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
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.	$269,900	Airbnb cash on cash: 1.7% Traditional cash on cash: 4.6% Airbnb Rental Income: $1423 Traditional Rental Income: $1734 Airbnb ROI: 1.7% Traditional ROI: 4.6%
204 Delaplain Road Winchester, KY Unique opportunity to own a ranch with partly finished basement in a well established neig...	3 beds \| 2 baths \| 3,563 sq.ft.	$434,900	Airbnb cash on cash: 0.45% Traditional cash on cash: 1.75% Airbnb Rental Income: $1466 Traditional Rental Income: $1564 Airbnb ROI: 0.45% Traditional ROI: 1.75%
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.	$355,000	Airbnb cash on cash: 0.97% Traditional cash on cash: 2.56% Airbnb Rental Income: $1466 Traditional Rental Income: $1564 Airbnb ROI: 0.97% Traditional ROI: 2.56%
175 Overlooking Drive Winchester, KY Relax on your front porch and enjoy the view of the lake or have a barbecue on your oversi...	3 beds \| 2 baths \| 2,080 sq.ft.	$359,000	Airbnb cash on cash: 1.26% Traditional cash on cash: 2.84% Airbnb Rental Income: $1466 Traditional Rental Income: $1564 Airbnb ROI: 1.26% Traditional ROI: 2.84%
149 Winn Ave Winchester, KY Welcome to this quad plex income producing property. It is a large lot and the property si...	12 beds \| 4 baths \| 4,010 sq.ft.	$286,000	Airbnb cash on cash: N/A Traditional cash on cash: 11.65% Airbnb Rental Income: $null Traditional Rental Income: $3514 Airbnb ROI: N/A Traditional ROI: 11.65%
300 Calmes Boulevard Winchester, KY Gorgeous & Spacious 3BR/2.5BA Home in Calmes Estates . Welcome to your dream home in the h...	3 beds \| 2 baths \| 2,636 sq.ft.	$379,717	Airbnb cash on cash: 0.79% Traditional cash on cash: 3.27% Airbnb Rental Income: $1466 Traditional Rental Income: $1919 Airbnb ROI: 0.79% Traditional ROI: 3.27%
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: 0.98% Traditional cash on cash: 3.28% Airbnb Rental Income: $1423 Traditional Rental Income: $1734 Airbnb ROI: 0.98% Traditional ROI: 3.28%
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: 3.03% Traditional cash on cash: 5.83% Airbnb Rental Income: $1466 Traditional Rental Income: $1564 Airbnb ROI: 3.03% Traditional ROI: 5.83%
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: 3.16% Traditional cash on cash: 4.29% Airbnb Rental Income: $1466 Traditional Rental Income: $1258 Airbnb ROI: 3.16% Traditional ROI: 4.29%
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.	$194,000	Airbnb cash on cash: 4.06% Traditional cash on cash: 5.98% Airbnb Rental Income: $1466 Traditional Rental Income: $1387 Airbnb ROI: 4.06% Traditional ROI: 5.98%
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.	$452,500	Airbnb cash on cash: 0.37% Traditional cash on cash: 3.56% Airbnb Rental Income: $1466 Traditional Rental Income: $2386 Airbnb ROI: 0.37% Traditional ROI: 3.56%
327 Newcastle Lane Winchester, KY Welcome home to this cozy cute FOUR bedroom house with 2 full bath/ 1 half bath! Rare to f...	4 beds \| 3 baths \| 1,693 sq.ft.	$297,000	Airbnb cash on cash: 2.16% Traditional cash on cash: 4.8% Airbnb Rental Income: $1423 Traditional Rental Income: $1734 Airbnb ROI: 2.16% Traditional ROI: 4.8%
114 Magnolia Street Winchester, KY Great opportunity for investors, flippers, or anyone looking for a project with tons of po...	2 beds \| 1 baths \| 910 sq.ft.	$99,000	Airbnb cash on cash: 0.33% Traditional cash on cash: 10.18% Airbnb Rental Income: $590 Traditional Rental Income: $1251 Airbnb ROI: 0.33% Traditional ROI: 10.18%
120 Pilot View Road Winchester, KY Charming 1930 farmhouse that perfectly blends timeless character with modern updates, situ...	3 beds \| 2 baths \| 1,900 sq.ft.	$334,000	Airbnb cash on cash: 1.14% Traditional cash on cash: 2.83% Airbnb Rental Income: $1466 Traditional Rental Income: $1564 Airbnb ROI: 1.14% Traditional ROI: 2.83%
6 Monroe Avenue Winchester, KY Charming Home in the Heart of Winchester! Welcome to 6 Monroe Ave - a 3-bedroom, 2-bath ho...	3 beds \| 2 baths \| 1,305 sq.ft.	$175,000	Airbnb cash on cash: 3.79% Traditional cash on cash: 8.03% Airbnb Rental Income: $1466 Traditional Rental Income: $1740 Airbnb ROI: 3.79% Traditional ROI: 8.03%
