9

Windsor, CT Homes for Sale under $400,000

Section Image
  • 0 Walnut Dr, Windsor, CT 06095
    0 Walnut Dr, Windsor, CT 06095
    0 Walnut Dr, Windsor, CT 06095
    /9

    $349,000

    • Land
    • 13.3 Acres
    • $26,241 per Acre

    0 Walnut Dr, Windsor, CT 06095

    This 13.3 acre property consists of high-quality farmland that has naturally regenerated into a forest of white pine and mixed hardwoods. The land was originally created as 16 individual lots as part of an adjacent subdivision that was never completed and has since been combined into one contiguous parcel. Most of the property is now zoned Agricultural, with a few acres at the north end remaining

    Keith Ross LANDVEST

    0 Walnut Dr, Windsor, CT 06095
  • 490 Old Day Hill Rd, Windsor, CT 06095
    490 Old Day Hill Rd, Windsor, CT 06095
    490 Old Day Hill Rd, Windsor, CT 06095
    /11

    $325,000

    • Land
    • 12.18 Acres
    • $26,683 per Acre

    490 Old Day Hill Rd, Windsor, CT 06095

    Attention Farmers!! This 12+ acre location is strictly for the farmers. With a tobacco barn and newly updated potato barn this piece of property is ready for you to start your farming business. Agents please reach out for the specific guidelines with this property or read the agent notes

    Heather Heeb Keller Williams Realty-Longmdw

    490 Old Day Hill Rd, Windsor, CT 06095
  • 44 Maple Ave, Windsor, CT 06095
    44 Maple Ave, Windsor, CT 06095
    44 Maple Ave, Windsor, CT 06095
    /37

    $380,000

    • 3 Beds
    • 2 Baths
    • 1,554 Sq Ft

    44 Maple Ave, Windsor, CT 06095

    This 2-unit home offers the comfort and feel of a single-family residence, while providing the added benefit of rental income to help offset your mortgage. Inside, you'll find beautiful wood floors, a spacious primary bedroom with an additional area, perfect for a home office, studio, walk-in closet, or flex space. Laundry is conveniently located in each unit. The huge eat-in kitchen features a

    Barbara Clerice Elite Legacy Realty LLC

    44 Maple Ave, Windsor, CT 06095
  • 105 Sunrise Cir, Windsor, CT 06095
    105 Sunrise Cir, Windsor, CT 06095
    105 Sunrise Cir, Windsor, CT 06095
    /29

    $300,000 Open Wed 5PM - 7PM

    • 2 Beds
    • 1.5 Baths
    • 1,064 Sq Ft

    105 Sunrise Cir, Windsor, CT 06095

    Beautifully updated and truly turn-key, this 2-bedroom, 1.5-bath townhouse in the highly desirable Strawberry Hills Association is ready for you to move right in! Meticulously maintained and thoughtfully upgraded within the last two years, this home features a stunning new kitchen complete with SS appliances, updated flooring throughout, new carpet upstairs, fresh paint throughout, and new

    Brittany O'Hara William Raveis Real Estate

    105 Sunrise Cir, Windsor, CT 06095
  • 27 Fyler Dr, Windsor, CT 06095
    27 Fyler Dr, Windsor, CT 06095
    27 Fyler Dr, Windsor, CT 06095
    /9

    $315,000

    • 3 Beds
    • 1 Bath
    • 1,295 Sq Ft

    27 Fyler Dr, Windsor, CT 06095

    Located on a quiet cul-de-sac in Windsor, this inviting home combines comfort, efficiency, and an exceptional setting. Within walking distance of Sage Park Middle School and Windsor High School, it offers an ideal blend of convenience and community. Hardwood floors, thermal double-pane windows, and enhanced attic insulation support energy-efficient living, while the generous floor plan provides

    Claudia Dixon Weichert Realtors MRG

    27 Fyler Dr, Windsor, CT 06095
  • 0 Walnut and Larch Dr, Windsor, CT 06095
    0 Walnut and Larch Dr, Windsor, CT 06095
    0 Walnut and Larch Dr, Windsor, CT 06095
    /9

