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 19 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
89 East Wolcott Avenue Windsor, CT *Highest and best by Monday, November 17 at 5p.m.* Nicely maintained 3 bedroom 2 full ...	3 beds \| 2 baths \| 1,200 sq.ft.	$299,900	Airbnb cash on cash: -0.29% Traditional cash on cash: 5% Airbnb Rental Income: $1296 Traditional Rental Income: $2384 Airbnb ROI: -0.29% Traditional ROI: 5%
957 Palisado Avenue 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: 7.15% Airbnb Rental Income: $null Traditional Rental Income: $4144 Airbnb ROI: N/A Traditional ROI: 7.15%
58 Amanda Circle Windsor, CT PRICED TO SELL: MAJOR DISCOUNT & FLEXIBLE PRICING! Seller is relocating out of state and w...	3 beds \| 3 baths \| 1,952 sq.ft.	$436,000	Airbnb cash on cash: -1.17% Traditional cash on cash: 5.21% Airbnb Rental Income: $1296 Traditional Rental Income: $3493 Airbnb ROI: -1.17% Traditional ROI: 5.21%
16 Landing Circle Windsor, CT Welcome to your dream home! This 3 bedroom, two and half bathroom gem boasts an open-conce...	3 beds \| 3 baths \| 2,237 sq.ft.	$529,900	Airbnb cash on cash: -1.51% Traditional cash on cash: 3.36% Airbnb Rental Income: $1296 Traditional Rental Income: $3304 Airbnb ROI: -1.51% Traditional ROI: 3.36%
39 Loren Circle 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.	$344,900	Airbnb cash on cash: N/A Traditional cash on cash: 7.91% Airbnb Rental Income: $null Traditional Rental Income: $3666 Airbnb ROI: N/A Traditional ROI: 7.91%
39 Old Kennedy Road Windsor, CT Opportunity knocks! This 3-bedroom, 1-bath home with a 1-car garage offers great potential...	3 beds \| 2 baths \| 1,168 sq.ft.	$235,900	Airbnb cash on cash: 0.47% Traditional cash on cash: 8.72% Airbnb Rental Income: $1296 Traditional Rental Income: $2731 Airbnb ROI: 0.47% Traditional ROI: 8.72%
552 Stone Road Windsor, CT Welcome to this charming 3-bedroom ranch located in Windsor, CT! Set in a peaceful semi-ru...	3 beds \| 1 baths \| 1,128 sq.ft.	$299,994	Airbnb cash on cash: -0.29% Traditional cash on cash: 4.65% Airbnb Rental Income: $1296 Traditional Rental Income: $2284 Airbnb ROI: -0.29% Traditional ROI: 4.65%
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: 0.34% Traditional cash on cash: 5.58% Airbnb Rental Income: $1296 Traditional Rental Income: $2104 Airbnb ROI: 0.34% Traditional ROI: 5.58%
99 Pepperbush Way Windsor, CT 3-bedroom, 2.5-bath raised ranch offering comfort and convenience in a desirable setting. ...	3 beds \| 3 baths \| 1,194 sq.ft.	$259,900	Airbnb cash on cash: 0.15% Traditional cash on cash: 7.4% Airbnb Rental Income: $1296 Traditional Rental Income: $2671 Airbnb ROI: 0.15% Traditional ROI: 7.4%
107 Sunnyfield Drive Windsor, CT Scenic setting for this 7 room, 3 bedroom, 2.5-bath raised ranch with lower-level rec room...	3 beds \| 3 baths \| 1,352 sq.ft.	$329,900	Airbnb cash on cash: -0.54% Traditional cash on cash: 5.57% Airbnb Rental Income: $1296 Traditional Rental Income: $2786 Airbnb ROI: -0.54% Traditional ROI: 5.57%
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 \| 1,800 sq.ft.	$314,999	Airbnb cash on cash: N/A Traditional cash on cash: 8.92% Airbnb Rental Income: $null Traditional Rental Income: $3659 Airbnb ROI: N/A Traditional ROI: 8.92%
14 Loren Circle Windsor, CT Tucked at the end of a quiet cul-de-sac, this beautifully maintained raised ranch offers a...	3 beds \| 3 baths \| 1,942 sq.ft.	$389,900	Airbnb cash on cash: -0.93% Traditional cash on cash: 6.34% Airbnb Rental Income: $1296 Traditional Rental Income: $3549 Airbnb ROI: -0.93% Traditional ROI: 6.34%
30 Lovell Avenue Windsor, CT Deadline for offers is Monday 11/3 by 6pm Make this charming, clean, and well-maintained h...	3 beds \| 1 baths \| 1,225 sq.ft.	$284,500	Airbnb cash on cash: -0.13% Traditional cash on cash: 4.98% Airbnb Rental Income: $1296 Traditional Rental Income: $2262 Airbnb ROI: -0.13% Traditional ROI: 4.98%
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: 0.64% Traditional cash on cash: 11.84% Airbnb Rental Income: $1296 Traditional Rental Income: $3275 Airbnb ROI: 0.64% Traditional ROI: 11.84%
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: -0.85% Traditional cash on cash: 6.93% Airbnb Rental Income: $1296 Traditional Rental Income: $3628 Airbnb ROI: -0.85% Traditional ROI: 6.93%
31 Parkwood Drive Windsor, CT Looking for space, privacy, and a connection to nature? Look no further than 31 Parkwood D...	5 beds \| 3 baths \| 2,719 sq.ft.	$499,900	Airbnb cash on cash: -0.03% Traditional cash on cash: 6.31% Airbnb Rental Income: $2074 Traditional Rental Income: $4503 Airbnb ROI: -0.03% Traditional ROI: 6.31%
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: 5.18% Airbnb Rental Income: $null Traditional Rental Income: $3900 Airbnb ROI: N/A Traditional ROI: 5.18%

