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.

Single Family Homes for Sale in Greencastle, IN

Search for Single Family Residential for Sale in Greencastle, Indiana. Browse all of Mashvisor’s Single Family Residential listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 71 Single Family Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
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: 3.04% Traditional cash on cash: 3.91% Airbnb Rental Income: $1615 Traditional Rental Income: $1369 Airbnb ROI: 3.04% 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.	$369,900	Airbnb cash on cash: 1.56% Traditional cash on cash: 3.47% Airbnb Rental Income: $1615 Traditional Rental Income: $1820 Airbnb ROI: 1.56% Traditional ROI: 3.47%
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: 3.1% Traditional cash on cash: 4.06% Airbnb Rental Income: $1615 Traditional Rental Income: $1382 Airbnb ROI: 3.1% Traditional ROI: 4.06%
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: 3.93% Traditional cash on cash: 5.78% Airbnb Rental Income: $1615 Traditional Rental Income: $1542 Airbnb ROI: 3.93% 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: 3.85% Traditional cash on cash: 10.35% Airbnb Rental Income: $3151 Traditional Rental Income: $5372 Airbnb ROI: 3.85% 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: 4.84% Traditional cash on cash: 3.16% Airbnb Rental Income: $3151 Traditional Rental Income: $1784 Airbnb ROI: 4.84% 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: 4.56% Traditional cash on cash: 7.18% Airbnb Rental Income: $1615 Traditional Rental Income: $1653 Airbnb ROI: 4.56% 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: 8.45% Traditional cash on cash: 5.57% Airbnb Rental Income: $3151 Traditional Rental Income: $1757 Airbnb ROI: 8.45% 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: 4.4% Traditional cash on cash: 8.05% Airbnb Rental Income: $1615 Traditional Rental Income: $1849 Airbnb ROI: 4.4% Traditional ROI: 8.05%
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: 4.19% Traditional cash on cash: 5.67% Airbnb Rental Income: $1615 Traditional Rental Income: $1452 Airbnb ROI: 4.19% Traditional ROI: 5.67%
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: 7.52% Traditional cash on cash: 6.89% Airbnb Rental Income: $3151 Traditional Rental Income: $2271 Airbnb ROI: 7.52% Traditional ROI: 6.89%
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: 5.19% Traditional cash on cash: 3.82% Airbnb Rental Income: $3151 Traditional Rental Income: $1982 Airbnb ROI: 5.19% 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.	$329,000	Airbnb cash on cash: 5.74% Traditional cash on cash: 4.49% Airbnb Rental Income: $3151 Traditional Rental Income: $2052 Airbnb ROI: 5.74% Traditional ROI: 4.49%
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.	$470,000	Airbnb cash on cash: 0.57% Traditional cash on cash: 1.03% Airbnb Rental Income: $1615 Traditional Rental Income: $1355 Airbnb ROI: 0.57% Traditional ROI: 1.03%
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: 0.12% Traditional cash on cash: 1.64% Airbnb Rental Income: $1615 Traditional Rental Income: $1980 Airbnb ROI: 0.12% Traditional ROI: 1.64%
2004 Fairway Dr Greencastle, IN 2004 Fairway Dr, Greencastle, IN 46135 \| Single Family Residential	4 beds \| 3 baths \| 3,546 sq.ft.	$365,900	Airbnb cash on cash: 4.98% Traditional cash on cash: 4.31% Airbnb Rental Income: $3151 Traditional Rental Income: $2207 Airbnb ROI: 4.98% Traditional ROI: 4.31%
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: 3.38% Traditional cash on cash: 4% Airbnb Rental Income: $1615 Traditional Rental Income: $1282 Airbnb ROI: 3.38% 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: 2.37% Traditional cash on cash: 1.45% Airbnb Rental Income: $1180 Traditional Rental Income: $641 Airbnb ROI: 2.37% Traditional ROI: 1.45%
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: 5.82% Traditional cash on cash: 5.97% Airbnb Rental Income: $1615 Traditional Rental Income: $1178 Airbnb ROI: 5.82% 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: $1441 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.	$280,000	Airbnb cash on cash: 7.04% Traditional cash on cash: 5.1% Airbnb Rental Income: $3151 Traditional Rental Income: $1924 Airbnb ROI: 7.04% Traditional ROI: 5.1%
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: 0.9% Traditional cash on cash: 2.36% Airbnb Rental Income: $1615 Traditional Rental Income: $1701 Airbnb ROI: 0.9% 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%
718 Highwood Ave Greencastle, IN Step into this beautifully updated 4-bedroom, 2.5-bath residence that perfectly blends com...	4 beds \| 2 baths \| 2,128 sq.ft.	$367,500	Airbnb cash on cash: 5.33% Traditional cash on cash: 5.51% Airbnb Rental Income: $3151 Traditional Rental Income: $2500 Airbnb ROI: 5.33% Traditional ROI: 5.51%
