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

55 Chestnut St
Waltham, MA 02493

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

$6,848,400

Trulia Estimate
as of Aug 7, 2026
Est. Refi. Payment $41,010/mo*

$6,848,400

Trulia Estimate
as of Aug 7, 2026
Est. Refi. Payment $41,010/mo*
5 Beds
8 Baths
8,567 sqft
(on 1.43 acres)

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

Property Type
Single-Family Home
Year Built
1964
Lot Size
1.43 acres
Living Area
8,567 sqft
Price/Sqft
$799
Parking
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. It is currently off market. The Trulia Estimate is $6,848,400, with a rent estimate of $5,663/month.

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 History for 55 Chestnut St

DatePriceEventSource
06/10/2021$5,100,000Sold
N/A
03/22/2021$5,495,000PendingMLS PIN #72778754
03/17/2021$5,495,000ContingentMLS PIN #72778754
01/26/2021$5,495,000Listed For SaleMLS PIN #72778754
01/17/2021ListingRemovedMLS PIN #72676299
06/18/2020$5,495,000Listed For SaleAgent Provided
11/25/2019$5,995,000ListingRemovedAgent Provided
04/03/2019$5,995,000Listed For SaleAgent Provided
04/16/2004$2,125,000Sold
N/A
10/17/1988$875,000Sold
N/A

Market trends in Weston

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
Sale-to-List Price
Price per sq ft
Available listings
62
8
MoM
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Property Tax and Assessment

Year2025
Tax$60,575
Assessment$5,457,200
Home facts updated by county records

Comparable Sales for 55 Chestnut St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
0.16
Single-Family Home
$3,350,000
08/29/25
5
5
6,252
0.28
Single-Family Home
$7,255,000
10/02/25
5
6.5
8,205
0.81
Single-Family Home
$4,900,000
06/11/26
5
7
8,363
0.19
Single-Family Home
$11,000,000
12/04/25
7
10
12,120
0.55
Single-Family Home
$6,600,000
03/31/26
5
7.5
11,300
0.88
Single-Family Home
$5,700,000
12/02/25
5
6
8,210
0.49
Single-Family Home
$2,600,000
11/17/25
5
3.5
5,100
0.93
Single-Family Home
$3,750,000
01/15/26
6
6.5
9,064
0.48
Single-Family Home
$1,930,000
08/22/25
4
3
3,760
1.23
Single-Family Home
$7,180,000
06/24/26
6
7.5
8,421

Nearby homes

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Assigned Schools

These are the assigned schools for 55 Chestnut St.
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

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. "
  • 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."
  • 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. "
  • 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."
  • 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."
  • 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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Off Market Homes Near 55 Chestnut St

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