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: N/A Traditional cash on cash: 1.75% Airbnb Rental Income: $null Traditional Rental Income: $1030 Airbnb ROI: N/A 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.	$260,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.91% Airbnb Rental Income: $null Traditional Rental Income: $1369 Airbnb ROI: N/A Traditional ROI: 3.91%
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.	$359,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.6% Airbnb Rental Income: $null Traditional Rental Income: $1820 Airbnb ROI: N/A Traditional ROI: 3.6%
710 E Franklin St Greencastle, IN Well maintained three bedroom two bath home on a nice sized lot. Living room has a gas fi...	3 beds \| 2 baths \| 1,168 sq.ft.	$220,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.78% Airbnb Rental Income: $null Traditional Rental Income: $1542 Airbnb ROI: N/A Traditional ROI: 5.78%
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: N/A Traditional cash on cash: 10.35% Airbnb Rental Income: $null Traditional Rental Income: $5372 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 3.16% Airbnb Rental Income: $null Traditional Rental Income: $1784 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 7.18% Airbnb Rental Income: $null Traditional Rental Income: $1653 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 5.57% Airbnb Rental Income: $null Traditional Rental Income: $1757 Airbnb ROI: N/A 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.	$199,900	Airbnb cash on cash: N/A Traditional cash on cash: 8.05% Airbnb Rental Income: $null Traditional Rental Income: $1849 Airbnb ROI: N/A Traditional ROI: 8.05%
5629 E County Road 700 S Greencastle, IN Take a look at this 4.47 acre, 3BR, 2BA, 1782 sq. ft. manufactured home just north of I70 ...	3 beds \| 2 baths \| 1,782 sq.ft.	$325,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.13% Airbnb Rental Income: $null Traditional Rental Income: $1703 Airbnb ROI: N/A Traditional ROI: 4.13%
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: N/A Traditional cash on cash: 4.16% Airbnb Rental Income: $null Traditional Rental Income: $785 Airbnb ROI: N/A Traditional ROI: 4.16%
518 Brentfield Dr Greencastle, IN This incredible 5-bedroom, 3-bathroom home with a finished basement is now available, with...	5 beds \| 3 baths \| 4,284 sq.ft.	$480,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.78% Airbnb Rental Income: $null Traditional Rental Income: $2924 Airbnb ROI: N/A Traditional ROI: 4.78%
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.	$210,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.67% Airbnb Rental Income: $null Traditional Rental Income: $1452 Airbnb ROI: N/A Traditional ROI: 5.67%
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: N/A Traditional cash on cash: 5.93% Airbnb Rental Income: $null Traditional Rental Income: $1073 Airbnb ROI: N/A Traditional ROI: 5.93%
211 S Bloomington St Greencastle, IN Historic Home less than one block from DePauw University main entrance! This home includes...	4 beds \| 2 baths \| 3,640 sq.ft.	$219,000	Airbnb cash on cash: N/A Traditional cash on cash: 10.02% Airbnb Rental Income: $null Traditional Rental Income: $2482 Airbnb ROI: N/A Traditional ROI: 10.02%
1644 W County Road 100 N Greencastle, IN Charming Country Home on 3 Acres - Peaceful Setting, Prime Location! Welcome to this im...	3 beds \| 1 baths \| 1,600 sq.ft.	$342,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.53% Airbnb Rental Income: $null Traditional Rental Income: $1923 Airbnb ROI: N/A Traditional ROI: 4.53%
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: N/A Traditional cash on cash: 6.89% Airbnb Rental Income: $null Traditional Rental Income: $2271 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 8.11% Airbnb Rental Income: $null Traditional Rental Income: $1823 Airbnb ROI: N/A 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.	$355,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.82% Airbnb Rental Income: $null Traditional Rental Income: $1982 Airbnb ROI: N/A Traditional ROI: 3.82%
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.	$319,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.69% Airbnb Rental Income: $null Traditional Rental Income: $2052 Airbnb ROI: N/A Traditional ROI: 4.69%
302 N College Ave Greencastle, IN 302 N College Ave, Greencastle, IN 46135 \| Multi Family	4 beds \| N/A baths \| 1,545 sq.ft.	$139,900	Airbnb cash on cash: N/A Traditional cash on cash: 7.73% Airbnb Rental Income: $null Traditional Rental Income: $1377 Airbnb ROI: N/A Traditional ROI: 7.73%
2036 Van Bibber Lake Est Greencastle, IN 2036 Van Bibber Lake Est, Greencastle, IN 46135 \| Manufactured Home	3 beds \| 1 baths \| 960 sq.ft.	$165,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.07% Airbnb Rental Income: $null Traditional Rental Income: $1052 Airbnb ROI: N/A Traditional ROI: 4.07%
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.	$460,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.09% Airbnb Rental Income: $null Traditional Rental Income: $1355 Airbnb ROI: N/A Traditional ROI: 1.09%
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: N/A Traditional cash on cash: 1.64% Airbnb Rental Income: $null Traditional Rental Income: $1980 Airbnb ROI: N/A 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: N/A Traditional cash on cash: -1.31% Airbnb Rental Income: $null Traditional Rental Income: $787 Airbnb ROI: N/A Traditional ROI: -1.31%
0 Longcastle Dr Greencastle, IN	N/A beds \| N/A baths \| N/A	$75,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.7% Airbnb Rental Income: $null Traditional Rental Income: $429 Airbnb ROI: N/A 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: N/A Traditional cash on cash: -1.64% Airbnb Rental Income: $null Traditional Rental Income: $429 Airbnb ROI: N/A 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: N/A Traditional cash on cash: -0.03% Airbnb Rental Income: $null Traditional Rental Income: $437 Airbnb ROI: N/A Traditional ROI: -0.03%
00 Valley Drive Dr Greencastle, IN 00 Valley Drive Dr, Greencastle, IN 46135 \| Other	N/A beds \| N/A baths \| N/A	$39,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.48% Airbnb Rental Income: $null Traditional Rental Income: $429 Airbnb ROI: N/A Traditional ROI: 5.48%
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: N/A Traditional cash on cash: 2.33% Airbnb Rental Income: $null Traditional Rental Income: $1059 Airbnb ROI: N/A 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: N/A Traditional cash on cash: -1.47% Airbnb Rental Income: $null Traditional Rental Income: $487 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 5.66% Airbnb Rental Income: $null Traditional Rental Income: $988 Airbnb ROI: N/A 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: N/A Traditional cash on cash: -1% Airbnb Rental Income: $null Traditional Rental Income: $487 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 5.09% Airbnb Rental Income: $null Traditional Rental Income: $1215 Airbnb ROI: N/A Traditional ROI: 5.09%
2004 Fairway Dr Greencastle, IN 2004 Fairway Dr, Greencastle, IN 46135 \| Single Family Residential	4 beds \| 3 baths \| 3,546 sq.ft.	$361,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.38% Airbnb Rental Income: $null Traditional Rental Income: $2207 Airbnb ROI: N/A Traditional ROI: 4.38%
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: N/A Traditional cash on cash: 4% Airbnb Rental Income: $null Traditional Rental Income: $1282 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 1.45% Airbnb Rental Income: $null Traditional Rental Income: $641 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 4.25% Airbnb Rental Income: $null Traditional Rental Income: $2249 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 5.97% Airbnb Rental Income: $null Traditional Rental Income: $1178 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 5.22% Airbnb Rental Income: $null Traditional Rental Income: $1816 Airbnb ROI: N/A Traditional ROI: 5.22%

