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

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
36 Island St South Dennis, MA 36 Island St, South Dennis, MA 02638 \| Single Family Residential	3 beds \| 3 baths \| 2,848 sq.ft.	$1,097,000	Airbnb cash on cash: -0.58% Traditional cash on cash: 1.46% Airbnb Rental Income: $2345 Traditional Rental Income: $3854 Airbnb ROI: -0.58% Traditional ROI: 1.46%
7 Vinland Dr South Dennis, MA Just completed and under 5 miles ( 40 minutes by boat) to Nantucket Sound & the Atlantic O...	3 beds \| 3 baths \| 2,735 sq.ft.	$1,595,000	Airbnb cash on cash: -0.07% Traditional cash on cash: 1.39% Airbnb Rental Income: $2345 Traditional Rental Income: $3934 Airbnb ROI: -0.07% Traditional ROI: 1.39%
194 Main St South Dennis, MA Don't miss this rare opportunity to own 1.67 acres in the Historic District of Dennis. Set...	3 beds \| 2 baths \| 1,164 sq.ft.	$650,000	Airbnb cash on cash: 1.47% Traditional cash on cash: 3.87% Airbnb Rental Income: $2345 Traditional Rental Income: $3223 Airbnb ROI: 1.47% Traditional ROI: 3.87%
171 Searsville Rd South Dennis, MA Imagine the moments you'll capture in this new construction. It began as all beautiful thi...	5 beds \| 4 baths \| 6,174 sq.ft.	$3,399,000	Airbnb cash on cash: -0.16% Traditional cash on cash: 1.09% Airbnb Rental Income: $3589 Traditional Rental Income: $6739 Airbnb ROI: -0.16% Traditional ROI: 1.09%
52 Uncle Bobs Way South Dennis, MA Step into this beautifully renovated 3-bedroom, 1-bath home featuring a stunning open floo...	3 beds \| 1 baths \| 1,056 sq.ft.	$599,900	Airbnb cash on cash: 1.63% Traditional cash on cash: 2.89% Airbnb Rental Income: $2345 Traditional Rental Income: $2470 Airbnb ROI: 1.63% Traditional ROI: 2.89%
293 Main St South Dennis, MA 293 Main St, South Dennis, MA 02660 \| Other	N/A beds \| N/A baths \| N/A	$800,000	Airbnb cash on cash: -0.18% Traditional cash on cash: -0.19% Airbnb Rental Income: $2169 Traditional Rental Income: $1608 Airbnb ROI: -0.18% Traditional ROI: -0.19%
295 Main St South Dennis, MA 295 Main St, South Dennis, MA 02660 \| Other	N/A beds \| N/A baths \| N/A	$2,000,000	Airbnb cash on cash: -1.4% Traditional cash on cash: -1.41% Airbnb Rental Income: $2169 Traditional Rental Income: $1608 Airbnb ROI: -1.4% Traditional ROI: -1.41%
299 Main St South Dennis, MA A truly remarkable Bass River estate, set on an extraordinary 5.11 acres of private waterf...	5 beds \| 4 baths \| 5,814 sq.ft.	$9,500,000	Airbnb cash on cash: -0.83% Traditional cash on cash: -0.42% Airbnb Rental Income: $3589 Traditional Rental Income: $6387 Airbnb ROI: -0.83% Traditional ROI: -0.42%
360 Airline Rd South Dennis, MA 360 Airline Rd, South Dennis, MA 02660 \| Single Family Residential	3 beds \| 1 baths \| 1,596 sq.ft.	$610,000	Airbnb cash on cash: 0.72% Traditional cash on cash: 2.39% Airbnb Rental Income: $2345 Traditional Rental Income: $2716 Airbnb ROI: 0.72% Traditional ROI: 2.39%
7 Pinefield Ln South Dennis, MA Classic Coastal Cape located in the South Dennis Historic Village tucked away on a quiet s...	3 beds \| 2 baths \| 2,027 sq.ft.	$1,050,000	Airbnb cash on cash: 0.37% Traditional cash on cash: 1.34% Airbnb Rental Income: $2345 Traditional Rental Income: $2716 Airbnb ROI: 0.37% Traditional ROI: 1.34%
