Real Estate Investment Properties for Sale in Middletown, DE

Looking for investment property in Middletown, DE with high ROI ?

Explore a variety of short-term homes & houses in Middletown, DE. Invest wisely with VRBO & Middletown, DE 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, DE

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
610 LOUIS LN Middletown, DE Discover this beautifully maintained end unit townhome in sought-after Middletown Village....	3 beds \| 2 baths \| N/A	$299,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.22% Airbnb Rental Income: $null Traditional Rental Income: $2140 Airbnb ROI: N/A Traditional ROI: 5.22%
2804 MONDRIAN LANE Middletown, DE Major Price Drop Welcome to 2804 Mondrian Lane! The moment you step inside, you're welco...	3 beds \| 3 baths \| 1,900 sq.ft.	$449,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.61% Airbnb Rental Income: $null Traditional Rental Income: $2453 Airbnb ROI: N/A Traditional ROI: 3.61%
129 AYSHIRE Drive unit: Coronado #Coronado Middletown, DE Welcome to the Highlands at Back Creek- a small community of only 42 lots. Most lots back ...	4 beds \| 3 baths \| 3,503 sq.ft.	$799,990	Airbnb cash on cash: N/A Traditional cash on cash: 2.28% Airbnb Rental Income: $null Traditional Rental Income: $3342 Airbnb ROI: N/A Traditional ROI: 2.28%
129 AYSHIRE Drive unit: Somerset Floorplan #Somerset Floorplan Middletown, DE Welcome to Highlands at Back Creek- a small community of only 42 lots. Most lots back to o...	4 beds \| 3 baths \| 3,116 sq.ft.	$769,990	Airbnb cash on cash: N/A Traditional cash on cash: 2.45% Airbnb Rental Income: $null Traditional Rental Income: $3367 Airbnb ROI: N/A Traditional ROI: 2.45%
162 LIBORIO DR Middletown, DE Beautifully maintained townhouse in desirable Middletown Village. This home features a spa...	3 beds \| 2 baths \| N/A	$293,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.09% Airbnb Rental Income: $null Traditional Rental Income: $2045 Airbnb ROI: N/A Traditional ROI: 5.09%
129 AYSHIRE Drive unit: Lexington #Lexington Middletown, DE 1st FLOOR OWNER'S SUITE!!!! Welcome to Highlands at Back Creek- a small community of only ...	4 beds \| 3 baths \| 3,400 sq.ft.	$809,990	Airbnb cash on cash: N/A Traditional cash on cash: 2.24% Airbnb Rental Income: $null Traditional Rental Income: $3342 Airbnb ROI: N/A Traditional ROI: 2.24%
129 AYSHIRE Drive unit: Hancock Grand #Hancock Grand Middletown, DE Welcome to the Highlands at Back Creek- a small community of only 42 lots. Most lots back ...	4 beds \| 3 baths \| 3,260 sq.ft.	$758,990	Airbnb cash on cash: N/A Traditional cash on cash: 2.46% Airbnb Rental Income: $null Traditional Rental Income: $3342 Airbnb ROI: N/A Traditional ROI: 2.46%
602 BARRIE RD Middletown, DE When you think ""turnkey,""Ãï¿½ elevated comfort living this is the one! Welcome to thi...	3 beds \| 4 baths \| N/A	$425,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.19% Airbnb Rental Income: $null Traditional Rental Income: $2493 Airbnb ROI: N/A Traditional ROI: 4.19%
133 PINE VALLEY DRIVE Middletown, DE Situated on a large corner lot, this home has been lovingly maintained by the original own...	4 beds \| 3 baths \| 2,325 sq.ft.	$510,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.56% Airbnb Rental Income: $null Traditional Rental Income: $3142 Airbnb ROI: N/A Traditional ROI: 4.56%
102 SPRINGMILL DR Middletown, DE A Rare Opportunity Awaits! Private Tree-Lined Lot & Rare Basement in Springmill! Discover ...	2 beds \| 2 baths \| N/A	$467,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.16% Airbnb Rental Income: $null Traditional Rental Income: $2061 Airbnb ROI: N/A Traditional ROI: 3.16%
204 BALDY LN unit: Annandale #Annandale Middletown, DE Welcome to the 55+ community of Traditions at Whitehall - Annandale Carriage Town Home. Th...	2 beds \| 3 baths \| 1,794 sq.ft.	$425,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.36% Airbnb Rental Income: $null Traditional Rental Income: $2452 Airbnb ROI: N/A Traditional ROI: 4.36%
204 BALDY LN unit: Alrich #Alrich Middletown, DE Welcome to the 55+ community of Traditions at Whitehall - Alrich Carriage Town Home. This ...	2 beds \| 3 baths \| 1,794 sq.ft.	$425,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.59% Airbnb Rental Income: $null Traditional Rental Income: $2543 Airbnb ROI: N/A Traditional ROI: 4.59%
57 W SARAZEN DR Middletown, DE Discover a fantastic opportunity to own a rarely available end unit townhome featuring 4 b...	4 beds \| 3 baths \| N/A	$399,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.26% Airbnb Rental Income: $null Traditional Rental Income: $2093 Airbnb ROI: N/A Traditional ROI: 3.26%
617 Mccracken Dr Middletown, DE About to break ground on this beautiful Houston spec home. Anticipated delivery is around ...	5 beds \| 3 baths \| 3,560 sq.ft.	$769,999	Airbnb cash on cash: N/A Traditional cash on cash: 5.4% Airbnb Rental Income: $null Traditional Rental Income: $4855 Airbnb ROI: N/A Traditional ROI: 5.4%
104 Cantwell Dr Middletown, DE 104 Cantwell Dr, Middletown, DE 19709 \| Single Family Residential	5 beds \| 3 baths \| 4,350 sq.ft.	$669,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.63% Airbnb Rental Income: $null Traditional Rental Income: $2747 Airbnb ROI: N/A Traditional ROI: 2.63%

