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Airbnb For Sale in Winchester, KY

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
121 Hampton Avenue Winchester, KY Picturesque Setting!!! Are You Looking For A Large Ranch On A Basement On A Large Private ...	3 beds \| 2 baths \| 2,248 sq.ft.	$329,900	Airbnb cash on cash: 3.94% Traditional cash on cash: 3.45% Airbnb Rental Income: $2347 Traditional Rental Income: $1614 Airbnb ROI: 3.94% Traditional ROI: 3.45%
1651 Clintonville Road Winchester, KY This property, located just minutes from Winchester, Lexington, and Paris is now available...	3 beds \| 3 baths \| 2,546 sq.ft.	$580,000	Airbnb cash on cash: 1.89% Traditional cash on cash: 1.69% Airbnb Rental Income: $2347 Traditional Rental Income: $1659 Airbnb ROI: 1.89% Traditional ROI: 1.69%
130 Hilltop Drive Winchester, KY Black Friday Special!! Seller is offering a $5,000 credit at closing to use towards closin...	3 beds \| 1 baths \| 1,465 sq.ft.	$215,000	Airbnb cash on cash: 6.76% Traditional cash on cash: 3.92% Airbnb Rental Income: $2347 Traditional Rental Income: $1189 Airbnb ROI: 6.76% Traditional ROI: 3.92%
307 Wayside Court Winchester, KY This lovely brick ranch home is conveniently located between Winchester and Lexington on H...	3 beds \| 2 baths \| 1,486 sq.ft.	$259,900	Airbnb cash on cash: 5.27% Traditional cash on cash: 3.5% Airbnb Rental Income: $2347 Traditional Rental Income: $1333 Airbnb ROI: 5.27% Traditional ROI: 3.5%
221 Holiday Road Winchester, KY This nice 3 bedroom 2 bath is sitting on a full basement. It's close to retail shops, golf...	3 beds \| 2 baths \| 1,960 sq.ft.	$185,000	Airbnb cash on cash: 7.81% Traditional cash on cash: 6.37% Airbnb Rental Income: $2347 Traditional Rental Income: $1514 Airbnb ROI: 7.81% Traditional ROI: 6.37%
1275 Log Lick Road Winchester, KY Discover Kentucky living at 1275 Old Log Lick Road, a breathtaking property spanning 421.8...	3 beds \| 2 baths \| 1,392 sq.ft.	$1,525,000	Airbnb cash on cash: 0.07% Traditional cash on cash: -0.27% Airbnb Rental Income: $2347 Traditional Rental Income: $1277 Airbnb ROI: 0.07% Traditional ROI: -0.27%
9 Bon Haven Avenue Winchester, KY Enjoy this wonderful home in the heart of Winchester on a quiet street with Legacy Park li...	3 beds \| 2 baths \| 2,078 sq.ft.	$244,500	Airbnb cash on cash: 5.8% Traditional cash on cash: 4.73% Airbnb Rental Income: $2347 Traditional Rental Income: $1521 Airbnb ROI: 5.8% Traditional ROI: 4.73%
36 7th Street Winchester, KY New Construction! 3BR/2BA ranch on a quiet street. This is a must see home! Wouldn't it...	3 beds \| 2 baths \| 1,080 sq.ft.	$194,999	Airbnb cash on cash: 7.98% Traditional cash on cash: 5.34% Airbnb Rental Income: $2347 Traditional Rental Income: $1279 Airbnb ROI: 7.98% Traditional ROI: 5.34%
552 Barlow Drive Winchester, KY Brick ranch home with an amazing covered front porch and wrap around driveway all the way ...	3 beds \| 2 baths \| 1,746 sq.ft.	$249,000	Airbnb cash on cash: 5.75% Traditional cash on cash: 4.37% Airbnb Rental Income: $2347 Traditional Rental Income: $1442 Airbnb ROI: 5.75% Traditional ROI: 4.37%
303 West Washington Street Winchester, KY New Construction! Should be complete 11/20/23! This 3BR/2BA home is on a crawl space. Y...	3 beds \| 2 baths \| 1,080 sq.ft.	$194,999	Airbnb cash on cash: 7.99% Traditional cash on cash: 5.38% Airbnb Rental Income: $2347 Traditional Rental Income: $1283 Airbnb ROI: 7.99% Traditional ROI: 5.38%
