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.

Golden Highlands Investment Property for Sale in Winchester, CT

Search for Golden Highlands Investment Property for Sale in Winchester, Connecticut. Browse all of Mashvisor’s Golden Highlands Investment Property listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 19 Golden Highlands Investment Property listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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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%
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%
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%
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%
00 Chapel Rd Winchester, CT 00 Chapel Rd, Winchester, CT 06098 \| Other	N/A beds \| N/A baths \| 8,862 sq.ft.	$200,000	Airbnb cash on cash: 2.3% Traditional cash on cash: 1.06% Airbnb Rental Income: $1569 Traditional Rental Income: $884 Airbnb ROI: 2.3% Traditional ROI: 1.06%
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%
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%

Your search for investment property begins and ends here

Golden Highlands 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%

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%

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%

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%

00 Chapel Rd

Winchester, CT

N/A beds | N/A baths | 8,862 sq.ft.

$200,000

Airbnb cash on cash: 2.3%

Traditional cash on cash: 1.06%

Airbnb Rental Income: $1569

Traditional Rental Income: $884

Airbnb ROI: 2.3%

Traditional ROI: 1.06%

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%