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
129 E Lake Street Winchester, CT A true vacation retreat on the shore of Highland Lake! Rare offering in exceptional condit...	3 beds \| 4 baths \| 2,699 sq.ft.	$1,495,000	Airbnb cash on cash: -1.83% Traditional cash on cash: 1.64% Airbnb Rental Income: $1703 Traditional Rental Income: $6050 Airbnb ROI: -1.83% Traditional ROI: 1.64%
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: -0.34% Traditional cash on cash: 1.07% Airbnb Rental Income: $1703 Traditional Rental Income: $2057 Airbnb ROI: -0.34% Traditional ROI: 1.07%
90 Colony Drive Winchester, CT Turnkey Winsted gem completely renovated inside & out! Get ready to just move and and not ...	3 beds \| 1 baths \| 1,282 sq.ft.	$335,000	Airbnb cash on cash: 1.49% Traditional cash on cash: 4.68% Airbnb Rental Income: $1703 Traditional Rental Income: $2232 Airbnb ROI: 1.49% Traditional ROI: 4.68%
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%
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%
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 \| 1,556 sq.ft.	$1,200,000	Airbnb cash on cash: -1.32% Traditional cash on cash: 1.4% Airbnb Rental Income: $1703 Traditional Rental Income: $4265 Airbnb ROI: -1.32% Traditional ROI: 1.4%
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: 0.48% Traditional cash on cash: 3.64% Airbnb Rental Income: $2098 Traditional Rental Income: $3768 Airbnb ROI: 0.48% Traditional ROI: 3.64%
35 Riveredge Drive #35 Winchester, CT Charming Riverview Townhouse with Patio Enjoy easy living in this well-located two-bedroom...	2 beds \| 2 baths \| 992 sq.ft.	$159,500	Airbnb cash on cash: -0.37% Traditional cash on cash: 7.83% Airbnb Rental Income: $1269 Traditional Rental Income: $2117 Airbnb ROI: -0.37% Traditional ROI: 7.83%
156 Shore Drive Winchester, CT Summer is just around the corner, and this is your opportunity to own a highly sought-afte...	5 beds \| 2 baths \| 1,258 sq.ft.	$779,900	Airbnb cash on cash: N/A Traditional cash on cash: 1.82% Airbnb Rental Income: $null Traditional Rental Income: $3118 Airbnb ROI: N/A Traditional ROI: 1.82%
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: 0.51% Traditional cash on cash: 3.47% Airbnb Rental Income: $1269 Traditional Rental Income: $1812 Airbnb ROI: 0.51% Traditional ROI: 3.47%
1 Hamill Drive Winchester, CT Step into luxury in this nicely updated 3-bedroom raised ranch, perfectly positioned on a ...	3 beds \| 2 baths \| 1,600 sq.ft.	$349,900	Airbnb cash on cash: 1.35% Traditional cash on cash: 6.6% Airbnb Rental Income: $1703 Traditional Rental Income: $2956 Airbnb ROI: 1.35% Traditional ROI: 6.6%
123 Old N Road Winchester, CT This one-of-a-kind custom Ranch is tucked well back from the road for exceptional privacy ...	3 beds \| 2 baths \| 1,781 sq.ft.	$425,000	Airbnb cash on cash: 0.55% Traditional cash on cash: 5.13% Airbnb Rental Income: $1703 Traditional Rental Income: $3056 Airbnb ROI: 0.55% Traditional ROI: 5.13%
111 Riverton Road unit: 28 Winchester, CT Stop paying rent and get into the housing market with this affordable end-unit townhouse! ...	2 beds \| 2 baths \| 1,204 sq.ft.	$184,900	Airbnb cash on cash: 1.89% Traditional cash on cash: 9.53% Airbnb Rental Income: $1269 Traditional Rental Income: $2212 Airbnb ROI: 1.89% Traditional ROI: 9.53%

Real Estate investment in Winchester, CT

There are 17 properties for sale in the city of Winchester . The median list price in Winchester is $419,000 and the average price per square foot is $191. In May 2026, the average monthly cash on cash return in Winchester is 5.00%. The average monthly rental income in Winchester is $3,075.

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

There are 17 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 $3,075.

Your search for investment property begins and ends here

Investment Property for Sale in Winchester, CT

129 E Lake Street

Winchester, CT

3 beds | 4 baths | 2,699 sq.ft.

$1,495,000

Airbnb cash on cash: -1.83%

Traditional cash on cash: 1.64%

Airbnb Rental Income: $1703

Traditional Rental Income: $6050

Airbnb ROI: -1.83%

Traditional ROI: 1.64%

162 Spencer Hill Road

Winchester, CT

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

$625,000

Airbnb cash on cash: -0.34%

Traditional cash on cash: 1.07%

Airbnb Rental Income: $1703

Traditional Rental Income: $2057

Airbnb ROI: -0.34%

Traditional ROI: 1.07%

90 Colony Drive

Winchester, CT

3 beds | 1 baths | 1,282 sq.ft.

$335,000

Airbnb cash on cash: 1.49%

Traditional cash on cash: 4.68%

Airbnb Rental Income: $1703

Traditional Rental Income: $2232

Airbnb ROI: 1.49%

Traditional ROI: 4.68%

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%

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%

722 Lake Drive

Winchester, CT

3 beds | 3 baths | 1,556 sq.ft.

$1,200,000

Airbnb cash on cash: -1.32%

Traditional cash on cash: 1.4%

Airbnb Rental Income: $1703

Traditional Rental Income: $4265

Airbnb ROI: -1.32%

Traditional ROI: 1.4%

436 Main Street

Winchester, CT

4 beds | 2 baths | 5,389 sq.ft.

$750,000

Airbnb cash on cash: 0.48%

Traditional cash on cash: 3.64%

Airbnb Rental Income: $2098

Traditional Rental Income: $3768

Airbnb ROI: 0.48%

Traditional ROI: 3.64%

35 Riveredge Drive #35

Winchester, CT

2 beds | 2 baths | 992 sq.ft.

$159,500

Airbnb cash on cash: -0.37%

Traditional cash on cash: 7.83%

Airbnb Rental Income: $1269

Traditional Rental Income: $2117

Airbnb ROI: -0.37%