Real Estate Investment Properties for Sale in Greencastle, IN

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

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

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
876 W County Road 25 S Greencastle, IN Residential home & commercial building wrapped up into 1 amazing property! This 3 bedroom...	3 beds \| 2 baths \| 1,112 sq.ft.	$585,000	Airbnb cash on cash: 0.69% Traditional cash on cash: 1.63% Airbnb Rental Income: $1832 Traditional Rental Income: $1852 Airbnb ROI: 0.69% Traditional ROI: 1.63%
5075 Van Bibber Lake Estate Greencastle, IN Be part of the Lake Life Community at Van Bibber Lake Estates. This well-maintained home i...	2 beds \| 1 baths \| 644 sq.ft.	$128,000	Airbnb cash on cash: 4.26% Traditional cash on cash: 5.93% Airbnb Rental Income: $1268 Traditional Rental Income: $1073 Airbnb ROI: 4.26% Traditional ROI: 5.93%
211 S Bloomington Street Greencastle, IN Historic Home less than one block from DePauw University main entrance! This home include...	4 beds \| 2 baths \| 1,916 sq.ft.	$199,900	Airbnb cash on cash: 7.02% Traditional cash on cash: 11.05% Airbnb Rental Income: $2287 Traditional Rental Income: $2482 Airbnb ROI: 7.02% Traditional ROI: 11.05%
1611 E Range Line Road Greencastle, IN Spacious Ranch on Over an Acre - Perfect Blend of Comfort & Country Living! Welcome to 16...	4 beds \| 2 baths \| 2,015 sq.ft.	$300,000	Airbnb cash on cash: 4.41% Traditional cash on cash: 6.37% Airbnb Rental Income: $2287 Traditional Rental Income: $2271 Airbnb ROI: 4.41% Traditional ROI: 6.37%
1611 E Range Line Rd Greencastle, IN Spacious Ranch on Over an Acre - Perfect Blend of Comfort & Country Living! Welcome to 161...	4 beds \| 3 baths \| 2,015 sq.ft.	$300,000	Airbnb cash on cash: 4.36% Traditional cash on cash: 6.96% Airbnb Rental Income: $2287 Traditional Rental Income: $2452 Airbnb ROI: 4.36% Traditional ROI: 6.96%
1158 W US HWY 40 Highway Greencastle, IN Country living at its finest! This 3-bedroom, 2-bath manufactured home sits on 1.5 beautif...	3 beds \| 2 baths \| 1,632 sq.ft.	$199,900	Airbnb cash on cash: 5.55% Traditional cash on cash: 8.11% Airbnb Rental Income: $1832 Traditional Rental Income: $1823 Airbnb ROI: 5.55% Traditional ROI: 8.11%
3888 N County Road 800 W Greencastle, IN SELLER IS MOTIVATED AND WILLING TO OFFER CLOSING COST ASSISTANCE OR A RATE BUY-DOWN WITH A...	5 beds \| 3 baths \| 2,660 sq.ft.	$749,900	Airbnb cash on cash: N/A Traditional cash on cash: 1.12% Airbnb Rental Income: $null Traditional Rental Income: $2162 Airbnb ROI: N/A Traditional ROI: 1.12%
486 Glenview Drive Greencastle, IN Hard to find condo in the desirable Glenview Village. Condo has been well cared for and ha...	2 beds \| 2 baths \| 1,320 sq.ft.	$235,000	Airbnb cash on cash: 0.45% Traditional cash on cash: 5.2% Airbnb Rental Income: $1268 Traditional Rental Income: $1924 Airbnb ROI: 0.45% Traditional ROI: 5.2%
4016 Van Bibber Lake Estate Greencastle, IN This immaculate 1-bedroom, 1-bath home offers the perfect waterfront retreat and is sure t...	1 beds \| 1 baths \| 608 sq.ft.	$179,900	Airbnb cash on cash: 0.49% Traditional cash on cash: 4.71% Airbnb Rental Income: $817 Traditional Rental Income: $1215 Airbnb ROI: 0.49% Traditional ROI: 4.71%
700 Albin Pond Road Greencastle, IN Motivated sellers on this beautiful brown brick ranch home with full finished walkout base...	4 beds \| 3 baths \| 3,032 sq.ft.	$299,900	Airbnb cash on cash: 3.91% Traditional cash on cash: 7.57% Airbnb Rental Income: $2287 Traditional Rental Income: $2751 Airbnb ROI: 3.91% Traditional ROI: 7.57%
114 S Jackson Street Greencastle, IN Victorian Triplex. Renovation Started, Ready for Completion. Value-Add Opportunity. Unlock...	N/A beds \| N/A baths \| N/A	$174,900	Airbnb cash on cash: 0.86% Traditional cash on cash: 4.99% Airbnb Rental Income: $1029 Traditional Rental Income: $1357 Airbnb ROI: 0.86% Traditional ROI: 4.99%
