Chestnut Hill

A view of the Chestnut Hill Reservoir and skyline of Boston

A view of the Chestnut Hill Reservoir and skyline of Boston

Chestnut Hill, straddling Brookline, Newton, and a tiny sliver of Boston, is a unique and picturesque area known for its blend of suburban serenity and urban accessibility. With its lush landscapes and magnificent homes, it offers a peaceful retreat from city life while still providing easy access to the amenities of Boston's metropolitan area, The Street in Chestnut Hill, Newton Centre and Coolidge Corner.

Architecturally, Chestnut Hill presents a number of stately and historic homes reflecting the area's rich history. Home values in Chestnut Hill tend to be above average, indicative of how desirable the neighborhood is, and the quality of life it offers.

Regarded for its natural beauty and green spaces, Chestnut Hill is characterized by mature trees, and beautifully landscaped properties. Residents and visitors alike enjoy parks and conservation areas, such as the Hammond Pond Reservation and the Chestnut Hill Reservoir, which provide opportunities for outdoor recreation and peaceful walks amidst scenic surroundings, some of which offer a magnificent view of Boston’s skyline.

Education is a key attraction of Chestnut Hill, with a range of top-rated schools across its three municipalities. These schools are known for their academic rigor and commitment to student development, making Chestnut Hill an ideal location for families prioritizing education. Those seeking a private school right in the neighborhood have three options including Beaver Country Day School, The Brimmer and May School, and The Chestnut Hill School with other alternatives a bit further away.

Boston College, a prestigious university, is an integral part of the Chestnut Hill landscape. Established in 1863, the college's stunning Gothic architecture adds a historic and academic flair to the area. Its sprawling campus, permeated by manicured lawns and classic buildings, contributes significantly to the aesthetic appeal of Chestnut Hill. The presence of this esteemed university enriches the community with a vibrant, intellectual atmosphere, drawing students from across the country. The college also plays a vital role in the local community through various cultural events, public lectures, and sporting events, particularly its NCAA Division I football, basketball and hockey teams. The influence of Boston College extends beyond education, contributing to the area's dynamic and culturally rich environment.

The culinary scene in Chestnut Hill is as diverse as its geography, with the Newton section boasting the vast majority of dining options along Route 9 (a.k.a. Boylston Street). From quaint cafes to gourmet restaurants to pizza, coffee shops, and more, the area satisfies a wide spectrum of culinary tastes and preferences.

The Street, a stretch along Route 9 of Chestnut Hill in the Newton section, has undergone and continues to undergo a massive facelift. The Street is a bustling shopping center that offers just about everything you could ask for. From grocery stores, bookstores, Shake Shack and fine dining like Davio’s to a SuperLux movie theater, Lululemon, Nike, The Container Store, Pottery Barn and much more! If that’s not enough, The Chestnut Hill Mall is a few yards further west on Route 9 and also offers an assortment of shops and restaurants including the very popular Cheesecake Factory and Bloomingdales.

Public transportation connects the Brookline, Newton, and Boston sections of Chestnut Hill to the greater Boston area. The MBTA facilitates easy commuting via the Green Line B, C and D branches, as well as multiple bus lines enhancing the convenience of living in this charming and multifaceted neighborhood.

Chestnut Hill is also home to The Longwood Cricket Club, a historic institution known for its rich tradition in the sport of tennis. Founded in 1877, it moved to Chestnut Hill from Boston in 1922, and is one of the oldest tennis clubs in the United States. Tennis legends including Arthur Ashe, Rod Laver, Ken Rosewall, Bjorn Borg, Billie Jean King, Martina Navratilova and more all competed there. The club is renowned for its beautifully maintained grass courts but also has a few clay courts. Over the years, Longwood Cricket Club has hosted numerous national and international tennis events, but no longer does that. Membership at Longwood is highly sought after, reflecting its status as a symbol of tennis tradition and social prestige in the Chestnut Hill area.

Chestnut Hill truly is a harmonious blend of natural beauty, architectural diversity, educational excellence, and urban convenience. It is a neighborhood that not only offers a high standard of living but also maintains a warm sense of community and historical charm.

Map of Chestnut Hill Area

Home Values in Chestnut Hill

The Average Chestnut Hill, Brookline home was assessed at $2,257,427 in fiscal year 2025.

The average Chestnut Hill, Newton single family home was assessed at $2,141,644 in fiscal year 2024. That was the highest average single family home value of any Newton village.

In contrast, the average Chestnut Hill, Newton condominium was assessed at $710,570.

