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
816 Stratton Lane Winchester, KY Welcome to your dream home! Nestled in an excellent location in Winchester, KY, this charm...	4 beds \| 3 baths \| 3,024 sq.ft.	$250,000	Airbnb cash on cash: 4.03% Traditional cash on cash: 9.42% Airbnb Rental Income: $1966 Traditional Rental Income: $2721 Airbnb ROI: 4.03% Traditional ROI: 9.42%
594 Earlymeade Drive Winchester, KY This stunning 5BR,3BA brick home blends classic charm with modern comfort, all situated in...	5 beds \| 3 baths \| 3,489 sq.ft.	$563,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.05% Airbnb Rental Income: $null Traditional Rental Income: $2670 Airbnb ROI: N/A Traditional ROI: 3.05%
508 Boone Avenue Winchester, KY 3 bedroom, 2 1/2 bath brick home in Witherspoon Subdivision. Full basement with double ...	3 beds \| 3 baths \| 2,868 sq.ft.	$385,000	Airbnb cash on cash: 0.61% Traditional cash on cash: 5.41% Airbnb Rental Income: $1405 Traditional Rental Income: $2717 Airbnb ROI: 0.61% Traditional ROI: 5.41%
314 Hanover Drive Winchester, KY Your search is over with this beautiful 3 bedroom 2 bath home with lots of potential. Ente...	3 beds \| 3 baths \| 1,760 sq.ft.	$299,000	Airbnb cash on cash: 1.31% Traditional cash on cash: 5.49% Airbnb Rental Income: $1405 Traditional Rental Income: $2160 Airbnb ROI: 1.31% Traditional ROI: 5.49%
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.	$335,000	Airbnb cash on cash: 0.97% Traditional cash on cash: 3.66% Airbnb Rental Income: $1405 Traditional Rental Income: $1829 Airbnb ROI: 0.97% Traditional ROI: 3.66%
223 Bartram Court Winchester, KY Incredible value in the highly desirable Oakmont subdivision! This completely remodeled 3 ...	3 beds \| 3 baths \| 1,606 sq.ft.	$289,000	Airbnb cash on cash: 1.61% Traditional cash on cash: 4.93% Airbnb Rental Income: $1405 Traditional Rental Income: $1886 Airbnb ROI: 1.61% Traditional ROI: 4.93%
714 Concord Avenue Winchester, KY This beautiful modern home is conveniently located in the Colby Ridge subdivision with eas...	3 beds \| 3 baths \| 1,750 sq.ft.	$374,900	Airbnb cash on cash: 0.67% Traditional cash on cash: 4.13% Airbnb Rental Income: $1405 Traditional Rental Income: $2197 Airbnb ROI: 0.67% Traditional ROI: 4.13%
363 S Main Street Winchester, KY Seller is offering a $10,000 credit at close with an acceptable offer! Welcome to ...	3 beds \| 2 baths \| 2,142 sq.ft.	$239,000	Airbnb cash on cash: 2.08% Traditional cash on cash: 7.48% Airbnb Rental Income: $1405 Traditional Rental Income: $2201 Airbnb ROI: 2.08% Traditional ROI: 7.48%
946 Pine Ridge Road Winchester, KY Custom country home on 8.07+/- acres!!! 4 bed, 4 bath 2 story on a finished basement! Huge...	4 beds \| 4 baths \| 3,523 sq.ft.	$500,000	Airbnb cash on cash: 1.05% Traditional cash on cash: 4.95% Airbnb Rental Income: $1966 Traditional Rental Income: $3273 Airbnb ROI: 1.05% Traditional ROI: 4.95%
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: 3.84% Traditional cash on cash: 5.78% Airbnb Rental Income: $1966 Traditional Rental Income: $1912 Airbnb ROI: 3.84% Traditional ROI: 5.78%
7934 Ironworks Road Winchester, KY Strategically located, this two story home was built to allow for a nice breeze during hot...	3 beds \| 1 baths \| 1,633 sq.ft.	$295,000	Airbnb cash on cash: 1.35% Traditional cash on cash: 3.25% Airbnb Rental Income: $1405 Traditional Rental Income: $1509 Airbnb ROI: 1.35% Traditional ROI: 3.25%
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: 2.73% Traditional cash on cash: 4.06% Airbnb Rental Income: $1405 Traditional Rental Income: $1258 Airbnb ROI: 2.73% Traditional ROI: 4.06%
2085 Hancock Valley Drive Winchester, KY Spacious 3-Bedroom Home on Nearly 5 Acres in Winchester, KY! Discover country living at i...	3 beds \| 3 baths \| 2,927 sq.ft.	$639,900	Airbnb cash on cash: 0.1% Traditional cash on cash: 1.09% Airbnb Rental Income: $1405 Traditional Rental Income: $1573 Airbnb ROI: 0.1% Traditional ROI: 1.09%
