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.

Single Family Homes for Sale in Middletown, DE

Search for Single Family Residential for Sale in Middletown, Delaware. Browse all of Mashvisor’s Single Family Residential listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 244 Single Family Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
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%
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 Ln #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 Ln #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 Ln #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%
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%
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.	$649,900	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 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%
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 Dr #BRANDYWINE GRAND Middletown, DE Welcome to Highlands at Back Creek, a small community of only 42 lots. Most lots back to o...	4 beds \| 2 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%
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.	$565,000	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%
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%
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%
305 White Pine Dr Middletown, DE ONE ACRE!!!!!! UPDATED!!! MOVE IN READY!!! Completely renovated from top to bottom, this s...	3 beds \| 2 baths \| 2,816 sq.ft.	$538,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.8% Airbnb Rental Income: $null Traditional Rental Income: $2343 Airbnb ROI: N/A Traditional ROI: 2.8%
15 Golden Raintree Ct Middletown, DE Welcome to the Eastwood Loft, a thoughtfully designed home offering 3 bedrooms, 4 baths, a...	3 beds \| 4 baths \| 2,441 sq.ft.	$599,990	Airbnb cash on cash: N/A Traditional cash on cash: 2.69% Airbnb Rental Income: $null Traditional Rental Income: $2454 Airbnb ROI: N/A Traditional ROI: 2.69%
114 Austrian Pine Ct 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.	$689,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.81% Airbnb Rental Income: $null Traditional Rental Income: $4857 Airbnb ROI: N/A Traditional ROI: 5.81%
19 Golden Raintree Ct Middletown, DE Welcome to the Dorchester, a thoughtfully designed home offering 3 bedrooms, 3 baths, and ...	3 beds \| 3 baths \| 1,859 sq.ft.	$629,990	Airbnb cash on cash: N/A Traditional cash on cash: 2.53% Airbnb Rental Income: $null Traditional Rental Income: $2465 Airbnb ROI: N/A Traditional ROI: 2.53%
21 Golden Raintree Ct Middletown, DE Welcome to the Killarney I, a thoughtfully designed home offering 3 bedrooms, 3 baths, and...	3 beds \| 3 baths \| 2,080 sq.ft.	$639,990	Airbnb cash on cash: N/A Traditional cash on cash: 2.32% Airbnb Rental Income: $null Traditional Rental Income: $2373 Airbnb ROI: N/A Traditional ROI: 2.32%
251 Dillon Cir Middletown, DE Presenting a distinguished 4-bedroom, 4 full-bathroom, Colorado II model in Summit Pointe,...	4 beds \| 4 baths \| 4,725 sq.ft.	$995,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.96% Airbnb Rental Income: $null Traditional Rental Income: $4571 Airbnb ROI: N/A Traditional ROI: 2.96%
530 Wheelmen St #2 MIDDLETON ELITE Middletown, DE Middleton Elite -TO BE BUILT new construction. This 3 bedroom open innovative floor plan w...	3 beds \| 2 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 St #3 MIDDLETON RESERVE Middletown, DE Middleton Reserve -To be built new construction. Photos of similar home shown with optiona...	4 beds \| 2 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%
530 Wheelmen St #4 ALTON Middletown, DE The Alton Model. TO BE BUILT. Cape Cod style home offering 2 bedrooms, 2 baths, open floor...	3 beds \| 3 baths \| 1,850 sq.ft.	$549,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.05% Airbnb Rental Income: $null Traditional Rental Income: $2715 Airbnb ROI: N/A Traditional ROI: 3.05%
530 Wheelmen St #5 CHADWICK Middletown, DE Benchmark Builders at The Town of Whitehall, Chadwick Floor Plan. TO BE BUILT. The hometow...	4 beds \| 2 baths \| 2,456 sq.ft.	$570,500	Airbnb cash on cash: N/A Traditional cash on cash: 3.75% Airbnb Rental Income: $null Traditional Rental Income: $3172 Airbnb ROI: N/A Traditional ROI: 3.75%
530 Wheelmen St #6 CHARLESTON Middletown, DE CHARLESTON -TO BE BUILT. This 4 bedroom (OPTIONAL 1ST FLOOR 5TH BEDROOM) open floor plan w...	4 beds \| 2 baths \| 2,730 sq.ft.	$590,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.6% Airbnb Rental Income: $null Traditional Rental Income: $3172 Airbnb ROI: N/A Traditional ROI: 3.6%
530 Wheelmen St #7 SAVANNAH Middletown, DE Savannah -To be built. This floor plan feature 4 bedrooms, 2.5 baths, second floor laundry...	4 beds \| 2 baths \| 2,854 sq.ft.	$591,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.59% Airbnb Rental Income: $null Traditional Rental Income: $3172 Airbnb ROI: N/A Traditional ROI: 3.59%
530 Wheelmen St #8 WENTWORTH Middletown, DE Edmonston -TO BE BUILT. Come tour our decorated model during business hours. This 4 bedroo...	4 beds \| 2 baths \| 2,680 sq.ft.	$602,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.51% Airbnb Rental Income: $null Traditional Rental Income: $3172 Airbnb ROI: N/A Traditional ROI: 3.51%
400 Rederick Ln #1 GREENSPRING Middletown, DE TO BE BUILT-The Greenspring -This beautiful home features 4 bedrooms, 2.5 baths, 2 car gar...	4 beds \| 2 baths \| 3,021 sq.ft.	$619,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.82% Airbnb Rental Income: $null Traditional Rental Income: $3189 Airbnb ROI: N/A Traditional ROI: 3.82%
400 Rederick Ln #2 OXFORD Middletown, DE TO BE BUILT - The Oxford - Whether you're looking for a detached homes home large enough t...	4 beds \| 2 baths \| 2,357 sq.ft.	$582,500	Airbnb cash on cash: N/A Traditional cash on cash: 3.75% Airbnb Rental Income: $null Traditional Rental Income: $2989 Airbnb ROI: N/A Traditional ROI: 3.75%
400 Rederick Ln #3 BENNETT Middletown, DE TO BE BUILT - The Bennett This beautiful 2 story home features 4 bedrooms, 2.5 baths, 2 ca...	4 beds \| 2 baths \| 3,000 sq.ft.	$624,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.77% Airbnb Rental Income: $null Traditional Rental Income: $3189 Airbnb ROI: N/A Traditional ROI: 3.77%

Your search for investment property begins and ends here

Single Family Homes for Sale in Middletown, DE

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%

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 Ln #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

Traditional ROI: 2.58%

204 Baldy Ln #CHELSEA MODEL

Middletown, DE

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 Ln #BELVILLE MODEL

Middletown, DE

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

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