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
19 E MAIN Street MIDDLETOWN, MD Carefully reimagined between 2018 and 2021, this historic Main Street home now lives like ...	4 beds \| 4 baths \| 3,130 sq.ft.	$1,150,000	Airbnb cash on cash: -0.28% Traditional cash on cash: 1.99% Airbnb Rental Income: $2230 Traditional Rental Income: $4105 Airbnb ROI: -0.28% Traditional ROI: 1.99%
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.	$624,900	Airbnb cash on cash: 0.97% Traditional cash on cash: 2.4% Airbnb Rental Income: $2230 Traditional Rental Income: $2508 Airbnb ROI: 0.97% Traditional ROI: 2.4%
2802 BIDLE Road MIDDLETOWN, MD Looking for new construction, but don't want to wait? This gorgeous 2025 built Craftsman i...	5 beds \| 5 baths \| 5,511 sq.ft.	$1,500,000	Airbnb cash on cash: -1.11% Traditional cash on cash: 1.56% Airbnb Rental Income: $1461 Traditional Rental Income: $4751 Airbnb ROI: -1.11% Traditional ROI: 1.56%
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: -1.08% Traditional cash on cash: 0.12% Airbnb Rental Income: $1461 Traditional Rental Income: $2593 Airbnb ROI: -1.08% Traditional ROI: 0.12%
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: -0.47% Traditional cash on cash: 3.02% Airbnb Rental Income: $1216 Traditional Rental Income: $3096 Airbnb ROI: -0.47% Traditional ROI: 3.02%
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: -1.29% Traditional cash on cash: 0.09% Airbnb Rental Income: $1216 Traditional Rental Income: $2095 Airbnb ROI: -1.29% Traditional ROI: 0.09%
8209 Old Hagerstown Rd MIDDLETOWN, MD 8209 Old Hagerstown Rd, MIDDLETOWN, MD 21769 \| Single Family Residential	5 beds \| 3 baths \| 2,312 sq.ft.	$499,900	Airbnb cash on cash: -0.08% Traditional cash on cash: 3.63% Airbnb Rental Income: $1461 Traditional Rental Income: $2763 Airbnb ROI: -0.08% Traditional ROI: 3.63%
7 DERR Lane MIDDLETOWN, MD NEW PRICE! Welcome to 7 Derr Lane in the sought-after Villages at Foxfield-Middletown's pr...	3 beds \| 3 baths \| 2,208 sq.ft.	$650,000	Airbnb cash on cash: -0.99% Traditional cash on cash: 2.47% Airbnb Rental Income: $1216 Traditional Rental Income: $2921 Airbnb ROI: -0.99% Traditional ROI: 2.47%
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: -0.31% Traditional cash on cash: 2.13% Airbnb Rental Income: $1216 Traditional Rental Income: $2925 Airbnb ROI: -0.31% Traditional ROI: 2.13%
110 STONE SPRINGS LN MIDDLETOWN, MD Beautifully updated townhome in sought after Glenbrook community backing to the Richland G...	4 beds \| 4 baths \| N/A	$435,000	Airbnb cash on cash: 1.7% Traditional cash on cash: 3.74% Airbnb Rental Income: $2230 Traditional Rental Income: $2497 Airbnb ROI: 1.7% Traditional ROI: 3.74%
9237 FROSTOWN Road MIDDLETOWN, MD Experience the flow of space and harmony a private 5-acre sanctuary where mid-century soul...	4 beds \| 5 baths \| 6,578 sq.ft.	$2,500,000	Airbnb cash on cash: -0.73% Traditional cash on cash: 0.84% Airbnb Rental Income: $2230 Traditional Rental Income: $5321 Airbnb ROI: -0.73% Traditional ROI: 0.84%
4311 SARATOGA SPRINGS CT MIDDLETOWN, MD Tucked away at the end of a quiet cul-de-sac within the prestigious Vistas at Springdale o...	4 beds \| 4 baths \| N/A	$1,200,000	Airbnb cash on cash: -0.5% Traditional cash on cash: 1.03% Airbnb Rental Income: $2230 Traditional Rental Income: $3371 Airbnb ROI: -0.5% Traditional ROI: 1.03%
