Windsor, VA Homes for Sale

/48
$475,000
- 3 Beds
- 2 Baths
- 2,208 Sq Ft
8368 Whispering Pines Trail, Windsor, VA 23487

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

Leslie Brennan

Aweigh Real Estate

8368 Whispering Pines Trail, Windsor, VA 23487
Explore Windsor
/30
$588,900

New Construction
- 4 Beds
- 2.5 Baths
- 2,342 Sq Ft
47AC Holland Dr, Windsor, VA 23487

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

Dan Lawson

Green Tree Real Estate Inc

47AC Holland Dr, Windsor, VA 23487
/48
$514,990

New Construction
- 4 - 5 Beds
- 3 - 4 Baths
- 2,430 Sq Ft
Cypress Plan at Windsor Station, Windsor, VA 23487

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

Eastwood Homes Builder

0 Shiloh Dr Unit 36476046, Windsor, VA 23487
/41
$544,990

New Construction
- 5 - 6 Beds
- 3 - 4 Baths
- 3,047 Sq Ft
Davidson Plan at Windsor Station, Windsor, VA 23487

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

Eastwood Homes Builder

0 Shiloh Dr Unit 36500583, Windsor, VA 23487
/38
$574,990

New Construction
- 4 - 6 Beds
- 3.5 - 4.5 Baths
- 3,294 Sq Ft
McDowell Plan at Windsor Station, Windsor, VA 23487

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

Eastwood Homes Builder

0 Shiloh Dr Unit 36500947, Windsor, VA 23487
/2
$91,900

New Construction
- 2 Beds
- 2 Baths
- 930 Sq Ft
20 Clydes Ln Unit 20, Windsor, VA 23487

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

Tammy Newsom Clydes Dale

20 Clydes Ln Unit 20, Windsor, VA 23487
/3
$539,000

New Construction
- 4 Beds
- 3 Baths
- 2,232 Sq Ft
12343 Ava Ln, Windsor, VA 23487

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

Christopher Kostyrka RE/MAX Connect

12343 Ava Ln, Windsor, VA 23487
/39
$509,990

New Construction
- 4 Beds
- 2.5 Baths
- 2,449 Sq Ft
MM Raleigh, Windsor, VA 23487

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

Lori Cutrell BHHS RW Towne Realty

MM Raleigh, Windsor, VA 23487
/2
$599,000

New Construction
- 5 Beds
- 3.5 Baths
- 2,990 Sq Ft
12162 Ava Ln, Windsor, VA 23487

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

Christopher Kostyrka RE/MAX Connect

12162 Ava Ln, Windsor, VA 23487
/50
$574,990

New Construction
- 4 Beds
- 3.5 Baths
- 3,294 Sq Ft
MM Mcdowell, Windsor, VA 23487

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

Lori Cutrell BHHS RW Towne Realty

MM Mcdowell, Windsor, VA 23487
/32
$509,990

New Construction
- 4 - 5 Beds
- 2.5 - 3.5 Baths
- 2,449 Sq Ft
Raleigh Plan at Windsor Station, Windsor, VA 23487

The Raleigh is a two-story, four-bedroom, two-and-a-half-bath home with a first-floor primary bedroom, formal dining room, two-story family room, and a kitchen with an island and pantry. The second floor features an upstairs loft area, three additional bedrooms, and a full bath.Options to personalize this home include an expanded loft area, an enclosed bonus room, a second primary bedroom

Eastwood Homes Builder

0 Shiloh Dr Unit 36498467, Windsor, VA 23487
/6
$81,900

New Construction
- 2 Beds
- 1 Bath
- 686 Sq Ft
225 Partridge Ln, Windsor, VA 23487

This charming 686 square feet manufactured home, built in 2026 by Fleetwood, offers a comfortable and modern living space in Windsor, VA. Featuring two bedrooms and one bathroom, the home includes a spacious living room perfect for relaxation and entertaining. The master bedroom boasts an en suite bathroom and a convenient walk-in closet, providing ample storage and privacy. The kitchen is fully

