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.

Single Family Homes for Sale in Winchester, KY

Search for Single Family Residential for Sale in Winchester, Kentucky. Browse all of Mashvisor’s Single Family Residential listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 139 Single Family Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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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: 1.72% Traditional cash on cash: 6% Airbnb Rental Income: $1466 Traditional Rental Income: $2162 Airbnb ROI: 1.72% Traditional ROI: 6%
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.	$319,000	Airbnb cash on cash: 1.28% Traditional cash on cash: 4.31% Airbnb Rental Income: $1466 Traditional Rental Income: $1942 Airbnb ROI: 1.28% Traditional ROI: 4.31%
118 Windridge Drive Winchester, KY Start off the new year in a new home! Imagine spending summers in your own private backyar...	3 beds \| 2 baths \| 1,617 sq.ft.	$318,000	Airbnb cash on cash: 1.29% Traditional cash on cash: 3.95% Airbnb Rental Income: $1466 Traditional Rental Income: $1829 Airbnb ROI: 1.29% Traditional ROI: 3.95%
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.	$330,000	Airbnb cash on cash: 1.06% Traditional cash on cash: 4.58% Airbnb Rental Income: $1423 Traditional Rental Income: $2088 Airbnb ROI: 1.06% Traditional ROI: 4.58%
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.	$175,000	Airbnb cash on cash: 4.59% Traditional cash on cash: 6.71% Airbnb Rental Income: $1466 Traditional Rental Income: $1387 Airbnb ROI: 4.59% Traditional ROI: 6.71%
42 Mockingbird Valley Road Winchester, KY The term 'Move In Ready' really and truly applies here at 42 Mockingbird Valley Road! Vers...	3 beds \| 2 baths \| 2,961 sq.ft.	$457,900	Airbnb cash on cash: 0.34% Traditional cash on cash: 3.5% Airbnb Rental Income: $1466 Traditional Rental Income: $2386 Airbnb ROI: 0.34% Traditional ROI: 3.5%
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.	$115,000	Airbnb cash on cash: 0.04% Traditional cash on cash: 8.58% Airbnb Rental Income: $590 Traditional Rental Income: $1251 Airbnb ROI: 0.04% Traditional ROI: 8.58%
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.	$182,000	Airbnb cash on cash: 3.58% Traditional cash on cash: 7.66% Airbnb Rental Income: $1466 Traditional Rental Income: $1740 Airbnb ROI: 3.58% Traditional ROI: 7.66%
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: 1.49% Traditional cash on cash: 3.79% Airbnb Rental Income: $1466 Traditional Rental Income: $1883 Airbnb ROI: 1.49% Traditional ROI: 3.79%
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%
165 Hilltop Drive Winchester, KY *Priced Below Recent Apraised Value* This stunning property is ideally located and is ...	3 beds \| 2 baths \| 1,454 sq.ft.	$274,900	Airbnb cash on cash: 2.58% Traditional cash on cash: 5.76% Airbnb Rental Income: $1466 Traditional Rental Income: $1856 Airbnb ROI: 2.58% Traditional ROI: 5.76%
125 Summerhill Way Winchester, KY Welcome home to this darling farmhouse-style gem on a quiet street in Winchester! You'll l...	3 beds \| 2 baths \| 1,333 sq.ft.	$259,900	Airbnb cash on cash: 2.35% Traditional cash on cash: 5.69% Airbnb Rental Income: $1466 Traditional Rental Income: $1852 Airbnb ROI: 2.35% Traditional ROI: 5.69%
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: 7.71% Airbnb Rental Income: $1466 Traditional Rental Income: $1532 Airbnb ROI: 4.11% Traditional ROI: 7.71%
214 S Burns Avenue Winchester, KY Own a beautifully maintained piece of Winchester, KY history on desirable South Burns Aven...	4 beds \| 2 baths \| 2,170 sq.ft.	$318,500	Airbnb cash on cash: 1.17% Traditional cash on cash: 3.63% Airbnb Rental Income: $1423 Traditional Rental Income: $1735 Airbnb ROI: 1.17% Traditional ROI: 3.63%
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%
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%
160 Agawam Road Winchester, KY Welcome to this beautifully maintained brick ranch home set on a spacious and private 5-ac...	3 beds \| 2 baths \| 4,933 sq.ft.	$524,000	Airbnb cash on cash: 0.06% Traditional cash on cash: 2.35% Airbnb Rental Income: $1466 Traditional Rental Income: $2151 Airbnb ROI: 0.06% Traditional ROI: 2.35%
208 Watercrest Way Winchester, KY Welcome home! This charming 3 bedroom, 2.5 bath property offers comfort and style with tho...	3 beds \| 2 baths \| 1,416 sq.ft.	$255,000	Airbnb cash on cash: 2.05% Traditional cash on cash: 5.19% Airbnb Rental Income: $1466 Traditional Rental Income: $1788 Airbnb ROI: 2.05% Traditional ROI: 5.19%
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%
202 Dubuy Drive Winchester, KY Step inside this meticulously maintained residence, essentially offering the rare opportun...	3 beds \| 2 baths \| 1,800 sq.ft.	$305,000	Airbnb cash on cash: 1.42% Traditional cash on cash: 5.31% Airbnb Rental Income: $1466 Traditional Rental Income: $2150 Airbnb ROI: 1.42% Traditional ROI: 5.31%
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%
1701 Gay Evans Road Winchester, KY Move into INSTANT equity Listed BELOW appraisal! This 4bd 4bath home has 2 BONUS ROOMS, a ...	4 beds \| 4 baths \| 4,345 sq.ft.	$829,000	Airbnb cash on cash: -0.68% Traditional cash on cash: 2.23% Airbnb Rental Income: $1423 Traditional Rental Income: $3249 Airbnb ROI: -0.68% Traditional ROI: 2.23%
200 Madison Avenue Winchester, KY Charming 3-bedroom, 2-bath ranch featuring a spacious living room and a separate dining ar...	3 beds \| 2 baths \| 1,124 sq.ft.	$179,000	Airbnb cash on cash: 3.67% Traditional cash on cash: 5.05% Airbnb Rental Income: $1466 Traditional Rental Income: $1269 Airbnb ROI: 3.67% Traditional ROI: 5.05%
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: -0.68% Traditional cash on cash: 1.31% Airbnb Rental Income: $1423 Traditional Rental Income: $2523 Airbnb ROI: -0.68% 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 \| 2 baths \| 2,770 sq.ft.	$674,500	Airbnb cash on cash: -0.47% Traditional cash on cash: 2.43% Airbnb Rental Income: $1423 Traditional Rental Income: $2823 Airbnb ROI: -0.47% Traditional ROI: 2.43%
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.	$229,000	Airbnb cash on cash: 2.49% Traditional cash on cash: 3.29% Airbnb Rental Income: $1466 Traditional Rental Income: $1207 Airbnb ROI: 2.49% Traditional ROI: 3.29%
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%
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.	$240,000	Airbnb cash on cash: 2.79% Traditional cash on cash: 6.29% Airbnb Rental Income: $1466 Traditional Rental Income: $1828 Airbnb ROI: 2.79% Traditional ROI: 6.29%
120 Jackson Street Winchester, KY Step into modern comfort just minutes from the heart of downtown Winchester. This nearly n...	3 beds \| 2 baths \| 1,342 sq.ft.	$248,000	Airbnb cash on cash: 2.86% Traditional cash on cash: 4.29% Airbnb Rental Income: $1466 Traditional Rental Income: $1368 Airbnb ROI: 2.86% Traditional ROI: 4.29%
670 Lillies Ferry Road Winchester, KY MOTIVATED SELLERS Escape to this serene and private 12+ acre property, boasting a 3BR/2B...	3 beds \| 2 baths \| 2,053 sq.ft.	$489,000	Airbnb cash on cash: 0.75% Traditional cash on cash: 1.37% Airbnb Rental Income: $1466 Traditional Rental Income: $1316 Airbnb ROI: 0.75% Traditional ROI: 1.37%
115 College Street Winchester, KY Charming 1940 Home with Modern Upgrades! Step into a timeless character blended with moder...	3 beds \| 2 baths \| 1,839 sq.ft.	$300,000	Airbnb cash on cash: 1.47% Traditional cash on cash: 3.19% Airbnb Rental Income: $1466 Traditional Rental Income: $1517 Airbnb ROI: 1.47% Traditional ROI: 3.19%
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%

