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: 1.58% Traditional cash on cash: 5.57% Airbnb Rental Income: $1077 Traditional Rental Income: $1520 Airbnb ROI: 1.58% Traditional ROI: 5.57%
356 Colby Ridge Boulevard Winchester, KY This cozy 2-bedroom, 1.5-bath home is the perfect fit for first-time buyers or anyone look...	2 beds \| 2 baths \| 1,102 sq.ft.	$184,000	Airbnb cash on cash: 1.66% Traditional cash on cash: 6% Airbnb Rental Income: $1077 Traditional Rental Income: $1467 Airbnb ROI: 1.66% Traditional ROI: 6%
403 Country Club Drive Winchester, KY Charming and recently updated, this 1.5-story townhome is located in the Spencer Community...	2 beds \| 2 baths \| 1,122 sq.ft.	$174,900	Airbnb cash on cash: 1.85% Traditional cash on cash: 6.64% Airbnb Rental Income: $1077 Traditional Rental Income: $1507 Airbnb ROI: 1.85% Traditional ROI: 6.64%
Other Investment Properties for Sale in Winchester
120 Windsor Drive Winchester , KY Welcome home to this cozy brick charmer in the desirable Belair Subdivision of Winchester,...	4 beds \| 1 baths \| 1,610 sq.ft.	$259,900	Airbnb cash on cash: 2.43% Traditional cash on cash: 4.24% Airbnb Rental Income: $1600 Traditional Rental Income: $1588 Airbnb ROI: 2.43% Traditional ROI: 4.24%
221 Moundale Avenue Winchester , KY Step back in time as you walk up the stone steps into this beautiful 3 bed 2.5 bath house....	3 beds \| 3 baths \| 2,628 sq.ft.	$345,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.01% Airbnb Rental Income: $null Traditional Rental Income: $2964 Airbnb ROI: N/A Traditional ROI: 7.01%
118 Windridge Drive Winchester , KY Enjoy rest, relaxation and all the outdoor activities you can dream up with this home. Coz...	3 beds \| 2 baths \| 1,617 sq.ft.	$307,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.14% Airbnb Rental Income: $null Traditional Rental Income: $1829 Airbnb ROI: N/A Traditional ROI: 4.14%
618 Westmeade Drive Winchester , KY Conveniently located, this charming well kept home features a functional floorplan offerin...	4 beds \| 2 baths \| 2,116 sq.ft.	$296,900	Airbnb cash on cash: 1.91% Traditional cash on cash: 6.04% Airbnb Rental Income: $1600 Traditional Rental Income: $2301 Airbnb ROI: 1.91% Traditional ROI: 6.04%
720 Terry Drive Winchester , KY Welcome home to this beautifully refreshed 3-bedroom, 2-bath property located in the heart...	3 beds \| 2 baths \| 1,779 sq.ft.	$275,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.63% Airbnb Rental Income: $null Traditional Rental Income: $2033 Airbnb ROI: N/A Traditional ROI: 5.63%
168 Buckingham Lane Winchester , KY Tucked away on a quiet cul-de-sac, this well-maintained 4-bedroom, 2.5-bath home offers th...	4 beds \| 3 baths \| 2,358 sq.ft.	$339,900	Airbnb cash on cash: 1.44% Traditional cash on cash: 6.63% Airbnb Rental Income: $1600 Traditional Rental Income: $2804 Airbnb ROI: 1.44% Traditional ROI: 6.63%
363 S Main Street Winchester , KY Back on Market! Welcome to 363 South Main Street in the heart of downtown Winchester, KY-t...	3 beds \| 2 baths \| 2,142 sq.ft.	$250,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.08% Airbnb Rental Income: $null Traditional Rental Income: $2201 Airbnb ROI: N/A Traditional ROI: 7.08%
128 Bay Hill Drive Winchester , KY Opportunity knocks in Royal Oaks Village-be part of Winchester's next chapter. Located wit...	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%
29 Euclid Avenue Winchester , KY Welcome to 29 Euclid Ave in the heart of downtown Winchester! This charming home features ...	3 beds \| 2 baths \| 1,498 sq.ft.	$190,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.95% Airbnb Rental Income: $null Traditional Rental Income: $1722 Airbnb ROI: N/A Traditional ROI: 7.95%
59 Holiday Road Winchester , KY Don't Wait - this home is priced to Sell! All one level brick ranch features 3 Bedrooms, 1...	3 beds \| 1 baths \| 1,050 sq.ft.	$209,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.29% Airbnb Rental Income: $null Traditional Rental Income: $1258 Airbnb ROI: N/A Traditional ROI: 4.29%
34 Hays Street Winchester , KY This spacious 4-bedroom bungalow is tucked away in downtown Winchester in a great walkable...	4 beds \| 2 baths \| 2,450 sq.ft.	$210,000	Airbnb cash on cash: 3.98% Traditional cash on cash: 9.81% Airbnb Rental Income: $1600 Traditional Rental Income: $2304 Airbnb ROI: 3.98% Traditional ROI: 9.81%
310 Essex Court Winchester , KY Welcome home to this charming and spacious 2-bedroom, 2.5-bath townhome perfectly situated...	2 beds \| 3 baths \| 1,188 sq.ft.	$192,500	Airbnb cash on cash: 2.29% Traditional cash on cash: 7.13% Airbnb Rental Income: $1077 Traditional Rental Income: $1594 Airbnb ROI: 2.29% Traditional ROI: 7.13%
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.	$179,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.55% Airbnb Rental Income: $null Traditional Rental Income: $1387 Airbnb ROI: N/A Traditional ROI: 6.55%
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%
28 Churchill Drive Winchester , KY Beautifully updated ranch on a new, fully finished walk out basement. 5 bedrooms, 2 being ...	5 beds \| 3 baths \| 2,624 sq.ft.	$330,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.41% Airbnb Rental Income: $null Traditional Rental Income: $2657 Airbnb ROI: N/A Traditional ROI: 6.41%

