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
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.	$650,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.33% Airbnb Rental Income: $null Traditional Rental Income: $4468 Airbnb ROI: N/A Traditional ROI: 5.33%
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 #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 unit: 1 Armstrong #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 unit: 2 Clayton #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 unit: 6 Cochran #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%
1381 POLE BRIDGE Road Middletown, DE Here it is, your own piece of ground with a whole lot of extras. 1381 Pole Bridge Road off...	4 beds \| 3 baths \| 3,169 sq.ft.	$825,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.38% Airbnb Rental Income: $null Traditional Rental Income: $3787 Airbnb ROI: N/A Traditional ROI: 2.38%
204 BALDY Lane unit: Cottonwood #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 #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 #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: 0.7% Traditional cash on cash: 2.94% Airbnb Rental Income: $2087 Traditional Rental Income: $2643 Airbnb ROI: 0.7% Traditional ROI: 2.94%
120 BURLINA BLVD unit: Bloomfield Model #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: 0.68% Traditional cash on cash: 2.9% Airbnb Rental Income: $2087 Traditional Rental Income: $2643 Airbnb ROI: 0.68% Traditional ROI: 2.9%
204 BALDY Lane unit: Cayot #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 #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: 3.15% Airbnb Rental Income: $null Traditional Rental Income: $4468 Airbnb ROI: N/A Traditional ROI: 3.15%
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: 2.07% Airbnb Rental Income: $null Traditional Rental Income: $3342 Airbnb ROI: N/A Traditional ROI: 2.07%
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: 2.23% Airbnb Rental Income: $null Traditional Rental Income: $3367 Airbnb ROI: N/A Traditional ROI: 2.23%
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: 1.87% Airbnb Rental Income: $null Traditional Rental Income: $3294 Airbnb ROI: N/A Traditional ROI: 1.87%
1415 WHISPERING WOODS Road Middletown, DE Amazing Price Reduction!Beautiful 2 bedroom 2 bath carriage home in Whispering Woods a 55+...	2 beds \| 2 baths \| 1,875 sq.ft.	$425,000	Airbnb cash on cash: 1.24% Traditional cash on cash: 3.39% Airbnb Rental Income: $2087 Traditional Rental Income: $2408 Airbnb ROI: 1.24% Traditional ROI: 3.39%
14 WHITE OAK DRIVE Middletown, DE Nestled in Great Oak Farms this 4 bedroom, 3 bathroom Brick and Vinyl Ranch Rambler has be...	4 beds \| 3 baths \| 2,225 sq.ft.	$549,999	Airbnb cash on cash: N/A Traditional cash on cash: 5.76% Airbnb Rental Income: $null Traditional Rental Income: $3964 Airbnb ROI: N/A Traditional ROI: 5.76%
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: 2.03% Airbnb Rental Income: $null Traditional Rental Income: $3342 Airbnb ROI: N/A Traditional ROI: 2.03%
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: 3.34% Airbnb Rental Income: $null Traditional Rental Income: $4468 Airbnb ROI: N/A Traditional ROI: 3.34%
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: 2.24% Airbnb Rental Income: $null Traditional Rental Income: $3342 Airbnb ROI: N/A Traditional ROI: 2.24%
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: 2.1% Airbnb Rental Income: $null Traditional Rental Income: $3294 Airbnb ROI: N/A Traditional ROI: 2.1%
464 SMEE Road Middletown, DE Welcome to 464 Smee Road - Your Perfect Home Awaits! Located in the heart of Middletown, D...	3 beds \| 3 baths \| 1,700 sq.ft.	$434,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.56% Airbnb Rental Income: $null Traditional Rental Income: $2265 Airbnb ROI: N/A Traditional ROI: 3.56%
712 WALLASEY Drive Middletown, DE Welcome to 712 Wallasey Drive! This beautiful property by Ryan Homes is located in Middlet...	4 beds \| 5 baths \| 5,561 sq.ft.	$725,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.86% Airbnb Rental Income: $null Traditional Rental Income: $3984 Airbnb ROI: N/A Traditional ROI: 3.86%
