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
1246 MOUNTAIN CHURCH Road MIDDLETOWN, MD Charming Cape Cod on 3.56 Acres with Bonus Guest Home - Endless Potential Near the Appalac...	2 beds \| 1 baths \| 900 sq.ft.	$224,900	Airbnb cash on cash: 4.98% Traditional cash on cash: 6.25% Airbnb Rental Income: $1886 Traditional Rental Income: $1653 Airbnb ROI: 4.98% Traditional ROI: 6.25%
6527 MORNINGSIDE Court MIDDLETOWN, MD This charming brick rancher is located at the end of a cul-de-sac in sought after Middleto...	3 beds \| 3 baths \| 2,275 sq.ft.	$574,900	Airbnb cash on cash: 0.96% Traditional cash on cash: 2.18% Airbnb Rental Income: $2183 Traditional Rental Income: $2286 Airbnb ROI: 0.96% Traditional ROI: 2.18%
107 MINA Drive MIDDLETOWN, MD Welcome home to 107 Mina Drive - where comfort, style, and location come together beautifu...	4 beds \| 4 baths \| 3,680 sq.ft.	$775,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.68% Airbnb Rental Income: $null Traditional Rental Income: $2821 Airbnb ROI: N/A Traditional ROI: 1.68%
8842 HAWBOTTOM Road MIDDLETOWN, MD Welcome home to 8842 Hawbottom Road! This breathtaking property features a stunning custom...	3 beds \| 4 baths \| 3,477 sq.ft.	$2,200,000	Airbnb cash on cash: -0.99% Traditional cash on cash: -0.12% Airbnb Rental Income: $2183 Traditional Rental Income: $3406 Airbnb ROI: -0.99% Traditional ROI: -0.12%
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.	$299,990	Airbnb cash on cash: 3.23% Traditional cash on cash: 3.35% Airbnb Rental Income: $2183 Traditional Rental Income: $1664 Airbnb ROI: 3.23% Traditional ROI: 3.35%
3226 BIDLE Road MIDDLETOWN, MD Imagine relaxing on an refinished deck, listening to the birds, and watching wildlife as y...	3 beds \| 3 baths \| 1,820 sq.ft.	$649,000	Airbnb cash on cash: 0.62% Traditional cash on cash: 3.06% Airbnb Rental Income: $2183 Traditional Rental Income: $3108 Airbnb ROI: 0.62% Traditional ROI: 3.06%
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	$449,900	Airbnb cash on cash: 1.27% Traditional cash on cash: 5.16% Airbnb Rental Income: $2183 Traditional Rental Income: $3267 Airbnb ROI: 1.27% Traditional ROI: 5.16%
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	$574,900	Airbnb cash on cash: 0.83% Traditional cash on cash: 2.58% Airbnb Rental Income: $2183 Traditional Rental Income: $2567 Airbnb ROI: 0.83% Traditional ROI: 2.58%
11 GLADHILL Drive MIDDLETOWN, MD Highly Desired Foxfield of Middletown Neighborhood! Perched on a premium lot at the top of...	4 beds \| 4 baths \| 3,522 sq.ft.	$899,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.11% Airbnb Rental Income: $null Traditional Rental Income: $3667 Airbnb ROI: N/A Traditional ROI: 2.11%
95 E GREEN Street MIDDLETOWN, MD Welcome to 95 E Green Street, a beautifully designed home in Middletown. The main level bo...	4 beds \| 4 baths \| 2,748 sq.ft.	$669,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.26% Airbnb Rental Income: $null Traditional Rental Income: $3414 Airbnb ROI: N/A Traditional ROI: 3.26%
10 LINDEN Boulevard MIDDLETOWN, MD CHARMING RANCHER IN MIDDLETOWN, MD! Welcome home to this delightful 3-bedroom, 1.5-bath ra...	3 beds \| 2 baths \| 2,104 sq.ft.	$349,000	Airbnb cash on cash: 2.28% Traditional cash on cash: 5.11% Airbnb Rental Income: $2183 Traditional Rental Income: $2559 Airbnb ROI: 2.28% Traditional ROI: 5.11%
3 KELLER Lane MIDDLETOWN, MD These don't become available very often. Over 55 community in Middletown. Walking distance...	3 beds \| 4 baths \| 2,267 sq.ft.	$550,000	Airbnb cash on cash: 0.95% Traditional cash on cash: 3.55% Airbnb Rental Income: $2183 Traditional Rental Income: $2968 Airbnb ROI: 0.95% Traditional ROI: 3.55%
7442 DOGWOOD Lane MIDDLETOWN, MD Welcome to 7442 Dogwood Lane - a serene Lindal post-and-beam retreat with sweeping sunset ...	5 beds \| 4 baths \| 4,125 sq.ft.	$739,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.13% Airbnb Rental Income: $null Traditional Rental Income: $3831 Airbnb ROI: N/A Traditional ROI: 3.13%

