Airbnb Properties for Sale in Winchester, KY

Looking for a vacation rental investment in Winchester, KY with high ROI ?

Explore a range of newly added short-term rental homes in Winchester, KY. Make a smart investment with newly available Airbnb properties and find the ideal high-ROI property for sale.

Airbnb For Sale in Winchester, KY

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
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: 6.68% Traditional cash on cash: 5.13% Airbnb Rental Income: $3657 Traditional Rental Income: $2357 Airbnb ROI: 6.68% 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: 4.5% Traditional cash on cash: 3.42% Airbnb Rental Income: $3657 Traditional Rental Income: $2386 Airbnb ROI: 4.5% Traditional ROI: 3.42%
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.	$175,000	Airbnb cash on cash: 8.27% Traditional cash on cash: 7.87% Airbnb Rental Income: $2363 Traditional Rental Income: $1713 Airbnb ROI: 8.27% Traditional ROI: 7.87%
2482 Mina Station Road Winchester, KY Move in Ready! 3 bedroom 2 full bath. Gorgeous updated kitchen with TONS of cabinet space,...	3 beds \| 2 baths \| 1,756 sq.ft.	$310,000	Airbnb cash on cash: 7.63% Traditional cash on cash: 3.72% Airbnb Rental Income: $3657 Traditional Rental Income: $1719 Airbnb ROI: 7.63% Traditional ROI: 3.72%
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: 7.69% Traditional cash on cash: 6.29% Airbnb Rental Income: $3657 Traditional Rental Income: $2454 Airbnb ROI: 7.69% Traditional ROI: 6.29%
122 Buckingham Lane Winchester, KY Move- in ready 3 bed and 2 bath ranch!! Now that I have your attention, how about some re...	3 beds \| 2 baths \| 1,240 sq.ft.	$280,000	Airbnb cash on cash: 8.63% Traditional cash on cash: 2.84% Airbnb Rental Income: $3657 Traditional Rental Income: $1331 Airbnb ROI: 8.63% Traditional ROI: 2.84%
440 Flanagan Station Road Winchester, KY Beautiful, Sprawling Brick Ranch Home on 7.8 Acres * 3-Stall Barn with Run-in/Hay Storage ...	3 beds \| 3 baths \| 2,620 sq.ft.	$525,000	Airbnb cash on cash: 3.78% Traditional cash on cash: 2.97% Airbnb Rental Income: $3657 Traditional Rental Income: $2461 Airbnb ROI: 3.78% Traditional ROI: 2.97%
209 Robyn Drive Winchester, KY Welcome to this beautiful, newly renovated 3 bedroom 2 1/2 bathroom ranch on a finished ba...	3 beds \| 3 baths \| 1,825 sq.ft.	$275,000	Airbnb cash on cash: 8.81% Traditional cash on cash: 5.16% Airbnb Rental Income: $3657 Traditional Rental Income: $1910 Airbnb ROI: 8.81% Traditional ROI: 5.16%
104 Bella Shae Way Winchester, KY Proposed construction on lot 117 in luxurious new subdivision Mallard Cove! This gorgeous ...	3 beds \| 2 baths \| 2,200 sq.ft.	$516,000	Airbnb cash on cash: 3.83% Traditional cash on cash: 2.41% Airbnb Rental Income: $3657 Traditional Rental Income: $2172 Airbnb ROI: 3.83% Traditional ROI: 2.41%
414 Alexis Way Winchester, KY Welcome to this exquisite modern cottage only 12 miles from Hamburg, Stepping inside the a...	3 beds \| 3 baths \| 2,643 sq.ft.	$625,000	Airbnb cash on cash: 2.85% Traditional cash on cash: 2.18% Airbnb Rental Income: $3657 Traditional Rental Income: $2470 Airbnb ROI: 2.85% Traditional ROI: 2.18%
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.	$279,000	Airbnb cash on cash: 8.66% Traditional cash on cash: 4.4% Airbnb Rental Income: $3657 Traditional Rental Income: $1738 Airbnb ROI: 8.66% Traditional ROI: 4.4%
425 Wellington Way Winchester, KY Move in and relax! This beautiful property has been meticulously updated and ready for you...	3 beds \| 3 baths \| 1,727 sq.ft.	$271,900	Airbnb cash on cash: 9.3% Traditional cash on cash: 5.13% Airbnb Rental Income: $3657 Traditional Rental Income: $1788 Airbnb ROI: 9.3% Traditional ROI: 5.13%
