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.

Investment Property for Sale in Winchester, KY

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
14 Trailwoods Dr Winchester, KY Looking for an affordable home at Nolin Lake? Look no further! This home is ready for new ...	3 beds \| 2 baths \| 1,360 sq.ft.	$210,000	Airbnb cash on cash: 2.95% Traditional cash on cash: 6.05% Airbnb Rental Income: $1466 Traditional Rental Income: $1651 Airbnb ROI: 2.95% Traditional ROI: 6.05%
Investment Properties for Sale in Other Cities of Kentucky
133 Wallace Avenue Frankfort , KY Wonderful, well-kept home, located in downtown Frankfort. A two bedroom and one bathroom h...	2 beds \| 1 baths \| 1,024 sq.ft.	$127,000	Airbnb cash on cash: 5.55% Traditional cash on cash: 7.5% Airbnb Rental Income: $1424 Traditional Rental Income: $1236 Airbnb ROI: 5.55% Traditional ROI: 7.5%
609 Moore Drive Elizabethtown , KY This well-kept 3-bedroom, 1-bath home is move-in ready and full of charm! Built in 2003, i...	3 beds \| 1 baths \| 1,170 sq.ft.	$189,900	Airbnb cash on cash: 1.69% Traditional cash on cash: 5.51% Airbnb Rental Income: $1106 Traditional Rental Income: $1422 Airbnb ROI: 1.69% Traditional ROI: 5.51%
303 Ingram Avenue CAMPBELLSVILLE , KY Spacious 4-Bedroom Home in Prime Location Near Schools & Amenities Welcome to this charmin...	4 beds \| 3 baths \| 1,784 sq.ft.	$225,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.69% Airbnb Rental Income: $null Traditional Rental Income: $2124 Airbnb ROI: N/A Traditional ROI: 7.69%
1971 Highway 1385 HARDINSBURG , KY New Listing in Beautiful Hardinsburg, Kentucky! Enjoy country living at its best with this...	3 beds \| 4 baths \| 1,609 sq.ft.	$312,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.47% Airbnb Rental Income: $null Traditional Rental Income: $1949 Airbnb ROI: N/A Traditional ROI: 4.47%
857 Malabu Drive unit: 1202 #1202 Lexington , KY Great Opportunity to own an adorable 2 bedroom, 2 full bathroom condominium. This lovely c...	2 beds \| 2 baths \| 1,100 sq.ft.	$225,000	Airbnb cash on cash: 3.29% Traditional cash on cash: 5.06% Airbnb Rental Income: $2050 Traditional Rental Income: $1898 Airbnb ROI: 3.29% Traditional ROI: 5.06%
39 Bryants Way London , KY This home is located in one of Londons desired neighborhoods.The home features 4 bedrooms,...	4 beds \| 3 baths \| 2,061 sq.ft.	$336,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.29% Airbnb Rental Income: $null Traditional Rental Income: $2351 Airbnb ROI: N/A Traditional ROI: 5.29%
173 Natures Way CAMPBELLSVILLE , KY Welcome to this charming 3 bedroom, 1 bath single-family home nestled in the desirable Nat...	3 beds \| 1 baths \| 1,288 sq.ft.	$190,000	Airbnb cash on cash: 0.34% Traditional cash on cash: 5.94% Airbnb Rental Income: $812 Traditional Rental Income: $1500 Airbnb ROI: 0.34% Traditional ROI: 5.94%
309 E Market St unit: 213 #213 Louisville , KY Escape into your private oasis, in the middle of downtown Louisville, at the Mercantile Ga...	2 beds \| 2 baths \| 1,402 sq.ft.	$343,000	Airbnb cash on cash: -1.33% Traditional cash on cash: 2.42% Airbnb Rental Income: $1264 Traditional Rental Income: $2070 Airbnb ROI: -1.33% Traditional ROI: 2.42%
167 N Keats Ave Louisville , KY A fully turn-key Clifton treasure, this beautifully updated home blends classic charm with...	2 beds \| 2 baths \| 989 sq.ft.	$344,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.32% Airbnb Rental Income: $null Traditional Rental Income: $1120 Airbnb ROI: N/A Traditional ROI: 1.32%
1234 Hull St Louisville , KY Welcome to 1234 Hull Street - an irresistibly charming Highlands home that blends vintage ...	3 beds \| 1 baths \| 1,218 sq.ft.	$250,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.12% Airbnb Rental Income: $null Traditional Rental Income: $1504 Airbnb ROI: N/A Traditional ROI: 4.12%
306 S Hite Ave Louisville , KY Talk about curb appeal! Tucked just off Frankfort Ave, this Crescent Hill gem sits on a ra...	2 beds \| 1 baths \| 1,300 sq.ft.	$385,000	Airbnb cash on cash: -0.06% Traditional cash on cash: 1.93% Airbnb Rental Income: $1115 Traditional Rental Income: $1461 Airbnb ROI: -0.06% Traditional ROI: 1.93%
1368 Poplar Level Rd Louisville , KY Charming 2-bedroom, 1-bath home featuring an updated kitchen with modern appliances and pl...	2 beds \| 1 baths \| 820 sq.ft.	$225,000	Airbnb cash on cash: 1.57% Traditional cash on cash: 3.73% Airbnb Rental Income: $1212 Traditional Rental Income: $1282 Airbnb ROI: 1.57% Traditional ROI: 3.73%
7797 Promontory Drive Alexandria , KY Incredible Fischer Clay loaded with upgrades! This beautiful multi-level floorplan offers ...	4 beds \| 2 baths \| 3,029 sq.ft.	$610,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.86% Airbnb Rental Income: $null Traditional Rental Income: $2254 Airbnb ROI: N/A Traditional ROI: 1.86%
1627 Haskin Ave Louisville , KY Move-in ready and fully renovated, this 4-bedroom, 1-bath home blends modern updates with ...	4 beds \| 1 baths \| 1,500 sq.ft.	$227,500	Airbnb cash on cash: 2.49% Traditional cash on cash: 4.89% Airbnb Rental Income: $1461 Traditional Rental Income: $1545 Airbnb ROI: 2.49% Traditional ROI: 4.89%
2066 S Shelby St Louisville , KY This gorgeous 3-bedroom, 2-bathroom home blends classic character with many thoughtful upd...	3 beds \| 2 baths \| 1,700 sq.ft.	$301,250	Airbnb cash on cash: 0.52% Traditional cash on cash: 4.91% Airbnb Rental Income: $1147 Traditional Rental Income: $2011 Airbnb ROI: 0.52% Traditional ROI: 4.91%

