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299 Main Street South Dennis, MA $ 9,500,000
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299 Main Street
$ 9,500,000
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299 Main Street

South Dennis, MA, 02660
$ 9,500,000
Bedrooms5 Baths4.1 Sq 5,814

Monthly Estimate*

$ 58,493

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Single Family Home for sale in South Dennis, MA

for $9,500,000 with 5 bedrooms and 4 full baths, 1 half bath. This 5,814 square foot home was built in 1953 on a lot size of 5.11.

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.

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Single Family Active

Price

$ 9,500,000

Bedrooms

5

Full Bath

4

Half Bath

1

Property Type

Single Family

Taxes

$ 13,640

Style

Cape Cod

Lot Size

5.11

Year Built

1953

Town/City

South Dennis

County/Region

Barnstable

MLS | Web ID

22600117
Features
General
Sewer Septic Tank
Cooling Central Air
Roof Asphalt
Appliances Electric Water Heater
Zoning r40
Garage Spaces 2
Architectural Style Cape Cod
Pool Features In Ground
Construction Materials Shingle Siding
Year Built 1953
Stories Count 2
Township Dennis
Property Subtype Single Family Residence
Tax Year 2025
County Barnstable
New Construction false
Property Type Residential
HOA false
Attached Garage true
Garage Y/N true
Other Structures Gazebo
Total Rooms 10
Full Baths 4
Status Active
Directions Route 134 to Highbank Road to Main Street to #299.
City South Dennis
Body of Water Bass River
High School District Dennis-Yarmouth
Lot Size Units Acres
Lot Size Square Feet 222592
Carport Y/N false
Property Attached Y/N false
Land Lease Y/N false
Tax Annual Amount 13640
Showing Instructions Text Tori Harrison at 508 455 7288 for all showing requests.
Home Warranty Y/N false
Property Condition Updated/Remodeled Actual
Virtual Tour https://player.vimeo.com/video/1154698885?h=75cf682d26 https://player.vimeo.com/video/1154698885?h=75cf682d26
Building Area Units Square Feet
Primary Bedroom Level Second
Living Area Units Square Feet
Standard Status Active
Middle/Junior School District Dennis-Yarmouth
Elementary School District Dennis-Yarmouth
Tax Assessed Value 4634900
Waterview Y/N Rivers
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Interior
Basement Partial Crawl Space
Flooring Hardwood Carpet Tile
Total Fireplaces 1
Air Conditioning Y/N true
Heating Y/N true
Fireplace Y/N true
Half Baths 1
Laundry Features First Floor
Total Bedrooms 5
Below Grade Finished Area Unit Type Square Feet
Total Baths 5
Bedroom 4 Level First
Bedroom 3 Level Second
Second Bedroom Level Second
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Exterior
Lot Features Near Golf Course School Medical Facility Major Highway House of Worship Level
Total Parking 7
Lot Size Area 5.11
Building Area Total 5814
Lot Size Acres 5.11
Road Surface Type Paved
Lot Size Source Field Card
Waterfront Y/N true
Dock Water
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* Excluded Features
List By
Tori R Harrison Farr

Listing Agent

Sotheby's International Realty, Inc.

Broker

tori.harrison@sothebyshomes.com

Email

Affordability Calculator

$59,630
Per Month
98%
2%
0%
Monthly Principal & Interest
$58,493
Monthly Property Taxes
$1,137
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
4720468 Elementary School
4720469 Middle School
Unknown High School High School
See complete school information
Pricing History
DatePricePrice ChangeDescription
1/21/2026$9,500,000 Listed Price

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299 Main Street, South Dennis, MA, 02660 is a Single Family Home for sale at $9,500,000 with 5,814 sqft and a lot size of 5.11. 299 Main Street has 5 bedrooms, 4.1 baths, and was built in 1953. The property's zip code is 02660 which is in South Dennis, MA

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