Real Estate Investment Properties for Sale in Winchester, IN

Looking for investment property in Winchester, IN with high ROI ?

Explore a variety of short-term homes & houses in Winchester, IN. Invest wisely with VRBO & Winchester, IN 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, IN

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
No properties are listed in Winchester, Indiana at the moment.
Other Investment Properties for Sale in Indiana
824 E Minnesota Street Indianapolis , IN This home screams modern charm! Welcome to this updated 4 bedroom, 2 bath home in Bates-He...	4 beds \| 2 baths \| 2,122 sq.ft.	$370,000	Airbnb cash on cash: 0.94% Traditional cash on cash: 5.01% Airbnb Rental Income: $1253 Traditional Rental Income: $2267 Airbnb ROI: 0.94% Traditional ROI: 5.01%
15675 Wescott Drive Noblesville , IN Say goodbye to all the weekend yard chores. This Olthof home merges the convenience of con...	2 beds \| 2 baths \| 1,718 sq.ft.	$374,900	Airbnb cash on cash: -0.09% Traditional cash on cash: 3.54% Airbnb Rental Income: $1372 Traditional Rental Income: $2230 Airbnb ROI: -0.09% Traditional ROI: 3.54%
201 Walnut Street Advance , IN Welcome home to this charming 2 bedroom, 2 bath property sitting on almost half an acre (....	2 beds \| 2 baths \| 1,056 sq.ft.	$184,900	Airbnb cash on cash: N/A Traditional cash on cash: 8.58% Airbnb Rental Income: $null Traditional Rental Income: $1851 Airbnb ROI: N/A Traditional ROI: 8.58%
8660 Fawn Way McCordsville , IN Better than new! This beautifully updated home near Geist Reservoir features upgraded floo...	3 beds \| 3 baths \| 2,263 sq.ft.	$379,900	Airbnb cash on cash: 0.89% Traditional cash on cash: 4.12% Airbnb Rental Income: $1588 Traditional Rental Income: $2283 Airbnb ROI: 0.89% Traditional ROI: 4.12%
2028 Burch Drive Indianapolis , IN Charming Cape Cod Style home, just one block from Broad Ripple Park's tennis courts, trail...	4 beds \| 2 baths \| 2,289 sq.ft.	$325,000	Airbnb cash on cash: 2.49% Traditional cash on cash: 5.93% Airbnb Rental Income: $1861 Traditional Rental Income: $2413 Airbnb ROI: 2.49% Traditional ROI: 5.93%
422 W 41st Street Indianapolis , IN This newly renovated single-family residence near Butler University presents a compelling ...	3 beds \| 2 baths \| 1,328 sq.ft.	$265,000	Airbnb cash on cash: 2.22% Traditional cash on cash: 5.02% Airbnb Rental Income: $1396 Traditional Rental Income: $1674 Airbnb ROI: 2.22% Traditional ROI: 5.02%
206 N Beville Avenue Indianapolis , IN Be the first to live in this fully renovated 5-bedroom, 3-bath home just minutes from the ...	5 beds \| 3 baths \| 2,850 sq.ft.	$275,000	Airbnb cash on cash: 3.14% Traditional cash on cash: 8.65% Airbnb Rental Income: $1889 Traditional Rental Income: $2814 Airbnb ROI: 3.14% Traditional ROI: 8.65%
17 N Randolph Street Indianapolis , IN Step into this beautifully maintained classic Four Square home offering timeless charm wit...	3 beds \| 2 baths \| 1,822 sq.ft.	$265,000	Airbnb cash on cash: -0.16% Traditional cash on cash: 5.95% Airbnb Rental Income: $843 Traditional Rental Income: $2041 Airbnb ROI: -0.16% Traditional ROI: 5.95%
2016 N Glenridge Drive Indianapolis , IN Charming "Updated" Bungalow will have you at Hello! This spacious 4-bedroom home offers un...	4 beds \| 1 baths \| 1,492 sq.ft.	$205,000	Airbnb cash on cash: 2.62% Traditional cash on cash: 3.88% Airbnb Rental Income: $1380 Traditional Rental Income: $1205 Airbnb ROI: 2.62% Traditional ROI: 3.88%
1444 E Elbert Street Indianapolis , IN Discover the perfect blend of charm and convenience at 1444 E Elbert Street. This inviting...	2 beds \| 1 baths \| 912 sq.ft.	$190,000	Airbnb cash on cash: 1.19% Traditional cash on cash: 3.59% Airbnb Rental Income: $1138 Traditional Rental Income: $1193 Airbnb ROI: 1.19% Traditional ROI: 3.59%
3822 Limelight Lane Whitestown , IN Nestled in Whitestown's desirable Walker Farms community, this 3-bedroom, 2.5-bath home of...	3 beds \| 3 baths \| 1,912 sq.ft.	$315,000	Airbnb cash on cash: 2% Traditional cash on cash: 5.39% Airbnb Rental Income: $1655 Traditional Rental Income: $2195 Airbnb ROI: 2% Traditional ROI: 5.39%
4111 W Peachtree Lane Muncie , IN Welcome to this charming 3 bed, 2 bath ranch-style home featuring a beautifully refinished...	3 beds \| 2 baths \| 1,806 sq.ft.	$229,900	Airbnb cash on cash: 2.7% Traditional cash on cash: 7.65% Airbnb Rental Income: $1450 Traditional Rental Income: $2097 Airbnb ROI: 2.7% Traditional ROI: 7.65%
1140 Hoyt Avenue Indianapolis , IN Welcome to 1140 Hoyt Ave-an updated 4-bedroom, 1.5-bath home located just minutes from the...	4 beds \| 2 baths \| 1,831 sq.ft.	$295,000	Airbnb cash on cash: 0.79% Traditional cash on cash: 3.95% Airbnb Rental Income: $1216 Traditional Rental Income: $1703 Airbnb ROI: 0.79% Traditional ROI: 3.95%
429 N Pennsylvania Street #904 Indianapolis , IN Must See!! Luxurious downtown 2 bed / 2.5 bath 9th floor penthouse condo in popular Resid...	2 beds \| 3 baths \| 2,745 sq.ft.	$1,395,000	Airbnb cash on cash: -2.89% Traditional cash on cash: -1.23% Airbnb Rental Income: $943 Traditional Rental Income: $2760 Airbnb ROI: -2.89% Traditional ROI: -1.23%
5626 Massachusetts Street Merrillville , IN Welcome to your perfect starter home or investment property! This 1,536 sq. ft. two-story ...	3 beds \| 2 baths \| 1,536 sq.ft.	$199,900	Airbnb cash on cash: 8.71% Traditional cash on cash: 6.47% Airbnb Rental Income: $3018 Traditional Rental Income: $1901 Airbnb ROI: 8.71% Traditional ROI: 6.47%

