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
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: N/A Traditional cash on cash: 3.39% Airbnb Rental Income: $null Traditional Rental Income: $6805 Airbnb ROI: N/A Traditional ROI: 3.39%
2730 MARKER RD MIDDLETOWN, MD Love history? Love farming? Love Middletown Valley? This trifecta is for YOU! Once a b...	5 beds \| 2 baths \| N/A	$1,395,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.12% Airbnb Rental Income: $null Traditional Rental Income: $2593 Airbnb ROI: N/A Traditional ROI: 0.12%
3213 OLD NATIONAL Pike MIDDLETOWN, MD Price Improvement! This iconic 1937 Brick Tudor Revival residence and adjacent additional ...	3 beds \| 3 baths \| 1,782 sq.ft.	$699,900	Airbnb cash on cash: -0.98% Traditional cash on cash: 3.02% Airbnb Rental Income: $813 Traditional Rental Income: $3096 Airbnb ROI: -0.98% Traditional ROI: 3.02%
7 DERR Lane MIDDLETOWN, MD NEW PRICE! OPEN HOUSE SUNDAY 5/17 - 10:00-12:00! Welcome to 7 Derr Lane in the sought-afte...	3 beds \| 3 baths \| 2,208 sq.ft.	$650,000	Airbnb cash on cash: -1.54% Traditional cash on cash: 2.47% Airbnb Rental Income: $813 Traditional Rental Income: $2921 Airbnb ROI: -1.54% Traditional ROI: 2.47%
MOUNTAIN CHURCH Road MIDDLETOWN, MD HOME TO BE BUILT. Nestled on a beautiful, wooded 2.25-acre lot, this to-be-built home by G...	3 beds \| 3 baths \| 3,000 sq.ft.	$924,500	Airbnb cash on cash: -0.7% Traditional cash on cash: 2.13% Airbnb Rental Income: $813 Traditional Rental Income: $2925 Airbnb ROI: -0.7% Traditional ROI: 2.13%
307 WASHINGTON ST MIDDLETOWN, MD Now on market! This picturesque single-family home sits in the heart of beautiful histori...	5 beds \| 4 baths \| N/A	$645,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.82% Airbnb Rental Income: $null Traditional Rental Income: $2994 Airbnb ROI: N/A Traditional ROI: 2.82%
110 STONE SPRINGS LN MIDDLETOWN, MD Beautifully updated townhome in sought after Glenbrook community backing to the Richland G...	4 beds \| 4 baths \| N/A	$435,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.74% Airbnb Rental Income: $null Traditional Rental Income: $2497 Airbnb ROI: N/A Traditional ROI: 3.74%
4432 VALLEY VIEW Road MIDDLETOWN, MD Don't miss out on this very well maintained all-brick rancher situated on a level, half ac...	3 beds \| 3 baths \| 1,232 sq.ft.	$479,900	Airbnb cash on cash: -0.82% Traditional cash on cash: 3.85% Airbnb Rental Income: $813 Traditional Rental Income: $2588 Airbnb ROI: -0.82% Traditional ROI: 3.85%
2616 QUEBEC SCHOOL RD MIDDLETOWN, MD OFFER Deadline Monday 5/18 at 3pm. Last Open House Sunday 1-3 pm. Welcome to 2616 Queb...	5 beds \| 5 baths \| N/A	$859,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.36% Airbnb Rental Income: $null Traditional Rental Income: $5010 Airbnb ROI: N/A Traditional ROI: 4.36%
124 E MAIN Street MIDDLETOWN, MD Charming Victorian Home offers the perfect blend of historic character and modern upgrades...	3 beds \| 2 baths \| 2,474 sq.ft.	$599,900	Airbnb cash on cash: -1.41% Traditional cash on cash: 2.45% Airbnb Rental Income: $813 Traditional Rental Income: $2651 Airbnb ROI: -1.41% Traditional ROI: 2.45%
9237 FROSTOWN Road MIDDLETOWN, MD Experience the flow of space and harmony a private 5-acre sanctuary where mid-century soul...	4 beds \| 5 baths \| 6,578 sq.ft.	$2,500,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.84% Airbnb Rental Income: $null Traditional Rental Income: $5321 Airbnb ROI: N/A Traditional ROI: 0.84%
11 CRONE Lane MIDDLETOWN, MD Welcome to Foxfields at Middletown, one of the area's most sought-after 55+ communities. T...	3 beds \| 4 baths \| 2,649 sq.ft.	$625,000	Airbnb cash on cash: -1.5% Traditional cash on cash: 3.13% Airbnb Rental Income: $813 Traditional Rental Income: $3189 Airbnb ROI: -1.5% Traditional ROI: 3.13%
6419 ZITTLESTOWN RD MIDDLETOWN, MD NO HOA and NO CITY TAXES! Charming cottage-style home nestled on a scenic .38-acre lot, lo...	2 beds \| 1 baths \| N/A	$235,000	Airbnb cash on cash: 0.6% Traditional cash on cash: 4.34% Airbnb Rental Income: $939 Traditional Rental Income: $1425 Airbnb ROI: 0.6% Traditional ROI: 4.34%

