Real Estate Investment Properties for Sale in South Dennis, MA

Looking for investment property in South Dennis, MA with high ROI ?

Explore a variety of short-term homes & houses in South Dennis, MA. Invest wisely with VRBO & South Dennis, MA 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 South Dennis, MA

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
7 Vinland Drive South Dennis, MA Cape Cod new construction with access to Nantucket Sound & the Atlantic Ocean. Welcome to ...	3 beds \| 3 baths \| 2,735 sq.ft.	$1,850,000	Airbnb cash on cash: -0.15% Traditional cash on cash: 1.07% Airbnb Rental Income: $2432 Traditional Rental Income: $3934 Airbnb ROI: -0.15% Traditional ROI: 1.07%
30 Captain Nickerson Lane South Dennis, MA Securing the Chapter 91 dock permit offers a unique chance to own a stunning waterfront pr...	4 beds \| 3 baths \| 2,050 sq.ft.	$1,995,000	Airbnb cash on cash: -0.09% Traditional cash on cash: 0.97% Airbnb Rental Income: $2994 Traditional Rental Income: $4270 Airbnb ROI: -0.09% Traditional ROI: 0.97%
42 Barn Swallow Lane South Dennis, MA Tucked away at the end of a Quiet Cul-de-Sac, this Meticulously Updated 3 BR/2 Bath Ranch-...	3 beds \| 2 baths \| 1,532 sq.ft.	$795,000	Airbnb cash on cash: 0.99% Traditional cash on cash: 2.48% Airbnb Rental Income: $2432 Traditional Rental Income: $2942 Airbnb ROI: 0.99% Traditional ROI: 2.48%
432 Old Chatham Road unit: 105 #105 South Dennis, MA Now's the perfect time to make Cape Cod your home-welcome to Cape Colony Condominiums, a q...	2 beds \| 1 baths \| 1,023 sq.ft.	$340,000	Airbnb cash on cash: 1.84% Traditional cash on cash: 2.13% Airbnb Rental Income: $2242 Traditional Rental Income: $1770 Airbnb ROI: 1.84% Traditional ROI: 2.13%
27 Openfield Road South Dennis, MA Behold this magnificent custom-built home, nestled on over an acre of land. Boasting 4 bed...	4 beds \| 4 baths \| 3,502 sq.ft.	$2,799,900	Airbnb cash on cash: -0.37% Traditional cash on cash: 0.5% Airbnb Rental Income: $2994 Traditional Rental Income: $4586 Airbnb ROI: -0.37% Traditional ROI: 0.5%
64 Old Fish House Road South Dennis, MA Nestled in an exceptional location just two minutes from Little Beach on Kelley's Bay, thi...	4 beds \| 3 baths \| 3,136 sq.ft.	$995,000	Airbnb cash on cash: 0.89% Traditional cash on cash: 2.89% Airbnb Rental Income: $2994 Traditional Rental Income: $4156 Airbnb ROI: 0.89% Traditional ROI: 2.89%
25 Skerry Road South Dennis, MA Back on Market as buyer financing fell through. What a GREAT PRICE on this delightful home...	2 beds \| 1 baths \| 864 sq.ft.	$529,000	Airbnb cash on cash: 1.85% Traditional cash on cash: 2.87% Airbnb Rental Income: $2242 Traditional Rental Income: $2183 Airbnb ROI: 1.85% Traditional ROI: 2.87%
261 Old Chatham Road South Dennis, MA BACK ON MARKET WITH RENOVATIONS AND MOVE-IN CONDITION! Welcome to this delightful 3-bedroo...	3 beds \| 2 baths \| 1,152 sq.ft.	$569,900	Airbnb cash on cash: 1.89% Traditional cash on cash: 3.81% Airbnb Rental Income: $2432 Traditional Rental Income: $2860 Airbnb ROI: 1.89% Traditional ROI: 3.81%
28 Thorwald Drive South Dennis, MA Charming Cape Cod ranch boasting 3 sunny bedrooms, 1 main bathroom and ample built -in sto...	3 beds \| 1 baths \| 1,056 sq.ft.	$524,900	Airbnb cash on cash: 2.2% Traditional cash on cash: 3.63% Airbnb Rental Income: $2432 Traditional Rental Income: $2537 Airbnb ROI: 2.2% Traditional ROI: 3.63%
9 Bayberry Lane South Dennis, MA Walk to neighborhood beach. Centrally located 2-bedroom home between the north & south sid...	2 beds \| 1 baths \| 606 sq.ft.	$494,500	Airbnb cash on cash: 2.15% Traditional cash on cash: 2.81% Airbnb Rental Income: $2242 Traditional Rental Income: $1984 Airbnb ROI: 2.15% Traditional ROI: 2.81%
344 Mayfair Road South Dennis, MA Beautifully custom-built Ranch set on nearly an acre in the desirable town of Dennis. This...	2 beds \| 2 baths \| 1,822 sq.ft.	$829,900	Airbnb cash on cash: 0.61% Traditional cash on cash: 2.4% Airbnb Rental Income: $2242 Traditional Rental Income: $3064 Airbnb ROI: 0.61% Traditional ROI: 2.4%
