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 St MIDDLETOWN, MD Carefully reimagined between 2018 and 2021, this historic Main Street home now lives like ...	4 beds \| 3 baths \| 3,130 sq.ft.	$1,150,000	Airbnb cash on cash: 0.22% Traditional cash on cash: 1.99% Airbnb Rental Income: $2875 Traditional Rental Income: $4105 Airbnb ROI: 0.22% Traditional ROI: 1.99%
5 Dean Ln MIDDLETOWN, MD One level living at its finest! Ryan Homes offers this 1 story Brentwood with endless poss...	4 beds \| 4 baths \| 4,497 sq.ft.	$849,000	Airbnb cash on cash: 0.48% Traditional cash on cash: 1.51% Airbnb Rental Income: $2875 Traditional Rental Income: $3024 Airbnb ROI: 0.48% Traditional ROI: 1.51%
106 Prospect St MIDDLETOWN, MD Classic 1920s Arts & Crafts style 3 BR home in downtown Middletown. Original owner. Stucc...	3 beds \| 1 baths \| 1,734 sq.ft.	$495,000	Airbnb cash on cash: 0.61% Traditional cash on cash: 0.66% Airbnb Rental Income: $1547 Traditional Rental Income: $1123 Airbnb ROI: 0.61% Traditional ROI: 0.66%
4 Lamar Ln MIDDLETOWN, MD Welcome home to 4 Lamar Lane, a beautifully updated Admar-built rancher tucked away at the...	2 beds \| 2 baths \| 1,359 sq.ft.	$475,000	Airbnb cash on cash: 0.19% Traditional cash on cash: 1.67% Airbnb Rental Income: $1635 Traditional Rental Income: $1831 Airbnb ROI: 0.19% Traditional ROI: 1.67%
2802 Bidle Rd MIDDLETOWN, MD Looking for new construction, but don't want to wait? This gorgeous 2025 built Craftsman i...	5 beds \| 4 baths \| 5,511 sq.ft.	$1,475,000	Airbnb cash on cash: -0.73% Traditional cash on cash: 1.6% Airbnb Rental Income: $2090 Traditional Rental Income: $4751 Airbnb ROI: -0.73% Traditional ROI: 1.6%
2730 Marker Rd MIDDLETOWN, MD Love history? Love farming? Love Middletown Valley? This trifecta is for YOU! Once a b...	5 beds \| 2 baths \| 3,112 sq.ft.	$1,300,000	Airbnb cash on cash: -0.66% Traditional cash on cash: 0.21% Airbnb Rental Income: $2090 Traditional Rental Income: $2593 Airbnb ROI: -0.66% Traditional ROI: 0.21%
3150 Bidle Rd MIDDLETOWN, MD 3150 Bidle Rd, MIDDLETOWN, MD 21769 \| Single Family Residential	5 beds \| 5 baths \| 6,026 sq.ft.	$1,719,900	Airbnb cash on cash: -1.17% Traditional cash on cash: -0.29% Airbnb Rental Income: $2090 Traditional Rental Income: $2956 Airbnb ROI: -1.17% Traditional ROI: -0.29%
3130 Bidle Rd MIDDLETOWN, MD 3130 Bidle Rd, MIDDLETOWN, MD 21769 \| Single Family Residential	4 beds \| 3 baths \| 3,052 sq.ft.	$1,249,900	Airbnb cash on cash: -0.26% Traditional cash on cash: -0.05% Airbnb Rental Income: $2875 Traditional Rental Income: $2454 Airbnb ROI: -0.26% Traditional ROI: -0.05%
3213 Old National Pike MIDDLETOWN, MD Price Improvement! This iconic 1937 Brick Tudor Revival residence and adjacent additional ...	3 beds \| 2 baths \| 1,782 sq.ft.	$659,000	Airbnb cash on cash: 0.02% Traditional cash on cash: 3.26% Airbnb Rental Income: $1547 Traditional Rental Income: $3096 Airbnb ROI: 0.02% Traditional ROI: 3.26%
7453 Heritage Oak Ter MIDDLETOWN, MD 7453 Heritage Oak Ter, MIDDLETOWN, MD 21769 \| Single Family Residential	4 beds \| 3 baths \| 4,413 sq.ft.	$1,349,900	Airbnb cash on cash: -0.4% Traditional cash on cash: -0.21% Airbnb Rental Income: $2875 Traditional Rental Income: $2441 Airbnb ROI: -0.4% Traditional ROI: -0.21%
