Real Estate Investment Properties for Sale in Winchester, CT

Looking for investment property in Winchester, CT with high ROI ?

Explore a variety of short-term homes & houses in Winchester, CT. Invest wisely with VRBO & Winchester, 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 Winchester, CT

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
8 Oak Street Winchester, CT Discover a low maintenance and hassle-free alternative to condo living with this easy-to-m...	2 beds \| 2 baths \| 832 sq.ft.	$179,900	Airbnb cash on cash: 2.65% Traditional cash on cash: 9.77% Airbnb Rental Income: $1289 Traditional Rental Income: $2105 Airbnb ROI: 2.65% Traditional ROI: 9.77%
146 SPENCER HILL ROAD Winchester, CT Invest with success and buy through Auction.com. This bank-owned investment property is a ...	5 beds \| 3 baths \| 3,204 sq.ft.	$681,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.7% Airbnb Rental Income: $null Traditional Rental Income: $4428 Airbnb ROI: N/A Traditional ROI: 3.7%
118 Meadow Street Winchester, CT This charming historic home, built in 1860, blends timeless character with thoughtful upda...	3 beds \| 2 baths \| 1,652 sq.ft.	$290,000	Airbnb cash on cash: 0.77% Traditional cash on cash: 3.17% Airbnb Rental Income: $1611 Traditional Rental Income: $1808 Airbnb ROI: 0.77% Traditional ROI: 3.17%
77 Hubbard Street Winchester, CT Discover this versatile two-family residence offering a blend of modern updates and timele...	6 beds \| 2 baths \| 2,699 sq.ft.	$299,900	Airbnb cash on cash: N/A Traditional cash on cash: 9.14% Airbnb Rental Income: $null Traditional Rental Income: $3553 Airbnb ROI: N/A Traditional ROI: 9.14%
55 Walnut Street Winchester, CT Timeless Victorian with Endless Possibilities.Step into a piece of history with this stunn...	5 beds \| 4 baths \| 5,016 sq.ft.	$499,999	Airbnb cash on cash: N/A Traditional cash on cash: 9.3% Airbnb Rental Income: $null Traditional Rental Income: $5903 Airbnb ROI: N/A Traditional ROI: 9.3%
722 Lake Drive Winchester, CT Welcome to lake living at its finest! Built in 2014 and first time on the market. Impeccab...	3 beds \| 3 baths \| 2,420 sq.ft.	$1,270,000	Airbnb cash on cash: -2.23% Traditional cash on cash: 0.4% Airbnb Rental Income: $1611 Traditional Rental Income: $4265 Airbnb ROI: -2.23% Traditional ROI: 0.4%
111 Riverton Road #APT 90 Winchester, CT Discover the ease of condo living with the charm of a riverside retreat at Riverwalk Condo...	2 beds \| 2 baths \| 1,204 sq.ft.	$179,900	Airbnb cash on cash: -0.87% Traditional cash on cash: 9.82% Airbnb Rental Income: $1289 Traditional Rental Income: $2715 Airbnb ROI: -0.87% Traditional ROI: 9.82%
111 Riverton Road #Apt 61 Winchester, CT Beautifully Maintained Townhouse Condo Located in Small, Quiet Complex in Charming Winches...	2 beds \| 2 baths \| 1,204 sq.ft.	$194,900	Airbnb cash on cash: -1.04% Traditional cash on cash: 7.4% Airbnb Rental Income: $1289 Traditional Rental Income: $2448 Airbnb ROI: -1.04% Traditional ROI: 7.4%
440 Platt Hill Road Winchester, CT Distinctive Country Estate with Two Homes on 9.6 Rolling Acres Set amid 9.6 picturesque c...	4 beds \| 3 baths \| 3,416 sq.ft.	$500,000	Airbnb cash on cash: 2.33% Traditional cash on cash: 7.28% Airbnb Rental Income: $3395 Traditional Rental Income: $4956 Airbnb ROI: 2.33% Traditional ROI: 7.28%
197 Spencer Hill Road Winchester, CT Discover the charm of this spacious contemporary Cape, set on a peaceful one-acre lot in a...	3 beds \| 2 baths \| 2,167 sq.ft.	$499,000	Airbnb cash on cash: -0.85% Traditional cash on cash: 3.78% Airbnb Rental Income: $1611 Traditional Rental Income: $3312 Airbnb ROI: -0.85% Traditional ROI: 3.78%
156 Lincoln Avenue Winchester, CT Welcome to your cozy cottage retreat in beautiful Highland Lake Community. Views of the la...	2 beds \| 1 baths \| 702 sq.ft.	$299,900	Airbnb cash on cash: -0.31% Traditional cash on cash: 3.25% Airbnb Rental Income: $1289 Traditional Rental Income: $1890 Airbnb ROI: -0.31% Traditional ROI: 3.25%
436 Main Street Winchester, CT One-of-a-Kind opportunity with 4 apartments plus a turnkey, award-winning restaurant in th...	4 beds \| 2 baths \| 5,389 sq.ft.	$750,000	Airbnb cash on cash: 0.52% Traditional cash on cash: 2.13% Airbnb Rental Income: $3395 Traditional Rental Income: $3768 Airbnb ROI: 0.52% Traditional ROI: 2.13%
49 Walnut Street Winchester, CT Well-maintained two-family home situated on a large, level lot in an area of well-cared-fo...	5 beds \| 2 baths \| 2,344 sq.ft.	$299,900	Airbnb cash on cash: N/A Traditional cash on cash: 8.95% Airbnb Rental Income: $null Traditional Rental Income: $3498 Airbnb ROI: N/A Traditional ROI: 8.95%
148 Danbury Quarter Road Winchester, CT Welcome to this Wonderful Historic Colonial Farmhouse.. This home has been lovingly remode...	4 beds \| 2 baths \| 1,999 sq.ft.	$339,900	Airbnb cash on cash: 4.86% Traditional cash on cash: 7.13% Airbnb Rental Income: $3395 Traditional Rental Income: $3365 Airbnb ROI: 4.86% Traditional ROI: 7.13%
720 Main Street Winchester, CT Prime Mixed-Use Opportunity in Downtown Winsted! High-visibility two-story building locate...	3 beds \| 2 baths \| 1,909 sq.ft.	$395,000	Airbnb cash on cash: -0.25% Traditional cash on cash: 4.58% Airbnb Rental Income: $1611 Traditional Rental Income: $2945 Airbnb ROI: -0.25% Traditional ROI: 4.58%
106 Rockwell Street Winchester, CT Looking to expand your investment portfolio-or live nearly rent-free while building one? T...	4 beds \| 3 baths \| 1,874 sq.ft.	$299,900	Airbnb cash on cash: 5.91% Traditional cash on cash: 9.22% Airbnb Rental Income: $3395 Traditional Rental Income: $3574 Airbnb ROI: 5.91% Traditional ROI: 9.22%
95 Nalette Drive Winchester, CT Stunning Contemporary Home on a Quiet Corner Lot. This unique home offers a beautifully u...	3 beds \| 3 baths \| 2,356 sq.ft.	$365,000	Airbnb cash on cash: -0.02% Traditional cash on cash: 7.98% Airbnb Rental Income: $1611 Traditional Rental Income: $3893 Airbnb ROI: -0.02% Traditional ROI: 7.98%
208 Spencer Hill Road Winchester, CT Discover this beautifully maintained 3-bedroom, 1.5-bath Colonial set on a level one-acre ...	3 beds \| 2 baths \| 1,969 sq.ft.	$399,000	Airbnb cash on cash: -0.28% Traditional cash on cash: 5.55% Airbnb Rental Income: $1611 Traditional Rental Income: $3337 Airbnb ROI: -0.28% Traditional ROI: 5.55%

