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
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%
1300 CARRICK Court unit: Massey Elite Model #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 unit: 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 24 Hours Notice Required for ALL Showings. Even though this property is in good shape and ...	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.	$549,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.24% Airbnb Rental Income: $null Traditional Rental Income: $2750 Airbnb ROI: N/A Traditional ROI: 3.24%
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 unit: 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 unit: 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 unit: 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: -1.3% Traditional cash on cash: 2.94% Airbnb Rental Income: $917 Traditional Rental Income: $2643 Airbnb ROI: -1.3% Traditional ROI: 2.94%
120 BURLINA BLVD unit: 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: -1.3% Traditional cash on cash: 2.9% Airbnb Rental Income: $917 Traditional Rental Income: $2643 Airbnb ROI: -1.3% Traditional ROI: 2.9%
204 BALDY Lane unit: 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 unit: 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 unit: Plaza #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 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%
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 unit: Rittenhouse #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 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%
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: 6.11% Airbnb Rental Income: $null Traditional Rental Income: $3522 Airbnb ROI: N/A Traditional ROI: 6.11%
129 AYSHIRE Drive unit: Philadelphian Grand #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 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%
129 AYSHIRE Drive unit: Brandywine Grand #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 WELCOME to 712 Wallasey Dr, the HUGE previously SENECA MODEL HOME by Ryan Homes. It is loc...	4 beds \| 5 baths \| 4,450 sq.ft.	$699,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.82% Airbnb Rental Income: $null Traditional Rental Income: $3984 Airbnb ROI: N/A Traditional ROI: 3.82%
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%
1102 HIGHLAND Street unit: 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: -1.09% Traditional cash on cash: 3.86% Airbnb Rental Income: $917 Traditional Rental Income: $2915 Airbnb ROI: -1.09% Traditional ROI: 3.86%
460 REDERICK Lane unit: Massey Lot 61 #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%
467 HYETTS CORNER Road Middletown, DE Vintage charm with modern amenities. This home built in the 1800s is on just about 1 acre....	3 beds \| 3 baths \| 1,900 sq.ft.	$399,777	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%
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%
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	$386,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.69% Airbnb Rental Income: $null Traditional Rental Income: $1696 Airbnb ROI: N/A Traditional ROI: 2.69%
15 GOLDEN RAINTREE Court Middletown, DE This is a To-Be-Built Home. The Eastwood is a beautifully designed one-story floorplan off...	2 beds \| 2 baths \| 1,780 sq.ft.	$504,400	Airbnb cash on cash: -0.6% Traditional cash on cash: 3.38% Airbnb Rental Income: $917 Traditional Rental Income: $2454 Airbnb ROI: -0.6% Traditional ROI: 3.38%
114 AUSTRIAN PINE Court Middletown, DE Looking for that perfect place to call home? Look no further! Not only is this gorgeous ho...	4 beds \| 4 baths \| 2,595 sq.ft.	$715,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.62% Airbnb Rental Income: $null Traditional Rental Income: $4857 Airbnb ROI: N/A Traditional ROI: 5.62%
19 GOLDEN RAINTREE Court Middletown, DE This is a To-Be-Built Home. The Rockford is a beautifully designed one-story floorplan off...	3 beds \| 3 baths \| 2,378 sq.ft.	$580,400	Airbnb cash on cash: N/A Traditional cash on cash: 2.83% Airbnb Rental Income: $null Traditional Rental Income: $2465 Airbnb ROI: N/A Traditional ROI: 2.83%
251 DILLON Circle Middletown, DE Presenting a distinguished 4-bedroom, 4 full-bathroom, Colorado II model in Summit Pointe,...	4 beds \| 4 baths \| 4,725 sq.ft.	$1,049,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.88% Airbnb Rental Income: $null Traditional Rental Income: $4571 Airbnb ROI: N/A Traditional ROI: 2.88%

Real Estate investment in Middletown, DE

There are 126 properties for sale in the city of Middletown . The median list price in Middletown is $582,500 and the average price per square foot is $214. In April 2026, the average monthly cash on cash return in Middletown is 4.00%. The average monthly rental income in Middletown is $2,841.

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

There are 126 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 $2,841.

Your search for investment property begins and ends here

Investment Property for Sale in Middletown, DE

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%

1300 CARRICK Court unit: Massey Elite Model #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 unit: 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

Traditional ROI: 4.12%

32 W MINGLEWOOD DRIVE

Middletown, DE

3 beds | 3 baths | 2,200 sq.ft.

$549,900

Airbnb cash on cash: N/A

Traditional cash on cash: 3.24%

Airbnb Rental Income: $null

Traditional Rental Income: $2750

Airbnb ROI: N/A

Traditional ROI: 3.24%

3 REDDING CIR

Middletown, DE

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 unit: Cottonwood

Middletown, DE

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