August 21, 2020

Bestbudbrian / CC BY-SA


Why Purchase and Remodel a Home in Chestnut Hill, Boston?

Considering buying or remodeling a family home in Chestnut Hill?

Here’s our take:

The trendy and elegant Boston suburb of Chestnut Hill has evolved into a decidedly upscale, tree-lined haven established as one of the most classically striking Boston venues to call home. It’s a suburban oasis of beauty within striking distance of Boston proper and to numerous celebrities, political standouts, prominent figures, and their families. One of Boston’s most beautiful seven kingdoms, well known locals like Tom Brady, Michael Dukakis, Patriots owner Robert Kraft, and sculptor John A. Wilson have called Chestnut Hill home.

Located 6 miles to the west of downtown Boston, Chestnut Hill is not a municipality. Rather, it’s technically a village and exclusive neighborhood spanning 70 acres carved out of sections of Brookline, Newton, and Brighton. The area is known as the 02467 — Chestnut Hill’s distinctive zip code. Let it also be known that Chestnut Hill is not a single hill, but rather a series of hills overlooking the Chestnut Hill Reservoir.


Chestnut Hill’s History

As a bit of background, Chestnut Hill was largely undeveloped farmland and woodlots in the mid-1700s, owned by several prominent Boston families. An expanse of this enclave held a curtain of Chestnut trees — hence the name. 

As much of the land in Chestnut Hill was sold and subdivided at the same time, Chestnut Hill has a consistency of look, image, and ethos. Landed single-family homes, trees, and an elegant, prosperous suburban vibe are prevalent here. This is arguably the most desirable Boston suburb.

The Chestnut Hill Reservoir is noted today on the National Register of Historic Places and has been a Boston Landmark since 1989. It has back-up status to Boston’s water supply and is essentially on standby in case of an emergency or water crisis, having evolved into a neighborhood oasis with a 1.5 mile running track wending its way around the border. It is an exercise venue, a family walk venue, a pet exercise space, and simply a lovely area to step outside and enjoy the natural beauty that is Massachusetts.

Arriving at Chestnut Hill from Boston proper, one is plunged into an extensive expanse of trees, well-kept lawns, pristine roads, dignified homes, country estates, and mansions. Not at all the overstated flash one would see in an urban environment such as Los Angeles, sections of New York, or other urban hubs. There is a stately dignity to Chestnut Hill — as if each home has shown up well dressed to a black tie affair by invite only. It’s impressive, dignified, and tailored to the nines. Beautiful and everyone knows it — no reason to shout. Plenty of old money here.

The vibe is distinctly wooded, upscale suburban, and The Boston College Chestnut Hill Campus is a prominent part of this area, spanning 175 acres in all with 120 buildings on this campus.


Architecture in Chestnut Hill

Gasson Hall clock tower at Boston College from Chestnut Hill Reservoir –


As one moves through Chestnut Hill, examples of Colonial Revival, Italianate, Shingle, Tudor Revival, and Victorian architectural styles can be seen. The sprawling campus that is Boston College is Collegiate Gothic — apparently its early stage. (,_Massachusetts)


Art and Culture in Chestnut Hill

Allandale Farm 

For a beautiful change of pace and taste of nature you can visit Allandale Farm. It’s a truly lovely 105 acre farm located in Chestnut Hill and an incredible venue to pick up fresh fruit and vegetables grown right there with sustainable farming practices. For a true vintage touch, the iconic Allandale farm house was originally built in 1778.


The Street 

The Street offers over 600,000 square feet of trendy open air shopping and dining with more than 40 stores and dining options, located on Route 9. Portobello Road offers eclectic shopping options, as does Jonathan Adler. Intermix and MiniLux offer venues where women can indulge themselves. One can pop in for a Lululemon fix, crash Peloton for a cycling session, and then hit any one of The Street’s delicious dining options (there are more than a dozen). Yes, please.


The Showcase Superlux 

This is a movie and dining experience simply elevated to the next level. Recliner seating done in theatre, iPad touch menus, and high-level dining with a menu that ranges from steak and sashimi prepared from scratch, to calamari and lobster sauteed with asparagus. Moviegoers are able to enjoy delicious burgers with vermont cheddar and hand cut fries delivered by an attentive waiter. The popcorn is hot and bottomless with the purchase of your ticket, and the experience is truly five-star.


Chestnut Hill Square

A combination of shopping, dining, and amenities ranging from Anthropologie and Athleta to Soulcycle and Equinox. A nice pedestrian path runs through the center of the parking lot where you can walk from your car to the shops after parking. This pedestrian space is nicely landscaped and has outdoor seating where you can enjoy a coffee or a bite outside.


Chestnut Hill Hotspots

Boston College across from Chestnut Hill Reservoir MA.jpg –


There are many — here are a few of our favorites:

The Capital Grille

At Capital, one is in for an elegant, comfortable experience in a beautiful setting with African Mahogany and art deco chandeliers. Incredible seafood, paired with exceptional wines and dry-aged steaks make for an excellent family experience. The Tuna Tartare with avocado and the Chilean Sea Bass with Miso butter are both amazing.



One of Boston’s best Italian restaurants. Originally founded in 1985 by a then 25-year-old Steve Fillipo, Davios has grown in reputation and footprint, renowned for their Northern Italian cuisine. They do an exceptional gluten-free menu, and as far as dinner goes the Main Lobster Risotto with Asparagus, Fresh Herbs, and Lobster Cream is absolutely amazing.


