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
1221 Poquonock Avenue Windsor, CT Beautifully updated and deceptively spacious split-level home offering substantially more ...	3 beds \| 2 baths \| 1,968 sq.ft.	$379,900	Airbnb cash on cash: -0.5% Traditional cash on cash: 5.22% Airbnb Rental Income: $1199 Traditional Rental Income: $2850 Airbnb ROI: -0.5% Traditional ROI: 5.22%
63 Pond Road Windsor, CT Tucked away on a quiet, convenient street in Windsor, this updated 3bedroom, 1.5bath raise...	3 beds \| 2 baths \| 1,914 sq.ft.	$374,900	Airbnb cash on cash: -0.61% Traditional cash on cash: 3.75% Airbnb Rental Income: $1199 Traditional Rental Income: $2344 Airbnb ROI: -0.61% Traditional ROI: 3.75%
18 Last Leaf Cir #18 Windsor, CT Beautiful townhome with bonus finished lower level and 1 car attached garage. The main flo...	2 beds \| 2 baths \| 1,536 sq.ft.	$359,000	Airbnb cash on cash: -3.37% Traditional cash on cash: 3.73% Airbnb Rental Income: $530 Traditional Rental Income: $2646 Airbnb ROI: -3.37% Traditional ROI: 3.73%
708 Park Avenue Windsor, CT Welcome to 708 Park Ave! This beautifully updated 1,736 sq ft single-family home offers 3 ...	3 beds \| 2 baths \| 1,736 sq.ft.	$375,000	Airbnb cash on cash: -0.11% Traditional cash on cash: 3.81% Airbnb Rental Income: $1199 Traditional Rental Income: $2188 Airbnb ROI: -0.11% Traditional ROI: 3.81%
110 Belmont Avenue Windsor, CT Welcome to this beautiful four bedroom one bath home in nice quiet neighborhood convenient...	4 beds \| 1 baths \| 1,138 sq.ft.	$320,000	Airbnb cash on cash: -1.97% Traditional cash on cash: 5.58% Airbnb Rental Income: $477 Traditional Rental Income: $2482 Airbnb ROI: -1.97% Traditional ROI: 5.58%
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: -2.51% Traditional cash on cash: 7.46% Airbnb Rental Income: $477 Traditional Rental Income: $4144 Airbnb ROI: -2.51% Traditional ROI: 7.46%
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.	$449,000	Airbnb cash on cash: -0.88% Traditional cash on cash: 5.5% Airbnb Rental Income: $1199 Traditional Rental Income: $3493 Airbnb ROI: -0.88% Traditional ROI: 5.5%
39 Loren Circle Windsor, CT Welcome to this spacious 4-bedroom, 2-bathroom Contemporary home on a cul-de-sac. The open...	4 beds \| 2 baths \| 2,402 sq.ft.	$339,000	Airbnb cash on cash: -2.54% Traditional cash on cash: 8.31% Airbnb Rental Income: $477 Traditional Rental Income: $3666 Airbnb ROI: -2.54% Traditional ROI: 8.31%
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: -0.69% Traditional cash on cash: 2.95% Airbnb Rental Income: $1199 Traditional Rental Income: $1889 Airbnb ROI: -0.69% 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: -2.81% Traditional cash on cash: 3.65% Airbnb Rental Income: $477 Traditional Rental Income: $2624 Airbnb ROI: -2.81% Traditional ROI: 3.65%
318 Capen St Windsor, CT 318 Capen St, Windsor, CT 06095 \| Single Family Residential	3 beds \| 2 baths \| 2,160 sq.ft.	$599,900	Airbnb cash on cash: -1.84% Traditional cash on cash: 2.08% Airbnb Rental Income: $1199 Traditional Rental Income: $3009 Airbnb ROI: -1.84% Traditional ROI: 2.08%
