$382,942Average Value$215Average Price per Sq Ft31Homes For Sale
Western Tidewater's hidden, peaceful jewel
At the junction of Route 460 and Route 258, just 12 miles west of Suffolk, lies Windsor, Virginia. This small rural town, known to some as the “hidden jewel of Western Tidewater,” serves as a peaceful, amiable and conveniently located gateway to the more densely populated areas of the Hampton Roads region. “Windsor has a small community feel with a lot of friendly local folks,” says Lee Cross, a native of nearby Suffolk, Virginia, and the managing broker and third-generation co-owner of Cross Realty. “It’s your traditional small-town America.”
Choice of neighborhoods or land
Homebuyers seeking Windsor’s quiet, small-town lifestyle will find an eclectic mix of single-family home options, from 1920s farmhouses and 1960s ranch styles to modern traditional homes built in the 2000s. Many houses sit on ample lots of a half-acre or more, and interior sizes range from around 1,000 to 2,900 square feet. List prices tend to fall between $180,000 and $500,000. “Windsor has a nice combination of neighborhoods if you’re a neighborhood person — and land if you prefer to have some elbow room,” Cross says.
The streets of Windsor are lined with beautiful ranch-style homes.
Brick colonial-style homes epitomize the elegance of the neighborhood of Windsor.
Ranch-style homes offer spacious living with modern comfort in Windsor.
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Award-winning pizza
For a bite to eat, folks can hop over to U.S. Route 460, where they’ll find a selection of fast-casual chains and locally-owned restaurants, including Anna’s Ristorante, winner of The Tidewater News Hometown Choice Award for best pizza. “I’ve been known to go into Windsor for some Anna’s pizza,” Cross says. “The Mexican restaurant that opened about a year ago, El Rodeo, is pretty popular, too.” To grab ingredients for a home-cooked dinner, there’s a Food Lion grocery store right down the road. Those who fancy shopping for more than just groceries, The Sassy Sisters, a popular antiques and home décor shop, might be just the ticket.
Enjoy Mexican delights at El Rodeo Mexican Restaurant in Windsor.
Enjoy Windsor's delicious Italian cuisine at Anna's Ristorante Italiano and Pizzeria.
The Sassy Sisters antique shop in Windsor captivates with unique collectibles.
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Top-notch Isle of Wight County Schools
Windsor youngsters attend Isle of Wight County Public Schools, including Windsor Elementary, rated a B-plus and considered the No. 1 best elementary school in the county by Niche, and B-rated Tyler Middle. After Tyler, students move to Windsor High School, which also earns a B from Niche. “In my experience, people move to Windsor for the schools,” Cross says. “They’re a draw to the area.”
Windsor Elementary School cultivates curiosity and academic growth through innovative teaching.
Georgie D. Tyler Middle School cultivates vibrant learning among its students.
At Windsor High School, students excel in diverse endeavors.
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Swing and slide, then head to the library
For some outdoor time, Windsor folks can head to Robinson Park, where they can relax in the shade of the picnic shelter while the kids climb, slide and swing on the playground. Afterward, parkgoers can stop by the Windsor Public Library next door to grab a bestseller, enjoy storytime or join a book club.
Purchase agriculture, forestry and handcrafts at the Joel C. Bradshaw Fairgrounds in Windsor.
Concerts, Christmas parade and county fair
Windsor’s community spirit is apparent at the various town events throughout the year, including free concerts at the Garis Park gazebo and the annual Christmas parade, where participants can win a trophy for best band, best float and even best snow plow. At nearby Heritage Park, folks can enjoy Fourth of July fireworks and the annual Isle of Wight County Fair, where the non-stop fun includes carnival rides, live music, fair food — including funnel cakes — a demolition derby and the Miss Isle of Wight Pageant.
Conveniently located for Hampton Roads commutes
Having gained its name from the Norfolk Southern Railroad Windsor Station depot built in 1859, as well as its location at routes 460 and 258, the town of Windsor has long been associated with transportation and convenient access to all major parts of the Tidewater/Hampton Roads region. However, with the train depot long gone and no public transit in the town or nearby, locals must rely on their cars to travel around town and the region.
Written By
Kristen Hughes
Photography Contributed By
Shana Clarke
Video By
Emily McNamara
Interested in learning more about homes in this area?
Reach out to
James Nay,
an experienced agent in this area.
On average, homes in Windsor, VA sell after 36 days on the market compared to the national average of 55 days. The median sale price for homes in Windsor, VA over the last 12 months is $374,000, up 64% from the median home sale price over the previous 12 months.
