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.	$195,500	Airbnb cash on cash: -0.33% Traditional cash on cash: 6.69% Airbnb Rental Income: $590 Traditional Rental Income: $1606 Airbnb ROI: -0.33% Traditional ROI: 6.69%
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.	$197,500	Airbnb cash on cash: -0.33% Traditional cash on cash: 6.62% Airbnb Rental Income: $590 Traditional Rental Income: $1606 Airbnb ROI: -0.33% Traditional ROI: 6.62%
Other Investment Properties for Sale in Winchester
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%
410 Corinne Court Winchester , KY Charming Ranch-Style Home with Lots of Room- Step inside this 8 year old beautiful 1,604 s...	3 beds \| 2 baths \| 1,604 sq.ft.	$319,000	Airbnb cash on cash: 1.28% Traditional cash on cash: 4.31% Airbnb Rental Income: $1466 Traditional Rental Income: $1942 Airbnb ROI: 1.28% Traditional ROI: 4.31%
118 Windridge Drive Winchester , KY Start off the new year in a new home! Imagine spending summers in your own private backyar...	3 beds \| 2 baths \| 1,617 sq.ft.	$318,000	Airbnb cash on cash: 1.29% Traditional cash on cash: 3.95% Airbnb Rental Income: $1466 Traditional Rental Income: $1829 Airbnb ROI: 1.29% Traditional ROI: 3.95%
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.	$330,000	Airbnb cash on cash: 1.06% Traditional cash on cash: 4.58% Airbnb Rental Income: $1423 Traditional Rental Income: $2088 Airbnb ROI: 1.06% Traditional ROI: 4.58%
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.	$175,000	Airbnb cash on cash: 4.59% Traditional cash on cash: 6.71% Airbnb Rental Income: $1466 Traditional Rental Income: $1387 Airbnb ROI: 4.59% Traditional ROI: 6.71%
42 Mockingbird Valley Road Winchester , KY The term 'Move In Ready' really and truly applies here at 42 Mockingbird Valley Road! Vers...	3 beds \| 2 baths \| 2,961 sq.ft.	$457,900	Airbnb cash on cash: 0.34% Traditional cash on cash: 3.5% Airbnb Rental Income: $1466 Traditional Rental Income: $2386 Airbnb ROI: 0.34% Traditional ROI: 3.5%
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.	$115,000	Airbnb cash on cash: 0.04% Traditional cash on cash: 8.58% Airbnb Rental Income: $590 Traditional Rental Income: $1251 Airbnb ROI: 0.04% Traditional ROI: 8.58%
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.	$182,000	Airbnb cash on cash: 3.58% Traditional cash on cash: 7.66% Airbnb Rental Income: $1466 Traditional Rental Income: $1740 Airbnb ROI: 3.58% Traditional ROI: 7.66%
408 Corinne Court Winchester , KY Come see this immaculate 3 bedroom, 2 bath single-story ranch with an open-concept split b...	3 beds \| 2 baths \| 1,604 sq.ft.	$394,999	Airbnb cash on cash: 1.49% Traditional cash on cash: 3.79% Airbnb Rental Income: $1466 Traditional Rental Income: $1883 Airbnb ROI: 1.49% Traditional ROI: 3.79%
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%
165 Hilltop Drive Winchester , KY *Priced Below Recent Apraised Value* This stunning property is ideally located and is ...	3 beds \| 2 baths \| 1,454 sq.ft.	$274,900	Airbnb cash on cash: 2.58% Traditional cash on cash: 5.76% Airbnb Rental Income: $1466 Traditional Rental Income: $1856 Airbnb ROI: 2.58% Traditional ROI: 5.76%
125 Summerhill Way Winchester , KY Welcome home to this darling farmhouse-style gem on a quiet street in Winchester! You'll l...	3 beds \| 2 baths \| 1,333 sq.ft.	$259,900	Airbnb cash on cash: 2.35% Traditional cash on cash: 5.69% Airbnb Rental Income: $1466 Traditional Rental Income: $1852 Airbnb ROI: 2.35% Traditional ROI: 5.69%
417 Mt Vernon Drive Winchester , KY A 3 bedroom 2 bath home with a 2 car garage under 150k? Unbelievable! Start off your new y...	3 beds \| 2 baths \| 1,300 sq.ft.	$145,000	Airbnb cash on cash: 4.11% Traditional cash on cash: 7.71% Airbnb Rental Income: $1466 Traditional Rental Income: $1532 Airbnb ROI: 4.11% Traditional ROI: 7.71%

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.

$195,500

Airbnb cash on cash: -0.33%

Traditional cash on cash: 6.69%

Airbnb Rental Income: $590

Traditional Rental Income: $1606

Airbnb ROI: -0.33%

Traditional ROI: 6.69%

111 Quail Ridge Road

Winchester, KY

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

$197,500

Airbnb cash on cash: -0.33%

Traditional cash on cash: 6.62%

Airbnb Rental Income: $590

Traditional Rental Income: $1606

Airbnb ROI: -0.33%

Traditional ROI: 6.62%

Other Investment Properties for Sale in Winchester

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

3 beds | 2 baths | 1,604 sq.ft.

$319,000

Airbnb cash on cash: 1.28%

Traditional cash on cash: 4.31%

Airbnb Rental Income: $1466

Traditional Rental Income: $1942

Airbnb ROI: 1.28%

Traditional ROI: 4.31%

Winchester , KY

3 beds | 2 baths | 1,617 sq.ft.

$318,000

Airbnb cash on cash: 1.29%

Traditional cash on cash: 3.95%

Airbnb Rental Income: $1466

Traditional Rental Income: $1829

Airbnb ROI: 1.29%

Traditional ROI: 3.95%

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.

$330,000

Airbnb cash on cash: 1.06%

Traditional cash on cash: 4.58%

Airbnb Rental Income: $1423

Traditional Rental Income: $2088

Airbnb ROI: 1.06%

Traditional ROI: 4.58%

Winchester , KY

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

$274,900