Real Estate Investment Properties for Sale in Middletown, MD

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
1936 OLD NATIONAL Pike MIDDLETOWN, MD Motivated seller with a new price!!! Property sold as-is, offering upside potential in a g...	4 beds \| 2 baths \| 2,824 sq.ft.	$429,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.03% Airbnb Rental Income: $null Traditional Rental Income: $2634 Airbnb ROI: N/A Traditional ROI: 4.03%
417 W MAIN Street MIDDLETOWN, MD Price Improved and ready for you to make this your new home in 2026 !! Welcome to this del...	3 beds \| 1 baths \| 1,392 sq.ft.	$254,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.12% Airbnb Rental Income: $null Traditional Rental Income: $1664 Airbnb ROI: N/A Traditional ROI: 4.12%
25 CHESTER Court MIDDLETOWN, MD Welcome to 25 Chester Court in Middletown, MD, a stunning end unit townhome. This spacious...	3 beds \| 4 baths \| N/A	$444,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.69% Airbnb Rental Income: $null Traditional Rental Income: $3267 Airbnb ROI: N/A Traditional ROI: 4.69%
2730 MARKER RD MIDDLETOWN, MD Love history? Love farming? Love Middletown Valley? This trifecta is for YOU! Once a b...	5 beds \| 2 baths \| N/A	$1,500,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.05% Airbnb Rental Income: $null Traditional Rental Income: $2593 Airbnb ROI: N/A Traditional ROI: 0.05%
26 WALNUT ST MIDDLETOWN, MD Stunning new construction by Rachuba Homes in the heart of historic downtown Middletown. N...	4 beds \| 3 baths \| N/A	$699,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.38% Airbnb Rental Income: $null Traditional Rental Income: $3046 Airbnb ROI: N/A Traditional ROI: 3.38%
3213 OLD NATIONAL Pike MIDDLETOWN, MD A Truly Rare Opportunity! For the first time ever on the public market, the iconic 1937 Br...	3 beds \| 3 baths \| 1,782 sq.ft.	$750,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.75% Airbnb Rental Income: $null Traditional Rental Income: $3096 Airbnb ROI: N/A Traditional ROI: 2.75%
1629 DAHLGREN Road MIDDLETOWN, MD Charming brick rancher set on 4.64 acres with stunning views and exceptional potential. Th...	3 beds \| 1 baths \| 1,056 sq.ft.	$335,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.16% Airbnb Rental Income: $null Traditional Rental Income: $1702 Airbnb ROI: N/A Traditional ROI: 3.16%
4614 PINEWOOD TRAIL MIDDLETOWN, MD Well-maintained single-family home built in 1974 featuring a classic split foyer design. T...	3 beds \| 3 baths \| N/A	$440,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.25% Airbnb Rental Income: $null Traditional Rental Income: $2656 Airbnb ROI: N/A Traditional ROI: 4.25%
4302 SARATOGA SPRINGS Court MIDDLETOWN, MD Welcome to this exquisite Luxury Estate on two Private Acres! Experience the perfect blend...	4 beds \| 4 baths \| 5,698 sq.ft.	$1,250,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.18% Airbnb Rental Income: $null Traditional Rental Income: $3678 Airbnb ROI: N/A Traditional ROI: 1.18%
7201 DOGWOOD Lane MIDDLETOWN, MD Discover this charming 3-bedroom, 2-bath ranch home on a spacious 0.63-acre lot in the des...	3 beds \| 2 baths \| 1,651 sq.ft.	$371,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.11% Airbnb Rental Income: $null Traditional Rental Income: $2533 Airbnb ROI: N/A Traditional ROI: 5.11%
1676 MONUMENT RD MIDDLETOWN, MD OPEN HOUSE CANCELLED. Enjoy easy one-level living on 4.25 scenic acres in beautiful Middl...	5 beds \| 3 baths \| N/A	$675,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.11% Airbnb Rental Income: $null Traditional Rental Income: $3172 Airbnb ROI: N/A Traditional ROI: 3.11%
1 KELLER LN MIDDLETOWN, MD REFRESHED, REVAMPED AND MOVE-IN READY. YOU SPOKE AND WE LISTENED. CHECK IT OUT AGAIN! Th...	3 beds \| 3 baths \| N/A	$564,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.57% Airbnb Rental Income: $null Traditional Rental Income: $2567 Airbnb ROI: N/A Traditional ROI: 2.57%

Real Estate investment in Middletown, MD

There are 18 properties for sale in the city of Middletown . The median list price in Middletown is $410,000 and the average price per square foot is $229. In April 2026, the average monthly cash on cash return in Middletown is 4.00%. The average monthly rental income in Middletown is $2,656.

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

There are 18 investment properties available for sale in Middletown.

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

Your search for investment property begins and ends here

Investment Property for Sale in Middletown, MD

1936 OLD NATIONAL Pike

MIDDLETOWN, MD

4 beds | 2 baths | 2,824 sq.ft.

$429,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.03%

Airbnb Rental Income: $null

Traditional Rental Income: $2634

Airbnb ROI: N/A

Traditional ROI: 4.03%

417 W MAIN Street

MIDDLETOWN, MD

3 beds | 1 baths | 1,392 sq.ft.

$254,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.12%

Airbnb Rental Income: $null

Traditional Rental Income: $1664

Airbnb ROI: N/A

Traditional ROI: 4.12%

25 CHESTER Court

MIDDLETOWN, MD

3 beds | 4 baths | N/A

$444,900

Airbnb cash on cash: N/A

Traditional cash on cash: 4.69%

Airbnb Rental Income: $null

Traditional Rental Income: $3267

Airbnb ROI: N/A

Traditional ROI: 4.69%

2730 MARKER RD

MIDDLETOWN, MD

5 beds | 2 baths | N/A

$1,500,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.05%

Airbnb Rental Income: $null

Traditional Rental Income: $2593

Airbnb ROI: N/A

Traditional ROI: 0.05%

26 WALNUT ST

MIDDLETOWN, MD

4 beds | 3 baths | N/A

$699,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.38%

Airbnb Rental Income: $null

Traditional Rental Income: $3046

Airbnb ROI: N/A

Traditional ROI: 3.38%

3213 OLD NATIONAL Pike

MIDDLETOWN, MD

3 beds | 3 baths | 1,782 sq.ft.

$750,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.75%

Airbnb Rental Income: $null

Traditional Rental Income: $3096

Airbnb ROI: N/A

Traditional ROI: 2.75%

1629 DAHLGREN Road

MIDDLETOWN, MD

3 beds | 1 baths | 1,056 sq.ft.

$335,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.16%

Airbnb Rental Income: $null

Traditional Rental Income: $1702

Airbnb ROI: N/A

Traditional ROI: 3.16%

4614 PINEWOOD TRAIL

MIDDLETOWN, MD

3 beds | 3 baths | N/A

$440,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.25%

Airbnb Rental Income: $null

Traditional Rental Income: $2656

Airbnb ROI: N/A