Real Estate investment in Middletown, MD

There are 13 properties for sale in the city of Middletown . The median list price in Middletown is $574,900 and the average price per square foot is $223. In December 2025, the average monthly cash on cash return in Middletown is 3.00%. The average monthly rental income in Middletown is $2,728.

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

There are 13 investment properties available for sale in Middletown.

In 2025, 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 $2,728.

Your search for investment property begins and ends here

Investment Property for Sale in Middletown, MD

1246 MOUNTAIN CHURCH Road

MIDDLETOWN, MD

2 beds | 1 baths | 900 sq.ft.

$224,900

Airbnb cash on cash: 4.98%

Traditional cash on cash: 6.25%

Airbnb Rental Income: $1886

Traditional Rental Income: $1653

Airbnb ROI: 4.98%

Traditional ROI: 6.25%

6527 MORNINGSIDE Court

MIDDLETOWN, MD

3 beds | 3 baths | 2,275 sq.ft.

$574,900

Airbnb cash on cash: 0.96%

Traditional cash on cash: 2.18%

Airbnb Rental Income: $2183

Traditional Rental Income: $2286

Airbnb ROI: 0.96%

Traditional ROI: 2.18%

107 MINA Drive

MIDDLETOWN, MD

4 beds | 4 baths | 3,680 sq.ft.

$775,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.68%

Airbnb Rental Income: $null

Traditional Rental Income: $2821

Airbnb ROI: N/A

Traditional ROI: 1.68%

8842 HAWBOTTOM Road

MIDDLETOWN, MD

3 beds | 4 baths | 3,477 sq.ft.

$2,200,000

Airbnb cash on cash: -0.99%

Traditional cash on cash: -0.12%

Airbnb Rental Income: $2183

Traditional Rental Income: $3406

Airbnb ROI: -0.99%

Traditional ROI: -0.12%

417 W MAIN Street

MIDDLETOWN, MD

3 beds | 1 baths | 1,392 sq.ft.

$299,990

Airbnb cash on cash: 3.23%

Traditional cash on cash: 3.35%

Airbnb Rental Income: $2183

Traditional Rental Income: $1664

Airbnb ROI: 3.23%

Traditional ROI: 3.35%

3226 BIDLE Road

MIDDLETOWN, MD

3 beds | 3 baths | 1,820 sq.ft.

$649,000

Airbnb cash on cash: 0.62%

Traditional cash on cash: 3.06%

Airbnb Rental Income: $2183

Traditional Rental Income: $3108

Airbnb ROI: 0.62%

Traditional ROI: 3.06%

25 CHESTER Court

MIDDLETOWN, MD

3 beds | 4 baths | N/A

$449,900

Airbnb cash on cash: 1.27%

Traditional cash on cash: 5.16%

Airbnb Rental Income: $2183

Traditional Rental Income: $3267

Airbnb ROI: 1.27%

Traditional ROI: 5.16%

1 KELLER LN

MIDDLETOWN, MD

3 beds | 3 baths | N/A

$574,900

Airbnb cash on cash: 0.83%

Traditional cash on cash: 2.58%

Airbnb Rental Income: $2183

Traditional Rental Income: $2567

Airbnb ROI: 0.83%