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: -0.99% Traditional cash on cash: 0.09% Airbnb Rental Income: $1547 Traditional Rental Income: $2095 Airbnb ROI: -0.99% 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: 1.04% Traditional cash on cash: 3.63% Airbnb Rental Income: $2090 Traditional Rental Income: $2763 Airbnb ROI: 1.04% Traditional ROI: 3.63%
7 Derr Ln MIDDLETOWN, MD NEW PRICE! Welcome to 7 Derr Lane in the sought-after Villages at Foxfield-Middletown's pr...	3 beds \| 2 baths \| 2,208 sq.ft.	$625,000	Airbnb cash on cash: -0.52% Traditional cash on cash: 2.6% Airbnb Rental Income: $1547 Traditional Rental Income: $2921 Airbnb ROI: -0.52% Traditional ROI: 2.6%
Mountain Church Rd MIDDLETOWN, MD HOME TO BE BUILT. Nestled on a beautiful, wooded 2.25-acre lot, this to-be-built home by G...	3 beds \| 2 baths \| 3,000 sq.ft.	$924,500	Airbnb cash on cash: 0.01% Traditional cash on cash: 2.13% Airbnb Rental Income: $1547 Traditional Rental Income: $2925 Airbnb ROI: 0.01% Traditional ROI: 2.13%
9237 Frostown Rd MIDDLETOWN, MD Experience the flow of space and harmony a private 5-acre sanctuary where mid-century soul...	4 beds \| 4 baths \| 6,578 sq.ft.	$2,500,000	Airbnb cash on cash: -0.5% Traditional cash on cash: 0.84% Airbnb Rental Income: $2875 Traditional Rental Income: $5321 Airbnb ROI: -0.5% 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 \| 3 baths \| 5,366 sq.ft.	$1,200,000	Airbnb cash on cash: -0.05% Traditional cash on cash: 1% Airbnb Rental Income: $2875 Traditional Rental Income: $3371 Airbnb ROI: -0.05% Traditional ROI: 1%
8 N Pointe Ter MIDDLETOWN, MD Exceptional value in North Pointe! One of the largest models in the neighborhood, this upd...	4 beds \| 3 baths \| 5,674 sq.ft.	$739,900	Airbnb cash on cash: 0.84% Traditional cash on cash: 2.98% Airbnb Rental Income: $2875 Traditional Rental Income: $3683 Airbnb ROI: 0.84% Traditional ROI: 2.98%
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: -0.16% Traditional cash on cash: 0.07% Airbnb Rental Income: $2875 Traditional Rental Income: $2469 Airbnb ROI: -0.16% 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: -0.19% Traditional cash on cash: 1.74% Airbnb Rental Income: $663 Traditional Rental Income: $640 Airbnb ROI: -0.19% 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: 0.28% Traditional cash on cash: 2.4% Airbnb Rental Income: $2090 Traditional Rental Income: $2862 Airbnb ROI: 0.28% Traditional ROI: 2.4%
2748 Bennies Hill Rd MIDDLETOWN, MD Welcome to your own private retreat! This 3-bedroom, 3 full bath home offers nearly 2,500 ...	3 beds \| 3 baths \| 2,451 sq.ft.	$575,000	Airbnb cash on cash: -0.01% Traditional cash on cash: 3.23% Airbnb Rental Income: $1547 Traditional Rental Income: $2841 Airbnb ROI: -0.01% Traditional ROI: 3.23%
33 E Main St MIDDLETOWN, MD 33 E Main St, MIDDLETOWN, MD 21769 \| Single Family Residential	6 beds \| 2 baths \| 3,034 sq.ft.	$375,000	Airbnb cash on cash: 2.07% Traditional cash on cash: 4.31% Airbnb Rental Income: $2090 Traditional Rental Income: $2341 Airbnb ROI: 2.07% Traditional ROI: 4.31%
3160 Sumantown Rd MIDDLETOWN, MD 3160 Sumantown Rd, MIDDLETOWN, MD 21769 \| Single Family Residential	4 beds \| 3 baths \| 3,374 sq.ft.	$969,127	Airbnb cash on cash: 0.26% Traditional cash on cash: 0.67% Airbnb Rental Income: $2875 Traditional Rental Income: $2574 Airbnb ROI: 0.26% Traditional ROI: 0.67%
