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
1670-1670 MONUMENT RD MIDDLETOWN, MD Country living at its finest! Perfect for hobby farm enthusiast or just someone who wants ...	5 beds \| 4 baths \| N/A	$765,900	Airbnb cash on cash: 2.28% Traditional cash on cash: 2% Airbnb Rental Income: $3772 Traditional Rental Income: $2758 Airbnb ROI: 2.28% Traditional ROI: 2%
6524 MORNINGSIDE CT MIDDLETOWN, MD OPEN HOUSE CANCELLED DUE TO GOING UNDER CONTRACT! Home Sweet Home in Middletown! If there ...	4 beds \| 4 baths \| N/A	$585,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.35% Airbnb Rental Income: $null Traditional Rental Income: $3537 Airbnb ROI: N/A Traditional ROI: 4.35%
15 WAGON SHED LN MIDDLETOWN, MD FRESH PAINT IN MANY AREAS. MOVE IN READY. Imagine cozy evenings by the gas fireplace in ...	4 beds \| 4 baths \| N/A	$799,990	Airbnb cash on cash: N/A Traditional cash on cash: 2.38% Airbnb Rental Income: $null Traditional Rental Income: $3409 Airbnb ROI: N/A Traditional ROI: 2.38%
27 WAGON SHED LN MIDDLETOWN, MD Incredible, impeccable, and spacious home on a large corner lot in Glenbrook offers four f...	5 beds \| 5 baths \| N/A	$900,000	Airbnb cash on cash: 1.47% Traditional cash on cash: 3.7% Airbnb Rental Income: $3772 Traditional Rental Income: $4824 Airbnb ROI: 1.47% Traditional ROI: 3.7%
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.	$2,300,000	Airbnb cash on cash: -0.22% Traditional cash on cash: -0.16% Airbnb Rental Income: $4158 Traditional Rental Income: $3406 Airbnb ROI: -0.22% Traditional ROI: -0.16%
404 STONE SPRINGS LANE MIDDLETOWN, MD Back on the market with a price reduction! The buyer got cold feet! Make this beautiful Gl...	4 beds \| 4 baths \| 2,640 sq.ft.	$425,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.23% Airbnb Rental Income: $null Traditional Rental Income: $3106 Airbnb ROI: N/A Traditional ROI: 5.23%
4300 ZIRCON ROAD MIDDLETOWN, MD Stunning 4-bed, 3.5-bath single-family home ideally located just minutes from Downtown Mid...	4 beds \| 4 baths \| 2,912 sq.ft.	$629,999	Airbnb cash on cash: N/A Traditional cash on cash: 4.16% Airbnb Rental Income: $null Traditional Rental Income: $3616 Airbnb ROI: N/A Traditional ROI: 4.16%
7103 UNAKITE COURT MIDDLETOWN, MD This property qualifies for USDA 100% financing!! Welcome to 7103 Unakite Ct a spacious an...	3 beds \| 3 baths \| 2,184 sq.ft.	$485,000	Airbnb cash on cash: 5.44% Traditional cash on cash: 4.89% Airbnb Rental Income: $4158 Traditional Rental Income: $3027 Airbnb ROI: 5.44% Traditional ROI: 4.89%
20 WASH HOUSE CIRCLE MIDDLETOWN, MD * New Roof (2025) * 3 Fully Finished Levels * Walk Out Lower Level * 2 Decks * Backs To Go...	5 beds \| 4 baths \| 2,640 sq.ft.	$425,000	Airbnb cash on cash: 4.82% Traditional cash on cash: 5.03% Airbnb Rental Income: $3772 Traditional Rental Income: $3037 Airbnb ROI: 4.82% Traditional ROI: 5.03%
9 CAROLINE DRIVE MIDDLETOWN, MD Immaculately maintained and tastefully updated, nearly 3,000 sq. ft. four bedroom, two ful...	4 beds \| 3 baths \| 2,616 sq.ft.	$624,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.86% Airbnb Rental Income: $null Traditional Rental Income: $2806 Airbnb ROI: N/A Traditional ROI: 2.86%
6408 ZITTLESTOWN ROAD MIDDLETOWN, MD Don't miss this stunner! Make this bright and open chalet style log home nestled on 5 acre...	3 beds \| 3 baths \| 2,186 sq.ft.	$770,000	Airbnb cash on cash: 2.84% Traditional cash on cash: 2.07% Airbnb Rental Income: $4158 Traditional Rental Income: $2727 Airbnb ROI: 2.84% Traditional ROI: 2.07%
107 MINA DRIVE MIDDLETOWN, MD Don't miss out on the opportunity to own one of the largest lots in the community. With a ...	4 beds \| 4 baths \| 3,680 sq.ft.	$799,900	Airbnb cash on cash: N/A Traditional cash on cash: 1.7% Airbnb Rental Income: $null Traditional Rental Income: $2821 Airbnb ROI: N/A Traditional ROI: 1.7%
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: 9.06% Traditional cash on cash: 3.35% Airbnb Rental Income: $4158 Traditional Rental Income: $1664 Airbnb ROI: 9.06% Traditional ROI: 3.35%
3-N POINTE TER MIDDLETOWN, MD A MUST SEE! Easy to show! Welcome to 3 North Pointe Terrace, a stunning home located in t...	5 beds \| 4 baths \| N/A	$669,000	Airbnb cash on cash: 2.54% Traditional cash on cash: 3.11% Airbnb Rental Income: $3772 Traditional Rental Income: $3308 Airbnb ROI: 2.54% Traditional ROI: 3.11%
4 TILE SILO CT MIDDLETOWN, MD Stunning 5-Bedroom Home with Golf Course Views and Luxury Upgrades! Welcome to this beaut...	5 beds \| 4 baths \| N/A	$859,900	Airbnb cash on cash: 1.61% Traditional cash on cash: 2.5% Airbnb Rental Income: $3772 Traditional Rental Income: $3665 Airbnb ROI: 1.61% Traditional ROI: 2.5%

