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: 3.05% Traditional cash on cash: 2.97% Airbnb Rental Income: $1394 Traditional Rental Income: $958 Airbnb ROI: 3.05% Traditional ROI: 2.97%
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: 5.12% Traditional cash on cash: 5.93% Airbnb Rental Income: $1394 Traditional Rental Income: $1073 Airbnb ROI: 5.12% Traditional ROI: 5.93%
1611 E Range Line Road Greencastle, IN Back on the Market due to no fault of the seller. Home priced well below appraised value t...	4 beds \| 2 baths \| 2,015 sq.ft.	$280,000	Airbnb cash on cash: 6.35% Traditional cash on cash: 6.89% Airbnb Rental Income: $2779 Traditional Rental Income: $2271 Airbnb ROI: 6.35% Traditional ROI: 6.89%
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: 4.88% Traditional cash on cash: 8.11% Airbnb Rental Income: $1680 Traditional Rental Income: $1823 Airbnb ROI: 4.88% 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.	$364,000	Airbnb cash on cash: 4.11% Traditional cash on cash: 3.89% Airbnb Rental Income: $2779 Traditional Rental Income: $2052 Airbnb ROI: 4.11% Traditional ROI: 3.89%
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.	$169,900	Airbnb cash on cash: 1.49% Traditional cash on cash: 5.09% Airbnb Rental Income: $986 Traditional Rental Income: $1215 Airbnb ROI: 1.49% Traditional ROI: 5.09%
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.	$285,900	Airbnb cash on cash: 5.71% Traditional cash on cash: 8.02% Airbnb Rental Income: $2779 Traditional Rental Income: $2751 Airbnb ROI: 5.71% Traditional ROI: 8.02%
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: 0.9% Traditional cash on cash: 4.25% Airbnb Rental Income: $1680 Traditional Rental Income: $2249 Airbnb ROI: 0.9% 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: 2.13% Traditional cash on cash: 5.22% Airbnb Rental Income: $1394 Traditional Rental Income: $1816 Airbnb ROI: 2.13% Traditional ROI: 5.22%
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.	$254,500	Airbnb cash on cash: 3.45% Traditional cash on cash: 5.1% Airbnb Rental Income: $1680 Traditional Rental Income: $1607 Airbnb ROI: 3.45% Traditional ROI: 5.1%
718 Highwood Avenue Greencastle, IN Step into this beautifully updated 4-bedroom, 2.5-bath residence that perfectly blends com...	4 beds \| 3 baths \| 2,128 sq.ft.	$375,000	Airbnb cash on cash: 4.32% Traditional cash on cash: 5.38% Airbnb Rental Income: $2779 Traditional Rental Income: $2500 Airbnb ROI: 4.32% Traditional ROI: 5.38%
1193 W CR 125 S Greencastle, IN Here's your chance to own this historic home on 1.13 acres. Step back in time and imagine ...	5 beds \| 2 baths \| 3,093 sq.ft.	$199,900	Airbnb cash on cash: N/A Traditional cash on cash: 8.21% Airbnb Rental Income: $null Traditional Rental Income: $1957 Airbnb ROI: N/A Traditional ROI: 8.21%
3247 W County Road 100 S Greencastle, IN Experience the perfect blend of country charm and modern luxury in this beautifully remode...	4 beds \| 4 baths \| 2,628 sq.ft.	$429,900	Airbnb cash on cash: 3.68% Traditional cash on cash: 5.33% Airbnb Rental Income: $2779 Traditional Rental Income: $2790 Airbnb ROI: 3.68% Traditional ROI: 5.33%
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: 9.18% Traditional cash on cash: 11.05% Airbnb Rental Income: $2779 Traditional Rental Income: $2482 Airbnb ROI: 9.18% Traditional ROI: 11.05%
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 \| N/A	$300,000	Airbnb cash on cash: 5.81% Traditional cash on cash: 6.96% Airbnb Rental Income: $2779 Traditional Rental Income: $2452 Airbnb ROI: 5.81% Traditional ROI: 6.96%
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: 3.19% Traditional cash on cash: 6.54% Airbnb Rental Income: $1680 Traditional Rental Income: $1954 Airbnb ROI: 3.19% Traditional ROI: 6.54%
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: 5.65% Traditional cash on cash: 6.9% Airbnb Rental Income: $1394 Traditional Rental Income: $1117 Airbnb ROI: 5.65% Traditional ROI: 6.9%
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: 1.43% Traditional cash on cash: 6.78% Airbnb Rental Income: $1394 Traditional Rental Income: $1977 Airbnb ROI: 1.43% Traditional ROI: 6.78%
890 Rockville Road Greencastle, IN Discover the charm of single-story living at 890 Rockville RD, GREENCASTLE, IN. Built in 1...	3 beds \| 1 baths \| 960 sq.ft.	$140,000	Airbnb cash on cash: 6.28% Traditional cash on cash: 6.03% Airbnb Rental Income: $1680 Traditional Rental Income: $1177 Airbnb ROI: 6.28% Traditional ROI: 6.03%
1611 W County Road 300 S Greencastle, IN This home has it all including a pool! 3 bedroom, 2.5 bath home with a great floorplan and...	3 beds \| 3 baths \| 3,732 sq.ft.	$419,000	Airbnb cash on cash: 1.77% Traditional cash on cash: 5.2% Airbnb Rental Income: $1680 Traditional Rental Income: $2560 Airbnb ROI: 1.77% Traditional ROI: 5.2%
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: 1.22% Traditional cash on cash: 2.26% Airbnb Rental Income: $2779 Traditional Rental Income: $2805 Airbnb ROI: 1.22% 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 $201,879 and the average price per square foot is $106. In July 2026, the average monthly cash on cash return in Greencastle is 6.00%. The average monthly rental income in Greencastle is $1,957.