8 N POINTE Terrace MIDDLETOWN, MD Exceptional value in North Pointe! One of the largest models in the neighborhood, this upd...	4 beds \| 4 baths \| 5,674 sq.ft.	$749,900	Airbnb cash on cash: 0.05% Traditional cash on cash: 2.93% Airbnb Rental Income: $2230 Traditional Rental Income: $3683 Airbnb ROI: 0.05% Traditional ROI: 2.93%
5901 Cloudberry Ct MIDDLETOWN, MD 5901 Cloudberry Ct, MIDDLETOWN, MD 21769 \| Single Family Residential	4 beds \| 3 baths \| 3,600 sq.ft.	$1,185,000	Airbnb cash on cash: -0.65% Traditional cash on cash: 0.07% Airbnb Rental Income: $2230 Traditional Rental Income: $2469 Airbnb ROI: -0.65% Traditional ROI: 0.07%
Lot 1 E Green St MIDDLETOWN, MD Lot 1 E Green St, MIDDLETOWN, MD 21769 \| Other	N/A beds \| N/A baths \| N/A	$150,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.74% Airbnb Rental Income: $null Traditional Rental Income: $640 Airbnb ROI: N/A Traditional ROI: 1.74%
24 Young Branch Dr MIDDLETOWN, MD 24 Young Branch Dr, MIDDLETOWN, MD 21769 \| Single Family Residential	6 beds \| 3 baths \| 3,696 sq.ft.	$662,000	Airbnb cash on cash: -0.57% Traditional cash on cash: 2.4% Airbnb Rental Income: $1461 Traditional Rental Income: $2862 Airbnb ROI: -0.57% Traditional ROI: 2.4%
2 DERR Lane MIDDLETOWN, MD Welcome to 2 Derr Lane, a beautifully maintained home nestled in the highly sought-after F...	3 beds \| 3 baths \| 2,279 sq.ft.	$555,000	Airbnb cash on cash: -1.05% Traditional cash on cash: 2.93% Airbnb Rental Income: $1216 Traditional Rental Income: $2887 Airbnb ROI: -1.05% Traditional ROI: 2.93%
8613 HOLLOW RD MIDDLETOWN, MD OPEN HOUSE! Sunday, 6/14 from 1-3 pm *** Looking for the perfect spot to HOMESTEAD? This...	5 beds \| 4 baths \| N/A	$779,000	Airbnb cash on cash: -0.73% Traditional cash on cash: 2.17% Airbnb Rental Income: $1461 Traditional Rental Income: $3133 Airbnb ROI: -0.73% Traditional ROI: 2.17%
7430 Dogwood Ln MIDDLETOWN, MD 7430 Dogwood Ln, MIDDLETOWN, MD 21769 \| Single Family Residential	5 beds \| 3 baths \| 5,695 sq.ft.	$1,395,000	Airbnb cash on cash: -1.36% Traditional cash on cash: 0.03% Airbnb Rental Income: $1461 Traditional Rental Income: $2831 Airbnb ROI: -1.36% Traditional ROI: 0.03%
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: -0.56% Traditional cash on cash: 3.39% Airbnb Rental Income: $2230 Traditional Rental Income: $6805 Airbnb ROI: -0.56% Traditional ROI: 3.39%
7291 BEECHTREE LN MIDDLETOWN, MD Offers please in by Friday @ noon! Beautifully updated 4-bedroom, 2.5-bath split foyer wi...	4 beds \| 3 baths \| N/A	$475,000	Airbnb cash on cash: 1.68% Traditional cash on cash: 3.39% Airbnb Rental Income: $2230 Traditional Rental Income: $2431 Airbnb ROI: 1.68% Traditional ROI: 3.39%
307 WASHINGTON ST MIDDLETOWN, MD PRICE TO SELL This picturesque single-family home sits in the heart of beautiful histor...	5 beds \| 4 baths \| N/A	$625,000	Airbnb cash on cash: -0.43% Traditional cash on cash: 2.94% Airbnb Rental Income: $1461 Traditional Rental Income: $2994 Airbnb ROI: -0.43% Traditional ROI: 2.94%
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: 1.99% Traditional cash on cash: 4.34% Airbnb Rental Income: $1311 Traditional Rental Income: $1425 Airbnb ROI: 1.99% Traditional ROI: 4.34%

