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
133 Bay Hill Drive Winchester, KY Welcome to 133 Bay Hill Drive in Winchester, Kentucky - a spacious and beautifully maintai...	4 beds \| 4 baths \| 3,276 sq.ft.	$280,000	Airbnb cash on cash: 1.47% Traditional cash on cash: 6.79% Airbnb Rental Income: $1408 Traditional Rental Income: $2389 Airbnb ROI: 1.47% Traditional ROI: 6.79%
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: 1.74% Traditional cash on cash: 5.57% Airbnb Rental Income: $1116 Traditional Rental Income: $1520 Airbnb ROI: 1.74% Traditional ROI: 5.57%
104 Bay Hill Drive Winchester, KY You don't want to miss this desirable two primary bedroom home with 2 full bathrooms and l...	2 beds \| 2 baths \| 1,200 sq.ft.	$199,000	Airbnb cash on cash: 1.97% Traditional cash on cash: 6.37% Airbnb Rental Income: $1116 Traditional Rental Income: $1573 Airbnb ROI: 1.97% Traditional ROI: 6.37%
Other Investment Properties for Sale in Winchester
339 S Main Street Winchester , KY Beautiful move-in ready Cape Cod home on the edge of historic downtown Winchester! This ho...	4 beds \| 2 baths \| 1,848 sq.ft.	$219,900	Airbnb cash on cash: 2.43% Traditional cash on cash: 8.05% Airbnb Rental Income: $1408 Traditional Rental Income: $2156 Airbnb ROI: 2.43% Traditional ROI: 8.05%
120 Windsor Drive Winchester , KY Nestled in a well-established neighborhood filled with charm and character, this inviting ...	4 beds \| 1 baths \| 1,609 sq.ft.	$235,000	Airbnb cash on cash: 2.16% Traditional cash on cash: 4.88% Airbnb Rental Income: $1408 Traditional Rental Income: $1588 Airbnb ROI: 2.16% Traditional ROI: 4.88%
618 Westmeade Drive Winchester , KY Conveniently located, this charming well kept home features a functional floor plan offeri...	4 beds \| 2 baths \| 2,116 sq.ft.	$284,900	Airbnb cash on cash: 1.47% Traditional cash on cash: 6.37% Airbnb Rental Income: $1408 Traditional Rental Income: $2301 Airbnb ROI: 1.47% Traditional ROI: 6.37%
720 Terry Drive Winchester , KY Welcome home to this cozy 3-bedroom, 2-bath property located in the heart of Winchester, K...	3 beds \| 2 baths \| 1,779 sq.ft.	$270,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.76% Airbnb Rental Income: $null Traditional Rental Income: $2033 Airbnb ROI: N/A Traditional ROI: 5.76%
216 Robyn Drive Winchester , KY Meticulously maintained 3-bedroom, 2-bath home on a full basement with wonderful curb appe...	3 beds \| 2 baths \| 1,988 sq.ft.	$245,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.29% Airbnb Rental Income: $null Traditional Rental Income: $2211 Airbnb ROI: N/A Traditional ROI: 7.29%
411 Skylark Drive Winchester , KY Professional Pictures coming 7/11. Welcome home to this spacious corner-lot property in a ...	4 beds \| 3 baths \| 2,591 sq.ft.	$350,000	Airbnb cash on cash: 0.86% Traditional cash on cash: 5.46% Airbnb Rental Income: $1408 Traditional Rental Income: $2496 Airbnb ROI: 0.86% Traditional ROI: 5.46%
128 Bay Hill Drive Winchester , KY Opportunity knocks in Royal Oaks Village--be part of Winchester's next chapter. Located wi...	3 beds \| 2 baths \| 1,289 sq.ft.	$200,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.08% Airbnb Rental Income: $null Traditional Rental Income: $1613 Airbnb ROI: N/A Traditional ROI: 6.08%
411 Boone Avenue Winchester , KY Gracious, comfortable Cape Cod on a beautiful double lot directly across from the Winchest...	4 beds \| 3 baths \| 3,405 sq.ft.	$349,000	Airbnb cash on cash: 0.87% Traditional cash on cash: 6.66% Airbnb Rental Income: $1408 Traditional Rental Income: $2884 Airbnb ROI: 0.87% Traditional ROI: 6.66%
20 Edgewood Drive Winchester , KY Welcome to this beautiful brick ranch on a basement in Hampton Manor. The double front doo...	3 beds \| 3 baths \| 2,289 sq.ft.	$427,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.56% Airbnb Rental Income: $null Traditional Rental Income: $1857 Airbnb ROI: N/A Traditional ROI: 2.56%
119 Sunset Heights Winchester , KY Come Home to Sunset!!!! Brick Ranch home, with 2 driveways, 3 bedrooms, 1 bathroom, Open L...	3 beds \| 1 baths \| 1,324 sq.ft.	$265,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.32% Airbnb Rental Income: $null Traditional Rental Income: $1518 Airbnb ROI: N/A Traditional ROI: 4.32%
5977 Mount Sterling Road Winchester , KY Welcome home to this charming 3 bedroom, 2 bath property situated on a beautiful 1.45 acre...	3 beds \| 2 baths \| 1,450 sq.ft.	$245,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.91% Airbnb Rental Income: $null Traditional Rental Income: $1757 Airbnb ROI: N/A Traditional ROI: 5.91%
19 Fontaine Boulevard Winchester , KY Charming story and a half home nestled in a well established neighborhood, featuring beaut...	3 beds \| 3 baths \| 2,235 sq.ft.	$399,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.07% Airbnb Rental Income: $null Traditional Rental Income: $2308 Airbnb ROI: N/A Traditional ROI: 4.07%
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.	$169,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.98% Airbnb Rental Income: $null Traditional Rental Income: $1387 Airbnb ROI: N/A Traditional ROI: 6.98%
42 Mockingbird Valley Road Winchester , KY This is a perfect home for EVERY season.....enjoy multiple, interior gathering spaces and ...	3 beds \| 3 baths \| 2,961 sq.ft.	$445,500	Airbnb cash on cash: N/A Traditional cash on cash: 3.64% Airbnb Rental Income: $null Traditional Rental Income: $2386 Airbnb ROI: N/A Traditional ROI: 3.64%
327 Newcastle Lane Winchester , KY PRICE REDUCTION!!! Perfect for investment or primary residence. Welcome home to this cozy ...	4 beds \| 3 baths \| 1,693 sq.ft.	$284,900	Airbnb cash on cash: 2.25% Traditional cash on cash: 5.61% Airbnb Rental Income: $1408 Traditional Rental Income: $1887 Airbnb ROI: 2.25% Traditional ROI: 5.61%