    $349,000

    • Land
    • 13.3 Acres
    • $26,241 per Acre

    0 Walnut and Larch Dr, Windsor, CT 06095

    This 13.3 acre property consists of high-quality farmland that has naturally regenerated into a forest of white pine and mixed hardwoods. The land was originally created as 16 individual lots as part of an adjacent subdivision that was never completed and has since been combined into one contiguous parcel. Most of the property is now zoned Agricultural, with a few acres at the north end remaining

    Keith Ross Landvest, Inc

    0 Walnut and Larch Dr, Windsor, CT 06095
  • 19 Songonosk St, Windsor, CT 06095
    19 Songonosk St, Windsor, CT 06095
    19 Songonosk St, Windsor, CT 06095
    /32

    $315,000

    • 3 Beds
    • 1 Bath
    • 990 Sq Ft

    19 Songonosk St, Windsor, CT 06095

    Beautifully remodeled and move-in ready, this charming 3-bedroom, 1-bath ranch offers the perfect blend of modern updates and everyday comfort. Step inside to find stylish vinyl plank flooring flowing seamlessly throughout, complemented by abundant natural light and updated finishes. The stunning kitchen features crisp white shaker cabinetry, stainless steel appliances, and a center island with

    Carrie Korenkiewicz Berkshire Hathaway NE Prop.

    19 Songonosk St, Windsor, CT 06095
  • 66 Maple Ave, Windsor, CT 06095
    66 Maple Ave, Windsor, CT 06095
    66 Maple Ave, Windsor, CT 06095
    /38

    $385,000

    • 1 Bed
    • 1.5 Baths
    • 1,868 Sq Ft

    66 Maple Ave, Windsor, CT 06095

    Welcome to a truly unique residential opportunity offering the perfect blend of living and flexible workspace. This well-maintained home features a private upstairs apartment designed for everyday living, space you need to feel right at home. On the main level, you'll find four generously sized rooms currently configured as professional offices, along with a spacious waiting area. Whether you

    Diane Cordiliko Realty One Group Cutting Edge

    66 Maple Ave, Windsor, CT 06095
  • 28 Skitchewaug St, Windsor, CT 06095
    28 Skitchewaug St, Windsor, CT 06095
    /2

    $309,999 Open Sat 1PM - 3:30PM

    • 3 Beds
    • 1.5 Baths
    • 1,472 Sq Ft

    28 Skitchewaug St, Windsor, CT 06095

    Welcome Home To This Lovely 1,472 Square Feet, 3 Bedroom, 1.5 Bath, Colonial House! Conveniently Located in A Peaceful Area Next To Parks, Several Hiking/Walking Trails Near the Connecticut River, A Nature Center, An Animal Barn, Highways, Libraries, Shopping, And Restaurants. This Well-Maintained Home Also Features Hardwood Floors Throughout, A Full-Size Deck, A Decent Sized Level Back Yard

    Craig Ings Hill Top Real Estate, LLC

    28 Skitchewaug St, Windsor, CT 06095
Connecticut Hartford County Windsor

Real Estate & Homes in Windsor, CT under $400,000

Home Trends in Windsor, CT

On average, homes in Windsor, CT sell after 36 days on the market compared to the national average of 55 days. The median sale price for homes in Windsor, CT over the last 12 months is $367,500, up 2% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$367,500
Median Single Family Sale Price
$375,250
Median Townhouse Sale Price
$250,000
Median 2 Bedroom Sale Price
$222,000
Median 1 Bedroom Sale Price
$125,000
Average Price Per Sq Ft
$235
Number of Homes for Sale
14
Last 12 months Home Sales
321
Months of Supply
0.50
Median List Price
$359,250
Median Change From 1st List Price
-3%
Median Home Sale Price YoY Change
2%
How to Buy a Home How to Finance a Home How to Sell a Home

Explore the array of homes and houses for sale under $400,000 in Windsor, where you'll find 9 options tailored for those seeking affordable real estate opportunities. Whether you're interested in spacious family homes, modern townhouses, or cozy bungalows, Windsor offers a diverse range of choices to match your needs and financial considerations. Take advantage of these affordably-priced properties to make your move into the real estate market in Windsor, CT.

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group