Real Estate Investment Properties for Sale in Windsor, CT

Looking for investment property in Windsor, CT with high ROI ?

Explore a variety of short-term homes & houses in Windsor, CT. Invest wisely with VRBO & Windsor, CT Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Investment Property for Sale in Windsor, CT

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
16 Hilltop Rd Windsor, CT There is much potential at this price to put your own touches on this raised ranch house t...	3 beds \| 2 baths \| 1,715 sq.ft.	$410,000	Airbnb cash on cash: 0.1% Traditional cash on cash: 2.72% Airbnb Rental Income: $1296 Traditional Rental Income: $1896 Airbnb ROI: 0.1% Traditional ROI: 2.72%
20 Tobey Ave Windsor, CT Move right in to this spacious property. Centrally located with hardwood floors throughout...	3 beds \| 1 baths \| 1,578 sq.ft.	$399,900	Airbnb cash on cash: 0.16% Traditional cash on cash: 3.68% Airbnb Rental Income: $1296 Traditional Rental Income: $2209 Airbnb ROI: 0.16% Traditional ROI: 3.68%
60 Nod Rd Windsor, CT This spacious 3 bedroom/2 full bath colonial is located in a quiet neighborhood at the end...	3 beds \| 2 baths \| 2,128 sq.ft.	$345,900	Airbnb cash on cash: -0.14% Traditional cash on cash: 6.95% Airbnb Rental Income: $1296 Traditional Rental Income: $3194 Airbnb ROI: -0.14% Traditional ROI: 6.95%
47 Wilson Ave Windsor, CT This fantastic colonial on a dead end street, is located in a desirable section of windsor...	3 beds \| 2 baths \| 1,415 sq.ft.	$319,000	Airbnb cash on cash: -0.06% Traditional cash on cash: 5.94% Airbnb Rental Income: $1296 Traditional Rental Income: $2694 Airbnb ROI: -0.06% Traditional ROI: 5.94%
957 Palisado Ave Windsor, CT Welcome to this charming 1773 center chimney colonial in the highly desirable town of Wind...	4 beds \| 3 baths \| 2,738 sq.ft.	$421,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.46% Airbnb Rental Income: $null Traditional Rental Income: $4144 Airbnb ROI: N/A Traditional ROI: 7.46%
342 Capen St Windsor, CT 3 BDRM \| 2.5 BTH \| 2100 SQFT New construction to be built. Quality built and energy effici...	3 beds \| 2 baths \| 1,800 sq.ft.	$569,900	Airbnb cash on cash: -1.62% Traditional cash on cash: 3.72% Airbnb Rental Income: $1296 Traditional Rental Income: $3735 Airbnb ROI: -1.62% Traditional ROI: 3.72%
58 Amanda Cir Windsor, CT PRICED TO SELL: MAJOR DISCOUNT & FLEXIBLE PRICING! Seller is relocating out of state and w...	3 beds \| 2 baths \| 1,952 sq.ft.	$436,000	Airbnb cash on cash: -0.68% Traditional cash on cash: 5.7% Airbnb Rental Income: $1296 Traditional Rental Income: $3493 Airbnb ROI: -0.68% Traditional ROI: 5.7%
39 Loren Cir Windsor, CT Spacious 4-bedroom, 2-bathroom Contemporary home on a cul-de-sac. The open floor plan incl...	4 beds \| 2 baths \| 2,402 sq.ft.	$344,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.18% Airbnb Rental Income: $null Traditional Rental Income: $3666 Airbnb ROI: N/A Traditional ROI: 8.18%
140 Portman Street Windsor, CT H&B Due 10/02/2025 12pm This adorable ranch-style home offers the perfect blend of com...	3 beds \| 1 baths \| 950 sq.ft.	$244,999	Airbnb cash on cash: 0.8% Traditional cash on cash: 6.04% Airbnb Rental Income: $1296 Traditional Rental Income: $2104 Airbnb ROI: 0.8% Traditional ROI: 6.04%