Real Estate investment in Middletown, DE

There are 16 properties for sale in the city of Middletown . The median list price in Middletown is $607,495 and the average price per square foot is $214. In March 2026, the average monthly cash on cash return in Middletown is 3.00%. The average monthly rental income in Middletown is $2,547.

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

There are 16 investment properties available for sale in Middletown.

In 2026, 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 $N/A.

Your search for investment property begins and ends here

Investment Property for Sale in Middletown, DE

610 LOUIS LN

Middletown, DE

3 beds | 2 baths | N/A

$299,900

Airbnb cash on cash: N/A

Traditional cash on cash: 5.22%

Airbnb Rental Income: $null

Traditional Rental Income: $2140

Airbnb ROI: N/A

Traditional ROI: 5.22%

2804 MONDRIAN LANE

Middletown, DE

3 beds | 3 baths | 1,900 sq.ft.

$449,900

Airbnb cash on cash: N/A

Traditional cash on cash: 3.61%

Airbnb Rental Income: $null

Traditional Rental Income: $2453

Airbnb ROI: N/A

Traditional ROI: 3.61%

129 AYSHIRE Drive unit: Coronado #Coronado

Middletown, DE

4 beds | 3 baths | 3,503 sq.ft.

$799,990

Airbnb cash on cash: N/A

Traditional cash on cash: 2.28%

Airbnb Rental Income: $null

Traditional Rental Income: $3342

Airbnb ROI: N/A

Traditional ROI: 2.28%

129 AYSHIRE Drive unit: Somerset Floorplan #Somerset Floorplan

Middletown, DE

4 beds | 3 baths | 3,116 sq.ft.

$769,990

Airbnb cash on cash: N/A

Traditional cash on cash: 2.45%

Airbnb Rental Income: $null

Traditional Rental Income: $3367

Airbnb ROI: N/A

Traditional ROI: 2.45%

162 LIBORIO DR

Middletown, DE

3 beds | 2 baths | N/A

$293,900

Airbnb cash on cash: N/A

Traditional cash on cash: 5.09%

Airbnb Rental Income: $null

Traditional Rental Income: $2045

Airbnb ROI: N/A

Traditional ROI: 5.09%

129 AYSHIRE Drive unit: Lexington #Lexington

Middletown, DE

4 beds | 3 baths | 3,400 sq.ft.

$809,990

Airbnb cash on cash: N/A

Traditional cash on cash: 2.24%

Airbnb Rental Income: $null

Traditional Rental Income: $3342

Airbnb ROI: N/A

Traditional ROI: 2.24%

129 AYSHIRE Drive unit: Hancock Grand #Hancock Grand

Middletown, DE

4 beds | 3 baths | 3,260 sq.ft.

$758,990

Airbnb cash on cash: N/A

Traditional cash on cash: 2.46%

Airbnb Rental Income: $null

Traditional Rental Income: $3342

Airbnb ROI: N/A

Traditional ROI: 2.46%

602 BARRIE RD

Middletown, DE

3 beds | 4 baths | N/A

$425,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.19%

Airbnb Rental Income: $null

Traditional Rental Income: $2493

Airbnb ROI: N/A