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

56 Chestnut St
Weston, MA 02493

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

$4,167,300

Trulia Estimate
as of Jul 8, 2026

$4,167,300

Trulia Estimate
as of Jul 8, 2026
5 Beds
6 Baths
6,695 sqft
(on 2.32 acres)

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

Description

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. It is currently off market. The Trulia Estimate is $4,167,300, with a rent estimate of $13,732/month.

Home Highlights

Parking
No Info
Outdoor
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

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 History for 56 Chestnut St

DatePriceEventSource
12/18/2015$2,600,000Sold
N/A
11/04/2015$2,998,000PendingAgent Provided
10/15/2015$2,998,000PendingToActiveAgent Provided
10/07/2015$2,998,000PendingAgent Provided
07/22/2015$2,998,000PriceChange
Agent Provided
05/11/2015$3,198,000PriceChange
Agent Provided
04/11/2015$3,450,000PriceChange
Agent Provided
08/29/2014$3,695,000PriceChange
Agent Provided
05/05/2014$3,950,000Listed For SaleAgent Provided
06/18/2008$3,600,000Sold
N/A
05/28/2004$1,200,000Sold
N/A

Market trends in Weston

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
70
14MoM
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Property Tax and Assessment

Year2025
Tax$35,127
Assessment$3,164,600
Home facts updated by county records

Comparable Sales for 56 Chestnut St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
22 Chadwick Rd, Weston, MA
0.26
Single-Family Home
$3,350,000
08/29/25
5
5
6,252
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
148 Highland St, Weston, MA
0.45
Single-Family Home
$6,500,000
07/15/25
5
8
11,412
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
142 Wellesley St, Weston, MA
0.57
Single-Family Home
$1,930,000
08/22/25
4
3
3,760
39 Westerly Rd, Weston, MA
0.93
Single-Family Home
$3,287,500
08/22/25
5
3.5
6,461

Nearby homes

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Assigned Schools

These are the assigned schools for 56 Chestnut St.
View nearby schools on GreatSchools
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. "
    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."
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  • 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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Apartments for Rent

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Explore by feature - Pet Friendly

8 pet-friendly rentals in Weston, MA

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8 rentals with air conditioning in Weston, MA

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Homes for sale near 56 Chestnut St

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Off Market Homes Near 56 Chestnut St

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