Windsor Real Estate

Welcome to Windsor, Virginia – a charming town nestled in the heart of Isle of Wight County. Known for its rich history and tight-knit community, Windsor offers a delightful blend of small-town charm and modern conveniences. With its picturesque landscapes and friendly atmosphere, it's no wonder that this hidden gem is attracting new residents and visitors alike.

Windsor boasts a variety of outdoor recreational opportunities. The nearby Blackwater River provides the perfect backdrop for kayaking and fishing, while the town’s parks offer serene spots for picnics and leisurely strolls. The lush greenery and scenic views make it an ideal location for nature enthusiasts and families seeking a peaceful retreat.

History buffs will appreciate Windsor’s historical significance, with landmarks that tell the story of its past. The town is home to several well-preserved buildings that date back to the 19th century, providing a glimpse into the area’s rich heritage. The annual events and festivals held in Windsor foster a sense of community and celebrate the town’s unique culture.

Windsor's convenient location makes it easy to access larger cities like Norfolk and Suffolk, allowing residents to enjoy the best of both worlds – the tranquility of small-town life and the vibrancy of urban amenities. With a strong sense of community, excellent schools, and a welcoming atmosphere, Windsor is not just a place to live; it’s a place to call home. Come explore Windsor, where southern hospitality meets a bright future!

Newest Listings in Windsor

$539,000

4 Beds ⋅ 3 Baths ⋅ 10647159 MLS

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. Take advantage of closing cost assistance when using the builder's preferred lender and settlement company. *Pics are images of the proposed finished project and some items are subject to change.

12343 Ava Lane, Windsor

$265,000

2 Beds ⋅ 1 Baths ⋅ 10645204 MLS

Welcome to Windsor! This move-in ready home has had all the work done—just bring your paintbrush. Features include a new roof from 2017, an HVAC system less than a year old and under warranty, brand new kitchen cabinets with butcher block counters, new appliances including a water heater, fresh carpet, and stunning tongue-and-groove oak floors. The bathroom is completely updated, and the spacious attic offers potential for additional bedrooms. Conveniently located on a dead-end street, close to shopping, dining, and hwy for an easy commute.

14 B Avenue, Windsor

$599,000

5 Beds ⋅ 3.1 Baths ⋅ 10644107 MLS

Welcome to Windsor Station! This stunning Rutherford model will be move-in ready this December/January 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 5 bedrooms, including a spacious primary suite on the 1st floor 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. 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 New Year!

12162 Ava Lane, Windsor

$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, Windsor

$635,072

5 Beds ⋅ 3 Baths ⋅ 10642494 MLS

Step 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.

12330 Ava Lane, Windsor

$289,990

4 Beds ⋅ 2 Baths ⋅ 10642458 MLS

This 4-bedroom, 2-bath ranch offers comfortable one-level living with a spacious and functional layout.Interior features a blend of laminate and wood flooring throughout the main living areas. Enjoy a largebackyard perfect for relaxing, entertaining, or outdoor activities. Conveniently located near dining,schools, shopping, and major roadways for easy commuting.Property is in good condition and being sold as-is. Lender Approved Short Sale

44 N Court Street, Windsor

$380,000

3 Beds ⋅ 2 Baths ⋅ 10641944 MLS

Hunter's paradise on 5.93 private acres! Zoned Rural Residential, this peaceful property offers the perfect blend of privacy, comfort, and country living. Surrounded by abundant wildlife, it's an ideal retreat for hunters, nature lovers, or anyone looking to escape the hustle and bustle. Enjoy your morning coffee on the full-length front porch while watching deer, birds, and other wildlife. The approximately 1-acre fenced yard is perfect for pets, gardening, or outdoor activities. A detached garage/workshop with upper-level storage provides plenty of room for projects, equipment, or recreational gear. Chickens and horses are welcome, making this property well-suited for a rural lifestyle. The nearly 1,500-square-foot ranch features an open-concept living and dining area with vaulted ceilings and a centrally located wood stove, creating a warm and inviting gathering space. Ceiling fans throughout add year-round comfort. The spacious kitchen includes granite countertops, a pantry, and ample cabinet and counter space. Down the hall are three bedrooms, including a first-floor primary suite with a private bath featuring a relaxing jetted tub. Additional features include a 27.5 kW automatic whole-house generator, providing dependable backup power for added peace of mind. If you've been searching for acreage, privacy, abundant wildlife, and the comforts of country living, this exceptional property is ready to welcome you home.

9269 Whispering Pines Trail, Windsor

$475,000

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.

8368 Whispering Pines Trail, 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

$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, Windsor

$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), Windsor

$509,990

4 Beds ⋅ 2.1 Baths ⋅ 10636588 MLS

Discover luxury living in The Raleigh by Eastwood Homes at Windsor Station, a stunning two-story home designed for comfort and style. This spacious plan features four bedrooms and a sought-after first-floor primary suite for added convenience. The main level is ideal for entertaining, with a formal dining room and dramatic two-story family room flowing into a chef-inspired kitchen. Upstairs, a versatile loft overlooks the living space and connects to three additional bedrooms, perfect for family or guests. Customize your dream home with options like a sunroom, screened porch, second primary suite, or private bonus room blending flexibility, elegance, and modern living.

MM Raleigh, Windsor

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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.