175 Magnolia Street Winchester, KY Two homes on one lot. Informaton in listing is for the home in the front of the lot. Beh...	3 beds \| 1 baths \| 1,046 sq.ft.	$135,000	Airbnb cash on cash: 5.79% Traditional cash on cash: 8.92% Airbnb Rental Income: $1405 Traditional Rental Income: $1387 Airbnb ROI: 5.79% Traditional ROI: 8.92%
307 Blair Avenue Winchester, KY This charming 3-bedroom, 1-bath ranch offers fresh updates throughout, including brand new...	3 beds \| 1 baths \| 1,000 sq.ft.	$179,900	Airbnb cash on cash: 4.11% Traditional cash on cash: 5.9% Airbnb Rental Income: $1405 Traditional Rental Income: $1288 Airbnb ROI: 4.11% Traditional ROI: 5.9%
301 Cabin Creek Heights Winchester, KY Nice, clean, and move in ready! This 3 bedroom, all one level brick ranch sits on a really...	3 beds \| 1 baths \| 1,220 sq.ft.	$225,000	Airbnb cash on cash: 2.54% Traditional cash on cash: 4.81% Airbnb Rental Income: $1405 Traditional Rental Income: $1466 Airbnb ROI: 2.54% Traditional ROI: 4.81%
635 Lisletown Lane Winchester, KY Being sold 'as is' furniture stays with home. Tucked away on a private lane behind a charm...	2 beds \| 2 baths \| 1,628 sq.ft.	$219,000	Airbnb cash on cash: 1.63% Traditional cash on cash: 6.73% Airbnb Rental Income: $1083 Traditional Rental Income: $1771 Airbnb ROI: 1.63% Traditional ROI: 6.73%
3560 Wades Mill Road Winchester, KY Welcome to your future farmette just minutes from town and the highway! With 5 acres offer...	3 beds \| 2 baths \| 1,305 sq.ft.	$359,900	Airbnb cash on cash: 0.78% Traditional cash on cash: 2.85% Airbnb Rental Income: $1405 Traditional Rental Income: $1683 Airbnb ROI: 0.78% Traditional ROI: 2.85%
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.	$399,000	Airbnb cash on cash: 1.77% Traditional cash on cash: 5.25% Airbnb Rental Income: $1966 Traditional Rental Income: $2749 Airbnb ROI: 1.77% Traditional ROI: 5.25%
9 Apache Trail Winchester, KY Beautiful remodeled move-in ready four bedroom, 2 full bath split foyer. Here are some of ...	4 beds \| 2 baths \| 1,750 sq.ft.	$259,900	Airbnb cash on cash: 4.48% Traditional cash on cash: 7.01% Airbnb Rental Income: $1966 Traditional Rental Income: $2070 Airbnb ROI: 4.48% Traditional ROI: 7.01%
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: 1.65% Traditional cash on cash: 6.13% Airbnb Rental Income: $1405 Traditional Rental Income: $2119 Airbnb ROI: 1.65% Traditional ROI: 6.13%
34 N Burns Avenue Winchester, KY Welcome to 34 N Burns Avenue, a classic Winchester home with plenty of charm and thoughtfu...	3 beds \| 2 baths \| 1,500 sq.ft.	$224,900	Airbnb cash on cash: 3.12% Traditional cash on cash: 6.99% Airbnb Rental Income: $1405 Traditional Rental Income: $1805 Airbnb ROI: 3.12% Traditional ROI: 6.99%
160 Agawam Road Winchester, KY Welcome to this beautifully maintained brick ranch home set on a spacious and private 5-ac...	3 beds \| 3 baths \| 4,933 sq.ft.	$550,000	Airbnb cash on cash: -0.12% Traditional cash on cash: 2.15% Airbnb Rental Income: $1405 Traditional Rental Income: $2151 Airbnb ROI: -0.12% Traditional ROI: 2.15%
252 S Highland Street Winchester, KY Beautifully updated 3-bedroom, 2-bath home in the heart of Winchester! Brand-new siding an...	3 beds \| 2 baths \| 1,944 sq.ft.	$249,900	Airbnb cash on cash: 1.91% Traditional cash on cash: 6.74% Airbnb Rental Income: $1405 Traditional Rental Income: $2120 Airbnb ROI: 1.91% Traditional ROI: 6.74%
115 Ashley Drive Winchester, KY Well maintained 3 bedroom 2 bath ranch with a fenced in backyard and 2 car garage on a ver...	3 beds \| 2 baths \| 1,320 sq.ft.	$269,900	Airbnb cash on cash: 1.64% Traditional cash on cash: 2.95% Airbnb Rental Income: $1405 Traditional Rental Income: $1316 Airbnb ROI: 1.64% Traditional ROI: 2.95%
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 \| 3 baths \| 1,800 sq.ft.	$309,000	Airbnb cash on cash: 1.21% Traditional cash on cash: 5.22% Airbnb Rental Income: $1405 Traditional Rental Income: $2150 Airbnb ROI: 1.21% Traditional ROI: 5.22%
1028 W Lexington Avenue Winchester, KY 1028 W Lexington Ave, Winchester, KY 40391 Investor's dream in the heart of Winchester! T...	5 beds \| 4 baths \| N/A	$426,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.49% Airbnb Rental Income: $null Traditional Rental Income: $3823 Airbnb ROI: N/A Traditional ROI: 7.49%
