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Residential Land with Home for Sale in South Dennis, Massachusetts

299 Main St, South Dennis, MA 02660

$9,500,000
5.1 acres
Active
ago
Est $47,684/mo

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.

5,814
Sq feet
5
Beds
4
Full baths
1
1/2 bath
1953
Built

Location

Street address
299 Main St
Community
Dennis
School district
Dennis-Yarmouth
Elevation
3 feet
Coordinates
41.6806, -70.1586

Directions

Route 134 to Highbank Road to Main Street to #299.

Property details

Acreage
5.11 acres
MLS #
CCIAOR 22600117
Posted

Property taxes

2025
$13,640

Parcels

  • DENN M:000117 P:054-000

Details and features

Listing

Type
Residential
Subtype
Single Family Residence
Zoning
R 40

Lot

View
River
Features
Gentle Sloping, Level

Exterior

Parking Spaces
7
Parking
Driveway, Off Street
Structures
Gazebo
Features
Private Yard

Structure

Stories
2
Basement
Partial
Water
Public
Sewer
Septic Tank
Heating
Forced Air, Oil
Cooling
Central Air
Materials
Shingle Siding
Roof
Asphalt

Interior

Room Count
10
Rooms
Basement, Bathroom x 5, Bedroom x 5
Flooring
Carpet, Hardwood, Tile
Appliances
Water Heater

Listing history

DateEventPriceChangeSource
Jan 21, 2026New listing$9,500,000CCIAOR
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This 5.11-acre property is located at 299 Main St in South Dennis, MA 02660. The property is available for sale for $9,500,000. It has a 5,814 sq ft 5 bedroom, 4 bath house built in 1953.

Checked 2 hours ago — Updated

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Copyright (C) 2026 Cape Cod & Islands Association of REALTORS®, Inc. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

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