211 Macktown Road Windsor, CT Spacious 4-bedroom, 2.5-bath Raised Ranch offering over 1,800 sq ft of living space, set o...	4 beds \| 3 baths \| 1,194 sq.ft.	$299,999	Airbnb cash on cash: N/A Traditional cash on cash: 9.61% Airbnb Rental Income: $null Traditional Rental Income: $3659 Airbnb ROI: N/A Traditional ROI: 9.61%
280 Deerfield Road Windsor, CT Welcome to 280 Deerfield Road, where comfort and convenience come together in this invitin...	3 beds \| 3 baths \| 1,534 sq.ft.	$225,000	Airbnb cash on cash: 0.8% Traditional cash on cash: 11.99% Airbnb Rental Income: $1296 Traditional Rental Income: $3275 Airbnb ROI: 0.8% Traditional ROI: 11.99%
10 Oxcart Drive Windsor, CT Immaculate raised ranch with a cleared and level rear lot featuring spacious sized rooms w...	3 beds \| 3 baths \| 1,874 sq.ft.	$375,000	Airbnb cash on cash: -0.4% Traditional cash on cash: 7.37% Airbnb Rental Income: $1296 Traditional Rental Income: $3628 Airbnb ROI: -0.4% Traditional ROI: 7.37%
98 High Path Rd #98 Windsor, CT 2nd-Floor, 1 BR unit. 1-1/2 baths. End unit. Shared basement has common laundry and storag...	1 beds \| 1 baths \| 736 sq.ft.	$149,900	Airbnb cash on cash: -1.62% Traditional cash on cash: 9.07% Airbnb Rental Income: $837 Traditional Rental Income: $2041 Airbnb ROI: -1.62% Traditional ROI: 9.07%
9 Milo Peck Lane Windsor, CT Welcome to this beautiful colonial set in a quiet, sought-after neighborhood. This well-ma...	4 beds \| 3 baths \| 2,184 sq.ft.	$489,999	Airbnb cash on cash: N/A Traditional cash on cash: 5.58% Airbnb Rental Income: $null Traditional Rental Income: $3900 Airbnb ROI: N/A Traditional ROI: 5.58%
216 Hayden Station Road Windsor, CT A wonderful opportunity awaits with this classic Colonial set on an expansive and private ...	4 beds \| 2 baths \| 2,304 sq.ft.	$389,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.04% Airbnb Rental Income: $null Traditional Rental Income: $3508 Airbnb ROI: N/A Traditional ROI: 6.04%
19 Rainbow Creek Windsor, CT Presenting 19 Rainbow Creek in Windsor, a modern Colonial that has been fully updated to r...	3 beds \| 3 baths \| 1,904 sq.ft.	$435,000	Airbnb cash on cash: -0.29% Traditional cash on cash: 6.16% Airbnb Rental Income: $1296 Traditional Rental Income: $3518 Airbnb ROI: -0.29% Traditional ROI: 6.16%
87 Hilltop Road Windsor, CT Don't miss this meticulously maintained Dutch Colonial set on a quiet dead-end road in the...	3 beds \| 2 baths \| 1,856 sq.ft.	$380,000	Airbnb cash on cash: -0.27% Traditional cash on cash: 6.24% Airbnb Rental Income: $1296 Traditional Rental Income: $3213 Airbnb ROI: -0.27% Traditional ROI: 6.24%
1035 N Worthy St Windsor, CT 1035 N Worthy St, Windsor, CT 06095 \| Single Family Residential	3 beds \| 1 baths \| 1,085 sq.ft.	$289,241	Airbnb cash on cash: -0.18% Traditional cash on cash: 2.97% Airbnb Rental Income: $1296 Traditional Rental Income: $1751 Airbnb ROI: -0.18% Traditional ROI: 2.97%
1275 Matianuck Ave Windsor, CT 1275 Matianuck Ave, Windsor, CT 06095 \| Single Family Residential	3 beds \| 1 baths \| 1,234 sq.ft.	$245,000	Airbnb cash on cash: 0.34% Traditional cash on cash: 4.54% Airbnb Rental Income: $1296 Traditional Rental Income: $1864 Airbnb ROI: 0.34% Traditional ROI: 4.54%
11 Fyler Dr Windsor, CT 11 Fyler Dr, Windsor, CT 06095 \| Single Family Residential	3 beds \| 1 baths \| 1,094 sq.ft.	$349,900	Airbnb cash on cash: -0.69% Traditional cash on cash: 1.92% Airbnb Rental Income: $1296 Traditional Rental Income: $1749 Airbnb ROI: -0.69% Traditional ROI: 1.92%