Real Estate investment in Winchester, IN

There are 0 properties for sale in the city of Winchester . The median list price in Winchester is $163,950 and the average price per square foot is $109. In October 2025, the average monthly cash on cash return in Winchester is 10.00%. The average monthly rental income in Winchester is $1,829.

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

There are 0 investment properties available for sale in Winchester.

The ROI for Short-Term is higher than the Long-Term in Winchester with average rental income of $N/A.

Your search for investment property begins and ends here

Investment Property for Sale in Winchester, IN

Other Investment Properties for Sale in Indiana

Indianapolis , IN

4 beds | 2 baths | 2,122 sq.ft.

$370,000

Airbnb cash on cash: 0.94%

Traditional cash on cash: 5.01%

Airbnb Rental Income: $1253

Traditional Rental Income: $2267

Airbnb ROI: 0.94%

Traditional ROI: 5.01%

Noblesville , IN

2 beds | 2 baths | 1,718 sq.ft.

$374,900

Airbnb cash on cash: -0.09%

Traditional cash on cash: 3.54%

Airbnb Rental Income: $1372

Traditional Rental Income: $2230

Airbnb ROI: -0.09%

Traditional ROI: 3.54%

Advance , IN

2 beds | 2 baths | 1,056 sq.ft.

$184,900

Airbnb cash on cash: N/A

Traditional cash on cash: 8.58%

Airbnb Rental Income: $null

Traditional Rental Income: $1851

Airbnb ROI: N/A

Traditional ROI: 8.58%

McCordsville , IN

3 beds | 3 baths | 2,263 sq.ft.

$379,900

Airbnb cash on cash: 0.89%

Traditional cash on cash: 4.12%

Airbnb Rental Income: $1588

Traditional Rental Income: $2283

Airbnb ROI: 0.89%

Traditional ROI: 4.12%

Indianapolis , IN

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

$325,000

Airbnb cash on cash: 2.49%

Traditional cash on cash: 5.93%

Airbnb Rental Income: $1861

Traditional Rental Income: $2413

Airbnb ROI: 2.49%

Traditional ROI: 5.93%

Indianapolis , IN

3 beds | 2 baths | 1,328 sq.ft.

$265,000

Airbnb cash on cash: 2.22%

Traditional cash on cash: 5.02%

Airbnb Rental Income: $1396

Traditional Rental Income: $1674

Airbnb ROI: 2.22%

Traditional ROI: 5.02%

Indianapolis , IN

5 beds | 3 baths | 2,850 sq.ft.

$275,000

Airbnb cash on cash: 3.14%

Traditional cash on cash: 8.65%

Airbnb Rental Income: $1889

Traditional Rental Income: $2814

Airbnb ROI: 3.14%

Traditional ROI: 8.65%

Indianapolis , IN

3 beds | 2 baths | 1,822 sq.ft.

$265,000

Airbnb cash on cash: -0.16%

Traditional cash on cash: 5.95%

Airbnb Rental Income: $843

Traditional Rental Income: $2041

Airbnb ROI: -0.16%

Traditional ROI: 5.95%

Indianapolis , IN

4 beds | 1 baths | 1,492 sq.ft.

$205,000

Airbnb cash on cash: 2.62%

Traditional cash on cash: 3.88%

Airbnb Rental Income: $1380