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
6 GAVER Way MIDDLETOWN, MD Welcome to this stunning residence, where over 5,500 square feet of thoughtfully designed ...	5 beds \| 6 baths \| 5,510 sq.ft.	$820,000	Airbnb cash on cash: -1.43% Traditional cash on cash: 6.67% Airbnb Rental Income: $1218 Traditional Rental Income: $7012 Airbnb ROI: -1.43% Traditional ROI: 6.67%
2 LOMBARDY Drive MIDDLETOWN, MD Welcome to 2 Lombardy Drive, right in the heart of Middletown's Woodmere neighborhood-just...	3 beds \| 2 baths \| 2,079 sq.ft.	$499,999	Airbnb cash on cash: -0.98% Traditional cash on cash: 3.52% Airbnb Rental Income: $836 Traditional Rental Income: $2611 Airbnb ROI: -0.98% Traditional ROI: 3.52%
4209 MARYLAND CT MIDDLETOWN, MD Welcome to 4209 Maryland Court, a stunning retreat nestled in the hills of the Middletown ...	4 beds \| 6 baths \| N/A	$1,400,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.39% Airbnb Rental Income: $null Traditional Rental Income: $6805 Airbnb ROI: N/A Traditional ROI: 3.39%
6838 Mountain Church Rd MIDDLETOWN, MD Live like you're on vacation everyday & prepare to fall in love with this private and gorg...	4 beds \| 3 baths \| 2,488 sq.ft.	$639,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.33% Airbnb Rental Income: $null Traditional Rental Income: $2508 Airbnb ROI: N/A Traditional ROI: 2.33%
503 Glenbrook Dr MIDDLETOWN, MD Hurry to this Middletown Glenbrook Beauty with an in-ground salt water pool! Spend the s...	4 beds \| 3 baths \| 4,892 sq.ft.	$885,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.15% Airbnb Rental Income: $null Traditional Rental Income: $2595 Airbnb ROI: N/A Traditional ROI: 1.15%
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.	$399,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.41% Airbnb Rental Income: $null Traditional Rental Income: $2634 Airbnb ROI: N/A Traditional ROI: 4.41%
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	$1,395,000	Airbnb cash on cash: -1.24% Traditional cash on cash: 0.12% Airbnb Rental Income: $1218 Traditional Rental Income: $2593 Airbnb ROI: -1.24% Traditional ROI: 0.12%
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: -1.69% Traditional cash on cash: -0.53% Airbnb Rental Income: $1218 Traditional Rental Income: $2956 Airbnb ROI: -1.69% 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: 0.06% Airbnb Rental Income: $null Traditional Rental Income: $2454 Airbnb ROI: N/A Traditional ROI: 0.06%
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%
3213 OLD NATIONAL Pike MIDDLETOWN, MD Price Improvement! This iconic 1937 Brick Tudor Revival residence and adjacent additional ...	3 beds \| 3 baths \| 1,782 sq.ft.	$699,900	Airbnb cash on cash: -0.95% Traditional cash on cash: 3.02% Airbnb Rental Income: $836 Traditional Rental Income: $3096 Airbnb ROI: -0.95% Traditional ROI: 3.02%
7453 Heritage Oak Ter MIDDLETOWN, MD 7453 Heritage Oak Ter, MIDDLETOWN, MD 21769 \| Single Family Residential	3 beds \| 3 baths \| 2,790 sq.ft.	$1,297,167	Airbnb cash on cash: -1.74% Traditional cash on cash: -0.14% Airbnb Rental Income: $836 Traditional Rental Income: $2441 Airbnb ROI: -1.74% Traditional ROI: -0.14%
8939 Hawbottom Rd MIDDLETOWN, MD 8939 Hawbottom Rd, MIDDLETOWN, MD 21769 \| Single Family Residential	3 beds \| 3 baths \| 3,236 sq.ft.	$989,000	Airbnb cash on cash: -1.63% Traditional cash on cash: 0.09% Airbnb Rental Income: $836 Traditional Rental Income: $2095 Airbnb ROI: -1.63% Traditional ROI: 0.09%
7 DERR Lane MIDDLETOWN, MD Welcome to 7 Derr Lane in the sought-after Villages at Foxfield-Middletown's premier 55+ c...	3 beds \| 3 baths \| 2,208 sq.ft.	$675,000	Airbnb cash on cash: -1.49% Traditional cash on cash: 2.34% Airbnb Rental Income: $836 Traditional Rental Income: $2921 Airbnb ROI: -1.49% Traditional ROI: 2.34%
MOUNTAIN CHURCH Road MIDDLETOWN, MD HOME TO BE BUILT. Nestled on a beautiful, wooded 2.25-acre lot, this to-be-built home by G...	3 beds \| 3 baths \| 3,000 sq.ft.	$924,500	Airbnb cash on cash: -0.68% Traditional cash on cash: 2.13% Airbnb Rental Income: $836 Traditional Rental Income: $2925 Airbnb ROI: -0.68% Traditional ROI: 2.13%
307 WASHINGTON ST MIDDLETOWN, MD Now on market! This picturesque single-family home sits in the heart of beautiful histori...	5 beds \| 4 baths \| N/A	$645,000	Airbnb cash on cash: -0.79% Traditional cash on cash: 2.82% Airbnb Rental Income: $1218 Traditional Rental Income: $2994 Airbnb ROI: -0.79% Traditional ROI: 2.82%
216 E MAIN Street MIDDLETOWN, MD Featured in WASHINGTONIAN, this iconic Victorian "Painted Lady" in the heart of Middletown...	5 beds \| 6 baths \| 3,296 sq.ft.	$775,000	Airbnb cash on cash: -1.33% Traditional cash on cash: 7.91% Airbnb Rental Income: $1218 Traditional Rental Income: $7499 Airbnb ROI: -1.33% Traditional ROI: 7.91%
208 Main St MIDDLETOWN, MD 208 Main St, MIDDLETOWN, MD 21769 \| Single Family Residential	4 beds \| 2 baths \| 1,616 sq.ft.	$374,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.43% Airbnb Rental Income: $null Traditional Rental Income: $2031 Airbnb ROI: N/A Traditional ROI: 3.43%
7460 Heritage Oak Ter MIDDLETOWN, MD 7460 Heritage Oak Ter, MIDDLETOWN, MD 21769 \| Single Family Residential	4 beds \| 3 baths \| 3,782 sq.ft.	$1,664,378	Airbnb cash on cash: N/A Traditional cash on cash: -0.55% Airbnb Rental Income: $null Traditional Rental Income: $2466 Airbnb ROI: N/A Traditional ROI: -0.55%
110 STONE SPRINGS LN MIDDLETOWN, MD Open House Saturday and Sunday 1-3pm. Beautifully updated townhome in sought after Glenbro...	4 beds \| 4 baths \| N/A	$435,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.74% Airbnb Rental Income: $null Traditional Rental Income: $2497 Airbnb ROI: N/A Traditional ROI: 3.74%
3204 Bidle Rd MIDDLETOWN, MD 3204 Bidle Rd, MIDDLETOWN, MD 21769 \| Single Family Residential	2 beds \| 1 baths \| 1,200 sq.ft.	$250,000	Airbnb cash on cash: -0.41% Traditional cash on cash: 2.53% Airbnb Rental Income: $810 Traditional Rental Income: $1182 Airbnb ROI: -0.41% Traditional ROI: 2.53%
4432 VALLEY VIEW Road MIDDLETOWN, MD Don't miss out on this very well maintained all-brick rancher situated on a level, half ac...	3 beds \| 3 baths \| 1,232 sq.ft.	$479,900	Airbnb cash on cash: -0.78% Traditional cash on cash: 3.85% Airbnb Rental Income: $836 Traditional Rental Income: $2588 Airbnb ROI: -0.78% Traditional ROI: 3.85%
6419 ZITTLESTOWN RD MIDDLETOWN, MD NO HOA and NO CITY TAXES! Charming cottage-style home nestled on a scenic .38-acre lot, lo...	2 beds \| 1 baths \| N/A	$235,000	Airbnb cash on cash: 0.11% Traditional cash on cash: 4.34% Airbnb Rental Income: $810 Traditional Rental Income: $1425 Airbnb ROI: 0.11% Traditional ROI: 4.34%