2296 Trapp-Goffs Cor Road Winchester, KY At the Last Minute - Buyers Changed their mind! Their loss can be your gain! Property has ...	3 beds \| 2 baths \| 1,680 sq.ft.	$315,000	Airbnb cash on cash: 7.48% Traditional cash on cash: 3.75% Airbnb Rental Income: $3657 Traditional Rental Income: $1755 Airbnb ROI: 7.48% 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: 2.69% Traditional cash on cash: 2.13% Airbnb Rental Income: $2082 Traditional Rental Income: $1365 Airbnb ROI: 2.69% Traditional ROI: 2.13%
427 Alexis Way Winchester, KY Introducing A Stunning Traditional Home with a Rustic Twist just 12 miles from Hamburg Of ...	3 beds \| 4 baths \| 2,199 sq.ft.	$535,000	Airbnb cash on cash: 3.63% Traditional cash on cash: 3.46% Airbnb Rental Income: $3657 Traditional Rental Income: $2772 Airbnb ROI: 3.63% Traditional ROI: 3.46%
162 French Avenue Winchester, KY 162 French Ave, Winchester, Kentucky, is a charming residential property located in a quie...	4 beds \| 1 baths \| 2,327 sq.ft.	$219,000	Airbnb cash on cash: 6.75% Traditional cash on cash: 6.67% Airbnb Rental Income: $2363 Traditional Rental Income: $1763 Airbnb ROI: 6.75% Traditional ROI: 6.67%
374 South Main Street Winchester, KY You must view this adorable remodeled home located in a convenient location, charming, lar...	2 beds \| 1 baths \| 972 sq.ft.	$219,900	Airbnb cash on cash: 5.12% Traditional cash on cash: 3.98% Airbnb Rental Income: $2082 Traditional Rental Income: $1308 Airbnb ROI: 5.12% Traditional ROI: 3.98%
210 Jett Drive Winchester, KY Don't miss out on this wonderful ranch floor plan, New Construction, 3 bedrooms, 2 baths, ...	3 beds \| 2 baths \| 1,600 sq.ft.	$359,900	Airbnb cash on cash: 6.33% Traditional cash on cash: 3.56% Airbnb Rental Income: $3657 Traditional Rental Income: $1923 Airbnb ROI: 6.33% Traditional ROI: 3.56%
206 Jett Drive Winchester, KY New Construction, come view, great house plan, ranch on a crawl space, 3 bedrooms, 2 bath,...	3 beds \| 2 baths \| 1,635 sq.ft.	$369,900	Airbnb cash on cash: 6.5% Traditional cash on cash: 3.81% Airbnb Rental Income: $3657 Traditional Rental Income: $1925 Airbnb ROI: 6.5% Traditional ROI: 3.81%
19 Victory Avenue Winchester, KY Fully renovated in 2023, 3 bed X 2 bath, new landscaping in 2024, includes a basement, det...	3 beds \| 2 baths \| 1,780 sq.ft.	$277,000	Airbnb cash on cash: 9.22% Traditional cash on cash: 6.25% Airbnb Rental Income: $3657 Traditional Rental Income: $2084 Airbnb ROI: 9.22% Traditional ROI: 6.25%
454-500 Trapp Goffs Corner Winchester, KY Imagine a serene 6.54 acre property featuring a recently remodeled 3 bedroom home. The hou...	3 beds \| 1 baths \| 1,160 sq.ft.	$279,000	Airbnb cash on cash: 8.66% Traditional cash on cash: 3.36% Airbnb Rental Income: $3657 Traditional Rental Income: $1465 Airbnb ROI: 8.66% Traditional ROI: 3.36%
1480 White Turley Pike Winchester, KY Charming 3-bedroom, 2-bath home on 5 acres with beautiful views, featuring new flooring th...	3 beds \| 2 baths \| 2,470 sq.ft.	$420,000	Airbnb cash on cash: 5.17% Traditional cash on cash: 4.13% Airbnb Rental Income: $3657 Traditional Rental Income: $2447 Airbnb ROI: 5.17% Traditional ROI: 4.13%
224 3rd Street Winchester, KY New Construction!!!! Let the sun shine in on this 2BR/2BA home. Don't mess with others di...	2 beds \| 2 baths \| 962 sq.ft.	$179,900	Airbnb cash on cash: 6.64% Traditional cash on cash: 6.44% Airbnb Rental Income: $2082 Traditional Rental Income: $1512 Airbnb ROI: 6.64% Traditional ROI: 6.44%
83 Hillcrest Drive Winchester, KY Welcome to this charming ranch home in Winchester, Ky! This cozy abode features 3 bedrooms...	3 beds \| 1 baths \| 2,052 sq.ft.	$257,000	Airbnb cash on cash: 9.55% Traditional cash on cash: 5.02% Airbnb Rental Income: $3657 Traditional Rental Income: $1761 Airbnb ROI: 9.55% Traditional ROI: 5.02%