708 E Main St MIDDLETOWN, MD 708 E Main St, MIDDLETOWN, MD 21769 \| Single Family Residential	4 beds \| 2 baths \| 2,036 sq.ft.	$499,000	Airbnb cash on cash: 2.45% Traditional cash on cash: 2.41% Airbnb Rental Income: $2875 Traditional Rental Income: $2187 Airbnb ROI: 2.45% Traditional ROI: 2.41%
22 E Green St MIDDLETOWN, MD 22 E Green St, MIDDLETOWN, MD 21769 \| Townhouse	3 beds \| 2 baths \| 1,912 sq.ft.	$525,000	Airbnb cash on cash: -0.03% Traditional cash on cash: 1.54% Airbnb Rental Income: $1547 Traditional Rental Income: $1873 Airbnb ROI: -0.03% Traditional ROI: 1.54%
400 Stone Springs Ln MIDDLETOWN, MD 400 Stone Springs Ln, MIDDLETOWN, MD 21769 \| Townhouse	4 beds \| 3 baths \| 2,640 sq.ft.	$439,900	Airbnb cash on cash: 2.83% Traditional cash on cash: 3.64% Airbnb Rental Income: $2875 Traditional Rental Income: $2538 Airbnb ROI: 2.83% Traditional ROI: 3.64%
200 Prospect St MIDDLETOWN, MD 200 Prospect St, MIDDLETOWN, MD 21769 \| Single Family Residential	5 beds \| 3 baths \| 3,206 sq.ft.	$699,000	Airbnb cash on cash: 0.16% Traditional cash on cash: 2.33% Airbnb Rental Income: $2090 Traditional Rental Income: $2972 Airbnb ROI: 0.16% Traditional ROI: 2.33%
9001 Hollow Rd MIDDLETOWN, MD 9001 Hollow Rd, MIDDLETOWN, MD 21769 \| Single Family Residential	4 beds \| 3 baths \| 1,432 sq.ft.	$499,900	Airbnb cash on cash: 2.44% Traditional cash on cash: 2.97% Airbnb Rental Income: $2875 Traditional Rental Income: $2456 Airbnb ROI: 2.44% Traditional ROI: 2.97%
408 Stone Springs Ln MIDDLETOWN, MD 408 Stone Springs Ln, MIDDLETOWN, MD 21769 \| Townhouse	4 beds \| 3 baths \| 3,930 sq.ft.	$419,000	Airbnb cash on cash: 3.06% Traditional cash on cash: 3.48% Airbnb Rental Income: $2875 Traditional Rental Income: $2373 Airbnb ROI: 3.06% Traditional ROI: 3.48%
323 S Jefferson St S MIDDLETOWN, MD 323 S Jefferson St S, MIDDLETOWN, MD 21769 \| Single Family Residential	3 beds \| 2 baths \| 1,000 sq.ft.	$369,000	Airbnb cash on cash: 0.83% Traditional cash on cash: 2.5% Airbnb Rental Income: $1547 Traditional Rental Income: $1678 Airbnb ROI: 0.83% Traditional ROI: 2.5%
718 E Main St MIDDLETOWN, MD 718 E Main St, MIDDLETOWN, MD 21769 \| Single Family Residential	4 beds \| 2 baths \| 1,862 sq.ft.	$499,900	Airbnb cash on cash: 2.44% Traditional cash on cash: 2.18% Airbnb Rental Income: $2875 Traditional Rental Income: $2087 Airbnb ROI: 2.44% Traditional ROI: 2.18%
108 S Jefferson St MIDDLETOWN, MD 108 S Jefferson St, MIDDLETOWN, MD 21769 \| Single Family Residential	3 beds \| 1 baths \| 1,390 sq.ft.	$235,000	Airbnb cash on cash: 2.46% Traditional cash on cash: 3.61% Airbnb Rental Income: $1547 Traditional Rental Income: $1356 Airbnb ROI: 2.46% Traditional ROI: 3.61%
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: -0.14% Traditional cash on cash: 3.39% Airbnb Rental Income: $2875 Traditional Rental Income: $6805 Airbnb ROI: -0.14% 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: 2.89% Traditional cash on cash: 3.39% Airbnb Rental Income: $2875 Traditional Rental Income: $2431 Airbnb ROI: 2.89% 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: 0.47% Traditional cash on cash: 2.94% Airbnb Rental Income: $2090 Traditional Rental Income: $2994 Airbnb ROI: 0.47% Traditional ROI: 2.94%
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: -0.01% Traditional cash on cash: 2.17% Airbnb Rental Income: $2090 Traditional Rental Income: $3133 Airbnb ROI: -0.01% Traditional ROI: 2.17%