19 Lee Street Winchester, KY 1,488 SF single family home that sits .72 acres with a 720 SF building behind it. Currentl...	3 beds \| 3 baths \| 1,488 sq.ft.	$225,000	Airbnb cash on cash: 6.43% Traditional cash on cash: 4.7% Airbnb Rental Income: $2347 Traditional Rental Income: $1399 Airbnb ROI: 6.43% Traditional ROI: 4.7%
113 Mary Way Winchester, KY Nestled in the charming town of Winchester, Kentucky, this delightful house offers the per...	3 beds \| 2 baths \| 1,050 sq.ft.	$205,000	Airbnb cash on cash: 7.11% Traditional cash on cash: 4.26% Airbnb Rental Income: $2347 Traditional Rental Income: $1212 Airbnb ROI: 7.11% Traditional ROI: 4.26%
715 White-Conkwright Road Winchester, KY Move in Ready 3 bedrooms, 2 full bathrooms sitting on just over 5 acres! NEW flooring, NEW...	3 beds \| 2 baths \| 1,459 sq.ft.	$275,000	Airbnb cash on cash: 4.63% Traditional cash on cash: 2.67% Airbnb Rental Income: $2347 Traditional Rental Income: $1258 Airbnb ROI: 4.63% Traditional ROI: 2.67%
122 Inverness Lane Winchester, KY This well-maintained townhome offers an open floor plan with a spacious living room and di...	2 beds \| 2 baths \| 1,400 sq.ft.	$200,000	Airbnb cash on cash: 4.08% Traditional cash on cash: 2.7% Airbnb Rental Income: $1650 Traditional Rental Income: $924 Airbnb ROI: 4.08% Traditional ROI: 2.7%
432 West West Washington Street Winchester, KY Welcome to your new home! This modest yet inviting 3-bedroom, 2-bathroom home offers the p...	3 beds \| 2 baths \| 1,088 sq.ft.	$165,000	Airbnb cash on cash: 8.81% Traditional cash on cash: 5.21% Airbnb Rental Income: $2347 Traditional Rental Income: $1200 Airbnb ROI: 8.81% Traditional ROI: 5.21%
2100 Miller Hunt Road Winchester, KY Excited to introduce this unique opportunity! Situated on 5 Acres of Central Kentucky beau...	3 beds \| 2 baths \| 1,550 sq.ft.	$349,000	Airbnb cash on cash: 3.28% Traditional cash on cash: 1.9% Airbnb Rental Income: $2347 Traditional Rental Income: $1314 Airbnb ROI: 3.28% Traditional ROI: 1.9%
1136 Lafayette Boulevard Winchester, KY Introducing this charming brick ranch home conveniently located near shopping, and restaur...	3 beds \| 2 baths \| 2,183 sq.ft.	$340,000	Airbnb cash on cash: 3.42% Traditional cash on cash: 2.76% Airbnb Rental Income: $2347 Traditional Rental Income: $1558 Airbnb ROI: 3.42% Traditional ROI: 2.76%
105 Linden Avenue Winchester, KY Absolute Must See!!! This Adorable 3-bedroom 2 bath cozy home awaits its lucky owner. Ho...	3 beds \| 2 baths \| 1,360 sq.ft.	$219,500	Airbnb cash on cash: 6.84% Traditional cash on cash: 4.17% Airbnb Rental Income: $2347 Traditional Rental Income: $1213 Airbnb ROI: 6.84% Traditional ROI: 4.17%
21 Kentucky Street Winchester, KY Welcome home to this immaculate, fully renovated 3-bedroom, 2-bathroom beauty. Step onto g...	3 beds \| 2 baths \| 1,340 sq.ft.	$189,500	Airbnb cash on cash: 7.47% Traditional cash on cash: 4.85% Airbnb Rental Income: $2347 Traditional Rental Income: $1295 Airbnb ROI: 7.47% Traditional ROI: 4.85%
291 Calmes Boulevard Winchester, KY Welcome to this move in ready, freshly remodel home that features 3 beds, and 2.5 baths. A...	3 beds \| 3 baths \| 1,688 sq.ft.	$299,900	Airbnb cash on cash: 4.11% Traditional cash on cash: 2.99% Airbnb Rental Income: $2347 Traditional Rental Income: $1452 Airbnb ROI: 4.11% Traditional ROI: 2.99%
