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
942 E Short Street Winchester, IN Check out this charming 2 bed, 1 bath home in Winchester! This home has baseboard heating,...	2 beds \| 1 baths \| 1,006 sq.ft.	$129,900	Airbnb cash on cash: 6.76% Traditional cash on cash: 10.79% Airbnb Rental Income: $1597 Traditional Rental Income: $1645 Airbnb ROI: 6.76% Traditional ROI: 10.79%
892 S 125 E Winchester, IN Welcome home! Nestled on 2.24 acres, this charming four-bedroom, two-bathroom home offers ...	4 beds \| 2 baths \| 2,352 sq.ft.	$239,900	Airbnb cash on cash: N/A Traditional cash on cash: 10.35% Airbnb Rental Income: $null Traditional Rental Income: $2788 Airbnb ROI: N/A Traditional ROI: 10.35%
635 E 225 N Winchester, IN Take a look at this beautiful 3 bedroom 2 bathroom home!! This home has been recently remo...	3 beds \| 2 baths \| 2,027 sq.ft.	$344,900	Airbnb cash on cash: 6.34% Traditional cash on cash: 6.46% Airbnb Rental Income: $3305 Traditional Rental Income: $2604 Airbnb ROI: 6.34% Traditional ROI: 6.46%
Investment Properties for Sale in Other Cities of Indiana
2190 Old Orchard Drive West Harrison , IN Welcome to your dream home in the desirable Old Orchard neighborhood! This inviting reside...	3 beds \| 3 baths \| 1,990 sq.ft.	$365,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.21% Airbnb Rental Income: $null Traditional Rental Income: $2510 Airbnb ROI: N/A Traditional ROI: 5.21%
157 W Norway Road Monticello , IN Here is your chance to own a great 2 bedroom, 1 bathroom home that has a full basement, la...	2 beds \| 1 baths \| 1,159 sq.ft.	$119,900	Airbnb cash on cash: 8.49% Traditional cash on cash: 9.63% Airbnb Rental Income: $1770 Traditional Rental Income: $1418 Airbnb ROI: 8.49% Traditional ROI: 9.63%
605 S Ryle Drive Greensburg , IN Discover this updated gem featuring 3 bedrooms and 1.5 baths, located in desirable Ryle Ad...	3 beds \| 2 baths \| 1,372 sq.ft.	$249,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.07% Airbnb Rental Income: $null Traditional Rental Income: $1861 Airbnb ROI: N/A Traditional ROI: 6.07%
665 E 9th Street Indianapolis , IN Terrific opportunity in ideal location! Two minute walk from BOTH Mass Ave and Bottle Wor...	3 beds \| 4 baths \| 2,973 sq.ft.	$650,000	Airbnb cash on cash: 0.43% Traditional cash on cash: 2.85% Airbnb Rental Income: $1991 Traditional Rental Income: $2937 Airbnb ROI: 0.43% Traditional ROI: 2.85%
9063 Dewberry Court Indianapolis , IN Escape from the ordinary in this unique multi-level 4bed/2.5bath home located in the heart...	4 beds \| 3 baths \| 3,490 sq.ft.	$497,000	Airbnb cash on cash: 3.74% Traditional cash on cash: 4.14% Airbnb Rental Income: $3550 Traditional Rental Income: $2955 Airbnb ROI: 3.74% Traditional ROI: 4.14%
1644 Fletcher Avenue Indianapolis , IN Welcome to this stunning gem in the heart of Fountain Square! Immerse yourself in the vibr...	3 beds \| 3 baths \| 1,896 sq.ft.	$330,000	Airbnb cash on cash: 4.46% Traditional cash on cash: 5.27% Airbnb Rental Income: $2557 Traditional Rental Income: $2194 Airbnb ROI: 4.46% Traditional ROI: 5.27%
5934 Pine Bluff Drive Avon , IN This home features a grand open layout on the main floor, with a spacious great room seaml...	4 beds \| 3 baths \| 3,989 sq.ft.	$425,000	Airbnb cash on cash: 2.57% Traditional cash on cash: 4.64% Airbnb Rental Income: $2448 Traditional Rental Income: $2673 Airbnb ROI: 2.57% Traditional ROI: 4.64%
9276 E Parke Place Rockville , IN Turn-Key 4 Bedroom, 2 Full Bath, Walk-out Basement, Amish Built, locally harvested Timber ...	4 beds \| 2 baths \| 2,408 sq.ft.	$430,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.34% Airbnb Rental Income: $null Traditional Rental Income: $2398 Airbnb ROI: N/A Traditional ROI: 4.34%
5625 Gateway E Drive Whitestown , IN Highly Desirable Ranch Home in Clark Meadows at Anson This move-in ready, single-level ra...	3 beds \| 3 baths \| 2,336 sq.ft.	$405,000	Airbnb cash on cash: 1.66% Traditional cash on cash: 5.13% Airbnb Rental Income: $2014 Traditional Rental Income: $2806 Airbnb ROI: 1.66% Traditional ROI: 5.13%
503 Lockerbie Circle N Indianapolis , IN Lockerbie Glove Townhouse! Aha! You have found the perfect (yet elusive!) Downtown hom...	2 beds \| 3 baths \| 1,875 sq.ft.	$465,000	Airbnb cash on cash: 1.71% Traditional cash on cash: 2.5% Airbnb Rental Income: $2538 Traditional Rental Income: $2273 Airbnb ROI: 1.71% Traditional ROI: 2.5%
938 N Alabama Street Indianapolis , IN Beautiful 3 Bedroom 3.5 Bath Historical Home. Located in St. Joseph district. Totally ren...	3 beds \| 4 baths \| 2,628 sq.ft.	$499,990	Airbnb cash on cash: 1.1% Traditional cash on cash: 4.26% Airbnb Rental Income: $1991 Traditional Rental Income: $2948 Airbnb ROI: 1.1% Traditional ROI: 4.26%
1236 Cheshire Drive Indianapolis , IN Welcome home to this recently remodeled bi-level, featuring 3 bedrooms and 2 full baths. L...	3 beds \| 2 baths \| 1,404 sq.ft.	$204,900	Airbnb cash on cash: 9.93% Traditional cash on cash: 7.84% Airbnb Rental Income: $2954 Traditional Rental Income: $1867 Airbnb ROI: 9.93% Traditional ROI: 7.84%
3623 W 56th Street Indianapolis , IN Welcome to your dream home at 3623 West 56th Street in the heart of Indianapolis! This bea...	3 beds \| 2 baths \| 1,622 sq.ft.	$325,000	Airbnb cash on cash: 6.68% Traditional cash on cash: 4.76% Airbnb Rental Income: $3363 Traditional Rental Income: $2027 Airbnb ROI: 6.68% Traditional ROI: 4.76%
1332 Cliff Ridge Court Indianapolis , IN Welcome to this updated 3-bedroom, 2-bathroom home in the Perry Township area of Indianapo...	3 beds \| 2 baths \| 1,209 sq.ft.	$215,000	Airbnb cash on cash: 5.52% Traditional cash on cash: 7.65% Airbnb Rental Income: $2169 Traditional Rental Income: $2051 Airbnb ROI: 5.52% Traditional ROI: 7.65%
2812 Treviso Way Fort Wayne , IN Open House is CANCELLED due to accepted offer!!!!!!! Why buy new when you can own this exc...	3 beds \| 2 baths \| 1,754 sq.ft.	$359,900	Airbnb cash on cash: 3.79% Traditional cash on cash: 5.39% Airbnb Rental Income: $2581 Traditional Rental Income: $2500 Airbnb ROI: 3.79% Traditional ROI: 5.39%