Your search for investment property begins and ends here

Townhouses for Sale in Winchester, KY

133 Bay Hill Drive

Winchester, KY

4 beds | 4 baths | 3,276 sq.ft.

$280,000

Airbnb cash on cash: 1.47%

Traditional cash on cash: 6.79%

Airbnb Rental Income: $1408

Traditional Rental Income: $2389

Airbnb ROI: 1.47%

Traditional ROI: 6.79%

271 April Way

Winchester, KY

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

$215,000

Airbnb cash on cash: 1.74%

Traditional cash on cash: 5.57%

Airbnb Rental Income: $1116

Traditional Rental Income: $1520

Airbnb ROI: 1.74%

Traditional ROI: 5.57%

104 Bay Hill Drive

Winchester, KY

2 beds | 2 baths | 1,200 sq.ft.

$199,000

Airbnb cash on cash: 1.97%

Traditional cash on cash: 6.37%

Airbnb Rental Income: $1116

Traditional Rental Income: $1573

Airbnb ROI: 1.97%

Traditional ROI: 6.37%

Other Investment Properties for Sale in Winchester

Winchester , KY

4 beds | 2 baths | 1,848 sq.ft.

$219,900

Airbnb cash on cash: 2.43%

Traditional cash on cash: 8.05%

Airbnb Rental Income: $1408

Traditional Rental Income: $2156

Airbnb ROI: 2.43%

Traditional ROI: 8.05%

Winchester , KY

4 beds | 1 baths | 1,609 sq.ft.

$235,000

Airbnb cash on cash: 2.16%

Traditional cash on cash: 4.88%

Airbnb Rental Income: $1408

Traditional Rental Income: $1588

Airbnb ROI: 2.16%

Traditional ROI: 4.88%

Winchester , KY

4 beds | 2 baths | 2,116 sq.ft.

$284,900

Airbnb cash on cash: 1.47%

Traditional cash on cash: 6.37%

Airbnb Rental Income: $1408

Traditional Rental Income: $2301

Airbnb ROI: 1.47%

Traditional ROI: 6.37%

Winchester , KY

3 beds | 2 baths | 1,779 sq.ft.

$270,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.76%

Airbnb Rental Income: $null

Traditional Rental Income: $2033

Airbnb ROI: N/A

Traditional ROI: 5.76%

Winchester , KY

3 beds | 2 baths | 1,988 sq.ft.

$245,000

Airbnb cash on cash: N/A

Traditional cash on cash: 7.29%

Airbnb Rental Income: $null

Traditional Rental Income: $2211

Airbnb ROI: N/A

Traditional ROI: 7.29%

Winchester , KY

4 beds | 3 baths | 2,591 sq.ft.

$350,000