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 156 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
339 S Main Street Winchester, KY Beautiful move-in ready Cape Cod home on the edge of historic downtown Winchester! This ho...	4 beds \| 2 baths \| 1,848 sq.ft.	$219,900	Airbnb cash on cash: 2.74% Traditional cash on cash: 8.05% Airbnb Rental Income: $1487 Traditional Rental Income: $2156 Airbnb ROI: 2.74% Traditional ROI: 8.05%
618 Westmeade Drive Winchester, KY PRICE IMPROVEMENT + $3,000 BUYER CREDIT! Motivated seller has adjusted the price to $289,9...	4 beds \| 2 baths \| 2,116 sq.ft.	$289,900	Airbnb cash on cash: 1.65% Traditional cash on cash: 6.23% Airbnb Rental Income: $1487 Traditional Rental Income: $2301 Airbnb ROI: 1.65% Traditional ROI: 6.23%
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%
207 Hibiscus Lane Winchester, KY Welcome to 207 Hibiscus Ln, will this be your new address? This beautifully maintained hom...	4 beds \| 3 baths \| 3,126 sq.ft.	$449,900	Airbnb cash on cash: 0.42% Traditional cash on cash: 4.64% Airbnb Rental Income: $1487 Traditional Rental Income: $2827 Airbnb ROI: 0.42% Traditional ROI: 4.64%
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 wi...	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%
20 Edgewood Drive Winchester, KY Welcome to this beautiful brick ranch on a basement in Hampton Manor. The double front doo...	3 beds \| 3 baths \| 2,289 sq.ft.	$427,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.56% Airbnb Rental Income: $null Traditional Rental Income: $1857 Airbnb ROI: N/A Traditional ROI: 2.56%
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: 3.51% Traditional cash on cash: 9.81% Airbnb Rental Income: $1487 Traditional Rental Income: $2304 Airbnb ROI: 3.51% Traditional ROI: 9.81%
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.	$169,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.98% Airbnb Rental Income: $null Traditional Rental Income: $1387 Airbnb ROI: N/A Traditional ROI: 6.98%
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.	$310,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.94% Airbnb Rental Income: $null Traditional Rental Income: $2657 Airbnb ROI: N/A Traditional ROI: 6.94%
327 Newcastle Lane Winchester, KY PRICE REDUCTION!!! Perfect for investment or primary residence. Welcome home to this cozy ...	4 beds \| 3 baths \| 1,693 sq.ft.	$284,900	Airbnb cash on cash: 2.49% Traditional cash on cash: 5.61% Airbnb Rental Income: $1487 Traditional Rental Income: $1887 Airbnb ROI: 2.49% Traditional ROI: 5.61%
178 Hawthorne Drive Winchester, KY Welcome to your Kentucky haven. This charming 3 bedroom, 2.5 bath home has a covered front...	3 beds \| 3 baths \| 2,156 sq.ft.	$390,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.12% Airbnb Rental Income: $null Traditional Rental Income: $2336 Airbnb ROI: N/A Traditional ROI: 5.12%
125 Kittison Drive Winchester, KY Charming ranch home featuring 3 bedrooms, 1 full bath with a spacious layout and inviting ...	3 beds \| 1 baths \| 1,100 sq.ft.	$239,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.42% Airbnb Rental Income: $null Traditional Rental Income: $1336 Airbnb ROI: N/A Traditional ROI: 4.42%
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%
13 Lakeview Drive Winchester, KY Beautifully updated brick ranch with a partially finished basement offering 3 bedrooms and...	3 beds \| 2 baths \| 1,932 sq.ft.	$315,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.89% Airbnb Rental Income: $null Traditional Rental Income: $1498 Airbnb ROI: N/A Traditional ROI: 2.89%
107 Patio Street Winchester, KY What a cute little dollhouse. Move in Ready . Corner lot with storage building. Close to a...	2 beds \| 1 baths \| 864 sq.ft.	$160,000	Airbnb cash on cash: 2.28% Traditional cash on cash: 5.53% Airbnb Rental Income: $1097 Traditional Rental Income: $1221 Airbnb ROI: 2.28% Traditional ROI: 5.53%
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.	$289,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.63% Airbnb Rental Income: $null Traditional Rental Income: $1859 Airbnb ROI: N/A Traditional ROI: 4.63%
274 Greenway Drive Winchester, KY Beautifully updated 4 bedroom, 2 bath brick ranch situated on a spacious .55+/- acre lot i...	4 beds \| 2 baths \| 2,208 sq.ft.	$350,000	Airbnb cash on cash: 1.48% Traditional cash on cash: 5.11% Airbnb Rental Income: $1487 Traditional Rental Income: $2242 Airbnb ROI: 1.48% Traditional ROI: 5.11%
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%
405 Tremont Lane Winchester, KY Welcome to this beautifully maintained 4 bedroom, 2.5 bathroom home over 2,200 square feet...	4 beds \| 3 baths \| 2,274 sq.ft.	$349,000	Airbnb cash on cash: 1.07% Traditional cash on cash: 4.67% Airbnb Rental Income: $1487 Traditional Rental Income: $2231 Airbnb ROI: 1.07% Traditional ROI: 4.67%
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 \| 2,444 sq.ft.	$199,900	Airbnb cash on cash: N/A Traditional cash on cash: 10.57% Airbnb Rental Income: $null Traditional Rental Income: $2299 Airbnb ROI: N/A Traditional ROI: 10.57%
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.	$329,900	Airbnb cash on cash: 2.01% Traditional cash on cash: 5.71% Airbnb Rental Income: $1487 Traditional Rental Income: $2198 Airbnb ROI: 2.01% Traditional ROI: 5.71%
403 Pueblo Court Winchester, KY Built in 2020, this well-maintained Craftsman-style ranch offers the benefits of newer con...	3 beds \| 2 baths \| 1,311 sq.ft.	$274,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.41% Airbnb Rental Income: $null Traditional Rental Income: $1717 Airbnb ROI: N/A Traditional ROI: 4.41%
209 Boone Avenue Winchester, KY Space, updates, and charm all come together in this spacious 2,260 square foot 1.5-story h...	3 beds \| 3 baths \| 2,260 sq.ft.	$299,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.58% Airbnb Rental Income: $null Traditional Rental Income: $2473 Airbnb ROI: N/A Traditional ROI: 6.58%
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.	$349,900	Airbnb cash on cash: 1.9% Traditional cash on cash: 6.7% Airbnb Rental Income: $1487 Traditional Rental Income: $2629 Airbnb ROI: 1.9% Traditional ROI: 6.7%
407 Pueblo Court Winchester, KY Welcome to 407 Pueblo Court! This well-kept 3 bed, 2 bath home sits on a quiet cul-de-sac ...	3 beds \| 2 baths \| 1,244 sq.ft.	$240,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.6% Airbnb Rental Income: $null Traditional Rental Income: $1607 Airbnb ROI: N/A Traditional ROI: 5.6%
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.	$694,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.12% Airbnb Rental Income: $null Traditional Rental Income: $3588 Airbnb ROI: N/A Traditional ROI: 4.12%
414 Pueblo Court Winchester, KY PRICE DROP and a MOTIVATED SELLER!! Currently priced below 2026 Clark County Department of...	3 beds \| 3 baths \| 2,648 sq.ft.	$289,999	Airbnb cash on cash: N/A Traditional cash on cash: 7.32% Airbnb Rental Income: $null Traditional Rental Income: $2598 Airbnb ROI: N/A Traditional ROI: 7.32%
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%
13 Long Avenue Winchester, KY Charming 3 bedroom, 2 bath home situated on a large, level lot! Relax and enjoy the inviti...	3 beds \| 2 baths \| 1,297 sq.ft.	$240,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.6% Airbnb Rental Income: $null Traditional Rental Income: $1558 Airbnb ROI: N/A Traditional ROI: 4.6%
4578 Combs Ferry Road Winchester, KY Welcome to your own slice of Kentucky countryside! Situated on 59.104 picturesque acres, t...	3 beds \| 2 baths \| 1,860 sq.ft.	$1,750,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.62% Airbnb Rental Income: $null Traditional Rental Income: $2097 Airbnb ROI: N/A Traditional ROI: -0.62%
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.	$299,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.74% Airbnb Rental Income: $null Traditional Rental Income: $2238 Airbnb ROI: N/A Traditional ROI: 5.74%
147 Sunset Heights Winchester, KY This charming 3-bedroom, 2-bath home offers the perfect blend of comfort, space, and poten...	3 beds \| 2 baths \| 2,128 sq.ft.	$294,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.75% Airbnb Rental Income: $null Traditional Rental Income: $2203 Airbnb ROI: N/A Traditional ROI: 5.75%
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.	$329,900	Airbnb cash on cash: 1.24% Traditional cash on cash: 4.17% Airbnb Rental Income: $1487 Traditional Rental Income: $1961 Airbnb ROI: 1.24% Traditional ROI: 4.17%
108 Bella Shae Way Winchester, KY Nearly new French country ranch that has been gently lived in. This classy home has magnif...	3 beds \| 2 baths \| 2,280 sq.ft.	$558,900	Airbnb cash on cash: N/A Traditional cash on cash: 1.56% Airbnb Rental Income: $null Traditional Rental Income: $1876 Airbnb ROI: N/A Traditional ROI: 1.56%
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%
7300 Old Boonesboro Road Winchester, KY This beautiful home sits on over 7 acres of peaceful countryside. Bring your horse! The ba...	4 beds \| 3 baths \| 3,311 sq.ft.	$785,000	Airbnb cash on cash: -0.55% Traditional cash on cash: 1.47% Airbnb Rental Income: $1487 Traditional Rental Income: $2523 Airbnb ROI: -0.55% Traditional ROI: 1.47%

