Chestnut Hill Dining & Shopping Guide

World-renowned for its historic architecture, land preservation, and top-tier institutions, Chestnut Hill is an idyllic yet lively neighborhood — but Chestnut Hill is more than just its history. From its upscale, authentic dining experiences with menus featuring global cuisine to its luxurious shopping centers, Chestnut Hill's vibrant dining and shopping opportunities will surprise and dazzle.

Want to know more about the Chestnut Hill shopping and dining experience? I can answer all your Chestnut Hill area questions! Learn more about my experience with Chestnut Hill real estate here.

The Street at Chestnut Hill

With an inviting, walkable feel, the design for The Street at Chestnut Hill is claimed to be inspired by some of the most iconic retail streets in the world. Nestled within the heart of Chestnut Hill and Newton, just make one visit to this plaza's quaint outdoor dining and well-kept grounds and you'll agree with that sentiment! To locals, this shopping center feels like a slice of heaven. From family fun with complimentary storytimes offered by Hummingbird Books to sidewalk sales and street fairs or outdoor fun at The Green, The Street at Chestnut Hill always has something exciting going on. You can also look forward to restaurants like Davio's Northern Italian Steakhouse offering seasonal wine-tasting experiences. Highlights of the local Street cuisine include Aquitaine, the Parisian-inspired bistro with authentic French dining, and Legal Sea Foods, a two-story seafood emporium featuring a fish market on the ground floor and dining on the second floor. Even dogs can enjoy The Street by stopping by Polkadog Bakery, a boutique bakery that serves our furry friends handmade, gourmet treats! If you or your pet needs a checkup, Chestnut Hill Medical Center and the new Bond Vet clinic are here to take care of you and your pal. You can explore their complete directory of shops, services, and dining here.

Luxury retailers and boutique experiences dominate The Street, so it's no secret why you'll feel like you're treating yourself every time you stop by one of their renowned shops, apparel stores, salons, centers, and more: Barry's, Bluemercury, Bond VetCasper, Chase BankChestnut Hill Medical CenterHummingbird Books, J.McLaughlin, LegitLululemon, Madison ReedMiniLuxeNike by Chestnut Hill, PelotonPolkadog BakeryPorcelanosaPottery Barn, Simon Pearce, Showcase SuperLux Movie Theatre, Skin Spa New YorkSplendid, Star Market, Studs, The Container Store, Warby Parker, Verizon, Vince, and more. Visit The Street at Chestnut Hill directory for more information.

Israeli, French, Italian, Thai, Mediterranean, Mexican, and more — The Street's menu is overflowing with limitless possibilities with authentic dishes from global cuisines; not only will you never have to eat the same thing twice, but as a bonus, you'll also feel like a world-traveler: Aquitaine, Bernard’sBiancaBlue Bottle Coffee, Chef Dave’sChilacatesDavio’s Italian Steakhouse, Hummus v’HummusJuice PressLegal Sea FoodsLimaniOddFellows Ice Cream Co.Pineapple ThaiShake ShackThe Bagel Table, and more. Visit The Street at Chestnut Hill directory for more information.

The Shops at Chestnut Hill

Formerly called The Mall at Chestnut Hill, The Shops at Chestnut Hill is an indoor mall that offers a wide variety of luxury shopping experiences anchored by Bloomingdale's and other upscale stores, where you can choose from all the best clothing lines, electronics, home furnishings, and more. If you're looking for medical or health and wellness services, you can schedule a massage at Relaxation Therapy, get high-quality skin treatments at Pharmaciopy, or even make an appointment with Dr. Darryl Grace for your next eye exam and get exclusive eyewear at Opticians3. To find all of their shops, businesses, restaurants, and services, visit the mall directory here for more information; you'll find that several businesses have curbside pickup available as well as both dine-in and take-out options. Some locations may not yet be open, so be sure to plan ahead and check the opening dates and business hours.

If you love name-brand stores and up-scale shopping experiences, The Shops at Chestnut Hill will suit your art, beauty, and fashion tastes, home decor style, and more with these options: Ann TaylorApple, AZ Fine Art GalleryBloomingdale’s, Boston Barkery, Brooks Brothers, Chicos, Coach, Crate and Barrel, Eileen Fisher, Evereve, Hedi's FurnitureJ. JillJ.Crew, LOFT, LUSH Fresh Handmade Cosmetics, Michael Kors, NIC+ZOEPandora, Queenia, Salon Assaf Rizk, Sephora, Stuart Weitzman, SwarovskiTalbot's, The Threading Spa, Tiffany & Co.UniqloVineyard Vines, and more. Visit The Shops at Chestnut Hill directory for more information.

