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 158 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
1920 E ARISTOTLE AVE Middletown, DE Welcome to 1920 E Aristotle Ave in the highly sought-after Bayberry community-where luxury...	4 beds \| 4 baths \| N/A	$619,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.33% Airbnb Rental Income: $null Traditional Rental Income: $4191 Airbnb ROI: N/A Traditional ROI: 5.33%
627 Nesting Ln Middletown, DE This property is an amazing opportunity to own a huge beautiful home, in the Estates at Do...	8 beds \| 4 baths \| 5,950 sq.ft.	$850,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.24% Airbnb Rental Income: $null Traditional Rental Income: $3874 Airbnb ROI: N/A Traditional ROI: 3.24%
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	$350,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.33% Airbnb Rental Income: $null Traditional Rental Income: $2138 Airbnb ROI: N/A Traditional ROI: 4.33%
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.	$525,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.43% Airbnb Rental Income: $null Traditional Rental Income: $2750 Airbnb ROI: N/A Traditional ROI: 3.43%
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%
130 S Lores Landing Rd Middletown, DE	4 beds \| 2 baths \| 2,900 sq.ft.	$628,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.7% Airbnb Rental Income: $null Traditional Rental Income: $2658 Airbnb ROI: N/A Traditional ROI: 2.7%
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.	$664,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.63% Airbnb Rental Income: $null Traditional Rental Income: $3448 Airbnb ROI: N/A Traditional ROI: 3.63%
431 Georgiana Dr Middletown, DE Wow wow WOW!! This meticulously maintained 9-year old home in the desirable Crossland at t...	5 beds \| 3 baths \| 4,272 sq.ft.	$765,000	Airbnb cash on cash: N/A Traditional cash on cash: 3% Airbnb Rental Income: $null Traditional Rental Income: $3425 Airbnb ROI: N/A Traditional ROI: 3%
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%
240 BALDY LANE Middletown, DE Welcome to Traditions @ Whitehall, a 55+ Active Community just south of the C&D Canal in M...	3 beds \| 2 baths \| 2,725 sq.ft.	$575,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.66% Airbnb Rental Income: $null Traditional Rental Income: $2646 Airbnb ROI: N/A Traditional ROI: 2.66%
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	$365,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.9% Airbnb Rental Income: $null Traditional Rental Income: $1696 Airbnb ROI: N/A Traditional ROI: 2.9%
15 GOLDEN RAINTREE Court Middletown, DE This is a To-Be-Built Home. The Eastwood is a beautifully designed one-story floorplan off...	2 beds \| 2 baths \| 1,780 sq.ft.	$499,900	Airbnb cash on cash: -0.61% Traditional cash on cash: 3.42% Airbnb Rental Income: $910 Traditional Rental Income: $2454 Airbnb ROI: -0.61% Traditional ROI: 3.42%
19 GOLDEN RAINTREE Court Middletown, DE This is a To-Be-Built Home. The Rockford is a beautifully designed one-story floorplan off...	3 beds \| 3 baths \| 2,378 sq.ft.	$577,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.85% Airbnb Rental Income: $null Traditional Rental Income: $2465 Airbnb ROI: N/A Traditional ROI: 2.85%
1736 Lord Tennyson Pl Middletown, DE Coming Fall 2025 - This Gable Colonial floorplan offers 4 bedrooms and 2.5 baths with 2,47...	4 beds \| 2 baths \| 2,410 sq.ft.	$624,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.46% Airbnb Rental Income: $null Traditional Rental Income: $3074 Airbnb ROI: N/A Traditional ROI: 3.46%
5730 W Central Park Dr Middletown, DE Coming Fall 2025 - This Adams Craftsman floorplan has a total of 3,364 square feet, which ...	5 beds \| 3 baths \| 3,217 sq.ft.	$723,500	Airbnb cash on cash: N/A Traditional cash on cash: 5.04% Airbnb Rental Income: $null Traditional Rental Income: $4604 Airbnb ROI: N/A Traditional ROI: 5.04%
619 Mccracken Dr Middletown, DE LAST BUILD IN THE NEIGHBORHOOD. We are about to break ground on this beautiful Houston in ...	5 beds \| 3 baths \| 4,070 sq.ft.	$784,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.66% Airbnb Rental Income: $null Traditional Rental Income: $3670 Airbnb ROI: N/A Traditional ROI: 3.66%
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	$595,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.1% Airbnb Rental Income: $null Traditional Rental Income: $3365 Airbnb ROI: N/A Traditional ROI: 4.1%
836 Sweet Birch Dr Middletown, DE 836 Sweet Birch Dr, Middletown, DE 19709 \| Single Family Residential	4 beds \| 4 baths \| 5,446 sq.ft.	$979,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.91% Airbnb Rental Income: $null Traditional Rental Income: $3350 Airbnb ROI: N/A Traditional ROI: 1.91%
1268 Pimpernell Path Middletown, DE 1268 Pimpernell Path, Middletown, DE 19709 \| Single Family Residential	6 beds \| 4 baths \| 5,590 sq.ft.	$830,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.61% Airbnb Rental Income: $null Traditional Rental Income: $3368 Airbnb ROI: N/A Traditional ROI: 2.61%
624 Nesting Ln Middletown, DE 624 Nesting Ln, Middletown, DE 19709 \| Single Family Residential	4 beds \| 4 baths \| 4,725 sq.ft.	$750,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.78% Airbnb Rental Income: $null Traditional Rental Income: $3141 Airbnb ROI: N/A Traditional ROI: 2.78%
