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
152 East Lake Street Winchester, CT Well-maintained and move-in ready, this charming one-level ranch offers 900 square feet of...	2 beds \| 2 baths \| 900 sq.ft.	$299,000	Airbnb cash on cash: 3.37% Traditional cash on cash: 5.82% Airbnb Rental Income: $2117 Traditional Rental Income: $2264 Airbnb ROI: 3.37% Traditional ROI: 5.82%
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%
39 Orchard Street Winchester, CT Seller is working on final details. Welcome to your dream home, 39 Orchard st ! This beaut...	3 beds \| 2 baths \| 1,200 sq.ft.	$279,923	Airbnb cash on cash: 4.4% Traditional cash on cash: 3.74% Airbnb Rental Income: $2365 Traditional Rental Income: $1607 Airbnb ROI: 4.4% Traditional ROI: 3.74%
25 Center Street Winchester, CT Don't miss this unique opportunity to own a multi family residential property and an offic...	3 beds \| 3 baths \| 2,754 sq.ft.	$319,900	Airbnb cash on cash: 2.5% Traditional cash on cash: 1.13% Airbnb Rental Income: $2365 Traditional Rental Income: $1369 Airbnb ROI: 2.5% Traditional ROI: 1.13%
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.	$515,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.95% Airbnb Rental Income: $null Traditional Rental Income: $5903 Airbnb ROI: N/A Traditional ROI: 8.95%
111 South Road Winchester, CT Perched up higher than the rest with sweeping views up a private driveway in beautiful Win...	3 beds \| 4 baths \| 4,953 sq.ft.	$779,900	Airbnb cash on cash: -0.8% Traditional cash on cash: 4.25% Airbnb Rental Income: $2365 Traditional Rental Income: $5454 Airbnb ROI: -0.8% Traditional ROI: 4.25%
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: -1.7% Traditional cash on cash: 0.4% Airbnb Rental Income: $2365 Traditional Rental Income: $4265 Airbnb ROI: -1.7% Traditional ROI: 0.4%
147 Smith Hill Road Winchester, CT HUGE PRICE REDUCTION!! Make this beautiful Cape your home! Features 4 spacious bedrooms a...	4 beds \| 2 baths \| 1,910 sq.ft.	$350,000	Airbnb cash on cash: 2.07% Traditional cash on cash: 7.23% Airbnb Rental Income: $2382 Traditional Rental Income: $3494 Airbnb ROI: 2.07% Traditional ROI: 7.23%
441 Platt Hill Road Winchester, CT Welcome to 441 Platt Hill Road - a home that offers warmth, charm, and plenty of space to ...	5 beds \| 3 baths \| 3,404 sq.ft.	$599,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.55% Airbnb Rental Income: $null Traditional Rental Income: $4951 Airbnb ROI: N/A Traditional ROI: 5.55%
126 Forest Avenue Winchester, CT Charming Cape 2 minutes to Highland Lake. Welcome to this one owner, 3 bedroom, two bath C...	3 beds \| 2 baths \| 1,833 sq.ft.	$355,750	Airbnb cash on cash: 1.94% Traditional cash on cash: 6.28% Airbnb Rental Income: $2365 Traditional Rental Income: $3232 Airbnb ROI: 1.94% Traditional ROI: 6.28%
101 Norfolk Road Winchester, CT Beautifully updated Raised- Ranch retreat on 1.33 wooded acres! Nestled in a serene, natur...	2 beds \| 1 baths \| 1,880 sq.ft.	$299,000	Airbnb cash on cash: 2.15% Traditional cash on cash: 3.78% Airbnb Rental Income: $2117 Traditional Rental Income: $2033 Airbnb ROI: 2.15% Traditional ROI: 3.78%
111 Torringford Street #APT 25 Winchester, CT Two bedrooms, two baths plus an office - play room... New boiler and hot water heater in 2...	2 beds \| 2 baths \| 1,156 sq.ft.	$179,900	Airbnb cash on cash: 3.39% Traditional cash on cash: 8.1% Airbnb Rental Income: $2117 Traditional Rental Income: $2382 Airbnb ROI: 3.39% Traditional ROI: 8.1%
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.	$199,900	Airbnb cash on cash: 2.55% Traditional cash on cash: 8.56% Airbnb Rental Income: $2117 Traditional Rental Income: $2715 Airbnb ROI: 2.55% Traditional ROI: 8.56%
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.	$204,900	Airbnb cash on cash: 2.41% Traditional cash on cash: 6.9% Airbnb Rental Income: $2117 Traditional Rental Income: $2448 Airbnb ROI: 2.41% Traditional ROI: 6.9%
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: 0.52% Traditional cash on cash: 7.28% Airbnb Rental Income: $2382 Traditional Rental Income: $4956 Airbnb ROI: 0.52% Traditional ROI: 7.28%

Real Estate investment in Winchester, CT

There are 26 properties for sale in the city of Winchester . The median list price in Winchester is $309,900 and the average price per square foot is $139. In October 2025, the average monthly cash on cash return in Winchester is 7.00%. The average monthly rental income in Winchester is $3,067.

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

There are 26 investment properties available for sale in Winchester.

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

The ROI for Long-Term is higher than the Short-Term in Winchester with average rental income of $3,067.

Your search for investment property begins and ends here

Investment Property for Sale in Winchester, CT

152 East Lake Street

Winchester, CT

2 beds | 2 baths | 900 sq.ft.

$299,000

Airbnb cash on cash: 3.37%

Traditional cash on cash: 5.82%

Airbnb Rental Income: $2117

Traditional Rental Income: $2264

Airbnb ROI: 3.37%

Traditional ROI: 5.82%

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%

39 Orchard Street

Winchester, CT

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

$279,923

Airbnb cash on cash: 4.4%

Traditional cash on cash: 3.74%

Airbnb Rental Income: $2365

Traditional Rental Income: $1607

Airbnb ROI: 4.4%

Traditional ROI: 3.74%

25 Center Street

Winchester, CT

3 beds | 3 baths | 2,754 sq.ft.

$319,900

Airbnb cash on cash: 2.5%

Traditional cash on cash: 1.13%

Airbnb Rental Income: $2365

Traditional Rental Income: $1369

Airbnb ROI: 2.5%

Traditional ROI: 1.13%

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.

$515,000

Airbnb cash on cash: N/A

Traditional cash on cash: 8.95%

Airbnb Rental Income: $null

Traditional Rental Income: $5903

Airbnb ROI: N/A

Traditional ROI: 8.95%

111 South Road

Winchester, CT

3 beds | 4 baths | 4,953 sq.ft.

$779,900

Airbnb cash on cash: -0.8%

Traditional cash on cash: 4.25%

Airbnb Rental Income: $2365

Traditional Rental Income: $5454

Airbnb ROI: -0.8%

Traditional ROI: 4.25%

722 Lake Drive

Winchester, CT

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

$1,270,000

Airbnb cash on cash: -1.7%

Traditional cash on cash: 0.4%

Airbnb Rental Income: $2365

Traditional Rental Income: $4265

Airbnb ROI: -1.7%