Real Estate Investment Properties for Sale in Winchester, KY

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

Explore a variety of short-term homes & houses in Winchester, KY. Invest wisely with VRBO & Winchester, KY Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Townhouses for Sale in Winchester, KY

Search for Townhouse for Sale in Winchester, Kentucky. Browse all of Mashvisor’s Townhouse listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 3 Townhouse 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
271 April Way Winchester, KY This charming 2 - story townhouse is in a prime location.. Welcome to this beautifully mai...	2 beds \| 2 baths \| 1,120 sq.ft.	$215,000	Airbnb cash on cash: -0.41% Traditional cash on cash: 5.57% Airbnb Rental Income: $590 Traditional Rental Income: $1520 Airbnb ROI: -0.41% Traditional ROI: 5.57%
109 Quail Ridge Road Winchester, KY Move-In Ready Brick Townhome with Garage and Fireplace Step into this charming brick townh...	2 beds \| 2 baths \| 1,197 sq.ft.	$189,500	Airbnb cash on cash: -0.31% Traditional cash on cash: 6.93% Airbnb Rental Income: $590 Traditional Rental Income: $1606 Airbnb ROI: -0.31% Traditional ROI: 6.93%
111 Quail Ridge Road Winchester, KY Move-In Ready Brick Townhome with Garage and Fireplace Step into this charming brick townh...	2 beds \| 2 baths \| 1,197 sq.ft.	$189,500	Airbnb cash on cash: -0.31% Traditional cash on cash: 6.93% Airbnb Rental Income: $590 Traditional Rental Income: $1606 Airbnb ROI: -0.31% Traditional ROI: 6.93%
Other Investment Properties for Sale in Winchester
2395 Becknerville Road Winchester , KY An exceptional offering of refined country living, this stunning 11-acre estate blends pri...	4 beds \| 4 baths \| 3,234 sq.ft.	$849,000	Airbnb cash on cash: -0.71% Traditional cash on cash: 2.49% Airbnb Rental Income: $1423 Traditional Rental Income: $3530 Airbnb ROI: -0.71% Traditional ROI: 2.49%
724 Terry Drive Winchester , KY Charming Split-Level Home in a Peaceful Winchester Neighborhood Discover this beautiful 3-...	3 beds \| 2 baths \| 2,250 sq.ft.	$279,500	Airbnb cash on cash: 1.72% Traditional cash on cash: 6% Airbnb Rental Income: $1466 Traditional Rental Income: $2162 Airbnb ROI: 1.72% Traditional ROI: 6%
149 Winn Ave Winchester , KY Welcome to this quad plex income producing property. It is a large lot and the property si...	12 beds \| 4 baths \| 4,010 sq.ft.	$290,000	Airbnb cash on cash: N/A Traditional cash on cash: 11.48% Airbnb Rental Income: $null Traditional Rental Income: $3514 Airbnb ROI: N/A Traditional ROI: 11.48%
300 Calmes Boulevard Winchester , KY Gorgeous & Spacious 3BR/2.5BA Home in Calmes Estates . Welcome to your dream home in the h...	3 beds \| 2 baths \| 2,636 sq.ft.	$379,717	Airbnb cash on cash: 0.79% Traditional cash on cash: 3.27% Airbnb Rental Income: $1466 Traditional Rental Income: $1919 Airbnb ROI: 0.79% Traditional ROI: 3.27%
213 Orchid Court Winchester , KY	4 beds \| 3 baths \| 1,776 sq.ft.	$325,000	Airbnb cash on cash: 1.1% Traditional cash on cash: 4.68% Airbnb Rental Income: $1423 Traditional Rental Income: $2088 Airbnb ROI: 1.1% Traditional ROI: 4.68%
407 Corinne Court Winchester , KY Welcome to 407 Corinne Court a beautifully maintained 3-bedroom, 2-bath all-electric home ...	3 beds \| 2 baths \| 1,352 sq.ft.	$274,900	Airbnb cash on cash: 1.77% Traditional cash on cash: 5.21% Airbnb Rental Income: $1466 Traditional Rental Income: $1924 Airbnb ROI: 1.77% Traditional ROI: 5.21%
175 Magnolia Street Winchester , KY Two homes on one lot. Informaton in listing is for the home in the front of the lot. Behin...	3 beds \| 1 baths \| 1,046 sq.ft.	$194,900	Airbnb cash on cash: 4.03% Traditional cash on cash: 5.95% Airbnb Rental Income: $1466 Traditional Rental Income: $1387 Airbnb ROI: 4.03% Traditional ROI: 5.95%
42 Mockingbird Valley Road Winchester , KY This is a perfect home for EVERY season.....enjoy multiple, interior gathering spaces and ...	3 beds \| 2 baths \| 2,961 sq.ft.	$452,500	Airbnb cash on cash: 0.37% Traditional cash on cash: 3.56% Airbnb Rental Income: $1466 Traditional Rental Income: $2386 Airbnb ROI: 0.37% Traditional ROI: 3.56%
142 Sturbridge Lane Winchester , KY All on one level, large master bedroom, HVAC less than 2 years old and upgrades made in th...	3 beds \| 2 baths \| 1,220 sq.ft.	$249,500	Airbnb cash on cash: 2.13% Traditional cash on cash: 4.55% Airbnb Rental Income: $1466 Traditional Rental Income: $1603 Airbnb ROI: 2.13% Traditional ROI: 4.55%
52 Hillcrest Drive Winchester , KY 3-bedroom, 2-bath home located in Winchester featuring a full walk-out basement that adds ...	3 beds \| 2 baths \| 2,050 sq.ft.	$216,000	Airbnb cash on cash: 2.74% Traditional cash on cash: 7.8% Airbnb Rental Income: $1466 Traditional Rental Income: $2068 Airbnb ROI: 2.74% Traditional ROI: 7.8%
114 Magnolia Street Winchester , KY Great opportunity for investors, flippers, or anyone looking for a project with tons of po...	2 beds \| 1 baths \| 910 sq.ft.	$99,000	Airbnb cash on cash: 0.33% Traditional cash on cash: 10.18% Airbnb Rental Income: $590 Traditional Rental Income: $1251 Airbnb ROI: 0.33% Traditional ROI: 10.18%
6 Monroe Avenue Winchester , KY Charming and Updated Home in the Heart of Winchester! Welcome to 6 Monroe Ave - a beautifu...	3 beds \| 2 baths \| 1,305 sq.ft.	$175,000	Airbnb cash on cash: 3.79% Traditional cash on cash: 8.03% Airbnb Rental Income: $1466 Traditional Rental Income: $1740 Airbnb ROI: 3.79% Traditional ROI: 8.03%
17 Euclid Avenue Winchester , KY Welcome home to 17 Euclid Ave in beautiful College Park area of Winchester. This three bed...	3 beds \| 2 baths \| 1,656 sq.ft.	$249,900	Airbnb cash on cash: 2.13% Traditional cash on cash: 3.87% Airbnb Rental Income: $1466 Traditional Rental Income: $1443 Airbnb ROI: 2.13% Traditional ROI: 3.87%
233 Cunningham Lane Winchester , KY Mini Farm Alert! This fabulous homestead is located less than 2 miles off the Mountain Par...	3 beds \| 2 baths \| 2,258 sq.ft.	$450,000	Airbnb cash on cash: 0.6% Traditional cash on cash: 4% Airbnb Rental Income: $1466 Traditional Rental Income: $2464 Airbnb ROI: 0.6% Traditional ROI: 4%
106 Gibson Way Winchester , KY This well maintained home offers 3 bedrooms, 2.5 bathrooms and a versatile bonus/flex area...	3 beds \| 2 baths \| 2,064 sq.ft.	$339,000	Airbnb cash on cash: 1.1% Traditional cash on cash: 5.7% Airbnb Rental Income: $1466 Traditional Rental Income: $2498 Airbnb ROI: 1.1% Traditional ROI: 5.7%

