299 Main Street, South Dennis, MA, 02660

Save
Ask
Tour
Hide
Share
$9,500,000
35 Days On Site

299 Main Street
South Dennis, MA 02660

For Sale|Single Family Residence|Active
5
Beds
5
Total Baths
4
Full Baths
1
Partial Bath
5,814
SqFt
$1,634
/SqFt
1953
Built
County:
Barnstable
Listing courtesy of Tori R Harrison Farr of Sotheby's International Realty, Inc.
299 Main Street299 Main Street299 Main Street299 Main Street
Save
Ask
Tour
Hide
Share

Mortgage Calculator

Monthly Payment (Est.)

$43,343
Calculator powered by Showcase IDX, a Constellation1 Company. Copyright ©2026 Information is deemed reliable but not guaranteed.

A truly remarkable Bass River estate, set on an extraordinary 5.11 acres of private waterfront.This stunning property is the epitome of Cape Cod elegance, where timeless character meets thoughtful modern luxury.Lovingly restored to honor its original charm, the home has been impeccably updated throughout while preserving the architectural details that make it so special. At the heart of the residence is a grand, state-of-the-art kitchen, designed for both everyday living and elegant entertaining.Spanning over five acres, the grounds create a rare private riverfront oasis, complete with a private dock offering direct access to the Bass River. Outdoor living is elevated with a resort-style pool and gazebo, the perfect setting to unwind and take in unforgettable sunset views.With five generously sized bedrooms, this exceptional home offers space and comfort for family and guests alike. A property of this scale, setting, and craftsmanship is rarely available truly one of a kind and not to be missed.

Save
Ask
Tour
Hide
Share
Listing Snapshot
Price 
$9,500,000
Days On Site 
35 Days
Bedrooms 
5
Inside Area (SqFt) 
5,814 sqft
Total Baths 
5
Full Baths 
4
Partial Baths 
1
Lot Size 
5.11 Acres
Year Built 
1953
MLS® Number 
22600117
Status 
Active
Property Tax 
$13,640
HOA/Condo/Coop Fees 
N/A
Sq Ft Source 
N/A
Friends & Family
Recent Activity
a month agoListing updated with changes from the MLS®
a month agoListing first seen on site
General Features
Acres 
5.11
Attached Garage 
Yes
Garage 
Yes
Garage Spaces 
2
Land Lease 
No
Parking 
Attached
Parking Spaces 
7
Property Condition 
Updated/Remodeled
Property Sub Type 
Single Family Residence
Sewer 
Septic Tank
SqFt Total 
5814
Style 
Cape Cod
Zoning 
r40
Interior Features
Appliances 
Electric Water Heater
Basement 
PartialCrawl Space
Cooling 
Central Air
Fireplace 
Yes
Fireplaces 
1
Flooring 
HardwoodCarpetTile
Heating 
Bedroom 2 
Level - Second
Bedroom 3 
Level - Second
Bedroom 4 
Level - First
Master Bedroom 
Level - Second
Save
Ask
Tour
Hide
Share
Exterior Features
Construction Details 
Shingle Siding
Lot Features 
On Golf CourseNear Golf CourseLevelWaterfront
Other Structures 
Gazebo
Pool Features 
In GroundPrivate
Private Pool 
Yes
Roof 
Asphalt
View 
WaterRiver
Waterfront 
Yes
Waterfront Features 
Bass River
Waterview 
WaterRiver
Community Features
MLS Area 
Mid-Cape
Roads 
Paved
School District 
Dennis-Yarmouth
Township 
Dennis
Schools
School District
Dennis-Yarmouth
Elementary School
Unknown
Middle School
Unknown
High School
Unknown
Listing courtesy of Tori R Harrison Farr of Sotheby's International Realty, Inc.



Listing information is provided by Participants of the Cape Cod Islands Association of REALTORS MLS. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Copyright 2026, Cape Cod Islands Association of REALTORS MLS.
Last checked: 2026-02-26 12:32 AM UTC

Neighborhood & Commute
Source: Walkscore
Disclosure: Community information and market data powered by Constellation Data Labs. Information is deemed reliable but not guaranteed.
Save
Ask
Tour
Hide
Share