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
36 Old Sailors Way South Dennis, MA Welcome to 36 Old Sailors Way! This adorable ranch style home offers the old Cape Cod Char...	2 beds \| 1 baths \| 624 sq.ft.	$475,000	Airbnb cash on cash: 0.44% Traditional cash on cash: 3% Airbnb Rental Income: $1265 Traditional Rental Income: $2004 Airbnb ROI: 0.44% Traditional ROI: 3%
194 Main Street 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: 0.14% Traditional cash on cash: 3.87% Airbnb Rental Income: $1384 Traditional Rental Income: $3223 Airbnb ROI: 0.14% Traditional ROI: 3.87%
410 Main Street South Dennis, MA Step into history with this award -winning circa 1780 home, where timeless character and m...	4 beds \| 3 baths \| 2,132 sq.ft.	$1,650,000	Airbnb cash on cash: -0.27% Traditional cash on cash: 1.36% Airbnb Rental Income: $1934 Traditional Rental Income: $3922 Airbnb ROI: -0.27% Traditional ROI: 1.36%
10 Briarfield Road South Dennis, MA Bright, spacious & well-maintained Colonial with peaks of Cape Cod Bay just 1.5 miles to C...	3 beds \| 3 baths \| 2,545 sq.ft.	$899,000	Airbnb cash on cash: -0.28% Traditional cash on cash: 3.08% Airbnb Rental Income: $1384 Traditional Rental Income: $3775 Airbnb ROI: -0.28% Traditional ROI: 3.08%
299 Main Street South Dennis, MA A truly remarkable Bass River estate, set on an extraordinary 5.11 acres of private waterf...	5 beds \| 5 baths \| 5,814 sq.ft.	$9,500,000	Airbnb cash on cash: -0.96% Traditional cash on cash: -0.42% Airbnb Rental Income: $2259 Traditional Rental Income: $6387 Airbnb ROI: -0.96% Traditional ROI: -0.42%
1354 Route 134 South Dennis, MA Completely renovated and thoughtfully updated, this South Dennis home with 2100 sq. ft. of...	3 beds \| 3 baths \| 2,100 sq.ft.	$964,900	Airbnb cash on cash: -0.3% Traditional cash on cash: 2.68% Airbnb Rental Income: $1384 Traditional Rental Income: $3638 Airbnb ROI: -0.3% Traditional ROI: 2.68%
432 Old Chatham Road #Apt 411 South Dennis, MA Sensational Top-Floor 2-Bedroom Condominium in the Heart of Dennis Beautifully situated in...	2 beds \| 1 baths \| 1,030 sq.ft.	$349,900	Airbnb cash on cash: 0.96% Traditional cash on cash: 5.22% Airbnb Rental Income: $1265 Traditional Rental Income: $2264 Airbnb ROI: 0.96% Traditional ROI: 5.22%
3 academy hill Lane South Dennis, MA Welcome to this beautifully crafted new construction Colonial, thoughtfully designed to co...	4 beds \| 3 baths \| 2,179 sq.ft.	$1,275,000	Airbnb cash on cash: -0.47% Traditional cash on cash: 1.71% Airbnb Rental Income: $1934 Traditional Rental Income: $4009 Airbnb ROI: -0.47% Traditional ROI: 1.71%
10 Eastover South Dennis, MA Move-in ready ranch style home located in the desirable ''Olde Dennis on Bass River'' neig...	3 beds \| 2 baths \| 1,082 sq.ft.	$699,900	Airbnb cash on cash: -0.02% Traditional cash on cash: 2.82% Airbnb Rental Income: $1384 Traditional Rental Income: $2814 Airbnb ROI: -0.02% Traditional ROI: 2.82%
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.	$1,499,000	Airbnb cash on cash: -0.59% Traditional cash on cash: 1.55% Airbnb Rental Income: $1384 Traditional Rental Income: $3934 Airbnb ROI: -0.59% Traditional ROI: 1.55%
1 Charing Cross Road South Dennis, MA This inviting residence offers a warm, storybook feel--where sun-filled interiors, simple ...	2 beds \| 2 baths \| 1,040 sq.ft.	$575,000	Airbnb cash on cash: 0.08% Traditional cash on cash: 3.29% Airbnb Rental Income: $1265 Traditional Rental Income: $2591 Airbnb ROI: 0.08% Traditional ROI: 3.29%
