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$9,500,000

  • For Sale
  • Active
  • Single Family
  • 5 Beds
  • 4 Full Baths
  • 1 Partial Bath
  • 5,814 Sq. Ft.
  • 5.11 Acres
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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.

Full Property Details for 299 Main St

General

  • Price: $9,500,000
  • Taxes: $13,640 (2025)
  • Status: Active
  • Type: Single Family
  • Source: CCI
  • MLS ID: 22600117
  • Updated: 1/21/2026
  • Added to Site: 23 day(s) ago

Interior

  • Number of Rooms: 10
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Appliances: Electric Water Heater
  • Flooring: Hardwood, Carpet, Tile

Rooms

Bathrooms

  • Total Bathrooms: 5
  • Full Bathrooms: 4
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 5
  • Primary Bedroom: Second
  • Bedroom 3: Second Level
  • Bedroom 4: Second Level
  • Bedroom 5: First Level

Other Rooms

  • Laundry: First Floor

Additional Information

  • Pool: Yes
  • Private Pool: Yes
  • Pool Description: In Ground

Parking

  • Garage: Yes
  • Total Spaces: 7

Location

  • County: Barnstable
  • Driving Directions: Route 134 to Highbank Road to Main Street to #299.

Heating & Cooling

  • Cooling Type: Central Air

Utilities

  • Sewer: Septic Tank

Structural Information

  • Architectural Style: Cape Cod
  • Construction: Shingle Siding
  • Exterior Const.: Shingle Siding
  • Basement Desc.: Partial, Crawl Space
  • Roof: Asphalt
  • Stories/Levels: 2
  • Square Feet: 5,814
  • Year Built: 1953
  • Property Condition: Updated/Remodeled, Actual

Lot Features

  • Lot Size (Acres): 5.11
  • Lot Size (Sq. Ft.): 222,592
  • Lot Size Source: Field Card
  • Street/Road Desc.: Paved
  • Zoning: r40

Water Features

  • Water Front: Yes
  • Water View: Yes

Financial Considerations

  • Price Per Sq. Ft.: $1,633
  • Assessment Amount: $4,634,900
  • Land Assmt: $2,531,000
  • Tax Amount: $13,640
  • Tax Year: 2025

Disclosures and Reports

  • Special Conditions: None
  • Property ID: DENN M:000117 P:054000

Listed by Sotheby's International Realty, Inc., Tori R Harrison Farr

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Listing agent

— 299 Main St —

  • Tori R Harrison Farr

    Sotheby's International Realty, Inc.

508 455 7288

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 299 Main St

School District:Dennis-Yarmouth School District
NameGradesDistance
Ezra H Baker
810 Route 28, Dennis, MA 02670
PK-30.9 mi
Dennis-Yarmouth Intermediate School
286 Station Avenue, Yarmouth, MA 02664
4-52 mi
Dennis-Yarmouth Regional High School
210 Station Avenue, Yarmouth, MA 02664
9-121.8 mi
Dennis-Yarmouth Middle School
286 Station Avenue, Yarmouth, MA 02664
6-82 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 299 Main St Get Price Alerts and Save Property

Date
Details
Price
Change
Source
1/12/2026
Listed
$9,500,000
313.04%
MLS
4/18/2007
Sold
$2,300,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 299 Main St

Year
Property Taxes
Change
Tax Assessment
Change
2025
$13,640
2%
$3,150,200
4%
2024
$13,341
3%
$3,038,900
9%
2023
$12,975
4%
$2,778,300
25%
2022
$12,471
4%
$2,227,000
12%
2021
$12,035
4%
$1,995,900
5%
2020
$11,566
5%
$1,896,000
6%
2019
$10,984
-10%
$1,780,300
-7%
2018
$12,196
3%
$1,923,700
—
2017
$11,831
-5%
$1,923,700
1%
2016
$12,399
2%
$1,898,800
—
2015
$12,152
2%
$1,898,800
1%
2014
$11,922
—
$1,877,500
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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*These costs are estimates, and the interest rates assume exceptional credit standing.

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NMLS#: 1598647

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Listed by Sotheby's International Realty, Inc., Tori R Harrison Farr

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299 Main Street, Dennis, MA 02660 (MLS# 22600117) is a Single Family property with 5 bedrooms, 4 full bathrooms and 1 partial bathroom. 299 Main Street is currently listed for $9,500,000 and was received on January 12, 2026. Want to learn more about 299 Main Street? Do you have questions about finding other Single Family real estate for sale in South Dennis? You can browse all South Dennis real estate or contact a Coldwell Banker agent to request more information.

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