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 15 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
107 BOHEMIA MILL POND DRIVE Middletown, DE Luxury, utility, and modern refinement meet at 107 Bohemia Mill Pond Dr. Situated on a pri...	5 beds \| 3 baths \| 3,675 sq.ft.	$989,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.96% Airbnb Rental Income: $null Traditional Rental Income: $3568 Airbnb ROI: N/A Traditional ROI: 1.96%
113 CRAWFORD ST Middletown, DE Welcome to 113 Crawford Street. Located in the heart of Middletown, Delaware. Enjoy close...	3 beds \| 2 baths \| N/A	$365,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.12% Airbnb Rental Income: $null Traditional Rental Income: $2138 Airbnb ROI: N/A Traditional ROI: 4.12%
32 W MINGLEWOOD DRIVE Middletown, DE Located in the desirable Cricklewood community in Middletown Delaware, this well-maintaine...	3 beds \| 3 baths \| 2,200 sq.ft.	$549,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.24% Airbnb Rental Income: $null Traditional Rental Income: $2750 Airbnb ROI: N/A Traditional ROI: 3.24%
3 REDDING CIR Middletown, DE OFFER DEADLINE: TUESDAY 3/24/2026 @ 2PM EST. Priced to sell! Located in the highly desirab...	3 beds \| 1 baths \| N/A	$280,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.8% Airbnb Rental Income: $null Traditional Rental Income: $1653 Airbnb ROI: N/A Traditional ROI: 3.8%
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	$386,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.69% Airbnb Rental Income: $null Traditional Rental Income: $1696 Airbnb ROI: N/A Traditional ROI: 2.69%
258 DILLON CIRCLE Middletown, DE Nestled in the prestigious Summit Pointe community, this exquisite Colonial-style residenc...	4 beds \| 4 baths \| 4,175 sq.ft.	$995,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.69% Airbnb Rental Income: $null Traditional Rental Income: $4203 Airbnb ROI: N/A Traditional ROI: 2.69%
12 E COCHRAN STREET Middletown, DE Very unusual historic home in the heart of Middletown. Just blocks from new YMCA. Home was...	4 beds \| 3 baths \| 2,275 sq.ft.	$596,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.14% Airbnb Rental Income: $null Traditional Rental Income: $2796 Airbnb ROI: N/A Traditional ROI: 3.14%
1 HOGAN CIR Middletown, DE Discover the charm of this stunning traditional home nestled in the desirable subdivision ...	4 beds \| 3 baths \| N/A	$599,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.05% Airbnb Rental Income: $null Traditional Rental Income: $3365 Airbnb ROI: N/A Traditional ROI: 4.05%
1220 N OLMSTED Parkway Middletown, DE Welcome home to 1220 N Olmsted Pkwy located in the sought-after Village of Bayberry North....	2 beds \| 2 baths \| 1,850 sq.ft.	$569,000	Airbnb cash on cash: -0.85% Traditional cash on cash: 2.7% Airbnb Rental Income: $917 Traditional Rental Income: $2464 Airbnb ROI: -0.85% Traditional ROI: 2.7%
434 BAKER FARM DR Middletown, DE Experience the rare opportunity to own a truly move""Ã¢â¬Ëin""Ã¢â¬Ëready, ""better""Ã¢...	5 beds \| 4 baths \| N/A	$700,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.42% Airbnb Rental Income: $null Traditional Rental Income: $4244 Airbnb ROI: N/A Traditional ROI: 4.42%
108 E COCHRAN ST Middletown, DE Welcome to 108 E Cochran Avenue in the heart of Middletown, Delaware. This cute house has...	3 beds \| 1 baths \| N/A	$339,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.45% Airbnb Rental Income: $null Traditional Rental Income: $1754 Airbnb ROI: N/A Traditional ROI: 3.45%
79 LATTICE Lane Middletown, DE Welcome to 79 Lattice Lane, a beautifully maintained detached ranch home in the highly des...	2 beds \| 2 baths \| 2,275 sq.ft.	$499,000	Airbnb cash on cash: -1.43% Traditional cash on cash: 2.93% Airbnb Rental Income: $917 Traditional Rental Income: $2610 Airbnb ROI: -1.43% Traditional ROI: 2.93%
27 SPRINGMILL DR Middletown, DE Enjoy easy main-level living in this beautifully designed home featuring 2 bedrooms, 2 bat...	2 beds \| 2 baths \| N/A	$435,000	Airbnb cash on cash: -0.9% Traditional cash on cash: 2.62% Airbnb Rental Income: $917 Traditional Rental Income: $2006 Airbnb ROI: -0.9% Traditional ROI: 2.62%

Your search for investment property begins and ends here

Single Family Homes for Sale in Middletown, DE

107 BOHEMIA MILL POND DRIVE

Middletown, DE

5 beds | 3 baths | 3,675 sq.ft.

$989,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.96%

Airbnb Rental Income: $null

Traditional Rental Income: $3568

Airbnb ROI: N/A

Traditional ROI: 1.96%

113 CRAWFORD ST

Middletown, DE

3 beds | 2 baths | N/A

$365,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.12%

Airbnb Rental Income: $null

Traditional Rental Income: $2138

Airbnb ROI: N/A

Traditional ROI: 4.12%

32 W MINGLEWOOD DRIVE

Middletown, DE

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

$549,900

Airbnb cash on cash: N/A

Traditional cash on cash: 3.24%

Airbnb Rental Income: $null

Traditional Rental Income: $2750

Airbnb ROI: N/A

Traditional ROI: 3.24%

3 REDDING CIR

Middletown, DE

3 beds | 1 baths | N/A

$280,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.8%

Airbnb Rental Income: $null

Traditional Rental Income: $1653

Airbnb ROI: N/A

Traditional ROI: 3.8%

8 REDDING CIR

Middletown, DE

3 beds | 2 baths | N/A

$386,900

Airbnb cash on cash: N/A

Traditional cash on cash: 2.69%

Airbnb Rental Income: $null

Traditional Rental Income: $1696

Airbnb ROI: N/A

Traditional ROI: 2.69%

258 DILLON CIRCLE

Middletown, DE

4 beds | 4 baths | 4,175 sq.ft.

$995,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.69%

Airbnb Rental Income: $null

Traditional Rental Income: $4203

Airbnb ROI: N/A

Traditional ROI: 2.69%

12 E COCHRAN STREET

Middletown, DE

4 beds | 3 baths | 2,275 sq.ft.

$596,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.14%

Airbnb Rental Income: $null

Traditional Rental Income: $2796

Airbnb ROI: N/A

Traditional ROI: 3.14%

1 HOGAN CIR

Middletown, DE

4 beds | 3 baths | N/A

$599,900

Airbnb cash on cash: N/A

Traditional cash on cash: 4.05%

Airbnb Rental Income: $null

Traditional Rental Income: $3365

Airbnb ROI: N/A