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
210 College Street Winchester, KY Take a peak at this brick 2 story charmer! Coffered ceilings, full granite backsplash & c...	4 beds \| 4 baths \| 2,904 sq.ft.	$429,900	Airbnb cash on cash: 3.13% Traditional cash on cash: 6.28% Airbnb Rental Income: $2363 Traditional Rental Income: $3049 Airbnb ROI: 3.13% Traditional ROI: 6.28%
19 Virginia Avenue Winchester, KY Welcome to a lovely home that has been well maintained and loved. Move in ready and price...	4 beds \| 2 baths \| 1,619 sq.ft.	$259,000	Airbnb cash on cash: 5.83% Traditional cash on cash: 6.63% Airbnb Rental Income: $2363 Traditional Rental Income: $1976 Airbnb ROI: 5.83% Traditional ROI: 6.63%
163 Hawthorne Drive Winchester, KY Now is your chance to own a home in the Earlymeade subdivision. The 2018 built home boasts...	4 beds \| 3 baths \| 2,830 sq.ft.	$499,900	Airbnb cash on cash: 2.6% Traditional cash on cash: 4.56% Airbnb Rental Income: $2363 Traditional Rental Income: $2697 Airbnb ROI: 2.6% Traditional ROI: 4.56%
502 Hewlett Court Winchester, KY OPEN HOUSE, Sunday, September 15, hours 1-3 Happiness is this two story home with lots ...	3 beds \| 3 baths \| 2,384 sq.ft.	$345,000	Airbnb cash on cash: 6.68% Traditional cash on cash: 5.13% Airbnb Rental Income: $3657 Traditional Rental Income: $2357 Airbnb ROI: 6.68% Traditional ROI: 5.13%
42 Mockingbird Valley Road Winchester, KY Beautiful Hampton Manor home offers easy access to all Winchester has to offer! Located ri...	3 beds \| 3 baths \| 3,261 sq.ft.	$465,000	Airbnb cash on cash: 4.5% Traditional cash on cash: 3.42% Airbnb Rental Income: $3657 Traditional Rental Income: $2386 Airbnb ROI: 4.5% Traditional ROI: 3.42%
603 Westmeade Drive Winchester, KY Wow!!! This Is The One You Have Been Waiting For! This 4 Bedroom 2 Bath Home Has Space Fo...	4 beds \| 2 baths \| 1,866 sq.ft.	$259,900	Airbnb cash on cash: 5.03% Traditional cash on cash: 6.33% Airbnb Rental Income: $2363 Traditional Rental Income: $2099 Airbnb ROI: 5.03% Traditional ROI: 6.33%
112 Sycamore Street Winchester, KY Don't miss out on these 2 great income producing properties that are situated on the same ...	4 beds \| 2 baths \| 1,380 sq.ft.	$175,000	Airbnb cash on cash: 8.27% Traditional cash on cash: 7.87% Airbnb Rental Income: $2363 Traditional Rental Income: $1713 Airbnb ROI: 8.27% Traditional ROI: 7.87%
2482 Mina Station Road Winchester, KY Move in Ready! 3 bedroom 2 full bath. Gorgeous updated kitchen with TONS of cabinet space,...	3 beds \| 2 baths \| 1,756 sq.ft.	$310,000	Airbnb cash on cash: 7.63% Traditional cash on cash: 3.72% Airbnb Rental Income: $3657 Traditional Rental Income: $1719 Airbnb ROI: 7.63% Traditional ROI: 3.72%
509 Lasalle Court Winchester, KY Rare Ranch on a Basement! Sitting on almost an acre, this is the perfect home to bring you...	3 beds \| 3 baths \| 2,484 sq.ft.	$308,000	Airbnb cash on cash: 7.69% Traditional cash on cash: 6.29% Airbnb Rental Income: $3657 Traditional Rental Income: $2454 Airbnb ROI: 7.69% Traditional ROI: 6.29%
142 Spruce Court Winchester, KY Great All Brick Ranch offers 4 bedrooms, 1.5 bathrooms, Spacious Kitchen, Nice Living Room...	4 beds \| 2 baths \| 1,215 sq.ft.	$185,000	Airbnb cash on cash: 7.74% Traditional cash on cash: 7.92% Airbnb Rental Income: $2363 Traditional Rental Income: $1813 Airbnb ROI: 7.74% Traditional ROI: 7.92%
