Real Estate Investment Properties for Sale in Preston, MD

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
4784 Birch Dr PRESTON, MD This spacious rancher is move-in condition and sited on just over an acre of land. With o...	3 beds \| N/A baths \| 1,620 sq.ft.	$239,999	Airbnb cash on cash: N/A Traditional cash on cash: 6.46% Airbnb Rental Income: $null Traditional Rental Income: $1950 Airbnb ROI: N/A Traditional ROI: 6.46%
23116 GILPIN POINT Road PRESTON, MD A perfectly situated, water-oriented, turnkey, rancher with a piece of country is ready fo...	4 beds \| 2 baths \| 1,880 sq.ft.	$434,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.56% Airbnb Rental Income: $null Traditional Rental Income: $2638 Airbnb ROI: N/A Traditional ROI: 4.56%
22403 MARSH CREEK Road PRESTON, MD Custom Brick rancher, close to town on large lot. Open floor plan, spacious kitchen, stain...	3 beds \| 2 baths \| 1,448 sq.ft.	$379,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.78% Airbnb Rental Income: $null Traditional Rental Income: $2337 Airbnb ROI: N/A Traditional ROI: 4.78%
5585 HARMONY WOODS Drive PRESTON, MD Set on a private, wooded 1.37+/- acre lot in Harmony Woods, this beautifully maintained ho...	4 beds \| 3 baths \| 3,442 sq.ft.	$549,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.43% Airbnb Rental Income: $null Traditional Rental Income: $3345 Airbnb ROI: N/A Traditional ROI: 4.43%
20915 Dover Bridge Rd PRESTON, MD 8.6 acres with lots of possibilities just across the Dover Bridge and its scenic view of t...	3 beds \| 2 baths \| 1,904 sq.ft.	$447,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.54% Airbnb Rental Income: $null Traditional Rental Income: $2737 Airbnb ROI: N/A Traditional ROI: 4.54%
5026 Bethlehem Rd PRESTON, MD Back on the market at no fault of seller! Colonial Home in Preston on a corner lot. This h...	3 beds \| 2 baths \| 1,922 sq.ft.	$339,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.51% Airbnb Rental Income: $null Traditional Rental Income: $2321 Airbnb ROI: N/A Traditional ROI: 5.51%
215 Apple Ln PRESTON, MD Welcome to 215 Apple Lane. This well-maintained Cape Cod with over 1500 sq feet of living ...	3 beds \| 2 baths \| 1,575 sq.ft.	$369,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.88% Airbnb Rental Income: $null Traditional Rental Income: $2412 Airbnb ROI: N/A Traditional ROI: 4.88%
22408 HOG CREEK Road PRESTON, MD NEW PRICE! Enjoy peace and space on two tranquil country acres with no deed restrictions a...	3 beds \| 4 baths \| 2,667 sq.ft.	$469,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.01% Airbnb Rental Income: $null Traditional Rental Income: $3542 Airbnb ROI: N/A Traditional ROI: 6.01%
21245 TANYARD Road PRESTON, MD Charming Country Living with Room to Make It Your Own! Welcome to 21245 Tanyard Road, a sp...	3 beds \| 3 baths \| 2,128 sq.ft.	$275,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.36% Airbnb Rental Income: $null Traditional Rental Income: $2521 Airbnb ROI: N/A Traditional ROI: 7.36%
2697 CHOPTANK MAIN Street PRESTON, MD Charming Renovated Home in Choptank, Preston MD. This home currently has a fresh coat of i...	2 beds \| 2 baths \| 1,104 sq.ft.	$279,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.13% Airbnb Rental Income: $null Traditional Rental Income: $2150 Airbnb ROI: N/A Traditional ROI: 6.13%
7837 SHORE Drive PRESTON, MD Two Johns - Charming Home in a Sought-After Waterfront Community Nestled between Preston a...	4 beds \| 3 baths \| 1,920 sq.ft.	$495,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.37% Airbnb Rental Income: $null Traditional Rental Income: $2936 Airbnb ROI: N/A Traditional ROI: 4.37%
212 MAIN Street PRESTON, MD Welcome to this spacious and beautifully maintained property nestled in the peaceful town ...	5 beds \| 3 baths \| 2,122 sq.ft.	$235,000	Airbnb cash on cash: N/A Traditional cash on cash: 11.19% Airbnb Rental Income: $null Traditional Rental Income: $3028 Airbnb ROI: N/A Traditional ROI: 11.19%
4305 LANGRELL Road PRESTON, MD Welcome to this beautifully updated rancher that checks every box - and then some. Sitting...	4 beds \| 2 baths \| 2,076 sq.ft.	$350,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.71% Airbnb Rental Income: $null Traditional Rental Income: $2847 Airbnb ROI: N/A Traditional ROI: 6.71%
24383 ROBINS CREEK RD PRESTON, MD VERY NICE 3-4 BEDROOM, 2 BATH HOME IN TWO JOHNS WATERFRONT COMMUNITY. BOAT LANDING APPROXI...	4 beds \| 2 baths \| N/A	$375,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.79% Airbnb Rental Income: $null Traditional Rental Income: $2737 Airbnb ROI: N/A Traditional ROI: 5.79%
4215 Preston Rd PRESTON, MD 4215 Preston Rd, PRESTON, MD 21655 \| Single Family Residential	3 beds \| 2 baths \| 1,642 sq.ft.	$329,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.3% Airbnb Rental Income: $null Traditional Rental Income: $2065 Airbnb ROI: N/A Traditional ROI: 4.3%
162 Main St PRESTON, MD	N/A beds \| N/A baths \| N/A	$92,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.54% Airbnb Rental Income: $null Traditional Rental Income: $687 Airbnb ROI: N/A Traditional ROI: 4.54%
lot 6 Harmony Woods PRESTON, MD	N/A beds \| N/A baths \| N/A	$79,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.53% Airbnb Rental Income: $null Traditional Rental Income: $684 Airbnb ROI: N/A Traditional ROI: 5.53%
126 Maple Ave PRESTON, MD 126 Maple Ave, PRESTON, MD 21655 \| Single Family Residential	3 beds \| 1 baths \| 1,828 sq.ft.	$227,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.06% Airbnb Rental Income: $null Traditional Rental Income: $1412 Airbnb ROI: N/A Traditional ROI: 4.06%
22285 TANYARD Road PRESTON, MD Tucked away just outside of town, this charming 3-bedroom, 2-bathroom home offers the perf...	3 beds \| 2 baths \| 1,503 sq.ft.	$365,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.58% Airbnb Rental Income: $null Traditional Rental Income: $2571 Airbnb ROI: N/A Traditional ROI: 5.58%
21611 EVERLEA Drive PRESTON, MD Welcome to this estate sale opportunity offering convenient one-level living in a wonderfu...	3 beds \| 2 baths \| 1,568 sq.ft.	$349,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.28% Airbnb Rental Income: $null Traditional Rental Income: $2395 Airbnb ROI: N/A Traditional ROI: 5.28%

