Windsor Homes for Sale

/17
$38,500
- 2 Beds
- 1 Bath
- 434 Sq Ft
138 Ascutney St, Windsor, VT 05089

Cash Sale - Being Sold in "As Is - As Seen" Condition. This Trailer (+) addition(s) is on it's own land (Not in a Park). Is is located just a short walk form Kennedy Pond and Downtown Windsor VT. This home will NOT qualify for lender financing in its current condition. What started out as a trailer has had a couple of different additions over the years. Currently, you'll find a Kitchen/Dining

DJ Chabot Town and Country Realty

138 Ascutney St, Windsor, VT 05089
/38
$449,000
- 4 Beds
- 2.5 Baths
- 2,272 Sq Ft
96 Dairy Ln, Windsor, VT 05089

Before the leaves have fallen, the PRICE on this one has! Nestled on 1.34 picturesque acres in historic Windsor, this classic 4-bedroom Colonial blends timeless charm with comfortable living. Set back from the road, the home offers privacy and space to enjoy Vermont’s natural beauty while being just minutes from town amenities, schools, and I-91.Inside, you'll find a traditional floor

Katie Ladue Gilbert KW Vermont Woodstock

96 Dairy Ln, Windsor, VT 05089
/36
$235,000
- 3 Beds
- 1.5 Baths
- 1,900 Sq Ft
31 Maple St, Windsor, VT 05089

PRICE REDUCTION! Discover classic Vermont charm in this 3-bedroom, 1.5-bathroom home located on a quiet, tree-lined street just steps from downtown Windsor. This home is perfect for those who appreciate historic charm and are ready to make it their own. Inside, you’ll find a welcoming layout and abundant natural light. The first floor features a full bathroom, laundry, spacious living and dining

Tara Reeves Vermont Real Estate Company

31 Maple St, Windsor, VT 05089
/55
$598,000
- 3 Beds
- 3.5 Baths
- 2,391 Sq Ft
3440 Route 44, West Windsor, VT 05037

This well cared for contemporary home has only been used as a second home for the original owners. The house takes advantage of the southwest exposure to be able to bring the outside in with the use of large palladium windows and multiple French doors. Some of the interior features include 3 woodburning fireplaces ,wide pine floors ,vaulted ceilings ,and skylights. The floor plan has an easy

Carol Wood Williamson Group Sothebys Intl. Realty

3440 Route 44, West Windsor, VT 05037
/39
$575,000
- 3 Beds
- 2.5 Baths
- 1,452 Sq Ft
3361 County Rd, Windsor, VT 05089

Enjoy privacy and lovely views from this well executed contemporary home overlooking copious gardens and mature plantings to a spectacular pond with an arched footbridge (spotlights highlight the bridge after dark) to access your own little island. Beautiful updates throughout the home include new maintenance-free manufactured cedar-tone shingles on the entire house and workshop shed. The kitchen

Danny Kogut Williamson Group Sothebys Intl. Realty

3361 County Rd, Windsor, VT 05089
/36
$325,000
- 4 Beds
- 2 Baths
- 2,452 Sq Ft
358 Us Route 5 S, Windsor, VT 05089

Charming Duplex in the Heart of Windsor – Ideal for Owner-Occupants or Investors! Discover a fantastic opportunity to own a versatile, income-producing duplex in the vibrant and historic town of Windsor. Perfectly suited for an owner-occupant looking to offset their mortgage with rental income—or a savvy investor seeking solid returns—this well-maintained property offers both comfort and cash

Daniel Preston KW Vermont Woodstock

358 Us Route 5 S, Windsor, VT 05089
/36
$325,000
- 2,452 Sq Ft
358 Us Route 5 S, Windsor, VT 05089

Charming Duplex in the Heart of Windsor – Ideal for Owner-Occupants or Investors! Discover a fantastic opportunity to own a versatile, income-producing duplex in the vibrant and historic town of Windsor. Perfectly suited for an owner-occupant looking to offset their mortgage with rental income—or a savvy investor seeking solid returns—this well-maintained property offers both comfort and cash

Daniel Preston KW Vermont Woodstock

358 Us Route 5 S, Windsor, VT 05089
/27
$57,000
- Land
- 0.67 Acre
- $85,075 per Acre
00 Snow Ln, Windsor, VT 05089

Lovely residential neighborhood with easy access to I-91. This easy access building lot (Parcel #3) sits on a short private roadway with convenient hookups to town water and sewer. Power and internet is also at the street and easily available. Property is located on the school bus route and is a great location for families. Land is relatively flat and should be easy building. Good expansion

John Bassette Bassette Real Estate Group

00 Snow Ln, Windsor, VT 05089
/29
$55,000
- Land
- 0.56 Acre
- $98,214 per Acre
00 Snow Ln, Windsor, VT 05089

Lovely residential neighborhood with easy access to I-91. This perfect building lot (Parcel #2) sits on a short private roadway with convenient access to town water and sewer. Power and internet is at the street and easily available. Property is located on the school bus route and is a great location for families. The land is relatively flat and should be an easy building location. Good expansion

John Bassette Bassette Real Estate Group

00 Snow Ln, Windsor, VT 05089
/41
$98,000
- Land
- 1.23 Acres
- $79,675 per Acre
00 Snow Ln, Windsor, VT 05089

Lovely residential neighborhood with easy access to I91. These two separate and contiguous building lots sit on a small private road and have town water and sewer access on the edge of the property. Power is also on-site. This listing is for 1.23 acres that are divided into two separate buildable lots of Parcel #2 which is .56 acres (MLS #5036196), and Parcel #3 which is .67 acres (MLS #5036198).

