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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
310 MAIN STREET Cheswold, DE A beautifully refreshed and updated home now available at 310 Main Street in Cheswold. Loc...	3 beds \| 2 baths \| 1,344 sq.ft.	$320,000	Airbnb cash on cash: 5.03% Traditional cash on cash: 6.66% Airbnb Rental Income: $2673 Traditional Rental Income: $2530 Airbnb ROI: 5.03% Traditional ROI: 6.66%
Investment Properties for Sale in Other Cities of Delaware
24289 BLUE CRAB AVE #241 Millsboro , DE Welcome to 24289 Blue Crab Ave, located in the resort style community of The Peninsula on ...	3 beds \| 3 baths \| N/A	$520,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.92% Airbnb Rental Income: $null Traditional Rental Income: $2705 Airbnb ROI: N/A Traditional ROI: 3.92%
712 EAST LANE Milford , DE NO HOA! Bring your BOATS, RV, BUILD A POLE BARN! Welcome to North Shores on Haven Lake-one...	4 beds \| 3 baths \| 2,424 sq.ft.	$469,999	Airbnb cash on cash: N/A Traditional cash on cash: 6.28% Airbnb Rental Income: $null Traditional Rental Income: $3409 Airbnb ROI: N/A Traditional ROI: 6.28%
203 S GRAY AVENUE Wilmington , DE This adorable two-bedroom one-bath home in Colonial Heights is move-in ready! Original har...	2 beds \| 1 baths \| 875 sq.ft.	$239,900	Airbnb cash on cash: 4.1% Traditional cash on cash: 5.23% Airbnb Rental Income: $1864 Traditional Rental Income: $1622 Airbnb ROI: 4.1% Traditional ROI: 5.23%
35517 BONAIRE DRIVE Rehoboth Beach , DE Introducing 35517 Bonaire Dr This M/I Home showcase single level 3070 sq ft home is situat...	3 beds \| 3 baths \| 3,070 sq.ft.	$829,900	Airbnb cash on cash: 0.37% Traditional cash on cash: 2.2% Airbnb Rental Income: $2139 Traditional Rental Income: $3013 Airbnb ROI: 0.37% Traditional ROI: 2.2%
34341 SUMMERLYN DRIVE #312 Lewes , DE Welcome to this beautifully updated 3-bedroom, 2-bath, single-level condominium in the des...	3 beds \| 2 baths \| 1,560 sq.ft.	$399,900	Airbnb cash on cash: 3.22% Traditional cash on cash: 4.76% Airbnb Rental Income: $2313 Traditional Rental Income: $2315 Airbnb ROI: 3.22% Traditional ROI: 4.76%
28941 WHALER LANE Frankford , DE Welcome to this stunning 5 bedroom, 4-bathroom home nestled within the prestigious communi...	5 beds \| 4 baths \| 3,383 sq.ft.	$735,000	Airbnb cash on cash: -0.6% Traditional cash on cash: 5.07% Airbnb Rental Income: $1227 Traditional Rental Income: $4722 Airbnb ROI: -0.6% Traditional ROI: 5.07%
5 HILLSIDE AVENUE Frederica , DE Dont miss out on this 5-year-old gem of a home, on a quiet street in Frederica! Recently b...	3 beds \| 2 baths \| 1,440 sq.ft.	$290,000	Airbnb cash on cash: 3.35% Traditional cash on cash: 7.08% Airbnb Rental Income: $1859 Traditional Rental Income: $2380 Airbnb ROI: 3.35% Traditional ROI: 7.08%
34899 PRESERVE LANE Dagsboro , DE Nestled in the charming community of The Preserve at Irons Landing, this great home offers...	3 beds \| 3 baths \| 2,111 sq.ft.	$485,000	Airbnb cash on cash: 1.4% Traditional cash on cash: 4.55% Airbnb Rental Income: $1864 Traditional Rental Income: $2797 Airbnb ROI: 1.4% Traditional ROI: 4.55%
31530 WHITECLAY DRIVE Millville , DE Welcome to this exceptional former model home built by Gulfstream Development, perfectly s...	4 beds \| 3 baths \| 2,690 sq.ft.	$615,000	Airbnb cash on cash: 1.28% Traditional cash on cash: 4.09% Airbnb Rental Income: $2179 Traditional Rental Income: $3243 Airbnb ROI: 1.28% Traditional ROI: 4.09%
36258 WATERLEAF WAY Selbyville , DE Nestled in the serene Bayside community, this exquisite twin semi-detached home offers a l...	3 beds \| 3 baths \| 2,315 sq.ft.	$729,000	Airbnb cash on cash: -0.77% Traditional cash on cash: 2.82% Airbnb Rental Income: $1119 Traditional Rental Income: $3187 Airbnb ROI: -0.77% Traditional ROI: 2.82%
184 EDGE AVE New Castle , DE Welcome to one floor living. This three bdrm, one bath home is move in ready. Freshly pai...	3 beds \| 1 baths \| N/A	$280,000	Airbnb cash on cash: 2.59% Traditional cash on cash: 4.66% Airbnb Rental Income: $1683 Traditional Rental Income: $1758 Airbnb ROI: 2.59% Traditional ROI: 4.66%
125 E CLARENDON DRIVE Smyrna , DE Welcome to AshlandSmyrnas sought-after 55+ community offering quality Wilkinson-built home...	2 beds \| 2 baths \| 1,466 sq.ft.	$349,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.1% Airbnb Rental Income: $null Traditional Rental Income: $1713 Airbnb ROI: N/A Traditional ROI: 3.1%
156 EAST SIDE DR Rehoboth Beach , DE Welcome home to 156 East Side Drive, Rehoboth Beach Yacht and Country Club, featuring a go...	4 beds \| 6 baths \| N/A	$2,950,000	Airbnb cash on cash: -0.55% Traditional cash on cash: -0.05% Airbnb Rental Income: $2187 Traditional Rental Income: $2982 Airbnb ROI: -0.55% Traditional ROI: -0.05%
152 TYWYN DRIVE Middletown , DE Check out this beautiful and well-kept 5-bedroom, 3.5-bath home in the popular Preserves a...	5 beds \| 4 baths \| 4,797 sq.ft.	$665,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.19% Airbnb Rental Income: $null Traditional Rental Income: $4468 Airbnb ROI: N/A Traditional ROI: 5.19%
31828 MILL RUN DRIVE Ocean View , DE Coastal living at its finest! This beautifully updated 3-bedroom, 2-bath home is tucked aw...	3 beds \| 2 baths \| 1,250 sq.ft.	$419,900	Airbnb cash on cash: 1.72% Traditional cash on cash: 4.34% Airbnb Rental Income: $1744 Traditional Rental Income: $2293 Airbnb ROI: 1.72% Traditional ROI: 4.34%

