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.

Single Family Homes for Sale in Middletown, MD

Search for Single Family Residential for Sale in Middletown, Maryland. Browse all of Mashvisor’s Single Family Residential listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 32 Single Family Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
19 E Main St MIDDLETOWN, MD Carefully reimagined between 2018 and 2021 with over $1.5M in updates, this historic Main ...	4 beds \| 3 baths \| 3,130 sq.ft.	$1,050,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.18% Airbnb Rental Income: $null Traditional Rental Income: $4105 Airbnb ROI: N/A Traditional ROI: 2.18%
5 Dean Ln MIDDLETOWN, MD Welcome to 5 Dean Lane, a stunning 4-bedroom, 4.5-bath home in the sought-after Middletown...	4 beds \| 4 baths \| 4,497 sq.ft.	$834,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.5% Airbnb Rental Income: $null Traditional Rental Income: $3024 Airbnb ROI: N/A Traditional ROI: 1.5%
12 Dean Ln MIDDLETOWN, MD The Torino plan at Middletown Glen with Ryan Homes. Boasting over 3400 sqft, 4 bedrm, spac...	4 beds \| 3 baths \| 3,142 sq.ft.	$675,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.35% Airbnb Rental Income: $null Traditional Rental Income: $2976 Airbnb ROI: N/A Traditional ROI: 2.35%
6838 Mountain Church Rd MIDDLETOWN, MD Escape the ordinary with this one-of-a-kind mountain-inspired retreat set on more than 5 s...	3 beds \| 3 baths \| 2,488 sq.ft.	$584,900	Airbnb cash on cash: 0.26% Traditional cash on cash: 2.63% Airbnb Rental Income: $1682 Traditional Rental Income: $2508 Airbnb ROI: 0.26% Traditional ROI: 2.63%
301 Cone Branch Dr MIDDLETOWN, MD *OPEN HOUSE Saturday, Sept. 16th, 12-2 p.m.*** A rare opportunity for a Cone Branch ...	4 beds \| 3 baths \| 3,822 sq.ft.	$665,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.56% Airbnb Rental Income: $null Traditional Rental Income: $3361 Airbnb ROI: N/A Traditional ROI: 3.56%
411 Glenbrook Dr MIDDLETOWN, MD EXCLUSIVE OPEN HOUSE OFFER 8/29 - Stop by the open house or call and ask for the details o...	4 beds \| 3 baths \| 4,603 sq.ft.	$774,900	Airbnb cash on cash: N/A Traditional cash on cash: 1.46% Airbnb Rental Income: $null Traditional Rental Income: $2759 Airbnb ROI: N/A Traditional ROI: 1.46%
2313 Bidle Rd MIDDLETOWN, MD Welcome to 2313 Bidle Rd! This beautiful home is situated on 23.1 picturesque acres of lan...	3 beds \| 3 baths \| 4,658 sq.ft.	$874,900	Airbnb cash on cash: -0.25% Traditional cash on cash: 0.79% Airbnb Rental Income: $1682 Traditional Rental Income: $2057 Airbnb ROI: -0.25% Traditional ROI: 0.79%
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.	$1,425,000	Airbnb cash on cash: -1.26% Traditional cash on cash: 1.69% Airbnb Rental Income: $1234 Traditional Rental Income: $4751 Airbnb ROI: -1.26% Traditional ROI: 1.69%
7820 Myersville Rd MIDDLETOWN, MD Room to Breathe, Space to Grow, and Mountain Views to Come Home To Set on 3.72 acres just ...	3 beds \| 2 baths \| 2,496 sq.ft.	$534,999	Airbnb cash on cash: 0.43% Traditional cash on cash: 4.22% Airbnb Rental Income: $1682 Traditional Rental Income: $3107 Airbnb ROI: 0.43% Traditional ROI: 4.22%
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: -1.62% Traditional cash on cash: -0.29% Airbnb Rental Income: $1234 Traditional Rental Income: $2956 Airbnb ROI: -1.62% Traditional ROI: -0.29%
3130 Bidle Rd MIDDLETOWN, MD To-be-Built. Set against the stunning backdrop of scenic Middletown Valley, Heritage Oak E...	4 beds \| 3 baths \| 3,052 sq.ft.	$1,249,900	Airbnb cash on cash: N/A Traditional cash on cash: -0.05% Airbnb Rental Income: $null Traditional Rental Income: $2454 Airbnb ROI: N/A Traditional ROI: -0.05%
3213 OLD NATIONAL Pike MIDDLETOWN, MD NEWLY PRICED!! Discover the convenience of spacious one-level living in this beautiful 3-b...	3 beds \| 3 baths \| 1,782 sq.ft.	$659,000	Airbnb cash on cash: 0.2% Traditional cash on cash: 3.26% Airbnb Rental Income: $1682 Traditional Rental Income: $3096 Airbnb ROI: 0.2% 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: N/A Traditional cash on cash: -0.21% Airbnb Rental Income: $null Traditional Rental Income: $2441 Airbnb ROI: N/A 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: -0.87% Traditional cash on cash: 0.09% Airbnb Rental Income: $1682 Traditional Rental Income: $2095 Airbnb ROI: -0.87% Traditional ROI: 0.09%
7 Derr Ln MIDDLETOWN, MD Welcome to 7 Derr Lane in the sought-after Villages at Foxfield-Middletown's premier 55+ c...	3 beds \| 2 baths \| 2,208 sq.ft.	$600,000	Airbnb cash on cash: -0.3% Traditional cash on cash: 2.75% Airbnb Rental Income: $1682 Traditional Rental Income: $2921 Airbnb ROI: -0.3% Traditional ROI: 2.75%