692 Bayview Rd Middletown, DE 692 Bayview Rd, Middletown, DE 19709 \| Single Family Residential	N/A beds \| N/A baths \| 7,026 sq.ft.	$1,200,000	Airbnb cash on cash: N/A Traditional cash on cash: -1.04% Airbnb Rental Income: $null Traditional Rental Income: $683 Airbnb ROI: N/A Traditional ROI: -1.04%
Cassidy Plan Middletown, DE Cassidy Plan, Middletown, DE 19709 \| Single Family Residential	4 beds \| 3 baths \| 3,439 sq.ft.	$695,400	Airbnb cash on cash: N/A Traditional cash on cash: 2.11% Airbnb Rental Income: $null Traditional Rental Income: $2480 Airbnb ROI: N/A Traditional ROI: 2.11%
Newport Plan Middletown, DE Newport Plan, Middletown, DE 19709 \| Single Family Residential	3 beds \| 2 baths \| 2,381 sq.ft.	$605,400	Airbnb cash on cash: N/A Traditional cash on cash: 2.21% Airbnb Rental Income: $null Traditional Rental Income: $2227 Airbnb ROI: N/A Traditional ROI: 2.21%
Chesapeake Plan Middletown, DE Chesapeake Plan, Middletown, DE 19709 \| Single Family Residential	4 beds \| 3 baths \| 4,430 sq.ft.	$755,400	Airbnb cash on cash: N/A Traditional cash on cash: 1.82% Airbnb Rental Income: $null Traditional Rental Income: $2480 Airbnb ROI: N/A Traditional ROI: 1.82%
1487 Bunker Hill Rd Middletown, DE 1487 Bunker Hill Rd, Middletown, DE 19709 \| Single Family Residential	4 beds \| 2 baths \| 2,223 sq.ft.	$621,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.18% Airbnb Rental Income: $null Traditional Rental Income: $2270 Airbnb ROI: N/A Traditional ROI: 2.18%
Bridgeport Plan Middletown, DE Bridgeport Plan, Middletown, DE 19709 \| Single Family Residential	4 beds \| 4 baths \| 4,146 sq.ft.	$765,400	Airbnb cash on cash: N/A Traditional cash on cash: 2.81% Airbnb Rental Income: $null Traditional Rental Income: $3213 Airbnb ROI: N/A Traditional ROI: 2.81%
Mayberry Plan Middletown, DE Mayberry Plan, Middletown, DE 19709 \| Single Family Residential	3 beds \| 2 baths \| 2,925 sq.ft.	$665,400	Airbnb cash on cash: N/A Traditional cash on cash: 1.87% Airbnb Rental Income: $null Traditional Rental Income: $2227 Airbnb ROI: N/A Traditional ROI: 1.87%
Jameson Plan Middletown, DE Jameson Plan, Middletown, DE 19709 \| Single Family Residential	3 beds \| 2 baths \| 4,123 sq.ft.	$715,400	Airbnb cash on cash: N/A Traditional cash on cash: 0.79% Airbnb Rental Income: $null Traditional Rental Income: $1664 Airbnb ROI: N/A Traditional ROI: 0.79%
Shearwater Plan Middletown, DE Shearwater Plan, Middletown, DE 19709 \| Single Family Residential	3 beds \| 2 baths \| 3,990 sq.ft.	$735,400	Airbnb cash on cash: N/A Traditional cash on cash: 0.73% Airbnb Rental Income: $null Traditional Rental Income: $1664 Airbnb ROI: N/A Traditional ROI: 0.73%
Whimbrel Plan Middletown, DE Whimbrel Plan, Middletown, DE 19709 \| Single Family Residential	3 beds \| 2 baths \| 2,544 sq.ft.	$645,400	Airbnb cash on cash: N/A Traditional cash on cash: 1.97% Airbnb Rental Income: $null Traditional Rental Income: $2223 Airbnb ROI: N/A Traditional ROI: 1.97%
Waterford Plan Middletown, DE Waterford Plan, Middletown, DE 19709 \| Single Family Residential	4 beds \| 3 baths \| 4,810 sq.ft.	$780,400	Airbnb cash on cash: N/A Traditional cash on cash: 1.72% Airbnb Rental Income: $null Traditional Rental Income: $2480 Airbnb ROI: N/A Traditional ROI: 1.72%
Brady Plan Middletown, DE Brady Plan, Middletown, DE 19709 \| Single Family Residential	4 beds \| 2 baths \| 4,250 sq.ft.	$745,400	Airbnb cash on cash: N/A Traditional cash on cash: 1.23% Airbnb Rental Income: $null Traditional Rental Income: $2034 Airbnb ROI: N/A Traditional ROI: 1.23%
Kingfisher Plan Middletown, DE Kingfisher Plan, Middletown, DE 19709 \| Single Family Residential	3 beds \| 2 baths \| 3,531 sq.ft.	$705,400	Airbnb cash on cash: N/A Traditional cash on cash: 0.82% Airbnb Rental Income: $null Traditional Rental Income: $1664 Airbnb ROI: N/A Traditional ROI: 0.82%
1400 Von Drais St Middletown, DE 1400 Von Drais St, Middletown, DE 19709 \| Single Family Residential	4 beds \| 2 baths \| 2,716 sq.ft.	$749,999	Airbnb cash on cash: N/A Traditional cash on cash: 1.88% Airbnb Rental Income: $null Traditional Rental Income: $2501 Airbnb ROI: N/A Traditional ROI: 1.88%
Aberdeen II Plan Middletown, DE Aberdeen II Plan, Middletown, DE 19709 \| Single Family Residential	3 beds \| 2 baths \| 2,148 sq.ft.	$547,990	Airbnb cash on cash: N/A Traditional cash on cash: 2.53% Airbnb Rental Income: $null Traditional Rental Income: $2189 Airbnb ROI: N/A Traditional ROI: 2.53%
Carver Plan Middletown, DE Carver Plan, Middletown, DE 19709 \| Single Family Residential	2 beds \| 2 baths \| 2,493 sq.ft.	$648,990	Airbnb cash on cash: -0.78% Traditional cash on cash: 1.59% Airbnb Rental Income: $910 Traditional Rental Income: $2004 Airbnb ROI: -0.78% Traditional ROI: 1.59%
1102 Highland St Middletown, DE 1102 Highland St, Middletown, DE 19709 \| Single Family Residential	2 beds \| 2 baths \| 1,715 sq.ft.	$504,900	Airbnb cash on cash: -0.56% Traditional cash on cash: 3.1% Airbnb Rental Income: $910 Traditional Rental Income: $2296 Airbnb ROI: -0.56% Traditional ROI: 3.1%
Omaha Plan Middletown, DE	4 beds \| 3 baths \| 2,772 sq.ft.	$657,990	Airbnb cash on cash: N/A Traditional cash on cash: 2.68% Airbnb Rental Income: $null Traditional Rental Income: $2702 Airbnb ROI: N/A Traditional ROI: 2.68%