Tammy Newsom Clydes Dale

225 Partridge Ln, Windsor, VA 23487
/39
$544,990

New Construction
- 5 Beds
- 3 Baths
- 3,047 Sq Ft
MM Davidson, Windsor, VA 23487

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

Lori Cutrell BHHS RW Towne Realty

MM Davidson, Windsor, VA 23487
/46
$499,990

New Construction
- 3 Beds
- 2 Baths
- 2,071 Sq Ft
MM Caldwell, Windsor, VA 23487

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

Lori Cutrell BHHS RW Towne Realty

MM Caldwell, Windsor, VA 23487
/18
$583,800

New Construction
- 4 Beds
- 3.5 Baths
- 2,650 Sq Ft
12177 Ava Ln, Windsor, VA 23487

Welcome to Windsor Station! This stunning Oakville model will be move-in ready this August 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

Wyndy Woods RE/MAX Connect

12177 Ava Ln, Windsor, VA 23487
/50
$572,000

New Construction
- 11 Beds
- 3.5 Baths
- 2,311 Sq Ft
12236 Ava Ln, Windsor, VA 23487

Welcome to Windsor Station! This stunning Halena 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

Christopher Kostyrka RE/MAX Connect

12236 Ava Ln, Windsor, VA 23487
/10
$499,990

New Construction
- 3 - 5 Beds
- 2 - 4 Baths
- 2,071 Sq Ft
Caldwell Plan at Windsor Station, Windsor, VA 23487

The Caldwell is a ranch-style home with three bedrooms, two full baths, a first-floor primary bedroom with two closets, a convenient pocket office for a dedicated work or study-from-home space, a formal dining room, a spacious family room, and a kitchen with an island and pantry. Options available to personalize this home include an office instead of the formal dining room or bedroom two, a

Eastwood Homes Builder

0 Shiloh Dr Unit 36474900, Windsor, VA 23487
/7
$85,900

New Construction
- 3 Beds
- 2 Baths
- 1,128 Sq Ft
464 Bracey Cir, Windsor, VA 23487

This beautifully crafted 1128 square feet manufactured home, built in 2026 by Clayton, offers a spacious and modern living experience with 3 bedrooms and 2 bathrooms. The inviting living room flows seamlessly into the dining area, creating an open and comfortable space for family gatherings and entertaining. The kitchen is fully equipped with essential appliances including a fridge, oven,

Tammy Newsom Clydes Dale

464 Bracey Cir, Windsor, VA 23487
/21
$538,990

New Construction
- 4 Beds
- 3 Baths
- 2,438 Sq Ft
12169 Ava Ln, Windsor, VA 23487

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.

Eastwood Homes Builder

12169 Ava Ln, Windsor, VA 23487
/9
$82,900

New Construction
- 3 Beds
- 2 Baths
- 1,140 Sq Ft
68 Clydes Ln Unit 68, Windsor, VA 23487

This beautifully crafted 1140 square feet manufactured home, built in 2026 by Clayton, offers a modern and comfortable living space with 3 bedrooms and 2 full bathrooms. The home features a spacious living room and dining room perfect for family gatherings and entertaining guests. The well-appointed kitchen comes equipped with an oven, dishwasher, microwave, and fridge, making meal preparation a

Tammy Newsom Clydes Dale

68 Clydes Ln Unit 68, Windsor, VA 23487
/2
$639,990

New Construction
- 5 Beds
- 4.5 Baths
- 3,454 Sq Ft
12242 Ava Ln, Windsor, VA 23487

The McDowell is a beautifully designed two-story, five-bedroom, three-and-a-half-bath home featuring a first-floor primary suite, a first-floor guest suite with a full bath, a spacious family room, and a designer kitchen with an island and breakfast area. Additional features include a large concrete patio, a spacious bonus room, a separate media room, a walk-in closet, and an open rail staircase.

Eastwood Homes Builder

12242 Ava Ln, Windsor, VA 23487
/47
$549,900

$75K PRICE DROP
- 3 Beds
- 2.5 Baths
- 2,567 Sq Ft
25092 Tyler Dr, Windsor, VA 23487

Instant equity potential! Appraised 2026 $600K. 4.71 acres & no HOA in Windsor VA. 1994 brick home offering classic durability & modern efficiency. Features an eco-friendly geothermal HVAC system (unit replaced just last year) ensuring astonishingly low utility bills year-round. 3 bedrooms, 2.5 baths, study & a bright sunroom. Large, new deck. Mudroom for ideal transition zone from outdoors. 2

Tracy Pudder World Class Realty

25092 Tyler Dr, Windsor, VA 23487
/9
$69,900

$6K PRICE DROP
- 3 Beds
- 2 Baths
- 1,216 Sq Ft
308 Pheasant Ln, Windsor, VA 23487

