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:
1/21/2026
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. 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.
More Information MLS# 22600117
Contract Info
List Price/SqFt: 1633.99
Start Showing Date: 2026-01-21
Status: Active
Original List Price: 9500000
List Price: $9,500,000
Current Price: $9,500,000
List Date: 2026-01-12
Legal and Taxes
Town: Dennis
Village: South Dennis
Estimated Annual Taxes: 13640
Building Assessments: 2103900
Other Assessments: 0
Total Assessment: 4634900
Flood Ins Required: Yes: verify w/insurance agent
Lead Base Paint: Unknown
Mass Use Code: 101 - Residential, single family
Nitrogen Sensitive Area: Yes
Street #: 299
Street Name: Main
Street Suffix: Street
County: Barnstable
State: MA
Zip Code: 02660
Tax ID: DENN M:000117 P:054-000
Tax Year: 2025
General Property Info
Region: Mid-Cape
School District: Dennis-Yarmouth
Zoning: r40
Property Sub-Type: Single Family Residence
Renovated: Yes
Stories: 2
Total Rooms: 10
Field Card SqFt: 5814
Basement: Yes
Baths - Half: 1
Private Dock: Yes
Private Pool: Yes
Lot Size SqFt: 222592
Leased Land: No
Lot Size Source: Field Card
Acres: 5.11
Irregular: Yes
Garage: Yes
# of Cars: 2
# of Parking Spaces: 7
Year Round: Yes
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: 1
Property Includes Recording Devices: Yes
Device Records: Both Audio and Video
Year Built: 1953
Total Finished Space: 5814
Bedrooms - Total: 5
Baths - Full: 4
Baths - Total: 5
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. 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.
Directions to Property: Route 134 to Highbank Road to Main Street to #299.
Street Description
Paved: 1
Special Listing Cond
None: 1
Lot Features
Gentle Sloping: 1
Level: 1
Year Built Desc
Actual: 1
Basement Description
Partial: 1
Parking Features
Driveway: 1
Off Street: 1
Architectural Style
Cape Cod: 1
Garage Description
Attached: 1
Foundation Details
Crawl Space: 1
Private Dock Description
Water: 1
Convenient To
Golf Course: 1
House of Worship: 1
Major Highway: 1
Medical Facility: 1
School: 1
Convenient to Water Body 1: Bass River
Floors
Carpet: 1
Hardwood: 1
Tile: 1
Sewer
Septic Tank: Title V Grade Level
Roof Description
Asphalt: 1
Siding Description
Shingle: 1
Primary Bedroom
Primary Bedroom Level: Second Floor
Heating
Forced Air: 1
Bedroom 2
Bedroom 2 Level: Second Floor
Cooling
Central Air: 1
Bedroom 3
Bedroom 3 Level: Second Floor
Fuel Type
Oil: 1
Bedroom 4
Bedroom 4 Level: First Floor
Water
Public: 1
Hot Water
Water Heater: 1
Hot Water Source
Electric: 1
Laundry Room
Laundry Room Level: First Floor
Other Structures
Gazebo: 1
Exterior Features
Private Yard: 1
Private Pool Description
In Ground: 1
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: January - 21 - 2026
Broker Attribution:
508 455 7288
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