Your search for investment property begins and ends here

Single Family Homes for Sale in Middletown, DE

1920 E ARISTOTLE AVE

Middletown, DE

4 beds | 4 baths | N/A

$619,900

Airbnb cash on cash: N/A

Traditional cash on cash: 5.33%

Airbnb Rental Income: $null

Traditional Rental Income: $4191

Airbnb ROI: N/A

Traditional ROI: 5.33%

627 Nesting Ln

Middletown, DE

8 beds | 4 baths | 5,950 sq.ft.

$850,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.24%

Airbnb Rental Income: $null

Traditional Rental Income: $3874

Airbnb ROI: N/A

Traditional ROI: 3.24%

113 CRAWFORD ST

Middletown, DE

3 beds | 2 baths | N/A

$350,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.33%

Airbnb Rental Income: $null

Traditional Rental Income: $2138

Airbnb ROI: N/A

Traditional ROI: 4.33%

32 W MINGLEWOOD DRIVE

Middletown, DE

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

$525,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.43%

Airbnb Rental Income: $null

Traditional Rental Income: $2750

Airbnb ROI: N/A

Traditional ROI: 3.43%

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%

130 S Lores Landing Rd

Middletown, DE

4 beds | 2 baths | 2,900 sq.ft.

$628,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.7%

Airbnb Rental Income: $null

Traditional Rental Income: $2658

Airbnb ROI: N/A

Traditional ROI: 2.7%

103 Westside Ln

Middletown, DE

4 beds | 3 baths | 4,936 sq.ft.

$664,900

Airbnb cash on cash: N/A

Traditional cash on cash: 3.63%

Airbnb Rental Income: $null

Traditional Rental Income: $3448

Airbnb ROI: N/A

Traditional ROI: 3.63%

431 Georgiana Dr

Middletown, DE

5 beds | 3 baths | 4,272 sq.ft.

$765,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3%

Airbnb Rental Income: $null

Traditional Rental Income: $3425

Airbnb ROI: N/A