299 Main Street, South Dennis, MA 02660
Barnstable County
Key Facts
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 leading to the ocean. Outdoor living is elevated with a resort-style pool and gazebo, the perfect setting to unwind and take in unforgettable sunset views. For the equestrian enthusiasts there is a stable. 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 Information
Property Type
Residential
Sub-Type
Single Family Residence
Style
Cape Cod
Year Built
1953
Living Area
5,814 sq ft
Lot Size
5.11 acres
Garage Spaces
2
Parking Spaces
7
Zoning
r40
Days on Market
175
MLS® Listing#
22600117
Property Features
Appliances
Cooling
Flooring
Basement
Pool
Parking
Lot Features
Construction
Roof
Other Structures
Sewer
Rooms
- Bedroom 2Second
- Bedroom 3Second
- Bedroom 4First
- Master BedroomSecond
Financial Details
HOA
None
Annual Taxes
$13,640
Tax year 2025
Assessed Value
$4,634,900
Parcel Number
DENN M:000117 P:054000
Directions
Route 134 to Highbank Road to Main Street to #299.
Affordability Calculator
$1,710,000
Estimated monthly payment
$45,507/mo
Principal $6,840,000 · Est. interest $9,542,409 over 30 yrs
Neighborhood Market Statistics
How this home compares to active listings in South Dennis, MA
- $687,234
- Median Listing Price
- 39
- Median Days on Market
- 1,373
- Median Sq Ft
- $494
- Median Price / Sq Ft
- 227
- Active Listings
- This home’s price is 1144% above the area median.
- Its price per sq ft is 198% above the area median.
Market statistics compiled from active EXIT Realty® and MLS listings in South Dennis, MA.
Location
Points of Interest in South Dennis, MA
Showing the South Dennis area map.
Nearby Schools
Ezra H Baker Innovation School
Elementary · 0.9 mi away
Windmill Childrens Center
School · 1.5 mi away
St Pius X School
Elementary · 1.5 mi away
Dennis-Yarmouth Regional High School
Secondary · 1.8 mi away
Dennis-Yarmouth Middle School
Secondary · 2.0 mi away
Station Avenue Elementary
Elementary · 2.0 mi away
Dennis-Yarmouth Regional School District
School · 2.1 mi away
John Simpkins School
School · 2.4 mi away
N H Wixon Innovation School
Elementary · 2.4 mi away
Holy Trinity School
School · 3.2 mi away
Sunflower School
School · 3.2 mi away
Country Day Montessori School
Elementary · 3.4 mi away
Penny Lane Day School
School · 3.7 mi away
Harwich Elementary School
Elementary · 4.0 mi away
Harwich Middle School
Elementary · 4.0 mi away
Sunshine & Rainbows Learning
School · 4.1 mi away
Mattacheese Middle School
Elementary · 4.4 mi away
Marguerite E Small Elementary
Elementary · 4.5 mi away
Monomoy Regional High School
Secondary · 4.8 mi away
Cape Cod Region Vocational Technical
Secondary · 4.8 mi away
Commute Calculator
Nearby Homes
Moving Cost Estimate
EXIT Agents in South Dennis
Listing Courtesy: Sotheby's International Realty, Inc. - 508 455 7288
Presented by: Tori Harrison Farr
Last Updated: 2026-01-12