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
724 Terry Drive Winchester, KY Charming Split-Level Home in a Peaceful Winchester Neighborhood Discover this beautiful 3-...	3 beds \| 2 baths \| 2,250 sq.ft.	$279,500	Airbnb cash on cash: N/A Traditional cash on cash: 6% Airbnb Rental Income: $null Traditional Rental Income: $2162 Airbnb ROI: N/A Traditional ROI: 6%
213 Hood Avenue Winchester, KY This newly updated 4-bedroom home with lots of character sits in an established neighborho...	4 beds \| N/A baths \| 2,244 sq.ft.	$361,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.14% Airbnb Rental Income: $null Traditional Rental Income: $2464 Airbnb ROI: N/A Traditional ROI: 5.14%
508 Boone Avenue Winchester, KY 3 bedroom, 2 1/2 bath brick home in Witherspoon Subdivision. New roof, new freeze resistan...	3 beds \| N/A baths \| 2,868 sq.ft.	$350,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.13% Airbnb Rental Income: $null Traditional Rental Income: $2717 Airbnb ROI: N/A Traditional ROI: 6.13%
410 Corinne Court Winchester, KY Charming Ranch-Style Home with Lots of Room- Step inside this 8 year old beautiful 1,604 s...	3 beds \| 2 baths \| 1,604 sq.ft.	$330,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.78% Airbnb Rental Income: $null Traditional Rental Income: $1532 Airbnb ROI: N/A Traditional ROI: 2.78%
118 Windridge Drive Winchester, KY Located in the Windridge neighborhood with easy access to both Bypass Rd and Boone Ave, th...	3 beds \| 2 baths \| 1,617 sq.ft.	$325,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.83% Airbnb Rental Income: $null Traditional Rental Income: $1829 Airbnb ROI: N/A Traditional ROI: 3.83%
223 Bartram Court Winchester, KY Incredible value in the highly desirable Oakmont subdivision! This completely remodeled 3 ...	3 beds \| N/A baths \| 1,606 sq.ft.	$289,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.93% Airbnb Rental Income: $null Traditional Rental Income: $1886 Airbnb ROI: N/A Traditional ROI: 4.93%
300 Calmes Boulevard Winchester, KY Gorgeous & Spacious 4BR/2.5BA Home in Calmes Estates Welcome to your dream home in the hig...	3 beds \| 3 baths \| 2,068 sq.ft.	$399,717	Airbnb cash on cash: N/A Traditional cash on cash: 3.02% Airbnb Rental Income: $null Traditional Rental Income: $1919 Airbnb ROI: N/A Traditional ROI: 3.02%
363 S Main Street Winchester, KY Built in the 1940s, this 3-bedroom, 2-bath home blends timeless character with thoughtful ...	3 beds \| 2 baths \| 2,142 sq.ft.	$225,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.05% Airbnb Rental Income: $null Traditional Rental Income: $2201 Airbnb ROI: N/A Traditional ROI: 8.05%
213 Orchid Court Winchester, KY	4 beds \| 3 baths \| 1,776 sq.ft.	$339,999	Airbnb cash on cash: N/A Traditional cash on cash: 4.39% Airbnb Rental Income: $null Traditional Rental Income: $2088 Airbnb ROI: N/A Traditional ROI: 4.39%
306 Snowden Drive Winchester, KY Home is quietly nestled within the Wesleyan Park subdivision just off the Winchester Bypas...	4 beds \| 2 baths \| 1,593 sq.ft.	$252,500	Airbnb cash on cash: N/A Traditional cash on cash: 5.78% Airbnb Rental Income: $null Traditional Rental Income: $1912 Airbnb ROI: N/A Traditional ROI: 5.78%
203 Inverness Lane Winchester, KY At 203 Inverness Lane, life feels a little easier. Set on a corner lot at the entry of a q...	3 beds \| 3 baths \| 1,935 sq.ft.	$245,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.69% Airbnb Rental Income: $null Traditional Rental Income: $2071 Airbnb ROI: N/A Traditional ROI: 6.69%
407 Corinne Court Winchester, KY Welcome to 407 Corinne Court a beautifully maintained 3-bedroom, 2-bath all-electric home ...	3 beds \| 2 baths \| 1,352 sq.ft.	$300,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.63% Airbnb Rental Income: $null Traditional Rental Income: $1924 Airbnb ROI: N/A Traditional ROI: 4.63%
59 Holiday Road Winchester, KY NEW PRICE! With limited inventory on the market, don't wait too long to view this brick ra...	3 beds \| 1 baths \| 1,050 sq.ft.	$219,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.06% Airbnb Rental Income: $null Traditional Rental Income: $1258 Airbnb ROI: N/A Traditional ROI: 4.06%