26 Willowford Road South Dennis, MA Situated at the end of a quiet, tree-lined lane in one of Dennis' most coveted enclaves, t...	4 beds \| 5 baths \| 2,919 sq.ft.	$4,650,000	Airbnb cash on cash: -0.7% Traditional cash on cash: 0.3% Airbnb Rental Income: $2994 Traditional Rental Income: $6614 Airbnb ROI: -0.7% Traditional ROI: 0.3%
10 Devonshire Lane South Dennis, MA Something is always in bloom at 10 Devonshire! This pretty saltbox colonial located in the...	3 beds \| 2 baths \| 1,320 sq.ft.	$579,900	Airbnb cash on cash: 1.9% Traditional cash on cash: 3.94% Airbnb Rental Income: $2432 Traditional Rental Income: $2947 Airbnb ROI: 1.9% Traditional ROI: 3.94%
33 Old Fish House Road unit: A1 #A1 South Dennis, MA Wake up to sweeping water views and enjoy stunning sunsets from this updated 3-bed, 2.5-ba...	3 beds \| 3 baths \| 2,077 sq.ft.	$938,000	Airbnb cash on cash: -0.13% Traditional cash on cash: 2.41% Airbnb Rental Income: $2432 Traditional Rental Income: $4052 Airbnb ROI: -0.13% Traditional ROI: 2.41%
6 Hawthorn Street South Dennis, MA This South Dennis ranch style home features three bedrooms, two full baths, living room wi...	3 beds \| 2 baths \| 1,193 sq.ft.	$679,900	Airbnb cash on cash: 1.38% Traditional cash on cash: 3.04% Airbnb Rental Income: $2432 Traditional Rental Income: $2892 Airbnb ROI: 1.38% Traditional ROI: 3.04%
15 Sallys Way South Dennis, MA Charming Ranch with Deeded Follins Pond Access - Cape Cod Living at Its Best! Set on a gen...	3 beds \| 1 baths \| 1,056 sq.ft.	$599,900	Airbnb cash on cash: 1.75% Traditional cash on cash: 2.96% Airbnb Rental Income: $2432 Traditional Rental Income: $2511 Airbnb ROI: 1.75% Traditional ROI: 2.96%
138 Center Street South Dennis, MA This once in a lifetime opportunity to own a large sub dividable lot currently being used ...	3 beds \| 2 baths \| 1,212 sq.ft.	$895,000	Airbnb cash on cash: 0.84% Traditional cash on cash: 2.2% Airbnb Rental Income: $2432 Traditional Rental Income: $2976 Airbnb ROI: 0.84% Traditional ROI: 2.2%
15 Alexander Drive South Dennis, MA Classic Cape Cottage! Cherished by one family, over 50+ yrs, now ready for a new chapter. ...	2 beds \| 1 baths \| 760 sq.ft.	$489,000	Airbnb cash on cash: 2.16% Traditional cash on cash: 3.19% Airbnb Rental Income: $2242 Traditional Rental Income: $2147 Airbnb ROI: 2.16% Traditional ROI: 3.19%
29 Highland Street South Dennis, MA A MUST SEE! This is a unique, one-of-a-kind property you won't want to miss! This custom h...	2 beds \| 1 baths \| 908 sq.ft.	$719,900	Airbnb cash on cash: 1.13% Traditional cash on cash: 1.86% Airbnb Rental Income: $2242 Traditional Rental Income: $2164 Airbnb ROI: 1.13% Traditional ROI: 1.86%
15 Captain Jud Road South Dennis, MA Tucked away in a great South Dennis location, this spacious home is designed for both comf...	3 beds \| 3 baths \| 1,368 sq.ft.	$699,000	Airbnb cash on cash: 1.24% Traditional cash on cash: 3.21% Airbnb Rental Income: $2432 Traditional Rental Income: $3125 Airbnb ROI: 1.24% Traditional ROI: 3.21%
18 Rangeley Lane South Dennis, MA Spacious and charming living awaits you at 18 Rangeley Lane! Situated at the end of a priv...	3 beds \| 2 baths \| 1,888 sq.ft.	$649,900	Airbnb cash on cash: 1.44% Traditional cash on cash: 3.9% Airbnb Rental Income: $2432 Traditional Rental Income: $3330 Airbnb ROI: 1.44% Traditional ROI: 3.9%
16 Dunstable Cross Road South Dennis, MA Your home should be a haven of serenity and once you step inside 16 Dunstable Cross Road, ...	2 beds \| 1 baths \| 1,086 sq.ft.	$599,000	Airbnb cash on cash: 1.46% Traditional cash on cash: 2.54% Airbnb Rental Income: $2242 Traditional Rental Income: $2287 Airbnb ROI: 1.46% Traditional ROI: 2.54%
46 Jays Drive South Dennis, MA Welcome to 46 Jays Drive, a stunning newer build in South Dennis showcasing timeless Cape ...	3 beds \| 3 baths \| 2,512 sq.ft.	$1,399,000	Airbnb cash on cash: -0.07% Traditional cash on cash: 1.52% Airbnb Rental Income: $2432 Traditional Rental Income: $3905 Airbnb ROI: -0.07% Traditional ROI: 1.52%

