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%
1300 Carrick Ct #MASSEY ELITE MODEL Middletown, DE BASE PRICE LISTING - MODEL HOME IS NOT FOR SALE. Welcome to a stylish and spacious 3-story...	3 beds \| 2 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 St #1 EDMONSTON Middletown, DE Edmonston -TO BE BUILT. Come tour our decorated model during business hours. This 4 bedroo...	4 beds \| 2 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%
211 E Crail Ct Middletown, DE Welcome to The Estate at St. Anne's! This beautifully updated 4 bedroom, 2.5 bath home off...	4 beds \| 2 baths \| 2,875 sq.ft.	$644,999	Airbnb cash on cash: N/A Traditional cash on cash: 3.39% Airbnb Rental Income: $null Traditional Rental Income: $3347 Airbnb ROI: N/A Traditional ROI: 3.39%
138 Green Forest Dr Middletown, DE Welcome to 138 Green Forest Drive, a beautifully appointed 4&5 bedroom home offering gener...	4 beds \| 3 baths \| 5,877 sq.ft.	$749,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.28% Airbnb Rental Income: $null Traditional Rental Income: $4165 Airbnb ROI: N/A Traditional ROI: 4.28%
32 W Minglewood Dr Middletown, DE Located in the desirable Cricklewood community in Middletown Delaware, this well-maintaine...	3 beds \| 2 baths \| 2,200 sq.ft.	$515,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.52% Airbnb Rental Income: $null Traditional Rental Income: $2750 Airbnb ROI: N/A Traditional ROI: 3.52%
23 Browning Cir Middletown, DE Welcome to 23 Browning Circle, where comfort, privacy, and thoughtful design come together...	4 beds \| 2 baths \| 3,575 sq.ft.	$600,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.28% Airbnb Rental Income: $null Traditional Rental Income: $4683 Airbnb ROI: N/A Traditional ROI: 6.28%
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: N/A Traditional cash on cash: 2.94% Airbnb Rental Income: $null Traditional Rental Income: $2643 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 2.91% Airbnb Rental Income: $null Traditional Rental Income: $2643 Airbnb ROI: N/A Traditional ROI: 2.91%
204 Baldy Ln #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 Ln #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%
108 Green Forest Dr Middletown, DE Why wait for new construction when this beautiful home is ready for you ! It sits on one...	6 beds \| 3 baths \| 3,700 sq.ft.	$734,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.77% Airbnb Rental Income: $null Traditional Rental Income: $2989 Airbnb ROI: N/A Traditional ROI: 2.77%
34 Crenshaw Ct Middletown, DE This 3 level townhouse is ready for a new owner. This well maintained townhouse has so muc...	3 beds \| 2 baths \| 2,280 sq.ft.	$377,995	Airbnb cash on cash: N/A Traditional cash on cash: 4.68% Airbnb Rental Income: $null Traditional Rental Income: $2317 Airbnb ROI: N/A Traditional ROI: 4.68%
273 ABBOTSFORD 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.	$904,990	Airbnb cash on cash: N/A Traditional cash on cash: 3.24% Airbnb Rental Income: $null Traditional Rental Income: $4468 Airbnb ROI: N/A Traditional ROI: 3.24%
273 ABBOTSFORD 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.	$819,990	Airbnb cash on cash: N/A Traditional cash on cash: 2.2% Airbnb Rental Income: $null Traditional Rental Income: $3342 Airbnb ROI: N/A Traditional ROI: 2.2%
273 ABBOTSFORD 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.	$789,990	Airbnb cash on cash: N/A Traditional cash on cash: 2.36% Airbnb Rental Income: $null Traditional Rental Income: $3367 Airbnb ROI: N/A Traditional ROI: 2.36%
273 Abbotsford Dr #RITTENHOUSE Middletown, DE Welcome to Highlands at Back Creek- a small community of only 42 lots. Most lots back to o...	4 beds \| 2 baths \| 4,569 sq.ft.	$859,990	Airbnb cash on cash: N/A Traditional cash on cash: 2% Airbnb Rental Income: $null Traditional Rental Income: $3294 Airbnb ROI: N/A Traditional ROI: 2%
404 Paper Birch St 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: N/A Traditional cash on cash: 2.21% Airbnb Rental Income: $null Traditional Rental Income: $2487 Airbnb ROI: N/A Traditional ROI: 2.21%
232 Beckington Ct Middletown, DE Welcome home to this beautifully maintained townhome in the heart of Middletown, where sma...	3 beds \| 2 baths \| 2,445 sq.ft.	$395,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.96% Airbnb Rental Income: $null Traditional Rental Income: $2900 Airbnb ROI: N/A Traditional ROI: 5.96%
313 Autumn Ct Middletown, DE Welcome to the sought after Middletown community of The Estates at Dove Run!oMove right in...	4 beds \| 3 baths \| 3,975 sq.ft.	$669,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.51% Airbnb Rental Income: $null Traditional Rental Income: $3300 Airbnb ROI: N/A Traditional ROI: 3.51%
273 ABBOTSFORD 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.	$829,990	Airbnb cash on cash: N/A Traditional cash on cash: 2.17% Airbnb Rental Income: $null Traditional Rental Income: $3342 Airbnb ROI: N/A Traditional ROI: 2.17%
273 Abbotsford Dr #PHILADELPHIAN GRAND Middletown, DE Welcome to Highlands at Back Creek- a small community of only 42 lots. All homesites are a...	4 beds \| 3 baths \| 4,400 sq.ft.	$864,990	Airbnb cash on cash: N/A Traditional cash on cash: 3.44% Airbnb Rental Income: $null Traditional Rental Income: $4468 Airbnb ROI: N/A Traditional ROI: 3.44%
264 Trellis Ln Middletown, DE Fantastic Clean, Cozy Townhome in THE BEST 55+ Community of the Middletown area, SPRING AR...	2 beds \| 2 baths \| 1,800 sq.ft.	$411,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.83% Airbnb Rental Income: $null Traditional Rental Income: $1863 Airbnb ROI: N/A Traditional ROI: 1.83%
273 Abbotsford Dr #HANCOCK GRAND Middletown, DE Welcome to the Highlands at Back Creek- a small community of only 42 lots. Most lots back ...	4 beds \| 2 baths \| 3,260 sq.ft.	$778,990	Airbnb cash on cash: N/A Traditional cash on cash: 2.37% Airbnb Rental Income: $null Traditional Rental Income: $3342 Airbnb ROI: N/A Traditional ROI: 2.37%
273 ABBOTSFORD 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.	$794,990	Airbnb cash on cash: N/A Traditional cash on cash: 2.24% Airbnb Rental Income: $null Traditional Rental Income: $3294 Airbnb ROI: N/A Traditional ROI: 2.24%
409 Galway Ct Middletown, DE Welcome to 409 Galway Court in the Popular Community of Hyetts Crossing. Conveniently loca...	3 beds \| 3 baths \| 1,700 sq.ft.	$440,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.71% Airbnb Rental Income: $null Traditional Rental Income: $2324 Airbnb ROI: N/A Traditional ROI: 3.71%
103 Westside Ln Middletown, DE Welcome to 103 Westside Lane in one of Middletown's most exclusive and coveted communities...	4 beds \| 3 baths \| 4,936 sq.ft.	$659,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.67% Airbnb Rental Income: $null Traditional Rental Income: $3448 Airbnb ROI: N/A Traditional ROI: 3.67%
1723 W Matisse Dr Middletown, DE Welcome to 1723 West Matisse Drive! Located in the highly sought-after community of the Vi...	4 beds \| 2 baths \| 3,025 sq.ft.	$570,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.42% Airbnb Rental Income: $null Traditional Rental Income: $3437 Airbnb ROI: N/A Traditional ROI: 4.42%
328 Andrew Ct Middletown, DE Welcome to this stunning, like-new townhome in the desirable Middletown Reserve community!...	3 beds \| 2 baths \| 2,295 sq.ft.	$477,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.58% Airbnb Rental Income: $null Traditional Rental Income: $2826 Airbnb ROI: N/A Traditional ROI: 3.58%
460 Rederick Ln #MASSEY LOT 61 Middletown, DE ** WORKFORCE HOUSING-BUYER MUST QUALIFY FOR THE NEW CASTLE COUNTY PROGRAM TO PURCHASE - MA...	3 beds \| 2 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%
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	$599,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.06% Airbnb Rental Income: $null Traditional Rental Income: $2719 Airbnb ROI: N/A Traditional ROI: 3.06%
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%
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%
1343 Bohemia Mill Rd Middletown, DE Candyland - A Once-in-a-Generation Equestrian Estate in Middletown, Delaware Welcome to Ca...	4 beds \| 4 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	$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 333 properties for sale in the city of Middletown . The median list price in Middletown is $429,243 and the average price per square foot is $152. In July 2026, the average monthly cash on cash return in Middletown is 3.00%. The average monthly rental income in Middletown is $2,496.

