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
945 Lansdowne Rd Middletown, DE Welcome home to this well cared for 3BR 2BA town home in the well desired Willow Grove Mil...	3 beds \| 2 baths \| 1,650 sq.ft.	$269,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.86% Airbnb Rental Income: $null Traditional Rental Income: $2014 Airbnb ROI: N/A Traditional ROI: 5.86%
329 PRICE Drive Middletown, DE Welcome to 329 Price Drive, located in the prestigious Estates at Cedar Lane within the hi...	4 beds \| 4 baths \| 3,856 sq.ft.	$925,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.37% Airbnb Rental Income: $null Traditional Rental Income: $4667 Airbnb ROI: N/A Traditional ROI: 3.37%
433 AFTON DR Middletown, DE Nestled in the charming Canal View community, this exquisite end-of-row townhouse offers a...	3 beds \| 4 baths \| N/A	$460,100	Airbnb cash on cash: N/A Traditional cash on cash: 5.67% Airbnb Rental Income: $null Traditional Rental Income: $3331 Airbnb ROI: N/A Traditional ROI: 5.67%
417 WILMORE Drive Middletown, DE Welcome home to this beautifully maintained move-in ready 3-bedroom, 2.1-bath home in the ...	3 beds \| 3 baths \| 1,650 sq.ft.	$375,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.07% Airbnb Rental Income: $null Traditional Rental Income: $2196 Airbnb ROI: N/A Traditional ROI: 4.07%
1300 CARRICK Court #Massey Elite Model Middletown, DE BASE PRICE LISTING - MODEL HOME IS NOT FOR SALE. Welcome to a stylish and spacious 3-story...	3 beds \| 3 baths \| 2,001 sq.ft.	$416,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.62% Airbnb Rental Income: $null Traditional Rental Income: $2615 Airbnb ROI: N/A Traditional ROI: 4.62%
530 WHEELMEN Street #1 Edmonston Middletown, DE Edmonston -TO BE BUILT. Come tour our decorated model during business hours. This 4 bedroo...	4 beds \| 3 baths \| 2,716 sq.ft.	$591,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.99% Airbnb Rental Income: $null Traditional Rental Income: $3234 Airbnb ROI: N/A Traditional ROI: 3.99%
20 W KILTS Lane Middletown, DE Enter at the grand 2-sty Foyer w/ HW fls, neutral decor, a large arched window over the do...	4 beds \| 4 baths \| 3,425 sq.ft.	$597,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.92% Airbnb Rental Income: $null Traditional Rental Income: $4580 Airbnb ROI: N/A Traditional ROI: 5.92%
113 CRAWFORD ST Middletown, DE Welcome to 113 Crawford Street. Located in the heart of Middletown, Delaware. Enjoy close...	3 beds \| 2 baths \| N/A	$365,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.12% Airbnb Rental Income: $null Traditional Rental Income: $2138 Airbnb ROI: N/A Traditional ROI: 4.12%
32 W MINGLEWOOD DRIVE Middletown, DE Located in the desirable Cricklewood community in Middletown Delaware, this well-maintaine...	3 beds \| 3 baths \| 2,200 sq.ft.	$525,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.43% Airbnb Rental Income: $null Traditional Rental Income: $2750 Airbnb ROI: N/A Traditional ROI: 3.43%
3 REDDING CIR Middletown, DE OFFER DEADLINE: TUESDAY 3/24/2026 @ 2PM EST. Priced to sell! Located in the highly desirab...	3 beds \| 1 baths \| N/A	$280,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.8% Airbnb Rental Income: $null Traditional Rental Income: $1653 Airbnb ROI: N/A Traditional ROI: 3.8%
204 BALDY Lane #Cottonwood Middletown, DE Welcome to the Cottonwood Model, TO BE BUILT, in the highly sought-after 55+ community of ...	3 beds \| 2 baths \| 2,477 sq.ft.	$614,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.62% Airbnb Rental Income: $null Traditional Rental Income: $2797 Airbnb ROI: N/A Traditional ROI: 2.62%
204 BALDY Lane #Chelsea Middletown, DE Introducing the CHELSEA Model, to be built in the highly desirable 55+ community of Tradit...	3 beds \| 2 baths \| 2,296 sq.ft.	$599,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.61% Airbnb Rental Income: $null Traditional Rental Income: $2722 Airbnb ROI: N/A Traditional ROI: 2.61%
204 BALDY Lane #Belville Middletown, DE Welcome to the Belville Model in the 55+community of Traditions at Whitehall. TO BE BUILT....	2 beds \| 2 baths \| 2,059 sq.ft.	$521,500	Airbnb cash on cash: -1.31% Traditional cash on cash: 2.94% Airbnb Rental Income: $910 Traditional Rental Income: $2643 Airbnb ROI: -1.31% Traditional ROI: 2.94%
120 BURLINA BLVD #Bloomfield Model Middletown, DE Welcome to the popular Bloomfield Model in the 55+ community of Traditions at Whitehall. T...	2 beds \| 2 baths \| 2,053 sq.ft.	$527,000	Airbnb cash on cash: -1.31% Traditional cash on cash: 2.9% Airbnb Rental Income: $910 Traditional Rental Income: $2643 Airbnb ROI: -1.31% Traditional ROI: 2.9%
204 BALDY Lane #Cayot Middletown, DE Welcome to the Cayot Model, in the desirable 55+ community of Traditions at Whitehall. Thi...	3 beds \| 2 baths \| 2,004 sq.ft.	$579,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.63% Airbnb Rental Income: $null Traditional Rental Income: $2687 Airbnb ROI: N/A Traditional ROI: 2.63%
204 BALDY Lane #Bristole Middletown, DE The Bristol Model is a thoughtfully designed 3-bedroom home that is TO BE BUILT in the hig...	3 beds \| 2 baths \| 2,441 sq.ft.	$548,500	Airbnb cash on cash: N/A Traditional cash on cash: 3.04% Airbnb Rental Income: $null Traditional Rental Income: $2793 Airbnb ROI: N/A Traditional ROI: 3.04%
