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.

Single Family Homes for Sale in Windsor, CT

Search for Single Family Residential for Sale in Windsor, Connecticut. Browse all of Mashvisor’s Single Family Residential listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 20 Single Family Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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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%
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%
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%
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%

Your search for investment property begins and ends here

Single Family Homes 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