Real Estate Investment Properties for Sale in Pittsville, MD

Looking for investment property in Pittsville, MD with high ROI ?

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
7235 Sixty Foot Rd Pittsville, MD Great Investment Opportunity! 31.72+/- acre lot in Pittsville. Sale includes 3 parcels: 27...	N/A beds \| N/A baths \| N/A	$650,000	Airbnb cash on cash: -1.57% Traditional cash on cash: 0.83% Airbnb Rental Income: $48 Traditional Rental Income: $1302 Airbnb ROI: -1.57% Traditional ROI: 0.83%
7231 FRIENDSHIP Road Pittsville, MD Adorable Ranch Home - Move-In Ready! This charming ranch-style home features four spacious...	4 beds \| 2 baths \| 1,592 sq.ft.	$309,900	Airbnb cash on cash: N/A Traditional cash on cash: 7.17% Airbnb Rental Income: $null Traditional Rental Income: $2647 Airbnb ROI: N/A Traditional ROI: 7.17%
Casher Wells Rd Pittsville, MD Casher Wells Rd, Pittsville, MD 21850 \| Other	N/A beds \| N/A baths \| N/A	$179,000	Airbnb cash on cash: -3.5% Traditional cash on cash: 2.61% Airbnb Rental Income: $48 Traditional Rental Income: $891 Airbnb ROI: -3.5% Traditional ROI: 2.61%
5045 Powellville Rd Pittsville, MD 5045 Powellville Rd, Pittsville, MD 21850 \| Other	N/A beds \| N/A baths \| 0 sq.ft.	$210,000	Airbnb cash on cash: -3.29% Traditional cash on cash: 3.25% Airbnb Rental Income: $48 Traditional Rental Income: $1154 Airbnb ROI: -3.29% Traditional ROI: 3.25%
34350 Main St Pittsville, MD 34350 Main St, Pittsville, MD 21850 \| Other	N/A beds \| N/A baths \| N/A	$212,000	Airbnb cash on cash: -3.28% Traditional cash on cash: 2.06% Airbnb Rental Income: $48 Traditional Rental Income: $925 Airbnb ROI: -3.28% Traditional ROI: 2.06%
Lot 3 Main St Pittsville, MD Lot 3 Main St, Pittsville, MD 21850 \| Other	N/A beds \| N/A baths \| N/A	$99,900	Airbnb cash on cash: -4.56% Traditional cash on cash: 6.49% Airbnb Rental Income: $48 Traditional Rental Income: $925 Airbnb ROI: -4.56% Traditional ROI: 6.49%
Lot 3B Powellville Whiton Rd Pittsville, MD Lot 3B Powellville Whiton Rd, Pittsville, MD 21850 \| Other	N/A beds \| N/A baths \| N/A	$749,990	Airbnb cash on cash: -2.43% Traditional cash on cash: -0.89% Airbnb Rental Income: $48 Traditional Rental Income: $925 Airbnb ROI: -2.43% Traditional ROI: -0.89%
7250 CHATHAM MANOR Way Pittsville, MD Well-maintained 3 bedroom, 2 bath rancher on corner lot in Chatham Manor. Vinyl siding, he...	3 beds \| 2 baths \| 1,165 sq.ft.	$285,000	Airbnb cash on cash: 2.01% Traditional cash on cash: 6.28% Airbnb Rental Income: $1605 Traditional Rental Income: $2294 Airbnb ROI: 2.01% Traditional ROI: 6.28%
7745 Gumboro Rd Pittsville, MD 7745 Gumboro Rd, Pittsville, MD 21850 \| Other	N/A beds \| N/A baths \| N/A	$460,000	Airbnb cash on cash: -2.64% Traditional cash on cash: 0.1% Airbnb Rental Income: $48 Traditional Rental Income: $1032 Airbnb ROI: -2.64% Traditional ROI: 0.1%
35837 BOB KELLY Road Pittsville, MD Welcome to peaceful country living with room to grow! Nestled on 3.7 scenic acres in a qui...	2 beds \| 1 baths \| 800 sq.ft.	$304,900	Airbnb cash on cash: 0.35% Traditional cash on cash: 4.32% Airbnb Rental Income: $914 Traditional Rental Income: $1713 Airbnb ROI: 0.35% Traditional ROI: 4.32%
34764 SANDYFIELD Drive Pittsville, MD Entering the driveway on Sandyfield Drive in Pittsville, this well-kept 3-bedroom, 2-bath ...	3 beds \| 2 baths \| 1,226 sq.ft.	$310,000	Airbnb cash on cash: 1.81% Traditional cash on cash: 5.95% Airbnb Rental Income: $1605 Traditional Rental Income: $2355 Airbnb ROI: 1.81% Traditional ROI: 5.95%
34863 RAILROAD Avenue Pittsville, MD Opportunity awaits on 1.24 acres! This 3-bedroom, 2-bath home offers 1,288 sq. ft. and sit...	3 beds \| 2 baths \| 1,288 sq.ft.	$259,900	Airbnb cash on cash: 2.41% Traditional cash on cash: 6.67% Airbnb Rental Income: $1605 Traditional Rental Income: $2194 Airbnb ROI: 2.41% Traditional ROI: 6.67%
35534 MOUNT HERMON RD Pittsville, MD Adorable home on almost 2 acres and in great location - close to shopping dining and event...	2 beds \| 1 baths \| N/A	$194,900	Airbnb cash on cash: 1.06% Traditional cash on cash: 6.34% Airbnb Rental Income: $914 Traditional Rental Income: $1550 Airbnb ROI: 1.06% Traditional ROI: 6.34%

