56 Chestnut St, Weston, MA 02493
Property image
Property image
OFF MARKET

$4,115,800

Trulia Estimate
  • 5 Beds
  • 6 Baths
  • 6,695 sqft (on 2.32 acres)

56 Chestnut St, Weston, MA 02493

Est. Refi. Payment $25,534/mo*
Refinance Your Home
Currently Off Market - Sold Dec 18, 2015 for $2,600,000

Home Value

Trulia Estimate
$4.12M
Since last month
Increased$43K (+1.1%)
Since last year
Increased$153K (+3.9%)
Since last sale
Increased$2M (+57.9%)
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 +50% in the last 10 years
MonthEstimated value
2026
September 2026$4.1M
August 2026$4.06M
July 2026$4.15M
June 2026$4.17M
May 2026$4.14M
April 2026$4.05M
March 2026$4.09M
February 2026$3.93M
January 2026$3.86M
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
0.18
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
137 Wellesley St, Weston, MA
0.58
Single-Family Home
$2,600,000
11/17/25
5
3.5
5,100
180 Highland St, Weston, MA
0.47
Single-Family Home
$6,600,000
03/31/26
5
7.5
11,300
21 Chestnut St, Weston, MA
0.24
Single-Family Home
$11,000,000
12/04/25
7
10
12,120
10 Audubon Rd, Weston, MA
0.90
Single-Family Home
$3,500,000
03/30/26
5
5.5
5,409
9 Sanderson Ln, Weston, MA
0.74
Single-Family Home
$4,900,000
06/11/26
5
7
8,363
72 Love Ln, Weston, MA
0.85
Single-Family Home
$5,700,000
12/02/25
5
6
8,210
42 Westerly Rd, Weston, MA
0.86
Single-Family Home
$3,750,000
01/15/26
6
6.5
9,064
142 Buckskin Dr, Wayland, MA
1.11
Single-Family Home
$2,495,000
06/15/26
5
4.5
5,886

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
74 Chestnut St, Weston, MA 02493
0.08
$1,847,600
5
3.5
3,112
Off Market
73 Chestnut St, Weston, MA 02493
0.12
$9,450,000
7
10
12,461
For Sale
6 Baldwin Cir, Weston, MA 02493
0.18
$4,850,000
4
4.5
5,858
Recently Sold
21 Chestnut St, Weston, MA 02493
0.24
$11,000,000
7
10
12,120
Recently Sold
22 Chadwick Rd, Weston, MA 02493
0.26
$3,409,800
5
5
6,252
Off Market
100 Chestnut St, Weston, MA 02493
0.28
$7,417,200
5
6.5
8,205
Off Market
171 Wellesley St, Weston, MA 02493
0.39
$3,159,900
6
4
4,936
Off Market
148 Highland St, Weston, MA 02493
0.45
$6,580,100
5
8
11,412
Off Market
48 Golden Ball Rd, Weston, MA 02493
0.50
$1,309,200
3
2.5
1,800
Off Market
46 Golden Ball Rd, Weston, MA 02493
0.51
$964,500
3
1.5
920
Off Market
180 Highland St, Weston, MA 02493
0.47
$6,600,000
5
7.5
11,300
Recently Sold
25 Livermore Ln, Weston, MA 02493
0.53
$1,455,000
3
2.5
2,899
Recently Sold

Local Information

  • Map ViewExplore the area around 56 Chestnut St.
  • Schools2 Preschool Schools3 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 2007
2.32 acre lot
6,695 sqft
$615/sqft

About this House

A chic design characterizes this exceptional home located in a coveted Southside neighborhood. The lifestyle of quiet elegance is appreciated with its picturesque setting encompassing over 2 acres and protected by stone walls and conservation land. A renowned New England architect masterfully blends a casual open floor plan with formal entertaining. A designer kitchen, paneled walnut library and second floor media room are special interior attributes. State of the art smart house technology, Carlisle wood floors and timeless millwork are examples of the high quality detail throughout. Convenient to Boston, schools and airports, enjoy the comfort and quality of this architectural gem.
56 Chestnut St, Weston, MA 02493 is a 5 bedroom, 7 bathroom, 6,695 sqft single-family home built in 2007. It last sold for $2,600,000 on Dec 18, 2015. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $4,115,800.

Home Details for 56 Chestnut St

Interior Features

Interior Details
BasementNumber of Rooms: 11
Heating & Cooling
Heating: Forced Air, GasAir ConditioningHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Wood

Property Information

Year Built
Year Built: 2007
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 2.32 acres

Price and Tax history

DateEventPrice
Dec 18, 2015
Source: N/A
Sold
$2,600,000
Nov 4, 2015
Source: Agent Provided
Pending
$2,998,000
Oct 15, 2015
Source: Agent Provided
PendingToActive
$2,998,000
Oct 7, 2015
Source: Agent Provided
Pending
$2,998,000
Jul 22, 2015
Source: Agent Provided
PriceChange
$2,998,000
Price decreased by 6%

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
    Flag
  • 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."
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 56 Chestnut St

  • What is 56 Chestnut St estimated to be worth?
    Trulia's estimated value for 56 Chestnut St in Weston, MA is $4,115,800.
  • What is the price history for 56 Chestnut St?
    56 Chestnut St in Weston, MA last sold for $2,600,000 in December 2015.
  • Is Weston a buyer's or seller's market?
    Weston is currently a seller's market, based on recent for-sale activity.
  • What do residents say about Weston?
    Residents describe Weston, MA as dog-friendly, quiet, and easy to park in. Most residents say you need a car. See recently sold homes in Weston, MA.
  • How big is the lot at 56 Chestnut St?
    The lot at 56 Chestnut St in Weston, MA is about 2.3 acres.

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