388 Colby Ridge Boulevard Winchester, KY Need to see inside of this one! Seller bought in May 2021. Remodeled kitchen. Removed one ...	3 beds \| N/A baths \| 1,224 sq.ft.	$215,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.02% Airbnb Rental Income: $null Traditional Rental Income: $1697 Airbnb ROI: N/A Traditional ROI: 6.02%
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.	$199,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.81% Airbnb Rental Income: $null Traditional Rental Income: $1387 Airbnb ROI: N/A Traditional ROI: 5.81%
42 Mockingbird Valley Road Winchester, KY The term 'Move In Ready' really and truly applies here at 42 Mockingbird Valley Road! Vers...	3 beds \| N/A baths \| 2,961 sq.ft.	$457,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.5% Airbnb Rental Income: $null Traditional Rental Income: $2386 Airbnb ROI: N/A Traditional ROI: 3.5%
103 Mayfair Court Winchester, KY This well-maintained ranch offers 3 bedrooms, 2 full baths, and a 3-car garage that's insu...	3 beds \| 2 baths \| 1,485 sq.ft.	$350,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.67% Airbnb Rental Income: $null Traditional Rental Income: $1910 Airbnb ROI: N/A Traditional ROI: 3.67%
130 Hibiscus Lane Winchester, KY This beautiful 4 bedroom, 2.5 bath home offers a spacious and thoughtful layout with the p...	4 beds \| N/A baths \| 1,900 sq.ft.	$350,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.64% Airbnb Rental Income: $null Traditional Rental Income: $1772 Airbnb ROI: N/A Traditional ROI: 3.64%
5705 Mount Sterling Road Winchester, KY The one you've been waiting for. This beautiful home has so much to offer. 4 bedrooms, 2 1...	4 beds \| 3 baths \| 2,980 sq.ft.	$389,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.43% Airbnb Rental Income: $null Traditional Rental Income: $2749 Airbnb ROI: N/A Traditional ROI: 5.43%
6 Monroe Avenue Winchester, KY Charming and Updated Home in the Heart of Winchester! Welcome to 6 Monroe Ave - a beautifu...	3 beds \| 2 baths \| 1,305 sq.ft.	$187,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.41% Airbnb Rental Income: $null Traditional Rental Income: $1740 Airbnb ROI: N/A Traditional ROI: 7.41%
17 Euclid Avenue Winchester, KY Welcome to 17 Euclid Ave, a charming two-story home in the heart of Winchester! This beaut...	3 beds \| 2 baths \| 1,656 sq.ft.	$249,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.87% Airbnb Rental Income: $null Traditional Rental Income: $1443 Airbnb ROI: N/A Traditional ROI: 3.87%
408 Corinne Court Winchester, KY Come see this immaculate 3 bedroom, 2 bath single-story ranch with an open-concept split b...	3 beds \| 2 baths \| 1,604 sq.ft.	$394,999	Airbnb cash on cash: N/A Traditional cash on cash: 3.79% Airbnb Rental Income: $null Traditional Rental Income: $1883 Airbnb ROI: N/A Traditional ROI: 3.79%
113 Olde Potomac Avenue Winchester, KY This phenomenal property has had so many updates including the addition of a full bath on ...	3 beds \| 2 baths \| 1,928 sq.ft.	$269,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.13% Airbnb Rental Income: $null Traditional Rental Income: $2119 Airbnb ROI: N/A Traditional ROI: 6.13%
165 Hilltop Drive Winchester, KY This stunning property is ideally located and is an absolute must see! This lovely home is...	3 beds \| 2 baths \| 1,454 sq.ft.	$274,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.76% Airbnb Rental Income: $null Traditional Rental Income: $1856 Airbnb ROI: N/A Traditional ROI: 5.76%
2317 Muddy Creek Road Winchester, KY Want a home with a couple of acres close to town? Then this one is for you! Located just o...	2 beds \| 1 baths \| 1,046 sq.ft.	$169,000	Airbnb cash on cash: 0.21% Traditional cash on cash: 5.35% Airbnb Rental Income: $737 Traditional Rental Income: $1253 Airbnb ROI: 0.21% Traditional ROI: 5.35%
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: N/A Traditional cash on cash: 6.87% Airbnb Rental Income: $null Traditional Rental Income: $1494 Airbnb ROI: N/A Traditional ROI: 6.87%
