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 25 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%
138 GREEN FOREST DRIVE Middletown, DE Welcome to 138 Green Forest Drive, a beautifully appointed 4&5 bedroom home offering gener...	4 beds \| 4 baths \| 5,877 sq.ft.	$774,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.11% Airbnb Rental Income: $null Traditional Rental Income: $4165 Airbnb ROI: N/A Traditional ROI: 4.11%
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%
404 PAPER BIRCH Street 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: -1.48% Traditional cash on cash: 2.21% Airbnb Rental Income: $857 Traditional Rental Income: $2487 Airbnb ROI: -1.48% Traditional ROI: 2.21%
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	$609,000	Airbnb cash on cash: N/A Traditional cash on cash: 3% Airbnb Rental Income: $null Traditional Rental Income: $2719 Airbnb ROI: N/A Traditional ROI: 3%
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%
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	$359,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.97% Airbnb Rental Income: $null Traditional Rental Income: $1696 Airbnb ROI: N/A Traditional ROI: 2.97%
15 GOLDEN RAINTREE Court 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%
19 GOLDEN RAINTREE Court 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%
4116 LAUGHTON LANE Middletown, DE Welcome to resort-style living in the highly sought-after Village of Bayberry South! Perfe...	4 beds \| 3 baths \| 2,650 sq.ft.	$565,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.93% Airbnb Rental Income: $null Traditional Rental Income: $2810 Airbnb ROI: N/A Traditional ROI: 2.93%
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 MOTIVATED SELLER SAYS BRING ALL REASONABLE OFFERS!!Discover the charm of this stunning tra...	4 beds \| 3 baths \| N/A	$585,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.18% Airbnb Rental Income: $null Traditional Rental Income: $3365 Airbnb ROI: N/A Traditional ROI: 4.18%
13 GOLDEN RAINTREE Court Middletown, DE This is a To-Be-Built Home. The Dorchester is a thoughtfully designed one-story floorplan ...	2 beds \| 3 baths \| 1,859 sq.ft.	$543,990	Airbnb cash on cash: -1.25% Traditional cash on cash: 2.87% Airbnb Rental Income: $857 Traditional Rental Income: $2619 Airbnb ROI: -1.25% Traditional ROI: 2.87%
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	$400,000	Airbnb cash on cash: -0.7% Traditional cash on cash: 3.25% Airbnb Rental Income: $857 Traditional Rental Income: $2006 Airbnb ROI: -0.7% Traditional ROI: 3.25%
420 WINTERBERRY DR Middletown, DE This home in the beautiful over 55 Community of Four Seasons at Silver Maple was construct...	3 beds \| 3 baths \| N/A	$560,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.89% Airbnb Rental Income: $null Traditional Rental Income: $2564 Airbnb ROI: N/A Traditional ROI: 2.89%
400 TOPIARY Lane Middletown, DE Conveniently situated in the neighborhood, 400 Topiary Lane is now for sale. Take advantag...	2 beds \| 2 baths \| 2,100 sq.ft.	$469,900	Airbnb cash on cash: -1.48% Traditional cash on cash: 3.07% Airbnb Rental Income: $857 Traditional Rental Income: $2526 Airbnb ROI: -1.48% Traditional ROI: 3.07%
1229 PIMPERNELL PATH Middletown, DE Welcome to 1229 Pimpernell Path in the desirable neighborhood of Shannon Cove located in t...	5 beds \| 3 baths \| 3,375 sq.ft.	$769,999	Airbnb cash on cash: N/A Traditional cash on cash: 2.66% Airbnb Rental Income: $null Traditional Rental Income: $3340 Airbnb ROI: N/A Traditional ROI: 2.66%
1689 CHOPTANK RD Middletown, DE Nestled in the charming Westside Hunt subdivision, this stunning Colonial home offers a pe...	5 beds \| 5 baths \| N/A	$850,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.87% Airbnb Rental Income: $null Traditional Rental Income: $4627 Airbnb ROI: N/A Traditional ROI: 3.87%
627 CHURCHTOWN ROAD Middletown, DE SELLER HAS REQUESTED THAT ALL HIGHEST, BEST & FINAL OFFERS BE SUBMITTED BY MONDAY, JUNE 29...	3 beds \| 2 baths \| 1,575 sq.ft.	$300,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.1% Airbnb Rental Income: $null Traditional Rental Income: $2164 Airbnb ROI: N/A Traditional ROI: 5.1%

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%

138 GREEN FOREST DRIVE

Middletown, DE

4 beds | 4 baths | 5,877 sq.ft.

$774,900

Airbnb cash on cash: N/A

Traditional cash on cash: 4.11%

Airbnb Rental Income: $null

Traditional Rental Income: $4165

Airbnb ROI: N/A

Traditional ROI: 4.11%

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%

404 PAPER BIRCH Street

Middletown, DE

2 beds | 2 baths | 1,825 sq.ft.

$569,000

Airbnb cash on cash: -1.48%

Traditional cash on cash: 2.21%

Airbnb Rental Income: $857

Traditional Rental Income: $2487

Airbnb ROI: -1.48%

Traditional ROI: 2.21%

118 AIRMONT DR

Middletown, DE

5 beds | 2 baths | N/A

$609,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3%

Airbnb Rental Income: $null

Traditional Rental Income: $2719

Airbnb ROI: N/A

Traditional ROI: 3%

632 HARRIER LN

Middletown, DE

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%

8 REDDING CIR

Middletown, DE

3 beds | 2 baths | N/A

$359,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.97%

Airbnb Rental Income: $null

Traditional Rental Income: $1696

Airbnb ROI: N/A

Traditional ROI: 2.97%

15 GOLDEN RAINTREE Court

Middletown, DE

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