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: -1.26% Traditional cash on cash: -0.24% Airbnb Rental Income: $943 Traditional Rental Income: $874 Airbnb ROI: -1.26% 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: -1.47% Traditional cash on cash: -0.53% Airbnb Rental Income: $943 Traditional Rental Income: $884 Airbnb ROI: -1.47% Traditional ROI: -0.53%
1333 Palisado Ave Windsor, CT 1333 Palisado Ave, Windsor, CT 06095 \| Other	N/A beds \| N/A baths \| N/A	$99,000	Airbnb cash on cash: 2.16% Traditional cash on cash: 6.05% Airbnb Rental Income: $943 Traditional Rental Income: $972 Airbnb ROI: 2.16% Traditional ROI: 6.05%
0 Walnut and Larch Dr Windsor, CT 0 Walnut and Larch Dr, Windsor, CT 06095 \| Other	N/A beds \| N/A baths \| N/A	$349,000	Airbnb cash on cash: -1.58% Traditional cash on cash: -0.53% Airbnb Rental Income: $943 Traditional Rental Income: $940 Airbnb ROI: -1.58% Traditional ROI: -0.53%
943 High Path Road unit: 943 Windsor, CT Renovated in 2022. Combo LR/DR. Kitchen appliances new in 2022. Primary bedroom with walk-...	2 beds \| 2 baths \| 972 sq.ft.	$199,999	Airbnb cash on cash: -4.02% Traditional cash on cash: 6.09% Airbnb Rental Income: $530 Traditional Rental Income: $2171 Airbnb ROI: -4.02% Traditional ROI: 6.09%
823a Stone Rd Windsor, CT 823a Stone Rd, Windsor, CT 06095 \| Single Family Residential	4 beds \| 2 baths \| 2,300 sq.ft.	$729,000	Airbnb cash on cash: -2.96% Traditional cash on cash: 1.45% Airbnb Rental Income: $477 Traditional Rental Income: $3203 Airbnb ROI: -2.96% Traditional ROI: 1.45%
66 Maple Avenue Windsor, CT Welcome to a truly unique residential opportunity offering the perfect blend of living and...	1 beds \| 2 baths \| 1,868 sq.ft.	$375,000	Airbnb cash on cash: -1.8% Traditional cash on cash: 4.71% Airbnb Rental Income: $558 Traditional Rental Income: $2567 Airbnb ROI: -1.8% Traditional ROI: 4.71%
28 Skitchewaug St Windsor, CT 28 Skitchewaug St, Windsor, CT 06095 \| Single Family Residential	3 beds \| 1 baths \| 1,472 sq.ft.	$299,999	Airbnb cash on cash: -0.57% Traditional cash on cash: 3.69% Airbnb Rental Income: $1199 Traditional Rental Income: $2014 Airbnb ROI: -0.57% Traditional ROI: 3.69%
19 Songonosk St Windsor, CT 19 Songonosk St, Windsor, CT 06095 \| Single Family Residential	3 beds \| 1 baths \| 990 sq.ft.	$315,000	Airbnb cash on cash: -0.69% Traditional cash on cash: 2.17% Airbnb Rental Income: $1199 Traditional Rental Income: $1660 Airbnb ROI: -0.69% Traditional ROI: 2.17%
30 Parkwood Dr Windsor, CT 30 Parkwood Dr, Windsor, CT 06095 \| Single Family Residential	5 beds \| 2 baths \| 2,984 sq.ft.	$535,000	Airbnb cash on cash: -0.09% Traditional cash on cash: 3.3% Airbnb Rental Income: $2156 Traditional Rental Income: $3305 Airbnb ROI: -0.09% Traditional ROI: 3.3%
33 Mechanic Street #210 Windsor, CT Welcome to this stunning 2-bedroom, 2-bath expansive ranch-style condo, where dramatic mil...	2 beds \| 2 baths \| 1,550 sq.ft.	$343,500	Airbnb cash on cash: -2.2% Traditional cash on cash: 5.58% Airbnb Rental Income: $530 Traditional Rental Income: $2763 Airbnb ROI: -2.2% Traditional ROI: 5.58%
