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
6476 W Range Line Road Greencastle, IN Welcome to your own private retreat! This beautiful 4-bedroom, 2-bathroom home sits on 11 ...	4 beds \| 2 baths \| 3,079 sq.ft.	$550,000	Airbnb cash on cash: 3.24% Traditional cash on cash: 3.24% Airbnb Rental Income: $3181 Traditional Rental Income: $2462 Airbnb ROI: 3.24% Traditional ROI: 3.24%
96 Kingswood Court Greencastle, IN Welcome to this beautiful and unique home in a well-established neighborhood! This propert...	4 beds \| 3 baths \| 2,868 sq.ft.	$394,900	Airbnb cash on cash: 5.04% Traditional cash on cash: 4.01% Airbnb Rental Income: $3181 Traditional Rental Income: $2081 Airbnb ROI: 5.04% Traditional ROI: 4.01%
4168 S County Road 325 W Greencastle, IN If you've been dreaming of space to roam, room to play, and a home that feels like a getaw...	3 beds \| 2 baths \| 1,320 sq.ft.	$279,900	Airbnb cash on cash: 3.83% Traditional cash on cash: 6.76% Airbnb Rental Income: $1938 Traditional Rental Income: $2199 Airbnb ROI: 3.83% Traditional ROI: 6.76%
1747 E Tall Oaks Lane Greencastle, IN Escape to this 3,392 SF, 4-bedroom, 4.5-bath rustic retreat nestled in the woods on a shar...	4 beds \| 5 baths \| 3,392 sq.ft.	$620,000	Airbnb cash on cash: 2.83% Traditional cash on cash: 7.86% Airbnb Rental Income: $3181 Traditional Rental Income: $5372 Airbnb ROI: 2.83% Traditional ROI: 7.86%
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: 0.85% Traditional cash on cash: 1.63% Airbnb Rental Income: $1938 Traditional Rental Income: $1852 Airbnb ROI: 0.85% Traditional ROI: 1.63%
5075 Van Bibber Lake 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.	$132,000	Airbnb cash on cash: 6.19% Traditional cash on cash: 5.73% Airbnb Rental Income: $1584 Traditional Rental Income: $1073 Airbnb ROI: 6.19% Traditional ROI: 5.73%
211 S Bloomington Street Greencastle, IN Historic Home less than one block from DePauw University main entrance! This 4 bedroom hom...	4 beds \| 2 baths \| 1,916 sq.ft.	$249,900	Airbnb cash on cash: 8.6% Traditional cash on cash: 8.69% Airbnb Rental Income: $3181 Traditional Rental Income: $2482 Airbnb ROI: 8.6% Traditional ROI: 8.69%
125 Woodland Greencastle, IN Back on the market with over $100,000 worth of improvements! Hard to beat everything this ...	3 beds \| 2 baths \| 2,186 sq.ft.	$399,000	Airbnb cash on cash: 2.18% Traditional cash on cash: 5.13% Airbnb Rental Income: $1938 Traditional Rental Income: $2533 Airbnb ROI: 2.18% Traditional ROI: 5.13%
205 N Jackson Street Greencastle, IN Discover this charming 2-bedroom, 1-bath home just one block from downtown Greencastle, of...	2 beds \| 1 baths \| 978 sq.ft.	$139,000	Airbnb cash on cash: 4.54% Traditional cash on cash: 5.42% Airbnb Rental Income: $1584 Traditional Rental Income: $1249 Airbnb ROI: 4.54% Traditional ROI: 5.42%
408 E Hanna Street Greencastle, IN Investment opportunity! This 2 story home is located close to the university and is ready ...	3 beds \| 1 baths \| 2,726 sq.ft.	$115,000	Airbnb cash on cash: 9.47% Traditional cash on cash: 10.23% Airbnb Rental Income: $1938 Traditional Rental Income: $1510 Airbnb ROI: 9.47% Traditional ROI: 10.23%
461 Harvest Moon Drive Greencastle, IN Charming One-Level Condo with Private, Tranquil Patio in Autumn Glen Village! Welcome to ...	2 beds \| 2 baths \| 1,226 sq.ft.	$225,000	Airbnb cash on cash: 2.15% Traditional cash on cash: 5.31% Airbnb Rental Income: $1584 Traditional Rental Income: $1804 Airbnb ROI: 2.15% Traditional ROI: 5.31%
