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25092 Tyler Drive, Isle of Wight - South
$499,999
4 Beds ⋅ 2.1 Baths ⋅ 10658762 MLS
Just 5 minutes from downtown Windsor, this spacious all-brick rancher offers 4.7 acres of privacy, flexibility, and room to grow! Featuring 4 bedrooms with the option for a 5th bedroom or office, 2.5 baths, and a massive FROG, there’s plenty of space to fit your needs. Major updates include a geothermal HVAC system installed in 2024, a newer water heater and refrigerator, an approximately 8-year-old roof, and a deck replaced in 2025. The possibilities continue outside with a huge detached garage featuring potential for finished space upstairs, plus an expansive walk-in attic that could be finished for even more usable square footage. Whether you're looking for extra room to spread out, storage for hobbies and equipment, or future expansion possibilities, this property offers a rare combination of acreage, space, and convenience just minutes from town! Call today for your private showing!

25092 Tyler Drive, Isle of Wight - South
14579 Five Forks Road, Isle of Wight - South
$3,950,000
6 Beds ⋅ 5.1 Baths ⋅ 10656706 MLS
Welcome to an extraordinary 10-acre legacy estate on Lake Prince, where uncompromising luxury, craftsmanship, and natural beauty meet remarkable peace, privacy, and freedom. Architect-reimagined, every detail inspires gracious living - from warm custom lighting and whole-home audio to a chef’s kitchen with Sub-Zero towers and GE Monogram appliances. Entertain with a 1,000+-bottle wine cellar, speakeasy bar, and theater with 100” screen and 7.1 surround sound. The primary suite is a sanctuary with granite fireplace wall, panoramic views, illuminated luxury dressing room, and spa bath with soaking tub, oversized shower, and heated floors. Beyond the 6429-sf residence and guest cottage are a woodworking shop, gym, private pond and Lake Prince dock. Sunrises, wildlife, and star-filled nights unfold in extraordinary quiet. With smart-home technology, elevator, and no HOA, this rare sanctuary offers the freedom to live beautifully, entertain memorably, and create a legacy for generations.

14579 Five Forks Road, Isle of Wight - South
8529 Cut Thru Road, Isle of Wight - South
$575,000
4 Beds ⋅ 2 Baths ⋅ 10653753 MLS
Welcome to your own private retreat! This charming 4-bedroom, 2-bath home sits on approximately 2 acres and offers the perfect blend of comfortable living, privacy, and outdoor enjoyment. The inviting home features a welcoming front porch and spacious yard surrounded by mature trees. A detached garage includes a full apartment above with its own deck overlooking the backyard, offering great flexibility for guests, extended family, or additional living space. The backyard is made for entertaining with an above-ground pool, large surrounding deck, pool house, gazebo, and small fish pond. Plenty of room to relax, gather, garden, or enjoy the peaceful setting. With multiple outbuildings and versatile spaces throughout the property, this unique home offers something for everyone. Come see all this special property has to offer!

8529 Cut Thru Road, Isle of Wight - South
24408 John Henry Street, Isle of Wight - South
$325,000
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
13134 Shiloh Drive, Isle of Wight - South
$589,000
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
.47AC Holland Drive, Isle of Wight - South
$588,900
4 Beds ⋅ 2.1 Baths ⋅ 10637842 MLS
WELCOME TO THE MAYFIELD, ANOTHER FABULOUS HOME FROM SUFFOLK & ISLE OF WIGHTS PREMIER CUSTOM BUILDER. THIS 4 BEDROOM, 2 1/2 BATH HOME IS LOADED WITH THE BUILDERS STANDARD FEATURES, WHICH MOST BUILDERS WOULD CONSIDER UPGRADES. FROM THE INVITING FRONT PORCH TO THE LARGE GREAT ROOM WITH VAULTED CEILINGS, THIS HOME IS MAGNIFICENT. IF YOU ARE LOOKING FOR AN OPEN CONCEPT PLAN WITH LARGE SPACES THAT MAKE IT GREAT FOR ENTERTAINING OR FAMILY GATHERINGS, THIS IS THE HOME YOU HAVE BEEN LOOKING FOR. CALL TODAY FOR ADDITIONAL INFORMATION.

.47AC Holland 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.

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