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: 0.22% Traditional cash on cash: 6.86% Airbnb Rental Income: $1508 Traditional Rental Income: $3433 Airbnb ROI: 0.22% Traditional ROI: 6.86%
9 Washington Rd Windsor, CT Must see this one level, modern ranch style home located on a dead-end street in a desirab...	4 beds \| 3 baths \| 2,027 sq.ft.	$469,900	Airbnb cash on cash: -0.37% Traditional cash on cash: 5.59% Airbnb Rental Income: $1792 Traditional Rental Income: $3925 Airbnb ROI: -0.37% Traditional ROI: 5.59%
58 Amanda Cir Windsor, CT PRICED TO SELL: MAJOR DISCOUNT & FLEXIBLE PRICING! Seller is relocating out of state and w...	3 beds \| N/A baths \| 1,952 sq.ft.	$449,000	Airbnb cash on cash: -0.27% Traditional cash on cash: 5.5% Airbnb Rental Income: $1508 Traditional Rental Income: $3493 Airbnb ROI: -0.27% Traditional ROI: 5.5%
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: -2.37% Traditional cash on cash: 3.96% Airbnb Rental Income: $1508 Traditional Rental Income: $2502 Airbnb ROI: -2.37% Traditional ROI: 3.96%
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: -1.38% Traditional cash on cash: 2.08% Airbnb Rental Income: $1508 Traditional Rental Income: $3009 Airbnb ROI: -1.38% 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: 0.2% Traditional cash on cash: -0.24% Airbnb Rental Income: $1420 Traditional Rental Income: $874 Airbnb ROI: 0.2% 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: -0.17% Traditional cash on cash: -0.53% Airbnb Rental Income: $1420 Traditional Rental Income: $884 Airbnb ROI: -0.17% Traditional ROI: -0.53%
1333 Palisado Ave Windsor, CT 1333 Palisado Ave, Windsor, CT 06095 \| Other	N/A beds \| N/A baths \| N/A	$95,000	Airbnb cash on cash: 6.67% Traditional cash on cash: 6.43% Airbnb Rental Income: $1420 Traditional Rental Income: $972 Airbnb ROI: 6.67% Traditional ROI: 6.43%
0 Walnut and Larch Dr Windsor, CT 0 Walnut and Larch Dr, Windsor, CT 06095 \| Other	N/A beds \| N/A baths \| N/A	$295,000	Airbnb cash on cash: 0.13% Traditional cash on cash: -0.06% Airbnb Rental Income: $1420 Traditional Rental Income: $940 Airbnb ROI: 0.13% Traditional ROI: -0.06%
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: -1.34% Traditional cash on cash: 1.45% Airbnb Rental Income: $1792 Traditional Rental Income: $3203 Airbnb ROI: -1.34% Traditional ROI: 1.45%
28 Skitchewaug St Windsor, CT 28 Skitchewaug St, Windsor, CT 06095 \| Single Family Residential	3 beds \| 1 baths \| 1,472 sq.ft.	$290,000	Airbnb cash on cash: 0.46% Traditional cash on cash: 3.92% Airbnb Rental Income: $1508 Traditional Rental Income: $2014 Airbnb ROI: 0.46% Traditional ROI: 3.92%
30 Parkwood Dr Windsor, CT 30 Parkwood Dr, Windsor, CT 06095 \| Single Family Residential	5 beds \| 2 baths \| 2,984 sq.ft.	$499,900	Airbnb cash on cash: -0.2% Traditional cash on cash: 3.75% Airbnb Rental Income: $1976 Traditional Rental Income: $3305 Airbnb ROI: -0.2% Traditional ROI: 3.75%
135 East St Windsor, CT What an amazing home that is move in ready, enjoy new kitchen and bathrooms, windows, new ...	3 beds \| 1 baths \| 1,525 sq.ft.	$389,900	Airbnb cash on cash: 0.25% Traditional cash on cash: 3.1% Airbnb Rental Income: $1508 Traditional Rental Income: $2113 Airbnb ROI: 0.25% Traditional ROI: 3.1%
857 Stone Rd Windsor, CT 857 Stone Rd, Windsor, CT 06095 \| Single Family Residential	3 beds \| 2 baths \| 1,914 sq.ft.	$650,000	Airbnb cash on cash: -1.52% Traditional cash on cash: 2.06% Airbnb Rental Income: $1508 Traditional Rental Income: $3237 Airbnb ROI: -1.52% Traditional ROI: 2.06%
22 Pebblebrook Windsor, CT OFFER DEADLINE SUNDAY, 6/14 at 6PM. From the moment you pull up, the meticulous curb appea...	3 beds \| 3 baths \| 1,888 sq.ft.	$439,900	Airbnb cash on cash: -0.25% Traditional cash on cash: 5.59% Airbnb Rental Income: $1508 Traditional Rental Income: $3474 Airbnb ROI: -0.25% Traditional ROI: 5.59%
310 Kings Lndg #310 Windsor, CT 310 Kings Lndg #310, Windsor, CT 06095 \| Condo/Coop	2 beds \| 2 baths \| 1,263 sq.ft.	$339,900	Airbnb cash on cash: -3.44% Traditional cash on cash: 2.02% Airbnb Rental Income: $785 Traditional Rental Income: $2209 Airbnb ROI: -3.44% Traditional ROI: 2.02%
76 Sinclair St Windsor, CT 76 Sinclair St, Windsor, CT 06095 \| Single Family Residential	3 beds \| 2 baths \| 1,841 sq.ft.	$349,900	Airbnb cash on cash: -0.15% Traditional cash on cash: 5.09% Airbnb Rental Income: $1508 Traditional Rental Income: $2789 Airbnb ROI: -0.15% Traditional ROI: 5.09%