3864 N Us Highway 231 Greencastle, IN 3864 N Us Highway 231, Greencastle, IN 46135 \| Single Family Residential	4 beds \| 2 baths \| 4,438 sq.ft.	$699,000	Airbnb cash on cash: 1.75% Traditional cash on cash: 0.62% Airbnb Rental Income: $3151 Traditional Rental Income: $1702 Airbnb ROI: 1.75% Traditional ROI: 0.62%
1193 W County Road 125 S Greencastle, IN 1193 W County Road 125 S, Greencastle, IN 46135 \| Single Family Residential	5 beds \| 2 baths \| 3,903 sq.ft.	$189,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.33% Airbnb Rental Income: $null Traditional Rental Income: $1921 Airbnb ROI: N/A Traditional ROI: 8.33%
28 Beveridge Greencastle, IN 28 Beveridge, Greencastle, IN 46135 \| Single Family Residential	2 beds \| 1 baths \| 1,550 sq.ft.	$159,900	Airbnb cash on cash: 4.18% Traditional cash on cash: 3.81% Airbnb Rental Income: $1441 Traditional Rental Income: $956 Airbnb ROI: 4.18% Traditional ROI: 3.81%
72 Briarwood Ct Greencastle, IN 72 Briarwood Ct, Greencastle, IN 46135 \| Single Family Residential	4 beds \| 3 baths \| 2,329 sq.ft.	$405,000	Airbnb cash on cash: 4.33% Traditional cash on cash: 4.06% Airbnb Rental Income: $3151 Traditional Rental Income: $2333 Airbnb ROI: 4.33% Traditional ROI: 4.06%
3247 W County Road 100 S Greencastle, IN Experience the perfect blend of country charm and modern luxury in this beautifully remode...	4 beds \| 3 baths \| 2,828 sq.ft.	$429,900	Airbnb cash on cash: 4.45% Traditional cash on cash: 5.33% Airbnb Rental Income: $3151 Traditional Rental Income: $2790 Airbnb ROI: 4.45% Traditional ROI: 5.33%
307 Greenwood Ave Greencastle, IN 307 Greenwood Ave, Greencastle, IN 46135 \| Single Family Residential	4 beds \| 2 baths \| 2,808 sq.ft.	$305,000	Airbnb cash on cash: 6.32% Traditional cash on cash: 5.02% Airbnb Rental Income: $3151 Traditional Rental Income: $2062 Airbnb ROI: 6.32% Traditional ROI: 5.02%
3410 S County Road 800 W Greencastle, IN 3410 S County Road 800 W, Greencastle, IN 46135 \| Single Family Residential	2 beds \| 2 baths \| 1,308 sq.ft.	$179,900	Airbnb cash on cash: 3.1% Traditional cash on cash: 3.94% Airbnb Rental Income: $1441 Traditional Rental Income: $1155 Airbnb ROI: 3.1% Traditional ROI: 3.94%
1805 S County Road 400 W Greencastle, IN 1805 S County Road 400 W, Greencastle, IN 46135 \| Single Family Residential	5 beds \| 3 baths \| 3,840 sq.ft.	$375,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.8% Airbnb Rental Income: $null Traditional Rental Income: $2432 Airbnb ROI: N/A Traditional ROI: 4.8%
315 Greenwood Ave Greencastle, IN 315 Greenwood Ave, Greencastle, IN 46135 \| Single Family Residential	5 beds \| 3 baths \| 3,094 sq.ft.	$339,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.5% Airbnb Rental Income: $null Traditional Rental Income: $2433 Airbnb ROI: N/A Traditional ROI: 5.5%
2468 W County Road 25 N Greencastle, IN 2468 W County Road 25 N, Greencastle, IN 46135 \| Single Family Residential	3 beds \| 2 baths \| 1,200 sq.ft.	$239,900	Airbnb cash on cash: 2.85% Traditional cash on cash: 3.39% Airbnb Rental Income: $1615 Traditional Rental Income: $1280 Airbnb ROI: 2.85% Traditional ROI: 3.39%
2061 Fairway Dr Greencastle, IN Don't miss this spacious 3-bedroom, 2-bath ranch offering nearly 1,800 square feet of comf...	3 beds \| 2 baths \| 1,771 sq.ft.	$295,000	Airbnb cash on cash: 2.53% Traditional cash on cash: 5.45% Airbnb Rental Income: $1615 Traditional Rental Income: $1968 Airbnb ROI: 2.53% Traditional ROI: 5.45%
811 Shadowlawn Ave Greencastle, IN 811 Shadowlawn Ave, Greencastle, IN 46135 \| Single Family Residential	4 beds \| 2 baths \| 2,525 sq.ft.	$249,900	Airbnb cash on cash: 8.09% Traditional cash on cash: 6.21% Airbnb Rental Income: $3151 Traditional Rental Income: $1994 Airbnb ROI: 8.09% Traditional ROI: 6.21%
316 N Madison St Greencastle, IN 316 N Madison St, Greencastle, IN 46135 \| Single Family Residential	2 beds \| 1 baths \| 858 sq.ft.	$135,000	Airbnb cash on cash: 5.24% Traditional cash on cash: 3.34% Airbnb Rental Income: $1441 Traditional Rental Income: $765 Airbnb ROI: 5.24% Traditional ROI: 3.34%
5232 E Us Highway 40 Greencastle, IN 5232 E Us Highway 40, Greencastle, IN 46135 \| Single Family Residential	2 beds \| 1 baths \| 1,596 sq.ft.	$95,000	Airbnb cash on cash: 8.09% Traditional cash on cash: 8.25% Airbnb Rental Income: $1441 Traditional Rental Income: $1027 Airbnb ROI: 8.09% Traditional ROI: 8.25%
3507 S County Road 200 W Greencastle, IN 3507 S County Road 200 W, Greencastle, IN 46135 \| Single Family Residential	4 beds \| 1 baths \| 1,876 sq.ft.	$234,900	Airbnb cash on cash: 8.71% Traditional cash on cash: 2.82% Airbnb Rental Income: $3151 Traditional Rental Income: $1129 Airbnb ROI: 8.71% Traditional ROI: 2.82%

