Exquisite Shingle-Style Estate in Massachusetts Asks $9.5 Million for Timeless Elegance and Modern Comfort

In the prestigious South Side of Weston Massachusetts, 56 Doublet Hill Rd offers a rare combination of architectural grace, thoughtful amenities, and sophisticated design. Priced at $9,500,000, this 7,418 square foot Colonial-style estate sits on a sprawling 1.68 acre lot, surrounded by mature landscaping and scenic tranquility. Built in 2002, the home has undergone several transformations that elevate it into the highest echelon of Weston Real Estate.

Over the past two decades, 56 Doublet Hill Rd has evolved both in value and vision. It last changed hands in 2018 for $5.3 million and before that, in 2012 for $3.475 million. The current listing reflects not only the rising demand in Massachusetts Real Estate, but also the meticulous attention to detail poured into every corner of the estate.

“It’s not just a home—it’s a statement,” said a representative of The Shulkin Wilk Group in a conversation with Luxury Houses Magazine. “The seller took what was already a fine property and transformed it into a true sanctuary for luxury living.”

SEE MORE: A Coastal Masterpiece: Modern Island Living Awaits in Massachusetts for $10,995,000

56 Doublet Hill Rd – Elegant Interiors Meet Modern Comfort

Step through the main entrance and you’re greeted by a grand two story foyer, accented by natural light and detailed millwork. The interiors unfold into a seamless series of living spaces: a sun-drenched family room with French doors, a formal living room with a fireplace, and a custom-designed home office that balances elegance and productivity. Rich hardwood flooring runs throughout the main level, anchoring the open layout in warmth and character.

The gourmet kitchen is a true centerpiece. Outfitted with high-end stainless appliances, an oversized island, and sleek granite countertops, it caters equally to intimate family meals and upscale entertaining. Upstairs, the primary suite is a private retreat with a walk-in closet and a luxurious spa-inspired bathroom complete with soaking tub and double vanities.

“Every room feels intentional. The design fosters both intimacy and grandeur—an incredibly rare balance,” the agent told Luxury Houses.

The finished lower level is a destination unto itself. Featuring a golf simulator, full fitness studio, wine cellar, and modern bar, the space is ideal for recreation, relaxation, and hosting in style.

SEE MORE: A Waterfront Masterpiece: 7.6 Acres of Park-Like Grounds and Architectural Excellence by Andrew Franz for $10.95 Million

A Backyard That Rivals the Best Resorts

Yet it’s the outdoor amenities that truly set this property apart. The backyard has been meticulously designed to evoke the experience of a five star resort. A sleek contemporary pool and integrated spa serve as the visual and social heart of the property, surrounded by curated landscaping and mood lighting.

A fully equipped outdoor kitchen is tucked beneath a covered patio, complete with high-end appliances, counter space, and bar seating. Just steps away, a stone recreation pavilion features a fireplace and overhead heaters, extending the al fresco season well into the New England fall.

“It’s like living in the Berkshires or Martha’s Vineyard—but you’re just minutes from downtown Boston,” the listing agent noted in an interview with Luxury Houses Magazine. “The outdoor experience here is what truly sets it apart.”

SEE MORE: Modern Luxury at Its Best: New Construction Home with Walls of Glass for Optimal Light & Privacy in Massachusetts, $5.9 Million

Weston Offers Prestige and Convenience

Located just 15 miles west of Boston, Weston is widely recognized for its top-tier public schools, quiet wooded neighborhoods, and proximity to world-class shopping, dining, and recreation. Residents of 56 Doublet Hill Rd enjoy quick access to the Massachusetts Turnpike I90, I95, and the MBTA commuter rail at Kendal Green Station.

The town offers an exceptional quality of life, with access to several private golf clubs, tennis courts, and well-maintained walking trails. Nearby Wellesley and Newton provide gourmet grocers, fine dining, and boutique retail just a short drive away.

Luxury Houses Magazine attempted to contact the current owner for comment, but the homeowner chose to remain private.

This exceptional estate at 56 Doublet Hill Rd isn’t just one of the finest listings in Weston Real Estate — it represents a lifestyle defined by elegance, comfort, and privacy. Whether for family life, entertaining, or retreating into peace, this home delivers on every front.

For more information, visit the Zillow or connect with The Shulkin Wilk Group at Compass to schedule a private tour.

* 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:

• 
  Exquisite Shingle-Style Estate in Massachusetts Asks $9.5 Million for Timeless Elegance and Modern Comfort
• 
  A Coastal Masterpiece: Modern Island Living Awaits in Massachusetts for $10,995,000
• 
  A True Masterpiece of Elegance and Exclusivity in Massachusetts Lists for $13.5 Million
• 
  A Waterfront Masterpiece: 7.6 Acres of Park-Like Grounds and Architectural Excellence by Andrew Franz for $10.95 Million

---