123 Country Club Dr Windsor, CT 123 Country Club Dr, Windsor, CT 06095 \| Single Family Residential	4 beds \| 4 baths \| 3,104 sq.ft.	$500,000	Airbnb cash on cash: -0.53% Traditional cash on cash: 7.5% Airbnb Rental Income: $1792 Traditional Rental Income: $5060 Airbnb ROI: -0.53% Traditional ROI: 7.5%
33 Mechanic St #203 Windsor, CT 33 Mechanic St St #203, Windsor, CT 06095 \| Condo/Coop	2 beds \| 3 baths \| 1,622 sq.ft.	$394,499	Airbnb cash on cash: -3.7% Traditional cash on cash: 2.85% Airbnb Rental Income: $785 Traditional Rental Income: $2886 Airbnb ROI: -3.7% Traditional ROI: 2.85%
1943 Logans Way Windsor, CT Welcome to desirable Mills Landing, a 55+ Planned Unit Development (PUD) in Windsor's soug...	3 beds \| 2 baths \| 1,533 sq.ft.	$324,900	Airbnb cash on cash: 0.16% Traditional cash on cash: 6.11% Airbnb Rental Income: $1508 Traditional Rental Income: $2886 Airbnb ROI: 0.16% Traditional ROI: 6.11%
101 Abbey Lane Windsor, CT Welcome to this beautifully remodeled Raised Ranch, ideally situated at the end of a quiet...	3 beds \| 3 baths \| 1,200 sq.ft.	$390,000	Airbnb cash on cash: 0.24% Traditional cash on cash: 4.63% Airbnb Rental Income: $1508 Traditional Rental Income: $2674 Airbnb ROI: 0.24% Traditional ROI: 4.63%
266 Kings Landing #266 Windsor, CT Welcome home to this inviting 2-bedroom, 2-bathroom condo in a 55+ community, offering the...	2 beds \| 2 baths \| 1,732 sq.ft.	$385,000	Airbnb cash on cash: -2.89% Traditional cash on cash: 3.44% Airbnb Rental Income: $785 Traditional Rental Income: $2753 Airbnb ROI: -2.89% Traditional ROI: 3.44%
1 Walter's Way Windsor, CT 1 Walter's Way, Windsor, CT 06095 \| Single Family Residential	4 beds \| 3 baths \| 3,552 sq.ft.	$729,900	Airbnb cash on cash: -1.35% Traditional cash on cash: 3.28% Airbnb Rental Income: $1792 Traditional Rental Income: $4454 Airbnb ROI: -1.35% Traditional ROI: 3.28%
6 Sinclair St Windsor, CT 6 Sinclair St, Windsor, CT 06095 \| Single Family Residential	3 beds \| 1 baths \| 1,125 sq.ft.	$299,900	Airbnb cash on cash: 0.34% Traditional cash on cash: 1.95% Airbnb Rental Income: $1508 Traditional Rental Income: $1521 Airbnb ROI: 0.34% Traditional ROI: 1.95%
27 Eagleton Dr Windsor, CT 27 Eagleton Dr, Windsor, CT 06095 \| Single Family Residential	3 beds \| 1 baths \| 1,818 sq.ft.	$390,000	Airbnb cash on cash: -0.52% Traditional cash on cash: 2.09% Airbnb Rental Income: $1508 Traditional Rental Income: $2044 Airbnb ROI: -0.52% Traditional ROI: 2.09%
41 Marble Faun Ln #41 Windsor, CT 41 Marble Faun Ln #41, Windsor, CT 06095 \| Condo/Coop	3 beds \| 2 baths \| 2,419 sq.ft.	$509,000	Airbnb cash on cash: -2.29% Traditional cash on cash: 1.89% Airbnb Rental Income: $1508 Traditional Rental Income: $3060 Airbnb ROI: -2.29% Traditional ROI: 1.89%
283 Strawberry Cir Windsor, CT 283 Strawberry Cir, Windsor, CT 06095 \| Condo/Coop	2 beds \| 1 baths \| 1,193 sq.ft.	$300,000	Airbnb cash on cash: -3.39% Traditional cash on cash: 0.49% Airbnb Rental Income: $785 Traditional Rental Income: $1559 Airbnb ROI: -3.39% Traditional ROI: 0.49%
66 Country Club Dr Windsor, CT This well-maintained 4-bedroom, 2.5-bath Colonial sits on nearly half an acre, offering a ...	4 beds \| 2 baths \| 1,976 sq.ft.	$435,000	Airbnb cash on cash: 0.34% Traditional cash on cash: 6.48% Airbnb Rental Income: $1792 Traditional Rental Income: $3809 Airbnb ROI: 0.34% Traditional ROI: 6.48%
31 Winthrop Rd Windsor, CT Welcome to 31 Winthrop Road, nestled in a serene and beautiful section of Windsor, Connect...	4 beds \| 3 baths \| 2,170 sq.ft.	$499,000	Airbnb cash on cash: 0.11% Traditional cash on cash: 7.72% Airbnb Rental Income: $1792 Traditional Rental Income: $4853 Airbnb ROI: 0.11% Traditional ROI: 7.72%
30 Hampden Pl Windsor, CT 30 Hampden Pl, Windsor, CT 06095 \| Single Family Residential	4 beds \| 2 baths \| 2,128 sq.ft.	$469,900	Airbnb cash on cash: -0.37% Traditional cash on cash: 3.93% Airbnb Rental Income: $1792 Traditional Rental Income: $3194 Airbnb ROI: -0.37% Traditional ROI: 3.93%
104 Benjamin Ct #104 Windsor, CT 104 Benjamin Ct #104, Windsor, CT 06095 \| Condo/Coop	4 beds \| 4 baths \| 2,450 sq.ft.	$469,900	Airbnb cash on cash: -0.52% Traditional cash on cash: 8.08% Airbnb Rental Income: $1792 Traditional Rental Income: $5083 Airbnb ROI: -0.52% Traditional ROI: 8.08%
36 Woodybrook Rd Windsor, CT Welcome to Windsor! This well-maintained home offers a bright, functional layout with comf...	3 beds \| 2 baths \| 1,229 sq.ft.	$315,000	Airbnb cash on cash: 0.67% Traditional cash on cash: 5.88% Airbnb Rental Income: $1508 Traditional Rental Income: $2611 Airbnb ROI: 0.67% Traditional ROI: 5.88%

