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
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%
178 Hawthorne Drive Winchester, KY Welcome to your Kentucky haven. This charming 3 bedroom, 2.5 bath home has a covered front...	3 beds \| 3 baths \| 2,156 sq.ft.	$390,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.12% Airbnb Rental Income: $null Traditional Rental Income: $2336 Airbnb ROI: N/A Traditional ROI: 5.12%
122 Spruce Court Winchester, KY Don't miss this move-in ready brick ranch home offering the perfect blend of comfort, styl...	3 beds \| 2 baths \| 1,210 sq.ft.	$228,500	Airbnb cash on cash: N/A Traditional cash on cash: 5% Airbnb Rental Income: $null Traditional Rental Income: $1574 Airbnb ROI: N/A Traditional ROI: 5%
125 Kittison Drive Winchester, KY Charming ranch home featuring 3 bedrooms, 1 full bath with a spacious layout and inviting ...	3 beds \| 1 baths \| 1,100 sq.ft.	$235,500	Airbnb cash on cash: N/A Traditional cash on cash: 4.5% Airbnb Rental Income: $null Traditional Rental Income: $1336 Airbnb ROI: N/A Traditional ROI: 4.5%
13 Lakeview Drive Winchester, KY Beautifully updated brick ranch with a partially finished basement offering 3 bedrooms and...	3 beds \| 2 baths \| 1,932 sq.ft.	$315,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.89% Airbnb Rental Income: $null Traditional Rental Income: $1498 Airbnb ROI: N/A Traditional ROI: 2.89%
54 Locust Drive Winchester, KY Opportunity awaits at 54 Locust Drive in Wesleyan Park subdivision. This all-brick ranch o...	3 beds \| 2 baths \| 1,692 sq.ft.	$289,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.63% Airbnb Rental Income: $null Traditional Rental Income: $1859 Airbnb ROI: N/A Traditional ROI: 4.63%
6888 Bybee Road Winchester, KY Welcome to your private slice of Kentucky countryside - offering the perfect blend of mode...	1 beds \| 1 baths \| 800 sq.ft.	$350,000	Airbnb cash on cash: -0.46% Traditional cash on cash: 2.91% Airbnb Rental Income: $693 Traditional Rental Income: $1497 Airbnb ROI: -0.46% Traditional ROI: 2.91%
405 Tremont Lane Winchester, KY Welcome to this beautifully maintained 4 bedroom, 2.5 bathroom home over 2,200 square feet...	4 beds \| 3 baths \| 2,274 sq.ft.	$349,000	Airbnb cash on cash: 0.87% Traditional cash on cash: 4.67% Airbnb Rental Income: $1408 Traditional Rental Income: $2231 Airbnb ROI: 0.87% Traditional ROI: 4.67%
119 Gibson Way Winchester, KY Updated Price, below Apprisal value...Space, Location, and Great Finishes....4 bedrooms, 2...	4 beds \| 3 baths \| 2,325 sq.ft.	$349,900	Airbnb cash on cash: 1.54% Traditional cash on cash: 5.9% Airbnb Rental Income: $1408 Traditional Rental Income: $2418 Airbnb ROI: 1.54% Traditional ROI: 5.9%
110 Powe Drive Winchester, KY This 4 Bedroom, 3 Bath home is quietly nestled within the Greenfield subdivision. Prime lo...	4 beds \| 3 baths \| 2,010 sq.ft.	$329,900	Airbnb cash on cash: 1.8% Traditional cash on cash: 5.71% Airbnb Rental Income: $1408 Traditional Rental Income: $2198 Airbnb ROI: 1.8% Traditional ROI: 5.71%
502 W Lexington Avenue Winchester, KY Investment opportunity in the heart of Winchester! Brick Triplex featuring a main level, h...	4 beds \| 4 baths \| 4,798 sq.ft.	$350,000	Airbnb cash on cash: 0.86% Traditional cash on cash: 11.38% Airbnb Rental Income: $1408 Traditional Rental Income: $4444 Airbnb ROI: 0.86% Traditional ROI: 11.38%
209 Boone Avenue Winchester, KY Space, updates, and charm all come together in this spacious 2,260 square foot 1.5-story h...	3 beds \| 3 baths \| 2,260 sq.ft.	$290,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.86% Airbnb Rental Income: $null Traditional Rental Income: $2473 Airbnb ROI: N/A Traditional ROI: 6.86%
107 Gibson Way Winchester, KY A beautiful designed spacious house that offers 3 bedrooms, 3 full bathrooms, and 2266 sq ...	3 beds \| 3 baths \| 2,266 sq.ft.	$345,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.05% Airbnb Rental Income: $null Traditional Rental Income: $2329 Airbnb ROI: N/A Traditional ROI: 5.05%
30 Virginia Avenue Winchester, KY Welcome to a well maintained 3 bedroom 1 full bath home that has been lovingly cared for b...	3 beds \| 1 baths \| 1,050 sq.ft.	$239,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.6% Airbnb Rental Income: $null Traditional Rental Income: $1324 Airbnb ROI: N/A Traditional ROI: 3.6%
