299 Main Street
1 / 5
For Sale

299 MAIN STREET

$9,500,000

299 Main Street, South Dennis

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.

Property Details

5

Bedrooms

5

Bathrooms

5,814

Sq Ft

Features & Amenities

Type: Single Family Residence
Year Built: 1953
Heating: Has Heating (Unspecified Type)
Cooling: Central Air
Parking: 2 Attached Garage spaces
Lot: 5.11 Acres
Days on Zillow: 40 Days
Price/sqft: $1,634

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.

Property Details

Bedrooms

5

Bathrooms

5

Square Feet

5,814

Property Type

SINGLE_FAMILY

Features

  • Type: Single Family Residence
  • Year Built: 1953
  • Heating: Has Heating (Unspecified Type)
  • Cooling: Central Air
  • Parking: 2 Attached Garage spaces
  • Lot: 5.11 Acres
  • Days on Zillow: 40 Days
  • Price/sqft: $1,634

Gallery

299 Main Street - Photo 1
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299 Main Street - Photo 6

Location

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Listing Information

MLS ID:55873243
Listing Date:2026-03-03

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Cape Cod & Islands data last updated at March 3, 2026 at 10:01 AM