58 hughes Avenue Winchester, KY Nice remodeled 3 bedroom and 2 bath home...Ranch on a basement...2 bed 1 bath upstairs and...	3 beds \| 2 baths \| 1,456 sq.ft.	$199,000	Airbnb cash on cash: 3.12% Traditional cash on cash: 5.93% Airbnb Rental Income: $1466 Traditional Rental Income: $1564 Airbnb ROI: 3.12% Traditional ROI: 5.93%
215 Old Log Lick Road Winchester, KY Enjoy where you live! Zen like grounds will bring inner peace in this 1,450 sq foot home o...	3 beds \| 2 baths \| 1,450 sq.ft.	$343,000	Airbnb cash on cash: 1.06% Traditional cash on cash: 2.71% Airbnb Rental Income: $1466 Traditional Rental Income: $1564 Airbnb ROI: 1.06% Traditional ROI: 2.71%
17 Euclid Avenue Winchester, KY Welcome home to 17 Euclid Ave in beautiful College Park area of Winchester. This three bed...	3 beds \| 2 baths \| 1,656 sq.ft.	$249,900	Airbnb cash on cash: 2.13% Traditional cash on cash: 3.87% Airbnb Rental Income: $1466 Traditional Rental Income: $1443 Airbnb ROI: 2.13% Traditional ROI: 3.87%
233 Cunningham Lane Winchester, KY Welcome to 233 Cunningham Lane in Winchester, KY - a versatile mini farm offering 6.7 acre...	3 beds \| 3 baths \| 2,258 sq.ft.	$429,900	Airbnb cash on cash: 0.67% Traditional cash on cash: 4.23% Airbnb Rental Income: $1466 Traditional Rental Income: $2464 Airbnb ROI: 0.67% Traditional ROI: 4.23%
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: 4% Traditional cash on cash: 6.87% Airbnb Rental Income: $1466 Traditional Rental Income: $1494 Airbnb ROI: 4% Traditional ROI: 6.87%
446 Tremont Lane Winchester, KY Are your ready for a lifestyle change? Do you need more space? How about approximately 280...	4 beds \| 2 baths \| 2,811 sq.ft.	$367,000	Airbnb cash on cash: 0.77% Traditional cash on cash: 3.57% Airbnb Rental Income: $1423 Traditional Rental Income: $1961 Airbnb ROI: 0.77% Traditional ROI: 3.57%
6239 Old Boonesboro Road Winchester, KY Welcome Home to the beautiful country! If you've been looking for quiet, space, and a plac...	4 beds \| 2 baths \| 2,659 sq.ft.	$389,900	Airbnb cash on cash: 0.62% Traditional cash on cash: 4.81% Airbnb Rental Income: $1423 Traditional Rental Income: $2530 Airbnb ROI: 0.62% Traditional ROI: 4.81%
1407 Ironworks Road Winchester, KY Welcome to this beautifully remodeled 3 bedroom, 2 full bathroom home situated on a desira...	3 beds \| 2 baths \| 1,530 sq.ft.	$259,900	Airbnb cash on cash: 1.98% Traditional cash on cash: 3.44% Airbnb Rental Income: $1466 Traditional Rental Income: $1390 Airbnb ROI: 1.98% Traditional ROI: 3.44%
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.	$325,000	Airbnb cash on cash: 1.22% Traditional cash on cash: 5.17% Airbnb Rental Income: $1466 Traditional Rental Income: $2238 Airbnb ROI: 1.22% Traditional ROI: 5.17%
424 Alexis Way Winchester, KY Introducing the Castleton, a stunning home designed to impress in the sought-after Mallard...	3 beds \| 2 baths \| 2,405 sq.ft.	$625,000	Airbnb cash on cash: -0.3% Traditional cash on cash: 1.17% Airbnb Rental Income: $1466 Traditional Rental Income: $1890 Airbnb ROI: -0.3% Traditional ROI: 1.17%
7300 Old Boonesboro Road Winchester, KY This beautiful home sits on over 7 acres of peaceful countryside. The private outdoor spac...	4 beds \| 3 baths \| 3,311 sq.ft.	$799,900	Airbnb cash on cash: -0.64% Traditional cash on cash: 1.41% Airbnb Rental Income: $1423 Traditional Rental Income: $2523 Airbnb ROI: -0.64% Traditional ROI: 1.41%
322 S Burns Avenue Winchester, KY This beautiful 1.5-story home offers all the charm of downtown in a small town, with a lib...	3 beds \| 2 baths \| 1,794 sq.ft.	$339,900	Airbnb cash on cash: 1.44% Traditional cash on cash: 3.07% Airbnb Rental Income: $1466 Traditional Rental Income: $1555 Airbnb ROI: 1.44% Traditional ROI: 3.07%
55 Hillcrest Drive Winchester, KY All-brick ranch with a full walk-out basement! This charming home offers excellent potenti...	5 beds \| 2 baths \| 2,214 sq.ft.	$296,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.84% Airbnb Rental Income: $null Traditional Rental Income: $1800 Airbnb ROI: N/A Traditional ROI: 4.84%