111 South Burns Avenue Winchester, KY Reduced for quick sale!! Don't miss out on your opportunity to own a 100+ year old home l...	4 beds \| 3 baths \| 2,994 sq.ft.	$309,000	Airbnb cash on cash: 3.95% Traditional cash on cash: 8.45% Airbnb Rental Income: $2363 Traditional Rental Income: $3088 Airbnb ROI: 3.95% Traditional ROI: 8.45%
27 Sundown Lane Winchester, KY Discover your own slice of paradise at this stunning colonial-style home nestled on 71 pic...	4 beds \| 6 baths \| 5,220 sq.ft.	$2,500,000	Airbnb cash on cash: -1.13% Traditional cash on cash: 0.79% Airbnb Rental Income: $2363 Traditional Rental Income: $6222 Airbnb ROI: -1.13% Traditional ROI: 0.79%
122 Buckingham Lane Winchester, KY Move- in ready 3 bed and 2 bath ranch!! Now that I have your attention, how about some re...	3 beds \| 2 baths \| 1,240 sq.ft.	$280,000	Airbnb cash on cash: 8.63% Traditional cash on cash: 2.84% Airbnb Rental Income: $3657 Traditional Rental Income: $1331 Airbnb ROI: 8.63% Traditional ROI: 2.84%
440 Flanagan Station Road Winchester, KY Beautiful, Sprawling Brick Ranch Home on 7.8 Acres * 3-Stall Barn with Run-in/Hay Storage ...	3 beds \| 3 baths \| 2,620 sq.ft.	$525,000	Airbnb cash on cash: 3.78% Traditional cash on cash: 2.97% Airbnb Rental Income: $3657 Traditional Rental Income: $2461 Airbnb ROI: 3.78% Traditional ROI: 2.97%
209 Robyn Drive Winchester, KY Welcome to this beautiful, newly renovated 3 bedroom 2 1/2 bathroom ranch on a finished ba...	3 beds \| 3 baths \| 1,825 sq.ft.	$275,000	Airbnb cash on cash: 8.81% Traditional cash on cash: 5.16% Airbnb Rental Income: $3657 Traditional Rental Income: $1910 Airbnb ROI: 8.81% Traditional ROI: 5.16%
420 Alexis Way Winchester, KY WOW! Exceptional! Attention to detail was clearly taken in the building of this stunning h...	4 beds \| 3 baths \| 2,770 sq.ft.	$850,000	Airbnb cash on cash: 0.25% Traditional cash on cash: 1.56% Airbnb Rental Income: $2363 Traditional Rental Income: $2823 Airbnb ROI: 0.25% Traditional ROI: 1.56%
31 Mockingbird Valley Road Winchester, KY This stately, split-level brick home is situated in the beautiful and desirable Hampton Ma...	4 beds \| 2 baths \| 2,520 sq.ft.	$389,900	Airbnb cash on cash: 3.11% Traditional cash on cash: 4.6% Airbnb Rental Income: $2363 Traditional Rental Income: $2323 Airbnb ROI: 3.11% Traditional ROI: 4.6%
104 Bella Shae Way Winchester, KY Proposed construction on lot 117 in luxurious new subdivision Mallard Cove! This gorgeous ...	3 beds \| 2 baths \| 2,200 sq.ft.	$516,000	Airbnb cash on cash: 3.83% Traditional cash on cash: 2.41% Airbnb Rental Income: $3657 Traditional Rental Income: $2172 Airbnb ROI: 3.83% Traditional ROI: 2.41%
308 West Hickman Street Winchester, KY Welcome to this beautifully remodeled gem where classic charm meets modern luxury! This sp...	5 beds \| 3 baths \| 2,681 sq.ft.	$385,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.36% Airbnb Rental Income: $null Traditional Rental Income: $2698 Airbnb ROI: N/A Traditional ROI: 5.36%
414 Alexis Way Winchester, KY Welcome to this exquisite modern cottage only 12 miles from Hamburg, Stepping inside the a...	3 beds \| 3 baths \| 2,643 sq.ft.	$625,000	Airbnb cash on cash: 2.85% Traditional cash on cash: 2.18% Airbnb Rental Income: $3657 Traditional Rental Income: $2470 Airbnb ROI: 2.85% Traditional ROI: 2.18%
