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 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%
3 Pinefield Lane South Dennis, MA How can a property really be ''Better than New''? Come and see for yourself. #3 Pinefield ...	4 beds \| N/A 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%
171 Searsville Road South Dennis, MA Imagine the moments you'll capture in this new construction. It began as all beautiful thi...	5 beds \| 6 baths \| 6,174 sq.ft.	$3,500,000	Airbnb cash on cash: -0.19% Traditional cash on cash: 1.03% Airbnb Rental Income: $3589 Traditional Rental Income: $6739 Airbnb ROI: -0.19% Traditional ROI: 1.03%
25 Skerry Road South Dennis, MA BEST Dennis value at this delightful home with a FULL, dry basement with interior access! ...	2 beds \| 1 baths \| 864 sq.ft.	$529,000	Airbnb cash on cash: 1.52% Traditional cash on cash: 2.87% Airbnb Rental Income: $2048 Traditional Rental Income: $2183 Airbnb ROI: 1.52% Traditional ROI: 2.87%
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.	$659,900	Airbnb cash on cash: 1.06% Traditional cash on cash: 2.11% Airbnb Rental Income: $2048 Traditional Rental Income: $2164 Airbnb ROI: 1.06% Traditional ROI: 2.11%
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.	$640,000	Airbnb cash on cash: 1.32% Traditional cash on cash: 3.6% Airbnb Rental Income: $2345 Traditional Rental Income: $3125 Airbnb ROI: 1.32% Traditional ROI: 3.6%
1 Norseman Drive South Dennis, MA Welcome to 1 Norsman Drive in South Dennis-a charming home set in the heart of Dennis, clo...	3 beds \| 2 baths \| 1,054 sq.ft.	$599,000	Airbnb cash on cash: 1.62% Traditional cash on cash: 3.45% Airbnb Rental Income: $2345 Traditional Rental Income: $2791 Airbnb ROI: 1.62% Traditional ROI: 3.45%
15 Trudy Circle South Dennis, MA Look no further for your quintessential Cape Cod home nestled perfectly on this .36 acre p...	3 beds \| 2 baths \| 1,688 sq.ft.	$799,000	Airbnb cash on cash: 0.93% Traditional cash on cash: 2.89% Airbnb Rental Income: $2345 Traditional Rental Income: $3219 Airbnb ROI: 0.93% Traditional ROI: 2.89%
432 Old Chatham Road unit: 403 #403 South Dennis, MA Cape Cod living made easy-own a piece of South Dennis at Cape Colony! This inviting 1-bedr...	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%
432 Old Chatham Road unit: 103 #103 South Dennis, MA Tired of renting? Welcome to an excellent opportunity to own in the heart of South Dennis!...	1 beds \| 1 baths \| 760 sq.ft.	$239,000	Airbnb cash on cash: 3.93% Traditional cash on cash: 6.59% Airbnb Rental Income: $1797 Traditional Rental Income: $1908 Airbnb ROI: 3.93% Traditional ROI: 6.59%
61 Barque Circle South Dennis, MA Custom Built, Gracious Contemporary Traditional w/ First Floor Primary Bedroom on a level ...	3 beds \| N/A baths \| 2,784 sq.ft.	$1,500,000	Airbnb cash on cash: -0.13% Traditional cash on cash: 0.68% Airbnb Rental Income: $2345 Traditional Rental Income: $2906 Airbnb ROI: -0.13% Traditional ROI: 0.68%
360 Center Street South Dennis, MA Live the Cape Cod lifestyle year-round in this 2-bedroom, 2-bath home built in 1993 by Ree...	2 beds \| 2 baths \| 1,199 sq.ft.	$649,000	Airbnb cash on cash: 1.01% Traditional cash on cash: 3.05% Airbnb Rental Income: $2048 Traditional Rental Income: $2751 Airbnb ROI: 1.01% Traditional ROI: 3.05%
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%
153 Bay Ridge Drive South Dennis, MA Charming South Dennis Home with Deeded Beach Rights to Follins Pond! Nestled in a Quiet, Q...	3 beds \| 1 baths \| 828 sq.ft.	$459,900	Airbnb cash on cash: 2.49% Traditional cash on cash: 3.71% Airbnb Rental Income: $2345 Traditional Rental Income: $2292 Airbnb ROI: 2.49% Traditional ROI: 3.71%
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%
2 Hemlock Lane South Dennis, MA Set on a nicely sized, wooded lot, this 3-bedroom, 2-bath ranch offers a rare chance to tr...	3 beds \| 2 baths \| 1,980 sq.ft.	$489,000	Airbnb cash on cash: 2.23% Traditional cash on cash: 5.59% Airbnb Rental Income: $2345 Traditional Rental Income: $3304 Airbnb ROI: 2.23% Traditional ROI: 5.59%

Real Estate investment in South-dennis, MA

There are 17 properties for sale in the city of South Dennis . The median list price in South Dennis is $640,000 and the average price per square foot is $403. In December 2025, 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 17 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 $2,791.

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.

$1,595,000

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%

3 Pinefield Lane

South Dennis, MA

4 beds | N/A 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%

171 Searsville Road

South Dennis, MA

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

$3,500,000

Airbnb cash on cash: -0.19%

Traditional cash on cash: 1.03%

Airbnb Rental Income: $3589

Traditional Rental Income: $6739

Airbnb ROI: -0.19%

Traditional ROI: 1.03%

25 Skerry Road

South Dennis, MA

2 beds | 1 baths | 864 sq.ft.

$529,000

Airbnb cash on cash: 1.52%

Traditional cash on cash: 2.87%

Airbnb Rental Income: $2048

Traditional Rental Income: $2183

Airbnb ROI: 1.52%

Traditional ROI: 2.87%

6 Hawthorn Street

South Dennis, MA

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

2 beds | 1 baths | 908 sq.ft.

$659,900

Airbnb cash on cash: 1.06%

Traditional cash on cash: 2.11%

Airbnb Rental Income: $2048

Traditional Rental Income: $2164

Airbnb ROI: 1.06%

Traditional ROI: 2.11%

15 Captain Jud Road

South Dennis, MA

3 beds | 3 baths | 1,368 sq.ft.

$640,000

Airbnb cash on cash: 1.32%

Traditional cash on cash: 3.6%

Airbnb Rental Income: $2345

Traditional Rental Income: $3125

Airbnb ROI: 1.32%

Traditional ROI: 3.6%

1 Norseman Drive

South Dennis, MA

3 beds | 2 baths | 1,054 sq.ft.

$599,000

Airbnb cash on cash: 1.62%

Traditional cash on cash: 3.45%

Airbnb Rental Income: $2345

Traditional Rental Income: $2791

Airbnb ROI: 1.62%