Your search for investment property begins and ends here

Single Family Homes for Sale in Greencastle, IN

724 N US 231 Hwy

Greencastle, IN

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

$260,000

Airbnb cash on cash: 3.04%

Traditional cash on cash: 3.91%

Airbnb Rental Income: $1615

Traditional Rental Income: $1369

Airbnb ROI: 3.04%

Traditional ROI: 3.91%

1041 Shadowlawn Ave

Greencastle, IN

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

$369,900

Airbnb cash on cash: 1.56%

Traditional cash on cash: 3.47%

Airbnb Rental Income: $1615

Traditional Rental Income: $1820

Airbnb ROI: 1.56%

Traditional ROI: 3.47%

8 Paradise Ln

Greencastle, IN

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

$249,000

Airbnb cash on cash: 3.1%

Traditional cash on cash: 4.06%

Airbnb Rental Income: $1615

Traditional Rental Income: $1382

Airbnb ROI: 3.1%

Traditional ROI: 4.06%

710 E Franklin St

Greencastle, IN

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

$220,000

Airbnb cash on cash: 3.93%

Traditional cash on cash: 5.78%

Airbnb Rental Income: $1615

Traditional Rental Income: $1542

Airbnb ROI: 3.93%

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: 3.85%

Traditional cash on cash: 10.35%

Airbnb Rental Income: $3151

Traditional Rental Income: $5372

Airbnb ROI: 3.85%

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: 4.84%

Traditional cash on cash: 3.16%

Airbnb Rental Income: $3151

Traditional Rental Income: $1784

Airbnb ROI: 4.84%

Traditional ROI: 3.16%

136 W Berry St

Greencastle, IN

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

$200,000

Airbnb cash on cash: 4.56%

Traditional cash on cash: 7.18%

Airbnb Rental Income: $1615

Traditional Rental Income: $1653

Airbnb ROI: 4.56%

Traditional ROI: 7.18%

7 S Bloomington St

Greencastle, IN

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

$249,900

Airbnb cash on cash: 8.45%

Traditional cash on cash: 5.57%

Airbnb Rental Income: $3151

Traditional Rental Income: $1757

Airbnb ROI: 8.45%