31 West Hickman Street Winchester, KY We are honored to present this rare opportunity to purchase a beautiful, historic property...	4 beds \| 3 baths \| 5,328 sq.ft.	$599,000	Airbnb cash on cash: 1.16% Traditional cash on cash: 2.75% Airbnb Rental Income: $2363 Traditional Rental Income: $2668 Airbnb ROI: 1.16% Traditional ROI: 2.75%
511 Boone Avenue Winchester, KY One of a kind opportunity to live in history and in luxury in one of Winchester's finest o...	4 beds \| 5 baths \| 4,698 sq.ft.	$985,000	Airbnb cash on cash: 0.34% Traditional cash on cash: 3.2% Airbnb Rental Income: $2363 Traditional Rental Income: $4402 Airbnb ROI: 0.34% Traditional ROI: 3.2%
1112 Andover Drive #Lot 194 Winchester, KY New construction home for sale in Williamsburg Park Subdivision located in Franklin KY. Sp...	4 beds \| 2 baths \| 1,700 sq.ft.	$331,900	Airbnb cash on cash: 3.56% Traditional cash on cash: 4.86% Airbnb Rental Income: $2363 Traditional Rental Income: $2188 Airbnb ROI: 3.56% Traditional ROI: 4.86%
1118 Andover Drive #Lot 191 Winchester, KY Beautiful new construction home located on a corner lot. This home's interior features; LV...	4 beds \| 2 baths \| 1,610 sq.ft.	$331,900	Airbnb cash on cash: 3.56% Traditional cash on cash: 4.58% Airbnb Rental Income: $2363 Traditional Rental Income: $2100 Airbnb ROI: 3.56% Traditional ROI: 4.58%
422 Alexis Way Winchester, KY Proposed construction on lot 122 in luxurious new subdivision Mallard Cove! This gorgeous ...	3 beds \| 4 baths \| 3,053 sq.ft.	$760,000	Airbnb cash on cash: 2.02% Traditional cash on cash: 2.05% Airbnb Rental Income: $3657 Traditional Rental Income: $2882 Airbnb ROI: 2.02% Traditional ROI: 2.05%
2417 Old Boonesboro Road Winchester, KY Location! Location! This is a prime spot in Winchester. There are so many possibilities wi...	3 beds \| 1 baths \| 1,732 sq.ft.	$279,000	Airbnb cash on cash: 8.66% Traditional cash on cash: 4.4% Airbnb Rental Income: $3657 Traditional Rental Income: $1738 Airbnb ROI: 8.66% Traditional ROI: 4.4%
31 Bonnie Brook Lane Winchester, KY This is rare beauty and history located in the heart of Winchester. Embrace the essence of...	5 beds \| 4 baths \| 4,091 sq.ft.	$575,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.99% Airbnb Rental Income: $null Traditional Rental Income: $3768 Airbnb ROI: N/A Traditional ROI: 4.99%
425 Wellington Way Winchester, KY Move in and relax! This beautiful property has been meticulously updated and ready for you...	3 beds \| 3 baths \| 1,727 sq.ft.	$271,900	Airbnb cash on cash: 9.3% Traditional cash on cash: 5.13% Airbnb Rental Income: $3657 Traditional Rental Income: $1788 Airbnb ROI: 9.3% Traditional ROI: 5.13%
2296 Trapp-Goffs Cor Road Winchester, KY At the Last Minute - Buyers Changed their mind! Their loss can be your gain! Property has ...	3 beds \| 2 baths \| 1,680 sq.ft.	$315,000	Airbnb cash on cash: 7.48% Traditional cash on cash: 3.75% Airbnb Rental Income: $3657 Traditional Rental Income: $1755 Airbnb ROI: 7.48% Traditional ROI: 3.75%
1363 Clintonville Road Winchester, KY Embrace the potential of this 5-acre gem near Winchester and Hamburg, KY. Located in beaut...	2 beds \| 1 baths \| 1,116 sq.ft.	$340,000	Airbnb cash on cash: 2.69% Traditional cash on cash: 2.13% Airbnb Rental Income: $2082 Traditional Rental Income: $1365 Airbnb ROI: 2.69% Traditional ROI: 2.13%