John Bassette Bassette Real Estate Group

00 Snow Ln, Windsor, VT 05089
/4
$195,000
- 5 Beds
- 3.5 Baths
- 4,011 Sq Ft
70-74 State St, Windsor, VT 05089

The Stephen Jacob House is an extremely important historic residence in a town known for its historic architecture. Built in 1784 in the Georgian/Federal style, the residence was sited on the rise of State Street from the Village of Windsor. It's commanding presence was embellished with cornice dentil detailing and possibly a Palladian window. Having been used for many purposes over the

Wade Treadway Wade I Treadway Real Estate

70-74 State St, Windsor, VT 05089
/16
$96,232 New Construction
- 2 Beds
- 2 Baths
- 777 Sq Ft
11 Cubb Ct, Windsor, VT 05089

Welcome to 11 Cubb Court, Windsor, VT, where modern comfort meets affordability in Mount Ascutney MHP! This brand-new Redman 25206-58 manufactured home offers 2 bedrooms, 2 bathrooms, and 777 sq. ft. (13'4"x58) of thoughtfully designed living space. Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features energy-efficient

Kate Barry EXP Realty

11 Cubb Ct, Windsor, VT 05089
/11
$87,826 New Construction
- 1 Bed
- 1 Bath
- 643 Sq Ft
23 Cubb Ct, Windsor, VT 05089

Welcome to 23 Cubb Court, Windsor, VT, where modern comfort meets affordability in Mount Ascutney MHP! This brand-new Redman 25206-58 manufactured home offers 1 bedroom, 1 bathroom, and 643 sq. ft. (13'4"x48) of thoughtfully designed living space. Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features energy-efficient

Kate Barry EXP Realty

23 Cubb Ct, Windsor, VT 05089
/16
$96,232 New Construction
- 2 Beds
- 2 Baths
- 777 Sq Ft
517 Back Mountain Rd, Windsor, VT 05089

Welcome to 517 Back Mountain Rd., Windsor, VT, where modern comfort meets affordability in Mount Ascutney MHP! This brand-new Redman 25206-58 model manufactured home offers 2 bedrooms, 2 bathrooms, and 777 sq. ft. (13'4"x58) of thoughtfully designed living space. Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features

Kate Barry EXP Realty

517 Back Mountain Rd, Windsor, VT 05089
/15
$98,995 New Construction
- 3 Beds
- 2 Baths
- 880 Sq Ft
84 Cubb Ct, Windsor, VT 05089

Welcome to 84 Cubb Court, , Windsor, VT, where modern comfort meets affordability in Mount Ascutney MHP! This brand-new Redman 25206-66 model manufactured home offers 3 bedrooms, 2 bathrooms, and 880 sq. ft. (13'4"x66) of thoughtfully designed living space. Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features

Kate Barry EXP Realty

84 Cubb Ct, Windsor, VT 05089

Vermont Windsor County Windsor Windsor

Frequently Asked Questions Why Live in Windsor

Is Windsor a good place to live?

Windsor is a good place to live. Windsor is considered very car-dependent and somewhat bikeable. Windsor is a neighborhood with a crime score of 2, making it safer than the average neighborhood in the U.S. Windsor has 7 parks for recreational activities. It has a median age of 45. The average household income is $68,403 which is below the national average. College graduates make up 27.1% of residents. A majority of residents in Windsor are home owners, with 39.7% of residents renting and 60.3% of residents owning their home. A local real estate agent serving Windsor can help you decide if this neighborhood is the right one for you. Learn more on our Windsor neighborhood guide.

Is Windsor, VT a safe neighborhood?

Windsor, VT is safer than the average neighborhood in the United States. It received a crime score of 2 out of 10.

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

The median home price in Windsor is $282,450. If you put a 20% down payment of $56,500 and had a 30-year fixed mortgage with an interest rate of 6.56%, your estimated principal and interest payment would be $1,440 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $62K a year to afford the median home price in Windsor. The average household income in Windsor is $68K.

What are the best public schools in Windsor?

The best public schools that serve Windsor are:

Windsor School has a C+ Niche grade, a student teacher ratio of 13:1 and an average review score of 3.4.

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

The most popular zip codes in Windsor, Windsor, VT include 05089, 05037, 03745, 03781 and 05048.

What are the most popular neighborhoods near Windsor, Windsor, VT?

The most popular neighborhoods near Windsor, Windsor, VT are West Claremont, North End, West Side, East Side and South End.

Learn more about living in Windsor

Home Trends in Windsor, VT

On average, homes in Windsor, VT sell after 57 days on the market compared to the national average of 52 days. The median sale price for homes in Windsor, VT over the last 12 months is $270,000, up 13% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$270,000

Median Single Family Sale Price

$262,000

Median Townhouse Sale Price

$821,500

Average Price Per Sq Ft

$187

Number of Homes for Sale

Last 12 months Home Sales

Months of Supply

1.80

Median List Price

$282,450

Median Change From 1st List Price

Median Home Sale Price YoY Change

13%

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Windsor Types of Homes for Sale

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Copyright 2025 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.