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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

11558 Savannah Street, Isle of Wight - South
$529,900
4 Beds ⋅ 3.1 Baths ⋅ 10658273 MLS
Ready Mid-December + $10,000 Flex Cash! The Goldfinch at Windsor Station by Ashdon Builders offers 4 bedrooms, 3.5 baths, approx. 2,411 sq ft and a 2 car garage. Inside, Graphite and Greystone kitchen cabinetry pairs with Pure White quartz countertops, matte black hardware, and stainless-steel appliances. Luxury vinyl plank flooring flows through main living areas. Enjoy spacious living & dining areas, a kitchen pantry, convenient laundry room, 9-foot ceilings, and an electric fireplace with white floating mantel, soft close shaker style kitchen cabinetry, under cabinet lighting, and a tiled primary shower. Energy efficient construction and a builder warranty provide peace of mind. For a limited time, receive $10,000 Flex Cash with use of the preferred lender and settlement agent. Located in Windsor, enjoy small-town charm, local community events, and a relaxed pace of life with convenient access to Suffolk, Smithfield, and greater Hampton Roads.

11558 Savannah Street, 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

MM Goldfinch, Isle of Wight - South
$519,900
4 Beds ⋅ 3.1 Baths ⋅ 10654595 MLS
TO BE BUILT, Goldfinch MODEL AT WINDSOR SATION! Starting at $519900. Build your dream home and personalize it to fit your lifestyle. The Goldfinch offers 3 to 4 bedrooms, 2.5 to 3.5 baths, approximately 2411 to 2735 square feet, and a 2 car garage and the option to add a multi Gen Suite with spacious living and dining areas, kitchen with pantry, and laundry room. Optional second floor configurations provide additional living space, a loft, that can be turned into a fourth bedroom, and full bath. Standard features include 9 foot ceilings, electric fireplace, LVP flooring in main living areas, shaker style soft close kitchen cabinetry, quartz countertops, under cabinet lighting, stainless steel appliances, primary bath tile shower, and a 2 car garage. Energy efficient construction and builder warranty included. Choose your homesite, select your finishes, and make the Kestrel your own at Windsor Station. Pricing reflects base home and is subject to change. Options and upgrades may be additional. Please call today for your private tour.

MM Goldfinch, Isle of Wight - South

MM Kestrel, Isle of Wight - South
$499,900
4 Beds ⋅ 3.1 Baths ⋅ 10654591 MLS
TO BE BUILT, KESTREL MODEL AT WINDSOR STATION! Starting at $499,900. Build your dream home and personalize it to fit your lifestyle. The Kestrel offers 3 to 4 bedrooms, 2.5 to 3.5 baths, approximately 1,979 to 2,619 square feet, and a 2 car garage. The thoughtfully designed first floor features the primary suite plus two additional bedrooms, spacious living and dining areas, kitchen with pantry, and laundry room. Optional second floor configurations provide additional living space, a loft, fourth bedroom, and full bath.Standard features include 9 foot ceilings, electric fireplace, LVP flooring in main living areas, shaker style soft close kitchen cabinetry, quartz countertops, under cabinet lighting, stainless steel appliances, primary bath tile shower, and a 2 car garage. Energy efficient construction and builder warranty included. Choose your homesite, select your finishes, and make the Kestrel your own at Windsor Station. Pricing reflects base home and is subject to change. Options and upgrades may be additional. Please call today for your private tour.

MM Kestrel, Isle of Wight - South

MM Wrenfield, Isle of Wight - South
$589,900
4 Beds ⋅ 3.1 Baths ⋅ 10654581 MLS
TO BE BUILT, Wrenfield MODEL AT WINDSOR SATION! Starting at $589900. Build your dream home and personalize it to fit your lifestyle. The Wrenfield offers 4 to 6 bedrooms, 2.5 to 3.5 baths, approximately 2844 to 2997 square feet, and a 2 car garage and the option to add a 1 fl bedroom /w bath and spacious living and dining areas, kitchen with pantry, and laundry room. Optional second floor configurations provide additional bedroom and full bath that can be added. Standard features include 9 foot ceilings, electric fireplace, LVP flooring in main living areas, shaker style soft close kitchen cabinetry, quartz countertops, under cabinet lighting, stainless steel appliances, primary bath tile shower, and a 2 car garage. Energy efficient construction and builder warranty included. Choose your homesite, select your finishes, and make the Wrenfiled Model your own at Windsor Station. Pricing reflects base home and is subject to change. Options and upgrades may be additional. Please call today for your private tour.

MM Wrenfield, Isle of Wight - South

MM Meadowlark, Isle of Wight - South
$594,900
5 Beds ⋅ 3.1 Baths ⋅ 10654570 MLS
TO BE BUILT, Meadowlark MODEL AT WINDSOR SATION! Starting at $$594.900. Build your dream home and personalize it to fit your lifestyle. The Meadowlark offers 4 to 5 bedrooms, 2.5 to 3.5 baths, approximately 2881 to 3205 square feet, and a 2 car garage and the option to add a multi Gen Suite with spacious living and dining areas, kitchen with pantry, and laundry room. Optional second floor configurations provide additional living space, a loft, fourth bedroom, and full bath. Standard features include 9 foot ceilings, electric fireplace, LVP flooring in main living areas, shaker style soft close kitchen cabinetry, quartz countertops, under cabinet lighting, stainless steel appliances, primary bath tile shower, and a 2 car garage. Energy efficient construction and builder warranty included. Choose your homesite, select your finishes, and make the Meadowlark your own at Windsor Station. Pricing reflects base home and is subject to change. Options and upgrades may be additional. Please call today for your private tour.

