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
152 TYWYN DRIVE Middletown, DE Check out this beautiful and well-kept 5-bedroom, 3.5-bath home in the popular Preserves a...	5 beds \| 4 baths \| 4,797 sq.ft.	$665,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.19% Airbnb Rental Income: $null Traditional Rental Income: $4468 Airbnb ROI: N/A Traditional ROI: 5.19%
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.	$411,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.69% Airbnb Rental Income: $null Traditional Rental Income: $2615 Airbnb ROI: N/A Traditional ROI: 4.69%
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%
126 GREEN FOREST DRIVE #1 ARMSTRONG Middletown, DE Rothwell Estates from Benchmark Builders. The ARMSTRONG (to be built) is the smaller of ou...	3 beds \| 2 baths \| 2,225 sq.ft.	$638,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.67% Airbnb Rental Income: $null Traditional Rental Income: $2814 Airbnb ROI: N/A Traditional ROI: 2.67%
126 GREEN FOREST DRIVE #2 CLAYTON Middletown, DE Rothwell Estates from Benchmark Builders. The CLAYTON (to be built) is our starter 4 bedro...	4 beds \| 3 baths \| 2,586 sq.ft.	$638,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.59% Airbnb Rental Income: $null Traditional Rental Income: $3177 Airbnb ROI: N/A Traditional ROI: 3.59%
126 GREEN FOREST DRIVE #6 COCHRAN Middletown, DE Rothwell Estates from Benchmark Builders. The COCHRAN (to be built) is the largest of out ...	4 beds \| 3 baths \| 3,700 sq.ft.	$740,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.11% Airbnb Rental Income: $null Traditional Rental Income: $3330 Airbnb ROI: N/A Traditional ROI: 3.11%
340 ELLENWOOD DR Middletown, DE Welcome to 340 Ellenwood Drive, located in one of Middletown's most desirable communities ...	4 beds \| 4 baths \| N/A	$769,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.01% Airbnb Rental Income: $null Traditional Rental Income: $4171 Airbnb ROI: N/A Traditional ROI: 4.01%
20 W KILTS LANE Middletown, DE Showings begin 8/1/2025! Overnight Notice Required for ALL Showing Requests. Sellers Reque...	4 beds \| 4 baths \| 3,425 sq.ft.	$669,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.45% Airbnb Rental Income: $null Traditional Rental Income: $4580 Airbnb ROI: N/A Traditional ROI: 5.45%
1381 POLE BRIDGE ROAD Middletown, DE Motivated Seller! Here it is, your own piece of ground with a whole lot of extras. 1381 Po...	4 beds \| 3 baths \| 3,169 sq.ft.	$899,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.1% Airbnb Rental Income: $null Traditional Rental Income: $3787 Airbnb ROI: N/A Traditional ROI: 2.1%
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: 1.7% Traditional cash on cash: 2.94% Airbnb Rental Income: $2674 Traditional Rental Income: $2643 Airbnb ROI: 1.7% 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: 1.67% Traditional cash on cash: 2.9% Airbnb Rental Income: $2674 Traditional Rental Income: $2643 Airbnb ROI: 1.67% 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: 3.15% Airbnb Rental Income: $null Traditional Rental Income: $4468 Airbnb ROI: N/A Traditional ROI: 3.15%
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: 2.07% Airbnb Rental Income: $null Traditional Rental Income: $3342 Airbnb ROI: N/A Traditional ROI: 2.07%
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: 2.23% Airbnb Rental Income: $null Traditional Rental Income: $3367 Airbnb ROI: N/A Traditional ROI: 2.23%
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: 1.87% Airbnb Rental Income: $null Traditional Rental Income: $3294 Airbnb ROI: N/A Traditional ROI: 1.87%
2138 AUDUBON TRAIL Middletown, DE Nestled in the delightful Bayberry community and located within the award-winning Appoquin...	3 beds \| 3 baths \| 1,975 sq.ft.	$425,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.56% Airbnb Rental Income: $null Traditional Rental Income: $2622 Airbnb ROI: N/A Traditional ROI: 4.56%
1415 WHISPERING WOODS ROAD Middletown, DE Beautiful 2 bedroom 2 bath carriage home in Whispering Woods a 55+ community in Middletown...	2 beds \| 2 baths \| 1,875 sq.ft.	$450,000	Airbnb cash on cash: 2.28% Traditional cash on cash: 3.15% Airbnb Rental Income: $2674 Traditional Rental Income: $2408 Airbnb ROI: 2.28% Traditional ROI: 3.15%
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: 2.03% Airbnb Rental Income: $null Traditional Rental Income: $3342 Airbnb ROI: N/A Traditional ROI: 2.03%
163 BAKERFIELD DRIVE Middletown, DE Discover the charm of this stunning Colonial home nestled in the desirable Commodore Estat...	3 beds \| 3 baths \| 2,475 sq.ft.	$590,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.07% Airbnb Rental Income: $null Traditional Rental Income: $3261 Airbnb ROI: N/A Traditional ROI: 4.07%