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
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
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
Discover the Kestrel Ranch in the welcoming town of Windsor, where small-town charm, local events, and a relaxed pace of life blend with convenient access to Suffolk, Smithfield, and the greater Hampton Roads area. This beautifully crafted home features shaker-style cabinetry with soft-close doors and drawers, granite countertops, tile backsplash, double wall ovens, luxury vinyl plank flooring, a
Welcome to approximately 12 acres on Joyners Bridge Road in Windsor, Virginia, offering the perfect blend of a quiet rural setting while remaining conveniently located to everyday amenities. The Town of Windsor provides local shopping, services, schools, parks, and community conveniences, while nearby Suffolk offers additional shopping, dining, entertainment, and services. The property provides
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
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
The Cypress is a two-story, four-bedroom, three-bath home with a formal dining room, a first-floor guest suite with a full bath, and a kitchen with an island and pantry. The second floor features the primary bedroom, two additional bedrooms, a hall bath, a convenient upstairs laundry room, and an oversized loft area. Options available to personalize your home include a sunroom, screen porch, or
The Davidson is a two-story, five-bedroom, three-bath home with a formal living room, formal dining room, spacious family room, kitchen with island and pantry, separate breakfast area, and first-floor guest suite with a full bath. The second floor features four bedrooms, including the primary bedroom with an attached, private primary bath, an additional full bath, a large laundry room, and a loft
The McDowell is a two-story, four-bedroom, three-and-a-half-bath home with a first-floor primary bedroom, formal dining room, two-story family room, kitchen with an island and pantry, and a separate breakfast area. The second floor features three spacious bedrooms and two additional baths, including a Jack-and-Jill bath between bedrooms two and three, an oversized open loft area, and an
This beautifully crafted 930 square feet manufactured home, built in 2026 by Fleetwood, offers a comfortable and modern living space in Windsor, VA. Featuring 2 spacious bedrooms and 2 full bathrooms, this home includes a welcoming living room perfect for relaxation and entertaining. The master bedroom boasts an en suite bathroom for added privacy and convenience. The well-appointed kitchen comes
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,
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
Welcome to Windsor Station! Built by Taylor Construction, 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
Within 30 miles of bustling cities like Newport News and Norfolk lies Isle of Wight County, Virginia, a vast semi-rural area of Hampton Roads defined by its farmland and close-knit communities. “Isle of Wight County is a great combination of peaceful country living and town amenities,” says Lee Cross, a native of nearby Suffolk, Virginia, and the managing broker and third-generation co-owner of Cross Realty. “It has a lot of friendly local folks and a real small-town feel.”
Like all parts of the county, the southern portion of Isle of Wight has a wide variety of homes, from 1930s bungalows to 1960s ranch styles to modern farmhouse new-builds set on acres of land. “You’ll find a nice combination of traditional neighborhoods and land if you want a little more elbow room," Cross says. "You’ve got everything from homes on quiet streets tucked away off the beaten path to large farm property.” Home sizes range from around 1,000 to 4,400 square feet, and sale prices span from $180,000 to $750,000.
Area children attend Isle of Wight County Public Schools, including Windsor Elementary, rated a B-plus and considered the No. 1 best elementary school in the county by Niche, and B-rated Tyler Middle. After Tyler, students move to Windsor High School, which also earns a B from Niche. “In my experience, people move to Windsor for the schools,” Cross says. “They’re definitely a draw to the area.”
With the junction of two major county roads, Route 460 and Route 258, located in Windsor, other parts of the region, like Suffolk, Newport News or Norfolk, are all accessible and within a 30-mile drive of home. Public transit is limited to Smithfield in the north of the county.
Much of the dining and retail options in the southern part of the county are located near the town of Windsor. Along Route 460, there are numerous fast-casual chains and locally owned restaurants, including Checkers Family Restaurant, a popular spot for juicy burgers or homestyle dinners like chicken fried steak. “I live in nearby Suffolk, but I’ve been known to go into Windsor for a meal at Checkers,” Cross says. To grab ingredients for dinner at home, there’s a Food Lion grocery store right down the road, and for other weekly essentials, there’s also a convenient Family Dollar.
For some outdoor time, folks can head to Robinson Park in the town of Windsor, where find a shady picnic shelter and a small playground with slides and a swing set. History buffs enjoy spending time at Boykin's Tavern, a charming Colonial property near Route 258 - one of Virginia's oldest roadways - which once provided accommodation to weary travelers and served as a social hub for government officials from the county courthouse next door.
Through the various events that take place in Isle of Wight County during the year it’s apparent that the county's community spirit is alive and well. For instance, Windsor’s annual Christmas parade and free concerts at the town’s Garris Park gazebo always draw a crowd, and at nearby Heritage Park, folks always enjoy the magical Fourth of July fireworks and thrilling carnival rides, festive live music and sweet, fluffy funnel cakes at the annual Isle of Wight County Fair.
Property Mix - Square Feet
Windsor Has More Owners
Rental Home Trends
Number of Homes for Rent
1
Median Rent
$1,200
Median Single Family Home Rent
$1,700
Median 4 Bedroom Single Family Home Rent
$1,500
Demographics
Total Population
2,791
Median Age
45
Population under 18
23.8%
On par with the national average
23.8%
Population over 65
22.3%
On par with the national average
19.1%
Finances
Median Household Income
$60,583
Significantly below the national average
$79,597
Average Household Income
$89,397
Education and Workforce
High School Graduates
90.8%
College Graduates
24.8%
Below the national average
34.1%
Advanced Degrees
8.8%
On par with the national average
13.3%
% Population in Labor Force
67.6%
Weather
Annual Precipitation
48''
Average Winter Low Temperature
29°F
Average Summer High Temperature
90°F
Annual Snowfall
8''
Area Factors
Somewhat bikeable
Bikeability®
30/ 100
Somewhat walkable
Walkability®
30/ 100
Source: Local Logic
Sources: Local Logic
Local Logic measures the walkability, access to public transit and bikeability of any address. CAP Index provides objective, accurate, and consistent data to help measure, compare, and mitigate crime risks.
Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. Our sources include: Accuweather, Public Records and Neustar. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.