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: 1.58%

Traditional cash on cash: 5.57%

Airbnb Rental Income: $1077

Traditional Rental Income: $1520

Airbnb ROI: 1.58%

Traditional ROI: 5.57%

356 Colby Ridge Boulevard

Winchester, KY

2 beds | 2 baths | 1,102 sq.ft.

$184,000

Airbnb cash on cash: 1.66%

Traditional cash on cash: 6%

Airbnb Rental Income: $1077

Traditional Rental Income: $1467

Airbnb ROI: 1.66%

Traditional ROI: 6%

403 Country Club Drive

Winchester, KY

2 beds | 2 baths | 1,122 sq.ft.

$174,900

Airbnb cash on cash: 1.85%

Traditional cash on cash: 6.64%

Airbnb Rental Income: $1077

Traditional Rental Income: $1507

Airbnb ROI: 1.85%

Traditional ROI: 6.64%

Other Investment Properties for Sale in Winchester

Winchester , KY

4 beds | 1 baths | 1,610 sq.ft.

$259,900

Airbnb cash on cash: 2.43%

Traditional cash on cash: 4.24%

Airbnb Rental Income: $1600

Traditional Rental Income: $1588

Airbnb ROI: 2.43%

Traditional ROI: 4.24%

Winchester , KY

3 beds | 3 baths | 2,628 sq.ft.

$345,000

Airbnb cash on cash: N/A

Traditional cash on cash: 7.01%

Airbnb Rental Income: $null

Traditional Rental Income: $2964

Airbnb ROI: N/A

Traditional ROI: 7.01%

Winchester , KY

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

$307,900

Airbnb cash on cash: N/A

Traditional cash on cash: 4.14%

Airbnb Rental Income: $null

Traditional Rental Income: $1829

Airbnb ROI: N/A

Traditional ROI: 4.14%

Winchester , KY

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

$296,900

Airbnb cash on cash: 1.91%

Traditional cash on cash: 6.04%

Airbnb Rental Income: $1600

Traditional Rental Income: $2301

Airbnb ROI: 1.91%

Traditional ROI: 6.04%

Winchester , KY

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

$275,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.63%

Airbnb Rental Income: $null

Traditional Rental Income: $2033

Airbnb ROI: N/A

Traditional ROI: 5.63%

Winchester , KY

4 beds | 3 baths | 2,358 sq.ft.

$339,900