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
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: 2.43% Traditional cash on cash: 4.24% Airbnb Rental Income: $1600 Traditional Rental Income: $1588 Airbnb ROI: 2.43% Traditional ROI: 4.24%
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.	$345,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.01% Airbnb Rental Income: $null Traditional Rental Income: $2964 Airbnb ROI: N/A Traditional ROI: 7.01%
118 Windridge Drive Winchester, KY Enjoy rest, relaxation and all the outdoor activities you can dream up with this home. Coz...	3 beds \| 2 baths \| 1,617 sq.ft.	$307,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.14% Airbnb Rental Income: $null Traditional Rental Income: $1829 Airbnb ROI: N/A Traditional ROI: 4.14%
618 Westmeade Drive Winchester, KY Conveniently located, this charming well kept home features a functional floorplan offerin...	4 beds \| 2 baths \| 2,116 sq.ft.	$296,900	Airbnb cash on cash: 1.91% Traditional cash on cash: 6.04% Airbnb Rental Income: $1600 Traditional Rental Income: $2301 Airbnb ROI: 1.91% Traditional ROI: 6.04%
720 Terry Drive Winchester, KY Welcome home to this beautifully refreshed 3-bedroom, 2-bath property located in the heart...	3 beds \| 2 baths \| 1,779 sq.ft.	$275,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.63% Airbnb Rental Income: $null Traditional Rental Income: $2033 Airbnb ROI: N/A Traditional ROI: 5.63%
363 S Main Street Winchester, KY Back on Market! Welcome to 363 South Main Street in the heart of downtown Winchester, KY-t...	3 beds \| 2 baths \| 2,142 sq.ft.	$250,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.08% Airbnb Rental Income: $null Traditional Rental Income: $2201 Airbnb ROI: N/A Traditional ROI: 7.08%
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: N/A Traditional cash on cash: 6.08% Airbnb Rental Income: $null Traditional Rental Income: $1613 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 7.95% Airbnb Rental Income: $null Traditional Rental Income: $1722 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 4.29% Airbnb Rental Income: $null Traditional Rental Income: $1258 Airbnb ROI: N/A Traditional ROI: 4.29%
34 Hays Street Winchester, KY This spacious 4-bedroom bungalow is tucked away in downtown Winchester in a great walkable...	4 beds \| 2 baths \| 2,450 sq.ft.	$210,000	Airbnb cash on cash: 3.98% Traditional cash on cash: 9.81% Airbnb Rental Income: $1600 Traditional Rental Income: $2304 Airbnb ROI: 3.98% Traditional ROI: 9.81%
310 Essex Court Winchester, KY Welcome home to this charming and spacious 2-bedroom, 2.5-bath townhome perfectly situated...	2 beds \| 3 baths \| 1,188 sq.ft.	$192,500	Airbnb cash on cash: 2.29% Traditional cash on cash: 7.13% Airbnb Rental Income: $1077 Traditional Rental Income: $1594 Airbnb ROI: 2.29% Traditional ROI: 7.13%
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.	$179,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.55% Airbnb Rental Income: $null Traditional Rental Income: $1387 Airbnb ROI: N/A Traditional ROI: 6.55%
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.	$445,500	Airbnb cash on cash: N/A Traditional cash on cash: 3.64% Airbnb Rental Income: $null Traditional Rental Income: $2386 Airbnb ROI: N/A Traditional ROI: 3.64%
28 Churchill Drive Winchester, KY *Motivated Sellers* Beautifully updated ranch on a new, fully finished walk out baseme...	5 beds \| 3 baths \| 2,624 sq.ft.	$320,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.67% Airbnb Rental Income: $null Traditional Rental Income: $2657 Airbnb ROI: N/A Traditional ROI: 6.67%
327 Newcastle Lane Winchester, KY Seller is offering $2000 total towards buyers concession (can be used for downpayment, pre...	4 beds \| 3 baths \| 1,693 sq.ft.	$294,900	Airbnb cash on cash: 2.71% Traditional cash on cash: 5.39% Airbnb Rental Income: $1600 Traditional Rental Income: $1887 Airbnb ROI: 2.71% Traditional ROI: 5.39%
905 Pretty Run Road Winchester, KY Welcome to this elevated farmhouse classic-refined yet unpretentious, elegant yet entirely...	3 beds \| 4 baths \| 3,391 sq.ft.	$600,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.64% Airbnb Rental Income: $null Traditional Rental Income: $3173 Airbnb ROI: N/A Traditional ROI: 3.64%
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: N/A Traditional cash on cash: 6.46% Airbnb Rental Income: $null Traditional Rental Income: $1663 Airbnb ROI: N/A Traditional ROI: 6.46%
215 Old Log Lick Road Winchester, KY Price drop plus Seller will credit Buyer $1,000 for carpet repair/replacement. Enjoy where...	3 beds \| 2 baths \| 1,450 sq.ft.	$325,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.48% Airbnb Rental Income: $null Traditional Rental Income: $1724 Airbnb ROI: N/A Traditional ROI: 3.48%
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: N/A Traditional cash on cash: 3.87% Airbnb Rental Income: $null Traditional Rental Income: $1443 Airbnb ROI: N/A Traditional ROI: 3.87%
54 Locust Drive Winchester, KY Opportunity awaits at 54 Locust Drive in Wesleyan Park subdivision. This all-brick ranch o...	3 beds \| 2 baths \| 1,692 sq.ft.	$299,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.42% Airbnb Rental Income: $null Traditional Rental Income: $1859 Airbnb ROI: N/A Traditional ROI: 4.42%
