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
2395 Becknerville Road Winchester, KY An exceptional offering of refined country living, this stunning 11-acre estate blends pri...	4 beds \| 4 baths \| 3,234 sq.ft.	$849,000	Airbnb cash on cash: -0.71% Traditional cash on cash: 2.49% Airbnb Rental Income: $1423 Traditional Rental Income: $3530 Airbnb ROI: -0.71% Traditional ROI: 2.49%
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: 1.72% Traditional cash on cash: 6% Airbnb Rental Income: $1466 Traditional Rental Income: $2162 Airbnb ROI: 1.72% Traditional ROI: 6%
149 Winn Ave Winchester, KY Welcome to this quad plex income producing property. It is a large lot and the property si...	12 beds \| 4 baths \| 4,010 sq.ft.	$290,000	Airbnb cash on cash: N/A Traditional cash on cash: 11.48% Airbnb Rental Income: $null Traditional Rental Income: $3514 Airbnb ROI: N/A Traditional ROI: 11.48%
300 Calmes Boulevard Winchester, KY Gorgeous & Spacious 3BR/2.5BA Home in Calmes Estates . Welcome to your dream home in the h...	3 beds \| 2 baths \| 2,636 sq.ft.	$379,717	Airbnb cash on cash: 0.79% Traditional cash on cash: 3.27% Airbnb Rental Income: $1466 Traditional Rental Income: $1919 Airbnb ROI: 0.79% Traditional ROI: 3.27%
213 Orchid Court Winchester, KY	4 beds \| 3 baths \| 1,776 sq.ft.	$325,000	Airbnb cash on cash: 1.1% Traditional cash on cash: 4.68% Airbnb Rental Income: $1423 Traditional Rental Income: $2088 Airbnb ROI: 1.1% Traditional ROI: 4.68%
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.	$274,900	Airbnb cash on cash: 1.77% Traditional cash on cash: 5.21% Airbnb Rental Income: $1466 Traditional Rental Income: $1924 Airbnb ROI: 1.77% Traditional ROI: 5.21%
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.	$194,900	Airbnb cash on cash: 4.03% Traditional cash on cash: 5.95% Airbnb Rental Income: $1466 Traditional Rental Income: $1387 Airbnb ROI: 4.03% Traditional ROI: 5.95%
42 Mockingbird Valley Road Winchester, KY This is a perfect home for EVERY season.....enjoy multiple, interior gathering spaces and ...	3 beds \| 2 baths \| 2,961 sq.ft.	$452,500	Airbnb cash on cash: 0.37% Traditional cash on cash: 3.56% Airbnb Rental Income: $1466 Traditional Rental Income: $2386 Airbnb ROI: 0.37% Traditional ROI: 3.56%
142 Sturbridge Lane Winchester, KY All on one level, large master bedroom, HVAC less than 2 years old and upgrades made in th...	3 beds \| 2 baths \| 1,220 sq.ft.	$249,500	Airbnb cash on cash: 2.13% Traditional cash on cash: 4.55% Airbnb Rental Income: $1466 Traditional Rental Income: $1603 Airbnb ROI: 2.13% Traditional ROI: 4.55%
52 Hillcrest Drive Winchester, KY 3-bedroom, 2-bath home located in Winchester featuring a full walk-out basement that adds ...	3 beds \| 2 baths \| 2,050 sq.ft.	$216,000	Airbnb cash on cash: 2.74% Traditional cash on cash: 7.8% Airbnb Rental Income: $1466 Traditional Rental Income: $2068 Airbnb ROI: 2.74% Traditional ROI: 7.8%
114 Magnolia Street Winchester, KY Great opportunity for investors, flippers, or anyone looking for a project with tons of po...	2 beds \| 1 baths \| 910 sq.ft.	$99,000	Airbnb cash on cash: 0.33% Traditional cash on cash: 10.18% Airbnb Rental Income: $590 Traditional Rental Income: $1251 Airbnb ROI: 0.33% Traditional ROI: 10.18%
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.	$175,000	Airbnb cash on cash: 3.79% Traditional cash on cash: 8.03% Airbnb Rental Income: $1466 Traditional Rental Income: $1740 Airbnb ROI: 3.79% Traditional ROI: 8.03%
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: 2.13% Traditional cash on cash: 3.87% Airbnb Rental Income: $1466 Traditional Rental Income: $1443 Airbnb ROI: 2.13% Traditional ROI: 3.87%
233 Cunningham Lane Winchester, KY Mini Farm Alert! This fabulous homestead is located less than 2 miles off the Mountain Par...	3 beds \| 2 baths \| 2,258 sq.ft.	$450,000	Airbnb cash on cash: 0.6% Traditional cash on cash: 4% Airbnb Rental Income: $1466 Traditional Rental Income: $2464 Airbnb ROI: 0.6% Traditional ROI: 4%