Real Estate investment in Middletown, MD

There are 40 properties for sale in the city of Middletown . The median list price in Middletown is $559,915 and the average price per square foot is $283. In August 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 40 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 $2,090.

Your search for investment property begins and ends here

Investment Property for Sale in Middletown, MD

19 E Main St

MIDDLETOWN, MD

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

$1,150,000

Airbnb cash on cash: 0.22%

Traditional cash on cash: 1.99%

Airbnb Rental Income: $2875

Traditional Rental Income: $4105

Airbnb ROI: 0.22%

Traditional ROI: 1.99%

5 Dean Ln

MIDDLETOWN, MD

4 beds | 4 baths | 4,497 sq.ft.

$849,000

Airbnb cash on cash: 0.48%

Traditional cash on cash: 1.51%

Airbnb Rental Income: $2875

Traditional Rental Income: $3024

Airbnb ROI: 0.48%

Traditional ROI: 1.51%

106 Prospect St

MIDDLETOWN, MD

3 beds | 1 baths | 1,734 sq.ft.

$495,000

Airbnb cash on cash: 0.61%

Traditional cash on cash: 0.66%

Airbnb Rental Income: $1547

Traditional Rental Income: $1123

Airbnb ROI: 0.61%

Traditional ROI: 0.66%

4 Lamar Ln

MIDDLETOWN, MD

2 beds | 2 baths | 1,359 sq.ft.

$475,000

Airbnb cash on cash: 0.19%

Traditional cash on cash: 1.67%

Airbnb Rental Income: $1635

Traditional Rental Income: $1831

Airbnb ROI: 0.19%

Traditional ROI: 1.67%

2802 Bidle Rd

MIDDLETOWN, MD

5 beds | 4 baths | 5,511 sq.ft.

$1,475,000

Airbnb cash on cash: -0.73%

Traditional cash on cash: 1.6%

Airbnb Rental Income: $2090

Traditional Rental Income: $4751

Airbnb ROI: -0.73%

Traditional ROI: 1.6%

2730 Marker Rd

MIDDLETOWN, MD

5 beds | 2 baths | 3,112 sq.ft.

$1,300,000

Airbnb cash on cash: -0.66%

Traditional cash on cash: 0.21%

Airbnb Rental Income: $2090

Traditional Rental Income: $2593

Airbnb ROI: -0.66%

Traditional ROI: 0.21%

3150 Bidle Rd

MIDDLETOWN, MD

5 beds | 5 baths | 6,026 sq.ft.

$1,719,900

Airbnb cash on cash: -1.17%

Traditional cash on cash: -0.29%

Airbnb Rental Income: $2090

Traditional Rental Income: $2956

Airbnb ROI: -1.17%

Traditional ROI: -0.29%

3130 Bidle Rd

MIDDLETOWN, MD

4 beds | 3 baths | 3,052 sq.ft.

$1,249,900

Airbnb cash on cash: -0.26%

Traditional cash on cash: -0.05%

Airbnb Rental Income: $2875

Traditional Rental Income: $2454

Airbnb ROI: -0.26%