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 18 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
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%
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%
400 REDERICK Lane unit: 4 Sassafras Ii #4 Sassafras Ii Middletown, DE TO BE BUILT - The Sassafras II- This beautiful ranch home features 3 bedrooms, 2 full bath...	3 beds \| 2 baths \| 2,200 sq.ft.	$576,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.98% Airbnb Rental Income: $null Traditional Rental Income: $2583 Airbnb ROI: N/A Traditional ROI: 2.98%
51 SPRINGMILL DR Middletown, DE ""Don't Miss This One! Stop Searching - Springmill's BEST VALUE is right here-and this is...	2 beds \| 2 baths \| N/A	$397,000	Airbnb cash on cash: 2.2% Traditional cash on cash: 4.17% Airbnb Rental Income: $2087 Traditional Rental Income: $2287 Airbnb ROI: 2.2% Traditional ROI: 4.17%
715 DAIRY DRIVE Middletown, DE Welcome to this exquisite 4-bedroom, 3.5-bath luxury residence nestled in the sought-after...	4 beds \| 4 baths \| 3,243 sq.ft.	$489,900	Airbnb cash on cash: N/A Traditional cash on cash: 7.3% Airbnb Rental Income: $null Traditional Rental Income: $4174 Airbnb ROI: N/A Traditional ROI: 7.3%
133 PINE VALLEY DRIVE Middletown, DE Situated on a large corner lot, this home has been lovingly maintained by the original own...	4 beds \| 3 baths \| 2,325 sq.ft.	$525,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.4% Airbnb Rental Income: $null Traditional Rental Income: $3142 Airbnb ROI: N/A Traditional ROI: 4.4%
525 CONTEMPLATION WAY Middletown, DE Welcome to 525 Contemplation Way, nestled in the highly sought-after 55+ community of Whis...	3 beds \| 2 baths \| N/A	$475,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.55% Airbnb Rental Income: $null Traditional Rental Income: $2438 Airbnb ROI: N/A Traditional ROI: 3.55%
25 BROWNING CIR Middletown, DE Nestled in the charming Middletown Crossing, this inviting expanded cape, offers a perfect...	5 beds \| 4 baths \| N/A	$600,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.23% Airbnb Rental Income: $null Traditional Rental Income: $3463 Airbnb ROI: N/A Traditional ROI: 4.23%
300 JASPER WAY Middletown, DE Built in 2023 and just two years young, this beautiful 3 bedroom, 3.5 bath home offers ove...	3 beds \| 4 baths \| 3,025 sq.ft.	$615,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.38% Airbnb Rental Income: $null Traditional Rental Income: $3598 Airbnb ROI: N/A Traditional ROI: 4.38%
102 SPRINGMILL DR Middletown, DE A Rare Opportunity Awaits! Private Tree-Lined Lot & Rare Basement in Springmill! Discover ...	2 beds \| 2 baths \| N/A	$475,000	Airbnb cash on cash: 1.94% Traditional cash on cash: 3.09% Airbnb Rental Income: $2087 Traditional Rental Income: $2061 Airbnb ROI: 1.94% Traditional ROI: 3.09%
1018 APPLECROSS DR Middletown, DE 1018 Applecross Drive exudes modern elegance. Located in the Preserve at Deep Creek and o...	5 beds \| 5 baths \| N/A	$700,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.37% Airbnb Rental Income: $null Traditional Rental Income: $6015 Airbnb ROI: N/A Traditional ROI: 7.37%
118 W CRAIL COURT Middletown, DE Welcome to 118 W. Crail Ct. in the Estates at St. Anne. This 4,350 sq. ft. home sits on a ...	4 beds \| 3 baths \| 4,350 sq.ft.	$660,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.26% Airbnb Rental Income: $null Traditional Rental Income: $3188 Airbnb ROI: N/A Traditional ROI: 3.26%
302 PHEASANT VALE Middletown, DE Beautifully maintained contemporary ranch, 2-3 bedrooms, 3 bathrooms, 2 car garage in quie...	3 beds \| 3 baths \| 2,775 sq.ft.	$465,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.82% Airbnb Rental Income: $null Traditional Rental Income: $2964 Airbnb ROI: N/A Traditional ROI: 4.82%
515 BARRYMORE PKY Middletown, DE Welcome to 515 Barrymore Parkway! Built in 2017 by the current owners, this stunning home ...	3 beds \| 2 baths \| N/A	$639,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.44% Airbnb Rental Income: $null Traditional Rental Income: $2594 Airbnb ROI: N/A Traditional ROI: 2.44%
507 LILAC DRIVE Middletown, DE This beautiful contemporary home offers 3,724 sq ft of flexible living space on a professi...	5 beds \| 4 baths \| 3,750 sq.ft.	$695,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.99% Airbnb Rental Income: $null Traditional Rental Income: $4543 Airbnb ROI: N/A Traditional ROI: 4.99%
580 WHISPERING TRL Middletown, DE `Welcome to 580 Whispering Trail, in the fabulous 55+ community of Springmill. This home ...	2 beds \| 2 baths \| N/A	$425,000	Airbnb cash on cash: 1.57% Traditional cash on cash: 2.82% Airbnb Rental Income: $2087 Traditional Rental Income: $2046 Airbnb ROI: 1.57% Traditional ROI: 2.82%
309 S INGRAM COURT Middletown, DE Welcome to 309 S. Ingram Ct, a beautifully maintained and updated home tucked away on a qu...	4 beds \| 4 baths \| 2,675 sq.ft.	$649,999	Airbnb cash on cash: N/A Traditional cash on cash: 5.3% Airbnb Rental Income: $null Traditional Rental Income: $4393 Airbnb ROI: N/A Traditional ROI: 5.3%

Your search for investment property begins and ends here

Single Family Homes for Sale in Middletown, DE

14 WHITE OAK DRIVE

Middletown, DE

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%

38 N NEW RD

Middletown, DE

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%

400 REDERICK Lane unit: 4 Sassafras Ii #4 Sassafras Ii

Middletown, DE

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

$576,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.98%

Airbnb Rental Income: $null

Traditional Rental Income: $2583

Airbnb ROI: N/A

Traditional ROI: 2.98%

51 SPRINGMILL DR

Middletown, DE

2 beds | 2 baths | N/A

$397,000

Airbnb cash on cash: 2.2%

Traditional cash on cash: 4.17%

Airbnb Rental Income: $2087

Traditional Rental Income: $2287

Airbnb ROI: 2.2%

Traditional ROI: 4.17%

715 DAIRY DRIVE

Middletown, DE

4 beds | 4 baths | 3,243 sq.ft.

$489,900

Airbnb cash on cash: N/A

Traditional cash on cash: 7.3%

Airbnb Rental Income: $null

Traditional Rental Income: $4174

Airbnb ROI: N/A

Traditional ROI: 7.3%

133 PINE VALLEY DRIVE

Middletown, DE

4 beds | 3 baths | 2,325 sq.ft.

$525,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.4%

Airbnb Rental Income: $null

Traditional Rental Income: $3142

Airbnb ROI: N/A

Traditional ROI: 4.4%

525 CONTEMPLATION WAY

Middletown, DE

3 beds | 2 baths | N/A

$475,900

Airbnb cash on cash: N/A

Traditional cash on cash: 3.55%

Airbnb Rental Income: $null

Traditional Rental Income: $2438

Airbnb ROI: N/A

Traditional ROI: 3.55%

25 BROWNING CIR

Middletown, DE

5 beds | 4 baths | N/A

$600,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.23%

Airbnb Rental Income: $null

Traditional Rental Income: $3463

Airbnb ROI: N/A