Real Estate investment in South-dennis, MA

There are 23 properties for sale in the city of South Dennis . The median list price in South Dennis is $679,900 and the average price per square foot is $434. In September 2025, the average monthly cash on cash return in South Dennis is 3.00%. The average monthly rental income in South Dennis is $2,942.

South-dennis, MA Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 23 investment properties available for sale in South-dennis.

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

The ROI for Long-Term is higher than the Short-Term in South-dennis with average rental income of $2,942.

Your search for investment property begins and ends here

Investment Property for Sale in South Dennis, MA

7 Vinland Drive

South Dennis, MA

3 beds | 3 baths | 2,735 sq.ft.

$1,850,000

Airbnb cash on cash: -0.15%

Traditional cash on cash: 1.07%

Airbnb Rental Income: $2432

Traditional Rental Income: $3934

Airbnb ROI: -0.15%

Traditional ROI: 1.07%

30 Captain Nickerson Lane

South Dennis, MA

4 beds | 3 baths | 2,050 sq.ft.

$1,995,000

Airbnb cash on cash: -0.09%

Traditional cash on cash: 0.97%

Airbnb Rental Income: $2994

Traditional Rental Income: $4270

Airbnb ROI: -0.09%

Traditional ROI: 0.97%

42 Barn Swallow Lane

South Dennis, MA

3 beds | 2 baths | 1,532 sq.ft.

$795,000

Airbnb cash on cash: 0.99%

Traditional cash on cash: 2.48%

Airbnb Rental Income: $2432

Traditional Rental Income: $2942

Airbnb ROI: 0.99%

Traditional ROI: 2.48%

432 Old Chatham Road unit: 105 #105

South Dennis, MA

2 beds | 1 baths | 1,023 sq.ft.

$340,000

Airbnb cash on cash: 1.84%

Traditional cash on cash: 2.13%

Airbnb Rental Income: $2242

Traditional Rental Income: $1770

Airbnb ROI: 1.84%

Traditional ROI: 2.13%

27 Openfield Road

South Dennis, MA

4 beds | 4 baths | 3,502 sq.ft.

$2,799,900

Airbnb cash on cash: -0.37%

Traditional cash on cash: 0.5%

Airbnb Rental Income: $2994

Traditional Rental Income: $4586

Airbnb ROI: -0.37%

Traditional ROI: 0.5%

64 Old Fish House Road

South Dennis, MA

4 beds | 3 baths | 3,136 sq.ft.

$995,000

Airbnb cash on cash: 0.89%

Traditional cash on cash: 2.89%

Airbnb Rental Income: $2994

Traditional Rental Income: $4156

Airbnb ROI: 0.89%

Traditional ROI: 2.89%

25 Skerry Road

South Dennis, MA

2 beds | 1 baths | 864 sq.ft.

$529,000

Airbnb cash on cash: 1.85%

Traditional cash on cash: 2.87%

Airbnb Rental Income: $2242

Traditional Rental Income: $2183

Airbnb ROI: 1.85%

Traditional ROI: 2.87%

261 Old Chatham Road

South Dennis, MA

3 beds | 2 baths | 1,152 sq.ft.

$569,900

Airbnb cash on cash: 1.89%

Traditional cash on cash: 3.81%

Airbnb Rental Income: $2432

Traditional Rental Income: $2860

Airbnb ROI: 1.89%