299 Main Street, South Dennis, MA 02660 (MLS# 22600117)
299 Main Street, South Dennis, MA 02660
$9,500,000
Property Type:
Residential
Bedrooms:
5
Baths:
5
Square Footage:
5,814
Lot Size (sq. ft.):
222,592
Status:
Active
Current Price:
$9,500,000
List Date:
1/21/2026
Last Modified:
4/08/2026
Overview
Description
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 leading to the ocean. Outdoor living is elevated with a resort-style pool and gazebo, the perfect setting to unwind and take in unforgettable sunset views. For the equestrian enthusiasts there is a stable.
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.
Listing Details MLS# 22600117
Contract Info
- Original List Price
- 9500000
- List Price/SqFt
- 1633.99
- Start Showing Date
- 2026-01-21
Legal and Taxes
- Street #
- 299
- Street Name
- Main
- Street Suffix
- Street
- County
- Barnstable
- Town
- Dennis
- Village
- South Dennis
- State
- MA
- Zip Code
- 02660
- Tax ID
- DENN M:000117 P:054-000
- Estimated Annual Taxes
- 13640
- Tax Year
- 2025
- Building Assessments
- 2103900
- Total Assessment
- 4634900
- Lead Base Paint
- Unknown
- Flood Ins Required
- Yes: verify w/insurance agent
- Mass Use Code
- 101 - Residential, single family
- Nitrogen Sensitive Area
- Yes
- Other Assessments
- 0
General Property Info
- Region
- Mid-Cape
- School District
- Dennis-Yarmouth
- Zoning
- r40
- Property Sub-Type
- Single Family Residence
- Year Built
- 1953
- Renovated
- Yes
- Total Finished Space
- 5814
- Field Card SqFt
- 5814
- Total Rooms
- 10
- Stories
- 2
- Private Pool
- Yes
- Private Dock
- Yes
- Leased Land
- No
- Lot Size SqFt
- 222592
- Lot Size Source
- Field Card
- Acres
- 5.11
- Irregular
- Yes
- Garage
- Yes
- # of Cars
- 2
- # of Parking Spaces
- 7
- Year Round
- Yes
- Bedrooms - Total
- 5
- Baths - Full
- 4
- Baths - Half
- Yes
- Baths - Total
- 5
- Golf Course Front
- No
- Golf Course View
- No
- Waterfront
- Yes
- Water Body
- Bass River
- Waterfront Type
- Rivers
- Water Body Type
- Fresh
- Water Access Type
- Public
- Waterview
- Yes
- Water Body View
- Bass River
- Waterview Type
- Rivers
- Miles to Beach
- .1 - .3
- Fireplace
- Yes
- # Fireplaces
- Yes
- Property Includes Recording Devices
- Yes
- Device Records
- Both Audio and Video
- Basement
- Yes
Convenient To
- Convenient to Water Body 1
- Bass River
- Golf Course
- Yes
- House of Worship
- Yes
- Major Highway
- Yes
- Medical Facility
- Yes
- School
- Yes
Primary Bedroom
- Primary Bedroom Level
- Second Floor
Bedroom 2
- Bedroom 2 Level
- Second Floor
More Information
Bedroom 3
- Bedroom 3 Level
- Second Floor
Bedroom 4
- Bedroom 4 Level
- First Floor
Laundry Room
- Laundry Room Level
- First Floor
Sewer
- Septic Tank
- Title V Grade Level
DPR Eligibility
- DPR Eligible
- No
Remarks & Misc
- Public Remarks
- 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 leading to the ocean. Outdoor living is elevated with a resort-style pool and gazebo, the perfect setting to unwind and take in unforgettable sunset views. For the equestrian enthusiasts there is a stable. 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.
- Directions to Property
- Route 134 to Highbank Road to Main Street to #299.
Street Description
- Paved
- Yes
Special Listing Cond
- None
- Yes
Lot Features
- Gentle Sloping
- Yes
- Level
- Yes
Year Built Desc
- Actual
- Yes
Basement Description
- Partial
- Yes
Parking Features
- Driveway
- Yes
- Off Street
- Yes
Architectural Style
- Cape Cod
- Yes
Garage Description
- Attached
- Yes
Foundation Details
- Crawl Space
- Yes
Private Dock Description
- Water
- Yes
Floors
- Carpet
- Yes
- Hardwood
- Yes
- Tile
- Yes
Roof Description
- Asphalt
- Yes
Siding Description
- Shingle
- Yes
Heating
- Forced Air
- Yes
Cooling
- Central Air
- Yes
Fuel Type
- Oil
- Yes
Water
- Public
- Yes
Hot Water
- Water Heater
- Yes
Hot Water Source
- Electric
- Yes
Other Structures
- Gazebo
- Yes
Exterior Features
- Private Yard
- Yes
Private Pool Description
- In Ground
- Yes
Property Features
Street Description:
Paved
Special Listing Cond:
None
Architectural Style:
Cape Cod
Year Built Desc:
Actual
Basement Description:
Partial
Foundation Details:
Crawl Space
Lot Features:
Gentle Sloping; Level
Garage Description:
Attached
Parking Features:
Driveway; Off Street
Convenient To:
Golf Course; House of Worship; Major Highway; Medical Facility; School
Floors:
Carpet; Hardwood; Tile
Private Pool Description:
In Ground
Private Dock Description:
Water
Other Structures:
Gazebo
Exterior Features:
Private Yard
Roof Description:
Asphalt
Siding Description:
Shingle
Heating:
Forced Air
Cooling:
Central Air
Fuel Type:
Oil
Water:
Public
Hot Water:
Water Heater
Hot Water Source:
Electric
Lead Paint Disclosure ›
Listing Office:
Sotheby's International Realty, Inc.
Listing Agent:
Tori Harrison Farr
Last Updated: April - 08 - 2026
Broker Attribution:
508 455 7288
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