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

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
1920 E ARISTOTLE AVE Middletown, DE Welcome to 1920 E Aristotle Ave in the highly sought-after Bayberry community-where luxury...	4 beds \| 4 baths \| N/A	$619,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.33% Airbnb Rental Income: $null Traditional Rental Income: $4191 Airbnb ROI: N/A Traditional ROI: 5.33%
433 AFTON DR Middletown, DE BACK ON MARKET...Buyer Backed out.....No Fault of the seller. Nestled in the charming Cana...	3 beds \| 4 baths \| N/A	$455,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.75% Airbnb Rental Income: $null Traditional Rental Income: $3331 Airbnb ROI: N/A Traditional ROI: 5.75%
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	$350,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.33% Airbnb Rental Income: $null Traditional Rental Income: $2138 Airbnb ROI: N/A Traditional ROI: 4.33%
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%
1113 COLUMBIA Street Middletown, DE Great homes are made even greater by the communities that surround them, and this neighbor...	4 beds \| 4 baths \| 2,275 sq.ft.	$525,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.18% Airbnb Rental Income: $null Traditional Rental Income: $3438 Airbnb ROI: N/A Traditional ROI: 5.18%
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 Model Middletown, DE Welcome to the Cottonwood Model in the highly sought-after 55+ community of Traditions at ...	3 beds \| 2 baths \| 2,477 sq.ft.	$622,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.58% Airbnb Rental Income: $null Traditional Rental Income: $2797 Airbnb ROI: N/A Traditional ROI: 2.58%
204 BALDY Lane #Chelsea Model Middletown, DE Introducing the CHELSEA model in the highly desirable 55+ community of Traditions At White...	3 beds \| 2 baths \| 2,296 sq.ft.	$607,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.56% Airbnb Rental Income: $null Traditional Rental Income: $2722 Airbnb ROI: N/A Traditional ROI: 2.56%
204 BALDY Lane #Belville Model 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.	$522,000	Airbnb cash on cash: -1.4% Traditional cash on cash: 2.94% Airbnb Rental Income: $857 Traditional Rental Income: $2643 Airbnb ROI: -1.4% 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.	$526,000	Airbnb cash on cash: -1.4% Traditional cash on cash: 2.91% Airbnb Rental Income: $857 Traditional Rental Income: $2643 Airbnb ROI: -1.4% Traditional ROI: 2.91%
204 BALDY Lane #Cayot Model 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.	$587,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.59% Airbnb Rental Income: $null Traditional Rental Income: $2687 Airbnb ROI: N/A Traditional ROI: 2.59%
204 BALDY Lane #Bristole Model Middletown, DE The Bristol Model is a thoughtfully designed 3-bedroom home that is in the highly sought-a...	3 beds \| 2 baths \| 2,441 sq.ft.	$546,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.06% Airbnb Rental Income: $null Traditional Rental Income: $2793 Airbnb ROI: N/A Traditional ROI: 3.06%
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%
1112 S OLMSTED Parkway Middletown, DE *****Home is contingent on the seller buying their next home. They are under contract for ...	3 beds \| 3 baths \| 2,746 sq.ft.	$429,990	Airbnb cash on cash: N/A Traditional cash on cash: 3.38% Airbnb Rental Income: $null Traditional Rental Income: $2246 Airbnb ROI: N/A Traditional ROI: 3.38%
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%
404 PAPER BIRCH Street Middletown, DE Ready to trade the "to-do" list for a "must-do" list? Welcome to 404 Paper Birch Street, n...	2 beds \| 2 baths \| 1,825 sq.ft.	$569,000	Airbnb cash on cash: -1.48% Traditional cash on cash: 2.21% Airbnb Rental Income: $857 Traditional Rental Income: $2487 Airbnb ROI: -1.48% Traditional ROI: 2.21%
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%
105 LITTONDALE COURT Middletown, DE Woods at Lakeside ' Appoquinimink School District ' Four Season Room ' Full unfinished bas...	3 beds \| 3 baths \| 1,725 sq.ft.	$385,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.87% Airbnb Rental Income: $null Traditional Rental Income: $2204 Airbnb ROI: N/A Traditional ROI: 3.87%
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.	$709,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.75% Airbnb Rental Income: $null Traditional Rental Income: $3984 Airbnb ROI: N/A Traditional ROI: 3.75%
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.	$445,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.66% Airbnb Rental Income: $null Traditional Rental Income: $2324 Airbnb ROI: N/A Traditional ROI: 3.66%
330 NIGHTHAWK Drive Middletown, DE Located in the highly sought-after K. Hovnanian Pleasanton community in the heart of Middl...	5 beds \| 4 baths \| 5,033 sq.ft.	$789,990	Airbnb cash on cash: N/A Traditional cash on cash: 2.33% Airbnb Rental Income: $null Traditional Rental Income: $3165 Airbnb ROI: N/A Traditional ROI: 2.33%
328 ANDREW Court Middletown, DE Welcome to this stunning, like-new townhome in the desirable Middletown Reserve community!...	3 beds \| 4 baths \| 2,295 sq.ft.	$487,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.34% Airbnb Rental Income: $null Traditional Rental Income: $2826 Airbnb ROI: N/A Traditional ROI: 3.34%
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: -1.39% Traditional cash on cash: 3.67% Airbnb Rental Income: $857 Traditional Rental Income: $2915 Airbnb ROI: -1.39% Traditional ROI: 3.67%
118 AIRMONT DR Middletown, DE Beautifully updated 5-bedroom, 2-bath home situated on a spacious lot in desirable Middlet...	5 beds \| 2 baths \| N/A	$609,000	Airbnb cash on cash: N/A Traditional cash on cash: 3% Airbnb Rental Income: $null Traditional Rental Income: $2719 Airbnb ROI: N/A Traditional ROI: 3%
632 HARRIER LN Middletown, DE Welcome to 632 Harrier Ln, a 2025-built residence in the desirable Pleasanton community of...	5 beds \| 5 baths \| N/A	$729,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.33% Airbnb Rental Income: $null Traditional Rental Income: $3816 Airbnb ROI: N/A Traditional ROI: 4.33%
1343 BOHEMIA MILL Road Middletown, DE Candyland - A Once-in-a-Generation Equestrian Estate in Middletown, Delaware Welcome to Ca...	4 beds \| 5 baths \| 4,650 sq.ft.	$5,100,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.16% Airbnb Rental Income: $null Traditional Rental Income: $6111 Airbnb ROI: N/A Traditional ROI: 0.16%
240 BALDY LANE Middletown, DE Welcome to Traditions @ Whitehall, a 55+ Active Community just south of the C&D Canal in M...	3 beds \| 2 baths \| 2,725 sq.ft.	$575,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.66% Airbnb Rental Income: $null Traditional Rental Income: $2646 Airbnb ROI: N/A Traditional ROI: 2.66%
8 REDDING CIR Middletown, DE If you've been searching for a move-in ready home that blends style, comfort, and convenie...	3 beds \| 2 baths \| N/A	$359,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.97% Airbnb Rental Income: $null Traditional Rental Income: $1696 Airbnb ROI: N/A Traditional ROI: 2.97%