Your search for investment property begins and ends here

Townhouses for Sale in Winchester, KY

271 April Way

Winchester, KY

2 beds | 2 baths | 1,120 sq.ft.

$215,000

Airbnb cash on cash: -0.41%

Traditional cash on cash: 5.57%

Airbnb Rental Income: $590

Traditional Rental Income: $1520

Airbnb ROI: -0.41%

Traditional ROI: 5.57%

109 Quail Ridge Road

Winchester, KY

2 beds | 2 baths | 1,197 sq.ft.

$189,500

Airbnb cash on cash: -0.31%

Traditional cash on cash: 6.93%

Airbnb Rental Income: $590

Traditional Rental Income: $1606

Airbnb ROI: -0.31%

Traditional ROI: 6.93%

111 Quail Ridge Road

Winchester, KY

2 beds | 2 baths | 1,197 sq.ft.

$189,500

Airbnb cash on cash: -0.31%

Traditional cash on cash: 6.93%

Airbnb Rental Income: $590

Traditional Rental Income: $1606

Airbnb ROI: -0.31%

Traditional ROI: 6.93%

Other Investment Properties for Sale in Winchester

Winchester , KY

4 beds | 4 baths | 3,234 sq.ft.

$849,000

Airbnb cash on cash: -0.71%

Traditional cash on cash: 2.49%

Airbnb Rental Income: $1423

Traditional Rental Income: $3530

Airbnb ROI: -0.71%

Traditional ROI: 2.49%

Winchester , KY

3 beds | 2 baths | 2,250 sq.ft.

$279,500

Airbnb cash on cash: 1.72%

Traditional cash on cash: 6%

Airbnb Rental Income: $1466

Traditional Rental Income: $2162

Airbnb ROI: 1.72%

Traditional ROI: 6%

Winchester , KY

12 beds | 4 baths | 4,010 sq.ft.

$290,000

Airbnb cash on cash: N/A

Traditional cash on cash: 11.48%

Airbnb Rental Income: $null

Traditional Rental Income: $3514

Airbnb ROI: N/A

Traditional ROI: 11.48%

Winchester , KY

3 beds | 2 baths | 2,636 sq.ft.

$379,717

Airbnb cash on cash: 0.79%

Traditional cash on cash: 3.27%

Airbnb Rental Income: $1466

Traditional Rental Income: $1919

Airbnb ROI: 0.79%

Traditional ROI: 3.27%

Winchester , KY

4 beds | 3 baths | 1,776 sq.ft.

$325,000

Airbnb cash on cash: 1.1%

Traditional cash on cash: 4.68%

Airbnb Rental Income: $1423

Traditional Rental Income: $2088

Airbnb ROI: 1.1%

Traditional ROI: 4.68%

Winchester , KY

3 beds | 2 baths | 1,352 sq.ft.

$274,900