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Significant Sales: Two 1920s Tudor Estates in Chestnut Hill

52 Hammondswood Road has officially sold for $3.2M, while 6 Woodchester Drive, listed for $4.65M, is currently under agreement.

Chestnut Hill, the New England village just six miles west of Downtown Boston, is blessed with many charming home styles and sought-after town amenities. For proof, look no further than the recent home sales of 6 Woodchester Drive and 52 Hammondswood Roadtwo grand estates that exude the charm and details of classic 1920s Tudor-style structures. Positioned less than half a mile apart in picturesque Chestnut Hill, both homes manifest innovative, modern updates, while complete restorations of the original detail still hold true to the grandeur of their pasts. Today, their refreshed floor plans are spacious and bright, comprised of state-of-the-art kitchens, relaxing master sanctuaries, and secluded backyard oases.


6 Woodchester Drive, Chestnut Hill.

6 Woodchester Drive, Chestnut Hill

At first glance, the 15-room, 7,861 SF Tudor at 6 Woodchester Drive is undeniably stunning. The exterior is a combination of classic and well-maintained original details, complemented by a newly-constructed three-car garage and finished artist studio aboveall enclosed by a striking tree-lined brick and masonry fence. Its no wonder how GSIR veteran Brian Back listed and placed the residence under agreement in only one day.

An impressive covered porch with flagstone floors dominates the entire front corner of the home and leads to an intimate entry of inlaid marble. Behind an intricate iron door lies a magnificent foyer and breathtaking center staircase that naturally flows into both grand formal and informal living areas. Wrapped in walls of solid oak paneling and grounded by refinished parquet floors, the sunken living room offers stunning built-ins and an original limestone fireplace, adding just enough interest to break the span of floor-to-ceiling casement windows. Characterized by its open, airy livings spaces, the main level is the quintessential space for socializing, cooking and dining. The living area features a tranquil sunroom with access to the front porch and rear yard with its walls of windows and French doors, offering privacy without impeding on the serene outdoor setting. Windows are left unadorned to maintain a constant vibrancy of natural sunlight. The banquette size dining room empties into an intimate lounge with wet bar, as well as a cavernous family room and expansive state-of-the-art kitchen. The kitchen includes a large enclosed pantry with an adjacent mud room and bath. The private backyard space is ideally designed for relaxation, where residents and guests can enjoy pre-dinner drinks and conversation on balmy summer evenings. The foyers sweeping grand center staircase leads upstairs to an opulent master suite complete with a balcony facing the immaculately landscaped grounds. Four guest bedrooms and three bathrooms provide ample space for guests to spend the night.

The lower level offers perhaps the most unique features in the home, including an original ships galleon designed wet bar and secret prohibition-era wine cellar once stockpiled with outlawed spirits. An original walkin safe is additionally located on the level. With two expansive games rooms, families will not lack room for playone features a massive stone fireplace for curling up, while the other offers a half bath, separate guest suite and additional full bath.


52 Hammondswood Road, Chestnut Hill.

52 Hammondswood Road, Chestnut Hill

The cozy, fairytale-like facade of this secluded Tudor home belies its grand proportions. Inside this 6,500-square-foot, five bed, five-and-a-half bath estate, ornate finishes and clean lines converge. An abundance of sunlight pours through expansive windows and skylights. The professionally designed interiors encompass three breathtaking fireplaces, high ceilings and radiant hardwood floors throughout. An intimate entrance expands to a grand two-story foyer with a sweeping staircase. In the expansive step-down living room, coffered ceilings add depth and detail overhead, while carved embellishments infuse the original masonry hearth with durability and style. French doors lead to a twenty-six foot glass-enclosed sunroom with flagstone floors that open to a bluestone terrace. The main level is the quintessential space for socializing, cooking and dining. Adorned with a large fireplace, the family room opens to a custom eat-in kitchen that feeds an appetite for convenience and casual dining. Inside the dining room, the chef of the family enjoys the space provided by a separate butlers pantry with marble counters and a prep sink.

On the lower level, a wine room exudes elegance, sophistication, and intrigue. An exercise room, family room, au pair suite and attached two car garage serve as additional luxurious amenities. Positioned on the second floor, the divine master bedroom offers an en-suite bathroom that is exceptionally spacious, with a glass shower and gleaming soaking tub for optimal relaxation. The additional bedrooms are sun-drenched and spacious, outfitted with expansive windows for viewing the lush greenery and colorful splendor of the homes surrounding gardens. During the summer months, an in-ground swimming pool is a cool and inviting respite from the heat, rippling gently in the afternoon breeze.

For more information, contact listing agent Brian Back at (617) 620-9700 or


6 Woodchester Drive, Chestnut Hill.


6 Woodchester Drive, Chestnut Hill.


6 Woodchester Drive, Chestnut Hill.


6 Woodchester Drive, Chestnut Hill.


52 Hammondswood Road, Chestnut Hill.


52 Hammondswood Road, Chestnut Hill.


52 Hammondswood Road, Chestnut Hill.


52 Hammondswood Road, Chestnut Hill.

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