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
138 Shanahan Lane Winchester, KY This wonderful ranch home is located in the Stoney Brook Subdivision off of Casa Landa Way...	3 beds \| 2 baths \| 1,888 sq.ft.	$420,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.98% Airbnb Rental Income: $null Traditional Rental Income: $2109 Airbnb ROI: N/A Traditional ROI: 3.98%
418 Jameson Way Winchester, KY This well maintained home is ready for new owners! The first level boasts a cozy living ro...	3 beds \| 3 baths \| 1,968 sq.ft.	$270,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.39% Airbnb Rental Income: $null Traditional Rental Income: $2193 Airbnb ROI: N/A Traditional ROI: 6.39%
33 Hampton Avenue Winchester, KY Welcome to 33 Hampton Ave! This home is where Classic Charm meets Modern Updates! This...	4 beds \| 3 baths \| 3,580 sq.ft.	$435,000	Airbnb cash on cash: 2.63% Traditional cash on cash: 5.85% Airbnb Rental Income: $2142 Traditional Rental Income: $2911 Airbnb ROI: 2.63% Traditional ROI: 5.85%
19 Virginia Avenue Winchester, KY Welcome to a lovely home that has been well maintained and loved. Move in ready and price...	4 beds \| 2 baths \| 1,619 sq.ft.	$259,000	Airbnb cash on cash: 5.07% Traditional cash on cash: 6.63% Airbnb Rental Income: $2142 Traditional Rental Income: $1976 Airbnb ROI: 5.07% Traditional ROI: 6.63%
163 Hawthorne Drive Winchester, KY Now is your chance to own a home in the Earlymeade subdivision. The 2018 built home boasts...	4 beds \| 3 baths \| 2,830 sq.ft.	$499,900	Airbnb cash on cash: 2.21% Traditional cash on cash: 4.56% Airbnb Rental Income: $2142 Traditional Rental Income: $2697 Airbnb ROI: 2.21% Traditional ROI: 4.56%
502 Hewlett Court Winchester, KY OPEN HOUSE, Sunday, September 15, hours 1-3 Happiness is this two story home with lots ...	3 beds \| 3 baths \| 2,384 sq.ft.	$345,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.13% Airbnb Rental Income: $null Traditional Rental Income: $2357 Airbnb ROI: N/A Traditional ROI: 5.13%
42 Mockingbird Valley Road Winchester, KY Beautiful Hampton Manor home offers easy access to all Winchester has to offer! Located ri...	3 beds \| 3 baths \| 3,261 sq.ft.	$465,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.42% Airbnb Rental Income: $null Traditional Rental Income: $2386 Airbnb ROI: N/A Traditional ROI: 3.42%
603 Westmeade Drive Winchester, KY BIG Price Reduction!!! This Is The One You Have Been Waiting For! This 4 Bedroom 2 Bath H...	4 beds \| 2 baths \| 1,866 sq.ft.	$245,000	Airbnb cash on cash: 4.64% Traditional cash on cash: 6.81% Airbnb Rental Income: $2142 Traditional Rental Income: $2099 Airbnb ROI: 4.64% Traditional ROI: 6.81%
112 Sycamore Street Winchester, KY Don't miss out on these 2 great income producing properties that are situated on the same ...	4 beds \| 2 baths \| 1,380 sq.ft.	$169,000	Airbnb cash on cash: 7.48% Traditional cash on cash: 8.2% Airbnb Rental Income: $2142 Traditional Rental Income: $1713 Airbnb ROI: 7.48% Traditional ROI: 8.2%
509 Lasalle Court Winchester, KY Rare Ranch on a Basement! Sitting on almost an acre, this is the perfect home to bring you...	3 beds \| 3 baths \| 2,484 sq.ft.	$308,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.29% Airbnb Rental Income: $null Traditional Rental Income: $2454 Airbnb ROI: N/A Traditional ROI: 6.29%
142 Spruce Court Winchester, KY Great All Brick Ranch offers 4 bedrooms, 1.5 bathrooms, Spacious Kitchen, Nice Living Room...	4 beds \| 2 baths \| 1,215 sq.ft.	$180,000	Airbnb cash on cash: 6.92% Traditional cash on cash: 8.19% Airbnb Rental Income: $2142 Traditional Rental Income: $1813 Airbnb ROI: 6.92% Traditional ROI: 8.19%
111 South Burns Avenue Winchester, KY Reduced for quick sale!! Don't miss out on your opportunity to own a 100+ year old home l...	4 beds \| 3 baths \| 2,994 sq.ft.	$299,900	Airbnb cash on cash: 3.47% Traditional cash on cash: 8.76% Airbnb Rental Income: $2142 Traditional Rental Income: $3088 Airbnb ROI: 3.47% Traditional ROI: 8.76%
27 Sundown Lane Winchester, KY Discover your own slice of paradise at this stunning colonial-style home nestled on 71 pic...	4 beds \| 6 baths \| 5,220 sq.ft.	$2,500,000	Airbnb cash on cash: -1.21% Traditional cash on cash: 0.79% Airbnb Rental Income: $2142 Traditional Rental Income: $6222 Airbnb ROI: -1.21% Traditional ROI: 0.79%