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: 3.34% Airbnb Rental Income: $null Traditional Rental Income: $4468 Airbnb ROI: N/A Traditional ROI: 3.34%
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: 2.24% Airbnb Rental Income: $null Traditional Rental Income: $3342 Airbnb ROI: N/A Traditional ROI: 2.24%
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: 2.1% Airbnb Rental Income: $null Traditional Rental Income: $3294 Airbnb ROI: N/A Traditional ROI: 2.1%
5910 RAVEL LANE Middletown, DE 55+ Community. Enter a bright, open floor plan with gleaming hardwood floors. Entertain fr...	2 beds \| 3 baths \| 2,025 sq.ft.	$438,000	Airbnb cash on cash: 2.61% Traditional cash on cash: 2.86% Airbnb Rental Income: $2674 Traditional Rental Income: $2142 Airbnb ROI: 2.61% Traditional ROI: 2.86%
103 WESTSIDE LANE Middletown, DE Welcome to 103 Westside Lane in one of Middletown's most exclusive and coveted communities...	4 beds \| 4 baths \| 4,936 sq.ft.	$693,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.44% Airbnb Rental Income: $null Traditional Rental Income: $3448 Airbnb ROI: N/A Traditional ROI: 3.44%
38 N NEW RD Middletown, DE This waterfront property offers limitless potential. Whether you're seeking a weekend/vaca...	4 beds \| 2 baths \| N/A	$349,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.96% Airbnb Rental Income: $null Traditional Rental Income: $2120 Airbnb ROI: N/A Traditional ROI: 4.96%
734 WOOD DUCK COURT Middletown, DE Welcome to 734 Wood Duck Ct A Stunning Blend of Comfort and Style in Middletown! Nestled ...	4 beds \| 3 baths \| 3,025 sq.ft.	$665,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.4% Airbnb Rental Income: $null Traditional Rental Income: $3244 Airbnb ROI: N/A Traditional ROI: 3.4%
125 PATTERSON COURT Middletown, DE This home is a To-Be- Built. The Amadora offers a private home office off the foyer, a b...	3 beds \| 2 baths \| 2,167 sq.ft.	$599,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.9% Airbnb Rental Income: $null Traditional Rental Income: $2660 Airbnb ROI: N/A Traditional ROI: 2.9%
412 HIGHLAND STREET #137 ASHTON CARRIAGE 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: 2.01% Traditional cash on cash: 3.86% Airbnb Rental Income: $2674 Traditional Rental Income: $2915 Airbnb ROI: 2.01% 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.	$393,297	Airbnb cash on cash: N/A Traditional cash on cash: 5.36% Airbnb Rental Income: $null Traditional Rental Income: $2784 Airbnb ROI: N/A Traditional ROI: 5.36%
1609 SCHWINN STREET Middletown, DE Quick Delivery home from Benchmark Builders in the Town of Whitehall in Middletown DE. Thi...	4 beds \| 3 baths \| 2,737 sq.ft.	$619,999	Airbnb cash on cash: N/A Traditional cash on cash: 4.3% Airbnb Rental Income: $null Traditional Rental Income: $3221 Airbnb ROI: N/A Traditional ROI: 4.3%
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.	$424,444	Airbnb cash on cash: N/A Traditional cash on cash: 5.22% Airbnb Rental Income: $null Traditional Rental Income: $2675 Airbnb ROI: N/A Traditional ROI: 5.22%
1343 BOHEMIA MILL ROAD Middletown, DE Welcome to Candyland: Where Dreams Gallop Free! There hasnt been anything like this to hit...	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%
325 GREAT OAK DRIVE Middletown, DE Classic R.C. Peoples-built 2 Story in rarely available Great Oak Farms. This home has fant...	4 beds \| 3 baths \| 2,150 sq.ft.	$464,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.04% Airbnb Rental Income: $null Traditional Rental Income: $3303 Airbnb ROI: N/A Traditional ROI: 6.04%
635 GORDON HOUSE WAY Middletown, DE New construction without the wait. This gorgeous estate home has everything you could want...	5 beds \| 4 baths \| 3,465 sq.ft.	$671,276	Airbnb cash on cash: N/A Traditional cash on cash: 6% Airbnb Rental Income: $null Traditional Rental Income: $4534 Airbnb ROI: N/A Traditional ROI: 6%
114 AUSTRIAN PINE COURT Middletown, DE Now featured at $755,000 This stunning new home in the highly sought-after Four Seasons a...	4 beds \| 4 baths \| 4,155 sq.ft.	$755,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.37% Airbnb Rental Income: $null Traditional Rental Income: $4857 Airbnb ROI: N/A Traditional ROI: 5.37%
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.	$1,090,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.49% Airbnb Rental Income: $null Traditional Rental Income: $4571 Airbnb ROI: N/A Traditional ROI: 2.49%