106 Gibson Way Winchester, KY This well maintained home offers 3 bedrooms, 2.5 bathrooms and a versatile bonus/flex area...	3 beds \| 2 baths \| 2,064 sq.ft.	$339,000	Airbnb cash on cash: 1.1% Traditional cash on cash: 5.7% Airbnb Rental Income: $1466 Traditional Rental Income: $2498 Airbnb ROI: 1.1% Traditional ROI: 5.7%
417 Mt Vernon Drive Winchester, KY A 3 bedroom 2 bath home with a 2 car garage under 150k? Unbelievable! Start off your new y...	3 beds \| 2 baths \| 1,300 sq.ft.	$145,000	Airbnb cash on cash: 4.11% Traditional cash on cash: 8.33% Airbnb Rental Income: $1466 Traditional Rental Income: $1618 Airbnb ROI: 4.11% Traditional ROI: 8.33%
214 S Burns Avenue Winchester, KY Own a beautifully maintained piece of Winchester, KY history on desirable South Burns Aven...	4 beds \| 2 baths \| 2,116 sq.ft.	$298,000	Airbnb cash on cash: 1.37% Traditional cash on cash: 4% Airbnb Rental Income: $1423 Traditional Rental Income: $1735 Airbnb ROI: 1.37% Traditional ROI: 4%
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: 4% Traditional cash on cash: 6.87% Airbnb Rental Income: $1466 Traditional Rental Income: $1494 Airbnb ROI: 4% Traditional ROI: 6.87%
446 Tremont Lane Winchester, KY Are your ready for a lifestyle change? Do you need more space? How about approximately 280...	4 beds \| 2 baths \| 2,811 sq.ft.	$367,000	Airbnb cash on cash: 0.77% Traditional cash on cash: 3.57% Airbnb Rental Income: $1423 Traditional Rental Income: $1961 Airbnb ROI: 0.77% Traditional ROI: 3.57%
6239 Old Boonesboro Road Winchester, KY Welcome Home to the beautiful country! If you've been looking for quiet, space, and a plac...	4 beds \| 2 baths \| 2,659 sq.ft.	$389,900	Airbnb cash on cash: 0.62% Traditional cash on cash: 4.81% Airbnb Rental Income: $1423 Traditional Rental Income: $2530 Airbnb ROI: 0.62% Traditional ROI: 4.81%
313 Carolina Avenue Winchester, KY A beautiful home waiting on you to come grab it. It has new kitchen cabinets. The owners h...	4 beds \| 2 baths \| 1,855 sq.ft.	$260,000	Airbnb cash on cash: 1.83% Traditional cash on cash: 6.67% Airbnb Rental Income: $1423 Traditional Rental Income: $2184 Airbnb ROI: 1.83% Traditional ROI: 6.67%
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.	$349,900	Airbnb cash on cash: 1.01% Traditional cash on cash: 4.67% Airbnb Rental Income: $1466 Traditional Rental Income: $2238 Airbnb ROI: 1.01% Traditional ROI: 4.67%
424 Alexis Way Winchester, KY Introducing the Castleton, a stunning home designed to impress in the sought-after Mallard...	3 beds \| 2 baths \| 2,405 sq.ft.	$625,000	Airbnb cash on cash: -0.3% Traditional cash on cash: 1.17% Airbnb Rental Income: $1466 Traditional Rental Income: $1890 Airbnb ROI: -0.3% Traditional ROI: 1.17%
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.	$799,900	Airbnb cash on cash: -0.64% Traditional cash on cash: 1.41% Airbnb Rental Income: $1423 Traditional Rental Income: $2523 Airbnb ROI: -0.64% Traditional ROI: 1.41%
314 E Broadway Street Winchester, KY Welcome to this beautifully maintained 3-bedroom, 1-bath ranch offering 1,188 sqft of clas...	3 beds \| 1 baths \| 1,188 sq.ft.	$224,000	Airbnb cash on cash: 2.58% Traditional cash on cash: 3.4% Airbnb Rental Income: $1466 Traditional Rental Income: $1207 Airbnb ROI: 2.58% Traditional ROI: 3.4%
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: 2.39% Traditional cash on cash: 5.29% Airbnb Rental Income: $1466 Traditional Rental Income: $1674 Airbnb ROI: 2.39% 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.	$275,000	Airbnb cash on cash: 1.63% Traditional cash on cash: 8.41% Airbnb Rental Income: $1423 Traditional Rental Income: $2754 Airbnb ROI: 1.63% Traditional ROI: 8.41%
1128-1130 Dale Drive Winchester, KY Duplex. Both units are being sold together. Great income-producing potential. Each side of...	4 beds \| 3 baths \| 2,072 sq.ft.	$355,000	Airbnb cash on cash: 0.86% Traditional cash on cash: 5.14% Airbnb Rental Income: $1423 Traditional Rental Income: $2424 Airbnb ROI: 0.86% Traditional ROI: 5.14%