Your search for investment property begins and ends here

Single Family Homes for Sale in Winchester, KY

339 S Main Street

Winchester, KY

4 beds | 2 baths | 1,848 sq.ft.

$219,900

Airbnb cash on cash: 2.74%

Traditional cash on cash: 8.05%

Airbnb Rental Income: $1487

Traditional Rental Income: $2156

Airbnb ROI: 2.74%

Traditional ROI: 8.05%

618 Westmeade Drive

Winchester, KY

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

$289,900

Airbnb cash on cash: 1.65%

Traditional cash on cash: 6.23%

Airbnb Rental Income: $1487

Traditional Rental Income: $2301

Airbnb ROI: 1.65%

Traditional ROI: 6.23%

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%

207 Hibiscus Lane

Winchester, KY

4 beds | 3 baths | 3,126 sq.ft.

$449,900

Airbnb cash on cash: 0.42%

Traditional cash on cash: 4.64%

Airbnb Rental Income: $1487

Traditional Rental Income: $2827

Airbnb ROI: 0.42%

Traditional ROI: 4.64%

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%

20 Edgewood Drive

Winchester, KY

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

$427,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.56%

Airbnb Rental Income: $null

Traditional Rental Income: $1857

Airbnb ROI: N/A

Traditional ROI: 2.56%

34 Hays Street

Winchester, KY

4 beds | 2 baths | 2,450 sq.ft.

$210,000

Airbnb cash on cash: 3.51%

Traditional cash on cash: 9.81%

Airbnb Rental Income: $1487

Traditional Rental Income: $2304

Airbnb ROI: 3.51%