Real Estate Investment Properties for Sale in Cheswold, DE

Looking for investment property in Cheswold, DE with high ROI ?

Explore a variety of short-term homes & houses in Cheswold, DE. Invest wisely with VRBO & Cheswold, DE Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Investment Property for Sale in Cheswold, DE

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
No properties are listed in Cheswold, Delaware at the moment.
Other Investment Properties for Sale in Delaware
712 EAST Lane Milford , DE NEW PRICE! TREMENDOUS VALUE! Bring your BOATS, RV, BUILD A POLE BARN! Welcome to North Sho...	4 beds \| 3 baths \| 2,424 sq.ft.	$449,999	Airbnb cash on cash: 4.38% Traditional cash on cash: 6.6% Airbnb Rental Income: $3198 Traditional Rental Income: $3409 Airbnb ROI: 4.38% Traditional ROI: 6.6%
938 VANDEVER Avenue Wilmington , DE This charming townhouse seamlessly blends classic character with modern comforts. Spanning...	3 beds \| 2 baths \| 1,325 sq.ft.	$175,000	Airbnb cash on cash: 3.48% Traditional cash on cash: 9.94% Airbnb Rental Income: $1498 Traditional Rental Income: $2136 Airbnb ROI: 3.48% Traditional ROI: 9.94%
502 IVYDALE Road Wilmington , DE ONE LEVEL LIVING! A gorgeous multi-generational home is available in popular Carrcroft Cre...	4 beds \| 3 baths \| 3,100 sq.ft.	$599,000	Airbnb cash on cash: 2.99% Traditional cash on cash: 5.15% Airbnb Rental Income: $3544 Traditional Rental Income: $3977 Airbnb ROI: 2.99% Traditional ROI: 5.15%
129 Union Street Milton , DE Step into history and opportunity in the heart of Downtown Milton! This Victorian-era mixe...	4 beds \| 2 baths \| 2,200 sq.ft.	$450,000	Airbnb cash on cash: 2.42% Traditional cash on cash: 4.88% Airbnb Rental Income: $2354 Traditional Rental Income: $2810 Airbnb ROI: 2.42% Traditional ROI: 4.88%
28941 WHALER Lane Frankford , DE FULLY FURNISHED WITH ACCEPTED OFFER EXPIRES 11/8/2025. (SEE EXCL LIST of personal items) M...	5 beds \| 4 baths \| 3,383 sq.ft.	$699,900	Airbnb cash on cash: -0.44% Traditional cash on cash: 5.37% Airbnb Rental Income: $1339 Traditional Rental Income: $4722 Airbnb ROI: -0.44% Traditional ROI: 5.37%
38341 N MILL Lane unit: 75 #75 Ocean View , DE Welcome to Bayside At Bethany Lakes, an amenity rich waterfront community where coastal li...	3 beds \| 3 baths \| 2,200 sq.ft.	$530,000	Airbnb cash on cash: -0.03% Traditional cash on cash: 3.76% Airbnb Rental Income: $1024 Traditional Rental Income: $2544 Airbnb ROI: -0.03% Traditional ROI: 3.76%
1701 COASTAL HWY #N206 Dewey Beach , DE Beautiful and bright 2 bedroom, 2 bathroom condo is located only 1 block to the Beach in t...	2 beds \| 2 baths \| N/A	$629,000	Airbnb cash on cash: 0.72% Traditional cash on cash: 2.79% Airbnb Rental Income: $1688 Traditional Rental Income: $2433 Airbnb ROI: 0.72% Traditional ROI: 2.79%
36258 WATERLEAF Way Selbyville , DE Welcome to Bayside living at its best! This beautifully designed twin home, built in 2017,...	3 beds \| 3 baths \| 2,315 sq.ft.	$729,000	Airbnb cash on cash: -0.7% Traditional cash on cash: 2.82% Airbnb Rental Income: $1178 Traditional Rental Income: $3187 Airbnb ROI: -0.7% Traditional ROI: 2.82%
29786 PLANTATION LAKES Boulevard Millsboro , DE LOOK NO FURTHER - Tour this beautiful turn-key home in the amenity-rich community of Plant...	3 beds \| 4 baths \| 2,200 sq.ft.	$329,000	Airbnb cash on cash: -0.99% Traditional cash on cash: 7.6% Airbnb Rental Income: $708 Traditional Rental Income: $3056 Airbnb ROI: -0.99% Traditional ROI: 7.6%
504 HEMINGWAY DRIVE HOCKESSIN , DE Welcome to Hickory Hills, a hidden gem nestled in the heart of Hockessin! This charming 4-...	4 beds \| 3 baths \| 2,000 sq.ft.	$457,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.67% Airbnb Rental Income: $null Traditional Rental Income: $2915 Airbnb ROI: N/A Traditional ROI: 4.67%
16 TYRONE AVENUE New Castle , DE Welcome to 16 Tyrone Ave in New Castle! This 3-bedroom, 2-bath Colonial was fully renovate...	3 beds \| 2 baths \| 1,300 sq.ft.	$270,000	Airbnb cash on cash: 1.5% Traditional cash on cash: 6.58% Airbnb Rental Income: $1372 Traditional Rental Income: $2249 Airbnb ROI: 1.5% Traditional ROI: 6.58%
206 S WALNUT ST Milford , DE Step into History, Live in Elegance: Milford's Timeless Victorian Awaits Step into history...	4 beds \| 4 baths \| N/A	$549,500	Airbnb cash on cash: 3.26% Traditional cash on cash: 6.79% Airbnb Rental Income: $3198 Traditional Rental Income: $4291 Airbnb ROI: 3.26% Traditional ROI: 6.79%
1025-UNIT N MADISON Street unit: 109 #109 Wilmington , DE Cozy Condo in Trinity Square North A well-kept condo in Trinity Square North community. Th...	2 beds \| 1 baths \| 1,000 sq.ft.	$159,900	Airbnb cash on cash: 3.9% Traditional cash on cash: 7.19% Airbnb Rental Income: $1525 Traditional Rental Income: $1584 Airbnb ROI: 3.9% Traditional ROI: 7.19%
19185 SANDSTONE Lane Millsboro , DE Discover the charm of this contemporary duplex townhouse in the desirable Retreat at Mills...	3 beds \| 3 baths \| 1,890 sq.ft.	$344,900	Airbnb cash on cash: -0.61% Traditional cash on cash: 7.52% Airbnb Rental Income: $708 Traditional Rental Income: $3036 Airbnb ROI: -0.61% Traditional ROI: 7.52%
35179 SEAPORT Loop Lewes , DE Beautifully maintained and thoughtfully designed, this 2-3 bedroom detached home offers a ...	3 beds \| 3 baths \| 3,918 sq.ft.	$685,000	Airbnb cash on cash: 0.17% Traditional cash on cash: 2.42% Airbnb Rental Income: $1777 Traditional Rental Income: $2726 Airbnb ROI: 0.17% Traditional ROI: 2.42%