104 Bella Shae Way Winchester, KY Welcome Home to the Winchester Floor Plan by CP Builders. This elegant ranch home features...	3 beds \| 2 baths \| 2,200 sq.ft.	$591,650	Airbnb cash on cash: -0.19% Traditional cash on cash: 1.87% Airbnb Rental Income: $1466 Traditional Rental Income: $2172 Airbnb ROI: -0.19% Traditional ROI: 1.87%
1700 Cabin Creek Road Winchester, KY The possibilities are endless with this exceptional rural property on 12+/- fully fenced a...	3 beds \| 2 baths \| 2,695 sq.ft.	$775,000	Airbnb cash on cash: 0% Traditional cash on cash: 1.64% Airbnb Rental Income: $1466 Traditional Rental Income: $2218 Airbnb ROI: 0% Traditional ROI: 1.64%
1270 Sewell Shop Road Winchester, KY Country Living with Convenience - 5 Fenced Acres in Winchester, KY Enjoy the perfect blend...	5 beds \| 2 baths \| 1,952 sq.ft.	$365,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.03% Airbnb Rental Income: $null Traditional Rental Income: $2213 Airbnb ROI: N/A Traditional ROI: 5.03%
424 Waycross Drive Winchester, KY 424 Waycross Drive offers more space than you might expect, with a layout designed to give...	4 beds \| 3 baths \| 1,944 sq.ft.	$289,900	Airbnb cash on cash: 1.46% Traditional cash on cash: 2.45% Airbnb Rental Income: $1423 Traditional Rental Income: $1269 Airbnb ROI: 1.46% Traditional ROI: 2.45%
12 Linden Avenue Winchester, KY Cute ranch with easy access to I-64 and downtown Winchester. 3 bedrooms with 2 full baths ...	3 beds \| 2 baths \| 1,050 sq.ft.	$235,000	Airbnb cash on cash: 2.87% Traditional cash on cash: 6.45% Airbnb Rental Income: $1466 Traditional Rental Income: $1828 Airbnb ROI: 2.87% Traditional ROI: 6.45%
221 S Highland Street Winchester, KY INVESTOR SPECIAL, You have the opportunity to purchase a fully occupied tri-plex in the he...	5 beds \| 3 baths \| 3,007 sq.ft.	$248,900	Airbnb cash on cash: N/A Traditional cash on cash: 7.95% Airbnb Rental Income: $null Traditional Rental Income: $2277 Airbnb ROI: N/A Traditional ROI: 7.95%
1857 Ironworks Road Winchester, KY Get a piece of Bluegrass heaven in this move-in ready modern farmhouse on just under 5acre...	5 beds \| 2 baths \| 2,924 sq.ft.	$420,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.99% Airbnb Rental Income: $null Traditional Rental Income: $2001 Airbnb ROI: N/A Traditional ROI: 2.99%
414 Alexis Way Winchester, KY Introducing the Alexis, a stunning all-brick ranch home with incredible curb appeal and a ...	3 beds \| 2 baths \| 2,643 sq.ft.	$665,000	Airbnb cash on cash: -0.39% Traditional cash on cash: 1.92% Airbnb Rental Income: $1466 Traditional Rental Income: $2470 Airbnb ROI: -0.39% Traditional ROI: 1.92%
23 Kittison Drive Winchester, KY ONE-OWNER BRICK RANCH HOME!! Now that I have your attention, schedule a showing quickly, t...	3 beds \| 2 baths \| 1,346 sq.ft.	$235,000	Airbnb cash on cash: 2.38% Traditional cash on cash: 3.63% Airbnb Rental Income: $1466 Traditional Rental Income: $1312 Airbnb ROI: 2.38% Traditional ROI: 3.63%
188 Big Stoner Road Winchester, KY 48 hr kick-out- Come home every day to this 2-story beauty! You need country life? Well he...	4 beds \| 2 baths \| 2,388 sq.ft.	$419,000	Airbnb cash on cash: 0.81% Traditional cash on cash: 2.68% Airbnb Rental Income: $1423 Traditional Rental Income: $1729 Airbnb ROI: 0.81% Traditional ROI: 2.68%
111 Bella Shae Way Winchester, KY Welcome Home to the Park Place Floor Plan by CP Builders. This elegant ranch home features...	3 beds \| 2 baths \| 2,995 sq.ft.	$825,000	Airbnb cash on cash: -0.67% Traditional cash on cash: -0.11% Airbnb Rental Income: $1466 Traditional Rental Income: $1465 Airbnb ROI: -0.67% Traditional ROI: -0.11%
108 Ashley Drive Winchester, KY Be among the first to discover this exceptional property! This is a brand new listing, pre...	4 beds \| 2 baths \| 1,984 sq.ft.	$270,000	Airbnb cash on cash: 1.69% Traditional cash on cash: 3.95% Airbnb Rental Income: $1423 Traditional Rental Income: $1571 Airbnb ROI: 1.69% Traditional ROI: 3.95%