After a luxury shopping experience works up your appetite, The Shops at Chestnut Hill offer a variety of cuisine and restaurant styles combined with several sweet options that will make for a memorable dining experience, from morning to evening: Cheesecake Factory, DaikanyamaForty CarrotsFrank PepeGelato & Chill, Glazed BytesThe Friendly ToastTokyo Japanese Steakhouse, and more. Visit The Shops at Chestnut Hill directory for more information.

Chestnut Hill Square

If you're looking for an outdoor shopping experience with unique, local retailers, stopping by Chestnut Hill Square is a must-visit. This open-air shopping district is central to the historic Chestnut Hill and offers visitors and residents alike a walkable environment in this idyllic Massachusetts village. To keep up with year-round events scheduled at Chestnut Hill Square, you can find more information about their art exhibits, concerts, beer garden, and more here. In addition to its number of shops, businesses, and dining options, Chestnut Hill Square also offers various health care and aesthetics options, including an urgent care center and a plastic surgeon.

From clothing and accessories stores to salons and fitness centers, you can enjoy these shops and more at Chestnut Hill Square: AnthropologieAthletaDry Bar, EquinoxFrancesca’s, Free People, Lunette OpticPaper SourceSerena & LilyThe Shade Store, and SoulCycle. Visit the Chestnut Hill Square directory for more information. 

With fresh grilles, a wine bar, and an upscale supermarket, everyone can find something to satisfy their cravings: Capital Grille, Oath PizzaSeasons 52StarbucksSweetgreen, and Wegman's. Visit the Chestnut Hill Square directory for more information.

The Shops at Putterham

Located within Putterham Circle, The Shops at Putterham is the commercial district for South Brookline and has several businesses, eateries, and recreational pursuits. This center may be a small outdoor shopping strip, but its position in South Chestnut Hill at the intersection of Grove Street and W. Roxbury Parkway means that it is still upscale but with a quieter and more local or suburban feel. If your idea of fun is to wind down with some award-winning challah at Cheryl Ann’s Bakery after a round at the nearby 18-hole golf course at Putterham Meadows, The Shops at Putterham is a great place to find excellent service-oriented shops.

The shops in Putterham Circle offer a variety of services from dry cleaning, hair and nails, custom framing, banking, and more: Avery & Co., Brookline BankGastonart & Frame of BrooklineMiddlesex Locksmith, Sibal’s Hair SalonStephanie’s Flowers Of Chestnut Hill, and Towne Cleaners.

Although the dining options may be limited, they all have a star quality that makes them all hard to miss: Cheryl Ann’s BakeryMandarin GourmetPutterham Grille, Putterham Market, and Starbucks.

Cleveland Circle in Brighton

Located at the intersection of Boston's Beacon Street and Chestnut Hill Avenue, laid out in 1850 and 1845 respectively, Cleveland Circle is an outdoor shopping center known for its casual dining options. In the Brighton neighborhood, it's especially a great option for students who study at Boston College due to its proximity to the MBTA railway. Both the MBTA Green Line C Branch and the D Branch have stops nearby at the Cleveland Circle station and the Reservoir station. Because of this, Cleveland Circle is also sometimes called the Cleveland Circle and Reservoir to collectively refer to the shops and businesses that are adjacent to both stops.

Most of the businesses in the Cleveland Circle area are service-oriented, including banks, convenience stores, gas stations, as well as insurance providers, and medical practices: with the C Branch and D Branch stations here, this center is a go-to for locals needing to run a quick errand: Body Soul & MindBoston ConvenienceChestnut Hill Dental AssociatesCleveland Circle Hardware, Coin Cloud Bitcoin ATM (in Boston Convenience), CVSDiscount Tire Repair PartsFSL AssociatesGene Dvorkin Insurance AgencyGentle Eyebrow Threading for WomenHarberOne BankMattress Superstore, Purity Nail Bar, Santander Bank ATMShell, The Vape Shop Cleveland CircleThree C's Cleveland Circle ConvenienceZipcar, and 7 Eleven.

If you enjoy sushi and Asian fare, Cleveland Circle has several great spots, including Sushi Momento in the AC Hotel by Marriot: Amelia’s TaqueriaCafé LandwerCityside TavernChipotle Mexican Grill, DunkinEagle’s Deli, Energize, Fin's Sushi & Grill, Kung Fu TeaMy Happy Hunan KitchenPino’s Pizza, Reservoir Wine & SpiritsStarbucksSushi Momento, and The Circle Tavern.

Newton Shopping Districts Near Chestnut

Newton Centre

One of thirteen villages in Newton, Newton Centre's main commercial center is a triangular-shaped area situated at the intersections of Beacon Street, Centre Street, and Langley Road. While shopping at Newton Centre is a bit more limited than some of the shopping districts within Chestnut Hill, residents close by can still count on Newton Centre to cover their basic needs with amenities such as: Betsey Jenney, CVS, Karma Fine Crafts, Mosher's Men's Store, Mr. Sid, Newtonville Books, Picadilly Market, The Silver Woman, and The UPS Store. 