129 AYSHIRE Drive #Plaza Middletown, DE Welcome to Highlands at Back Creek- a small community of only 42 lots. Most lots back to o...	4 beds \| 4 baths \| 4,569 sq.ft.	$884,990	Airbnb cash on cash: N/A Traditional cash on cash: 3.34% Airbnb Rental Income: $null Traditional Rental Income: $4468 Airbnb ROI: N/A Traditional ROI: 3.34%
129 AYSHIRE Drive #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 #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%
4 FARM Lane Middletown, DE More photos will be added soon Welcome to this stunning, fully remodeled gem in the hear...	4 beds \| 3 baths \| 1,900 sq.ft.	$465,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.36% Airbnb Rental Income: $null Traditional Rental Income: $2314 Airbnb ROI: N/A Traditional ROI: 3.36%
129 AYSHIRE Drive #Rittenhouse Middletown, DE Welcome to Highlands at Back Creek- a small community of only 42 lots. Most lots back to o...	4 beds \| 3 baths \| 4,569 sq.ft.	$839,990	Airbnb cash on cash: N/A Traditional cash on cash: 2.07% Airbnb Rental Income: $null Traditional Rental Income: $3294 Airbnb ROI: N/A Traditional ROI: 2.07%
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 #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%
398 GOODWICK Drive Middletown, DE Welcome to 398 Goodwick Dr in Middletown, DE - where space, style, and location come toget...	3 beds \| 4 baths \| 3,201 sq.ft.	$445,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.99% Airbnb Rental Income: $null Traditional Rental Income: $3522 Airbnb ROI: N/A Traditional ROI: 5.99%
1325 CARRICK COURT Middletown, DE Welcome to the desirable community of Ponds of Odessa, where you'll find this beautifully ...	3 beds \| 3 baths \| 2,575 sq.ft.	$469,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.02% Airbnb Rental Income: $null Traditional Rental Income: $2725 Airbnb ROI: N/A Traditional ROI: 4.02%
129 AYSHIRE Drive #Philadelphian Grand Middletown, DE Welcome to Highlands at Back Creek- a small community of only 42 lots. All homesites are a...	4 beds \| 4 baths \| 4,400 sq.ft.	$844,990	Airbnb cash on cash: N/A Traditional cash on cash: 3.54% Airbnb Rental Income: $null Traditional Rental Income: $4468 Airbnb ROI: N/A Traditional ROI: 3.54%
264 TRELLIS LANE Middletown, DE Fantastic Clean, Cozy Townhome in THE 55+ Community of the Middletown area, SPRING ARBOR. ...	2 beds \| 2 baths \| 1,800 sq.ft.	$425,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.51% Airbnb Rental Income: $null Traditional Rental Income: $1863 Airbnb ROI: N/A Traditional ROI: 2.51%
129 AYSHIRE Drive #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%
129 AYSHIRE Drive #Brandywine Grand Middletown, DE Welcome to Highlands at Back Creek, a small community of only 42 lots. Most lots back to o...	4 beds \| 3 baths \| 3,700 sq.ft.	$774,990	Airbnb cash on cash: N/A Traditional cash on cash: 2.32% Airbnb Rental Income: $null Traditional Rental Income: $3294 Airbnb ROI: N/A Traditional ROI: 2.32%
712 WALLASEY Drive Middletown, DE Spanning approximately 4,450 square feet, this impressive SENECA model 4 bedroom, 4.5-bath...	4 beds \| 5 baths \| 4,450 sq.ft.	$720,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.68% Airbnb Rental Income: $null Traditional Rental Income: $3984 Airbnb ROI: N/A Traditional ROI: 3.68%
409 GALWAY Court Middletown, DE Welcome to 409 Galway Court in the Popular Community of Hyetts Crossing. Conveniently loca...	3 beds \| 4 baths \| 1,700 sq.ft.	$450,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.61% Airbnb Rental Income: $null Traditional Rental Income: $2324 Airbnb ROI: N/A Traditional ROI: 3.61%
103 Westside Ln Middletown, DE Welcome to 103 Westside Lane in one of Middletown's most exclusive and coveted communities...	3 beds \| 1 baths \| 4,936 sq.ft.	$679,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.53% Airbnb Rental Income: $null Traditional Rental Income: $3448 Airbnb ROI: N/A Traditional ROI: 3.53%
1102 HIGHLAND Street #137 Ashton Middletown, DE IMMEDIATE AVAILABILITY! Welcome to the 55+ community of Traditions at Whitehall - Ashton C...	2 beds \| 3 baths \| 1,794 sq.ft.	$504,900	Airbnb cash on cash: -1.1% Traditional cash on cash: 3.86% Airbnb Rental Income: $910 Traditional Rental Income: $2915 Airbnb ROI: -1.1% Traditional ROI: 3.86%
460 REDERICK Lane #Massey Lot 61 Middletown, DE ** WORKFORCE HOUSING-BUYER MUST QUALIFY FOR THE NEW CASTLE COUNTY PROGRAM TO PURCHASE - MA...	3 beds \| 3 baths \| 2,300 sq.ft.	$384,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.5% Airbnb Rental Income: $null Traditional Rental Income: $2784 Airbnb ROI: N/A Traditional ROI: 5.5%
365 Andrew Ct Middletown, DE Welcome to 365 Andrew ct, this barely lived-in like new home offers all the benefits of ne...	3 beds \| 2 baths \| N/A	$477,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.26% Airbnb Rental Income: $null Traditional Rental Income: $3418 Airbnb ROI: N/A Traditional ROI: 6.26%
467 Hyetts Corner Rd Middletown, DE Vintage charm with modern amenities. This home built in the 1800s is on just about 1 acre....	N/A beds \| N/A baths \| 1,900 sq.ft.	$399,699	Airbnb cash on cash: N/A Traditional cash on cash: 5.6% Airbnb Rental Income: $null Traditional Rental Income: $2675 Airbnb ROI: N/A Traditional ROI: 5.6%