Your search for investment property begins and ends here

Single Family Homes for Sale in Winchester, KY

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%

410 Corinne Court

Winchester, KY

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

$319,000

Airbnb cash on cash: 1.28%

Traditional cash on cash: 4.31%

Airbnb Rental Income: $1466

Traditional Rental Income: $1942

Airbnb ROI: 1.28%

Traditional ROI: 4.31%

118 Windridge Drive

Winchester, KY

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

$318,000

Airbnb cash on cash: 1.29%

Traditional cash on cash: 3.95%

Airbnb Rental Income: $1466

Traditional Rental Income: $1829

Airbnb ROI: 1.29%

Traditional ROI: 3.95%

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.

$330,000

Airbnb cash on cash: 1.06%

Traditional cash on cash: 4.58%

Airbnb Rental Income: $1423

Traditional Rental Income: $2088

Airbnb ROI: 1.06%

Traditional ROI: 4.58%

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.

$175,000

Airbnb cash on cash: 4.59%

Traditional cash on cash: 6.71%

Airbnb Rental Income: $1466

Traditional Rental Income: $1387

Airbnb ROI: 4.59%

Traditional ROI: 6.71%

42 Mockingbird Valley Road

Winchester, KY

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

$457,900

Airbnb cash on cash: 0.34%

Traditional cash on cash: 3.5%

Airbnb Rental Income: $1466

Traditional Rental Income: $2386

Airbnb ROI: 0.34%