690 Kirkwood Drive Greencastle, IN This charming home is nestled in a wonderful neighborhood on a peaceful 1.16 +-acre lot th...	5 beds \| 3 baths \| 3,366 sq.ft.	$399,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.01% Airbnb Rental Income: $null Traditional Rental Income: $2881 Airbnb ROI: N/A Traditional ROI: 6.01%
707 Shadowlawn Avenue Greencastle, IN Come and see this 3-bedroom, 2-bath home in a fantastic location! This move-in ready prope...	3 beds \| 2 baths \| 1,619 sq.ft.	$239,900	Airbnb cash on cash: 3.65% Traditional cash on cash: 6.36% Airbnb Rental Income: $1832 Traditional Rental Income: $1954 Airbnb ROI: 3.65% Traditional ROI: 6.36%
4735 W County Road 75 S Greencastle, IN This beautifully updated one-story ranch has been completely transformed since 2021, sitti...	3 beds \| 2 baths \| 1,786 sq.ft.	$349,900	Airbnb cash on cash: 1.94% Traditional cash on cash: 2.87% Airbnb Rental Income: $1832 Traditional Rental Income: $1641 Airbnb ROI: 1.94% Traditional ROI: 2.87%
108 E Berry Street Greencastle, IN Come check out this cute newly updated home on Berry St located minutes from Depauw and al...	2 beds \| 1 baths \| 984 sq.ft.	$150,000	Airbnb cash on cash: 3.64% Traditional cash on cash: 5.37% Airbnb Rental Income: $1268 Traditional Rental Income: $1117 Airbnb ROI: 3.64% Traditional ROI: 5.37%
464 Glenview Drive Greencastle, IN Presenting an inviting condominium residence at 464 Glenview DR, GREENCASTLE, IN, USA. Con...	3 beds \| 3 baths \| 3,326 sq.ft.	$329,900	Airbnb cash on cash: 1.31% Traditional cash on cash: 4.25% Airbnb Rental Income: $1832 Traditional Rental Income: $2249 Airbnb ROI: 1.31% Traditional ROI: 4.25%
314 N Madison St Greencastle, IN Discover the charm of this beautiful single-family 2BR/2BA home. Newly constructed in 2026...	2 beds \| 2 baths \| 1,273 sq.ft.	$289,900	Airbnb cash on cash: 1.75% Traditional cash on cash: 5.22% Airbnb Rental Income: $1268 Traditional Rental Income: $1816 Airbnb ROI: 1.75% Traditional ROI: 5.22%
2041 Fairway Drive Greencastle, IN This meticulously maintained single-family residence constructed in 1968, offering 2520 sq...	3 beds \| 3 baths \| 2,520 sq.ft.	$415,000	Airbnb cash on cash: 1.36% Traditional cash on cash: 3.23% Airbnb Rental Income: $1832 Traditional Rental Income: $2066 Airbnb ROI: 1.36% Traditional ROI: 3.23%
1649 W County Road 100 N Greencastle, IN Updated, spacious, & ready to impress! This 4-bedroom, 2-bath 2,858 square foot ranch feat...	4 beds \| 2 baths \| 2,858 sq.ft.	$390,000	Airbnb cash on cash: 3.16% Traditional cash on cash: 6.41% Airbnb Rental Income: $2287 Traditional Rental Income: $2905 Airbnb ROI: 3.16% Traditional ROI: 6.41%
123 Woods Edge Boulevard E Greencastle, IN **Discover this well maintained newer construction home at 123 Woods Edge Blvd E in the Wo...	3 beds \| 2 baths \| 1,282 sq.ft.	$267,000	Airbnb cash on cash: 3.38% Traditional cash on cash: 5.05% Airbnb Rental Income: $1832 Traditional Rental Income: $1760 Airbnb ROI: 3.38% Traditional ROI: 5.05%
880 Deer Field Drive Greencastle, IN Welcome home to this beautifully maintained 4-bedroom, 2.5-bath home located in one of the...	4 beds \| 3 baths \| 2,040 sq.ft.	$329,900	Airbnb cash on cash: 3.39% Traditional cash on cash: 3.91% Airbnb Rental Income: $2287 Traditional Rental Income: $1877 Airbnb ROI: 3.39% Traditional ROI: 3.91%
110 Howard Lane Greencastle, IN HOWARD YARD by Millennium Builders is Southern Indiana's first modernized, river-view deve...	4 beds \| 4 baths \| 2,737 sq.ft.	$699,000	Airbnb cash on cash: 0.59% Traditional cash on cash: 2.26% Airbnb Rental Income: $2287 Traditional Rental Income: $2805 Airbnb ROI: 0.59% Traditional ROI: 2.26%