Real Estate investment in Cheswold, DE

There are 1 properties for sale in the city of Cheswold . The median list price in Cheswold is $320,000 and the average price per square foot is $238. In September 2025, the average monthly cash on cash return in Cheswold is 7.00%. The average monthly rental income in Cheswold is $2,530.

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

There are 1 investment properties available for sale in Cheswold.

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

The ROI for Long-Term is higher than the Short-Term in Cheswold with average rental income of $2,530.

Your search for investment property begins and ends here

Investment Property for Sale in Cheswold, DE

310 MAIN STREET

Cheswold, DE

3 beds | 2 baths | 1,344 sq.ft.

$320,000

Airbnb cash on cash: 5.03%

Traditional cash on cash: 6.66%

Airbnb Rental Income: $2673

Traditional Rental Income: $2530

Airbnb ROI: 5.03%

Traditional ROI: 6.66%

Investment Properties for Sale in Other Cities of Delaware

Millsboro , DE

3 beds | 3 baths | N/A

$520,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.92%

Airbnb Rental Income: $null

Traditional Rental Income: $2705

Airbnb ROI: N/A

Traditional ROI: 3.92%

Milford , DE

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

$469,999

Airbnb cash on cash: N/A

Traditional cash on cash: 6.28%

Airbnb Rental Income: $null

Traditional Rental Income: $3409

Airbnb ROI: N/A

Traditional ROI: 6.28%

Wilmington , DE

2 beds | 1 baths | 875 sq.ft.

$239,900

Airbnb cash on cash: 4.1%

Traditional cash on cash: 5.23%

Airbnb Rental Income: $1864

Traditional Rental Income: $1622

Airbnb ROI: 4.1%

Traditional ROI: 5.23%

Rehoboth Beach , DE

3 beds | 3 baths | 3,070 sq.ft.

$829,900

Airbnb cash on cash: 0.37%

Traditional cash on cash: 2.2%

Airbnb Rental Income: $2139

Traditional Rental Income: $3013

Airbnb ROI: 0.37%

Traditional ROI: 2.2%

Lewes , DE

3 beds | 2 baths | 1,560 sq.ft.

$399,900

Airbnb cash on cash: 3.22%

Traditional cash on cash: 4.76%

Airbnb Rental Income: $2313

Traditional Rental Income: $2315

Airbnb ROI: 3.22%

Traditional ROI: 4.76%

Frankford , DE

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

$735,000

Airbnb cash on cash: -0.6%

Traditional cash on cash: 5.07%

Airbnb Rental Income: $1227

Traditional Rental Income: $4722

Airbnb ROI: -0.6%

Traditional ROI: 5.07%

Frederica , DE

3 beds | 2 baths | 1,440 sq.ft.

$290,000

Airbnb cash on cash: 3.35%

Traditional cash on cash: 7.08%

Airbnb Rental Income: $1859

Traditional Rental Income: $2380

Airbnb ROI: 3.35%

Traditional ROI: 7.08%

Dagsboro , DE

3 beds | 3 baths | 2,111 sq.ft.

$485,000

Airbnb cash on cash: 1.4%

Traditional cash on cash: 4.55%