55 Chestnut St, Waltham, MA 02493
Property image
Property image
OFF MARKET

$6,938,600

Trulia Estimate
  • 5 Beds
  • 8 Baths
  • 8,567 sqft (on 1.43 acres)

55 Chestnut St, Waltham, MA 02493

Est. Refi. Payment $42,994/mo*
Refinance Your Home
Currently Off Market - Sold Jun 10, 2021 for $5,100,000

Home Value

Trulia Estimate
$6.94M
Since last month
Increased$25K (+0.4%)
Since last year
Increased$537K (+8.5%)
Since last sale
Increased$2M (+34.7%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +32% in the last 10 years
MonthEstimated value
2026
September 2026$6.87M
August 2026$6.84M
July 2026$6.81M
June 2026$6.89M
May 2026$6.8M
April 2026$6.76M
March 2026$6.7M
February 2026$6.56M
January 2026$6.38M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
6 Baldwin Cir, Weston, MA
0.06
Single-Family Home
$4,850,000
08/26/26
4
4.5
5,858
100 Chestnut St, Weston, MA
0.28
Single-Family Home
$7,255,000
10/02/25
5
6.5
8,205
9 Sanderson Ln, Weston, MA
0.81
Single-Family Home
$4,900,000
06/11/26
5
7
8,363
21 Chestnut St, Weston, MA
0.19
Single-Family Home
$11,000,000
12/04/25
7
10
12,120
180 Highland St, Weston, MA
0.55
Single-Family Home
$6,600,000
03/31/26
5
7.5
11,300
72 Love Ln, Weston, MA
0.88
Single-Family Home
$5,700,000
12/02/25
5
6
8,210
137 Wellesley St, Weston, MA
0.49
Single-Family Home
$2,600,000
11/17/25
5
3.5
5,100
42 Westerly Rd, Weston, MA
0.93
Single-Family Home
$3,750,000
01/15/26
6
6.5
9,064
286 Country Dr, Weston, MA
1.23
Single-Family Home
$7,180,000
06/24/26
6
7.5
8,421
226 Ash St, Weston, MA
0.71
Single-Family Home
$3,166,000
04/30/26
5
4.5
5,496

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
73 Chestnut St, Weston, MA 02493
0.06
$9,450,000
7
10
12,461
For Sale
6 Baldwin Cir, Weston, MA 02493
0.06
$4,850,000
4
4.5
5,858
Recently Sold
74 Chestnut St, Weston, MA 02493
0.09
$1,847,600
5
3.5
3,112
Off Market
22 Chadwick Rd, Weston, MA 02493
0.16
$3,409,800
5
5
6,252
Off Market
21 Chestnut St, Weston, MA 02493
0.19
$11,000,000
7
10
12,120
Recently Sold
100 Chestnut St, Weston, MA 02493
0.28
$7,417,200
5
6.5
8,205
Off Market
171 Wellesley St, Weston, MA 02493
0.32
$3,159,900
6
4
4,936
Off Market
48 Golden Ball Rd, Weston, MA 02493
0.40
$1,309,200
3
2.5
1,800
Off Market
46 Golden Ball Rd, Weston, MA 02493
0.41
$964,500
3
1.5
920
Off Market
142 Wellesley St, Weston, MA 02493
0.48
$2,122,700
4
3
3,760
Off Market
137 Wellesley St, Weston, MA 02493
0.49
$2,669,000
5
3.5
5,100
Off Market
148 Highland St, Weston, MA 02493
0.49
$6,580,100
5
8
11,412
Off Market

Local Information

  • Map ViewExplore the area around 55 Chestnut St.
  • Schools2 Preschool Schools3 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1964
1.43 acre lot
8,567 sqft
$810/sqft
Garage

About this House

On one of the most exclusive streets in Weston, this Colonial masterpiece, expanded and gut renovated by a custom builder in 2007 showcases exquisite quality details such as custom moldings and cabinetry throughout. Designed by top architects, it provides the perfect harmony between casual living and formal entertaining. The vast, open kitchen and family room, plus sunroom with views over the lush back yard, offer rooms for casual relaxation. The breathtaking galleried game room with Crotch Mahogany paneling, elegant dining room, living room and double-height foyer afford the home grand spaces for entertaining. A paneled office with gas fireplace completes the first floor. The luxurious master suite, with 2 walk-in closets, gas fireplace and balcony are on the second floor, along with 3 further bedroom suites. The 5th bedroom suite and large gym are on the 3rd floor. A playroom over the 3-car garage overlooks the sport court and the basement has a media room plus exquisite wine cellar.
55 Chestnut St, Waltham, MA 02493 is a 5 bedroom, 9 bathroom, 8,567 sqft single-family home built in 1964. It last sold for $5,100,000 on Jun 10, 2021. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $6,938,600.