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: 0.14% Traditional cash on cash: 2.13% Airbnb Rental Income: $1682 Traditional Rental Income: $2925 Airbnb ROI: 0.14% 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.	$2,249,999	Airbnb cash on cash: N/A Traditional cash on cash: 1.05% Airbnb Rental Income: $null Traditional Rental Income: $5321 Airbnb ROI: N/A Traditional ROI: 1.05%
5901 Cloudberry Ct MIDDLETOWN, MD 5901 Cloudberry Ct, MIDDLETOWN, MD 21769 \| Single Family Residential	4 beds \| 3 baths \| 3,421 sq.ft.	$1,148,990	Airbnb cash on cash: N/A Traditional cash on cash: 0.14% Airbnb Rental Income: $null Traditional Rental Income: $2469 Airbnb ROI: N/A Traditional ROI: 0.14%
2748 Bennies Hill Rd MIDDLETOWN, MD Welcome to your own private retreat This 3-bedroom, 3 full bath home offers nearly 2,500 s...	3 beds \| 3 baths \| 2,451 sq.ft.	$575,000	Airbnb cash on cash: 0.2% Traditional cash on cash: 3.23% Airbnb Rental Income: $1682 Traditional Rental Income: $2841 Airbnb ROI: 0.2% Traditional ROI: 3.23%
708 E Main St MIDDLETOWN, MD Welcome to this charming 4-bedroom, 2-bathroom home ideally situated on Main Street in the...	4 beds \| 2 baths \| 2,036 sq.ft.	$475,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.5% Airbnb Rental Income: $null Traditional Rental Income: $2187 Airbnb ROI: N/A Traditional ROI: 2.5%
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: -0.94% Traditional cash on cash: 2.33% Airbnb Rental Income: $1234 Traditional Rental Income: $2972 Airbnb ROI: -0.94% Traditional ROI: 2.33%
9001 Hollow Rd MIDDLETOWN, MD One or more photos in this listing have been virtually staged using AI Completely Renova...	4 beds \| 3 baths \| 1,432 sq.ft.	$499,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.39% Airbnb Rental Income: $null Traditional Rental Income: $2456 Airbnb ROI: N/A Traditional ROI: 3.39%
718 E Main St MIDDLETOWN, MD Welcome to this beautiful colonial in the heart of Middletown, MD, where small-town charm,...	4 beds \| 2 baths \| 1,862 sq.ft.	$499,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.05% Airbnb Rental Income: $null Traditional Rental Income: $2087 Airbnb ROI: N/A Traditional ROI: 2.05%
319 S Church St MIDDLETOWN, MD OPEN HOUSE SATURDAY 8/29 11AM-1PM Welcome to this charming 3-bedroom home right across the...	3 beds \| 1 baths \| 1,824 sq.ft.	$350,000	Airbnb cash on cash: 0.99% Traditional cash on cash: 5.15% Airbnb Rental Income: $1682 Traditional Rental Income: $2579 Airbnb ROI: 0.99% Traditional ROI: 5.15%
7008 Mountain Church Rd MIDDLETOWN, MD Welcome to 7008 Mountain Church Road, a beautifully renovated and move-in-ready home offer...	2 beds \| 2 baths \| 1,200 sq.ft.	$335,000	Airbnb cash on cash: 2.11% Traditional cash on cash: 3.91% Airbnb Rental Income: $1831 Traditional Rental Income: $1905 Airbnb ROI: 2.11% Traditional ROI: 3.91%
7101 Flint Ct MIDDLETOWN, MD 7101 Flint Ct, MIDDLETOWN, MD 21769 \| Single Family Residential	3 beds \| 1 baths \| 1,473 sq.ft.	$415,000	Airbnb cash on cash: 0.8% Traditional cash on cash: 1.31% Airbnb Rental Income: $1682 Traditional Rental Income: $1411 Airbnb ROI: 0.8% Traditional ROI: 1.31%
1 Wagon Shed Ln MIDDLETOWN, MD	5 beds \| 5 baths \| 6,827 sq.ft.	$1,235,000	Airbnb cash on cash: -1.49% Traditional cash on cash: 1.54% Airbnb Rental Income: $1234 Traditional Rental Income: $4315 Airbnb ROI: -1.49% Traditional ROI: 1.54%
400 W Green St MIDDLETOWN, MD 400 W Green St, MIDDLETOWN, MD 21769 \| Single Family Residential	3 beds \| 2 baths \| 1,388 sq.ft.	$375,000	Airbnb cash on cash: 1.1% Traditional cash on cash: 2.97% Airbnb Rental Income: $1682 Traditional Rental Income: $1870 Airbnb ROI: 1.1% Traditional ROI: 2.97%
4492 Jade Ct MIDDLETOWN, MD 4492 Jade Ct, MIDDLETOWN, MD 21769 \| Single Family Residential	4 beds \| 2 baths \| 2,200 sq.ft.	$539,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.01% Airbnb Rental Income: $null Traditional Rental Income: $2159 Airbnb ROI: N/A Traditional ROI: 2.01%
117 Mina Dr MIDDLETOWN, MD 117 Mina Dr, MIDDLETOWN, MD 21769 \| Single Family Residential	4 beds \| 2 baths \| 3,164 sq.ft.	$765,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.01% Airbnb Rental Income: $null Traditional Rental Income: $2298 Airbnb ROI: N/A Traditional ROI: 1.01%
4613 Granite Dr MIDDLETOWN, MD 4613 Granite Dr, MIDDLETOWN, MD 21769 \| Single Family Residential	3 beds \| 3 baths \| 2,583 sq.ft.	$487,900	Airbnb cash on cash: 0.37% Traditional cash on cash: 3.19% Airbnb Rental Income: $1682 Traditional Rental Income: $2497 Airbnb ROI: 0.37% Traditional ROI: 3.19%
21 E Main St MIDDLETOWN, MD 21 E Main St, MIDDLETOWN, MD 21769 \| Single Family Residential	5 beds \| 3 baths \| 2,820 sq.ft.	$680,000	Airbnb cash on cash: -0.91% Traditional cash on cash: 2.09% Airbnb Rental Income: $1234 Traditional Rental Income: $2738 Airbnb ROI: -0.91% Traditional ROI: 2.09%