Real Estate investment in Windsor, CT

There are 38 properties for sale in the city of Windsor . The median list price in Windsor is $602,475 and the average price per square foot is $194. In July 2026, the average monthly cash on cash return in Windsor is 5.00%. The average monthly rental income in Windsor is $3,009.

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

There are 38 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 $1,508.

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: 0.22%

Traditional cash on cash: 6.86%

Airbnb Rental Income: $1508

Traditional Rental Income: $3433

Airbnb ROI: 0.22%

Traditional ROI: 6.86%

9 Washington Rd

Windsor, CT

4 beds | 3 baths | 2,027 sq.ft.

$469,900

Airbnb cash on cash: -0.37%

Traditional cash on cash: 5.59%

Airbnb Rental Income: $1792

Traditional Rental Income: $3925

Airbnb ROI: -0.37%

Traditional ROI: 5.59%

58 Amanda Cir

Windsor, CT

3 beds | N/A baths | 1,952 sq.ft.

$449,000

Airbnb cash on cash: -0.27%

Traditional cash on cash: 5.5%

Airbnb Rental Income: $1508

Traditional Rental Income: $3493

Airbnb ROI: -0.27%

Traditional ROI: 5.5%

268 High Path Rd #268

Windsor, CT

3 beds | 2 baths | 1,390 sq.ft.

$239,900

Airbnb cash on cash: -2.37%

Traditional cash on cash: 3.96%

Airbnb Rental Income: $1508

Traditional Rental Income: $2502

Airbnb ROI: -2.37%

Traditional ROI: 3.96%

318 Capen St

Windsor, CT

3 beds | 2 baths | 2,160 sq.ft.

$599,900

Airbnb cash on cash: -1.38%

Traditional cash on cash: 2.08%

Airbnb Rental Income: $1508

Traditional Rental Income: $3009

Airbnb ROI: -1.38%

Traditional ROI: 2.08%

25 Matthew Ln

Windsor, CT

N/A beds | N/A baths | N/A

$289,000

Airbnb cash on cash: 0.2%

Traditional cash on cash: -0.24%

Airbnb Rental Income: $1420

Traditional Rental Income: $874

Airbnb ROI: 0.2%

Traditional ROI: -0.24%

490 Old Day Hill Rd

Windsor, CT

N/A beds | N/A baths | N/A

$325,000

Airbnb cash on cash: -0.17%

Traditional cash on cash: -0.53%

Airbnb Rental Income: $1420

Traditional Rental Income: $884

Airbnb ROI: -0.17%

Traditional ROI: -0.53%

1333 Palisado Ave

Windsor, CT

N/A beds | N/A baths | N/A

$95,000

Airbnb cash on cash: 6.67%

Traditional cash on cash: 6.43%

Airbnb Rental Income: $1420

Traditional Rental Income: $972

Airbnb ROI: 6.67%