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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
316 N College Avenue Greencastle, IN Completely remodeled and move-in ready! This charming 2-bedroom, 1-bath home on College Av...	2 beds \| 1 baths \| 922 sq.ft.	$189,900	Airbnb cash on cash: 2.47% Traditional cash on cash: 2.97% Airbnb Rental Income: $1268 Traditional Rental Income: $958 Airbnb ROI: 2.47% Traditional ROI: 2.97%
211 S Bloomington Street Greencastle, IN Historic Home less than one block from DePauw University main entrance! This home includes...	4 beds \| 2 baths \| 1,916 sq.ft.	$199,900	Airbnb cash on cash: 8.1% Traditional cash on cash: 11.05% Airbnb Rental Income: $2532 Traditional Rental Income: $2482 Airbnb ROI: 8.1% Traditional ROI: 11.05%
1158 W US HWY 40 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: 5.06% Traditional cash on cash: 8.11% Airbnb Rental Income: $1721 Traditional Rental Income: $1823 Airbnb ROI: 5.06% Traditional ROI: 8.11%
32 Edgelea Drive Greencastle, IN Discover a distinguished lifestyle at 32 Edgelea DR, Greencastle, IN. Built in 1975, this ...	4 beds \| 3 baths \| 3,080 sq.ft.	$375,000	Airbnb cash on cash: 3.35% Traditional cash on cash: 3.72% Airbnb Rental Income: $2532 Traditional Rental Income: $2052 Airbnb ROI: 3.35% Traditional ROI: 3.72%
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.	$734,900	Airbnb cash on cash: N/A Traditional cash on cash: 1.18% Airbnb Rental Income: $null Traditional Rental Income: $2162 Airbnb ROI: N/A Traditional ROI: 1.18%
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: 0.59% Traditional cash on cash: 4.71% Airbnb Rental Income: $838 Traditional Rental Income: $1215 Airbnb ROI: 0.59% 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: 4.63% Traditional cash on cash: 7.57% Airbnb Rental Income: $2532 Traditional Rental Income: $2751 Airbnb ROI: 4.63% Traditional ROI: 7.57%
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: 1.01% Traditional cash on cash: 4.25% Airbnb Rental Income: $1721 Traditional Rental Income: $2249 Airbnb ROI: 1.01% 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%
732 E Seminary Street Greencastle, IN Discover a lifestyle of comfortable ease in this inviting single-family residence, offers ...	2 beds \| 1 baths \| 816 sq.ft.	$179,900	Airbnb cash on cash: 2.69% Traditional cash on cash: 3.6% Airbnb Rental Income: $1268 Traditional Rental Income: $1025 Airbnb ROI: 2.69% Traditional ROI: 3.6%
1742 E Range Line Road Greencastle, IN Remodeled home located just outside the city limits of Greencastle on a beautiful lot with...	3 beds \| 2 baths \| 1,144 sq.ft.	$264,500	Airbnb cash on cash: 3.43% Traditional cash on cash: 4.88% Airbnb Rental Income: $1721 Traditional Rental Income: $1607 Airbnb ROI: 3.43% Traditional ROI: 4.88%
111 S Spring Street #G6 Greencastle, IN Don't miss out on this spacious, very private, and highly sought-after residence inside Gr...	2 beds \| 2 baths \| 1,625 sq.ft.	$197,500	Airbnb cash on cash: 0.87% Traditional cash on cash: 6.78% Airbnb Rental Income: $1268 Traditional Rental Income: $1977 Airbnb ROI: 0.87% Traditional ROI: 6.78%
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: 1.12% Traditional cash on cash: 3.23% Airbnb Rental Income: $1721 Traditional Rental Income: $2066 Airbnb ROI: 1.12% Traditional ROI: 3.23%
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.	$485,000	Airbnb cash on cash: 0.82% Traditional cash on cash: 2.16% Airbnb Rental Income: $1721 Traditional Rental Income: $1852 Airbnb ROI: 0.82% Traditional ROI: 2.16%
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: 3.72% Traditional cash on cash: 6.41% Airbnb Rental Income: $2532 Traditional Rental Income: $2905 Airbnb ROI: 3.72% Traditional ROI: 6.41%
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%
4082 W County Road 450 N Greencastle, IN Enjoy peaceful country living in this 2-bedroom, 1-bath home situated on 1.5 acres. This p...	2 beds \| 1 baths \| 1,500 sq.ft.	$179,900	Airbnb cash on cash: 3.37% Traditional cash on cash: 6.35% Airbnb Rental Income: $1268 Traditional Rental Income: $1379 Airbnb ROI: 3.37% Traditional ROI: 6.35%
1611 E Range Line Road Greencastle, IN Spacious Ranch on Over an Acre - Perfect Blend of Comfort & Country Living! Welcome to 161...	4 beds \| 2 baths \| 2,015 sq.ft.	$300,000	Airbnb cash on cash: 5.14% Traditional cash on cash: 6.37% Airbnb Rental Income: $2532 Traditional Rental Income: $2271 Airbnb ROI: 5.14% Traditional ROI: 6.37%
413 E Washington Street Greencastle, IN This single-family, 1.5 story 3 bedroom 2 full bath home in Putnam County presents an invi...	3 beds \| 2 baths \| 1,385 sq.ft.	$215,000	Airbnb cash on cash: 3.82% Traditional cash on cash: 7.06% Airbnb Rental Income: $1721 Traditional Rental Income: $1907 Airbnb ROI: 3.82% Traditional ROI: 7.06%
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%
2012 Windemere Drive Greencastle, IN Welcome to this beautifully maintained all-brick 3-bedroom, 2.5-bath home located in the w...	3 beds \| 3 baths \| 2,928 sq.ft.	$425,000	Airbnb cash on cash: 1.05% Traditional cash on cash: 4.33% Airbnb Rental Income: $1721 Traditional Rental Income: $2550 Airbnb ROI: 1.05% Traditional ROI: 4.33%
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: 2.06% Traditional cash on cash: 4.99% Airbnb Rental Income: $1270 Traditional Rental Income: $1357 Airbnb ROI: 2.06% Traditional ROI: 4.99%
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: 3.01% Traditional cash on cash: 5.05% Airbnb Rental Income: $1721 Traditional Rental Income: $1760 Airbnb ROI: 3.01% Traditional ROI: 5.05%
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%
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: 4.05% Traditional cash on cash: 3.91% Airbnb Rental Income: $2532 Traditional Rental Income: $1877 Airbnb ROI: 4.05% Traditional ROI: 3.91%
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.	$234,900	Airbnb cash on cash: 3.35% Traditional cash on cash: 6.54% Airbnb Rental Income: $1721 Traditional Rental Income: $1954 Airbnb ROI: 3.35% Traditional ROI: 6.54%
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: 1.66% Traditional cash on cash: 2.87% Airbnb Rental Income: $1721 Traditional Rental Income: $1641 Airbnb ROI: 1.66% 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.	$120,000	Airbnb cash on cash: 4.75% Traditional cash on cash: 6.9% Airbnb Rental Income: $1268 Traditional Rental Income: $1117 Airbnb ROI: 4.75% Traditional ROI: 6.9%
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: 0.9% Traditional cash on cash: 2.26% Airbnb Rental Income: $2532 Traditional Rental Income: $2805 Airbnb ROI: 0.9% Traditional ROI: 2.26%