Your search for investment property begins and ends here

Single Family Homes for Sale in Middletown, MD

19 E Main St

MIDDLETOWN, MD

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

$1,050,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.18%

Airbnb Rental Income: $null

Traditional Rental Income: $4105

Airbnb ROI: N/A

Traditional ROI: 2.18%

5 Dean Ln

MIDDLETOWN, MD

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

$834,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.5%

Airbnb Rental Income: $null

Traditional Rental Income: $3024

Airbnb ROI: N/A

Traditional ROI: 1.5%

12 Dean Ln

MIDDLETOWN, MD

4 beds | 3 baths | 3,142 sq.ft.

$675,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.35%

Airbnb Rental Income: $null

Traditional Rental Income: $2976

Airbnb ROI: N/A

Traditional ROI: 2.35%

6838 Mountain Church Rd

MIDDLETOWN, MD

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

$584,900

Airbnb cash on cash: 0.26%

Traditional cash on cash: 2.63%

Airbnb Rental Income: $1682

Traditional Rental Income: $2508

Airbnb ROI: 0.26%

Traditional ROI: 2.63%

301 Cone Branch Dr

MIDDLETOWN, MD

4 beds | 3 baths | 3,822 sq.ft.

$665,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.56%

Airbnb Rental Income: $null

Traditional Rental Income: $3361

Airbnb ROI: N/A

Traditional ROI: 3.56%

411 Glenbrook Dr

MIDDLETOWN, MD

4 beds | 3 baths | 4,603 sq.ft.

$774,900

Airbnb cash on cash: N/A

Traditional cash on cash: 1.46%

Airbnb Rental Income: $null

Traditional Rental Income: $2759

Airbnb ROI: N/A

Traditional ROI: 1.46%

2313 Bidle Rd

MIDDLETOWN, MD

3 beds | 3 baths | 4,658 sq.ft.

$874,900

Airbnb cash on cash: -0.25%

Traditional cash on cash: 0.79%

Airbnb Rental Income: $1682

Traditional Rental Income: $2057

Airbnb ROI: -0.25%

Traditional ROI: 0.79%

2802 Bidle Rd

MIDDLETOWN, MD

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

$1,425,000

Airbnb cash on cash: -1.26%

Traditional cash on cash: 1.69%

Airbnb Rental Income: $1234

Traditional Rental Income: $4751

Airbnb ROI: -1.26%