warm wood tones, elegant stone counters, and classic cabinetry bring a refined, cohesive feel to every room. Enjoy Windsor's small-town charm with rapid access to Route 460, local dining, and shopping. Receive up to $15,000 in closing costs when using the seller's approved lender. Schedule your tour today!

12169 Ava Lane, Isle of Wight - South

$605,000

4 Beds ⋅ 2.1 Baths ⋅ 10648830 MLS

The one you've been waiting for! Your very own country oasis situated on 3.62 acres of land just 15 minutes from Downtown Smithfield/Mainstreet. Home features a formal dining room, beautifully updated kitchen with eat in area, as well as a huge living room with built-in bookshelves. Enjoy quiet evenings on the large back deck, or morning coffee on the wrap around front porch. In addition to the 2 car attached garage the property also features a large detached 5 car covered storage shed, and 2 car enclosed metal storage building with 9k pound auto lift and additional electric panel. New deep water well installed late 2023. This updated home is ready for a new family!

17479 Courthouse Highway, Isle of Wight - South

$572,000

4 Beds ⋅ 3.1 Baths ⋅ 10647835 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—while a full bath adds extra functionality. $$$ Builder offering $15,000 in CCA, plus an additional $10,000 in flex dollars, to be used for upgrades or interest rate buy down on your mortgage. $$$ Call today and be settled into your new home just in time to enjoy summer! **MOVE IN READY** NEW CONSTRUCTION! ** Some photos are of staged model.

12236 Ava Lane, Isle of Wight - South

$452,999

5 Beds ⋅ 3 Baths ⋅ 10647506 MLS

Welcome home to this beautiful new construction offering country living but minutes from shopping, dining, schools and daily commuting. Situated on a .25-acre lot, this beautifully designed home offers 5 bedrooms, 3 full baths, and an open concept layout for everyday living and entertaining. A 2 car garage provides plenty of space for parking, storage or hobbies. Don't miss your opportunity to own a beautiful new home with modern finishes in a quiet convenient location. Everything is brand new, giving you piece of mind and low maintenance. The only thing missing is you! Schedule your personal showing today!

14160 Booker T Drive, Isle of Wight - South

$275,000

3 Beds ⋅ 1 Baths ⋅ 10647162 MLS

Well-maintained, move-in ready, brick ranch situated on a spacious country lot with an additional parcel included! Recent updates include beautiful, refinished hardwood floors, fresh paint in & out, new metal roof, new windows, new well, and new kitchen appliances. The large kitchen provides plenty of cabinet and counter space, while the in-unit laundry adds everyday convenience. Outside, you'll find both an attached carport and a detached garage, offering ample parking, storage, or workshop space. Enjoy the privacy of country living while remaining just a short drive from shopping, dining, major highways and other amenities. A great opportunity for anyone looking for a starter or downsizer home with valuable updates and plenty of outdoor space!!

32229 Walters Highway, Isle of Wight - South

$539,000

4 Beds ⋅ 3 Baths ⋅ 10647159 MLS

Welcome to Windsor Station. Built by Taylor Construction. Move Into Your Brand-New Home Before the End of the Year! Introducing the stunning Paloma Ranch model, thoughtfully designed with timeless Craftsman-style architecture and modern finishes throughout. Scheduled for completion before the end of the year, this beautiful new construction home offers the perfect combination of style, comfort, and functionality. Inside, you'll find durable LVP flooring throughout the main living areas and a spacious open-concept layout ideal for everyday living and entertaining. This home features the optional 4th bedroom, including a luxurious first-floor primary suite with a beautifully tiled walk-in shower and generous walk-in closets. The kitchen offers granite countertops, stainless steel appliances, and flows seamlessly into the dining and family rooms, creating the perfect gathering space for family and friends. $$$ Builder offering $15,000 in CCA, plus an additional $10,000 in flex dollars, to be used for upgrades or interest rate buy down on your mortgage. $$$ *Pics are images of the proposed finished project and some items are subject to change.

12343 Ava Lane, Isle of Wight - South

$639,990

6 Beds ⋅ 3.1 Baths ⋅ 10643947 MLS

Welcome to The McDowell by Eastwood Homes at Windsor Station, a stunning two-story home designed for comfort, space, and modern living. This four-bedroom, 3.5-bath layout features a sought-after first-floor primary suite, elegant formal dining room, and a dramatic two-story family room that flows into a chef-inspired kitchen with island, pantry, and bright breakfast area perfect for everyday living and entertaining. Upstairs offers three spacious bedrooms, two full baths including a convenient Jack-and-Jill layout and an expansive loft ideal for relaxing, working, or gathering. Personalize your dream home with options like a designer kitchen with butlers pantry, guest suite or private office, sunroom or covered porch, media room, or even a second primary suite. Enjoy small-town charm in Windsor with easy access to Route 460, shopping, and dining crafted for the way you live today.

12242 Ava 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.