Real Estate investment in Middletown, DE

There are 289 properties for sale in the city of Middletown . The median list price in Middletown is $590,000 and the average price per square foot is $211. In April 2026, the average monthly cash on cash return in Middletown is 3.00%. The average monthly rental income in Middletown is $2,544.

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

There are 289 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 $2,544.

Your search for investment property begins and ends here

Investment Property for Sale in Middletown, DE

945 Lansdowne Rd

Middletown, DE

3 beds | 2 baths | 1,650 sq.ft.

$269,900

Airbnb cash on cash: N/A

Traditional cash on cash: 5.86%

Airbnb Rental Income: $null

Traditional Rental Income: $2014

Airbnb ROI: N/A

Traditional ROI: 5.86%

329 PRICE Drive

Middletown, DE

4 beds | 4 baths | 3,856 sq.ft.

$925,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.37%

Airbnb Rental Income: $null

Traditional Rental Income: $4667

Airbnb ROI: N/A

Traditional ROI: 3.37%

433 AFTON DR

Middletown, DE

3 beds | 4 baths | N/A

$460,100

Airbnb cash on cash: N/A

Traditional cash on cash: 5.67%

Airbnb Rental Income: $null

Traditional Rental Income: $3331

Airbnb ROI: N/A

Traditional ROI: 5.67%

417 WILMORE Drive

Middletown, DE

3 beds | 3 baths | 1,650 sq.ft.

$375,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.07%

Airbnb Rental Income: $null

Traditional Rental Income: $2196

Airbnb ROI: N/A

Traditional ROI: 4.07%

1300 CARRICK Court #Massey Elite Model

Middletown, DE

3 beds | 3 baths | 2,001 sq.ft.

$416,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.62%

Airbnb Rental Income: $null

Traditional Rental Income: $2615

Airbnb ROI: N/A

Traditional ROI: 4.62%

530 WHEELMEN Street #1 Edmonston

Middletown, DE

4 beds | 3 baths | 2,716 sq.ft.

$591,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.99%

Airbnb Rental Income: $null

Traditional Rental Income: $3234

Airbnb ROI: N/A

Traditional ROI: 3.99%

20 W KILTS Lane

Middletown, DE

4 beds | 4 baths | 3,425 sq.ft.

$597,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.92%

Airbnb Rental Income: $null

Traditional Rental Income: $4580

Airbnb ROI: N/A

Traditional ROI: 5.92%

113 CRAWFORD ST

Middletown, DE

3 beds | 2 baths | N/A

$365,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.12%

Airbnb Rental Income: $null

Traditional Rental Income: $2138

Airbnb ROI: N/A