427 Alexis Way Winchester, KY Introducing A Stunning Traditional Home with a Rustic Twist just 12 miles from Hamburg Of ...	3 beds \| 4 baths \| 2,199 sq.ft.	$535,000	Airbnb cash on cash: 3.63% Traditional cash on cash: 3.46% Airbnb Rental Income: $3657 Traditional Rental Income: $2772 Airbnb ROI: 3.63% Traditional ROI: 3.46%
621 Boone Avenue Winchester, KY Discover unparalleled elegance with no detail left unturned, nestled on 4 acres in the hea...	5 beds \| 6 baths \| 5,498 sq.ft.	$1,200,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.79% Airbnb Rental Income: $null Traditional Rental Income: $5862 Airbnb ROI: N/A Traditional ROI: 3.79%
162 French Avenue Winchester, KY 162 French Ave, Winchester, Kentucky, is a charming residential property located in a quie...	4 beds \| 1 baths \| 2,327 sq.ft.	$219,000	Airbnb cash on cash: 6.75% Traditional cash on cash: 6.67% Airbnb Rental Income: $2363 Traditional Rental Income: $1763 Airbnb ROI: 6.75% Traditional ROI: 6.67%
31 Skylark Drive Winchester, KY Once you come in you won't leave, this sprawling ranch with a nice back yard just waiting ...	4 beds \| 3 baths \| 2,908 sq.ft.	$330,000	Airbnb cash on cash: 3.91% Traditional cash on cash: 6.94% Airbnb Rental Income: $2363 Traditional Rental Income: $2720 Airbnb ROI: 3.91% Traditional ROI: 6.94%
106 Old Ironworks Road Winchester, KY Victorian Home - Winchester, KY. Are you looking for that classic Victorian style home th...	5 beds \| 3 baths \| 3,380 sq.ft.	$309,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.65% Airbnb Rental Income: $null Traditional Rental Income: $2773 Airbnb ROI: N/A Traditional ROI: 7.65%
3431 Colby Road Winchester, KY Back on the market. A diamond in the rough. Stately views with a long driveway from Colby ...	4 beds \| 2 baths \| 3,788 sq.ft.	$350,000	Airbnb cash on cash: 3.28% Traditional cash on cash: 3.65% Airbnb Rental Income: $2363 Traditional Rental Income: $1902 Airbnb ROI: 3.28% Traditional ROI: 3.65%
142 College Street Winchester, KY Seller Is Offering a $5,000.00 Agent Bonus With Acceptable Offer!!! This One Is Special! ...	4 beds \| 3 baths \| 3,012 sq.ft.	$429,900	Airbnb cash on cash: 2.34% Traditional cash on cash: 5.29% Airbnb Rental Income: $2363 Traditional Rental Income: $2968 Airbnb ROI: 2.34% Traditional ROI: 5.29%
576 Earlymeade Drive Winchester, KY Welcome to this charming home that blends warmth with elegance. Enter into a gracious foye...	4 beds \| 4 baths \| 3,420 sq.ft.	$469,000	Airbnb cash on cash: 2.33% Traditional cash on cash: 5.8% Airbnb Rental Income: $2363 Traditional Rental Income: $3305 Airbnb ROI: 2.33% Traditional ROI: 5.8%
128 Cherokee Drive Winchester, KY Back on market! Buyer changed their mind before home inspection, no fault of the sellers! ...	5 beds \| 2 baths \| 2,082 sq.ft.	$275,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.91% Airbnb Rental Income: $null Traditional Rental Income: $2365 Airbnb ROI: N/A Traditional ROI: 6.91%
116 Park Avenue Winchester, KY This place would be a great starter home or investment opportunity. This home is clean and...	1 beds \| 1 baths \| 1,576 sq.ft.	$120,000	Airbnb cash on cash: 5.91% Traditional cash on cash: 8.34% Airbnb Rental Income: $1416 Traditional Rental Income: $1273 Airbnb ROI: 5.91% Traditional ROI: 8.34%