MM Meadowlark, 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

11563 Savannah Street, Isle of Wight - South
$529,900
4 Beds ⋅ 3.1 Baths ⋅ 10648234 MLS
MOVE-IN READY + $10,000 FLEX CASH! This beautifully designed ranch-style home offers 4 bedrooms and 3.5 baths with a spacious, well-planned layout ideal for comfortable everyday living. The primary suite and two additional bedrooms are located on the first floor, while a private fourth bedroom and full bath are upstairs. Interior features include shaker-style soft-close cabinetry, granite countertops, tile backsplash, double wall ovens, luxury vinyl plank flooring, a cozy fireplace with built-ins, and a tiled walk-in shower in the primary suite. Situated on a generous 18,449 SF cul-de-sac homesite, the covered rear porch and patio provide excellent space for outdoor living and entertaining. For a limited time, receive $10,000 Flex Cash with use of the preferred lender and settlement agent. Located in Windsor, enjoy small-town charm, local community events, and a relaxed pace of life with convenient access to Suffolk, Smithfield, and greater Hampton Roads.

11563 Savannah Street, Isle of Wight - South

12242 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 multi-generational living. This potentially 6-bedroom, 3.5-bath plan features a 1st floor primary suite, downstairs laundry, and an open family room that flows into a chef-inspired kitchen with generous island. The large pantry and bright breakfast area are perfect for everyday living and entertaining. An additional 1st floor guest room with ensuite includes a 5ft shower. Upstairs offers 3 spacious bedrooms, two full baths including a convenient Jack-and-Jill layout, 2nd laundry, a bonus/guest room and a media/guest room ideal for relaxing, working, or gathering. An added finished space provides optimal storage for seasonal items, crafting or heirlooms. Enjoy small-town charm in Windsor w/ easy access to Rte 460, shopping, dining, and minutes from downtown Suffolk. Currently under construction – ready by early spring 2027. Let’s make this home yours!

12242 Ava Lane, Isle of Wight - South

8368 Whispering Pines Trail, Isle of Wight - North
$375,000
3 Beds ⋅ 2 Baths ⋅ 10641278 MLS
Welcome to Whispering Pines Trail, a rare opportunity to own a beautifully updated home on 4.46 private acres in Windsor. This 3-bedroom, 2-bath home offers 2,208 square feet of move-in ready living space with a fully updated kitchen, renovated primary bath, new flooring, paint, and trim throughout. The spacious upstairs family room is wired for surround sound and projector, with the screen conveying. Outdoors, you'll find exceptional workshop and storage space including a 30'x86' main shop, a 26'x37' secondary shop and cinder block pump house with room for additional storage. Enjoy the peace and privacy of country living while having room for hobbies, equipment, recreation, or a home-based business. A truly unique property offering space, versatility, and endless possibilities in desirable Windsor. Owner Financing available.

8368 Whispering Pines Trail, Isle of Wight - North

MM Cypress (Windsor Station), Isle of Wight - South
$514,990
4 Beds ⋅ 3 Baths ⋅ 10637146 MLS
Discover The Cypress by Eastwood Homes at Windsor Station, where modern elegance meets timeless charm. This beautifully designed four-bedroom, three-bath home features a flexible first-floor guest suite and a well-appointed kitchen with a large island and walk-in pantry perfect for entertaining and everyday living. Upstairs, enjoy an expansive loft for a media room or play space, along with a private primary retreat, two additional bedrooms, and convenient second-floor laundry. Personalize your dream home with options like a sunroom, luxury primary suite, or third-floor bonus room. Located in charming Windsor, enjoy small-town living with quick access to Route 460, shopping, and dining--crafted for style, comfort, and today's lifestyle.

MM Cypress (Windsor Station), Isle of Wight - South

MM Mcdowell, Isle of Wight - South
$574,990
4 Beds ⋅ 3.1 Baths ⋅ 10636517 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 butler's 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.

MM Mcdowell, Isle of Wight - South

MM Caldwell, Isle of Wight - South
$499,990
3 Beds ⋅ 2 Baths ⋅ 10636508 MLS
Experience effortless living in The Caldwell by Eastwood Homes at Windsor Station, a beautifully designed ranch-style home offering comfort, flexibility, and modern convenience. This thoughtfully crafted floor plan features three spacious bedrooms, two full baths, and a first-floor primary suite with dual closets for added storage. Enjoy a bright, open layout with a formal dining room, expansive family room, and a chef-inspired kitchen complete with an island and pantry perfect for everyday living and entertaining. A dedicated pocket office provides the ideal work-from-home space. Personalize your home with flexible options, including additional office space, expanded storage, outdoor living features like a covered or screened porch, or an optional second floor with extra bedrooms and loft designed to fit your lifestyle.

MM Caldwell, Isle of Wight - South

MM Davidson, Isle of Wight - South
$544,990
5 Beds ⋅ 3 Baths ⋅ 10636499 MLS
Enter into The Davidson by Eastwood Homes at Windsor Station, a beautifully designed two-story home where space, comfort, and connection come together. With five bedrooms and three full baths, this inviting layout features elegant formal living and dining rooms, a bright, open kitchen with island, pantry, and breakfast area, and a spacious family room perfect for gathering and making memories. A first-floor guest suite with full bath offers a warm welcome for visitors or multi-generational living. Upstairs, retreat to a private primary suite alongside three additional bedrooms, a versatile loft, and a generous laundry room designed to simplify everyday life. Make it truly yours with customizable options like a private home office, designer kitchen with butler's pantry, luxury bath upgrades, outdoor living spaces, or an optional third floor creating the perfect place to live, relax, and grow.

MM Davidson, 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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