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
111 S Spring St #204 Greencastle, IN Adorable 2 bedroom, 2 full bath condo, in walking distance of DePauw University, Library, ...	2 beds \| 2 baths \| 1,087 sq.ft.	$174,900	Airbnb cash on cash: 1.65% Traditional cash on cash: 1.75% Airbnb Rental Income: $1442 Traditional Rental Income: $1030 Airbnb ROI: 1.65% Traditional ROI: 1.75%
724 N US 231 Hwy Greencastle, IN Don't miss out on this well-maintained brick home, just minutes away from town. This 3-bed...	3 beds \| 1 baths \| 1,624 sq.ft.	$270,000	Airbnb cash on cash: 3.29% Traditional cash on cash: 3.73% Airbnb Rental Income: $1736 Traditional Rental Income: $1369 Airbnb ROI: 3.29% Traditional ROI: 3.73%
1041 Shadowlawn Ave Greencastle, IN Immaculate and move in ready! Spacious 3 bedroom 3 full bath home. Large eat in kitchen ...	3 beds \| 3 baths \| 3,794 sq.ft.	$379,900	Airbnb cash on cash: 1.78% Traditional cash on cash: 3.36% Airbnb Rental Income: $1736 Traditional Rental Income: $1820 Airbnb ROI: 1.78% Traditional ROI: 3.36%
8 Paradise Ln Greencastle, IN Welcome home to this beautifully maintained all-brick 3-bedroom, 1.5-bath residence, where...	3 beds \| 1 baths \| 1,571 sq.ft.	$249,000	Airbnb cash on cash: 3.53% Traditional cash on cash: 4.06% Airbnb Rental Income: $1736 Traditional Rental Income: $1382 Airbnb ROI: 3.53% Traditional ROI: 4.06%
1747 E Tall Oaks Ln Greencastle, IN Escape to this 3,392 SF, 4-bedroom, 4.5-bath rustic retreat nestled in the woods on a shar...	4 beds \| 4 baths \| 3,392 sq.ft.	$482,500	Airbnb cash on cash: 3.95% Traditional cash on cash: 10.35% Airbnb Rental Income: $3207 Traditional Rental Income: $5372 Airbnb ROI: 3.95% Traditional ROI: 10.35%
3777 N Us Highway 231 Greencastle, IN 2 story farm-house sitting on 10+- acres. Several updates including a newer metal roof and...	4 beds \| 2 baths \| 4,431 sq.ft.	$415,000	Airbnb cash on cash: 4.96% Traditional cash on cash: 3.16% Airbnb Rental Income: $3207 Traditional Rental Income: $1784 Airbnb ROI: 4.96% Traditional ROI: 3.16%
136 W Berry St Greencastle, IN Almost a 1/2 acre right in town! This 3bd 1 1/2ba is move in ready! New Flooring, paint, ...	3 beds \| 1 baths \| 1,152 sq.ft.	$200,000	Airbnb cash on cash: 5.09% Traditional cash on cash: 7.18% Airbnb Rental Income: $1736 Traditional Rental Income: $1653 Airbnb ROI: 5.09% Traditional ROI: 7.18%
7 S Bloomington St Greencastle, IN Craftsman 4 bedroom, 2 bath home that greets you with a spacious entryway large enough to ...	4 beds \| 2 baths \| 5,786 sq.ft.	$249,900	Airbnb cash on cash: 8.64% Traditional cash on cash: 5.57% Airbnb Rental Income: $3207 Traditional Rental Income: $1757 Airbnb ROI: 8.64% Traditional ROI: 5.57%
29 Beveridge St Greencastle, IN Enjoy your Independence Day when you say goodbye to your landlord and hello to this remode...	3 beds \| 2 baths \| 1,669 sq.ft.	$210,000	Airbnb cash on cash: 4.65% Traditional cash on cash: 7.62% Airbnb Rental Income: $1736 Traditional Rental Income: $1849 Airbnb ROI: 4.65% Traditional ROI: 7.62%
109 W Liberty St Greencastle, IN Multi-Unit!! Here is your chance to own a triplex in the heart of Greencastle. Two 1 bedro...	4 beds \| N/A baths \| 2,794 sq.ft.	$119,900	Airbnb cash on cash: 8.25% Traditional cash on cash: 4.16% Airbnb Rental Income: $1736 Traditional Rental Income: $785 Airbnb ROI: 8.25% Traditional ROI: 4.16%
316 N College Ave Greencastle, IN Completely remodeled and move-in ready! This charming 2-bedroom, 1-bath home on College Av...	2 beds \| 1 baths \| 1,697 sq.ft.	$189,900	Airbnb cash on cash: 3.28% Traditional cash on cash: 2.97% Airbnb Rental Income: $1442 Traditional Rental Income: $958 Airbnb ROI: 3.28% Traditional ROI: 2.97%
201 Leach St Greencastle, IN This home is AMAZING and will not last long!! 3 bdrm, 2 ba corner lot home that has been p...	3 beds \| 2 baths \| 1,032 sq.ft.	$215,000	Airbnb cash on cash: 4.57% Traditional cash on cash: 5.52% Airbnb Rental Income: $1736 Traditional Rental Income: $1452 Airbnb ROI: 4.57% Traditional ROI: 5.52%