212 Ethan Dr Windsor, CT 212 Ethan Dr, Windsor, CT 06095 \| Single Family Residential	4 beds \| 3 baths \| 3,857 sq.ft.	$899,900	Airbnb cash on cash: -2.99% Traditional cash on cash: 1.89% Airbnb Rental Income: $477 Traditional Rental Income: $4301 Airbnb ROI: -2.99% Traditional ROI: 1.89%
857 Stone Rd Windsor, CT 857 Stone Rd, Windsor, CT 06095 \| Single Family Residential	3 beds \| 2 baths \| 2,100 sq.ft.	$650,000	Airbnb cash on cash: -1.94% Traditional cash on cash: 2.06% Airbnb Rental Income: $1199 Traditional Rental Income: $3237 Airbnb ROI: -1.94% Traditional ROI: 2.06%
158 Colton Street St Windsor, CT 158 Colton Street St, Windsor, CT 06095 \| Single Family Residential	2 beds \| 1 baths \| 1,518 sq.ft.	$325,000	Airbnb cash on cash: -2.59% Traditional cash on cash: 2.02% Airbnb Rental Income: $530 Traditional Rental Income: $1662 Airbnb ROI: -2.59% Traditional ROI: 2.02%
122 Capen St Windsor, CT 122 Capen St, Windsor, CT 06095 \| Single Family Residential	3 beds \| 1 baths \| 1,525 sq.ft.	$334,900	Airbnb cash on cash: -0.83% Traditional cash on cash: 3.25% Airbnb Rental Income: $1199 Traditional Rental Income: $2097 Airbnb ROI: -0.83% Traditional ROI: 3.25%
24 Valley View Dr Windsor, CT 24 Valley View Dr, Windsor, CT 06095 \| Single Family Residential	4 beds \| 3 baths \| 2,280 sq.ft.	$475,000	Airbnb cash on cash: -2.86% Traditional cash on cash: 5.3% Airbnb Rental Income: $477 Traditional Rental Income: $3837 Airbnb ROI: -2.86% Traditional ROI: 5.3%
371 Dunfey Lane #371 Windsor, CT Welcome to 371 Dunfey Lane in Windsor, CT - a beautifully newly renovated condo that blend...	3 beds \| 3 baths \| 2,236 sq.ft.	$399,900	Airbnb cash on cash: -0.69% Traditional cash on cash: 6.85% Airbnb Rental Income: $1199 Traditional Rental Income: $3637 Airbnb ROI: -0.69% Traditional ROI: 6.85%
158 High Path Rd #158 Windsor, CT 158 High Path Rd #158, Windsor, CT 06095 \| Condo/Coop	2 beds \| 2 baths \| 1,020 sq.ft.	$229,900	Airbnb cash on cash: -5.01% Traditional cash on cash: 2.61% Airbnb Rental Income: $530 Traditional Rental Income: $1910 Airbnb ROI: -5.01% Traditional ROI: 2.61%
120 Basswood Rd Windsor, CT 120 Basswood Rd, Windsor, CT 06095 \| Single Family Residential	4 beds \| 2 baths \| 2,441 sq.ft.	$279,000	Airbnb cash on cash: -2.67% Traditional cash on cash: 8.55% Airbnb Rental Income: $477 Traditional Rental Income: $3160 Airbnb ROI: -2.67% Traditional ROI: 8.55%
1 Morello Cir Windsor, CT 1 Morello Cir, Windsor, CT 06095 \| Single Family Residential	4 beds \| 2 baths \| 2,425 sq.ft.	$499,100	Airbnb cash on cash: -2.87% Traditional cash on cash: 4.01% Airbnb Rental Income: $477 Traditional Rental Income: $3422 Airbnb ROI: -2.87% Traditional ROI: 4.01%
160 Windbrook Dr Windsor, CT 160 Windbrook Dr, Windsor, CT 06095 \| Single Family Residential	3 beds \| 3 baths \| 2,474 sq.ft.	$385,000	Airbnb cash on cash: -1.13% Traditional cash on cash: 6.17% Airbnb Rental Income: $1199 Traditional Rental Income: $3446 Airbnb ROI: -1.13% Traditional ROI: 6.17%
14 Hampden Pl Windsor, CT 14 Hampden Pl, Windsor, CT 06095 \| Single Family Residential	4 beds \| 2 baths \| 2,166 sq.ft.	$520,000	Airbnb cash on cash: -2.88% Traditional cash on cash: 3.22% Airbnb Rental Income: $477 Traditional Rental Income: $3176 Airbnb ROI: -2.88% Traditional ROI: 3.22%

