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 13 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
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%
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%
230 ANGLESEY Drive Middletown, DE Welcome to 230 Anglesey Drive, a stunning home where luxury and thoughtful design meet eve...	2 beds \| 3 baths \| 2,475 sq.ft.	$584,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.93% Airbnb Rental Income: $null Traditional Rental Income: $2841 Airbnb ROI: N/A Traditional ROI: 2.93%
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: 6.16% Airbnb Rental Income: $null Traditional Rental Income: $2619 Airbnb ROI: N/A Traditional ROI: 6.16%
847 SILVER RUN Road Middletown, DE PRICE IMPROVEMENT! Enjoy breathtaking sunsets and peaceful privacy from this bright and su...	3 beds \| 2 baths \| 1,375 sq.ft.	$475,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.81% Airbnb Rental Income: $null Traditional Rental Income: $2619 Airbnb ROI: N/A Traditional ROI: 3.81%

Your search for investment property begins and ends here

Single Family Homes for Sale in Middletown, DE

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%

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

Traditional ROI: 4.05%

230 ANGLESEY Drive

Middletown, DE

2 beds | 3 baths | 2,475 sq.ft.

$584,900

Airbnb cash on cash: N/A

Traditional cash on cash: 2.93%

Airbnb Rental Income: $null

Traditional Rental Income: $2841

Airbnb ROI: N/A

Traditional ROI: 2.93%

434 BAKER FARM DR

Middletown, DE

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