113 Holiday Road Winchester, KY You must see this lovely brick home on a basement in Holiday Hills! If you like pickleball...	3 beds \| 3 baths \| 2,090 sq.ft.	$349,000	Airbnb cash on cash: 6.98% Traditional cash on cash: 5.19% Airbnb Rental Income: $3657 Traditional Rental Income: $2274 Airbnb ROI: 6.98% Traditional ROI: 5.19%
8481 Old Boonesboro Road Winchester, KY Nestled in the heart of rural Winchester, KY, this charming 2-bedroom, 1-bath home offers ...	2 beds \| 1 baths \| 873 sq.ft.	$175,000	Airbnb cash on cash: 7.35% Traditional cash on cash: 5.28% Airbnb Rental Income: $2082 Traditional Rental Income: $1202 Airbnb ROI: 7.35% Traditional ROI: 5.28%
2925 Irvine Road Winchester, KY Welcome to 2925 Irvine Rd in Winchester, KY! This stunning farm boasts 10 acres of beautif...	3 beds \| 2 baths \| 1,680 sq.ft.	$260,000	Airbnb cash on cash: 9.9% Traditional cash on cash: 6.07% Airbnb Rental Income: $3657 Traditional Rental Income: $1919 Airbnb ROI: 9.9% Traditional ROI: 6.07%
4640 Ecton Road Winchester, KY Beautiful home with wonderful views of the countryside. Large kitchen with granite counte...	3 beds \| 2 baths \| 1,802 sq.ft.	$435,000	Airbnb cash on cash: 5.22% Traditional cash on cash: 3.31% Airbnb Rental Income: $3657 Traditional Rental Income: $2081 Airbnb ROI: 5.22% Traditional ROI: 3.31%
309 Gallahadion Court Winchester, KY This beautiful home located in desirable Fairholme Estates is a must see!! Amazing open fl...	3 beds \| 3 baths \| 1,920 sq.ft.	$432,000	Airbnb cash on cash: 5.8% Traditional cash on cash: 4.5% Airbnb Rental Income: $3657 Traditional Rental Income: $2332 Airbnb ROI: 5.8% Traditional ROI: 4.5%
311 Gallahadion Court Winchester, KY This beautiful ranch home located in desirable Fairholme Estates is a must see!! Amazing o...	3 beds \| 2 baths \| 1,612 sq.ft.	$389,700	Airbnb cash on cash: 6.53% Traditional cash on cash: 3.98% Airbnb Rental Income: $3657 Traditional Rental Income: $1927 Airbnb ROI: 6.53% Traditional ROI: 3.98%
7 Pocahontas Trail Winchester, KY Marvelous raised ranch home with an oversized two car garage and a partially finished base...	2 beds \| 1 baths \| 1,626 sq.ft.	$185,000	Airbnb cash on cash: 6.96% Traditional cash on cash: 6.47% Airbnb Rental Income: $2082 Traditional Rental Income: $1460 Airbnb ROI: 6.96% Traditional ROI: 6.47%
619 Westmeade Drive Winchester, KY Great 3 bedroom, 2 bath home on extra large lot. Wonderfully maintained. Detached 2-car ...	3 beds \| 2 baths \| 1,629 sq.ft.	$259,900	Airbnb cash on cash: 9.91% Traditional cash on cash: 6.09% Airbnb Rental Income: $3657 Traditional Rental Income: $1922 Airbnb ROI: 9.91% Traditional ROI: 6.09%
22 Fontaine Boulevard Winchester, KY Experience the best of modern living in this executive home, featuring a beautifully renov...	3 beds \| 3 baths \| 2,200 sq.ft.	$395,000	Airbnb cash on cash: 5.96% Traditional cash on cash: 4.44% Airbnb Rental Income: $3657 Traditional Rental Income: $2293 Airbnb ROI: 5.96% Traditional ROI: 4.44%
216 Orchid Court Winchester, KY Welcome to this charming and well-kept brick and vinyl home, nestled on a peaceful cul-de-...	3 beds \| 3 baths \| 1,922 sq.ft.	$310,000	Airbnb cash on cash: 7.96% Traditional cash on cash: 5.54% Airbnb Rental Income: $3657 Traditional Rental Income: $2153 Airbnb ROI: 7.96% Traditional ROI: 5.54%
358 Crescent Avenue Winchester, KY Located in the sought-after Thomson Addition neighborhood, this 2-bedroom, 1-bathroom hous...	2 beds \| 1 baths \| 1,764 sq.ft.	$224,900	Airbnb cash on cash: 5.25% Traditional cash on cash: 4.52% Airbnb Rental Income: $2082 Traditional Rental Income: $1392 Airbnb ROI: 5.25% Traditional ROI: 4.52%

