Real Estate Investment Properties for Sale in Greencastle, PA

Looking for investment property in Greencastle, PA with high ROI ?

Explore a variety of short-term homes & houses in Greencastle, PA. Invest wisely with VRBO & Greencastle, PA 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, PA

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
250 East Madison St Greencastle, PA Beautiful Stately home in Greencastle. Located on a convenient side street. WARM AND INVIT...	3 beds \| 1 baths \| 2,440 sq.ft.	$305,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.79% Airbnb Rental Income: $null Traditional Rental Income: $1581 Airbnb ROI: N/A Traditional ROI: 2.79%
2384 Castlegreen Dr Greencastle, PA Large Brick Colonial on 2.54 acres in Greencastle Greens.4 bedrooms, 2.5 baths, den and fa...	4 beds \| 3 baths \| 4,666 sq.ft.	$625,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.67% Airbnb Rental Income: $null Traditional Rental Income: $2296 Airbnb ROI: N/A Traditional ROI: 1.67%
543 RAEANN DR Greencastle, PA Welcome to 543 Raeann Drive! This fabulous, nearly new home(never occupied) nestled in th...	4 beds \| 3 baths \| N/A	$335,000	Airbnb cash on cash: N/A Traditional cash on cash: 5% Airbnb Rental Income: $null Traditional Rental Income: $2301 Airbnb ROI: N/A Traditional ROI: 5%
1401 Shannon Dr S Greencastle, PA To-be-built Glenix Homes in the Greens of Greencastle feature authentic Modern Farmhouse o...	3 beds \| 2 baths \| 2,000 sq.ft.	$470,871	Airbnb cash on cash: N/A Traditional cash on cash: 4.17% Airbnb Rental Income: $null Traditional Rental Income: $2513 Airbnb ROI: N/A Traditional ROI: 4.17%
171 East Ave Greencastle, PA One-of-a-kind historic property offering endless potential. Previously used as a schoolhou...	1 beds \| N/A baths \| 1,920 sq.ft.	$275,000	Airbnb cash on cash: -0.63% Traditional cash on cash: 4.57% Airbnb Rental Income: $623 Traditional Rental Income: $1697 Airbnb ROI: -0.63% Traditional ROI: 4.57%
1864 Shannon Dr S Greencastle, PA Welcome to this newly built 2025 ranch villa located in the sought-after Greencastle Green...	3 beds \| 3 baths \| 2,255 sq.ft.	$425,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.14% Airbnb Rental Income: $null Traditional Rental Income: $2628 Airbnb ROI: N/A Traditional ROI: 4.14%
14732 Cedarbrook Dr Greencastle, PA Buyer may qualify for $0 down payment! Welcome to this spacious and move-in-ready 4-bedroo...	4 beds \| 2 baths \| N/A	$399,999	Airbnb cash on cash: N/A Traditional cash on cash: 5.35% Airbnb Rental Income: $null Traditional Rental Income: $2941 Airbnb ROI: N/A Traditional ROI: 5.35%
341 W BALTIMORE STREET Greencastle, PA Affordable Starter or retirement home. The home features 2 bedrooms and one bath. Natural ...	2 beds \| 1 baths \| N/A	$275,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.47% Airbnb Rental Income: $null Traditional Rental Income: $1647 Airbnb ROI: N/A Traditional ROI: 4.47%
141 S Washington St Greencastle, PA Four-Story Brick Home with Historic Character & Value-Add Potential This four-story brick ...	3 beds \| 2 baths \| 1,750 sq.ft.	$198,900	Airbnb cash on cash: N/A Traditional cash on cash: 8.43% Airbnb Rental Income: $null Traditional Rental Income: $2092 Airbnb ROI: N/A Traditional ROI: 8.43%
20 Helens Dr Greencastle, PA Welcome to Melrose Meadows III, where quality craftsmanship meets thoughtful design. Curre...	4 beds \| 2 baths \| 2,744 sq.ft.	$599,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.66% Airbnb Rental Income: $null Traditional Rental Income: $3317 Airbnb ROI: N/A Traditional ROI: 3.66%
102560 SHANNON DRIVE S Greencastle, PA The to-be-built Versailles single-family home, at Heritage Overlook, combines classic styl...	5 beds \| 3 baths \| 4,164 sq.ft.	$564,990	Airbnb cash on cash: N/A Traditional cash on cash: 4.39% Airbnb Rental Income: $null Traditional Rental Income: $3549 Airbnb ROI: N/A Traditional ROI: 4.39%
14799 Cedarbrook Dr Greencastle, PA Welcome to 14799 Cedarbrook Dr in Greencastle. Located in a clean, peaceful, and family-fr...	4 beds \| 2 baths \| 1,970 sq.ft.	$340,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.19% Airbnb Rental Income: $null Traditional Rental Income: $2851 Airbnb ROI: N/A Traditional ROI: 6.19%