Real Estate investment in Middletown, DE

There are 146 properties for sale in the city of Middletown . The median list price in Middletown is $429,278 and the average price per square foot is $152. In June 2026, the average monthly cash on cash return in Middletown is 4.00%. The average monthly rental income in Middletown is $2,912.

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

There are 146 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 $2,912.

Your search for investment property begins and ends here

Investment Property for Sale in Middletown, DE

1920 E ARISTOTLE AVE

Middletown, DE

4 beds | 4 baths | N/A

$619,900

Airbnb cash on cash: N/A

Traditional cash on cash: 5.33%

Airbnb Rental Income: $null

Traditional Rental Income: $4191

Airbnb ROI: N/A

Traditional ROI: 5.33%

433 AFTON DR

Middletown, DE

3 beds | 4 baths | N/A

$455,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.75%

Airbnb Rental Income: $null

Traditional Rental Income: $3331

Airbnb ROI: N/A

Traditional ROI: 5.75%

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

$350,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.33%

Airbnb Rental Income: $null

Traditional Rental Income: $2138

Airbnb ROI: N/A

Traditional ROI: 4.33%

32 W MINGLEWOOD DRIVE

Middletown, DE

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%

1113 COLUMBIA Street

Middletown, DE

4 beds | 4 baths | 2,275 sq.ft.

$525,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.18%

Airbnb Rental Income: $null

Traditional Rental Income: $3438

Airbnb ROI: N/A