Real Estate investment in Greencastle, IN

There are 29 properties for sale in the city of Greencastle . The median list price in Greencastle is $201,895 and the average price per square foot is $108. In June 2026, the average monthly cash on cash return in Greencastle is 5.00%. The average monthly rental income in Greencastle is $1,924.

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

There are 29 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 $1,924.

Your search for investment property begins and ends here

Investment Property for Sale in Greencastle, IN

316 N College Avenue

Greencastle, IN

2 beds | 1 baths | 922 sq.ft.

$189,900

Airbnb cash on cash: 2.47%

Traditional cash on cash: 2.97%

Airbnb Rental Income: $1268

Traditional Rental Income: $958

Airbnb ROI: 2.47%

Traditional ROI: 2.97%

211 S Bloomington Street

Greencastle, IN

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

$199,900

Airbnb cash on cash: 8.1%

Traditional cash on cash: 11.05%

Airbnb Rental Income: $2532

Traditional Rental Income: $2482

Airbnb ROI: 8.1%

Traditional ROI: 11.05%

1158 W US HWY 40

Greencastle, IN

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

$199,900

Airbnb cash on cash: 5.06%

Traditional cash on cash: 8.11%

Airbnb Rental Income: $1721

Traditional Rental Income: $1823

Airbnb ROI: 5.06%

Traditional ROI: 8.11%

32 Edgelea Drive

Greencastle, IN

4 beds | 3 baths | 3,080 sq.ft.

$375,000

Airbnb cash on cash: 3.35%

Traditional cash on cash: 3.72%

Airbnb Rental Income: $2532

Traditional Rental Income: $2052

Airbnb ROI: 3.35%

Traditional ROI: 3.72%

3888 N County Road 800 W

Greencastle, IN

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

$734,900

Airbnb cash on cash: N/A

Traditional cash on cash: 1.18%

Airbnb Rental Income: $null

Traditional Rental Income: $2162

Airbnb ROI: N/A

Traditional ROI: 1.18%

4016 Van Bibber Lake Estate

Greencastle, IN

1 beds | 1 baths | 608 sq.ft.

$179,900

Airbnb cash on cash: 0.59%

Traditional cash on cash: 4.71%

Airbnb Rental Income: $838

Traditional Rental Income: $1215

Airbnb ROI: 0.59%

Traditional ROI: 4.71%

700 Albin Pond Road

Greencastle, IN

4 beds | 3 baths | 3,032 sq.ft.

$299,900

Airbnb cash on cash: 4.63%

Traditional cash on cash: 7.57%

Airbnb Rental Income: $2532

Traditional Rental Income: $2751

Airbnb ROI: 4.63%

Traditional ROI: 7.57%

464 Glenview Drive

Greencastle, IN

3 beds | 3 baths | 3,326 sq.ft.

$329,900

Airbnb cash on cash: 1.01%

Traditional cash on cash: 4.25%

Airbnb Rental Income: $1721

Traditional Rental Income: $2249

Airbnb ROI: 1.01%