Real Estate investment in Preston, MD

There are 20 properties for sale in the city of Preston . The median list price in Preston is $414,900 and the average price per square foot is $212. In April 2026, the average monthly cash on cash return in Preston is 6.00%. The average monthly rental income in Preston is $2,395.

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

There are 20 investment properties available for sale in Preston.

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

Your search for investment property begins and ends here

Investment Property for Sale in Preston, MD

4784 Birch Dr

PRESTON, MD

3 beds | N/A baths | 1,620 sq.ft.

$239,999

Airbnb cash on cash: N/A

Traditional cash on cash: 6.46%

Airbnb Rental Income: $null

Traditional Rental Income: $1950

Airbnb ROI: N/A

Traditional ROI: 6.46%

23116 GILPIN POINT Road

PRESTON, MD

4 beds | 2 baths | 1,880 sq.ft.

$434,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.56%

Airbnb Rental Income: $null

Traditional Rental Income: $2638

Airbnb ROI: N/A

Traditional ROI: 4.56%

22403 MARSH CREEK Road

PRESTON, MD

3 beds | 2 baths | 1,448 sq.ft.

$379,900

Airbnb cash on cash: N/A

Traditional cash on cash: 4.78%

Airbnb Rental Income: $null

Traditional Rental Income: $2337

Airbnb ROI: N/A

Traditional ROI: 4.78%

5585 HARMONY WOODS Drive

PRESTON, MD

4 beds | 3 baths | 3,442 sq.ft.

$549,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.43%

Airbnb Rental Income: $null

Traditional Rental Income: $3345

Airbnb ROI: N/A

Traditional ROI: 4.43%

20915 Dover Bridge Rd

PRESTON, MD

3 beds | 2 baths | 1,904 sq.ft.

$447,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.54%

Airbnb Rental Income: $null

Traditional Rental Income: $2737

Airbnb ROI: N/A

Traditional ROI: 4.54%

5026 Bethlehem Rd

PRESTON, MD

3 beds | 2 baths | 1,922 sq.ft.

$339,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.51%

Airbnb Rental Income: $null

Traditional Rental Income: $2321

Airbnb ROI: N/A

Traditional ROI: 5.51%

215 Apple Ln

PRESTON, MD

3 beds | 2 baths | 1,575 sq.ft.

$369,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.88%

Airbnb Rental Income: $null

Traditional Rental Income: $2412

Airbnb ROI: N/A

Traditional ROI: 4.88%

22408 HOG CREEK Road

PRESTON, MD

3 beds | 4 baths | 2,667 sq.ft.

$469,900

Airbnb cash on cash: N/A

Traditional cash on cash: 6.01%

Airbnb Rental Income: $null

Traditional Rental Income: $3542

Airbnb ROI: N/A