30 Ashkins Drive South Dennis, MA Enjoy Cape Cod living in this well-maintained 3-bedroom, 1-bath ranch set on a spacious co...	3 beds \| 1 baths \| 924 sq.ft.	$549,000	Airbnb cash on cash: 1.93% Traditional cash on cash: 2.97% Airbnb Rental Income: $2345 Traditional Rental Income: $2301 Airbnb ROI: 1.93% Traditional ROI: 2.97%
3 Pinefield Lane South Dennis, MA Come and see this tastefully renovated home for yourself. 3 Pinefield has undergone a subs...	4 beds \| 4 baths \| 2,660 sq.ft.	$1,495,000	Airbnb cash on cash: 0.38% Traditional cash on cash: 2.05% Airbnb Rental Income: $3090 Traditional Rental Income: $4713 Airbnb ROI: 0.38% Traditional ROI: 2.05%
6 Hawthorn Street South Dennis, MA $30,000 Price Reduction on this South Dennis ranch style home featuring three bedrooms, tw...	3 beds \| 2 baths \| 1,192 sq.ft.	$649,900	Airbnb cash on cash: 1.36% Traditional cash on cash: 3.22% Airbnb Rental Income: $2345 Traditional Rental Income: $2892 Airbnb ROI: 1.36% Traditional ROI: 3.22%
29 Highland Street South Dennis, MA MOVE-IN READY turnkey property in a highly sought after location. ALL furnishings included...	2 beds \| 1 baths \| 908 sq.ft.	$639,900	Airbnb cash on cash: 1.13% Traditional cash on cash: 2.21% Airbnb Rental Income: $2048 Traditional Rental Income: $2164 Airbnb ROI: 1.13% Traditional ROI: 2.21%
1 Norseman Drive South Dennis, MA PRICE ADJUSTMENT - Welcome to 1 Norsman Drive in South Dennis! Now offered at a compelling...	3 beds \| 2 baths \| 1,054 sq.ft.	$545,000	Airbnb cash on cash: 1.87% Traditional cash on cash: 3.89% Airbnb Rental Income: $2345 Traditional Rental Income: $2791 Airbnb ROI: 1.87% Traditional ROI: 3.89%
432 Old Chatham Road unit: 403 #403 South Dennis, MA Affordable Cape Cod ownership starts here. This well-kept 1-bedroom, 1-bath condo at Cape ...	1 beds \| 1 baths \| 760 sq.ft.	$244,900	Airbnb cash on cash: 3.82% Traditional cash on cash: 6.35% Airbnb Rental Income: $1797 Traditional Rental Income: $1896 Airbnb ROI: 3.82% Traditional ROI: 6.35%
62 Old Fish House Road South Dennis, MA Discover the timeless Cape Cod lifestyle at this classic seasonal cottage just steps away ...	3 beds \| 1 baths \| 788 sq.ft.	$459,000	Airbnb cash on cash: 2.53% Traditional cash on cash: 3.7% Airbnb Rental Income: $2345 Traditional Rental Income: $2269 Airbnb ROI: 2.53% Traditional ROI: 3.7%
17 Margate Lane South Dennis, MA Well-maintained split-level home on a corner lot in a quiet, established neighborhood. Thi...	3 beds \| 2 baths \| 1,550 sq.ft.	$750,000	Airbnb cash on cash: 0.99% Traditional cash on cash: 2.93% Airbnb Rental Income: $2345 Traditional Rental Income: $3119 Airbnb ROI: 0.99% Traditional ROI: 2.93%
241 Old Bass River Road South Dennis, MA Charming 2 bedroom + den, ranch-style home set on a desirable corner lot in South Dennis, ...	2 beds \| 1 baths \| 1,120 sq.ft.	$475,000	Airbnb cash on cash: 1.81% Traditional cash on cash: 3.69% Airbnb Rental Income: $2048 Traditional Rental Income: $2354 Airbnb ROI: 1.81% Traditional ROI: 3.69%
144 Forest Pines Drive South Dennis, MA It is all about the location. Lovely northside neighborhood. This home needs new owners to...	2 beds \| 2 baths \| 1,380 sq.ft.	$560,000	Airbnb cash on cash: 1.25% Traditional cash on cash: 3.75% Airbnb Rental Income: $2048 Traditional Rental Income: $2825 Airbnb ROI: 1.25% Traditional ROI: 3.75%