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: N/A Traditional cash on cash: 4.23% Airbnb Rental Income: $null Traditional Rental Income: $2464 Airbnb ROI: N/A Traditional ROI: 4.23%
192 Prescott Lane Winchester, KY Welcome to this lovely move in ready gem. Perfectly positioned just off the Winchester Byp...	3 beds \| 3 baths \| 1,550 sq.ft.	$275,000	Airbnb cash on cash: N/A Traditional cash on cash: 6% Airbnb Rental Income: $null Traditional Rental Income: $1929 Airbnb ROI: N/A Traditional ROI: 6%
148 W Lexington Avenue Winchester, KY Located in the heart of Winchester, this spacious and versatile two-story home offers incr...	5 beds \| 2 baths \| 2,570 sq.ft.	$229,900	Airbnb cash on cash: N/A Traditional cash on cash: 9.1% Airbnb Rental Income: $null Traditional Rental Income: $2299 Airbnb ROI: N/A Traditional ROI: 9.1%
110 Powe Drive Winchester, KY This 4 Bedroom, 3 Bath home is quietly nestled within the Greenfield subdivision. Prime lo...	4 beds \| 3 baths \| 2,010 sq.ft.	$339,900	Airbnb cash on cash: 2.22% Traditional cash on cash: 5.52% Airbnb Rental Income: $1600 Traditional Rental Income: $2198 Airbnb ROI: 2.22% Traditional ROI: 5.52%
614 Colby Ridge Boulevard Winchester, KY Welcome to this beautifully maintained 4 bed 2.5 bath home built in 2020 offering the perf...	4 beds \| 3 baths \| 2,100 sq.ft.	$359,900	Airbnb cash on cash: 2.1% Traditional cash on cash: 6.49% Airbnb Rental Income: $1600 Traditional Rental Income: $2629 Airbnb ROI: 2.1% Traditional ROI: 6.49%
60 Hiawatha Trail Winchester, KY Updated, affordable, and ready for you! This 3-bedroom, 1-bath home offers approximately 1...	3 beds \| 1 baths \| 1,290 sq.ft.	$204,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.12% Airbnb Rental Income: $null Traditional Rental Income: $1491 Airbnb ROI: N/A Traditional ROI: 6.12%
265 S Highland Street Winchester, KY Great investment opportunity in downtown Winchester! This spacious quadplex has been updat...	8 beds \| 4 baths \| 5,058 sq.ft.	$479,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.59% Airbnb Rental Income: $null Traditional Rental Income: $3505 Airbnb ROI: N/A Traditional ROI: 6.59%
1480 Irvine Road Winchester, KY Beautifully remodeled farmhouse on 10 fenced acres! This 3 bedroom, 3.5 bath home with a f...	3 beds \| 4 baths \| 3,388 sq.ft.	$719,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.94% Airbnb Rental Income: $null Traditional Rental Income: $3588 Airbnb ROI: N/A Traditional ROI: 3.94%
414 Pueblo Court Winchester, KY Turn-key and beautifully designed, this Craftsman-style 2-story home offers the perfect bl...	3 beds \| 3 baths \| 2,648 sq.ft.	$329,999	Airbnb cash on cash: N/A Traditional cash on cash: 6.22% Airbnb Rental Income: $null Traditional Rental Income: $2598 Airbnb ROI: N/A Traditional ROI: 6.22%
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%
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.	$249,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.64% Airbnb Rental Income: $null Traditional Rental Income: $1390 Airbnb ROI: N/A Traditional ROI: 3.64%
47 Buckner Street Winchester, KY This 3-bedroom, 2 full bath home is nestled in a convenient location and ready for new own...	3 beds \| 2 baths \| 1,635 sq.ft.	$174,900	Airbnb cash on cash: N/A Traditional cash on cash: 7.05% Airbnb Rental Income: $null Traditional Rental Income: $1576 Airbnb ROI: N/A Traditional ROI: 7.05%
37 Ashland Avenue Winchester, KY Ideal for first-time buyers, downsizers, or investors. This move-in ready 2-bedroom home f...	2 beds \| 1 baths \| 904 sq.ft.	$139,000	Airbnb cash on cash: 2.76% Traditional cash on cash: 5.6% Airbnb Rental Income: $1077 Traditional Rental Income: $1087 Airbnb ROI: 2.76% Traditional ROI: 5.6%
200 Dubuy Drive Winchester, KY Search no more your dream home just hit the market! You will fall in love with this one as...	3 beds \| 3 baths \| 1,858 sq.ft.	$312,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.14% Airbnb Rental Income: $null Traditional Rental Income: $1853 Airbnb ROI: N/A Traditional ROI: 4.14%
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: N/A Traditional cash on cash: 5.17% Airbnb Rental Income: $null Traditional Rental Income: $2238 Airbnb ROI: N/A 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 \| 3 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%
228 Holiday Road Winchester, KY Back on the market at no fault of the sellers. Don't miss your chance to own this beautifu...	4 beds \| 2 baths \| 1,843 sq.ft.	$339,900	Airbnb cash on cash: 1.44% Traditional cash on cash: 3.99% Airbnb Rental Income: $1600 Traditional Rental Income: $1961 Airbnb ROI: 1.44% Traditional ROI: 3.99%
110 White Conkwright Road Winchester, KY Brick ranch with 3 upstairs bedrooms and 2 bedrooms in your mother in law suite and full f...	5 beds \| 3 baths \| 3,102 sq.ft.	$550,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.41% Airbnb Rental Income: $null Traditional Rental Income: $2797 Airbnb ROI: N/A Traditional ROI: 3.41%
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.	$327,500	Airbnb cash on cash: N/A Traditional cash on cash: 3.22% Airbnb Rental Income: $null Traditional Rental Income: $1555 Airbnb ROI: N/A Traditional ROI: 3.22%
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: N/A Traditional cash on cash: 4.54% Airbnb Rental Income: $null Traditional Rental Income: $1543 Airbnb ROI: N/A Traditional ROI: 4.54%