424 Alexis Way Winchester, KY Introducing the Castleton, a stunning home designed to impress in the sought-after Mallard...	3 beds \| 3 baths \| 2,405 sq.ft.	$625,000	Airbnb cash on cash: -0.39% Traditional cash on cash: 1.17% Airbnb Rental Income: $1405 Traditional Rental Income: $1890 Airbnb ROI: -0.39% Traditional ROI: 1.17%
314 Carolina Ave Winchester, KY This beautifully 4-bedroom, 2-bath home sits on a spacious corner lot on a peaceful street...	4 beds \| 2 baths \| 1,800 sq.ft.	$248,000	Airbnb cash on cash: 3.94% Traditional cash on cash: 6.74% Airbnb Rental Income: $1966 Traditional Rental Income: $2106 Airbnb ROI: 3.94% Traditional ROI: 6.74%
410 E Broadway Street Winchester, KY Completely remodeled 4 bedroom, 2.5 bath home located in the heart of downtown Winchester....	4 beds \| 3 baths \| 1,728 sq.ft.	$289,900	Airbnb cash on cash: 3.11% Traditional cash on cash: 5.2% Airbnb Rental Income: $1966 Traditional Rental Income: $2018 Airbnb ROI: 3.11% Traditional ROI: 5.2%
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.	$249,900	Airbnb cash on cash: 1.91% Traditional cash on cash: 4.36% Airbnb Rental Income: $1405 Traditional Rental Income: $1559 Airbnb ROI: 1.91% Traditional ROI: 4.36%
208 Royal Oak Drive Winchester, KY Elegant brick and Stone Beauty in sought-after Royal Oak Subdivision! This stunning 4-bedr...	4 beds \| 3 baths \| 2,593 sq.ft.	$469,900	Airbnb cash on cash: 1.15% Traditional cash on cash: 3.64% Airbnb Rental Income: $1966 Traditional Rental Income: $2546 Airbnb ROI: 1.15% Traditional ROI: 3.64%
420 Alexis Way Winchester, KY Check out 420 Alexis Way in Winchester! This stunning home features a beautiful great room...	4 beds \| 3 baths \| 2,770 sq.ft.	$674,500	Airbnb cash on cash: 0.25% Traditional cash on cash: 2.43% Airbnb Rental Income: $1966 Traditional Rental Income: $2823 Airbnb ROI: 0.25% Traditional ROI: 2.43%
228 Forest Court Winchester, KY This brick ranch style home is located on a quiet cul-de-sac in the residential neighborho...	3 beds \| 1 baths \| 1,053 sq.ft.	$219,900	Airbnb cash on cash: 2.41% Traditional cash on cash: 3.22% Airbnb Rental Income: $1405 Traditional Rental Income: $1149 Airbnb ROI: 2.41% Traditional ROI: 3.22%
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.	$299,000	Airbnb cash on cash: 2.97% Traditional cash on cash: 7.6% Airbnb Rental Income: $1966 Traditional Rental Income: $2754 Airbnb ROI: 2.97% Traditional ROI: 7.6%
310 Sarah Court Winchester, KY Welcome to 310 Sarah Court! This charming 3-bedroom, 2-bath home is move-in ready and loca...	3 beds \| 2 baths \| 1,072 sq.ft.	$213,900	Airbnb cash on cash: 2.89% Traditional cash on cash: 4.36% Airbnb Rental Income: $1405 Traditional Rental Income: $1281 Airbnb ROI: 2.89% Traditional ROI: 4.36%
220 Spring Valley Drive Winchester, KY This beautiful 5 acre property is a rare find! Located on a quiet cul-de-sac just minutes ...	4 beds \| 3 baths \| 3,078 sq.ft.	$399,000	Airbnb cash on cash: 2.22% Traditional cash on cash: 5.61% Airbnb Rental Income: $1966 Traditional Rental Income: $2718 Airbnb ROI: 2.22% Traditional ROI: 5.61%
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.	$650,000	Airbnb cash on cash: 0.24% Traditional cash on cash: 0.79% Airbnb Rental Income: $1405 Traditional Rental Income: $1316 Airbnb ROI: 0.24% Traditional ROI: 0.79%
148 Gibson Way Winchester, KY NEW PRICE! Better Than New Construction!!! This Spacious 4 Bedroom 2 1/2 Bath Home Is M...	4 beds \| 3 baths \| 2,456 sq.ft.	$372,500	Airbnb cash on cash: 2.03% Traditional cash on cash: 3.61% Airbnb Rental Income: $1966 Traditional Rental Income: $2003 Airbnb ROI: 2.03% Traditional ROI: 3.61%
1857 Ironworks Road Winchester, KY Get a piece of Bluegrass heaven in this move-in ready modern farmhouse on just under 5acre...	5 beds \| 3 baths \| 2,924 sq.ft.	$440,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.78% Airbnb Rental Income: $null Traditional Rental Income: $2001 Airbnb ROI: N/A Traditional ROI: 2.78%