403 E Hanna Street Greencastle, IN Welcome home! Nestled in the heart of DePauw's campus at 403 E Hanna ST, GREENCASTLE, IN, ...	3 beds \| 3 baths \| 2,152 sq.ft.	$299,000	Airbnb cash on cash: 3.53% Traditional cash on cash: 7.59% Airbnb Rental Income: $1938 Traditional Rental Income: $2569 Airbnb ROI: 3.53% Traditional ROI: 7.59%
602 S Illinois Street Greencastle, IN Brand New Classic! Easy Commute to DePauw University. This could be a great starter home o...	2 beds \| 1 baths \| 994 sq.ft.	$156,900	Airbnb cash on cash: 5.06% Traditional cash on cash: 4.79% Airbnb Rental Income: $1584 Traditional Rental Income: $1090 Airbnb ROI: 5.06% Traditional ROI: 4.79%
2057 S CR 900 W Greencastle, IN UPDATED: this home is NOW a 2 bath house!! Tucked away at 2057 S County Road 900 W in Gree...	3 beds \| 2 baths \| 2,688 sq.ft.	$270,000	Airbnb cash on cash: 3.97% Traditional cash on cash: 7.59% Airbnb Rental Income: $1938 Traditional Rental Income: $2349 Airbnb ROI: 3.97% Traditional ROI: 7.59%
513 Howard Street Greencastle, IN Rare investment opportunity! Here is your opportunity to buy your next duplex. Both units ...	N/A beds \| N/A baths \| N/A	$190,000	Airbnb cash on cash: 5.14% Traditional cash on cash: 3.25% Airbnb Rental Income: $1938 Traditional Rental Income: $1084 Airbnb ROI: 5.14% Traditional ROI: 3.25%
201 Longcastle Drive #APT 1 Greencastle, IN Beautifully Updated 2 Bedroom, 2 Bathroom Ranch-Style Condo. Welcome home to effortless l...	2 beds \| 2 baths \| 1,266 sq.ft.	$175,000	Airbnb cash on cash: 3.84% Traditional cash on cash: 6.97% Airbnb Rental Income: $1584 Traditional Rental Income: $1653 Airbnb ROI: 3.84% Traditional ROI: 6.97%
39 Martinsville Street Greencastle, IN 2 bedroom 1 full bath ranch home located in the heart of Greencastle. Home is in need of a...	2 beds \| 1 baths \| 1,184 sq.ft.	$125,000	Airbnb cash on cash: 6.87% Traditional cash on cash: 9.74% Airbnb Rental Income: $1584 Traditional Rental Income: $1477 Airbnb ROI: 6.87% Traditional ROI: 9.74%
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.	$194,900	Airbnb cash on cash: 4.46% Traditional cash on cash: 5.8% Airbnb Rental Income: $1584 Traditional Rental Income: $1379 Airbnb ROI: 4.46% Traditional ROI: 5.8%
1611 E Range Line Road Greencastle, IN Must see this spacious 2015 sq ft 4 bed/2 bath ranch style home with a generous sized yard...	4 beds \| 2 baths \| 2,015 sq.ft.	$310,000	Airbnb cash on cash: 6.8% Traditional cash on cash: 6.14% Airbnb Rental Income: $3181 Traditional Rental Income: $2271 Airbnb ROI: 6.8% Traditional ROI: 6.14%
1611 E Range Line Rd Greencastle, IN Must see this spacious 2015 sq ft 4 bed/2 bath ranch style home with a generous sized yard...	4 beds \| 3 baths \| 2,015 sq.ft.	$310,000	Airbnb cash on cash: 6.74% Traditional cash on cash: 6.71% Airbnb Rental Income: $3181 Traditional Rental Income: $2452 Airbnb ROI: 6.74% Traditional ROI: 6.71%
1158 W US HWY 40 Highway Greencastle, IN Country living at its finest! This 3-bedroom, 2-bath manufactured home sits on 12 beautifu...	3 beds \| 2 baths \| 1,632 sq.ft.	$549,900	Airbnb cash on cash: 1.59% Traditional cash on cash: 2.37% Airbnb Rental Income: $1938 Traditional Rental Income: $1823 Airbnb ROI: 1.59% Traditional ROI: 2.37%
404 Linwood Drive Greencastle, IN This spacious brick ranch is a must-see! With 5 bedrooms and 2 and 1/2 baths, there's room...	5 beds \| 3 baths \| 2,433 sq.ft.	$339,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.3% Airbnb Rental Income: $null Traditional Rental Income: $2891 Airbnb ROI: N/A Traditional ROI: 7.3%

