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Living in Chestnut Hill, MA

Elisabeth Preis December 11, 2024


Nestled just outside of Boston, Chestnut Hill, Massachusetts, is a picturesque and affluent neighborhood that offers residents the perfect blend of suburban tranquility and urban convenience. Known for its historic charm, prestigious educational institutions, and upscale amenities, Chestnut Hill is a sought-after community for those seeking a high quality of life within close proximity to the city. In this guide, we’ll explore what makes living in Chestnut Hill so appealing, from its beautiful homes and green spaces to its rich cultural offerings and top-rated schools.

Location and Accessibility: The Best of Both Worlds

Chestnut Hill is uniquely positioned at the intersection of three municipalities—Boston, Brookline, and Newton—giving residents access to the best of all three communities. This strategic location allows for easy access to Boston’s bustling downtown while providing a serene, suburban atmosphere that feels worlds away from the city’s hustle and bustle.

For commuters, Chestnut Hill offers multiple transportation options. The MBTA’s Green Line serves the area, with several stops in Chestnut Hill, making it convenient for residents to reach downtown Boston, Cambridge, and other nearby areas. Additionally, major highways like Route 9 and the Massachusetts Turnpike (I-90) are easily accessible, providing quick routes for those who prefer to drive.

Whether you’re commuting to work in the city or enjoying a weekend getaway in the countryside, Chestnut Hill’s prime location ensures that you’re always well-connected.

Neighborhoods and Housing: A Blend of Historic and Modern

Chestnut Hill is renowned for its stunning homes, which range from historic estates to modern luxury residences. The neighborhood’s architectural diversity is one of its most distinctive features, offering something for everyone, whether you’re drawn to the classic elegance of a Colonial-style home or the sleek lines of contemporary design.

  • Historic Homes: Many of Chestnut Hill’s residences date back to the late 19th and early 20th centuries, reflecting the neighborhood’s rich history. These homes often feature classic New England architecture, with stately facades, spacious interiors, and meticulously landscaped grounds. Living in one of these historic homes offers a unique sense of character and charm.
  • Luxury Condominiums: For those seeking modern amenities and convenience, Chestnut Hill also offers a range of luxury condominiums and townhomes. These properties often feature state-of-the-art finishes, open floor plans, and access to exclusive amenities such as fitness centers, pools, and concierge services. They are particularly popular among professionals, empty nesters, and those looking for a low-maintenance lifestyle.
  • Suburban Estates: Chestnut Hill is home to some of the most prestigious estates in the Greater Boston area. These expansive properties offer privacy, luxury, and beautiful views, often set on large lots with mature trees and landscaped gardens. They provide a peaceful retreat while remaining close to the amenities of the city.
Whether you’re looking for a historic home with character or a modern residence with all the latest amenities, Chestnut Hill’s diverse housing options cater to a variety of tastes and lifestyles.

Parks and Recreation: Enjoying the Outdoors

Chestnut Hill is a haven for outdoor enthusiasts, offering numerous parks, trails, and recreational facilities that cater to all ages and interests. The neighborhood’s commitment to preserving green spaces is evident in its beautifully maintained parks and outdoor amenities.

  • Chestnut Hill Reservoir: One of the most popular spots in the area, the Chestnut Hill Reservoir offers a picturesque setting for walking, jogging, and picnicking. The 1.5-mile loop around the reservoir is a favorite among residents for its scenic views and tranquil atmosphere. It’s also a great spot for birdwatching and enjoying the changing seasons.
  • The Country Club: Founded in 1882, The Country Club in Chestnut Hill is one of the oldest country clubs in the United States. It offers a prestigious golf course, tennis courts, and a swimming pool, making it a central hub for recreational and social activities in the community.
  • Larz Anderson Park: Just a short drive away, Larz Anderson Park in Brookline is a sprawling green space that offers stunning views of the Boston skyline, a skating rink, picnic areas, and playgrounds. It’s a great place for families to spend the day outdoors.
  • Boston College Athletic Facilities: Boston College’s athletic facilities, including Alumni Stadium and Conte Forum, offer opportunities for sports enthusiasts to watch college football, basketball, and other events. The university’s fitness centers and recreational programs are also available to the public through membership, providing additional options for staying active.
With its wealth of parks and recreational facilities, Chestnut Hill offers residents plenty of opportunities to enjoy the outdoors, whether you’re taking a leisurely stroll around the reservoir or participating in more structured activities at The Country Club.

Shopping and Dining: Upscale and Diverse Options

Chestnut Hill is a shopper’s paradise, offering a variety of upscale retail destinations and dining options that cater to a wide range of tastes. Whether you’re in the mood for a fine dining experience, a casual meal, or a day of shopping, Chestnut Hill has something to offer.

  • The Street Chestnut Hill: A premier shopping destination, The Street Chestnut Hill features a mix of high-end retailers, boutique shops, and popular restaurants. From fashion and home decor to fitness studios and gourmet groceries, The Street has it all. Notable dining options include The Capital Grille, known for its steaks and seafood, and Del Frisco’s Grille, which offers a modern take on American classics.
  • Chestnut Hill Square: Another popular shopping center, Chestnut Hill Square offers a mix of luxury retailers, wellness services, and dining options. It’s home to several well-known brands, including Anthropologie and SoulCycle, as well as restaurants like Seasons 52 and Sweetgreen, which emphasize healthy, seasonal ingredients.
  • Wegmans: The arrival of Wegmans, a beloved grocery store known for its high-quality products and expansive selection, has been a game-changer for Chestnut Hill residents. Whether you’re stocking up on gourmet ingredients or grabbing a quick bite from the prepared foods section, Wegmans offers a convenient and enjoyable shopping experience.
  • Fine Dining: For those who enjoy fine dining, Chestnut Hill offers several upscale restaurants that cater to discerning palates. Aquitaine, a French-inspired bistro, is a local favorite, while Legal Sea Foods offers fresh seafood in an elegant setting.
Chestnut Hill’s diverse shopping and dining scene ensures that residents have access to a wide range of options, whether they’re looking for everyday essentials or indulging in a special night out.

Partner with the Chestnut Hill Real Estate Expert

Chestnut Hill, MA, is more than just a neighborhood; it’s a community that offers an exceptional quality of life. With its prime location, beautiful homes, top-rated schools, and abundant amenities, Chestnut Hill is an ideal place to live for those seeking the perfect balance

For nearly two decades, Elisabeth Preis has been celebrated for her compassionate ear and professionalism. Her keen negotiating skills and engaging personality make her a standout advocate and a joy to work with.

With deep market insight and thorough preparation, Elisabeth makes the buying and selling process seamless for her clients. Named a Boston Magazine top producer from 2019-2023, she closed over $50 million in transactions in 2023 alone. Ready to find your dream home? Contact Elisabeth today!

Search homes for sale in Chestnut Hill here.



Work With Elisabeth

She feels it is truly a privilege to help clients find their "happy place" and to be involved in such an exciting and meaningful moment in her clients' lives.