Real Estate investment in Cheswold, DE

There are 0 properties for sale in the city of Cheswold . The median list price in Cheswold is $100,000 and the average price per square foot is $128. In October 2025, the average monthly cash on cash return in Cheswold is 12.00%. The average monthly rental income in Cheswold is $1,486.

Cheswold, DE Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 0 investment properties available for sale in Cheswold.

In 2025, the best neighborhood to buy investment property is Cheswold.

The ROI for Short-Term is higher than the Long-Term in Cheswold with average rental income of $1,162.

Your search for investment property begins and ends here

Investment Property for Sale in Cheswold, DE

Other Investment Properties for Sale in Delaware

Milford , DE

4 beds | 3 baths | 2,424 sq.ft.

$449,999

Airbnb cash on cash: 4.38%

Traditional cash on cash: 6.6%

Airbnb Rental Income: $3198

Traditional Rental Income: $3409

Airbnb ROI: 4.38%

Traditional ROI: 6.6%

Wilmington , DE

3 beds | 2 baths | 1,325 sq.ft.

$175,000

Airbnb cash on cash: 3.48%

Traditional cash on cash: 9.94%

Airbnb Rental Income: $1498

Traditional Rental Income: $2136

Airbnb ROI: 3.48%

Traditional ROI: 9.94%

Wilmington , DE

4 beds | 3 baths | 3,100 sq.ft.

$599,000

Airbnb cash on cash: 2.99%

Traditional cash on cash: 5.15%

Airbnb Rental Income: $3544

Traditional Rental Income: $3977

Airbnb ROI: 2.99%

Traditional ROI: 5.15%

Milton , DE

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

$450,000

Airbnb cash on cash: 2.42%

Traditional cash on cash: 4.88%

Airbnb Rental Income: $2354

Traditional Rental Income: $2810

Airbnb ROI: 2.42%

Traditional ROI: 4.88%

Frankford , DE

5 beds | 4 baths | 3,383 sq.ft.

$699,900

Airbnb cash on cash: -0.44%

Traditional cash on cash: 5.37%

Airbnb Rental Income: $1339

Traditional Rental Income: $4722

Airbnb ROI: -0.44%

Traditional ROI: 5.37%

Ocean View , DE

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

$530,000

Airbnb cash on cash: -0.03%

Traditional cash on cash: 3.76%

Airbnb Rental Income: $1024

Traditional Rental Income: $2544

Airbnb ROI: -0.03%

Traditional ROI: 3.76%

Dewey Beach , DE

2 beds | 2 baths | N/A

$629,000

Airbnb cash on cash: 0.72%

Traditional cash on cash: 2.79%

Airbnb Rental Income: $1688

Traditional Rental Income: $2433

Airbnb ROI: 0.72%

Traditional ROI: 2.79%

Selbyville , DE

3 beds | 3 baths | 2,315 sq.ft.

$729,000

Airbnb cash on cash: -0.7%

Traditional cash on cash: 2.82%

Airbnb Rental Income: $1178

Traditional Rental Income: $3187

Airbnb ROI: -0.7%

Traditional ROI: 2.82%

Millsboro , DE

3 beds | 4 baths | 2,200 sq.ft.

$329,000

Airbnb cash on cash: -0.99%

Traditional cash on cash: 7.6%

Airbnb Rental Income: $708