Real Estate investment in Middletown, DE

There are 105 properties for sale in the city of Middletown . The median list price in Middletown is $608,000 and the average price per square foot is $210. In September 2025, the average monthly cash on cash return in Middletown is 4.00%. The average monthly rental income in Middletown is $3,167.

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

There are 105 investment properties available for sale in Middletown.

In 2025, 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 $3,167.

Your search for investment property begins and ends here

Investment Property for Sale in Middletown, DE

152 TYWYN DRIVE

Middletown, DE

5 beds | 4 baths | 4,797 sq.ft.

$665,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.19%

Airbnb Rental Income: $null

Traditional Rental Income: $4468

Airbnb ROI: N/A

Traditional ROI: 5.19%

1300 CARRICK COURT #MASSEY ELITE MODEL

Middletown, DE

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

$411,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.69%

Airbnb Rental Income: $null

Traditional Rental Income: $2615

Airbnb ROI: N/A

Traditional ROI: 4.69%

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%

126 GREEN FOREST DRIVE #1 ARMSTRONG

Middletown, DE

3 beds | 2 baths | 2,225 sq.ft.

$638,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.67%

Airbnb Rental Income: $null

Traditional Rental Income: $2814

Airbnb ROI: N/A

Traditional ROI: 2.67%

126 GREEN FOREST DRIVE #2 CLAYTON

Middletown, DE

4 beds | 3 baths | 2,586 sq.ft.

$638,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.59%

Airbnb Rental Income: $null

Traditional Rental Income: $3177

Airbnb ROI: N/A

Traditional ROI: 3.59%

126 GREEN FOREST DRIVE #6 COCHRAN

Middletown, DE

4 beds | 3 baths | 3,700 sq.ft.

$740,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.11%

Airbnb Rental Income: $null

Traditional Rental Income: $3330

Airbnb ROI: N/A

Traditional ROI: 3.11%

340 ELLENWOOD DR

Middletown, DE

4 beds | 4 baths | N/A

$769,900

Airbnb cash on cash: N/A

Traditional cash on cash: 4.01%

Airbnb Rental Income: $null

Traditional Rental Income: $4171

Airbnb ROI: N/A

Traditional ROI: 4.01%

20 W KILTS LANE

Middletown, DE

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

$669,900

Airbnb cash on cash: N/A

Traditional cash on cash: 5.45%

Airbnb Rental Income: $null

Traditional Rental Income: $4580

Airbnb ROI: N/A