5075 Van Bibber Lake Est 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: 5.44% Traditional cash on cash: 5.93% Airbnb Rental Income: $1442 Traditional Rental Income: $1073 Airbnb ROI: 5.44% 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. ...	4 beds \| 2 baths \| 2,015 sq.ft.	$280,000	Airbnb cash on cash: 7.7% Traditional cash on cash: 6.89% Airbnb Rental Income: $3207 Traditional Rental Income: $2271 Airbnb ROI: 7.7% Traditional ROI: 6.89%
1158 W US Hwy 40 Hwy 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: 5.13% Traditional cash on cash: 8.11% Airbnb Rental Income: $1736 Traditional Rental Income: $1823 Airbnb ROI: 5.13% Traditional ROI: 8.11%
1000 S Jackson St Greencastle, IN 1000 S Jackson St, Greencastle, IN 46135 \| Single Family Residential	4 beds \| 2 baths \| 2,958 sq.ft.	$369,900	Airbnb cash on cash: 5.04% Traditional cash on cash: 3.6% Airbnb Rental Income: $3207 Traditional Rental Income: $1982 Airbnb ROI: 5.04% Traditional ROI: 3.6%
32 Edgelea Dr Greencastle, IN Discover a distinguished lifestyle at 32 Edgelea DR, Greencastle, IN. Built in 1975, this ...	4 beds \| 2 baths \| 3,696 sq.ft.	$359,000	Airbnb cash on cash: 5.25% Traditional cash on cash: 3.97% Airbnb Rental Income: $3207 Traditional Rental Income: $2052 Airbnb ROI: 5.25% Traditional ROI: 3.97%
2036 Van Bibber Lake Est Greencastle, IN 2036 Van Bibber Lake Est, Greencastle, IN 46135 \| Manufactured Home	3 beds \| 1 baths \| 960 sq.ft.	$170,000	Airbnb cash on cash: 5.18% Traditional cash on cash: 3.91% Airbnb Rental Income: $1736 Traditional Rental Income: $1052 Airbnb ROI: 5.18% Traditional ROI: 3.91%
7556 W County Road 350 S Greencastle, IN 7556 W County Road 350 S, Greencastle, IN 46135 \| Single Family Residential	3 beds \| 2 baths \| 3,432 sq.ft.	$495,000	Airbnb cash on cash: 0.67% Traditional cash on cash: 0.88% Airbnb Rental Income: $1736 Traditional Rental Income: $1355 Airbnb ROI: 0.67% Traditional ROI: 0.88%
5814 W County Road 100 S Greencastle, IN Newer 3-bedroom, 2-full bath ranch on 15.09 acres with separate residence, and 30x80 pole ...	3 beds \| 2 baths \| 1,976 sq.ft.	$579,900	Airbnb cash on cash: 0.31% Traditional cash on cash: 1.64% Airbnb Rental Income: $1736 Traditional Rental Income: $1980 Airbnb ROI: 0.31% Traditional ROI: 1.64%
250 East Greencastle, IN	N/A beds \| N/A baths \| 2,534 sq.ft.	$1,398,000	Airbnb cash on cash: -1.19% Traditional cash on cash: -1.31% Airbnb Rental Income: $1359 Traditional Rental Income: $787 Airbnb ROI: -1.19% Traditional ROI: -1.31%
0 Longcastle Dr Greencastle, IN	N/A beds \| N/A baths \| N/A	$75,000	Airbnb cash on cash: 9.65% Traditional cash on cash: 2.7% Airbnb Rental Income: $1359 Traditional Rental Income: $429 Airbnb ROI: 9.65% Traditional ROI: 2.7%
0 N Us 231 N Greencastle, IN 0 N Us 231 N, Greencastle, IN 46135 \| Other	N/A beds \| N/A baths \| N/A	$1,773,323	Airbnb cash on cash: -1.33% Traditional cash on cash: -1.64% Airbnb Rental Income: $1359 Traditional Rental Income: $429 Airbnb ROI: -1.33% Traditional ROI: -1.64%
68 Ridgeland Rd Greencastle, IN 68 Ridgeland Rd, Greencastle, IN 46135 \| Other	N/A beds \| N/A baths \| N/A	$199,999	Airbnb cash on cash: 2.64% Traditional cash on cash: -0.03% Airbnb Rental Income: $1359 Traditional Rental Income: $437 Airbnb ROI: 2.64% Traditional ROI: -0.03%
6850 W County Road 25 S Greencastle, IN 6850 W County Road 25 S, Greencastle, IN 46135 \| Other	N/A beds \| N/A baths \| 3,354 sq.ft.	$245,000	Airbnb cash on cash: 1.83% Traditional cash on cash: 2.33% Airbnb Rental Income: $1359 Traditional Rental Income: $1059 Airbnb ROI: 1.83% Traditional ROI: 2.33%
000 S County Road 250 E Greencastle, IN 000 S County Road 250 E, Greencastle, IN 46135 \| Other	N/A beds \| N/A baths \| N/A	$1,140,000	Airbnb cash on cash: -1.04% Traditional cash on cash: -1.47% Airbnb Rental Income: $1359 Traditional Rental Income: $487 Airbnb ROI: -1.04% Traditional ROI: -1.47%