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: 0.04% Traditional cash on cash: 3.22% Airbnb Rental Income: $1384 Traditional Rental Income: $2892 Airbnb ROI: 0.04% Traditional ROI: 3.22%
7 Pinefield Lane 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: -0.45% Traditional cash on cash: 1.97% Airbnb Rental Income: $1384 Traditional Rental Income: $3326 Airbnb ROI: -0.45% Traditional ROI: 1.97%
23 Farm Lane South Dennis, MA Rare opportunity to purchase a large custom cape in the beautiful Farm Lane neighborhood i...	3 beds \| 3 baths \| 2,262 sq.ft.	$1,350,000	Airbnb cash on cash: -0.67% Traditional cash on cash: 1.48% Airbnb Rental Income: $1384 Traditional Rental Income: $3654 Airbnb ROI: -0.67% Traditional ROI: 1.48%
16 Frank Doyle Road South Dennis, MA Welcome to 16 Frank Doyle Road in South Dennis. This 3-bedroom, 1-bath ranch is ideally si...	3 beds \| 1 baths \| 1,008 sq.ft.	$509,000	Airbnb cash on cash: 0.49% Traditional cash on cash: 3.66% Airbnb Rental Income: $1384 Traditional Rental Income: $2472 Airbnb ROI: 0.49% Traditional ROI: 3.66%
18 Asack Drive South Dennis, MA Welcome to 18 Asack Drive, a thoughtfully laid out home in the heart of South Dennis desig...	4 beds \| 3 baths \| 2,428 sq.ft.	$899,000	Airbnb cash on cash: 0.18% Traditional cash on cash: 3.3% Airbnb Rental Income: $1934 Traditional Rental Income: $4032 Airbnb ROI: 0.18% Traditional ROI: 3.3%
5 Coach House Lane South Dennis, MA Open House Cancelled, Property Under Agreement! Stop Renting Cape Cod... Start Living It E...	3 beds \| 1 baths \| 640 sq.ft.	$479,999	Airbnb cash on cash: 0.56% Traditional cash on cash: 3.27% Airbnb Rental Income: $1384 Traditional Rental Income: $2180 Airbnb ROI: 0.56% Traditional ROI: 3.27%
154 Bayridge Drive South Dennis, MA This one just feels easy the second you walk in. Bright, open living with thoughtful finis...	3 beds \| 2 baths \| 1,800 sq.ft.	$699,000	Airbnb cash on cash: 0.02% Traditional cash on cash: 3.6% Airbnb Rental Income: $1384 Traditional Rental Income: $3302 Airbnb ROI: 0.02% Traditional ROI: 3.6%
69 Cyprus Road South Dennis, MA Opportunity Knocks in the Mid-Cape! Set on a level .28-acre lot that directly abuts peacef...	3 beds \| 2 baths \| 1,080 sq.ft.	$529,900	Airbnb cash on cash: 0.36% Traditional cash on cash: 4.15% Airbnb Rental Income: $1384 Traditional Rental Income: $2839 Airbnb ROI: 0.36% Traditional ROI: 4.15%
10 Danielle Drive South Dennis, MA Tucked into a desirable South Dennis neighborhood close to conservation land and Northside...	2 beds \| 1 baths \| 1,038 sq.ft.	$579,000	Airbnb cash on cash: 0.04% Traditional cash on cash: 2.63% Airbnb Rental Income: $1265 Traditional Rental Income: $2265 Airbnb ROI: 0.04% Traditional ROI: 2.63%
80 Forest Hills Drive South Dennis, MA Tucked away and never before offered to the market, this one-of-a-kind home is rich in cha...	4 beds \| 5 baths \| 3,395 sq.ft.	$1,200,000	Airbnb cash on cash: -0.26% Traditional cash on cash: 4.48% Airbnb Rental Income: $1934 Traditional Rental Income: $6715 Airbnb ROI: -0.26% Traditional ROI: 4.48%
55 Cyprus Road South Dennis, MA Great opportunity to own in Dennis! This 2BR, 1.5BA home (built in 1981) with a 3-bedroom ...	2 beds \| 2 baths \| 864 sq.ft.	$525,000	Airbnb cash on cash: 0.24% Traditional cash on cash: 3.4% Airbnb Rental Income: $1265 Traditional Rental Income: $2419 Airbnb ROI: 0.24% Traditional ROI: 3.4%