431 Leitersburg St Greencastle, PA Welcome to the Mitchell-Shook House, a distinguished piece of Greencastle history dating b...	5 beds \| 3 baths \| 4,500 sq.ft.	$750,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.43% Airbnb Rental Income: $null Traditional Rental Income: $3771 Airbnb ROI: N/A Traditional ROI: 3.43%
375 Carolle St Greencastle, PA Located in a Town & Country neighborhood of Greencastle at the edge of town, this 3-bedroo...	3 beds \| 3 baths \| 3,184 sq.ft.	$399,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.24% Airbnb Rental Income: $null Traditional Rental Income: $2834 Airbnb ROI: N/A Traditional ROI: 5.24%
11498 Nicole Dr Greencastle, PA Welcome home!! This easy, one-level living is a beautifully maintained side-by-side home i...	2 beds \| 1 baths \| 1,350 sq.ft.	$265,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.92% Airbnb Rental Income: $null Traditional Rental Income: $1889 Airbnb ROI: N/A Traditional ROI: 4.92%
110 Hykes Road East Greencastle, PA Brand new construction by local custom builder Oliver Homes! This beautiful, 3 bedroom/2 f...	3 beds \| 2 baths \| 1,600 sq.ft.	$349,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.19% Airbnb Rental Income: $null Traditional Rental Income: $2247 Airbnb ROI: N/A Traditional ROI: 5.19%
1256 Emilys Ct Greencastle, PA Convenient location in Rolling Hills! 3bedroom, 2.5 bath end townhome. Upgraded kitchen, 2...	3 beds \| 2 baths \| 1,864 sq.ft.	$275,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.82% Airbnb Rental Income: $null Traditional Rental Income: $2450 Airbnb ROI: N/A Traditional ROI: 6.82%
9931 Mcclanahan Rd Greencastle, PA WOWZZZERSSS!!!! In-Ground POOL, Massive WORKSHOP, & In-Law Suite!!!! That is just the Icin...	4 beds \| 3 baths \| 3,095 sq.ft.	$421,700	Airbnb cash on cash: N/A Traditional cash on cash: 7.28% Airbnb Rental Income: $null Traditional Rental Income: $3842 Airbnb ROI: N/A Traditional ROI: 7.28%
Lot 55 Rossi Dr Greencastle, PA This beautiful Worthington model offers approximately 3,000 sq. ft. of quality new constru...	5 beds \| 3 baths \| 3,000 sq.ft.	$659,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.44% Airbnb Rental Income: $null Traditional Rental Income: $3498 Airbnb ROI: N/A Traditional ROI: 3.44%
408 Carolle St Greencastle, PA Room to Grow-Space to Gather-Flexibility for the Future Welcome to 408 Carolle Street in G...	3 beds \| 3 baths \| 3,384 sq.ft.	$384,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.77% Airbnb Rental Income: $null Traditional Rental Income: $2551 Airbnb ROI: N/A Traditional ROI: 4.77%
3891 Coseytown Rd Greencastle, PA Listed drastically below appraised value of $290k for a quick sell... this low-maintenance...	4 beds \| 2 baths \| 1,792 sq.ft.	$259,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.96% Airbnb Rental Income: $null Traditional Rental Income: $2365 Airbnb ROI: N/A Traditional ROI: 6.96%
365 Blue Bird Trl Greencastle, PA 365 Blue Bird Trl, Greencastle, PA 17225 \| Single Family Residential	4 beds \| 3 baths \| 3,902 sq.ft.	$479,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.1% Airbnb Rental Income: $null Traditional Rental Income: $2190 Airbnb ROI: N/A Traditional ROI: 2.1%
1015 Buchanan Trail East Greencastle, PA 1015 Buchanan Trail East, Greencastle, PA 17225 \| Single Family Residential	3 beds \| 3 baths \| 4,176 sq.ft.	$699,900	Airbnb cash on cash: N/A Traditional cash on cash: -0.05% Airbnb Rental Income: $null Traditional Rental Income: $1851 Airbnb ROI: N/A Traditional ROI: -0.05%
67 James Way Greencastle, PA 67 James Way, Greencastle, PA 17225 \| Single Family Residential	4 beds \| 2 baths \| 2,628 sq.ft.	$499,900	Airbnb cash on cash: N/A Traditional cash on cash: 1.54% Airbnb Rental Income: $null Traditional Rental Income: $2070 Airbnb ROI: N/A Traditional ROI: 1.54%
243 Hykes Rd E Greencastle, PA 243 Hykes Rd E, Greencastle, PA 17225 \| Single Family Residential	3 beds \| 2 baths \| 1,530 sq.ft.	$349,900	Airbnb cash on cash: N/A Traditional cash on cash: 1.95% Airbnb Rental Income: $null Traditional Rental Income: $1577 Airbnb ROI: N/A Traditional ROI: 1.95%