4603 Paris Road Winchester, KY Professional photos coming soon! Over 3300 sq ft w tons of character situated on an acre o...	5 beds \| 3 baths \| 3,314 sq.ft.	$299,900	Airbnb cash on cash: N/A Traditional cash on cash: 8.1% Airbnb Rental Income: $null Traditional Rental Income: $2903 Airbnb ROI: N/A Traditional ROI: 8.1%
265 S Highland Street Winchester, KY Great investment opportunity in downtown Winchester! This spacious quadplex has been updat...	8 beds \| 4 baths \| 5,058 sq.ft.	$479,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.59% Airbnb Rental Income: $null Traditional Rental Income: $3505 Airbnb ROI: N/A Traditional ROI: 6.59%
1480 Irvine Road Winchester, KY Beautifully remodeled farmhouse on 10 fenced acres! This 3 bedroom, 3.5 bath home with a f...	3 beds \| 4 baths \| 3,388 sq.ft.	$649,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.47% Airbnb Rental Income: $null Traditional Rental Income: $3588 Airbnb ROI: N/A Traditional ROI: 4.47%
414 Pueblo Court Winchester, KY PRICE DROP and a MOTIVATED SELLER!! Currently priced below 2026 Clark County Department of...	3 beds \| 3 baths \| 2,648 sq.ft.	$289,999	Airbnb cash on cash: N/A Traditional cash on cash: 7.32% Airbnb Rental Income: $null Traditional Rental Income: $2598 Airbnb ROI: N/A Traditional ROI: 7.32%
12 Apache Trail Winchester, KY Welcome to this charming 3-bedroom, 2-full bath ranch located in the desirable Indian Hill...	3 beds \| 2 baths \| 1,026 sq.ft.	$168,500	Airbnb cash on cash: N/A Traditional cash on cash: 6.87% Airbnb Rental Income: $null Traditional Rental Income: $1494 Airbnb ROI: N/A Traditional ROI: 6.87%
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%
13 Long Avenue Winchester, KY Charming 3 bedroom, 2 bath home situated on a large, level lot! Relax and enjoy the inviti...	3 beds \| 2 baths \| 1,297 sq.ft.	$235,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.74% Airbnb Rental Income: $null Traditional Rental Income: $1558 Airbnb ROI: N/A Traditional ROI: 4.74%
4578 Combs Ferry Road Winchester, KY Welcome to your own slice of Kentucky countryside! Situated on 59.104 picturesque acres, t...	3 beds \| 2 baths \| 1,860 sq.ft.	$1,650,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.55% Airbnb Rental Income: $null Traditional Rental Income: $2097 Airbnb ROI: N/A Traditional ROI: -0.55%
25 Oliver Street Winchester, KY Welcome to 25 Oliver Street, an affordable 3 bedroom, 1 bathroom ranch home in Winchester ...	3 beds \| 1 baths \| 900 sq.ft.	$125,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.46% Airbnb Rental Income: $null Traditional Rental Income: $1094 Airbnb ROI: N/A Traditional ROI: 6.46%
200 Dubuy Drive Winchester, KY Search no more your dream home just hit the market! You will fall in love with this one as...	3 beds \| 3 baths \| 1,858 sq.ft.	$312,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.14% Airbnb Rental Income: $null Traditional Rental Income: $1853 Airbnb ROI: N/A Traditional ROI: 4.14%
3622 Stamper Drive Winchester, KY This lovely and unique home sits at the end of a quiet street in a secluded circle and bac...	3 beds \| 3 baths \| 2,821 sq.ft.	$299,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.74% Airbnb Rental Income: $null Traditional Rental Income: $2238 Airbnb ROI: N/A Traditional ROI: 5.74%

Real Estate investment in Winchester, KY

There are 170 properties for sale in the city of Winchester . The median list price in Winchester is $217,370 and the average price per square foot is $102. In September 2026, the average monthly cash on cash return in Winchester is 5.00%. The average monthly rental income in Winchester is $2,014.

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

There are 170 investment properties available for sale in Winchester.

In 2026, 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 $2,014.

Your search for investment property begins and ends here

Investment Property for Sale in Winchester, KY

339 S Main Street

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%

120 Windsor Drive

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%

618 Westmeade Drive

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%

720 Terry Drive

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%

216 Robyn Drive

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%

411 Skylark Drive

Winchester, KY

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

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

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%