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Homes Under $500K in Windsor, CT — Page 2

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Homes Under $500K in Windsor, CT

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6 of 30 Listings

Homes Under $500K in Windsor, CT

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6 of 30 Listings

Map

Homes Under $500K in Windsor, CT

6 of 30 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #REB.0790925

Call Thomas

31Active
$325,000
3 bd · 2 ba · 1,511 sqft
284 Deerfield Road, Windsor, CT
Jill Menard · Realty One Group Cutting Edge
Price Reduced23Active
$290,995
3 bd · 2 ba · 1,229 sqft
36 Woodybrook Road, Windsor, CT
Richard Dale · Realty ONE Group Connect
Price Reduced36Active
$390,000
3 bd · 2 ba · 1,818 sqft
27 Eagleton Drive, Windsor, CT
John Brewer · Exceptional Real Estate LLC

Price Reduced24Active
$379,999
2 bd · 3 ba · 1,622 sqft
33 Mechanic Street 203, Windsor, CT
Hawwa Djuned · Maria Acuna Real Estate
Price Reduced12Active
$350,000
5 bd · 3 ba · — sqft
Address withheld · Windsor, CT
Mark Mermelstein · eXp Realty
Price Reduced36Active
$449,000
3 bd · 3 ba · 1,952 sqft
58 Amanda Circle, Windsor, CT
Steven Koleno · Beycome of Connecticut

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Listing data & MLS disclosures

SmartMLS: IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. The listing broker’s offer of compensation is made only to participants of the MLS where the listing is filed.

Windsor housing market

September 2026 · This period is still settling

Selling at 103.2% of asking price

Buyers here are paying above asking. MLS · 26 sales · as of Sep 30, 2026

Homes that sold · County records, as of Sep 11, 2026

Median sale price: $423,750$346,250–$508,000 typical range
Price per sq. ft.: $261
Sales: 14
Paid in cash: 42.9%

Homes on the market · MLS, as of Sep 27, 2026–Sep 30, 2026

Median list price: $394,000
Homes for sale: 42
Median days on market: 10 days

Price trend · Assessor repeat sales, as of Sep 30, 2026

Year-over-year: 24.6%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 2, 2026

Median home size: 1,516 sq. ft.

Windsor, CT community profile

Area: 30.5 sq. mi.

Source: HJN community data

L. Custen Realty, Inc. d/b/a Realty.com/L. Custen Realty CT, LLC d/b/a Realty.com (Tom O’Leary-Broker)(CT properties only), 8323 Southwest Freeway, Suite 900, Houston, Texas 77074

The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Listing data is derived from various Multiple Listing Services; each source MLS and its required disclaimer are shown with the listings on the applicable page. Realty.com is an independently owned and operated brokerage.

Listing data & MLS disclosures

SmartMLS: IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. The listing broker’s offer of compensation is made only to participants of the MLS where the listing is filed.

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #REB.0790925

Call Thomas

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #REB.0790925

Call Thomas

Windsor housing market

September 2026 · This period is still settling

Selling at 103.2% of asking price

Buyers here are paying above asking. MLS · 26 sales · as of Sep 30, 2026

Homes that sold · County records, as of Sep 11, 2026

Median sale price: $423,750$346,250–$508,000 typical range
Price per sq. ft.: $261
Sales: 14
Paid in cash: 42.9%

Homes on the market · MLS, as of Sep 27, 2026–Sep 30, 2026

Median list price: $394,000
Homes for sale: 42
Median days on market: 10 days

Price trend · Assessor repeat sales, as of Sep 30, 2026

Year-over-year: 24.6%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 2, 2026

Median home size: 1,516 sq. ft.

Windsor, CT community profile

Area: 30.5 sq. mi.

Source: HJN community data