Real Estate investment in Winchester, KY

There are 2 properties for sale in the city of Winchester . The median list price in Winchester is $330,000 and the average price per square foot is $126. In December 2025, the average monthly cash on cash return in Winchester is 5.00%. The average monthly rental income in Winchester is $1,981.

Winchester, KY Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 2 investment properties available for sale in Winchester.

In 2025, the best neighborhood to buy investment property is Winchester.

The ROI for Long-Term is higher than the Short-Term in Winchester with average rental income of $1,981.

Your search for investment property begins and ends here

Investment Property for Sale in Winchester, KY

14 Trailwoods Dr

Winchester, KY

3 beds | 2 baths | 1,360 sq.ft.

$210,000

Airbnb cash on cash: 2.95%

Traditional cash on cash: 6.05%

Airbnb Rental Income: $1466

Traditional Rental Income: $1651

Airbnb ROI: 2.95%

Traditional ROI: 6.05%

Investment Properties for Sale in Other Cities of Kentucky

Frankfort , KY

2 beds | 1 baths | 1,024 sq.ft.

$127,000

Airbnb cash on cash: 5.55%

Traditional cash on cash: 7.5%

Airbnb Rental Income: $1424

Traditional Rental Income: $1236

Airbnb ROI: 5.55%

Traditional ROI: 7.5%

Elizabethtown , KY

3 beds | 1 baths | 1,170 sq.ft.

$189,900

Airbnb cash on cash: 1.69%

Traditional cash on cash: 5.51%

Airbnb Rental Income: $1106

Traditional Rental Income: $1422

Airbnb ROI: 1.69%

Traditional ROI: 5.51%

CAMPBELLSVILLE , KY

4 beds | 3 baths | 1,784 sq.ft.

$225,000

Airbnb cash on cash: N/A

Traditional cash on cash: 7.69%

Airbnb Rental Income: $null

Traditional Rental Income: $2124

Airbnb ROI: N/A

Traditional ROI: 7.69%

HARDINSBURG , KY

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

$312,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.47%

Airbnb Rental Income: $null

Traditional Rental Income: $1949

Airbnb ROI: N/A

Traditional ROI: 4.47%

Lexington , KY

2 beds | 2 baths | 1,100 sq.ft.

$225,000

Airbnb cash on cash: 3.29%

Traditional cash on cash: 5.06%

Airbnb Rental Income: $2050

Traditional Rental Income: $1898

Airbnb ROI: 3.29%

Traditional ROI: 5.06%

London , KY

4 beds | 3 baths | 2,061 sq.ft.

$336,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.29%

Airbnb Rental Income: $null

Traditional Rental Income: $2351

Airbnb ROI: N/A

Traditional ROI: 5.29%

CAMPBELLSVILLE , KY

3 beds | 1 baths | 1,288 sq.ft.

$190,000

Airbnb cash on cash: 0.34%

Traditional cash on cash: 5.94%

Airbnb Rental Income: $812

Traditional Rental Income: $1500

Airbnb ROI: 0.34%

Traditional ROI: 5.94%

Louisville , KY

2 beds | 2 baths | 1,402 sq.ft.

$343,000

Airbnb cash on cash: -1.33%

Traditional cash on cash: 2.42%