446 Tremont Lane Winchester, KY Agent is Seller. 2800 square feet with four bedrooms and 2-1/2 baths. A large corner lot w...	4 beds \| N/A baths \| 2,811 sq.ft.	$369,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.54% Airbnb Rental Income: $null Traditional Rental Income: $1961 Airbnb ROI: N/A Traditional ROI: 3.54%
160 Agawam Road Winchester, KY Welcome to this beautifully maintained brick ranch home set on a spacious and private 5-ac...	3 beds \| N/A baths \| 4,933 sq.ft.	$524,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.35% Airbnb Rental Income: $null Traditional Rental Income: $2151 Airbnb ROI: N/A Traditional ROI: 2.35%
202 dubuy Drive Winchester, KY Welcome to this move-in ready 3-bedroom, 2.5-bath home built in 2022. With 1,745 sq. ft., ...	3 beds \| N/A baths \| 1,800 sq.ft.	$309,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.22% Airbnb Rental Income: $null Traditional Rental Income: $2150 Airbnb ROI: N/A Traditional ROI: 5.22%
424 Alexis Way Winchester, KY Introducing the Castleton, a stunning home designed to impress in the sought-after Mallard...	3 beds \| N/A 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%
1701 Gay Evans Road Winchester, KY Back on the market with UPDATES! Come see for yourself! 4bds with 2 BONUS ROOMS!! Your dre...	4 beds \| N/A baths \| 4,345 sq.ft.	$844,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.16% Airbnb Rental Income: $null Traditional Rental Income: $3249 Airbnb ROI: N/A Traditional ROI: 2.16%
313 Snowden Drive Winchester, KY This charming mid-century home was completely renovated in 2022 and has been beautifully m...	3 beds \| 1 baths \| 1,232 sq.ft.	$239,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.61% Airbnb Rental Income: $null Traditional Rental Income: $1559 Airbnb ROI: N/A Traditional ROI: 4.61%
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.	$824,900	Airbnb cash on cash: N/A Traditional cash on cash: 1.31% Airbnb Rental Income: $null Traditional Rental Income: $2523 Airbnb ROI: N/A Traditional ROI: 1.31%
420 Alexis Way Winchester, KY Check out 420 Alexis Way in Winchester! This stunning home features a beautiful great room...	4 beds \| N/A baths \| 2,770 sq.ft.	$674,500	Airbnb cash on cash: N/A Traditional cash on cash: 2.43% Airbnb Rental Income: $null Traditional Rental Income: $2823 Airbnb ROI: N/A Traditional ROI: 2.43%
209 Allan Place Winchester, KY Charming 3 Bedroom Home with Vaulted Ceilings and Wooded Views Welcome to this inviting 3-...	3 beds \| 2 baths \| 1,260 sq.ft.	$234,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.29% Airbnb Rental Income: $null Traditional Rental Income: $1674 Airbnb ROI: N/A Traditional ROI: 5.29%
20 Bon-Haven Avenue Winchester, KY Welcome to 20 Bon Haven Avenue, a beautifully renovated 4-bedroom, 3 full bathroom home id...	4 beds \| 3 baths \| 1,850 sq.ft.	$289,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.92% Airbnb Rental Income: $null Traditional Rental Income: $2754 Airbnb ROI: N/A Traditional ROI: 7.92%
175 Waterworks Road Winchester, KY The country house you have been looking for! 3 bed, 2 bath with an amazing front porch whe...	3 beds \| 2 baths \| 1,295 sq.ft.	$250,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.54% Airbnb Rental Income: $null Traditional Rental Income: $1269 Airbnb ROI: N/A Traditional ROI: 3.54%
670 Lillies Ferry Road Winchester, KY Escape to this serene and private 12+ acre property, boasting a 3BR/2BA home sitting on a ...	3 beds \| 2 baths \| 2,053 sq.ft.	$580,000	Airbnb cash on cash: N/A Traditional cash on cash: 1% Airbnb Rental Income: $null Traditional Rental Income: $1316 Airbnb ROI: N/A Traditional ROI: 1%
221 S Highland Street Winchester, KY INVESTOR SPECIAL, could be a great option for an end of year cost seg study and bonus depr...	5 beds \| 3 baths \| 3,007 sq.ft.	$269,900	Airbnb cash on cash: N/A Traditional cash on cash: 7.27% Airbnb Rental Income: $null Traditional Rental Income: $2277 Airbnb ROI: N/A Traditional ROI: 7.27%
1857 Ironworks Road Winchester, KY Get a piece of Bluegrass heaven in this move-in ready modern farmhouse on just under 5acre...	5 beds \| N/A baths \| 2,924 sq.ft.	$429,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.9% Airbnb Rental Income: $null Traditional Rental Income: $2001 Airbnb ROI: N/A Traditional ROI: 2.9%

