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

separator

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: -1.56% Traditional cash on cash: 0.83% Airbnb Rental Income: $50 Traditional Rental Income: $1302 Airbnb ROI: -1.56% Traditional ROI: 0.83%
7231 Friendship Rd 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%
7434 Cemetery Ave Pittsville, MD Motivated seller bring offers!! ***Seller is offering buyer $9,000 seller concession towar...	2 beds \| 1 baths \| 960 sq.ft.	$308,950	Airbnb cash on cash: 1.66% Traditional cash on cash: 6.39% Airbnb Rental Income: $1524 Traditional Rental Income: $2458 Airbnb ROI: 1.66% Traditional ROI: 6.39%
8304 & 8344 Gumboro Rd Pittsville, MD 8304 & 8344 Gumboro Rd, Pittsville, MD 21850 \| Single Family Residential	4 beds \| 2 baths \| 2,828 sq.ft.	$816,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.93% Airbnb Rental Income: $null Traditional Rental Income: $2382 Airbnb ROI: N/A Traditional ROI: 0.93%
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: -3.49% Traditional cash on cash: 2.61% Airbnb Rental Income: $50 Traditional Rental Income: $891 Airbnb ROI: -3.49% Traditional ROI: 2.61%
6728 Friendship Rd Pittsville, MD 6728 Friendship Rd, Pittsville, MD 21850 \| Single Family Residential	7 beds \| 7 baths \| 6,892 sq.ft.	$695,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.89% Airbnb Rental Income: $null Traditional Rental Income: $5907 Airbnb ROI: N/A Traditional ROI: 6.89%
34292 West St Pittsville, MD 34292 West St, Pittsville, MD 21850 \| Other	N/A beds \| N/A baths \| 0 sq.ft.	$550,000	Airbnb cash on cash: -2.53% Traditional cash on cash: -0.11% Airbnb Rental Income: $50 Traditional Rental Income: $1154 Airbnb ROI: -2.53% Traditional ROI: -0.11%
5045 Powellville Rd Pittsville, MD 5045 Powellville Rd, Pittsville, MD 21850 \| Other	N/A beds \| N/A baths \| 0 sq.ft.	$215,000	Airbnb cash on cash: -3.26% Traditional cash on cash: 3.13% Airbnb Rental Income: $50 Traditional Rental Income: $1154 Airbnb ROI: -3.26% Traditional ROI: 3.13%
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: $50 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	$124,900	Airbnb cash on cash: -4.07% Traditional cash on cash: 4.85% Airbnb Rental Income: $50 Traditional Rental Income: $925 Airbnb ROI: -4.07% Traditional ROI: 4.85%
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: -2.41% Traditional cash on cash: -0.97% Airbnb Rental Income: $50 Traditional Rental Income: $925 Airbnb ROI: -2.41% Traditional ROI: -0.97%

Real Estate investment in Pittsville, MD

There are 11 properties for sale in the city of Pittsville . The median list price in Pittsville is $309,900 and the average price per square foot is $152. In February 2026, the average monthly cash on cash return in Pittsville is 3.00%. The average monthly rental income in Pittsville is $1,154.

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

There are 11 investment properties available for sale in Pittsville.

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

The ROI for Long-Term is higher than the Short-Term in Pittsville with average rental income of $1,154.

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: -1.56%

Traditional cash on cash: 0.83%

Airbnb Rental Income: $50

Traditional Rental Income: $1302

Airbnb ROI: -1.56%

Traditional ROI: 0.83%

7231 Friendship Rd

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%

7434 Cemetery Ave

Pittsville, MD

2 beds | 1 baths | 960 sq.ft.

$308,950

Airbnb cash on cash: 1.66%

Traditional cash on cash: 6.39%

Airbnb Rental Income: $1524

Traditional Rental Income: $2458

Airbnb ROI: 1.66%

Traditional ROI: 6.39%

8304 & 8344 Gumboro Rd

Pittsville, MD

4 beds | 2 baths | 2,828 sq.ft.

$816,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.93%

Airbnb Rental Income: $null

Traditional Rental Income: $2382

Airbnb ROI: N/A

Traditional ROI: 0.93%

Casher Wells Rd

Pittsville, MD

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

$179,000

Airbnb cash on cash: -3.49%

Traditional cash on cash: 2.61%

Airbnb Rental Income: $50

Traditional Rental Income: $891

Airbnb ROI: -3.49%

Traditional ROI: 2.61%

6728 Friendship Rd

Pittsville, MD

7 beds | 7 baths | 6,892 sq.ft.

$695,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.89%

Airbnb Rental Income: $null

Traditional Rental Income: $5907

Airbnb ROI: N/A

Traditional ROI: 6.89%

34292 West St

Pittsville, MD

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

$550,000

Airbnb cash on cash: -2.53%

Traditional cash on cash: -0.11%

Airbnb Rental Income: $50

Traditional Rental Income: $1154

Airbnb ROI: -2.53%

Traditional ROI: -0.11%

5045 Powellville Rd

Pittsville, MD

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

$215,000

Airbnb cash on cash: -3.26%

Traditional cash on cash: 3.13%

Airbnb Rental Income: $50

Traditional Rental Income: $1154

Airbnb ROI: -3.26%