Real Estate investment in South-dennis, MA

There are 22 properties for sale in the city of South Dennis . The median list price in South Dennis is $639,900 and the average price per square foot is $338. In March 2026, the average monthly cash on cash return in South Dennis is 3.00%. The average monthly rental income in South Dennis is $2,791.

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

There are 22 investment properties available for sale in South-dennis.

In 2026, 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 $2,791.

Your search for investment property begins and ends here

Investment Property for Sale in South Dennis, MA

36 Island St

South Dennis, MA

3 beds | 3 baths | 2,848 sq.ft.

$1,097,000

Airbnb cash on cash: -0.58%

Traditional cash on cash: 1.46%

Airbnb Rental Income: $2345

Traditional Rental Income: $3854

Airbnb ROI: -0.58%

Traditional ROI: 1.46%

7 Vinland Dr

South Dennis, MA

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

$1,595,000

Airbnb cash on cash: -0.07%

Traditional cash on cash: 1.39%

Airbnb Rental Income: $2345

Traditional Rental Income: $3934

Airbnb ROI: -0.07%

Traditional ROI: 1.39%

194 Main St

South Dennis, MA

3 beds | 2 baths | 1,164 sq.ft.

$650,000

Airbnb cash on cash: 1.47%

Traditional cash on cash: 3.87%

Airbnb Rental Income: $2345

Traditional Rental Income: $3223

Airbnb ROI: 1.47%

Traditional ROI: 3.87%

171 Searsville Rd

South Dennis, MA

5 beds | 4 baths | 6,174 sq.ft.

$3,399,000

Airbnb cash on cash: -0.16%

Traditional cash on cash: 1.09%

Airbnb Rental Income: $3589

Traditional Rental Income: $6739

Airbnb ROI: -0.16%

Traditional ROI: 1.09%

52 Uncle Bobs Way

South Dennis, MA

3 beds | 1 baths | 1,056 sq.ft.

$599,900

Airbnb cash on cash: 1.63%

Traditional cash on cash: 2.89%

Airbnb Rental Income: $2345

Traditional Rental Income: $2470

Airbnb ROI: 1.63%

Traditional ROI: 2.89%

293 Main St

South Dennis, MA

N/A beds | N/A baths | N/A

$800,000

Airbnb cash on cash: -0.18%

Traditional cash on cash: -0.19%

Airbnb Rental Income: $2169

Traditional Rental Income: $1608

Airbnb ROI: -0.18%

Traditional ROI: -0.19%

295 Main St

South Dennis, MA

N/A beds | N/A baths | N/A

$2,000,000

Airbnb cash on cash: -1.4%

Traditional cash on cash: -1.41%

Airbnb Rental Income: $2169

Traditional Rental Income: $1608

Airbnb ROI: -1.4%

Traditional ROI: -1.41%

299 Main St

South Dennis, MA

5 beds | 4 baths | 5,814 sq.ft.

$9,500,000

Airbnb cash on cash: -0.83%

Traditional cash on cash: -0.42%

Airbnb Rental Income: $3589

Traditional Rental Income: $6387

Airbnb ROI: -0.83%