10 Cleary Ln Windsor, CT 10 Cleary Ln, Windsor, CT 06095 \| Single Family Residential	4 beds \| 2 baths \| 2,360 sq.ft.	$550,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.64% Airbnb Rental Income: $null Traditional Rental Income: $3056 Airbnb ROI: N/A Traditional ROI: 2.64%
27 Fyler Dr Windsor, CT 27 Fyler Dr, Windsor, CT 06095 \| Single Family Residential	3 beds \| 1 baths \| 1,295 sq.ft.	$315,000	Airbnb cash on cash: -0.42% Traditional cash on cash: 2.95% Airbnb Rental Income: $1296 Traditional Rental Income: $1889 Airbnb ROI: -0.42% Traditional ROI: 2.95%
1060 Poquonock Ave Windsor, CT 1060 Poquonock Ave, Windsor, CT 06095 \| Single Family Residential	4 beds \| N/A baths \| 1,873 sq.ft.	$399,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.65% Airbnb Rental Income: $null Traditional Rental Income: $2624 Airbnb ROI: N/A Traditional ROI: 3.65%
268 High Path Rd #268 Windsor, CT 268 High Path Rd #268, Windsor, CT 06095 \| Condo/Coop	3 beds \| 2 baths \| 1,390 sq.ft.	$239,900	Airbnb cash on cash: -3.15% Traditional cash on cash: 3.96% Airbnb Rental Income: $1296 Traditional Rental Income: $2502 Airbnb ROI: -3.15% Traditional ROI: 3.96%
318 Capen St Windsor, CT 318 Capen St, Windsor, CT 06095 \| Single Family Residential	3 beds \| 2 baths \| 1,880 sq.ft.	$579,900	Airbnb cash on cash: -1.65% Traditional cash on cash: 2.26% Airbnb Rental Income: $1296 Traditional Rental Income: $3009 Airbnb ROI: -1.65% Traditional ROI: 2.26%
25 Matthew Ln Windsor, CT 25 Matthew Ln, Windsor, CT 06095 \| Other	N/A beds \| N/A baths \| N/A	$289,000	Airbnb cash on cash: 2.01% Traditional cash on cash: -0.24% Airbnb Rental Income: $2010 Traditional Rental Income: $874 Airbnb ROI: 2.01% Traditional ROI: -0.24%
490 Old Day Hill Rd Windsor, CT 490 Old Day Hill Rd, Windsor, CT 06095 \| Other	N/A beds \| N/A baths \| N/A	$325,000	Airbnb cash on cash: 1.44% Traditional cash on cash: -0.53% Airbnb Rental Income: $2010 Traditional Rental Income: $884 Airbnb ROI: 1.44% Traditional ROI: -0.53%
999 Stone Rd Windsor, CT 999 Stone Rd, Windsor, CT 06095 \| Other	N/A beds \| N/A baths \| N/A	$1,900,000	Airbnb cash on cash: -2.34% Traditional cash on cash: -2.68% Airbnb Rental Income: $2010 Traditional Rental Income: $884 Airbnb ROI: -2.34% Traditional ROI: -2.68%
9 Brown Ave Windsor, CT 9 Brown Ave, Windsor, CT 06095 \| Single Family Residential	3 beds \| 2 baths \| 1,329 sq.ft.	$294,900	Airbnb cash on cash: -0.24% Traditional cash on cash: 5.1% Airbnb Rental Income: $1296 Traditional Rental Income: $2372 Airbnb ROI: -0.24% Traditional ROI: 5.1%
608 Kennedy Rd Windsor, CT Welcome to 608 Kennedy Rd a perfect blend of modern comfort and exceptional opportunity in...	4 beds \| 2 baths \| 1,399 sq.ft.	$399,923	Airbnb cash on cash: N/A Traditional cash on cash: 5.33% Airbnb Rental Income: $null Traditional Rental Income: $3058 Airbnb ROI: N/A Traditional ROI: 5.33%
123 E Wolcott Ave Windsor, CT 123 E Wolcott Ave, Windsor, CT 06095 \| Single Family Residential	3 beds \| 1 baths \| 1,040 sq.ft.	$324,900	Airbnb cash on cash: -0.5% Traditional cash on cash: 5.91% Airbnb Rental Income: $1296 Traditional Rental Income: $2850 Airbnb ROI: -0.5% Traditional ROI: 5.91%
19 Tiffany Dr Windsor, CT 19 Tiffany Dr, Windsor, CT 06095 \| Single Family Residential	4 beds \| 2 baths \| 2,040 sq.ft.	$449,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.88% Airbnb Rental Income: $null Traditional Rental Income: $3040 Airbnb ROI: N/A Traditional ROI: 3.88%

