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
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%
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%
Investment Properties for Sale in Other Cities of Indiana
1702 Sunnyslope Drive Crown Point , IN Lakefront Luxury at Its Finest!Discover the ultimate lakefront lifestyle with this fully u...	3 beds \| 2 baths \| 2,120 sq.ft.	$540,000	Airbnb cash on cash: 2.08% Traditional cash on cash: 3.45% Airbnb Rental Income: $2704 Traditional Rental Income: $2756 Airbnb ROI: 2.08% Traditional ROI: 3.45%
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: 0.72% Traditional cash on cash: 2.85% Airbnb Rental Income: $2204 Traditional Rental Income: $2937 Airbnb ROI: 0.72% Traditional ROI: 2.85%
3738 Ruckle Street Indianapolis , IN Check out this 3 bedroom 1 1/2 bath home with an all new kitchen including stainless steel...	3 beds \| 2 baths \| 2,588 sq.ft.	$320,000	Airbnb cash on cash: 3.93% Traditional cash on cash: 5.12% Airbnb Rental Income: $2424 Traditional Rental Income: $2190 Airbnb ROI: 3.93% Traditional ROI: 5.12%
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: 2.63% Traditional cash on cash: 4.14% Airbnb Rental Income: $2930 Traditional Rental Income: $2955 Airbnb ROI: 2.63% 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.	$325,000	Airbnb cash on cash: 4.54% Traditional cash on cash: 5.37% Airbnb Rental Income: $2557 Traditional Rental Income: $2194 Airbnb ROI: 4.54% Traditional ROI: 5.37%
802 N Tuxedo Street Indianapolis , IN Welcome to this beautifully remodeled 3-bedroom, 2-bath home just minutes from downtown In...	3 beds \| 2 baths \| 1,063 sq.ft.	$230,000	Airbnb cash on cash: 1.61% Traditional cash on cash: 4.69% Airbnb Rental Income: $1240 Traditional Rental Income: $1514 Airbnb ROI: 1.61% Traditional ROI: 4.69%
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%
1121 N Parker Avenue Indianapolis , IN This home seamlessly blends timeless charm and character with modern updates and convenien...	4 beds \| 3 baths \| 2,342 sq.ft.	$299,000	Airbnb cash on cash: 1.26% Traditional cash on cash: 7.49% Airbnb Rental Income: $1386 Traditional Rental Income: $2721 Airbnb ROI: 1.26% Traditional ROI: 7.49%
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: 0.41% Traditional cash on cash: 2.5% Airbnb Rental Income: $1859 Traditional Rental Income: $2273 Airbnb ROI: 0.41% 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: 1.48% Traditional cash on cash: 4.26% Airbnb Rental Income: $2204 Traditional Rental Income: $2948 Airbnb ROI: 1.48% Traditional ROI: 4.26%
2919 E New York Street Indianapolis , IN Great opportunity to purchase a property surrounded by development and growth. There are f...	4 beds \| 1 baths \| 1,236 sq.ft.	$144,000	Airbnb cash on cash: 4.78% Traditional cash on cash: 9.34% Airbnb Rental Income: $1386 Traditional Rental Income: $1595 Airbnb ROI: 4.78% Traditional ROI: 9.34%
1902 Woodlawn Avenue Indianapolis , IN Step into this beautifully and full of character gem in Fountain Square. Lovingly preserve...	4 beds \| 2 baths \| 2,016 sq.ft.	$365,000	Airbnb cash on cash: 4.08% Traditional cash on cash: 4.42% Airbnb Rental Income: $2775 Traditional Rental Income: $2241 Airbnb ROI: 4.08% Traditional ROI: 4.42%
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.	$199,900	Airbnb cash on cash: 8.92% Traditional cash on cash: 8.06% Airbnb Rental Income: $2663 Traditional Rental Income: $1867 Airbnb ROI: 8.92% Traditional ROI: 8.06%
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%

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 $98. In December 2024, the average monthly cash on cash return in Winchester is 11.00%. The average monthly rental income in Winchester is $2,208.

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

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%

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%

Investment Properties for Sale in Other Cities of Indiana

Crown Point , IN

3 beds | 2 baths | 2,120 sq.ft.

$540,000

Airbnb cash on cash: 2.08%

Traditional cash on cash: 3.45%

Airbnb Rental Income: $2704

Traditional Rental Income: $2756

Airbnb ROI: 2.08%

Traditional ROI: 3.45%

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: 0.72%

Traditional cash on cash: 2.85%

Airbnb Rental Income: $2204

Traditional Rental Income: $2937

Airbnb ROI: 0.72%

Traditional ROI: 2.85%

Indianapolis , IN

3 beds | 2 baths | 2,588 sq.ft.

$320,000

Airbnb cash on cash: 3.93%

Traditional cash on cash: 5.12%

Airbnb Rental Income: $2424

Traditional Rental Income: $2190

Airbnb ROI: 3.93%

Traditional ROI: 5.12%

Indianapolis , IN

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

$497,000

Airbnb cash on cash: 2.63%

Traditional cash on cash: 4.14%

Airbnb Rental Income: $2930

Traditional Rental Income: $2955

Airbnb ROI: 2.63%

Traditional ROI: 4.14%

Indianapolis , IN

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

$325,000