4 Pocahontas Trail Winchester, KY Step into this beautifully updated 3-bedroom, 1-bath brick home that offers a perfect blen...	3 beds \| 1 baths \| 1,900 sq.ft.	$229,500	Airbnb cash on cash: N/A Traditional cash on cash: 4.57% Airbnb Rental Income: $null Traditional Rental Income: $1488 Airbnb ROI: N/A Traditional ROI: 4.57%
125 Buffalo Trace Winchester, KY Welcome home to this darling home located in the Buffalo Trace Subdivision. This home is o...	3 beds \| 2 baths \| 932 sq.ft.	$170,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.53% Airbnb Rental Income: $null Traditional Rental Income: $1452 Airbnb ROI: N/A Traditional ROI: 6.53%
15 Finley Road Winchester, KY Welcome to 15 Finley Rd, a quaint 3-bedroom, 1-bath home nestled in the heart of Wincheste...	3 beds \| 1 baths \| 1,392 sq.ft.	$195,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.81% Airbnb Rental Income: $null Traditional Rental Income: $1513 Airbnb ROI: N/A Traditional ROI: 5.81%
216 Prescott Lane Winchester, KY Conveniently located near shopping centers, schools and 6 minutes from the hospital. This ...	3 beds \| 3 baths \| 1,726 sq.ft.	$293,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.8% Airbnb Rental Income: $null Traditional Rental Income: $1930 Airbnb ROI: N/A Traditional ROI: 4.8%
105 Bay Hill Drive Winchester, KY MOTIVATED SELLERS. Inspections welcome but home is being sold 'as is'. This is a 3-bedroo...	3 beds \| 3 baths \| 1,376 sq.ft.	$187,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.6% Airbnb Rental Income: $null Traditional Rental Income: $1788 Airbnb ROI: N/A Traditional ROI: 7.6%
424 Alexis Way Winchester, KY Introducing the Castleton, a stunning home designed to impress in the sought-after Mallard...	3 beds \| 3 baths \| 2,405 sq.ft.	$625,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.17% Airbnb Rental Income: $null Traditional Rental Income: $1890 Airbnb ROI: N/A Traditional ROI: 1.17%
705 Oil Springs Road Winchester, KY Discover the charm of country living on 2 acres just 20 minutes from downtown Winchester! ...	4 beds \| 2 baths \| 1,572 sq.ft.	$299,000	Airbnb cash on cash: 3.49% Traditional cash on cash: 4.58% Airbnb Rental Income: $2142 Traditional Rental Income: $1904 Airbnb ROI: 3.49% Traditional ROI: 4.58%
420 Alexis Way Winchester, KY WOW! Exceptional! Attention to detail was clearly taken in the building of this stunning h...	4 beds \| 3 baths \| 2,770 sq.ft.	$850,000	Airbnb cash on cash: 0.02% Traditional cash on cash: 1.56% Airbnb Rental Income: $2142 Traditional Rental Income: $2823 Airbnb ROI: 0.02% Traditional ROI: 1.56%
31 Mockingbird Valley Road Winchester, KY This stately, split-level brick home is situated in the beautiful and desirable Hampton Ma...	4 beds \| 2 baths \| 2,520 sq.ft.	$389,900	Airbnb cash on cash: 2.61% Traditional cash on cash: 4.6% Airbnb Rental Income: $2142 Traditional Rental Income: $2323 Airbnb ROI: 2.61% Traditional ROI: 4.6%
59 Hillcrest Drive Winchester, KY Cozy ranch style home in desirable location minutes from town/GRC. Three bedrooms upstairs...	3 beds \| 2 baths \| 2,066 sq.ft.	$259,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.93% Airbnb Rental Income: $null Traditional Rental Income: $1506 Airbnb ROI: N/A Traditional ROI: 3.93%
308 West Hickman Street Winchester, KY Welcome to this beautifully remodeled gem where classic charm meets modern luxury! This sp...	5 beds \| 3 baths \| 2,681 sq.ft.	$385,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.36% Airbnb Rental Income: $null Traditional Rental Income: $2698 Airbnb ROI: N/A Traditional ROI: 5.36%
17 Elizabeth Street Winchester, KY Here's the one you've been waiting for! This completely renovated home is absolutely gorge...	3 beds \| 2 baths \| 1,450 sq.ft.	$189,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.38% Airbnb Rental Income: $null Traditional Rental Income: $1295 Airbnb ROI: N/A Traditional ROI: 5.38%
414 Alexis Way Winchester, KY Introducing the Alexis, a stunning all-brick ranch home with incredible curb appeal and a ...	3 beds \| 3 baths \| 2,643 sq.ft.	$665,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.92% Airbnb Rental Income: $null Traditional Rental Income: $2470 Airbnb ROI: N/A Traditional ROI: 1.92%
4 Elm Street Winchester, KY Complete remodel. House was gutted to the studs and rebuilt from ground up. New HVAC, Ne...	3 beds \| 2 baths \| 1,200 sq.ft.	$169,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.74% Airbnb Rental Income: $null Traditional Rental Income: $1322 Airbnb ROI: N/A Traditional ROI: 5.74%