Real Estate investment in Winchester, KY

There are 159 properties for sale in the city of Winchester . The median list price in Winchester is $339,999 and the average price per square foot is $134. In November 2025, the average monthly cash on cash return in Winchester is 5.00%. The average monthly rental income in Winchester is $2,004.

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

There are 159 investment properties available for sale in Winchester.

In 2025, the best neighborhood to buy investment property is Winchester.

The ROI for Short-Term is higher than the Long-Term in Winchester with average rental income of $737.

Your search for investment property begins and ends here

Investment Property for Sale in Winchester, KY

724 Terry Drive

Winchester, KY

3 beds | 2 baths | 2,250 sq.ft.

$279,500

Airbnb cash on cash: N/A

Traditional cash on cash: 6%

Airbnb Rental Income: $null

Traditional Rental Income: $2162

Airbnb ROI: N/A

Traditional ROI: 6%

213 Hood Avenue

Winchester, KY

4 beds | N/A baths | 2,244 sq.ft.

$361,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.14%

Airbnb Rental Income: $null

Traditional Rental Income: $2464

Airbnb ROI: N/A

Traditional ROI: 5.14%

508 Boone Avenue

Winchester, KY

3 beds | N/A baths | 2,868 sq.ft.

$350,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.13%

Airbnb Rental Income: $null

Traditional Rental Income: $2717

Airbnb ROI: N/A

Traditional ROI: 6.13%

410 Corinne Court

Winchester, KY

3 beds | 2 baths | 1,604 sq.ft.

$330,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.78%

Airbnb Rental Income: $null

Traditional Rental Income: $1532

Airbnb ROI: N/A

Traditional ROI: 2.78%

118 Windridge Drive

Winchester, KY

3 beds | 2 baths | 1,617 sq.ft.

$325,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.83%

Airbnb Rental Income: $null

Traditional Rental Income: $1829

Airbnb ROI: N/A

Traditional ROI: 3.83%

223 Bartram Court

Winchester, KY

3 beds | N/A baths | 1,606 sq.ft.

$289,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.93%

Airbnb Rental Income: $null

Traditional Rental Income: $1886

Airbnb ROI: N/A

Traditional ROI: 4.93%

300 Calmes Boulevard

Winchester, KY

3 beds | 3 baths | 2,068 sq.ft.

$399,717

Airbnb cash on cash: N/A

Traditional cash on cash: 3.02%

Airbnb Rental Income: $null

Traditional Rental Income: $1919

Airbnb ROI: N/A

Traditional ROI: 3.02%

363 S Main Street

Winchester, KY

3 beds | 2 baths | 2,142 sq.ft.

$225,000

Airbnb cash on cash: N/A

Traditional cash on cash: 8.05%

Airbnb Rental Income: $null

Traditional Rental Income: $2201

Airbnb ROI: N/A