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 $1,957.

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: 3.05%

Traditional cash on cash: 2.97%

Airbnb Rental Income: $1394

Traditional Rental Income: $958

Airbnb ROI: 3.05%

Traditional ROI: 2.97%

5075 Van Bibber Lake Estate

Greencastle, IN

2 beds | 1 baths | 644 sq.ft.

$128,000

Airbnb cash on cash: 5.12%

Traditional cash on cash: 5.93%

Airbnb Rental Income: $1394

Traditional Rental Income: $1073

Airbnb ROI: 5.12%

Traditional ROI: 5.93%

1611 E Range Line Road

Greencastle, IN

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

$280,000

Airbnb cash on cash: 6.35%

Traditional cash on cash: 6.89%

Airbnb Rental Income: $2779

Traditional Rental Income: $2271

Airbnb ROI: 6.35%

Traditional ROI: 6.89%

1158 W US HWY 40

Greencastle, IN

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

$199,900

Airbnb cash on cash: 4.88%

Traditional cash on cash: 8.11%

Airbnb Rental Income: $1680

Traditional Rental Income: $1823

Airbnb ROI: 4.88%

Traditional ROI: 8.11%

32 Edgelea Drive

Greencastle, IN

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

$364,000

Airbnb cash on cash: 4.11%

Traditional cash on cash: 3.89%

Airbnb Rental Income: $2779

Traditional Rental Income: $2052

Airbnb ROI: 4.11%

Traditional ROI: 3.89%

4016 Van Bibber Lake Estate

Greencastle, IN

1 beds | 1 baths | 608 sq.ft.

$169,900

Airbnb cash on cash: 1.49%

Traditional cash on cash: 5.09%

Airbnb Rental Income: $986

Traditional Rental Income: $1215

Airbnb ROI: 1.49%

Traditional ROI: 5.09%

700 Albin Pond Road

Greencastle, IN

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

$285,900

Airbnb cash on cash: 5.71%

Traditional cash on cash: 8.02%

Airbnb Rental Income: $2779

Traditional Rental Income: $2751

Airbnb ROI: 5.71%

Traditional ROI: 8.02%

464 Glenview Drive

Greencastle, IN

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

$329,900

Airbnb cash on cash: 0.9%

Traditional cash on cash: 4.25%

Airbnb Rental Income: $1680

Traditional Rental Income: $2249

Airbnb ROI: 0.9%