1128-1130 Dale Drive Winchester, KY Duplex. Both units are being sold together. Great income-producing potential. Each side of...	4 beds \| 3 baths \| 2,072 sq.ft.	$299,900	Airbnb cash on cash: 1.35% Traditional cash on cash: 6.4% Airbnb Rental Income: $1423 Traditional Rental Income: $2424 Airbnb ROI: 1.35% Traditional ROI: 6.4%
104 Bella Shae Way Winchester, KY Welcome Home to the Winchester Floor Plan by CP Builders. This elegant ranch home features...	3 beds \| 2 baths \| 2,200 sq.ft.	$591,650	Airbnb cash on cash: -0.19% Traditional cash on cash: 1.87% Airbnb Rental Income: $1466 Traditional Rental Income: $2172 Airbnb ROI: -0.19% Traditional ROI: 1.87%
1270 Sewell Shop Road Winchester, KY Country Living with Convenience - 5 Fenced Acres in Winchester, KY Enjoy the perfect blend...	5 beds \| 2 baths \| 1,952 sq.ft.	$354,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.2% Airbnb Rental Income: $null Traditional Rental Income: $2213 Airbnb ROI: N/A Traditional ROI: 5.2%
12 Linden Avenue Winchester, KY Cute ranch with easy access to I-64 and downtown Winchester. Walk to the breweries, shoppi...	3 beds \| 2 baths \| 1,050 sq.ft.	$235,000	Airbnb cash on cash: 2.87% Traditional cash on cash: 6.45% Airbnb Rental Income: $1466 Traditional Rental Income: $1828 Airbnb ROI: 2.87% Traditional ROI: 6.45%
221 S Highland Street Winchester, KY INVESTOR SPECIAL, You have the opportunity to purchase a fully occupied tri-plex in the he...	5 beds \| 3 baths \| 3,007 sq.ft.	$246,400	Airbnb cash on cash: N/A Traditional cash on cash: 8.04% Airbnb Rental Income: $null Traditional Rental Income: $2277 Airbnb ROI: N/A Traditional ROI: 8.04%
414 Alexis Way Winchester, KY Introducing the Alexis, a stunning all-brick ranch home with incredible curb appeal and a ...	3 beds \| 2 baths \| 2,643 sq.ft.	$665,000	Airbnb cash on cash: -0.39% Traditional cash on cash: 1.92% Airbnb Rental Income: $1466 Traditional Rental Income: $2470 Airbnb ROI: -0.39% Traditional ROI: 1.92%
23 Kittison Drive Winchester, KY 24 HOUR KICKOUT! ONE-OWNER BRICK RANCH HOME!! Now that I have your attention, schedule a s...	3 beds \| 2 baths \| 1,346 sq.ft.	$235,000	Airbnb cash on cash: 2.38% Traditional cash on cash: 3.63% Airbnb Rental Income: $1466 Traditional Rental Income: $1312 Airbnb ROI: 2.38% Traditional ROI: 3.63%
357 Silverton Way Winchester, KY This updated home offers easy access to I-64 and downtown Winchester. See ceiling fans in ...	3 beds \| 2 baths \| 1,502 sq.ft.	$243,000	Airbnb cash on cash: 2.18% Traditional cash on cash: 2.96% Airbnb Rental Income: $1466 Traditional Rental Income: $1213 Airbnb ROI: 2.18% Traditional ROI: 2.96%
111 Bella Shae Way Winchester, KY Welcome Home to the Park Place Floor Plan by CP Builders. This elegant ranch home features...	3 beds \| 2 baths \| 2,995 sq.ft.	$825,000	Airbnb cash on cash: -0.67% Traditional cash on cash: -0.11% Airbnb Rental Income: $1466 Traditional Rental Income: $1465 Airbnb ROI: -0.67% Traditional ROI: -0.11%
313 S Burns Avenue Winchester, KY This 3 bedroom, 2 bath home sits on a corner lot with hardwood floors and a two-car detach...	3 beds \| 2 baths \| 1,518 sq.ft.	$215,000	Airbnb cash on cash: 2.76% Traditional cash on cash: 4.5% Airbnb Rental Income: $1466 Traditional Rental Income: $1387 Airbnb ROI: 2.76% Traditional ROI: 4.5%
720 Estes Drive Winchester, KY This charming brick ranch is truly move-in ready. Offering 3 bedrooms, 1.5 baths, a welcom...	3 beds \| 2 baths \| 1,494 sq.ft.	$244,900	Airbnb cash on cash: 2.21% Traditional cash on cash: 3.18% Airbnb Rental Income: $1466 Traditional Rental Income: $1258 Airbnb ROI: 2.21% Traditional ROI: 3.18%
119 Tower Lane Winchester, KY A rare and refined retreat set on five unrestricted acres in Winchester. Privately positio...	3 beds \| 1 baths \| 1,273 sq.ft.	$289,000	Airbnb cash on cash: 1.6% Traditional cash on cash: 2.18% Airbnb Rental Income: $1466 Traditional Rental Income: $1192 Airbnb ROI: 1.6% Traditional ROI: 2.18%

