Exquisite Massachusetts Estate Featuring Timeless Grandeur Hits the Market for $7.975 Million
A historic estate known as Highwick Farm Manor has returned to the market in the heart of the Berkshires, bringing a rare blend of heritage architecture and modern luxury to one of New England’s most desirable countryside destinations. The residence at 399 Under Mountain Rd in Lenox is currently listed for $7.975 million, offering more than a century of architectural history across a sprawling private landscape.
Originally built in 1900 as a gentleman’s equestrian retreat, the Tudor-style manor has undergone years of meticulous restoration. Today, the property spans approximately 9,364 square feet, with eight bedrooms and seven bathrooms positioned across 11.45 acres of scenic Berkshire countryside. With its heritage architecture and exceptional setting, the estate represents a notable offering within the Massachusetts Real Estate market, particularly for buyers seeking historic estates in culturally rich destinations.
“The property tells a story of Berkshire heritage,” said listing agent Molly Thomas of Compass, speaking with Luxury Houses Magazine. “The owners approached the restoration with extraordinary care, preserving the home’s original craftsmanship while ensuring it functions beautifully for modern living.”
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A Historic Berkshire Cottage with Timeless Character
From the moment visitors arrive at 399 Under Mountain Rd, the estate’s historic presence becomes immediately clear. The Tudor-style design reflects the architectural traditions that defined many grand summer homes built in the Berkshires during the early 20th century.
Inside, Highwick Farm Manor retains a remarkable collection of period details. Lead-glass windows frame sweeping pastoral views while warm walnut paneling runs throughout several living spaces. Elegant pocket doors allow rooms to open and close fluidly, creating both intimate settings and expansive entertaining areas.
Perhaps the most distinctive interior feature is the home’s ten fireplaces, each contributing to the warm, historic atmosphere that defines the residence. Bay windows, wood flooring, and carefully restored architectural details enhance the sense of classic Berkshire elegance.
“The craftsmanship inside this home is extraordinary,” Thomas told Luxury Houses Magazine. “When you walk through the rooms, you see the level of care that went into maintaining the architectural integrity of the original 1900 design.” For buyers exploring Lenox Real Estate, homes with this level of preserved character and scale are increasingly rare.
Private Grounds and Scenic Berkshire Views
Beyond the manor itself, the landscape surrounding 399 Under Mountain Rd provides a serene setting that captures the natural beauty of the Berkshires. Mature trees, landscaped lawns, and open pasture views surround the residence, offering both privacy and picturesque scenery.
The estate includes an in-ground swimming pool and outdoor patio areas designed for entertaining and relaxation. Several vantage points across the property provide distant hill views and seasonal water vistas, reinforcing the tranquil atmosphere that has long drawn second-home buyers to the region.
According to Thomas, the location adds another dimension to the estate’s appeal. “Properties with this level of acreage so close to downtown Lenox are incredibly limited,” she explained to Luxury Houses Magazine. “At 399 Under Mountain Rd, you enjoy the peace of a private country estate while still being minutes from restaurants, cultural venues, and shopping.”
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A Remarkable Turnaround in Value
The market history of 399 Under Mountain Rd reflects the extensive transformation the property has undergone in recent years. Public records show the estate sold for $625,000 in 2018, when the structure required significant renovation.
After a major restoration effort, the property returned to the market and ultimately sold again in February 2022 for $4.835 million. Now listed at nearly $8 million, the home represents a striking increase in value, highlighting the strength of high-end Massachusetts Real Estate, particularly in the Berkshires.
“The Berkshire luxury market has evolved significantly,” Thomas said. “Buyers today are looking for authentic historic estates that have been thoughtfully restored, and 399 Under Mountain Rd is exactly that type of property.”
Within the broader Lenox Real Estate landscape, estates of this scale and architectural pedigree remain highly sought after, especially among buyers relocating from major Northeast cities.
A Coveted Address in the Berkshires
The appeal of 399 Under Mountain Rd extends beyond the estate itself to the vibrant cultural community surrounding it. Lenox is widely known as one of the Berkshires’ most prestigious towns, attracting visitors year-round for its arts scene, natural beauty, and historic charm.
Nearby attractions include Tanglewood, where the Boston Symphony Orchestra performs during the summer season. The town also offers boutique shopping, farm-to-table dining, hiking trails, and scenic countryside drives that have long defined the Berkshire lifestyle.
For buyers seeking historic estates in the Northeast, opportunities like 399 Under Mountain Rd represent the rare convergence of architectural history, expansive land, and proximity to one of the region’s most celebrated cultural destinations.
The property listing is currently featured on the real estate platform Zillow, where buyers can view additional property data and market insights. Prospective purchasers can also explore more details through the brokerage website of Compass, which is marketing the estate on behalf of the sellers.
* 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*
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