Legal Sea Food

One of Boston’s premiere seafood venues which has been going for over four decades now. A pure legend. The seafood fare and clam chowder is as fresh as it gets in Boston and the filet mignon is excellent. 


Frank Pepe Pizzeria

This utterly iconic brand was originally established in New Haven, Connecticut in 1925 as Frank Pepe’s Pizzeria Napoletana and is argued by some to be the best pizza in the entire United States. Some loyal Bostonions were known to make the 2-hour drive to New Haven simply to experience this pizza without peer. However Frank Pepe has now opened a location in Chestnut Hill, sparing the avid Bostonians the drive and reducing the overall New England carbon footprint thereby. 

The backstory: Frank Pepe was an Italian immigrant who came to America and opened his first shop in 1925 in New Haven, CT. He opened a shop offering quality wood-fired pizzas with an authentic Italian vibe and the family hasn’t looked back. There are now 9 Frank Pepe locations. They are extremely popular, import certain key ingredients from Italy to maintain quality, and are run by Frank Pepe’s grandson. Their dough recipe is literally a proprietary secret, and the white clam pizza says it all… The central oven is a coal-fired, fourteen-foot brick oven that dominates the room and creates a crust truly like no other.


Transportation in Chestnut Hill

There are three stops on the Green Line which service Chestnut Hill: Chestnut Hill Ave, South Street Boston College; Cleveland Circle; and Reservoir, Chestnut Hill.

Boston is increasingly cycle-friendly, with a large expanse of cycling lanes and more being added. Cycling is being built into the ethos of Boston. This has created a more European feel where one can cycle to work, the grocery store, market, or simply throughout the city for enjoyment and exercise. Boston Mayor Marty Walsh makes Boston’s cycling planning clear here: That being said, Chestnut Hill proper is more car and driving oriented.

Ridesharing giants Uber and Lyft also both operate throughout Chestnut Hill and Boston.


Airport Access

Logan International Airport is about 12 miles from Chestnut Hill via the I-90. You are looking at 21 mins or so depending on traffic (or 16 mins or so for an early morning flight). Logan is one of the world’s largest international airports from which you can access virtually any carrier or destination. Logan is the 16th largest airport in the US and offers direct flights to areas throughout the US, Canada, Mexico, Latin America, the Caribbean, Europe, Africa, and Asia.


Seasons and Weather in Chestnut Hill

Main Entrance Boston College
Main entrance, Boston College, Chestnut Hill, Mass. [Card]. (1930). Retrieved from


Chestnut HIll has all four seasons — including a beautiful spring and absolutely stunning fall season with changes in color, leaves falling, and a BC Campus that flares into color due to its abundance of Norway Maples. Designer sweaters and coats, trend-setting boots, and a woodsmoke tang in the air make the experience distinctive and special. The area has a cultured and homey feel to it.


Schools in Chestnut Hill

Schooling in Chestnut Hill is serviced by the public school systems of Brookline and Newton —  there are also several private school options:


The Chestnut Hill School

Founded in 1860, The Chestnut Hill School is dedicated to educating elementary age students from age 3 through grade 6.


Brimmer School

Established in 1880, Brimmer is Pre-Kindergarten through 12th grade, with an enrollment of approximately 400 students.


Chestnut Hill Real Estate

Average sale price for a home in Chestnut HIll last month was 1.8 million USD. One can far exceed this in Chestnut Hill if looking for distinctive, landed estates.

These are the real estate offices I suggest one contact when interested in purchasing a home in Chestnut Hill.


Home Remodeling Trends in Chestnut Hill

Design-Build is proving to be the sought-after approach for those seeking maximum creativity, value, and quality for their investment in home, mansion, or estate renovation projects in Chestnut Hill. Here are the two contrasting approaches:

Design-Bid-Build is the process which has been introduced over the past 150 years or so whereby you hire an architect to draft plans and design your project, to then have it bid out to contractors seeking to perform the project. This approach has many liabilities for the client due in no small part to the fragmented spheres of responsibilities which exist. There is no single person or entity fully accountable to the client for the entire project’s success. Thus you can have expensive design work, impractical planning, numerous change orders, shoddy craftsmanship, and projects which are off timeline and over budget. In the end the client can be left damaged. You may have experienced this in the past.

Design-Build is clearly the way to go if you want to save on time and money, reduce stress and eliminate a fragmented sense of project responsibility in the people working for you. Design-Build is a model which stresses single-source accountability with the creative design, planning, and remodel executed start to finish by one firm.

Design Build is turned to by professionals, families, and individuals as the cutting edge of efficiency, aesthetics, practicality, and accountability when it comes to designing and remodeling a home. This approach packages architectural design and interior design services with highly-skilled and artisan-level building and remodeling services. This natural synthesis makes for a simple, efficient, and accountable creative process followed by a streamlined and responsible execution process. This reduces cost, time of execution, and client stress throughout. In the Design Build modality, the client is dealing solely with one fully accountable firm. 

New England Design and Construction does Architectural Design-Build. Here are several examples of beautiful design build remodels we have done in Chestnut Hill, Massachusetts and the Boston area.



Chestnut Hill is peerless in elegant, classic Boston-style homes and estates. A truly lovely neighborhood in which to purchase or remodel a family home. If you can — go for it!



Published August 21, 2020 | By

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