Real Estate investment in Greencastle, IN

There are 131 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 October 2026, the average monthly cash on cash return in Greencastle is 4.00%. The average monthly rental income in Greencastle is $1,438.

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

There are 131 investment properties available for sale in Greencastle.

The ROI for Short-Term is higher than the Long-Term in Greencastle with average rental income of $N/A.

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: N/A

Traditional cash on cash: 1.75%

Airbnb Rental Income: $null

Traditional Rental Income: $1030

Airbnb ROI: N/A

Traditional ROI: 1.75%

724 N US 231 Hwy

Greencastle, IN

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

$260,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.91%

Airbnb Rental Income: $null

Traditional Rental Income: $1369

Airbnb ROI: N/A

Traditional ROI: 3.91%

1041 Shadowlawn Ave

Greencastle, IN

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

$359,900

Airbnb cash on cash: N/A

Traditional cash on cash: 3.6%

Airbnb Rental Income: $null

Traditional Rental Income: $1820

Airbnb ROI: N/A

Traditional ROI: 3.6%

710 E Franklin St

Greencastle, IN

3 beds | 2 baths | 1,168 sq.ft.

$220,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.78%

Airbnb Rental Income: $null

Traditional Rental Income: $1542

Airbnb ROI: N/A

Traditional ROI: 5.78%

1747 E Tall Oaks Ln

Greencastle, IN

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

$482,500

Airbnb cash on cash: N/A

Traditional cash on cash: 10.35%

Airbnb Rental Income: $null

Traditional Rental Income: $5372

Airbnb ROI: N/A

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: N/A

Traditional cash on cash: 3.16%

Airbnb Rental Income: $null

Traditional Rental Income: $1784

Airbnb ROI: N/A

Traditional ROI: 3.16%

136 W Berry St

Greencastle, IN

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

$200,000

Airbnb cash on cash: N/A

Traditional cash on cash: 7.18%

Airbnb Rental Income: $null

Traditional Rental Income: $1653

Airbnb ROI: N/A

Traditional ROI: 7.18%

7 S Bloomington St

Greencastle, IN

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

$249,900

Airbnb cash on cash: N/A

Traditional cash on cash: 5.57%

Airbnb Rental Income: $null

Traditional Rental Income: $1757

Airbnb ROI: N/A