Top Streets By 2025 Assessed Value in Chestnut Hill (Brookline)

• Alwyngton Rd: $4,892,175
• Reservoir Ln: $4,860,267
• Norfolk Rd: $4,457,970
• Dunster Rd.: $3,699,900

Top Streets By 2024 Assessed Value in Chestnut Hill (Newton)

• Essex Rd: $6,351,358
• Suffolk Rd: $4,184,540
• Chestnut Hill Rd: $3,646,092
• Woodman Rd.: $3,595,217

Notable 2023 Homes Sold in Chestnut Hill (Brookline)

• 96 Crafts Rd: $5,500,000
• 195 Middlesex Rd: $4,800,000
• 37 Circuit Rd: $4,500,000
• 19 Crafts Rd: $4,250,000

Notable 2023 Homes Sold in Chestnut Hill (Newton)

• 52 Hammondswood Rd: $4,000,000
• 50 Beacon St: $3,890,000
• 101 Old Orchard Rd: $3,200,000
• 24 Lee Rd: $3,015,000

Picturesque Hammond Pond

Picturesque Hammond Pond

Preschools

• Panda Club Academy: A Mandarin Immersion Montessori school located on Boylston Street.
• Soule Early Childhood Center: Run by the Town of Brookline, this preschool’s philosophy is The Montessori Method of education.
• Boston College Children's Center: Preschool program for children age 2 years 9 months – 5 years old providing high quality early childhood education to preschoolers in Chestnut Hill and South Brookline.
• BeiBei Cub Academy: Bilingual home daycare with a focus on Mandarin located on Hammond Street.
• Jewish Community Center (JCC): Located on the Brookline/Brighton line, this long standing preschool has been around more than 50 years.

Schools

• Beaver Country Day School: Private school serving 6th-12th graders situated on 17 acres.
• Chestnut Hill School: Private school in the heart of Chestnut Hill for Pre-K through 6th grade.
• Brimmer and May School: Private school in Chestnut Hill around the corner from Chestnut Hill School and Beaver Country Day that starts in Pre-K and educates kids all the way through high school.
• Hayes School: This Brookline public school is home for those that live on the Brookline side of Chestnut Hill.
• Ward School: This Newton public school is home for most of the kids that live on the Newton side of Chestnut Hill.

Coffee Shops

• Blue Bottle Coffee: Located at The Street, this gem offers outdoor seating along with hot and cold drinks.
• Dunkin Donuts: Located along Commonwealth Avenue near Boston College, this popular chain is known for its coffee and donuts
• Glazed Bytes: Unassuming coffee shop in the Shops at Chestnut Hill (a.k.a the Chestnut Hill Mall).
• Starbucks: Located next to Wegmans on Route 9, Starbucks needs no introduction.

Restaurants

• Bernard's: Upscale Chinese food in a pleasant atmosphere located along The Street.
• Cheesecake Factory: Located in The Shops at Chestnut Hill, this popular chain serves just about anything you want with an emphasis on dessert of course.
• Chef Dave's: Arguably the best Mac N Cheese in the area.
• Davio's: Located in the Showcase SuperLux Theatre, Davio’s is a popular Italian steak house serving delicious pasta, meat, fish and more.
• Frank Pepe Pizzeria Napoletana: Casual pizzeria serving coal-fired pies, beer & wine in The Shops at Chestnut Hill.
• Legal's Seafood: Classic New England seafood, this two-story fish emporium elevates the 40-year legacy of its original location in Chestnut Hill (a few doors down from where it is now.)
• Seasons 52: Rotating menu of seasonal American dishes alongside international wines in an upscale setting.
• Shake Shack: A popular and fun place for kids where ping pong is offered outside among other games.
• The Capital Grille: High-end steak house serving up fresh cuts of meat, fish and more.

Supermarkets

• Star Market: Longstanding grocery store in the heart of Chestnut Hill that has everything you could possibly need.
• Wegmans: One of the most popular markets (and liquor stores) in the area draws people from all over town.

Parks

• Soule Playground: With two soccer fields, playground equipment and a splash pad in the summer, this is one of the most popular parks in Chestnut Hill.
• Skyline Park: Doubles as both a soccer field for youth sports and the high school, and a place for outdoor enthusiasts to walk or run along the paved path.
• Chestnut Hill Reservation: A very popular place for runners and walkers to circle, it has an unobstructed view of Boston’s skyline and is located next to Boston College.
• Hammond Pond Reservation: A popular spot for dog walkers to roam with a beautiful pond that’s home to swans and ducks.

Chestnut Hill Newton Streets

Chestnut Hill Brookline Streets

Chestnut Hill Boston Streets

• Beacon St. (parts of)
• Chestnut Hill Ave. (parts of)
• Reservoir Rd. (parts of)