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

There are 333 investment properties available for sale in Middletown.

In 2026, the best neighborhood to buy investment property is Middletown.

The ROI for Short-Term is higher than the Long-Term in Middletown with average rental income of $N/A.

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%

1300 Carrick Ct #MASSEY ELITE MODEL

Middletown, DE

3 beds | 2 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 St #1 EDMONSTON

Middletown, DE

4 beds | 2 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%

211 E Crail Ct

Middletown, DE

4 beds | 2 baths | 2,875 sq.ft.

$644,999

Airbnb cash on cash: N/A

Traditional cash on cash: 3.39%

Airbnb Rental Income: $null

Traditional Rental Income: $3347

Airbnb ROI: N/A

Traditional ROI: 3.39%

138 Green Forest Dr

Middletown, DE

4 beds | 3 baths | 5,877 sq.ft.

$749,900

Airbnb cash on cash: N/A

Traditional cash on cash: 4.28%

Airbnb Rental Income: $null

Traditional Rental Income: $4165

Airbnb ROI: N/A

Traditional ROI: 4.28%

32 W Minglewood Dr

Middletown, DE

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

$515,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.52%

Airbnb Rental Income: $null

Traditional Rental Income: $2750

Airbnb ROI: N/A

Traditional ROI: 3.52%

23 Browning Cir

Middletown, DE

4 beds | 2 baths | 3,575 sq.ft.

$600,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.28%

Airbnb Rental Income: $null

Traditional Rental Income: $4683

Airbnb ROI: N/A

Traditional ROI: 6.28%

204 BALDY Lane #Cottonwood Model

Middletown, DE

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