111 Bella Shae Way Winchester, KY Welcome Home to the Park Place Floor Plan by CP Builders. This elegant ranch home features...	3 beds \| 3 baths \| 2,995 sq.ft.	$825,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.11% Airbnb Rental Income: $null Traditional Rental Income: $1465 Airbnb ROI: N/A Traditional ROI: -0.11%
31 West Hickman Street Winchester, KY We are honored to present this rare opportunity to purchase a beautiful, historic property...	4 beds \| 3 baths \| 5,328 sq.ft.	$599,000	Airbnb cash on cash: 0.83% Traditional cash on cash: 2.75% Airbnb Rental Income: $2142 Traditional Rental Income: $2668 Airbnb ROI: 0.83% Traditional ROI: 2.75%
511 Boone Avenue Winchester, KY One of a kind opportunity to live in history and in luxury in one of Winchester's finest o...	4 beds \| 5 baths \| 4,698 sq.ft.	$985,000	Airbnb cash on cash: 0.14% Traditional cash on cash: 3.2% Airbnb Rental Income: $2142 Traditional Rental Income: $4402 Airbnb ROI: 0.14% Traditional ROI: 3.2%
426 Alexis Way Winchester, KY Introducing the Merango, a classic all-brick ranch home designed for both comfort and styl...	3 beds \| 2 baths \| 2,400 sq.ft.	$685,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.98% Airbnb Rental Income: $null Traditional Rental Income: $1936 Airbnb ROI: N/A Traditional ROI: 0.98%
117 Buffalo Trace Winchester, KY NEW Price Reduction!!! Perfect 3 Bedroom 2 Bathroom Home For A First Time HomeBuyer Or Som...	3 beds \| 2 baths \| 1,072 sq.ft.	$175,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.64% Airbnb Rental Income: $null Traditional Rental Income: $1508 Airbnb ROI: N/A Traditional ROI: 6.64%
1112 Andover Drive #Lot 194 Winchester, KY New construction home for sale in Williamsburg Park Subdivision located in Franklin KY. Sp...	4 beds \| 2 baths \| 1,700 sq.ft.	$331,900	Airbnb cash on cash: 2.96% Traditional cash on cash: 4.86% Airbnb Rental Income: $2142 Traditional Rental Income: $2188 Airbnb ROI: 2.96% Traditional ROI: 4.86%
422 Alexis Way Winchester, KY Introducing the Denver, a gorgeous all-brick ranch home offering 4 bedrooms and 2.5 baths,...	4 beds \| 3 baths \| 2,537 sq.ft.	$635,000	Airbnb cash on cash: 0.63% Traditional cash on cash: 2.8% Airbnb Rental Income: $2142 Traditional Rental Income: $2882 Airbnb ROI: 0.63% Traditional ROI: 2.8%
2417 Old Boonesboro Road Winchester, KY Location! Location! This is a prime spot in Winchester. There are so many possibilities wi...	3 beds \| 1 baths \| 1,732 sq.ft.	$269,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.63% Airbnb Rental Income: $null Traditional Rental Income: $1738 Airbnb ROI: N/A Traditional ROI: 4.63%
31 Bonnie Brook Lane Winchester, KY This is rare beauty and history located in the heart of Winchester. Embrace the essence of...	5 beds \| 4 baths \| 4,091 sq.ft.	$575,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.99% Airbnb Rental Income: $null Traditional Rental Income: $3768 Airbnb ROI: N/A Traditional ROI: 4.99%
20 3rd Street Winchester, KY Complete remodel. 3 Bedroom 2 full bath. Quartz counters, fresh paint, new lighting, new...	3 beds \| 2 baths \| 1,710 sq.ft.	$179,900	Airbnb cash on cash: N/A Traditional cash on cash: 9.17% Airbnb Rental Income: $null Traditional Rental Income: $1980 Airbnb ROI: N/A Traditional ROI: 9.17%
142 Sunset Heights Winchester, KY This three bedroom Ranch home has one and 1/2 baths,a large family room with a fireplace,...	3 beds \| 2 baths \| 1,422 sq.ft.	$227,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.86% Airbnb Rental Income: $null Traditional Rental Income: $1750 Airbnb ROI: N/A Traditional ROI: 5.86%
2296 Trapp-Goffs Cor Road Winchester, KY *Seller accepted offer with 24 hour kickout clause! At the Last Minute - Buyers Changed th...	3 beds \| 2 baths \| 1,680 sq.ft.	$315,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.75% Airbnb Rental Income: $null Traditional Rental Income: $1755 Airbnb ROI: N/A Traditional ROI: 3.75%
1363 Clintonville Road Winchester, KY Embrace the potential of this 5-acre gem near Winchester and Hamburg, KY. Located in beaut...	2 beds \| 1 baths \| 1,116 sq.ft.	$340,000	Airbnb cash on cash: 0.08% Traditional cash on cash: 2.13% Airbnb Rental Income: $1081 Traditional Rental Income: $1365 Airbnb ROI: 0.08% Traditional ROI: 2.13%

