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
162 Spencer Hill Road Winchester, CT Experience the beauty and privacy of this pristine log home set on 16.53 picturesque acres...	3 beds \| 3 baths \| 2,144 sq.ft.	$625,000	Airbnb cash on cash: 0.17% Traditional cash on cash: 1.07% Airbnb Rental Income: $2065 Traditional Rental Income: $2057 Airbnb ROI: 0.17% Traditional ROI: 1.07%
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%
624 Wynne Road Winchester, CT Exceptional opportunity to build near one of Northwest Connecticut's most desirable lake c...	2 beds \| 1 baths \| 672 sq.ft.	$174,900	Airbnb cash on cash: 4.39% Traditional cash on cash: 5.68% Airbnb Rental Income: $1633 Traditional Rental Income: $1388 Airbnb ROI: 4.39% Traditional ROI: 5.68%
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: 10% Airbnb Rental Income: $null Traditional Rental Income: $3553 Airbnb ROI: N/A Traditional ROI: 10%
424 E Wakefield Boulevard Winchester, CT Stunning Lakehouse! Victorian charm! One of the earliest Highland Lake homes with extensiv...	5 beds \| 2 baths \| 3,693 sq.ft.	$1,595,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.51% Airbnb Rental Income: $null Traditional Rental Income: $4368 Airbnb ROI: N/A Traditional ROI: 0.51%
621 Wynne Road Winchester, CT Tucked away on a private road in the sought-after Highland Lake district, this impeccably ...	2 beds \| 1 baths \| 975 sq.ft.	$339,900	Airbnb cash on cash: 1.46% Traditional cash on cash: 3.47% Airbnb Rental Income: $1633 Traditional Rental Income: $1812 Airbnb ROI: 1.46% Traditional ROI: 3.47%
102 Wallens Street Winchester, CT This move-in-ready Colonial-style home blends classic charm with modern updates. Featuring...	3 beds \| 2 baths \| 1,898 sq.ft.	$349,900	Airbnb cash on cash: 1.75% Traditional cash on cash: 6.5% Airbnb Rental Income: $2065 Traditional Rental Income: $3094 Airbnb ROI: 1.75% Traditional ROI: 6.5%
217 Walnut Street Winchester, CT In-Town Victorian 2-Family - Exceptional Condition & Versatility Rare opportunity to own a...	5 beds \| 4 baths \| 2,779 sq.ft.	$399,000	Airbnb cash on cash: N/A Traditional cash on cash: 11.25% Airbnb Rental Income: $null Traditional Rental Income: $5227 Airbnb ROI: N/A Traditional ROI: 11.25%
147 E Wakefield Boulevard Winchester, CT Come enjoy Highland Lake living just in time for Summer. Relax in this one level living, c...	2 beds \| 1 baths \| 702 sq.ft.	$299,900	Airbnb cash on cash: 2.07% Traditional cash on cash: 4.53% Airbnb Rental Income: $1633 Traditional Rental Income: $1865 Airbnb ROI: 2.07% Traditional ROI: 4.53%

Real Estate investment in Winchester, CT

There are 14 properties for sale in the city of Winchester . The median list price in Winchester is $415,000 and the average price per square foot is $189. In June 2026, the average monthly cash on cash return in Winchester is 5.00%. The average monthly rental income in Winchester is $3,186.

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

There are 14 investment properties available for sale in Winchester.

In 2026, 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 $3,186.

Your search for investment property begins and ends here

Investment Property for Sale in Winchester, CT

162 Spencer Hill Road

Winchester, CT

3 beds | 3 baths | 2,144 sq.ft.

$625,000

Airbnb cash on cash: 0.17%

Traditional cash on cash: 1.07%

Airbnb Rental Income: $2065

Traditional Rental Income: $2057

Airbnb ROI: 0.17%

Traditional ROI: 1.07%

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%

624 Wynne Road

Winchester, CT

2 beds | 1 baths | 672 sq.ft.

$174,900

Airbnb cash on cash: 4.39%

Traditional cash on cash: 5.68%

Airbnb Rental Income: $1633

Traditional Rental Income: $1388

Airbnb ROI: 4.39%

Traditional ROI: 5.68%

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: 10%

Airbnb Rental Income: $null

Traditional Rental Income: $3553

Airbnb ROI: N/A

Traditional ROI: 10%

424 E Wakefield Boulevard

Winchester, CT

5 beds | 2 baths | 3,693 sq.ft.

$1,595,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.51%

Airbnb Rental Income: $null

Traditional Rental Income: $4368

Airbnb ROI: N/A

Traditional ROI: 0.51%

621 Wynne Road

Winchester, CT

2 beds | 1 baths | 975 sq.ft.

$339,900

Airbnb cash on cash: 1.46%

Traditional cash on cash: 3.47%

Airbnb Rental Income: $1633

Traditional Rental Income: $1812

Airbnb ROI: 1.46%

Traditional ROI: 3.47%

102 Wallens Street

Winchester, CT

3 beds | 2 baths | 1,898 sq.ft.

$349,900

Airbnb cash on cash: 1.75%

Traditional cash on cash: 6.5%

Airbnb Rental Income: $2065

Traditional Rental Income: $3094

Airbnb ROI: 1.75%

Traditional ROI: 6.5%

217 Walnut Street

Winchester, CT

5 beds | 4 baths | 2,779 sq.ft.

$399,000

Airbnb cash on cash: N/A

Traditional cash on cash: 11.25%

Airbnb Rental Income: $null

Traditional Rental Income: $5227

Airbnb ROI: N/A