Real Estate investment in Winchester, KY

There are 149 properties for sale in the city of Winchester . The median list price in Winchester is $322,450 and the average price per square foot is $151. In January 2026, the average monthly cash on cash return in Winchester is 5.00%. The average monthly rental income in Winchester is $1,981.

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

There are 149 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 $1,981.

Your search for investment property begins and ends here

Investment Property for Sale in Winchester, KY

2395 Becknerville Road

Winchester, KY

4 beds | 4 baths | 3,234 sq.ft.

$849,000

Airbnb cash on cash: -0.71%

Traditional cash on cash: 2.49%

Airbnb Rental Income: $1423

Traditional Rental Income: $3530

Airbnb ROI: -0.71%

Traditional ROI: 2.49%

724 Terry Drive

Winchester, KY

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

$279,500

Airbnb cash on cash: 1.72%

Traditional cash on cash: 6%

Airbnb Rental Income: $1466

Traditional Rental Income: $2162

Airbnb ROI: 1.72%

Traditional ROI: 6%

149 Winn Ave

Winchester, KY

12 beds | 4 baths | 4,010 sq.ft.

$290,000

Airbnb cash on cash: N/A

Traditional cash on cash: 11.48%

Airbnb Rental Income: $null

Traditional Rental Income: $3514

Airbnb ROI: N/A

Traditional ROI: 11.48%

300 Calmes Boulevard

Winchester, KY

3 beds | 2 baths | 2,636 sq.ft.

$379,717

Airbnb cash on cash: 0.79%

Traditional cash on cash: 3.27%

Airbnb Rental Income: $1466

Traditional Rental Income: $1919

Airbnb ROI: 0.79%

Traditional ROI: 3.27%

213 Orchid Court

Winchester, KY

4 beds | 3 baths | 1,776 sq.ft.

$325,000

Airbnb cash on cash: 1.1%

Traditional cash on cash: 4.68%

Airbnb Rental Income: $1423

Traditional Rental Income: $2088

Airbnb ROI: 1.1%

Traditional ROI: 4.68%

407 Corinne Court

Winchester, KY

3 beds | 2 baths | 1,352 sq.ft.

$274,900

Airbnb cash on cash: 1.77%

Traditional cash on cash: 5.21%

Airbnb Rental Income: $1466

Traditional Rental Income: $1924

Airbnb ROI: 1.77%

Traditional ROI: 5.21%

175 Magnolia Street

Winchester, KY

3 beds | 1 baths | 1,046 sq.ft.

$194,900

Airbnb cash on cash: 4.03%

Traditional cash on cash: 5.95%

Airbnb Rental Income: $1466

Traditional Rental Income: $1387

Airbnb ROI: 4.03%

Traditional ROI: 5.95%

42 Mockingbird Valley Road

Winchester, KY

3 beds | 2 baths | 2,961 sq.ft.

$452,500

Airbnb cash on cash: 0.37%

Traditional cash on cash: 3.56%

Airbnb Rental Income: $1466

Traditional Rental Income: $2386

Airbnb ROI: 0.37%