Real Estate investment in Winchester, KY

There are 177 properties for sale in the city of Winchester . The median list price in Winchester is $310,988 and the average price per square foot is $123. In September 2025, the average monthly cash on cash return in Winchester is 5.00%. The average monthly rental income in Winchester is $2,037.

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

There are 177 investment properties available for sale in Winchester.

In 2025, 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 $2,037.

Your search for investment property begins and ends here

Investment Property for Sale in Winchester, KY

816 Stratton Lane

Winchester, KY

4 beds | 3 baths | 3,024 sq.ft.

$250,000

Airbnb cash on cash: 4.03%

Traditional cash on cash: 9.42%

Airbnb Rental Income: $1966

Traditional Rental Income: $2721

Airbnb ROI: 4.03%

Traditional ROI: 9.42%

594 Earlymeade Drive

Winchester, KY

5 beds | 3 baths | 3,489 sq.ft.

$563,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.05%

Airbnb Rental Income: $null

Traditional Rental Income: $2670

Airbnb ROI: N/A

Traditional ROI: 3.05%

508 Boone Avenue

Winchester, KY

3 beds | 3 baths | 2,868 sq.ft.

$385,000

Airbnb cash on cash: 0.61%

Traditional cash on cash: 5.41%

Airbnb Rental Income: $1405

Traditional Rental Income: $2717

Airbnb ROI: 0.61%

Traditional ROI: 5.41%

314 Hanover Drive

Winchester, KY

3 beds | 3 baths | 1,760 sq.ft.

$299,000

Airbnb cash on cash: 1.31%

Traditional cash on cash: 5.49%

Airbnb Rental Income: $1405

Traditional Rental Income: $2160

Airbnb ROI: 1.31%

Traditional ROI: 5.49%

118 Windridge Drive

Winchester, KY

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

$335,000

Airbnb cash on cash: 0.97%

Traditional cash on cash: 3.66%

Airbnb Rental Income: $1405

Traditional Rental Income: $1829

Airbnb ROI: 0.97%

Traditional ROI: 3.66%

223 Bartram Court

Winchester, KY

3 beds | 3 baths | 1,606 sq.ft.

$289,000

Airbnb cash on cash: 1.61%

Traditional cash on cash: 4.93%

Airbnb Rental Income: $1405

Traditional Rental Income: $1886

Airbnb ROI: 1.61%

Traditional ROI: 4.93%

714 Concord Avenue

Winchester, KY

3 beds | 3 baths | 1,750 sq.ft.

$374,900

Airbnb cash on cash: 0.67%

Traditional cash on cash: 4.13%

Airbnb Rental Income: $1405

Traditional Rental Income: $2197

Airbnb ROI: 0.67%

Traditional ROI: 4.13%

363 S Main Street

Winchester, KY

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

$239,000

Airbnb cash on cash: 2.08%

Traditional cash on cash: 7.48%

Airbnb Rental Income: $1405

Traditional Rental Income: $2201

Airbnb ROI: 2.08%