12689 Williamsport Pike Greencastle, PA 12689 Williamsport Pike, Greencastle, PA 17225 \| Single Family Residential	3 beds \| 2 baths \| 1,506 sq.ft.	$359,900	Airbnb cash on cash: N/A Traditional cash on cash: 1.71% Airbnb Rental Income: $null Traditional Rental Income: $1616 Airbnb ROI: N/A Traditional ROI: 1.71%
26 E E Madison St Greencastle, PA 26 E E Madison St, Greencastle, PA 17225 \| Multi Family	3 beds \| N/A baths \| 2,100 sq.ft.	$275,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.91% Airbnb Rental Income: $null Traditional Rental Income: $1251 Airbnb ROI: N/A Traditional ROI: 1.91%
1299 Divinity Dr Greencastle, PA 1299 Divinity Dr, Greencastle, PA 17225 \| Single Family Residential	5 beds \| 3 baths \| 4,484 sq.ft.	$529,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.07% Airbnb Rental Income: $null Traditional Rental Income: $2500 Airbnb ROI: N/A Traditional ROI: 2.07%
823 Buchanan Trl E Greencastle, PA 823 Buchanan Trl E, Greencastle, PA 17225 \| Single Family Residential	5 beds \| 1 baths \| 2,980 sq.ft.	$224,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.12% Airbnb Rental Income: $null Traditional Rental Income: $1301 Airbnb ROI: N/A Traditional ROI: 3.12%
1223 E Pebblebrook Dr Greencastle, PA 1223 E Pebblebrook Dr, Greencastle, PA 17225 \| Single Family Residential	4 beds \| 4 baths \| 4,766 sq.ft.	$535,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.48% Airbnb Rental Income: $null Traditional Rental Income: $2669 Airbnb ROI: N/A Traditional ROI: 2.48%
382 Teaberry Dr Greencastle, PA 382 Teaberry Dr, Greencastle, PA 17225 \| Single Family Residential	3 beds \| 2 baths \| 1,820 sq.ft.	$479,900	Airbnb cash on cash: N/A Traditional cash on cash: 1.28% Airbnb Rental Income: $null Traditional Rental Income: $1822 Airbnb ROI: N/A Traditional ROI: 1.28%
14929 Cedarbrook Dr. Cedarbrook Dr Greencastle, PA 14929 Cedarbrook Dr. Cedarbrook Dr, Greencastle, PA 17225 \| Other	N/A beds \| N/A baths \| N/A	$97,900	Airbnb cash on cash: -0.19% Traditional cash on cash: 0.38% Airbnb Rental Income: $617 Traditional Rental Income: $380 Airbnb ROI: -0.19% Traditional ROI: 0.38%
0 Molly Pitcher Hwy Greencastle, PA 0 Molly Pitcher Hwy, Greencastle, PA 17225 \| Other	N/A beds \| N/A baths \| N/A	$79,900	Airbnb cash on cash: 0.43% Traditional cash on cash: 1.18% Airbnb Rental Income: $617 Traditional Rental Income: $384 Airbnb ROI: 0.43% Traditional ROI: 1.18%
Celestial Ter Greencastle, PA Celestial Ter, Greencastle, PA 17225 \| Other	N/A beds \| N/A baths \| N/A	$120,000	Airbnb cash on cash: -0.54% Traditional cash on cash: -0.03% Airbnb Rental Income: $617 Traditional Rental Income: $384 Airbnb ROI: -0.54% Traditional ROI: -0.03%
14501 Molly Pitcher Hwy Greencastle, PA 14501 Molly Pitcher Hwy, Greencastle, PA 17225 \| Other	N/A beds \| N/A baths \| N/A	$1,350,000	Airbnb cash on cash: -2.39% Traditional cash on cash: -2.34% Airbnb Rental Income: $617 Traditional Rental Income: $380 Airbnb ROI: -2.39% Traditional ROI: -2.34%
0 Hykes Rd Greencastle, PA 0 Hykes Rd, Greencastle, PA 17225 \| Other	N/A beds \| N/A baths \| N/A	$349,900	Airbnb cash on cash: -1.86% Traditional cash on cash: -1.69% Airbnb Rental Income: $617 Traditional Rental Income: $380 Airbnb ROI: -1.86% Traditional ROI: -1.69%
34.77 Acres Red Oak Est S Greencastle, PA 34.77 Acres Red Oak Est S, Greencastle, PA 17225 \| Other	N/A beds \| N/A baths \| N/A	$1,999,900	Airbnb cash on cash: -2.45% Traditional cash on cash: -2.42% Airbnb Rental Income: $617 Traditional Rental Income: $380 Airbnb ROI: -2.45% Traditional ROI: -2.42%
Molly Pitcher Greencastle, PA Molly Pitcher, Greencastle, PA 17225 \| Other	N/A beds \| N/A baths \| N/A	$375,000	Airbnb cash on cash: -1.9% Traditional cash on cash: 0.26% Airbnb Rental Income: $617 Traditional Rental Income: $1086 Airbnb ROI: -1.9% Traditional ROI: 0.26%
2579 Castlegreen Greencastle, PA	N/A beds \| N/A baths \| N/A	$89,900	Airbnb cash on cash: 0.12% Traditional cash on cash: 8.77% Airbnb Rental Income: $617 Traditional Rental Income: $1086 Airbnb ROI: 0.12% Traditional ROI: 8.77%
260 Baumgardner Dr Greencastle, PA 260 Baumgardner Dr, Greencastle, PA 17225 \| Single Family Residential	3 beds \| 2 baths \| 1,950 sq.ft.	$349,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.45% Airbnb Rental Income: $null Traditional Rental Income: $1736 Airbnb ROI: N/A Traditional ROI: 2.45%