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 bea...	3 beds \| 2 baths \| 2,167 sq.ft.	$600,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.89% Airbnb Rental Income: $null Traditional Rental Income: $2660 Airbnb ROI: N/A Traditional ROI: 2.89%
1102 HIGHLAND Street unit: 137 Ashton #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: 0.97% Traditional cash on cash: 3.86% Airbnb Rental Income: $2087 Traditional Rental Income: $2915 Airbnb ROI: 0.97% 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%
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%
365 ANDREW Court Middletown, DE Welcome to 365 Andrew ct, this barely lived-in like new home offers all the benefits of ne...	3 beds \| 4 baths \| N/A	$488,999	Airbnb cash on cash: N/A Traditional cash on cash: 6.09% Airbnb Rental Income: $null Traditional Rental Income: $3418 Airbnb ROI: N/A Traditional ROI: 6.09%
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.	$414,444	Airbnb cash on cash: N/A Traditional cash on cash: 5.37% Airbnb Rental Income: $null Traditional Rental Income: $2675 Airbnb ROI: N/A Traditional ROI: 5.37%
1343 BOHEMIA MILL Road Middletown, DE Welcome to Candyland: Where Dreams Gallop Free! There hasn't been anything like this to hi...	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.	$455,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.18% Airbnb Rental Income: $null Traditional Rental Income: $3303 Airbnb ROI: N/A Traditional ROI: 6.18%
114 AUSTRIAN PINE Court Middletown, DE New Price Alert!! Now Featured at $745,000 Offering $10,000 in Seller's Assistance with an...	4 beds \| 4 baths \| 4,155 sq.ft.	$745,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.45% Airbnb Rental Income: $null Traditional Rental Income: $4857 Airbnb ROI: N/A Traditional ROI: 5.45%
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.	$1,070,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.55% Airbnb Rental Income: $null Traditional Rental Income: $4571 Airbnb ROI: N/A Traditional ROI: 2.55%
530 WHEELMEN Street unit: #2 Middleton Elite #2 Middleton Elite Middletown, DE Middleton Elite -TO BE BUILT new construction. This 3 bedroom open innovative floor plan w...	3 beds \| 3 baths \| 2,052 sq.ft.	$540,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.82% Airbnb Rental Income: $null Traditional Rental Income: $3032 Airbnb ROI: N/A Traditional ROI: 3.82%
530 WHEELMEN Street unit: 3 Middleton Reserve #3 Middleton Reserve Middletown, DE Middleton Reserve -To be built new construction. Photos of similar home shown with optiona...	4 beds \| 3 baths \| 2,280 sq.ft.	$554,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.89% Airbnb Rental Income: $null Traditional Rental Income: $3172 Airbnb ROI: N/A Traditional ROI: 3.89%

Real Estate investment in Middletown, DE

There are 109 properties for sale in the city of Middletown . The median list price in Middletown is $604,900 and the average price per square foot is $199. In October 2025, the average monthly cash on cash return in Middletown is 4.00%. The average monthly rental income in Middletown is $3,183.

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

There are 109 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 $3,183.

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.

$650,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.33%

Airbnb Rental Income: $null

Traditional Rental Income: $4468

Airbnb ROI: N/A

Traditional ROI: 5.33%

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 #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 unit: 1 Armstrong #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 unit: 2 Clayton #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 unit: 6 Cochran #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%

1381 POLE BRIDGE Road

Middletown, DE

4 beds | 3 baths | 3,169 sq.ft.

$825,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.38%

Airbnb Rental Income: $null

Traditional Rental Income: $3787

Airbnb ROI: N/A

Traditional ROI: 2.38%

204 BALDY Lane unit: Cottonwood #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