303 Hummingbird Drive Winchester, KY Brick ranch with a full basement, It has a living room open to kitchen, 3 bedrooms, bath, ...	3 beds \| 1 baths \| 1,169 sq.ft.	$187,000	Airbnb cash on cash: 7.6% Traditional cash on cash: 4.29% Airbnb Rental Income: $2347 Traditional Rental Income: $1180 Airbnb ROI: 7.6% Traditional ROI: 4.29%
129 Kentucky Street Winchester, KY This income producing single-family home is perfect for investors looking to add or start ...	2 beds \| 1 baths \| 1,032 sq.ft.	$125,000	Airbnb cash on cash: 7.92% Traditional cash on cash: 4.86% Airbnb Rental Income: $1650 Traditional Rental Income: $818 Airbnb ROI: 7.92% Traditional ROI: 4.86%
2270 Mina Station Road Winchester, KY A country living dream!! This 3 bedroom 2 full bath home on 5.22 acres with a detached gar...	3 beds \| 2 baths \| 1,358 sq.ft.	$220,000	Airbnb cash on cash: 6.21% Traditional cash on cash: 3.66% Airbnb Rental Income: $2347 Traditional Rental Income: $1235 Airbnb ROI: 6.21% Traditional ROI: 3.66%
5600 Ecton Road Winchester, KY Nestled on 13 acres of serene countryside, this property is a horse lovers dream, offering...	3 beds \| 3 baths \| 2,841 sq.ft.	$515,000	Airbnb cash on cash: 2.17% Traditional cash on cash: 1.85% Airbnb Rental Income: $2347 Traditional Rental Income: $1609 Airbnb ROI: 2.17% Traditional ROI: 1.85%
132 Gadwall Lane Winchester, KY This dreamhouse is now available for you to make your new home. Enter the home from the in...	3 beds \| 3 baths \| 2,511 sq.ft.	$574,000	Airbnb cash on cash: 1.3% Traditional cash on cash: 1.11% Airbnb Rental Income: $2347 Traditional Rental Income: $1668 Airbnb ROI: 1.3% Traditional ROI: 1.11%
720 Estes Drive Winchester, KY Check out this great ranch home! This home features 3 beds/1.5 baths complete with bonus r...	3 beds \| 2 baths \| 1,494 sq.ft.	$210,000	Airbnb cash on cash: 6.59% Traditional cash on cash: 4.03% Airbnb Rental Income: $2347 Traditional Rental Income: $1258 Airbnb ROI: 6.59% Traditional ROI: 4.03%
119 Finley Road Winchester, KY	3 beds \| 2 baths \| 1,480 sq.ft.	$180,000	Airbnb cash on cash: 8.37% Traditional cash on cash: 5.66% Airbnb Rental Income: $2347 Traditional Rental Income: $1304 Airbnb ROI: 8.37% Traditional ROI: 5.66%
111 E Clark Drive Winchester, KY This lovely home sits in a great neighborhood. The home offers 3 bedrooms and 2 full bath...	3 beds \| 2 baths \| 1,460 sq.ft.	$235,000	Airbnb cash on cash: 6.17% Traditional cash on cash: 3.84% Airbnb Rental Income: $2347 Traditional Rental Income: $1249 Airbnb ROI: 6.17% Traditional ROI: 3.84%
120 Milwood Drive Winchester, KY This ranch on a basement boasts beautiful hardwood flooring on the main level where you wi...	3 beds \| 2 baths \| 1,853 sq.ft.	$245,000	Airbnb cash on cash: 5.41% Traditional cash on cash: 3.99% Airbnb Rental Income: $2347 Traditional Rental Income: $1439 Airbnb ROI: 5.41% Traditional ROI: 3.99%
11705 Irvine Road Winchester, KY Calling all first time homebuyers. Discover a beautifully appointed 3 bed, 2 bath ranch, c...	3 beds \| 2 baths \| 2,668 sq.ft.	$280,000	Airbnb cash on cash: 4.52% Traditional cash on cash: 3.51% Airbnb Rental Income: $2347 Traditional Rental Income: $1500 Airbnb ROI: 4.52% Traditional ROI: 3.51%