Real Estate investment in Middletown, MD

There are 15 properties for sale in the city of Middletown . The median list price in Middletown is $669,000 and the average price per square foot is $254. In September 2025, the average monthly cash on cash return in Middletown is 3.00%. The average monthly rental income in Middletown is $3,106.

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

There are 15 investment properties available for sale in Middletown.

In 2025, 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 $3,772.

Your search for investment property begins and ends here

Investment Property for Sale in Middletown, MD

1670-1670 MONUMENT RD

MIDDLETOWN, MD

5 beds | 4 baths | N/A

$765,900

Airbnb cash on cash: 2.28%

Traditional cash on cash: 2%

Airbnb Rental Income: $3772

Traditional Rental Income: $2758

Airbnb ROI: 2.28%

Traditional ROI: 2%

6524 MORNINGSIDE CT

MIDDLETOWN, MD

4 beds | 4 baths | N/A

$585,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.35%

Airbnb Rental Income: $null

Traditional Rental Income: $3537

Airbnb ROI: N/A

Traditional ROI: 4.35%

15 WAGON SHED LN

MIDDLETOWN, MD

4 beds | 4 baths | N/A

$799,990

Airbnb cash on cash: N/A

Traditional cash on cash: 2.38%

Airbnb Rental Income: $null

Traditional Rental Income: $3409

Airbnb ROI: N/A

Traditional ROI: 2.38%

27 WAGON SHED LN

MIDDLETOWN, MD

5 beds | 5 baths | N/A

$900,000

Airbnb cash on cash: 1.47%

Traditional cash on cash: 3.7%

Airbnb Rental Income: $3772

Traditional Rental Income: $4824

Airbnb ROI: 1.47%

Traditional ROI: 3.7%

8842 HAWBOTTOM ROAD

MIDDLETOWN, MD

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

$2,300,000

Airbnb cash on cash: -0.22%

Traditional cash on cash: -0.16%

Airbnb Rental Income: $4158

Traditional Rental Income: $3406

Airbnb ROI: -0.22%

Traditional ROI: -0.16%

404 STONE SPRINGS LANE

MIDDLETOWN, MD

4 beds | 4 baths | 2,640 sq.ft.

$425,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.23%

Airbnb Rental Income: $null

Traditional Rental Income: $3106

Airbnb ROI: N/A

Traditional ROI: 5.23%

4300 ZIRCON ROAD

MIDDLETOWN, MD

4 beds | 4 baths | 2,912 sq.ft.

$629,999

Airbnb cash on cash: N/A

Traditional cash on cash: 4.16%

Airbnb Rental Income: $null

Traditional Rental Income: $3616

Airbnb ROI: N/A

Traditional ROI: 4.16%

7103 UNAKITE COURT

MIDDLETOWN, MD

3 beds | 3 baths | 2,184 sq.ft.

$485,000

Airbnb cash on cash: 5.44%

Traditional cash on cash: 4.89%

Airbnb Rental Income: $4158

Traditional Rental Income: $3027

Airbnb ROI: 5.44%