This beautiful 1216 square feet manufactured home in Clydes Dale community features 3 spacious bedrooms and 2 bathrooms, perfect for a small family or a couple looking to settle down. This home boasts modern finishes and amenities, including an open concept living area, a fully equipped kitchen with stainless steel appliances, and plenty of natural light. The master bedroom includes an ensuite

Tammy Newsom Clydes Dale

308 Pheasant Ln, Windsor, VA 23487
/18
$549,000

New Construction
- 4 Beds
- 3.5 Baths
- 2,311 Sq Ft
11564 Savannah St, Windsor, VA 23487

Welcome to Windsor Station! This stunning Halena model, elevation B,will be move-in ready this August 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

Christopher Kostyrka RE/MAX Connect

11564 Savannah St, Windsor, VA 23487
/17
$265,000
- 2 Beds
- 1 Bath
- 1,232 Sq Ft
14 B Ave, Windsor, VA 23487

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

Kara Eason RE/MAX Country to Coast

14 B Ave, Windsor, VA 23487
/3
$200,000
- Land
- 17.69 Acres
- $11,306 per Acre
15+AC Courthouse Hwy, Windsor, VA 23487

Great opportunity to purchase almost 20 acres of land in the town of Windsor VA. There is an easement that gives 50' of road frontage the land is zoned Residential.

JR Doughty 1st Class Real Estate Norfolk

15+AC Courthouse Hwy, Windsor, VA 23487
/32
$519,990

New Construction
- 4 Beds
- 2.5 Baths
- 2,591 Sq Ft
MM Drexel, Windsor, VA 23487

The Drexel is a two-story, four-bedroom, two-and-a-half-bath home with a formal living room, formal dining room, kitchen with island and a pantry, and a spacious great room. The second floor features four bedrooms, including the primary suite with a large closet, an upstairs laundry, an additional full bath, and a loft area. Options to personalize this home include a home office, bay window in

Lori Cutrell BHHS RW Towne Realty

MM Drexel, Windsor, VA 23487
/49
$289,990

$10K PRICE DROP
- 4 Beds
- 2 Baths
- 2,086 Sq Ft
44 N Court St, Windsor, VA 23487

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

Ron Sawyer RE/MAX Prime

44 N Court St, Windsor, VA 23487
/65
$519,990

New Construction
- 4 - 5 Beds
- 2.5 - 3.5 Baths
- 2,591 Sq Ft
Drexel Plan at Windsor Station, Windsor, VA 23487

The Drexel is a two-story, four-bedroom, two-and-a-half-bath home with a formal living room, formal dining room, kitchen with island and a pantry, and a spacious great room. The second floor features four bedrooms, including the primary suite with a large closet, an upstairs laundry, an additional full bath, and a loft area. Options to personalize this home include a home office, bay window in

Eastwood Homes Builder

0 Shiloh Dr Unit 36487210, Windsor, VA 23487
/9
$175,000
- Land
- 31,101 Sq Ft
- $245,098 per Acre
.71 Ac E Windsor Blvd, Windsor, VA 23487

*FRONTAGE ON MAJOR HWY. ENTRANCE FROM ADJACENT PROPERTY IS AVAILABLE WHICH WOULD NOT REQUIRE TURN LANE.**SEE ATTACHED SURVEY.

Durwood Scott Scott & Assoc. Inc. Realtors

.71 Ac E Windsor Blvd, Windsor, VA 23487
/27
$514,990

New Construction
- 4 Beds
- 3 Baths
- 2,430 Sq Ft
MM Cypress (Windsor Station), Windsor, VA 23487

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

Lori Cutrell BHHS RW Towne Realty

MM Cypress (Windsor Station), Windsor, VA 23487
/4
$160,000
- Land
- 21.71 Acres
- $7,370 per Acre
21AC Murphy Mill Rd, Windsor, VA 23487

OFFER ACCEPTED. Welcome to the parcel of endless possibilities. This parcel offers 21 acres of flat land, with approximately 1/3 cleared and the other 2/3 wooded with mature trees. Build your homestead on the cleared portion and use the rest for recreational use, or clear the rest to allow room for your horses. It is conveniently located less than 15 minutes from the town of Windsor or the city

Nicole Hardy Fathom Realty

21AC Murphy Mill Rd, Windsor, VA 23487
/34
$435,000

$15K PRICE DROP
- 5 Beds
- 2 Baths
- 2,500 Sq Ft
25452 Walters Hwy, Windsor, VA 23487

Looking for space and privacy? Look no further! This 5-bed, 2-bath, 2,500-square-foot rancher with both a 2-car attached garage and a large, oversized detached barn is the perfect combination. Sitting on exactly an acre, this home offers peace and quiet while being conveniently located near town.