Your search for investment property begins and ends here

Single Family Homes for Sale in Windsor, CT

89 East Wolcott Avenue

Windsor, CT

3 beds | 2 baths | 1,200 sq.ft.

$299,900

Airbnb cash on cash: -0.29%

Traditional cash on cash: 5%

Airbnb Rental Income: $1296

Traditional Rental Income: $2384

Airbnb ROI: -0.29%

Traditional ROI: 5%

957 Palisado Avenue

Windsor, CT

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

$421,000

Airbnb cash on cash: N/A

Traditional cash on cash: 7.15%

Airbnb Rental Income: $null

Traditional Rental Income: $4144

Airbnb ROI: N/A

Traditional ROI: 7.15%

58 Amanda Circle

Windsor, CT

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

$436,000

Airbnb cash on cash: -1.17%

Traditional cash on cash: 5.21%

Airbnb Rental Income: $1296

Traditional Rental Income: $3493

Airbnb ROI: -1.17%

Traditional ROI: 5.21%

16 Landing Circle

Windsor, CT

3 beds | 3 baths | 2,237 sq.ft.

$529,900

Airbnb cash on cash: -1.51%

Traditional cash on cash: 3.36%

Airbnb Rental Income: $1296

Traditional Rental Income: $3304

Airbnb ROI: -1.51%

Traditional ROI: 3.36%

39 Loren Circle

Windsor, CT

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

$344,900

Airbnb cash on cash: N/A

Traditional cash on cash: 7.91%

Airbnb Rental Income: $null

Traditional Rental Income: $3666

Airbnb ROI: N/A

Traditional ROI: 7.91%

39 Old Kennedy Road

Windsor, CT

3 beds | 2 baths | 1,168 sq.ft.

$235,900

Airbnb cash on cash: 0.47%

Traditional cash on cash: 8.72%

Airbnb Rental Income: $1296

Traditional Rental Income: $2731

Airbnb ROI: 0.47%

Traditional ROI: 8.72%

552 Stone Road

Windsor, CT

3 beds | 1 baths | 1,128 sq.ft.

$299,994

Airbnb cash on cash: -0.29%

Traditional cash on cash: 4.65%

Airbnb Rental Income: $1296

Traditional Rental Income: $2284

Airbnb ROI: -0.29%

Traditional ROI: 4.65%

140 Portman Street

Windsor, CT

3 beds | 1 baths | 950 sq.ft.

$244,999

Airbnb cash on cash: 0.34%

Traditional cash on cash: 5.58%

Airbnb Rental Income: $1296

Traditional Rental Income: $2104

Airbnb ROI: 0.34%