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
215 BROAD Street MIDDLETOWN, MD This well built, all brick rancher sits on a corner lot and is in excellent condition. It ...	4 beds \| 3 baths \| 2,580 sq.ft.	$570,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.31% Airbnb Rental Income: $null Traditional Rental Income: $3338 Airbnb ROI: N/A Traditional ROI: 4.31%
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 Welcome to this delightful 3-bedroom, 1-bath single-family home nestled on Main St. in the...	3 beds \| 1 baths \| 1,392 sq.ft.	$279,990	Airbnb cash on cash: 3.53% Traditional cash on cash: 3.66% Airbnb Rental Income: $2183 Traditional Rental Income: $1664 Airbnb ROI: 3.53% Traditional ROI: 3.66%
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: 0.76% Traditional cash on cash: 4.69% Airbnb Rental Income: $2183 Traditional Rental Income: $3267 Airbnb ROI: 0.76% Traditional ROI: 4.69%
1 KELLER LN MIDDLETOWN, MD Welcome to this beautifully maintained Dulaney model by ADMAR Custom Homes, located in the...	3 beds \| 3 baths \| N/A	$564,900	Airbnb cash on cash: 0.86% Traditional cash on cash: 2.64% Airbnb Rental Income: $2183 Traditional Rental Income: $2567 Airbnb ROI: 0.86% Traditional ROI: 2.64%
7129 LIMESTONE Lane MIDDLETOWN, MD Nestled in the charming Middletown community, this delightful split foyer home offers a pe...	4 beds \| 2 baths \| 1,396 sq.ft.	$399,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.9% Airbnb Rental Income: $null Traditional Rental Income: $2643 Airbnb ROI: N/A Traditional ROI: 4.9%
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%
100 LOMBARDY Drive MIDDLETOWN, MD Welcome to 100 Lombardy Drive, a beautifully maintained all-brick rancher built by Morgan-...	3 beds \| 2 baths \| 2,372 sq.ft.	$569,000	Airbnb cash on cash: 1% Traditional cash on cash: 2.87% Airbnb Rental Income: $2183 Traditional Rental Income: $2625 Airbnb ROI: 1% Traditional ROI: 2.87%
3105 Sumantown Rd MIDDLETOWN, MD 3105 Sumantown Rd, MIDDLETOWN, MD 21769 \| Single Family Residential	4 beds \| 3 baths \| 3,544 sq.ft.	$949,900	Airbnb cash on cash: N/A Traditional cash on cash: 0.98% Airbnb Rental Income: $null Traditional Rental Income: $2806 Airbnb ROI: N/A Traditional ROI: 0.98%
2431 Quebec School Rd MIDDLETOWN, MD	4 beds \| 3 baths \| 2,917 sq.ft.	$725,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.56% Airbnb Rental Income: $null Traditional Rental Income: $2557 Airbnb ROI: N/A Traditional ROI: 1.56%
5916 Cloudberry Ct MIDDLETOWN, MD 5916 Cloudberry Ct, MIDDLETOWN, MD 21769 \| Single Family Residential	4 beds \| 3 baths \| 3,956 sq.ft.	$1,328,015	Airbnb cash on cash: N/A Traditional cash on cash: 0.11% Airbnb Rental Income: $null Traditional Rental Income: $2806 Airbnb ROI: N/A Traditional ROI: 0.11%
3150 Bidle Rd MIDDLETOWN, MD 3150 Bidle Rd, MIDDLETOWN, MD 21769 \| Single Family Residential	5 beds \| 4 baths \| 5,153 sq.ft.	$1,990,900	Airbnb cash on cash: N/A Traditional cash on cash: -0.53% Airbnb Rental Income: $null Traditional Rental Income: $2956 Airbnb ROI: N/A Traditional ROI: -0.53%
3130 Bidle Rd MIDDLETOWN, MD 3130 Bidle Rd, MIDDLETOWN, MD 21769 \| Single Family Residential	4 beds \| 3 baths \| 2,500 sq.ft.	$1,186,202	Airbnb cash on cash: N/A Traditional cash on cash: 0.38% Airbnb Rental Income: $null Traditional Rental Income: $2806 Airbnb ROI: N/A Traditional ROI: 0.38%
3120 Bidle Rd MIDDLETOWN, MD 3120 Bidle Rd, MIDDLETOWN, MD 21769 \| Single Family Residential	4 beds \| 3 baths \| 3,871 sq.ft.	$1,578,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.52% Airbnb Rental Income: $null Traditional Rental Income: $2387 Airbnb ROI: N/A Traditional ROI: -0.52%
Lot 2 Sumantown Rd MIDDLETOWN, MD Lot 2 Sumantown Rd, MIDDLETOWN, MD 21769 \| Single Family Residential	3 beds \| 2 baths \| 3,200 sq.ft.	$940,865	Airbnb cash on cash: -0.33% Traditional cash on cash: -0.45% Airbnb Rental Income: $2183 Traditional Rental Income: $1522 Airbnb ROI: -0.33% Traditional ROI: -0.45%
8511 Rosebud Ct MIDDLETOWN, MD 8511 Rosebud Ct, MIDDLETOWN, MD 21769 \| Other	N/A beds \| N/A baths \| N/A	$325,000	Airbnb cash on cash: 0.71% Traditional cash on cash: -0.57% Airbnb Rental Income: $1360 Traditional Rental Income: $555 Airbnb ROI: 0.71% Traditional ROI: -0.57%
9702 Mount Tabor - Lot 11 Rd MIDDLETOWN, MD 9702 Mount Tabor - Lot 11 Rd, MIDDLETOWN, MD 21769 \| Other	N/A beds \| N/A baths \| N/A	$450,000	Airbnb cash on cash: -0.06% Traditional cash on cash: -1.11% Airbnb Rental Income: $1360 Traditional Rental Income: $501 Airbnb ROI: -0.06% Traditional ROI: -1.11%