Jordan Cowles EXP Realty LLC

25452 Walters Hwy, Windsor, VA 23487
/10
$115,900

New Construction
- 3 Beds
- 2 Baths
- 1,280 Sq Ft
419 Bracey Cir, Windsor, VA 23487

This beautifully crafted 1280 square feet manufactured home, built in 2026 by Fleetwood, offers a spacious and modern living experience in Windsor, VA. Featuring three bedrooms and two full bathrooms, this residence includes a welcoming living room and a dedicated dining area perfect for family gatherings. The master bedroom boasts an en suite bathroom and a generous walk-in closet, providing

Tammy Newsom Clydes Dale

419 Bracey Cir, Windsor, VA 23487

Virginia Isle Of Wight County

Why Live in Windsor

Windsor, Virginia, located at the junction of Route 460 and Route 258, is a small rural town 12 miles west of Suffolk. Known for its peaceful atmosphere and friendly community, Windsor offers a traditional small-town American lifestyle. Homebuyers can choose from a variety of single-family homes, including 1920s farmhouses, 1960s ranch styles, and modern homes from the 2000s, many of which sit on large lots. Windsor Elementary is highly rated, making the town appealing for families. Dining options include local favorites like Anna’s Ristorante, known for its award-winning pizza, and the popular El Rodeo Mexican restaurant. For shopping, residents can visit The Sassy Sisters for antiques and home décor. Outdoor activities are centered around Robinson Park, which features a playground and picnic shelter, and the nearby Windsor Public Library. Community events such as free concerts at Garis Park, the annual Christmas parade, and the Isle of Wight County Fair at Heritage Park foster a strong sense of local spirit. While Windsor lacks public transit, its location provides convenient access to the Hampton Roads region, making it a practical choice for commuters.

Learn more about living in Windsor

Frequently Asked Questions

What is the average home price in Windsor, VA?

Homes for sale in Windsor, VA have an average home price of $443,992.

How many homes have sold over the last 12 months in Windsor, VA?

58 homes have sold in Windsor, VA over the last 12 months.

What is the average household income in Windsor, VA?

The average household income in Windsor, VA is $89K.

Is Windsor, VA a safe city?

In general, the safest neighborhood in Windsor, VA with lower crime scores is Southern Isle of Wight.

What are the most popular zip codes in Windsor, VA?

The most popular zip codes in Windsor, VA include 23487, 23898, 23434, 23437 and 23866.

What are the most popular neighborhoods in Windsor, VA?

The most popular neighborhood in Windsor, VA with the most homes for sale is Southern Isle of Wight.

How much do you need to make to afford a house in Windsor?

The median home price in Windsor is $435,000. If you put a 20% down payment of $87,000 and had a 30-year fixed mortgage with an interest rate of 6.69%, your estimated principal and interest payment would be $2,240 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $96K a year to afford the median home price in Windsor. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Windsor is $89K.

How are the schools in Windsor, VA?

Windsor, VA has highly rated public and private schools. Some of the best schools in Windsor based on Niche Grades are Carrsville Elementary School, Windsor Elementary School and Georgie D. Tyler Middle School. The neighborhood in Windsor with the highest rated schools is Southern Isle of Wight. Browse all the schools in Windsor, VA to learn more.

Home Prices in Windsor, VA

The median home sale price in Windsor, VA is $384,999, up 69% year-over-year. Homes in Windsor sell in 35 days on average, compared to the national average of 56 days.

Home Price Trends

Median Sale Price $384,999	Median Single Family Sale Price $440,000
Median 2 Bedroom Sale Price $270,000	Average Price Per Sq Ft $210
Number of Homes for Sale 23	Last 12 months Home Sales 58
Months of Supply 4.80	Median List Price $435,000
Median Change From 1st List Price 0%	Median Home Sale Price YoY Change 69%

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Windsor Types of Homes for Sale

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