An Iconic 5.11-Acre Waterfront Estate Defined by Privacy and Prestige at $9.5M

Set on more than five acres of private waterfront, 299 Main Street emerges as one of the most compelling luxury offerings to reach Cape Cod in recent years. Located in the heart of South Dennis, this riverfront estate blends the romance of classic Cape Cod architecture with the expectations of modern luxury buyers, offering privacy, scale, and direct access to the Bass River—an increasingly rare combination in today’s coastal market.

Originally built in 1953, the residence has been meticulously restored to preserve its historic character while introducing refined contemporary updates throughout. According to listing agent Tori Harrison Farr of Sotheby’s International Realty, who spoke with Luxury Houses Magazine, “The home was thoughtfully reimagined to respect its original Cape Cod soul, while elevating every element for modern living. That balance is incredibly difficult to achieve, and it’s what makes this property so special.”

Timeless Architecture Meets Modern Refinement

Spanning 5,814 square feet, the home at 299 Main Street offers five generously proportioned bedrooms and five baths, with interiors designed to feel elegant yet unforced. Hardwood floors, carefully preserved details, and expansive windows create a natural dialogue between the interior spaces and the surrounding landscape. At the center of the home is a state-of-the-art kitchen designed for both everyday use and sophisticated entertaining, anchoring the residence with warmth and functionality.

Beyond the interiors, the grounds unfold as a private riverfront oasis. A resort-style pool, gazebo, and manicured lawns lead to a private dock, offering direct boating access to Nantucket Sound. “This is the kind of property where the outdoor spaces are just as meaningful as the interior,” Farr told Luxury Houses. “From sunset gatherings by the river to quiet mornings on the dock, the setting elevates daily life in a very rare way.”

SEE MORE: Massachusetts Home with Refined Updates and Exceptional Style Listed at $6,649,000

A Proven Legacy Within South Dennis Real Estate

From an investment perspective, the estate also tells a compelling story. Public records show that 299 Main Street last traded in 2007 for approximately $2.3 million, underscoring the long-term appreciation potential of prime waterfront properties. Within the broader South Dennis Real Estate landscape, homes of this caliber—offering acreage, privacy, and direct river frontage—are increasingly scarce.

Market observers note that South Dennis has quietly become one of Cape Cod’s most desirable enclaves, prized for its understated character and proximity to both beaches and inland waterways. As part of the larger Massachusetts Real Estate market, the area continues to attract buyers seeking legacy properties rather than short-term trends.

SEE MORE: A Distinguished $6,888,000 Waterfront Residence with Breathtaking Vistas

Lifestyle, Community, and Coastal Connectivity

Life in South Dennis is defined by balance: peaceful residential streets paired with easy access to golf courses, marinas, medical facilities, and some of the Cape’s most respected dining and shopping destinations. The Bass River itself is a lifestyle amenity, connecting residents to boating, paddleboarding, and waterfront dining throughout the warmer months.

“The appeal here isn’t flash—it’s authenticity,” Farr explained to Luxury Houses Magazine. “Buyers are drawn to South Dennis because it still feels genuine, and this home embodies that sense of place.” Within the context of South Dennis Real Estate, properties that deliver both privacy and connectivity are exceptionally limited.

SEE MORE: Weston Masterpiece Asking $31.5 Million Blends Timeless Grandeur with Cutting-Edge Luxury

A Rare Opportunity in Massachusetts Real Estate

As demand for legacy waterfront homes continues to rise, opportunities like 299 Main Street stand apart for their scale, craftsmanship, and setting. In the broader Massachusetts Real Estate landscape, few offerings combine historic charm, modern luxury, and over five acres of private riverfront land within such close proximity to Cape Cod’s cultural and recreational highlights.

For discerning buyers seeking a timeless retreat with enduring value, this Bass River estate represents not just a home, but a generational opportunity—one that reflects the very best of Cape Cod living.

Listing information for 299 Main Street is currently available on Zillow, with the property represented by listing agent Tori Harrison Farr of Sotheby’s International Realty.

* This property might not for sale at the moment you read this post; please check property status at the above Zillow or Agent website links*

More Homes in Massachusetts here:

• 
  Serene Luxury: A Masterpiece Estate by Kistler & Knapp on 5.84 Acres in Massachusetts Offered at $18.25 Million
• 
  Weston Masterpiece Asking $31.5 Million Blends Timeless Grandeur with Cutting-Edge Luxury
• 
  A Distinguished $6,888,000 Waterfront Residence with Breathtaking Vistas
• 
  Massachusetts Home with Refined Updates and Exceptional Style Listed at $6,649,000

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