Real Estate investment in Greencastle, IN

There are 22 properties for sale in the city of Greencastle . The median list price in Greencastle is $259,950 and the average price per square foot is $144. In December 2025, the average monthly cash on cash return in Greencastle is 6.00%. The average monthly rental income in Greencastle is $1,889.

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

There are 22 investment properties available for sale in Greencastle.

In 2025, 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 $1,889.

Your search for investment property begins and ends here

Investment Property for Sale in Greencastle, IN

6476 W Range Line Road

Greencastle, IN

4 beds | 2 baths | 3,079 sq.ft.

$550,000

Airbnb cash on cash: 3.24%

Traditional cash on cash: 3.24%

Airbnb Rental Income: $3181

Traditional Rental Income: $2462

Airbnb ROI: 3.24%

Traditional ROI: 3.24%

96 Kingswood Court

Greencastle, IN

4 beds | 3 baths | 2,868 sq.ft.

$394,900

Airbnb cash on cash: 5.04%

Traditional cash on cash: 4.01%

Airbnb Rental Income: $3181

Traditional Rental Income: $2081

Airbnb ROI: 5.04%

Traditional ROI: 4.01%

4168 S County Road 325 W

Greencastle, IN

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

$279,900

Airbnb cash on cash: 3.83%

Traditional cash on cash: 6.76%

Airbnb Rental Income: $1938

Traditional Rental Income: $2199

Airbnb ROI: 3.83%

Traditional ROI: 6.76%

1747 E Tall Oaks Lane

Greencastle, IN

4 beds | 5 baths | 3,392 sq.ft.

$620,000

Airbnb cash on cash: 2.83%

Traditional cash on cash: 7.86%

Airbnb Rental Income: $3181

Traditional Rental Income: $5372

Airbnb ROI: 2.83%

Traditional ROI: 7.86%

876 W County Road 25 S

Greencastle, IN

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

$585,000

Airbnb cash on cash: 0.85%

Traditional cash on cash: 1.63%

Airbnb Rental Income: $1938

Traditional Rental Income: $1852

Airbnb ROI: 0.85%

Traditional ROI: 1.63%

5075 Van Bibber Lake

Greencastle, IN

2 beds | 1 baths | 644 sq.ft.

$132,000

Airbnb cash on cash: 6.19%

Traditional cash on cash: 5.73%

Airbnb Rental Income: $1584

Traditional Rental Income: $1073

Airbnb ROI: 6.19%

Traditional ROI: 5.73%

211 S Bloomington Street

Greencastle, IN

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

$249,900

Airbnb cash on cash: 8.6%

Traditional cash on cash: 8.69%

Airbnb Rental Income: $3181

Traditional Rental Income: $2482

Airbnb ROI: 8.6%

Traditional ROI: 8.69%

125 Woodland

Greencastle, IN

3 beds | 2 baths | 2,186 sq.ft.

$399,000

Airbnb cash on cash: 2.18%

Traditional cash on cash: 5.13%

Airbnb Rental Income: $1938

Traditional Rental Income: $2533

Airbnb ROI: 2.18%