Real Estate investment in Middletown, MD

There are 17 properties for sale in the city of Middletown . The median list price in Middletown is $410,000 and the average price per square foot is $225. In May 2026, the average monthly cash on cash return in Middletown is 4.00%. The average monthly rental income in Middletown is $2,651.

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

There are 17 investment properties available for sale in Middletown.

In 2026, 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 $2,651.

Your search for investment property begins and ends here

Investment Property for Sale in Middletown, MD

4209 MARYLAND CT

MIDDLETOWN, MD

4 beds | 6 baths | N/A

$1,400,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.39%

Airbnb Rental Income: $null

Traditional Rental Income: $6805

Airbnb ROI: N/A

Traditional ROI: 3.39%

2730 MARKER RD

MIDDLETOWN, MD

5 beds | 2 baths | N/A

$1,395,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.12%

Airbnb Rental Income: $null

Traditional Rental Income: $2593

Airbnb ROI: N/A

Traditional ROI: 0.12%

3213 OLD NATIONAL Pike

MIDDLETOWN, MD

3 beds | 3 baths | 1,782 sq.ft.

$699,900

Airbnb cash on cash: -0.98%

Traditional cash on cash: 3.02%

Airbnb Rental Income: $813

Traditional Rental Income: $3096

Airbnb ROI: -0.98%

Traditional ROI: 3.02%

7 DERR Lane

MIDDLETOWN, MD

3 beds | 3 baths | 2,208 sq.ft.

$650,000

Airbnb cash on cash: -1.54%

Traditional cash on cash: 2.47%

Airbnb Rental Income: $813

Traditional Rental Income: $2921

Airbnb ROI: -1.54%

Traditional ROI: 2.47%

MOUNTAIN CHURCH Road

MIDDLETOWN, MD

3 beds | 3 baths | 3,000 sq.ft.

$924,500

Airbnb cash on cash: -0.7%

Traditional cash on cash: 2.13%

Airbnb Rental Income: $813

Traditional Rental Income: $2925

Airbnb ROI: -0.7%

Traditional ROI: 2.13%

307 WASHINGTON ST

MIDDLETOWN, MD

5 beds | 4 baths | N/A

$645,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.82%

Airbnb Rental Income: $null

Traditional Rental Income: $2994

Airbnb ROI: N/A

Traditional ROI: 2.82%

110 STONE SPRINGS LN

MIDDLETOWN, MD

4 beds | 4 baths | N/A

$435,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.74%

Airbnb Rental Income: $null

Traditional Rental Income: $2497

Airbnb ROI: N/A

Traditional ROI: 3.74%

4432 VALLEY VIEW Road

MIDDLETOWN, MD

3 beds | 3 baths | 1,232 sq.ft.

$479,900

Airbnb cash on cash: -0.82%

Traditional cash on cash: 3.85%

Airbnb Rental Income: $813

Traditional Rental Income: $2588

Airbnb ROI: -0.82%