Real Estate investment in Pittsville, MD

There are 13 properties for sale in the city of Pittsville . The median list price in Pittsville is $272,450 and the average price per square foot is $251. In May 2026, the average monthly cash on cash return in Pittsville is 4.00%. The average monthly rental income in Pittsville is $2,166.

Pittsville, MD Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 13 investment properties available for sale in Pittsville.

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

The ROI for Short-Term is higher than the Long-Term in Pittsville with average rental income of $1,605.

Your search for investment property begins and ends here

Investment Property for Sale in Pittsville, MD

7235 Sixty Foot Rd

Pittsville, MD

N/A beds | N/A baths | N/A

$650,000

Airbnb cash on cash: -1.57%

Traditional cash on cash: 0.83%

Airbnb Rental Income: $48

Traditional Rental Income: $1302

Airbnb ROI: -1.57%

Traditional ROI: 0.83%

7231 FRIENDSHIP Road

Pittsville, MD

4 beds | 2 baths | 1,592 sq.ft.

$309,900

Airbnb cash on cash: N/A

Traditional cash on cash: 7.17%

Airbnb Rental Income: $null

Traditional Rental Income: $2647

Airbnb ROI: N/A

Traditional ROI: 7.17%

Casher Wells Rd

Pittsville, MD

N/A beds | N/A baths | N/A

$179,000

Airbnb cash on cash: -3.5%

Traditional cash on cash: 2.61%

Airbnb Rental Income: $48

Traditional Rental Income: $891

Airbnb ROI: -3.5%

Traditional ROI: 2.61%

5045 Powellville Rd

Pittsville, MD

N/A beds | N/A baths | 0 sq.ft.

$210,000

Airbnb cash on cash: -3.29%

Traditional cash on cash: 3.25%

Airbnb Rental Income: $48

Traditional Rental Income: $1154

Airbnb ROI: -3.29%

Traditional ROI: 3.25%

34350 Main St

Pittsville, MD

N/A beds | N/A baths | N/A

$212,000

Airbnb cash on cash: -3.28%

Traditional cash on cash: 2.06%

Airbnb Rental Income: $48

Traditional Rental Income: $925

Airbnb ROI: -3.28%

Traditional ROI: 2.06%

Lot 3 Main St

Pittsville, MD

N/A beds | N/A baths | N/A

$99,900

Airbnb cash on cash: -4.56%

Traditional cash on cash: 6.49%

Airbnb Rental Income: $48

Traditional Rental Income: $925

Airbnb ROI: -4.56%

Traditional ROI: 6.49%

Lot 3B Powellville Whiton Rd

Pittsville, MD

N/A beds | N/A baths | N/A

$749,990

Airbnb cash on cash: -2.43%

Traditional cash on cash: -0.89%

Airbnb Rental Income: $48

Traditional Rental Income: $925

Airbnb ROI: -2.43%

Traditional ROI: -0.89%

7250 CHATHAM MANOR Way

Pittsville, MD

3 beds | 2 baths | 1,165 sq.ft.

$285,000

Airbnb cash on cash: 2.01%

Traditional cash on cash: 6.28%

Airbnb Rental Income: $1605

Traditional Rental Income: $2294

Airbnb ROI: 2.01%