Real Estate investment in Winchester, KY

There are 78 properties for sale in the city of Winchester . The median list price in Winchester is $275,000 and the average price per square foot is $129. In November 2024, the average monthly cash on cash return in Winchester is 5.00%. The average monthly rental income in Winchester is $1,947.

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

There are 78 investment properties available for sale in Winchester.

In 2024, the best neighborhood to buy investment property is Winchester.

The ROI for Short-Term is higher than the Long-Term in Winchester with average rental income of $3,657.

Your search for investment property begins and ends here

Investment Property for Sale in Winchester, KY

210 College Street

Winchester, KY

4 beds | 4 baths | 2,904 sq.ft.

$429,900

Airbnb cash on cash: 3.13%

Traditional cash on cash: 6.28%

Airbnb Rental Income: $2363

Traditional Rental Income: $3049

Airbnb ROI: 3.13%

Traditional ROI: 6.28%

19 Virginia Avenue

Winchester, KY

4 beds | 2 baths | 1,619 sq.ft.

$259,000

Airbnb cash on cash: 5.83%

Traditional cash on cash: 6.63%

Airbnb Rental Income: $2363

Traditional Rental Income: $1976

Airbnb ROI: 5.83%

Traditional ROI: 6.63%

163 Hawthorne Drive

Winchester, KY

4 beds | 3 baths | 2,830 sq.ft.

$499,900

Airbnb cash on cash: 2.6%

Traditional cash on cash: 4.56%

Airbnb Rental Income: $2363

Traditional Rental Income: $2697

Airbnb ROI: 2.6%

Traditional ROI: 4.56%

502 Hewlett Court

Winchester, KY

3 beds | 3 baths | 2,384 sq.ft.

$345,000

Airbnb cash on cash: 6.68%

Traditional cash on cash: 5.13%

Airbnb Rental Income: $3657

Traditional Rental Income: $2357

Airbnb ROI: 6.68%

Traditional ROI: 5.13%

42 Mockingbird Valley Road

Winchester, KY

3 beds | 3 baths | 3,261 sq.ft.

$465,000

Airbnb cash on cash: 4.5%

Traditional cash on cash: 3.42%

Airbnb Rental Income: $3657

Traditional Rental Income: $2386

Airbnb ROI: 4.5%

Traditional ROI: 3.42%

603 Westmeade Drive

Winchester, KY

4 beds | 2 baths | 1,866 sq.ft.

$259,900

Airbnb cash on cash: 5.03%

Traditional cash on cash: 6.33%

Airbnb Rental Income: $2363

Traditional Rental Income: $2099

Airbnb ROI: 5.03%

Traditional ROI: 6.33%

112 Sycamore Street

Winchester, KY

4 beds | 2 baths | 1,380 sq.ft.

$175,000

Airbnb cash on cash: 8.27%

Traditional cash on cash: 7.87%

Airbnb Rental Income: $2363

Traditional Rental Income: $1713

Airbnb ROI: 8.27%

Traditional ROI: 7.87%

2482 Mina Station Road

Winchester, KY

3 beds | 2 baths | 1,756 sq.ft.

$310,000

Airbnb cash on cash: 7.63%

Traditional cash on cash: 3.72%

Airbnb Rental Income: $3657

Traditional Rental Income: $1719

Airbnb ROI: 7.63%