Real Estate investment in Winchester, CT

There are 20 properties for sale in the city of Winchester . The median list price in Winchester is $329,900 and the average price per square foot is $143. In December 2025, the average monthly cash on cash return in Winchester is 7.00%. The average monthly rental income in Winchester is $3,351.

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

There are 20 investment properties available for sale in Winchester.

In 2025, the best neighborhood to buy investment property is Winchester.

The ROI for Short-Term is higher than the Long-Term in Winchester with average rental income of $1,611.

Your search for investment property begins and ends here

Investment Property for Sale in Winchester, CT

8 Oak Street

Winchester, CT

2 beds | 2 baths | 832 sq.ft.

$179,900

Airbnb cash on cash: 2.65%

Traditional cash on cash: 9.77%

Airbnb Rental Income: $1289

Traditional Rental Income: $2105

Airbnb ROI: 2.65%

Traditional ROI: 9.77%

146 SPENCER HILL ROAD

Winchester, CT

5 beds | 3 baths | 3,204 sq.ft.

$681,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.7%

Airbnb Rental Income: $null

Traditional Rental Income: $4428

Airbnb ROI: N/A

Traditional ROI: 3.7%

118 Meadow Street

Winchester, CT

3 beds | 2 baths | 1,652 sq.ft.

$290,000

Airbnb cash on cash: 0.77%

Traditional cash on cash: 3.17%

Airbnb Rental Income: $1611

Traditional Rental Income: $1808

Airbnb ROI: 0.77%

Traditional ROI: 3.17%

77 Hubbard Street

Winchester, CT

6 beds | 2 baths | 2,699 sq.ft.

$299,900

Airbnb cash on cash: N/A

Traditional cash on cash: 9.14%

Airbnb Rental Income: $null

Traditional Rental Income: $3553

Airbnb ROI: N/A

Traditional ROI: 9.14%

55 Walnut Street

Winchester, CT

5 beds | 4 baths | 5,016 sq.ft.

$499,999

Airbnb cash on cash: N/A

Traditional cash on cash: 9.3%

Airbnb Rental Income: $null

Traditional Rental Income: $5903

Airbnb ROI: N/A

Traditional ROI: 9.3%

722 Lake Drive

Winchester, CT

3 beds | 3 baths | 2,420 sq.ft.

$1,270,000

Airbnb cash on cash: -2.23%

Traditional cash on cash: 0.4%

Airbnb Rental Income: $1611

Traditional Rental Income: $4265

Airbnb ROI: -2.23%

Traditional ROI: 0.4%

111 Riverton Road #APT 90

Winchester, CT

2 beds | 2 baths | 1,204 sq.ft.

$179,900

Airbnb cash on cash: -0.87%

Traditional cash on cash: 9.82%

Airbnb Rental Income: $1289

Traditional Rental Income: $2715

Airbnb ROI: -0.87%

Traditional ROI: 9.82%

111 Riverton Road #Apt 61

Winchester, CT

2 beds | 2 baths | 1,204 sq.ft.

$194,900

Airbnb cash on cash: -1.04%

Traditional cash on cash: 7.4%

Airbnb Rental Income: $1289

Traditional Rental Income: $2448

Airbnb ROI: -1.04%