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.

Single Family Residential For Salhttf L For Salhttf L For Salhttf L For Salhttf L Fory Residential for Sale in Winchester, KY

Search for Single Family Residential For Salhttf L For Salhttf L For Salhttf L For Salhttf L Fory Residential for Sale in Winchester, Kentucky. Browse all of Mashvisor’s Single Family Residential For Salhttf L For Salhttf L For Salhttf L For Salhttf L Fory Residential listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 146 Single Family Residential For Salhttf L For Salhttf L For Salhttf L For Salhttf L Fory Residential 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
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: 1.83% Traditional cash on cash: 4.24% Airbnb Rental Income: $1423 Traditional Rental Income: $1588 Airbnb ROI: 1.83% Traditional ROI: 4.24%
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: 2.28% Airbnb Rental Income: $1466 Traditional Rental Income: $1780 Airbnb ROI: 0.45% Traditional ROI: 2.28%
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.	$350,000	Airbnb cash on cash: 1% Traditional cash on cash: 6.88% Airbnb Rental Income: $1466 Traditional Rental Income: $2964 Airbnb ROI: 1% Traditional ROI: 6.88%
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: 4.53% Airbnb Rental Income: $1466 Traditional Rental Income: $2134 Airbnb ROI: 1.26% Traditional ROI: 4.53%
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: 6.63% Airbnb Rental Income: $1423 Traditional Rental Income: $2804 Airbnb ROI: 0.98% Traditional ROI: 6.63%
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: 6.08% Airbnb Rental Income: $1466 Traditional Rental Income: $1613 Airbnb ROI: 3.03% 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: 4.14% Traditional cash on cash: 7.95% Airbnb Rental Income: $1466 Traditional Rental Income: $1722 Airbnb ROI: 4.14% 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: 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: 5.34% Airbnb Rental Income: $1423 Traditional Rental Income: $1887 Airbnb ROI: 2.16% Traditional ROI: 5.34%
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: 4.43% Airbnb Rental Income: $1466 Traditional Rental Income: $2066 Airbnb ROI: 1.14% Traditional ROI: 4.43%
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: 6.46% Airbnb Rental Income: $1466 Traditional Rental Income: $1663 Airbnb ROI: 3.12% Traditional ROI: 6.46%
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: 3.21% Airbnb Rental Income: $1466 Traditional Rental Income: $1724 Airbnb ROI: 1.06% Traditional ROI: 3.21%
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.	$254,900	Airbnb cash on cash: 2.05% Traditional cash on cash: 3.54% Airbnb Rental Income: $1466 Traditional Rental Income: $1390 Airbnb ROI: 2.05% Traditional ROI: 3.54%
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 \| 3 baths \| 1,794 sq.ft.	$335,000	Airbnb cash on cash: 1.47% Traditional cash on cash: 3.13% Airbnb Rental Income: $1466 Traditional Rental Income: $1555 Airbnb ROI: 1.47% Traditional ROI: 3.13%
3610 Stamper Drive Winchester, KY You will absolutely love this well cared for and wonderfully updated ranch! This home has ...	3 beds \| 2 baths \| 1,148 sq.ft.	$239,900	Airbnb cash on cash: 2.29% Traditional cash on cash: 4.54% Airbnb Rental Income: $1466 Traditional Rental Income: $1543 Airbnb ROI: 2.29% Traditional ROI: 4.54%
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.	$239,999	Airbnb cash on cash: 2.23% Traditional cash on cash: 3.02% Airbnb Rental Income: $1466 Traditional Rental Income: $1213 Airbnb ROI: 2.23% Traditional ROI: 3.02%
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%
422 Alexis Way Winchester, KY Introducing the Denver, a gorgeous all-brick ranch home offering 4 bedrooms and 2.5 baths,...	4 beds \| 2 baths \| 2,537 sq.ft.	$635,000	Airbnb cash on cash: -0.38% Traditional cash on cash: 2.8% Airbnb Rental Income: $1423 Traditional Rental Income: $2882 Airbnb ROI: -0.38% Traditional ROI: 2.8%

Your search for investment property begins and ends here

Single Family Residential For Salhttf L For Salhttf L For Salhttf L For Salhttf L Fory Residential for Sale in Winchester, KY

120 Windsor Drive

Winchester, KY

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

$259,900

Airbnb cash on cash: 1.83%

Traditional cash on cash: 4.24%

Airbnb Rental Income: $1423

Traditional Rental Income: $1588

Airbnb ROI: 1.83%

Traditional ROI: 4.24%

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: 2.28%

Airbnb Rental Income: $1466

Traditional Rental Income: $1780

Airbnb ROI: 0.45%

Traditional ROI: 2.28%

221 Moundale Avenue

Winchester, KY

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

$350,000

Airbnb cash on cash: 1%

Traditional cash on cash: 6.88%

Airbnb Rental Income: $1466

Traditional Rental Income: $2964

Airbnb ROI: 1%

Traditional ROI: 6.88%

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: 4.53%

Airbnb Rental Income: $1466

Traditional Rental Income: $2134

Airbnb ROI: 1.26%

Traditional ROI: 4.53%

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: 6.63%

Airbnb Rental Income: $1423

Traditional Rental Income: $2804

Airbnb ROI: 0.98%

Traditional ROI: 6.63%

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: 6.08%

Airbnb Rental Income: $1466

Traditional Rental Income: $1613

Airbnb ROI: 3.03%

Traditional ROI: 6.08%

29 Euclid Avenue

Winchester, KY

3 beds | 2 baths | 1,498 sq.ft.

$190,000

Airbnb cash on cash: 4.14%

Traditional cash on cash: 7.95%

Airbnb Rental Income: $1466

Traditional Rental Income: $1722

Airbnb ROI: 4.14%

Traditional ROI: 7.95%

59 Holiday Road

Winchester, KY

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%