Real Estate investment in Middletown, MD

There are 18 properties for sale in the city of Middletown . The median list price in Middletown is $429,450 and the average price per square foot is $248. In January 2026, the average monthly cash on cash return in Middletown is 2.00%. The average monthly rental income in Middletown is $2,634.

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

There are 18 investment properties available for sale in Middletown.

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

The ROI for Long-Term is higher than the Short-Term in Middletown with average rental income of $2,634.

Your search for investment property begins and ends here

Investment Property for Sale in Middletown, MD

215 BROAD Street

MIDDLETOWN, MD

4 beds | 3 baths | 2,580 sq.ft.

$570,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.31%

Airbnb Rental Income: $null

Traditional Rental Income: $3338

Airbnb ROI: N/A

Traditional ROI: 4.31%

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.

$279,990

Airbnb cash on cash: 3.53%

Traditional cash on cash: 3.66%

Airbnb Rental Income: $2183

Traditional Rental Income: $1664

Airbnb ROI: 3.53%

Traditional ROI: 3.66%

25 CHESTER Court

MIDDLETOWN, MD

3 beds | 4 baths | N/A

$444,900

Airbnb cash on cash: 0.76%

Traditional cash on cash: 4.69%

Airbnb Rental Income: $2183

Traditional Rental Income: $3267

Airbnb ROI: 0.76%

Traditional ROI: 4.69%

1 KELLER LN

MIDDLETOWN, MD

3 beds | 3 baths | N/A

$564,900

Airbnb cash on cash: 0.86%

Traditional cash on cash: 2.64%

Airbnb Rental Income: $2183

Traditional Rental Income: $2567

Airbnb ROI: 0.86%

Traditional ROI: 2.64%

7129 LIMESTONE Lane

MIDDLETOWN, MD

4 beds | 2 baths | 1,396 sq.ft.

$399,900

Airbnb cash on cash: N/A

Traditional cash on cash: 4.9%

Airbnb Rental Income: $null

Traditional Rental Income: $2643

Airbnb ROI: N/A

Traditional ROI: 4.9%

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%

100 LOMBARDY Drive

MIDDLETOWN, MD

3 beds | 2 baths | 2,372 sq.ft.

$569,000

Airbnb cash on cash: 1%

Traditional cash on cash: 2.87%

Airbnb Rental Income: $2183

Traditional Rental Income: $2625

Airbnb ROI: 1%