Home Details for 55 Chestnut St

Interior Features

Interior Details
BasementNumber of Rooms: 13Ceiling Fan
Heating & Cooling
Heating: Baseboard, Forced Air, Radiant, GasAir ConditioningCooling System: CentralHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 2Floors: Tile, Carpet, Hardwood, Slate
Appliances & Utilities
Cable ReadyDishwasherDisposalDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace
Security
Security System

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: StonePatioPorchSprinkler System
Parking & Garage
GarageParking Spaces: 10Parking: Garage Attached

Property Information

Year Built
Year Built: 1964
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 1.43 acres

Price and Tax history

DateEventPrice
Jun 10, 2021
Source: N/A
Sold
$5,100,000
Mar 22, 2021
Source: MLS PIN #72778754
Pending
$5,495,000
Mar 17, 2021
Source: MLS PIN #72778754
Contingent
$5,495,000
Jan 26, 2021
Source: MLS PIN #72778754
Listed For Sale
$5,495,000
Jan 17, 2021
Source: MLS PIN #72676299
ListingRemoved

Market trends in Weston

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
48
9MoM

Around this home

What Locals Say about Weston

At least 28 Trulia users voted on each feature.

  • 90 % Say car is needed

  • 85 % Say it's dog friendly

  • 82 % Say it's quiet

  • 80 % Say parking is easy

  • 77 % Say people would walk alone at night

  • 76 % Say there's holiday spirit

  • 74 % Say they plan to stay for at least 5 years

  • 73 % Say yards are well-kept

  • 71 % Say there's wildlife

  • 52 % Say kids play outside

  • 50 % Say neighbors are friendly

  • 44 % Say there are community events

  • 38 % Say there are sidewalks

  • 33 % Say it's walkable to grocery stores

  • 29 % Say streets are well-lit

  • 26 % Say it's walkable to restaurants

Sourced by Trulia users. Learn more about our methodology.
  • Woman
    "It’s a Commuter’s dream. 3 minutes to the Pike or 128, Rt. 30, 20, or 9. 2 acres tucked in. Very convenient & private. "
    0
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  • marc
    "I like in particular the BBQ in the June/July timeframe. Many events are also organized with different themes such as the old,car’,contest."
    3
    Flag
  • Marc
    "Some nice trails to take your dog along with easy access. Plenty of space in the center of town too where you can do long walks. Many people have them which is a plus. "
    0
    Flag
  • Marc d. g.
    "Commute is rather easy since I work in waltham. Best time is to go to work either at 7am or after 9am. The return to home is usually a bit crowded in the 4-6 window but alternative roads exist."
    1
    Flag
  • suez
    "Weston is perfect for families. Excellent schools and this area is a true neighborhood of the old style. Houses are spaced far apart but connected by trials in the abundant conservation land. The neighbors are connected by a love of privacy and nature. They have specifically sought out an area close to Boston that still feels like you are in rural Massachusetts. A mix of historic homes and new modern works well , and the community is united by a love of this very unique environment. We are close to all the amenities of a city yet a world away. You will have to drive to restaurants and shopping and there is no public transportation but you will not have to pack up and vacation in NH or VT, you will live that life everyday and still be 25 minutes from downtown Boston."
    0
    Flag
  • frkmus
    "Open land, a community playground for all homeowners on Kendal Common Rd. and Ellis Rd., allows children to play free of traffic in their virtually private domain. With 20 homes on 40 acres, all constructed in the 1950's, all designed by three architects, this area is unique for many reasons, not the least of which the total absence of fences has for over sixty years firmly implanted a communal spirit among all participating homeowners. The entire land mass is away from main thoroughfares on two virtually private roads; a special haven for young and old alike. Here is where we live and brought up our children."
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LGBTQ Local Legal Protections

Frequently asked questions about 55 Chestnut St

  • What is 55 Chestnut St estimated to be worth?
    Trulia's estimated value for 55 Chestnut St in Waltham, MA is $6,938,600.
  • What is the price history for 55 Chestnut St?
    55 Chestnut St in Waltham, MA last sold for $5,100,000 in June 2021.
  • Is Waltham a buyer's or seller's market?
    Waltham is currently a seller's market, based on recent for-sale activity.
  • What do residents say about Waltham?
    Residents describe Waltham, MA as dog-friendly, quiet, and easy to park in. Most residents say you need a car. See recently sold homes in Waltham, MA.
  • Does 55 Chestnut St have air conditioning?
    Yes, 55 Chestnut St in Waltham, MA has air conditioning.
  • Does 55 Chestnut St have laundry facilities?
    Yes, 55 Chestnut St in Waltham, MA has in-unit laundry.

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