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 $699,000 and the average price per square foot is $396. In May 2026, the average monthly cash on cash return in South Dennis is 3.00%. The average monthly rental income in South Dennis is $3,223.

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 Short-Term is higher than the Long-Term in South-dennis with average rental income of $1,384.

Your search for investment property begins and ends here

Investment Property for Sale in South Dennis, MA

36 Old Sailors Way

South Dennis, MA

2 beds | 1 baths | 624 sq.ft.

$475,000

Airbnb cash on cash: 0.44%

Traditional cash on cash: 3%

Airbnb Rental Income: $1265

Traditional Rental Income: $2004

Airbnb ROI: 0.44%

Traditional ROI: 3%

194 Main Street

South Dennis, MA

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

$650,000

Airbnb cash on cash: 0.14%

Traditional cash on cash: 3.87%

Airbnb Rental Income: $1384

Traditional Rental Income: $3223

Airbnb ROI: 0.14%

Traditional ROI: 3.87%

410 Main Street

South Dennis, MA

4 beds | 3 baths | 2,132 sq.ft.

$1,650,000

Airbnb cash on cash: -0.27%

Traditional cash on cash: 1.36%

Airbnb Rental Income: $1934

Traditional Rental Income: $3922

Airbnb ROI: -0.27%

Traditional ROI: 1.36%

10 Briarfield Road

South Dennis, MA

3 beds | 3 baths | 2,545 sq.ft.

$899,000

Airbnb cash on cash: -0.28%

Traditional cash on cash: 3.08%

Airbnb Rental Income: $1384

Traditional Rental Income: $3775

Airbnb ROI: -0.28%

Traditional ROI: 3.08%

299 Main Street

South Dennis, MA

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

$9,500,000

Airbnb cash on cash: -0.96%

Traditional cash on cash: -0.42%

Airbnb Rental Income: $2259

Traditional Rental Income: $6387

Airbnb ROI: -0.96%

Traditional ROI: -0.42%

1354 Route 134

South Dennis, MA

3 beds | 3 baths | 2,100 sq.ft.

$964,900

Airbnb cash on cash: -0.3%

Traditional cash on cash: 2.68%

Airbnb Rental Income: $1384

Traditional Rental Income: $3638

Airbnb ROI: -0.3%

Traditional ROI: 2.68%

432 Old Chatham Road #Apt 411

South Dennis, MA

2 beds | 1 baths | 1,030 sq.ft.

$349,900

Airbnb cash on cash: 0.96%

Traditional cash on cash: 5.22%

Airbnb Rental Income: $1265

Traditional Rental Income: $2264

Airbnb ROI: 0.96%

Traditional ROI: 5.22%

3 academy hill Lane

South Dennis, MA

4 beds | 3 baths | 2,179 sq.ft.

$1,275,000

Airbnb cash on cash: -0.47%

Traditional cash on cash: 1.71%

Airbnb Rental Income: $1934

Traditional Rental Income: $4009

Airbnb ROI: -0.47%