Real Estate investment in Greencastle, PA

There are 43 properties for sale in the city of Greencastle . The median list price in Greencastle is $310,000 and the average price per square foot is $146. In March 2026, the average monthly cash on cash return in Greencastle is 3.00%. The average monthly rental income in Greencastle is $2,092.

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

There are 43 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 $2,092.

Your search for investment property begins and ends here

Investment Property for Sale in Greencastle, PA

250 East Madison St

Greencastle, PA

3 beds | 1 baths | 2,440 sq.ft.

$305,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.79%

Airbnb Rental Income: $null

Traditional Rental Income: $1581

Airbnb ROI: N/A

Traditional ROI: 2.79%

2384 Castlegreen Dr

Greencastle, PA

4 beds | 3 baths | 4,666 sq.ft.

$625,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.67%

Airbnb Rental Income: $null

Traditional Rental Income: $2296

Airbnb ROI: N/A

Traditional ROI: 1.67%

543 RAEANN DR

Greencastle, PA

4 beds | 3 baths | N/A

$335,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5%

Airbnb Rental Income: $null

Traditional Rental Income: $2301

Airbnb ROI: N/A

Traditional ROI: 5%

1401 Shannon Dr S

Greencastle, PA

3 beds | 2 baths | 2,000 sq.ft.

$470,871

Airbnb cash on cash: N/A

Traditional cash on cash: 4.17%

Airbnb Rental Income: $null

Traditional Rental Income: $2513

Airbnb ROI: N/A

Traditional ROI: 4.17%

171 East Ave

Greencastle, PA

1 beds | N/A baths | 1,920 sq.ft.

$275,000

Airbnb cash on cash: -0.63%

Traditional cash on cash: 4.57%

Airbnb Rental Income: $623

Traditional Rental Income: $1697

Airbnb ROI: -0.63%

Traditional ROI: 4.57%

1864 Shannon Dr S

Greencastle, PA

3 beds | 3 baths | 2,255 sq.ft.

$425,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.14%

Airbnb Rental Income: $null

Traditional Rental Income: $2628

Airbnb ROI: N/A

Traditional ROI: 4.14%

14732 Cedarbrook Dr

Greencastle, PA

4 beds | 2 baths | N/A

$399,999

Airbnb cash on cash: N/A

Traditional cash on cash: 5.35%

Airbnb Rental Income: $null

Traditional Rental Income: $2941

Airbnb ROI: N/A

Traditional ROI: 5.35%

341 W BALTIMORE STREET

Greencastle, PA

2 beds | 1 baths | N/A

$275,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.47%

Airbnb Rental Income: $null

Traditional Rental Income: $1647

Airbnb ROI: N/A