1004 Van Bibber Lake Est Greencastle, IN 1004 Van Bibber Lake Est, Greencastle, IN 46135 \| Manufactured Home	2 beds \| 2 baths \| 924 sq.ft.	$119,900	Airbnb cash on cash: 5.87% Traditional cash on cash: 5.66% Airbnb Rental Income: $1442 Traditional Rental Income: $988 Airbnb ROI: 5.87% Traditional ROI: 5.66%
0 US Highway 231 N Hwy N Greencastle, IN 0 US Highway 231 N Hwy N, Greencastle, IN 46135 \| Other	N/A beds \| N/A baths \| N/A	$500,000	Airbnb cash on cash: -0.02% Traditional cash on cash: -1% Airbnb Rental Income: $1359 Traditional Rental Income: $487 Airbnb ROI: -0.02% Traditional ROI: -1%
4016 Van Bibber Lake Est 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: 1.38% Traditional cash on cash: 5.09% Airbnb Rental Income: $964 Traditional Rental Income: $1215 Airbnb ROI: 1.38% Traditional ROI: 5.09%
700 Albin Pond Rd Greencastle, IN Motivated sellers on this beautiful brown brick ranch home with full finished walkout base...	4 beds \| 2 baths \| 3,192 sq.ft.	$285,900	Airbnb cash on cash: 7.03% Traditional cash on cash: 8.02% Airbnb Rental Income: $3207 Traditional Rental Income: $2751 Airbnb ROI: 7.03% Traditional ROI: 8.02%
2004 Fairway Dr Greencastle, IN 2004 Fairway Dr, Greencastle, IN 46135 \| Single Family Residential	4 beds \| 3 baths \| 3,546 sq.ft.	$369,900	Airbnb cash on cash: 5.04% Traditional cash on cash: 4.25% Airbnb Rental Income: $3207 Traditional Rental Income: $2207 Airbnb ROI: 5.04% Traditional ROI: 4.25%
33 Cottonwood Ct Greencastle, IN 33 Cottonwood Ct, Greencastle, IN 46135 \| Single Family Residential	3 beds \| 2 baths \| 1,094 sq.ft.	$215,000	Airbnb cash on cash: 3.88% Traditional cash on cash: 4% Airbnb Rental Income: $1736 Traditional Rental Income: $1282 Airbnb ROI: 3.88% Traditional ROI: 4%
32 Beveridge St Greencastle, IN 32 Beveridge St, Greencastle, IN 46135 \| Single Family Residential	1 beds \| 1 baths \| 708 sq.ft.	$175,000	Airbnb cash on cash: 1.29% Traditional cash on cash: 1.45% Airbnb Rental Income: $964 Traditional Rental Income: $641 Airbnb ROI: 1.29% Traditional ROI: 1.45%
464 Glenview Dr Greencastle, IN Presenting an inviting condominium residence at 464 Glenview DR, GREENCASTLE, IN, USA. Con...	3 beds \| 3 baths \| 3,408 sq.ft.	$329,900	Airbnb cash on cash: 1.05% Traditional cash on cash: 4.25% Airbnb Rental Income: $1736 Traditional Rental Income: $2249 Airbnb ROI: 1.05% Traditional ROI: 4.25%
735 E Washington St Greencastle, IN 735 E Washington St, Greencastle, IN 46135 \| Single Family Residential	3 beds \| 1 baths \| 2,553 sq.ft.	$145,000	Airbnb cash on cash: 6.54% Traditional cash on cash: 5.97% Airbnb Rental Income: $1736 Traditional Rental Income: $1178 Airbnb ROI: 6.54% Traditional ROI: 5.97%
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: 2.28% Traditional cash on cash: 5.22% Airbnb Rental Income: $1442 Traditional Rental Income: $1816 Airbnb ROI: 2.28% Traditional ROI: 5.22%
2138 W Range Line Rd Greencastle, IN 2138 W Range Line Rd, Greencastle, IN 46135 \| Single Family Residential	4 beds \| 2 baths \| 2,160 sq.ft.	$290,000	Airbnb cash on cash: 6.91% Traditional cash on cash: 4.86% Airbnb Rental Income: $3207 Traditional Rental Income: $1924 Airbnb ROI: 6.91% Traditional ROI: 4.86%
11806 E Pocahontas Dr Greencastle, IN 11806 E Pocahontas Dr, Greencastle, IN 46135 \| Single Family Residential	3 beds \| 2 baths \| 1,792 sq.ft.	$398,900	Airbnb cash on cash: 1.17% Traditional cash on cash: 2.36% Airbnb Rental Income: $1736 Traditional Rental Income: $1701 Airbnb ROI: 1.17% Traditional ROI: 2.36%
625 E Washington St Greencastle, IN 625 E Washington St, Greencastle, IN 46135 \| Single Family Residential	5 beds \| 1 baths \| 2,997 sq.ft.	$199,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.17% Airbnb Rental Income: $null Traditional Rental Income: $1423 Airbnb ROI: N/A Traditional ROI: 5.17%
1742 E Range Line Rd Greencastle, IN Remodeled home located just outside the city limits of Greencastle on a beautiful lot with...	3 beds \| 2 baths \| 1,843 sq.ft.	$235,900	Airbnb cash on cash: 4.01% Traditional cash on cash: 5.57% Airbnb Rental Income: $1736 Traditional Rental Income: $1607 Airbnb ROI: 4.01% Traditional ROI: 5.57%

