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
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%
26 Stinson Place Windsor, CT Step back in time without sacrificing modern comfort in this remarkable two-family home da...	6 beds \| 3 baths \| 2,940 sq.ft.	$449,000	Airbnb cash on cash: 0.32% Traditional cash on cash: 6.66% Airbnb Rental Income: $2074 Traditional Rental Income: $4205 Airbnb ROI: 0.32% Traditional ROI: 6.66%
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%
5 Hudson Lane #5 Windsor, CT Here is one level living at its best! Rarely available in this active 55+ community of Gri...	2 beds \| 2 baths \| 1,509 sq.ft.	$385,000	Airbnb cash on cash: -1.33% Traditional cash on cash: 3.17% Airbnb Rental Income: $1688 Traditional Rental Income: $2840 Airbnb ROI: -1.33% Traditional ROI: 3.17%
98 High Path Road #98 Windsor, CT 2nd-Floor, 1 BR unit. 1-1/2 baths. End unit. Shared basement has common laundry and storag...	1 beds \| 2 baths \| 736 sq.ft.	$159,900	Airbnb cash on cash: -2.52% Traditional cash on cash: 7.51% Airbnb Rental Income: $837 Traditional Rental Income: $2041 Airbnb ROI: -2.52% Traditional ROI: 7.51%
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%
625 Palisado Avenue #APT 310 Windsor, CT JUST AVAILABLE! Larger, beautiful 2 Bedroom/1.5 Bath Unit in Windsor's fantastic Delamere ...	2 beds \| 2 baths \| 912 sq.ft.	$69,900	Airbnb cash on cash: -11.15% Traditional cash on cash: 1.95% Airbnb Rental Income: $1688 Traditional Rental Income: $2126 Airbnb ROI: -11.15% Traditional ROI: 1.95%

Real Estate investment in Windsor, CT

There are 23 properties for sale in the city of Windsor . The median list price in Windsor is $329,900 and the average price per square foot is $198. In December 2025, the average monthly cash on cash return in Windsor is 6.00%. The average monthly rental income in Windsor is $2,840.

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

There are 23 investment properties available for sale in Windsor.

In 2025, 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

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%