Real Estate investment in Winchester, KY

There are 117 properties for sale in the city of Winchester . The median list price in Winchester is $299,900 and the average price per square foot is $145. In January 2025, the average monthly cash on cash return in Winchester is 5.00%. The average monthly rental income in Winchester is $1,940.

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

There are 117 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 $1,940.

Your search for investment property begins and ends here

Investment Property for Sale in Winchester, KY

138 Shanahan Lane

Winchester, KY

3 beds | 2 baths | 1,888 sq.ft.

$420,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.98%

Airbnb Rental Income: $null

Traditional Rental Income: $2109

Airbnb ROI: N/A

Traditional ROI: 3.98%

418 Jameson Way

Winchester, KY

3 beds | 3 baths | 1,968 sq.ft.

$270,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.39%

Airbnb Rental Income: $null

Traditional Rental Income: $2193

Airbnb ROI: N/A

Traditional ROI: 6.39%

33 Hampton Avenue

Winchester, KY

4 beds | 3 baths | 3,580 sq.ft.

$435,000

Airbnb cash on cash: 2.63%

Traditional cash on cash: 5.85%

Airbnb Rental Income: $2142

Traditional Rental Income: $2911

Airbnb ROI: 2.63%

Traditional ROI: 5.85%

19 Virginia Avenue

Winchester, KY

4 beds | 2 baths | 1,619 sq.ft.

$259,000

Airbnb cash on cash: 5.07%

Traditional cash on cash: 6.63%

Airbnb Rental Income: $2142

Traditional Rental Income: $1976

Airbnb ROI: 5.07%

Traditional ROI: 6.63%

163 Hawthorne Drive

Winchester, KY

4 beds | 3 baths | 2,830 sq.ft.

$499,900

Airbnb cash on cash: 2.21%

Traditional cash on cash: 4.56%

Airbnb Rental Income: $2142

Traditional Rental Income: $2697

Airbnb ROI: 2.21%

Traditional ROI: 4.56%

502 Hewlett Court

Winchester, KY

3 beds | 3 baths | 2,384 sq.ft.

$345,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.13%

Airbnb Rental Income: $null

Traditional Rental Income: $2357

Airbnb ROI: N/A

Traditional ROI: 5.13%

42 Mockingbird Valley Road

Winchester, KY

3 beds | 3 baths | 3,261 sq.ft.

$465,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.42%

Airbnb Rental Income: $null

Traditional Rental Income: $2386

Airbnb ROI: N/A

Traditional ROI: 3.42%

603 Westmeade Drive

Winchester, KY

4 beds | 2 baths | 1,866 sq.ft.

$245,000

Airbnb cash on cash: 4.64%

Traditional cash on cash: 6.81%

Airbnb Rental Income: $2142

Traditional Rental Income: $2099

Airbnb ROI: 4.64%