Real Estate investment in Windsor, CT

There are 33 properties for sale in the city of Windsor . The median list price in Windsor is $600,000 and the average price per square foot is $195. In February 2026, the average monthly cash on cash return in Windsor is 5.00%. The average monthly rental income in Windsor is $2,850.

Windsor, CT Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 33 investment properties available for sale in Windsor.

In 2026, the best neighborhood to buy investment property is Windsor.

The ROI for Short-Term is higher than the Long-Term in Windsor with average rental income of $1,296.

Your search for investment property begins and ends here

Investment Property for Sale in Windsor, CT

16 Hilltop Rd

Windsor, CT

3 beds | 2 baths | 1,715 sq.ft.

$410,000

Airbnb cash on cash: 0.1%

Traditional cash on cash: 2.72%

Airbnb Rental Income: $1296

Traditional Rental Income: $1896

Airbnb ROI: 0.1%

Traditional ROI: 2.72%

20 Tobey Ave

Windsor, CT

3 beds | 1 baths | 1,578 sq.ft.

$399,900

Airbnb cash on cash: 0.16%

Traditional cash on cash: 3.68%

Airbnb Rental Income: $1296

Traditional Rental Income: $2209

Airbnb ROI: 0.16%

Traditional ROI: 3.68%

60 Nod Rd

Windsor, CT

3 beds | 2 baths | 2,128 sq.ft.

$345,900

Airbnb cash on cash: -0.14%

Traditional cash on cash: 6.95%

Airbnb Rental Income: $1296

Traditional Rental Income: $3194

Airbnb ROI: -0.14%

Traditional ROI: 6.95%

47 Wilson Ave

Windsor, CT

3 beds | 2 baths | 1,415 sq.ft.

$319,000

Airbnb cash on cash: -0.06%

Traditional cash on cash: 5.94%

Airbnb Rental Income: $1296

Traditional Rental Income: $2694

Airbnb ROI: -0.06%

Traditional ROI: 5.94%

957 Palisado Ave

Windsor, CT

4 beds | 3 baths | 2,738 sq.ft.

$421,000

Airbnb cash on cash: N/A

Traditional cash on cash: 7.46%

Airbnb Rental Income: $null

Traditional Rental Income: $4144

Airbnb ROI: N/A

Traditional ROI: 7.46%

342 Capen St

Windsor, CT

3 beds | 2 baths | 1,800 sq.ft.

$569,900

Airbnb cash on cash: -1.62%

Traditional cash on cash: 3.72%

Airbnb Rental Income: $1296

Traditional Rental Income: $3735

Airbnb ROI: -1.62%

Traditional ROI: 3.72%

58 Amanda Cir

Windsor, CT

3 beds | 2 baths | 1,952 sq.ft.

$436,000

Airbnb cash on cash: -0.68%

Traditional cash on cash: 5.7%

Airbnb Rental Income: $1296

Traditional Rental Income: $3493

Airbnb ROI: -0.68%

Traditional ROI: 5.7%

39 Loren Cir

Windsor, CT

4 beds | 2 baths | 2,402 sq.ft.

$344,000

Airbnb cash on cash: N/A

Traditional cash on cash: 8.18%

Airbnb Rental Income: $null

Traditional Rental Income: $3666

Airbnb ROI: N/A