Real Estate investment in Winchester, KY

There are 146 properties for sale in the city of Winchester . The median list price in Winchester is $296,000 and the average price per square foot is $132. In March 2026, the average monthly cash on cash return in Winchester is 5.00%. The average monthly rental income in Winchester is $1,734.

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

There are 146 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 $1,734.

Your search for investment property begins and ends here

Investment Property for Sale in Winchester, KY

120 Windsor Drive

Winchester, KY

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

$269,900

Airbnb cash on cash: 1.7%

Traditional cash on cash: 4.6%

Airbnb Rental Income: $1423

Traditional Rental Income: $1734

Airbnb ROI: 1.7%

Traditional ROI: 4.6%

204 Delaplain Road

Winchester, KY

3 beds | 2 baths | 3,563 sq.ft.

$434,900

Airbnb cash on cash: 0.45%

Traditional cash on cash: 1.75%

Airbnb Rental Income: $1466

Traditional Rental Income: $1564

Airbnb ROI: 0.45%

Traditional ROI: 1.75%

221 Moundale Avenue

Winchester, KY

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

$355,000

Airbnb cash on cash: 0.97%

Traditional cash on cash: 2.56%

Airbnb Rental Income: $1466

Traditional Rental Income: $1564

Airbnb ROI: 0.97%

Traditional ROI: 2.56%

175 Overlooking Drive

Winchester, KY

3 beds | 2 baths | 2,080 sq.ft.

$359,000

Airbnb cash on cash: 1.26%

Traditional cash on cash: 2.84%

Airbnb Rental Income: $1466

Traditional Rental Income: $1564

Airbnb ROI: 1.26%

Traditional ROI: 2.84%

149 Winn Ave

Winchester, KY

12 beds | 4 baths | 4,010 sq.ft.

$286,000

Airbnb cash on cash: N/A

Traditional cash on cash: 11.65%

Airbnb Rental Income: $null

Traditional Rental Income: $3514

Airbnb ROI: N/A

Traditional ROI: 11.65%

300 Calmes Boulevard

Winchester, KY

3 beds | 2 baths | 2,636 sq.ft.

$379,717

Airbnb cash on cash: 0.79%

Traditional cash on cash: 3.27%

Airbnb Rental Income: $1466

Traditional Rental Income: $1919

Airbnb ROI: 0.79%

Traditional ROI: 3.27%

168 Buckingham Lane

Winchester, KY

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

$339,900

Airbnb cash on cash: 0.98%

Traditional cash on cash: 3.28%

Airbnb Rental Income: $1423

Traditional Rental Income: $1734

Airbnb ROI: 0.98%

Traditional ROI: 3.28%

128 Bay Hill Drive

Winchester, KY

3 beds | 2 baths | 1,289 sq.ft.

$200,000

Airbnb cash on cash: 3.03%

Traditional cash on cash: 5.83%

Airbnb Rental Income: $1466

Traditional Rental Income: $1564

Airbnb ROI: 3.03%