312 Buffalo Trace Winchester, KY You will love this charming country home that's only minutes from downtown Winchester. Th...	3 beds \| 2 baths \| 1,284 sq.ft.	$239,700	Airbnb cash on cash: 5.56% Traditional cash on cash: 3.02% Airbnb Rental Income: $2347 Traditional Rental Income: $1190 Airbnb ROI: 5.56% Traditional ROI: 3.02%
729 Wayland Drive Winchester, KY Convenient location to Lexington and Winchester is 10 minutes away and 15 minutes to Hambu...	3 beds \| 2 baths \| 2,079 sq.ft.	$279,000	Airbnb cash on cash: 4.54% Traditional cash on cash: 3.3% Airbnb Rental Income: $2347 Traditional Rental Income: $1441 Airbnb ROI: 4.54% Traditional ROI: 3.3%
116 Arlington Road Winchester, KY Cute little ranch house with tons of potential on a large lot. located directly across fro...	1 beds \| 1 baths \| 1,089 sq.ft.	$127,900	Airbnb cash on cash: 5.64% Traditional cash on cash: 5.05% Airbnb Rental Income: $1439 Traditional Rental Income: $938 Airbnb ROI: 5.64% Traditional ROI: 5.05%
155 Spruce Court Winchester, KY Price Improvement!! Need space? Check out this great UPDATED 3 bedroom 2 bath brick ranc...	3 beds \| 2 baths \| 1,569 sq.ft.	$219,000	Airbnb cash on cash: 6.25% Traditional cash on cash: 4.1% Airbnb Rental Income: $2347 Traditional Rental Income: $1321 Airbnb ROI: 6.25% Traditional ROI: 4.1%
403 Fairholme Way Winchester, KY New Construction!!!! 3BR/2BA ranch on a full walkout basement, with an oversized two car g...	3 beds \| 2 baths \| 1,621 sq.ft.	$325,000	Airbnb cash on cash: 4.44% Traditional cash on cash: 3.4% Airbnb Rental Income: $2347 Traditional Rental Income: $1452 Airbnb ROI: 4.44% Traditional ROI: 3.4%
373 Crescent Avenue Winchester, KY This remodeled gem has 3 bedroom, 2 full bath & 2009 SF and is located in the heart of Win...	3 beds \| 2 baths \| 2,009 sq.ft.	$249,500	Airbnb cash on cash: 5.28% Traditional cash on cash: 4.45% Airbnb Rental Income: $2347 Traditional Rental Income: $1573 Airbnb ROI: 5.28% Traditional ROI: 4.45%
114 Honeysuckle Court Winchester, KY This beautiful home is in a prime location. Just minutes from a public golf course, severa...	3 beds \| 2 baths \| 1,394 sq.ft.	$225,000	Airbnb cash on cash: 6.03% Traditional cash on cash: 3.87% Airbnb Rental Income: $2347 Traditional Rental Income: $1306 Airbnb ROI: 6.03% Traditional ROI: 3.87%
405 Fairholme Way Winchester, KY NEW CONSTRUCTION- This three bedroom ranch on an unfinished basement has an oversized two ...	3 beds \| 2 baths \| 1,565 sq.ft.	$323,500	Airbnb cash on cash: 3.68% Traditional cash on cash: 2.62% Airbnb Rental Income: $2347 Traditional Rental Income: $1446 Airbnb ROI: 3.68% Traditional ROI: 2.62%
216 Forest Court Winchester, KY This is a wonderful home in Winchester, KY, that offers tons of space for the price. You w...	3 beds \| 2 baths \| 2,301 sq.ft.	$175,000	Airbnb cash on cash: 8.58% Traditional cash on cash: 7.49% Airbnb Rental Income: $2347 Traditional Rental Income: $1585 Airbnb ROI: 8.58% Traditional ROI: 7.49%
13 Euclid Avenue Winchester, KY You will love this completely renovated move-in ready home! Meticulous care was taken to r...	3 beds \| 2 baths \| 1,893 sq.ft.	$234,900	Airbnb cash on cash: 5.71% Traditional cash on cash: 4.24% Airbnb Rental Income: $2347 Traditional Rental Income: $1440 Airbnb ROI: 5.71% Traditional ROI: 4.24%