Real Estate investment in Greencastle, IN

There are 74 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 $91. In July 2026, the average monthly cash on cash return in Greencastle is 5.00%. The average monthly rental income in Greencastle is $1,505.

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

There are 74 investment properties available for sale in Greencastle.

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

The ROI for Short-Term is higher than the Long-Term in Greencastle with average rental income of $1,736.

Your search for investment property begins and ends here

Investment Property for Sale in Greencastle, IN

111 S Spring St #204

Greencastle, IN

2 beds | 2 baths | 1,087 sq.ft.

$174,900

Airbnb cash on cash: 1.65%

Traditional cash on cash: 1.75%

Airbnb Rental Income: $1442

Traditional Rental Income: $1030

Airbnb ROI: 1.65%

Traditional ROI: 1.75%

724 N US 231 Hwy

Greencastle, IN

3 beds | 1 baths | 1,624 sq.ft.

$270,000

Airbnb cash on cash: 3.29%

Traditional cash on cash: 3.73%

Airbnb Rental Income: $1736

Traditional Rental Income: $1369

Airbnb ROI: 3.29%

Traditional ROI: 3.73%

1041 Shadowlawn Ave

Greencastle, IN

3 beds | 3 baths | 3,794 sq.ft.

$379,900

Airbnb cash on cash: 1.78%

Traditional cash on cash: 3.36%

Airbnb Rental Income: $1736

Traditional Rental Income: $1820

Airbnb ROI: 1.78%

Traditional ROI: 3.36%

8 Paradise Ln

Greencastle, IN

3 beds | 1 baths | 1,571 sq.ft.

$249,000

Airbnb cash on cash: 3.53%

Traditional cash on cash: 4.06%

Airbnb Rental Income: $1736

Traditional Rental Income: $1382

Airbnb ROI: 3.53%

Traditional ROI: 4.06%

1747 E Tall Oaks Ln

Greencastle, IN

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

$482,500

Airbnb cash on cash: 3.95%

Traditional cash on cash: 10.35%

Airbnb Rental Income: $3207

Traditional Rental Income: $5372

Airbnb ROI: 3.95%

Traditional ROI: 10.35%

3777 N Us Highway 231

Greencastle, IN

4 beds | 2 baths | 4,431 sq.ft.

$415,000

Airbnb cash on cash: 4.96%

Traditional cash on cash: 3.16%

Airbnb Rental Income: $3207

Traditional Rental Income: $1784

Airbnb ROI: 4.96%

Traditional ROI: 3.16%

136 W Berry St

Greencastle, IN

3 beds | 1 baths | 1,152 sq.ft.

$200,000

Airbnb cash on cash: 5.09%

Traditional cash on cash: 7.18%

Airbnb Rental Income: $1736

Traditional Rental Income: $1653

Airbnb ROI: 5.09%

Traditional ROI: 7.18%

7 S Bloomington St

Greencastle, IN

4 beds | 2 baths | 5,786 sq.ft.

$249,900

Airbnb cash on cash: 8.64%

Traditional cash on cash: 5.57%

Airbnb Rental Income: $3207

Traditional Rental Income: $1757

Airbnb ROI: 8.64%