Real Estate investment in Windsor, CT

There are 37 properties for sale in the city of Windsor . The median list price in Windsor is $604,975 and the average price per square foot is $195. In May 2026, the average monthly cash on cash return in Windsor is 4.00%. The average monthly rental income in Windsor is $2,630.

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

There are 37 investment properties available for sale in Windsor.

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

The ROI for Long-Term is higher than the Short-Term in Windsor with average rental income of $2,630.

Your search for investment property begins and ends here

Investment Property for Sale in Windsor, CT

1221 Poquonock Avenue

Windsor, CT

3 beds | 2 baths | 1,968 sq.ft.

$379,900

Airbnb cash on cash: -0.5%

Traditional cash on cash: 5.22%

Airbnb Rental Income: $1199

Traditional Rental Income: $2850

Airbnb ROI: -0.5%

Traditional ROI: 5.22%

63 Pond Road

Windsor, CT

3 beds | 2 baths | 1,914 sq.ft.

$374,900

Airbnb cash on cash: -0.61%

Traditional cash on cash: 3.75%

Airbnb Rental Income: $1199

Traditional Rental Income: $2344

Airbnb ROI: -0.61%

Traditional ROI: 3.75%

18 Last Leaf Cir #18

Windsor, CT

2 beds | 2 baths | 1,536 sq.ft.

$359,000

Airbnb cash on cash: -3.37%

Traditional cash on cash: 3.73%

Airbnb Rental Income: $530

Traditional Rental Income: $2646

Airbnb ROI: -3.37%

Traditional ROI: 3.73%

708 Park Avenue

Windsor, CT

3 beds | 2 baths | 1,736 sq.ft.

$375,000

Airbnb cash on cash: -0.11%

Traditional cash on cash: 3.81%

Airbnb Rental Income: $1199

Traditional Rental Income: $2188

Airbnb ROI: -0.11%

Traditional ROI: 3.81%

110 Belmont Avenue

Windsor, CT

4 beds | 1 baths | 1,138 sq.ft.

$320,000

Airbnb cash on cash: -1.97%

Traditional cash on cash: 5.58%

Airbnb Rental Income: $477

Traditional Rental Income: $2482

Airbnb ROI: -1.97%

Traditional ROI: 5.58%

957 Palisado Avenue

Windsor, CT

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

$421,000

Airbnb cash on cash: -2.51%

Traditional cash on cash: 7.46%

Airbnb Rental Income: $477

Traditional Rental Income: $4144

Airbnb ROI: -2.51%

Traditional ROI: 7.46%

58 Amanda Circle

Windsor, CT

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

$449,000

Airbnb cash on cash: -0.88%

Traditional cash on cash: 5.5%

Airbnb Rental Income: $1199

Traditional Rental Income: $3493

Airbnb ROI: -0.88%

Traditional ROI: 5.5%

39 Loren Circle

Windsor, CT

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

$339,000

Airbnb cash on cash: -2.54%

Traditional cash on cash: 8.31%

Airbnb Rental Income: $477

Traditional Rental Income: $3666

Airbnb ROI: -2.54%