Real Estate investment in Winchester, IN

There are 3 properties for sale in the city of Winchester . The median list price in Winchester is $169,900 and the average price per square foot is $99. In November 2024, the average monthly cash on cash return in Winchester is 10.00%. The average monthly rental income in Winchester is $1,983.

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

There are 3 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 $3,305.

Your search for investment property begins and ends here

Investment Property for Sale in Winchester, IN

942 E Short Street

Winchester, IN

2 beds | 1 baths | 1,006 sq.ft.

$129,900

Airbnb cash on cash: 6.76%

Traditional cash on cash: 10.79%

Airbnb Rental Income: $1597

Traditional Rental Income: $1645

Airbnb ROI: 6.76%

Traditional ROI: 10.79%

892 S 125 E

Winchester, IN

4 beds | 2 baths | 2,352 sq.ft.

$239,900

Airbnb cash on cash: N/A

Traditional cash on cash: 10.35%

Airbnb Rental Income: $null

Traditional Rental Income: $2788

Airbnb ROI: N/A

Traditional ROI: 10.35%

635 E 225 N

Winchester, IN

3 beds | 2 baths | 2,027 sq.ft.

$344,900

Airbnb cash on cash: 6.34%

Traditional cash on cash: 6.46%

Airbnb Rental Income: $3305

Traditional Rental Income: $2604

Airbnb ROI: 6.34%

Traditional ROI: 6.46%

Investment Properties for Sale in Other Cities of Indiana

West Harrison , IN

3 beds | 3 baths | 1,990 sq.ft.

$365,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.21%

Airbnb Rental Income: $null

Traditional Rental Income: $2510

Airbnb ROI: N/A

Traditional ROI: 5.21%

Monticello , IN

2 beds | 1 baths | 1,159 sq.ft.

$119,900

Airbnb cash on cash: 8.49%

Traditional cash on cash: 9.63%

Airbnb Rental Income: $1770

Traditional Rental Income: $1418

Airbnb ROI: 8.49%

Traditional ROI: 9.63%

Greensburg , IN

3 beds | 2 baths | 1,372 sq.ft.

$249,900

Airbnb cash on cash: N/A

Traditional cash on cash: 6.07%

Airbnb Rental Income: $null

Traditional Rental Income: $1861

Airbnb ROI: N/A

Traditional ROI: 6.07%

Indianapolis , IN

3 beds | 4 baths | 2,973 sq.ft.

$650,000

Airbnb cash on cash: 0.43%

Traditional cash on cash: 2.85%

Airbnb Rental Income: $1991

Traditional Rental Income: $2937

Airbnb ROI: 0.43%

Traditional ROI: 2.85%

Indianapolis , IN

4 beds | 3 baths | 3,490 sq.ft.

$497,000

Airbnb cash on cash: 3.74%

Traditional cash on cash: 4.14%

Airbnb Rental Income: $3550

Traditional Rental Income: $2955

Airbnb ROI: 3.74%

Traditional ROI: 4.14%

Indianapolis , IN

3 beds | 3 baths | 1,896 sq.ft.

$330,000