Real Estate investment in Greencastle, IN

There are 22 properties for sale in the city of Greencastle . The median list price in Greencastle is $299,900 and the average price per square foot is $154. In May 2026, the average monthly cash on cash return in Greencastle is 5.00%. The average monthly rental income in Greencastle is $1,939.

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

There are 22 investment properties available for sale in Greencastle.

In 2026, the best neighborhood to buy investment property is Greencastle.

The ROI for Long-Term is higher than the Short-Term in Greencastle with average rental income of $1,939.

Your search for investment property begins and ends here

Investment Property for Sale in Greencastle, IN

876 W County Road 25 S

Greencastle, IN

3 beds | 2 baths | 1,112 sq.ft.

$585,000

Airbnb cash on cash: 0.69%

Traditional cash on cash: 1.63%

Airbnb Rental Income: $1832

Traditional Rental Income: $1852

Airbnb ROI: 0.69%

Traditional ROI: 1.63%

5075 Van Bibber Lake Estate

Greencastle, IN

2 beds | 1 baths | 644 sq.ft.

$128,000

Airbnb cash on cash: 4.26%

Traditional cash on cash: 5.93%

Airbnb Rental Income: $1268

Traditional Rental Income: $1073

Airbnb ROI: 4.26%

Traditional ROI: 5.93%

211 S Bloomington Street

Greencastle, IN

4 beds | 2 baths | 1,916 sq.ft.

$199,900

Airbnb cash on cash: 7.02%

Traditional cash on cash: 11.05%

Airbnb Rental Income: $2287

Traditional Rental Income: $2482

Airbnb ROI: 7.02%

Traditional ROI: 11.05%

1611 E Range Line Road

Greencastle, IN

4 beds | 2 baths | 2,015 sq.ft.

$300,000

Airbnb cash on cash: 4.41%

Traditional cash on cash: 6.37%

Airbnb Rental Income: $2287

Traditional Rental Income: $2271

Airbnb ROI: 4.41%

Traditional ROI: 6.37%

1611 E Range Line Rd

Greencastle, IN

4 beds | 3 baths | 2,015 sq.ft.

$300,000

Airbnb cash on cash: 4.36%

Traditional cash on cash: 6.96%

Airbnb Rental Income: $2287

Traditional Rental Income: $2452

Airbnb ROI: 4.36%

Traditional ROI: 6.96%

1158 W US HWY 40 Highway

Greencastle, IN

3 beds | 2 baths | 1,632 sq.ft.

$199,900

Airbnb cash on cash: 5.55%

Traditional cash on cash: 8.11%

Airbnb Rental Income: $1832

Traditional Rental Income: $1823

Airbnb ROI: 5.55%

Traditional ROI: 8.11%

3888 N County Road 800 W

Greencastle, IN

5 beds | 3 baths | 2,660 sq.ft.

$749,900

Airbnb cash on cash: N/A

Traditional cash on cash: 1.12%

Airbnb Rental Income: $null

Traditional Rental Income: $2162

Airbnb ROI: N/A

Traditional ROI: 1.12%

486 Glenview Drive

Greencastle, IN

2 beds | 2 baths | 1,320 sq.ft.

$235,000

Airbnb cash on cash: 0.45%

Traditional cash on cash: 5.2%

Airbnb Rental Income: $1268

Traditional Rental Income: $1924

Airbnb ROI: 0.45%