Real Estate investment in Winchester, KY

There are 163 properties for sale in the city of Winchester . The median list price in Winchester is $295,950 and the average price per square foot is $129. In May 2026, the average monthly cash on cash return in Winchester is 5.00%. The average monthly rental income in Winchester is $1,952.

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

There are 163 investment properties available for sale in Winchester.

In 2026, 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 $1,952.

Your search for investment property begins and ends here

Investment Property for Sale in Winchester, KY

120 Windsor Drive

Winchester, KY

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

$259,900

Airbnb cash on cash: 2.43%

Traditional cash on cash: 4.24%

Airbnb Rental Income: $1600

Traditional Rental Income: $1588

Airbnb ROI: 2.43%

Traditional ROI: 4.24%

221 Moundale Avenue

Winchester, KY

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

$345,000

Airbnb cash on cash: N/A

Traditional cash on cash: 7.01%

Airbnb Rental Income: $null

Traditional Rental Income: $2964

Airbnb ROI: N/A

Traditional ROI: 7.01%

118 Windridge Drive

Winchester, KY

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

$307,900

Airbnb cash on cash: N/A

Traditional cash on cash: 4.14%

Airbnb Rental Income: $null

Traditional Rental Income: $1829

Airbnb ROI: N/A

Traditional ROI: 4.14%

618 Westmeade Drive

Winchester, KY

4 beds | 2 baths | 2,116 sq.ft.

$296,900

Airbnb cash on cash: 1.91%

Traditional cash on cash: 6.04%

Airbnb Rental Income: $1600

Traditional Rental Income: $2301

Airbnb ROI: 1.91%

Traditional ROI: 6.04%

720 Terry Drive

Winchester, KY

3 beds | 2 baths | 1,779 sq.ft.

$275,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.63%

Airbnb Rental Income: $null

Traditional Rental Income: $2033

Airbnb ROI: N/A

Traditional ROI: 5.63%

363 S Main Street

Winchester, KY

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

$250,000

Airbnb cash on cash: N/A

Traditional cash on cash: 7.08%

Airbnb Rental Income: $null

Traditional Rental Income: $2201

Airbnb ROI: N/A

Traditional ROI: 7.08%

128 Bay Hill Drive

Winchester, KY

3 beds | 2 baths | 1,289 sq.ft.

$200,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.08%

Airbnb Rental Income: $null

Traditional Rental Income: $1613

Airbnb ROI: N/A

Traditional ROI: 6.08%

29 Euclid Avenue

Winchester, KY

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

$190,000

Airbnb cash on cash: N/A

Traditional cash on cash: 7.95%

Airbnb Rental Income: $null

Traditional Rental Income: $1722

Airbnb ROI: N/A