Vacation Rentals in Winchester

There are 49 vacation rental properties available for sale in the city of Winchester . The median list price of Airbnb properties available for sale in Winchester is $254,900 and the average price per square foot is $117. The cash on cash return on vacation rentals in Winchester is 6.00%. The average monthly short term rental income in Winchester is $2,347.

Winchester, KY Short Term Rentals FAQs for Buyers, Sellers and Investors

There are 49 Airbnb properties available for sale in Winchester.

In 2023, the best neighborhood to buy short term rental property is Winchester.

In November 2023, the average Airbnb occupancy rate in Winchester is 51%.

Airbnb data on vacation rentals in Winchester, KY is available at Mashvisor. You can access data such as listings, real-time pricing trends, Winchester, KY market insights, guest information and booking details, seasonality trends and historical Winchester, KY Airbnb performance data.

Your search for investment property begins and ends here

Airbnb For Sale in Winchester, KY

121 Hampton Avenue

Winchester, KY

3 beds | 2 baths | 2,248 sq.ft.

$329,900

Airbnb cash on cash: 3.94%

Traditional cash on cash: 3.45%

Airbnb Rental Income: $2347

Traditional Rental Income: $1614

Airbnb ROI: 3.94%

Traditional ROI: 3.45%

1651 Clintonville Road

Winchester, KY

3 beds | 3 baths | 2,546 sq.ft.

$580,000

Airbnb cash on cash: 1.89%

Traditional cash on cash: 1.69%

Airbnb Rental Income: $2347

Traditional Rental Income: $1659

Airbnb ROI: 1.89%

Traditional ROI: 1.69%

130 Hilltop Drive

Winchester, KY

3 beds | 1 baths | 1,465 sq.ft.

$215,000

Airbnb cash on cash: 6.76%

Traditional cash on cash: 3.92%

Airbnb Rental Income: $2347

Traditional Rental Income: $1189

Airbnb ROI: 6.76%

Traditional ROI: 3.92%

307 Wayside Court

Winchester, KY

3 beds | 2 baths | 1,486 sq.ft.

$259,900

Airbnb cash on cash: 5.27%

Traditional cash on cash: 3.5%

Airbnb Rental Income: $2347

Traditional Rental Income: $1333

Airbnb ROI: 5.27%

Traditional ROI: 3.5%

221 Holiday Road

Winchester, KY

3 beds | 2 baths | 1,960 sq.ft.

$185,000

Airbnb cash on cash: 7.81%

Traditional cash on cash: 6.37%

Airbnb Rental Income: $2347

Traditional Rental Income: $1514

Airbnb ROI: 7.81%

Traditional ROI: 6.37%

1275 Log Lick Road

Winchester, KY

3 beds | 2 baths | 1,392 sq.ft.

$1,525,000

Airbnb cash on cash: 0.07%

Traditional cash on cash: -0.27%

Airbnb Rental Income: $2347

Traditional Rental Income: $1277

Airbnb ROI: 0.07%

Traditional ROI: -0.27%

9 Bon Haven Avenue

Winchester, KY

3 beds | 2 baths | 2,078 sq.ft.

$244,500

Airbnb cash on cash: 5.8%

Traditional cash on cash: 4.73%

Airbnb Rental Income: $2347

Traditional Rental Income: $1521

Airbnb ROI: 5.8%

Traditional ROI: 4.73%

36 7th Street

Winchester, KY

3 beds | 2 baths | 1,080 sq.ft.

$194,999

Airbnb cash on cash: 7.98%

Traditional cash on cash: 5.34%

Airbnb Rental Income: $2347

Traditional Rental Income: $1279

Airbnb ROI: 7.98%