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
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.	$749,000	Airbnb cash on cash: 1.14% Traditional cash on cash: 2.16% Airbnb Rental Income: $2649 Traditional Rental Income: $2727 Airbnb ROI: 1.14% Traditional ROI: 2.16%
7103 UNAKITE Court MIDDLETOWN, MD This property qualifies for USDA 100% financing!! Welcome to 7103 Unakite Ct - a spacious ...	3 beds \| 3 baths \| 2,184 sq.ft.	$470,000	Airbnb cash on cash: 2.78% Traditional cash on cash: 5.07% Airbnb Rental Income: $2649 Traditional Rental Income: $3027 Airbnb ROI: 2.78% Traditional ROI: 5.07%
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: -0.8% Traditional cash on cash: -0.12% Airbnb Rental Income: $2649 Traditional Rental Income: $3406 Airbnb ROI: -0.8% 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: 4.61% Traditional cash on cash: 3.35% Airbnb Rental Income: $2649 Traditional Rental Income: $1664 Airbnb ROI: 4.61% Traditional ROI: 3.35%
7025 WILLOW TREE Drive S MIDDLETOWN, MD Beautiful Colonial on a great corner lot in desirable Middletown! This house features 4 be...	4 beds \| 3 baths \| 2,802 sq.ft.	$599,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.8% Airbnb Rental Income: $null Traditional Rental Income: $3270 Airbnb ROI: N/A Traditional ROI: 3.8%
4509 VALLEY VIEW Road MIDDLETOWN, MD Middletown-3 Bedroom, 2 Bath all Brick Rancher with oversized 2 Car Garage. Newer HVAC Uni...	3 beds \| 2 baths \| 1,176 sq.ft.	$444,900	Airbnb cash on cash: 2.95% Traditional cash on cash: 3.24% Airbnb Rental Income: $2649 Traditional Rental Income: $2141 Airbnb ROI: 2.95% Traditional ROI: 3.24%
114 IVY HILL Drive MIDDLETOWN, MD Move-In Ready 5-Bedroom, 3.5-Bath Home in Scenic Middletown Valley Welcome to the highly s...	5 beds \| 4 baths \| 2,540 sq.ft.	$629,900	Airbnb cash on cash: 0.76% Traditional cash on cash: 3.84% Airbnb Rental Income: $2240 Traditional Rental Income: $3490 Airbnb ROI: 0.76% Traditional ROI: 3.84%
7291 BEECHTREE LN MIDDLETOWN, MD Tucked away in a peaceful cul-de-sac just off Old National Pike, this charming home sits g...	4 beds \| 3 baths \| N/A	$525,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.06% Airbnb Rental Income: $null Traditional Rental Income: $2431 Airbnb ROI: N/A 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	$475,000	Airbnb cash on cash: 2.03% Traditional cash on cash: 4.84% Airbnb Rental Income: $2649 Traditional Rental Income: $3267 Airbnb ROI: 2.03% Traditional ROI: 4.84%
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: 1.55% Traditional cash on cash: 2.58% Airbnb Rental Income: $2649 Traditional Rental Income: $2567 Airbnb ROI: 1.55% Traditional ROI: 2.58%
110 S JEFFERSON ST MIDDLETOWN, MD OPEN HOUSE CANCELLED - Home is under contract! This beautifully renovated 1947 bungalow bl...	3 beds \| 2 baths \| N/A	$435,000	Airbnb cash on cash: 3.11% Traditional cash on cash: 3.44% Airbnb Rental Income: $2649 Traditional Rental Income: $2151 Airbnb ROI: 3.11% Traditional ROI: 3.44%
106 STONE SPRINGS Lane MIDDLETOWN, MD OPEN HOUSE Saturday (10/18) 11am - 1pm - AN ABSOLUTE MUST SEE! Experience luxury, comfort,...	4 beds \| 4 baths \| 2,727 sq.ft.	$425,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.01% Airbnb Rental Income: $null Traditional Rental Income: $2912 Airbnb ROI: N/A Traditional ROI: 5.01%
4 BROOKLODGE LN MIDDLETOWN, MD This gracious home was designed to promote relaxation and effortless entertaining and was ...	4 beds \| 5 baths \| N/A	$1,200,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.26% Airbnb Rental Income: $null Traditional Rental Income: $4663 Airbnb ROI: N/A Traditional ROI: 2.26%

Real Estate investment in Middletown, MD

There are 13 properties for sale in the city of Middletown . The median list price in Middletown is $525,000 and the average price per square foot is $227. In October 2025, the average monthly cash on cash return in Middletown is 3.00%. The average monthly rental income in Middletown is $2,912.

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 $2,912.

Your search for investment property begins and ends here

Investment Property for Sale in Middletown, MD

6408 ZITTLESTOWN Road

MIDDLETOWN, MD

3 beds | 3 baths | 2,186 sq.ft.

$749,000

Airbnb cash on cash: 1.14%

Traditional cash on cash: 2.16%

Airbnb Rental Income: $2649

Traditional Rental Income: $2727

Airbnb ROI: 1.14%

Traditional ROI: 2.16%

7103 UNAKITE Court

MIDDLETOWN, MD

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

$470,000

Airbnb cash on cash: 2.78%

Traditional cash on cash: 5.07%

Airbnb Rental Income: $2649

Traditional Rental Income: $3027

Airbnb ROI: 2.78%

Traditional ROI: 5.07%

8842 HAWBOTTOM Road

MIDDLETOWN, MD

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

$2,200,000

Airbnb cash on cash: -0.8%

Traditional cash on cash: -0.12%

Airbnb Rental Income: $2649

Traditional Rental Income: $3406

Airbnb ROI: -0.8%

Traditional ROI: -0.12%

417 W MAIN Street

MIDDLETOWN, MD

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

$299,990

Airbnb cash on cash: 4.61%

Traditional cash on cash: 3.35%

Airbnb Rental Income: $2649

Traditional Rental Income: $1664

Airbnb ROI: 4.61%

Traditional ROI: 3.35%

7025 WILLOW TREE Drive S

MIDDLETOWN, MD

4 beds | 3 baths | 2,802 sq.ft.

$599,900

Airbnb cash on cash: N/A

Traditional cash on cash: 3.8%

Airbnb Rental Income: $null

Traditional Rental Income: $3270

Airbnb ROI: N/A

Traditional ROI: 3.8%

4509 VALLEY VIEW Road

MIDDLETOWN, MD

3 beds | 2 baths | 1,176 sq.ft.

$444,900

Airbnb cash on cash: 2.95%

Traditional cash on cash: 3.24%

Airbnb Rental Income: $2649

Traditional Rental Income: $2141

Airbnb ROI: 2.95%

Traditional ROI: 3.24%

114 IVY HILL Drive

MIDDLETOWN, MD

5 beds | 4 baths | 2,540 sq.ft.

$629,900

Airbnb cash on cash: 0.76%

Traditional cash on cash: 3.84%

Airbnb Rental Income: $2240

Traditional Rental Income: $3490

Airbnb ROI: 0.76%

Traditional ROI: 3.84%

7291 BEECHTREE LN

MIDDLETOWN, MD

4 beds | 3 baths | N/A

$525,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.06%

Airbnb Rental Income: $null

Traditional Rental Income: $2431

Airbnb ROI: N/A