5

Windsor, CT Homes for Sale under $300,000

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  • 41 Chestnut Dr, Windsor, CT 06095
    41 Chestnut Dr, Windsor, CT 06095
    41 Chestnut Dr, Windsor, CT 06095
    /27

    $299,925

    • 2 Beds
    • 2 Baths
    • 1,452 Sq Ft

    41 Chestnut Dr, Windsor, CT 06095

    Welcome to 41 Chestnut Drive, a charming and well-maintained Cape Cod style home nestled in a quiet Windsor neighborhood, perfect for those seeking comfort, convenience, and classic New England character. This bright and inviting residence has 2 spacious bedrooms with an extra room for either a den or an office, 2 full baths with one being totally renovated, with a flexible floor plan that blends

    Agent Photo

    Jason Kemp

    Five Stars Realty

    (860) 737-9994

    41 Chestnut Dr, Windsor, CT 06095
  • 25 Matthew Ln, Windsor, CT 06095
    25 Matthew Ln, Windsor, CT 06095
    25 Matthew Ln, Windsor, CT 06095
    /5

    $289,000

    • Land
    • 18.36 Acres
    • $15,741 per Acre

    25 Matthew Ln, Windsor, CT 06095

    Attention Builders!!! 18.36 acre residential building lot available for a private estate or possible subdivision. Water line brought in 20 ft into the property. Electrical cable and contour map available. Great location at the end of a cul-de-sac. Schedule your lot viewing today!!

    Antoinette Gooley Coldwell Banker Realty

    25 Matthew Ln, Windsor, CT 06095
  • 308 Prospect Hill Rd, Windsor, CT 06095
    308 Prospect Hill Rd, Windsor, CT 06095
    308 Prospect Hill Rd, Windsor, CT 06095
    /21

    $250,000

    • 4 Beds
    • 1.5 Baths
    • 1,921 Sq Ft

    308 Prospect Hill Rd, Windsor, CT 06095

    Windsor's finest! This 1815 antique Colonial offers a true piece of history with endless potential. Situated on a flat corner lot in Windsor's highly desirable Poquonock neighborhood, this home features 4 bedrooms, 1.5 bathrooms, original 12-inch wide hardwood floors and five fireplaces. Newer Gas heating system and plenty of closet space. Enjoy proximity to local parks, Bradley International

    Eli Joseph eXp Realty

    308 Prospect Hill Rd, Windsor, CT 06095
  • 142 High Path Rd, Windsor, CT 06095
    142 High Path Rd, Windsor, CT 06095
    142 High Path Rd, Windsor, CT 06095
    /35

    $239,609

    • 2 Beds
    • 2.5 Baths
    • 1,316 Sq Ft

    142 High Path Rd, Windsor, CT 06095

    Beautifully renovated 2/3 bedroom, 2.5 bath townhouse in the desirable Chateau Woods community! This turnkey home features a fully updated kitchen with granite countertops, stainless steel appliances, and modern cabinetry. The open concept living and dining area offers durable laminate flooring and plenty of natural light. Both bedrooms include wall to wall carpeting and private, updated baths.

    Keith Murphy Innovative Properties

    142 High Path Rd, Windsor, CT 06095
  • 268 High Path Rd Unit 268, Windsor, CT 06095
    268 High Path Rd Unit 268, Windsor, CT 06095
    268 High Path Rd Unit 268, Windsor, CT 06095
    /17

    $259,900

    • 3 Beds
    • 2.5 Baths
    • 1,390 Sq Ft

    268 High Path Rd Unit 268, Windsor, CT 06095

    You don't want to miss this Unique Spacious and well-maintained 3-bedroom, 2.5-bath townhouse condo in the desirable Chateau Woods community. This home features an open-concept living and dining area, updated kitchen with ample cabinetry, and a private patio perfect for relaxing or entertaining. Upstairs includes three generous bedrooms, including a primary suite with master bath. Additional

    Cynthia Rabb eXp Realty

    268 High Path Rd Unit 268, Windsor, CT 06095
Connecticut Hartford County Windsor

Real Estate & Homes in Windsor, CT under $300,000

Home Trends in Windsor, CT

On average, homes in Windsor, CT sell after 37 days on the market compared to the national average of 53 days. The median sale price for homes in Windsor, CT over the last 12 months is $360,000, up 1% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$360,000
Median Single Family Sale Price
$370,000
Median Townhouse Sale Price
$348,725
Median 2 Bedroom Sale Price
$312,450
Median 1 Bedroom Sale Price
$115,000
Average Price Per Sq Ft
$230
Number of Homes for Sale
28
Last 12 months Home Sales
332
Months of Supply
1.00
Median List Price
$350,000
Median Change From 1st List Price
-3%
Median Home Sale Price YoY Change
1%
How to Buy a Home How to Finance a Home How to Sell a Home

Browse a range of homes for sale under $300,000 in Windsor, offering accessible options for prospective buyers. With 5 listings available, there's a variety of affordable properties to explore, from charming starter homes to spacious family residences. These homes present an excellent opportunity to enter the housing market and secure a property that fits both your preferences and your budget in Windsor, CT.

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