Real Estate investment in Middletown, MD

There are 31 properties for sale in the city of Middletown . The median list price in Middletown is $566,208 and the average price per square foot is $296. In June 2026, the average monthly cash on cash return in Middletown is 3.00%. The average monthly rental income in Middletown is $2,847.

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

There are 31 investment properties available for sale in Middletown.

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

The ROI for Short-Term is higher than the Long-Term in Middletown with average rental income of $1,461.

Your search for investment property begins and ends here

Investment Property for Sale in Middletown, MD

19 E MAIN Street

MIDDLETOWN, MD

4 beds | 4 baths | 3,130 sq.ft.

$1,150,000

Airbnb cash on cash: -0.28%

Traditional cash on cash: 1.99%

Airbnb Rental Income: $2230

Traditional Rental Income: $4105

Airbnb ROI: -0.28%

Traditional ROI: 1.99%

6838 Mountain Church Rd

MIDDLETOWN, MD

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

$624,900

Airbnb cash on cash: 0.97%

Traditional cash on cash: 2.4%

Airbnb Rental Income: $2230

Traditional Rental Income: $2508

Airbnb ROI: 0.97%

Traditional ROI: 2.4%

2802 BIDLE Road

MIDDLETOWN, MD

5 beds | 5 baths | 5,511 sq.ft.

$1,500,000

Airbnb cash on cash: -1.11%

Traditional cash on cash: 1.56%

Airbnb Rental Income: $1461

Traditional Rental Income: $4751

Airbnb ROI: -1.11%

Traditional ROI: 1.56%

2730 MARKER RD

MIDDLETOWN, MD

5 beds | 2 baths | N/A

$1,395,000

Airbnb cash on cash: -1.08%

Traditional cash on cash: 0.12%

Airbnb Rental Income: $1461

Traditional Rental Income: $2593

Airbnb ROI: -1.08%

Traditional ROI: 0.12%

3213 OLD NATIONAL Pike

MIDDLETOWN, MD

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

$699,900

Airbnb cash on cash: -0.47%

Traditional cash on cash: 3.02%

Airbnb Rental Income: $1216

Traditional Rental Income: $3096

Airbnb ROI: -0.47%

Traditional ROI: 3.02%

8939 Hawbottom Rd

MIDDLETOWN, MD

3 beds | 3 baths | 3,236 sq.ft.

$989,000

Airbnb cash on cash: -1.29%

Traditional cash on cash: 0.09%

Airbnb Rental Income: $1216

Traditional Rental Income: $2095

Airbnb ROI: -1.29%

Traditional ROI: 0.09%

8209 Old Hagerstown Rd

MIDDLETOWN, MD

5 beds | 3 baths | 2,312 sq.ft.

$499,900

Airbnb cash on cash: -0.08%

Traditional cash on cash: 3.63%

Airbnb Rental Income: $1461

Traditional Rental Income: $2763

Airbnb ROI: -0.08%

Traditional ROI: 3.63%

7 DERR Lane

MIDDLETOWN, MD

3 beds | 3 baths | 2,208 sq.ft.

$650,000

Airbnb cash on cash: -0.99%

Traditional cash on cash: 2.47%

Airbnb Rental Income: $1216

Traditional Rental Income: $2921

Airbnb ROI: -0.99%