Vacation Rentals in Winchester

There are 35 vacation rental properties available for sale in the city of Winchester . The median list price of Airbnb properties available for sale in Winchester is $275,000 and the average price per square foot is $129. The cash on cash return on vacation rentals in Winchester is 7.00%. The average monthly short term rental income in Winchester is $3,657.

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

There are 35 Airbnb properties available for sale in Winchester.

In 2024, the best neighborhood to buy short term rental property is Winchester.

In November 2024, the average Airbnb occupancy rate in Winchester is 58%.

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

502 Hewlett Court

Winchester, KY

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

$345,000

Airbnb cash on cash: 6.68%

Traditional cash on cash: 5.13%

Airbnb Rental Income: $3657

Traditional Rental Income: $2357

Airbnb ROI: 6.68%

Traditional ROI: 5.13%

42 Mockingbird Valley Road

Winchester, KY

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

$465,000

Airbnb cash on cash: 4.5%

Traditional cash on cash: 3.42%

Airbnb Rental Income: $3657

Traditional Rental Income: $2386

Airbnb ROI: 4.5%

Traditional ROI: 3.42%

112 Sycamore Street

Winchester, KY

4 beds | 2 baths | 1,380 sq.ft.

$175,000

Airbnb cash on cash: 8.27%

Traditional cash on cash: 7.87%

Airbnb Rental Income: $2363

Traditional Rental Income: $1713

Airbnb ROI: 8.27%

Traditional ROI: 7.87%

2482 Mina Station Road

Winchester, KY

3 beds | 2 baths | 1,756 sq.ft.

$310,000

Airbnb cash on cash: 7.63%

Traditional cash on cash: 3.72%

Airbnb Rental Income: $3657

Traditional Rental Income: $1719

Airbnb ROI: 7.63%

Traditional ROI: 3.72%

509 Lasalle Court

Winchester, KY

3 beds | 3 baths | 2,484 sq.ft.

$308,000

Airbnb cash on cash: 7.69%

Traditional cash on cash: 6.29%

Airbnb Rental Income: $3657

Traditional Rental Income: $2454

Airbnb ROI: 7.69%

Traditional ROI: 6.29%

122 Buckingham Lane

Winchester, KY

3 beds | 2 baths | 1,240 sq.ft.

$280,000

Airbnb cash on cash: 8.63%

Traditional cash on cash: 2.84%

Airbnb Rental Income: $3657

Traditional Rental Income: $1331

Airbnb ROI: 8.63%

Traditional ROI: 2.84%

440 Flanagan Station Road

Winchester, KY

3 beds | 3 baths | 2,620 sq.ft.

$525,000

Airbnb cash on cash: 3.78%

Traditional cash on cash: 2.97%

Airbnb Rental Income: $3657

Traditional Rental Income: $2461

Airbnb ROI: 3.78%

Traditional ROI: 2.97%

209 Robyn Drive

Winchester, KY

3 beds | 3 baths | 1,825 sq.ft.

$275,000

Airbnb cash on cash: 8.81%

Traditional cash on cash: 5.16%

Airbnb Rental Income: $3657

Traditional Rental Income: $1910

Airbnb ROI: 8.81%