Real Estate investment in Middletown, MD

There are 24 properties for sale in the city of Middletown . The median list price in Middletown is $417,500 and the average price per square foot is $223. In May 2026, the average monthly cash on cash return in Middletown is 3.00%. The average monthly rental income in Middletown is $2,594.

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

There are 24 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 $2,594.

Your search for investment property begins and ends here

Investment Property for Sale in Middletown, MD

6 GAVER Way

MIDDLETOWN, MD

5 beds | 6 baths | 5,510 sq.ft.

$820,000

Airbnb cash on cash: -1.43%

Traditional cash on cash: 6.67%

Airbnb Rental Income: $1218

Traditional Rental Income: $7012

Airbnb ROI: -1.43%

Traditional ROI: 6.67%

2 LOMBARDY Drive

MIDDLETOWN, MD

3 beds | 2 baths | 2,079 sq.ft.

$499,999

Airbnb cash on cash: -0.98%

Traditional cash on cash: 3.52%

Airbnb Rental Income: $836

Traditional Rental Income: $2611

Airbnb ROI: -0.98%

Traditional ROI: 3.52%

4209 MARYLAND CT

MIDDLETOWN, MD

4 beds | 6 baths | N/A

$1,400,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.39%

Airbnb Rental Income: $null

Traditional Rental Income: $6805

Airbnb ROI: N/A

Traditional ROI: 3.39%

6838 Mountain Church Rd

MIDDLETOWN, MD

4 beds | 3 baths | 2,488 sq.ft.

$639,900

Airbnb cash on cash: N/A

Traditional cash on cash: 2.33%

Airbnb Rental Income: $null

Traditional Rental Income: $2508

Airbnb ROI: N/A

Traditional ROI: 2.33%

503 Glenbrook Dr

MIDDLETOWN, MD

4 beds | 3 baths | 4,892 sq.ft.

$885,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.15%

Airbnb Rental Income: $null

Traditional Rental Income: $2595

Airbnb ROI: N/A

Traditional ROI: 1.15%

1936 OLD NATIONAL Pike

MIDDLETOWN, MD

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

$399,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.41%

Airbnb Rental Income: $null

Traditional Rental Income: $2634

Airbnb ROI: N/A

Traditional ROI: 4.41%

2730 MARKER RD

MIDDLETOWN, MD

5 beds | 2 baths | N/A

$1,395,000

Airbnb cash on cash: -1.24%

Traditional cash on cash: 0.12%

Airbnb Rental Income: $1218

Traditional Rental Income: $2593

Airbnb ROI: -1.24%

Traditional ROI: 0.12%

3150 Bidle Rd

MIDDLETOWN, MD

5 beds | 4 baths | 5,153 sq.ft.

$1,990,900

Airbnb cash on cash: -1.69%

Traditional cash on cash: -0.53%

Airbnb Rental Income: $1218

Traditional Rental Income: $2956

Airbnb ROI: -1.69%