One thing that Newton Centre does not compromise on? Its restaurants, bakeries, and sweet shops. Take a tour around the world from Latin and Asian-inspired dishes to Italian and Mediterranean cuisine, or just find a seat at a diner that serves American fare — the choice is yours: BaramorBlackbird Doughnuts Newton CentreCafé Sol Azteca, Café St-Petersburg, Coconut Newton, Ding’s KitchenDunkin'Farmstead Table Restaurant, Four Spoons Thai Inspired Cuisine & BarGalit's Treats Café & BakeryHouse of Tandoor Indian and Nepali CuisineJake’s Falafel CornerJinny’s PizzeriaJohnny’s LuncheonetteJ.P. LicksLee’s Burger PlaceLittle Big Diner, Newton Centre Town PizzaPh Viet’s II, Rosenfeld Bagel Co, Sandwich Works, SubwaySUSHICOSweet Tomatoes Pizza, sycamore., Tango MangoTartufo RestaurantTatte Bakery & Café, The Savage Wiener™Thistle & LeekTous Les JoursUnion Street Restaurant and Bar, and 11:11 Health Bar.

Needham Street Shops

A strip mall between the villages of Newton Highlands and Newton Upper Falls, Newton Street Village Shops is a mile-long, 19,000 sq ft gateway to what is referred to as the Needham Street Retail Corridor. Major national retailers and chain restaurants serve this shopping district in Newton's affluent community: Alex & Company Jewelry, Arlene & Roberta Jewelry, AT&T Store, Avi Boston, Bank of America Financial Center, Boston Ski & Tennis, Burn Boot Camp, Cha's Taekwon-do, China Fair, ConnectFit Fitness Equipment-Newton, Creative Playthings, Deka Lash Newton, European Wax Center, EverPresent, Gray Bother's Auto Detailing, Home Design Place, HomeGoods, Jiffy Lube, Johnson Fitness & Wellness Store, Lakeshore Learning Store, Landry’s Bicycles, Loyal Companion, Majestic Nails, Marshalls, Mass General Brigham Urgent Care - Newton, Massage Envy, Michael’s, Mobile, Needham Street Cleaners, Nothing Bundt Cakes, Paper Annex, PetSmart, PureLuxe, Restore Hyper Wellness, Salon Fabio, Sierra, Splash, Stop & Shop, The Vitamin Shoppe, T.J. Maxx, Town Fair Tire, Veterinary Emergency Group, Verizon, Waju Fitness, and more.

From chain coffee shops and dining to local eateries and markets, this shopping center has you covered for all meals of the day: Baza Gourmet Food & Spirits, B.Good, Chipotle Mexican Grill, Dave’s Hot Chicken, District 118 Kitchen & Bar, Dunkin', Farm Grill and Rotisserie, Five Guys, McDonald’s, New England Soup Factory, Pressed Café, Slow Dough Pizza, Starbucks, Upper Falls Beverage Store, and more.

Newton Highlands

Newton Highlands is just one of thirteen villages in Newton, with the Newton Highlands Historic District — complete with its residential and commercial businesses — having been established in the late 19th century. There are many shops and businesses along the Lincoln and Walnut streets, less than 0.5 miles from the shops along Needham Street. Salon Capri, CoCo Nail & Spa, Highland Opticians, Indulge!, Let's Glow Esthetics Co, LuxCouture, Salon Capri, Pine Village Preschool - Newton Highlands, Station Row, The Walnut Market, USPS, and more.

Asian, French, Mexican, Mediterranean, American — Newton Highland's may be a smaller area, but there's no shortage of cuisine opportunities to satisfy a foodie: Anna’s Taqueria, Buttonwood, Dunkin', Grape Leaf Mediterranean Grille, Highland Wine & Spirits, Lakon Paris Patisserie, O'Hara's Food & Spirits, Otake Sushi Bistro, Sichuan Gourmet House, The Dining Car Cafe and Market, 57 Lincoln Kitchen, Walnut Grille, and more.

Keep Exploring Chestnut Hill with Ingvild Brown

There are many reasons why you should consider moving to Chestnut Hill, from our excellent public and private schools to lovely preserved historic buildings, architecturally diverse residences, and scenic grounds. If you are considering purchasing or selling a home in Chestnut Hill – or perhaps Brookline or Newton – or if you simply want to learn more about Chestnut Hill, I can handle all of your questions.

Whether you are looking for a new single-family housecondo, or investment property, I will help you navigate the current market to find the place you can call home. Contact me online or call my office at 571-481-0440 to get started on your journey!