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

$7,417,200

Trulia Estimate
  • 5 Beds
  • 6.5 Baths
  • 8,205 sqft (on 3.39 acres)

100 Chestnut St, Weston, MA 02493

Est. Refi. Payment $46,275/mo*
Refinance Your Home
Currently Off Market - Sold Oct 2, 2025 for $7,255,000

Home Value

Trulia Estimate
$7.42M
Since last month
Decreased$33K (-0.4%)
Since last year
Decreased$529K (-6.6%)
Since last sale
Increased$170K (+2.3%)
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 +65% in the last 10 years
MonthEstimated value
2026
September 2026$7.43M
August 2026$7.46M
July 2026$7.45M
June 2026$7.31M
May 2026$7.31M
April 2026$7.25M
March 2026$7.26M
February 2026$7.33M
January 2026$7.23M
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
180 Highland St, Weston, MA
0.38
Single-Family Home
$6,600,000
03/31/26
5
7.5
11,300
72 Love Ln, Weston, MA
0.60
Single-Family Home
$5,700,000
12/02/25
5
6
8,210
6 Baldwin Cir, Weston, MA
0.31
Single-Family Home
$4,850,000
08/26/26
4
4.5
5,858
9 Sanderson Ln, Weston, MA
0.56
Single-Family Home
$4,900,000
06/11/26
5
7
8,363
21 Chestnut St, Weston, MA
0.47
Single-Family Home
$11,000,000
12/04/25
7
10
12,120
42 Westerly Rd, Weston, MA
0.68
Single-Family Home
$3,750,000
01/15/26
6
6.5
9,064
10 Audubon Rd, Weston, MA
0.80
Single-Family Home
$3,500,000
03/30/26
5
5.5
5,409
286 Country Dr, Weston, MA
1.16
Single-Family Home
$7,180,000
06/24/26
6
7.5
8,421
137 Wellesley St, Weston, MA
0.74
Single-Family Home
$2,600,000
11/17/25
5
3.5
5,100

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
0.22
$1,847,600
5
3.5
3,112
Off Market
73 Chestnut St, Weston, MA 02493
0.23
$9,450,000
7
10
12,461
For Sale
25 Livermore Ln, Weston, MA 02493
0.26
$1,455,000
3
2.5
2,899
Recently Sold
148 Highland St, Weston, MA 02493
0.24
$6,580,100
5
8
11,412
Off Market
1 Livermore Ln #1, Weston, MA 02493
0.30
-
3
2.5
1,216
Off Market
6 Baldwin Cir, Weston, MA 02493
0.31
$4,850,000
4
4.5
5,858
Recently Sold
16 Livermore Ln #16, Weston, MA 02493
0.32
$1,750,000
3
3
4,030
Recently Sold
23 Pine Summit Cir, Weston, MA 02493
0.35
$3,159,125
3
3.5
4,438
Recently Sold
8 Cutting Ln, Weston, MA 02493
0.36
$2,637,500
3
3.5
2,803
Off Market
48 Golden Ball Rd, Weston, MA 02493
0.38
$1,309,200
3
2.5
1,800
Off Market
27 Pine Summit Cir #27, Weston, MA 02493
0.37
-
4
5
5,000
Off Market

Local Information

  • Map ViewExplore the area around 100 Chestnut St.
  • Schools2 Preschool Schools3 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1992
3.39 acre lot
8,205 sqft
$904/sqft
3 Car Garage

About this House

What's unique:Secluded acresTennis courtStone wallsRolling landscapesSecluded ground-floor primary suiteBlue stone terraces
100 Chestnut Street is the epitome of New England privacy & elegance. This estate is nestled on 3.3 secluded acres in scenic Weston. The home offers the charm of rolling landscapes, stone walls, and lush gardens. Designed by Royal Barry Wills & extensively renovated, this home showcases stunning interiors with 10'-14' ceilings, a Christopher Peacock kitchen, limestone fireplaces, herringbone oak floors, & French doors leading to blue stone terraces. The expertly crafted layout features a secluded ground-floor primary suite as well as expansive 2nd-floor bedrooms, ideal for both family living & entertaining. Surrounded by hundreds of acres conservation land, the property boasts exceptional amenities including a tennis court, pool, and expansive lawns. Enjoy access to pristine trails for hiking, biking & horseback riding. Located just 20 minutes from Boston and minutes from Weston Center, this smart home with Control 4 automation promises modern convenience in a picturesque setting.
100 Chestnut St, Weston, MA 02493 is a 5 bedroom, 7 bathroom, 8,205 sqft single-family home built in 1992. It last sold for $7,255,000 on Oct 2, 2025 (9% below the $7,995,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $7,417,200.
Last check for updates: about 11 hours ago
Listed by The Mazer Group, (617) 905-7379
Compass, (617) 206-3333
Allison Mazer, (617) 905-7379
Bought with: Antonio Khoury, (781) 385-1695, Compass, (617) 206-3333
Source: MLS PIN, MLS#73433821

Home Details for 100 Chestnut St

Interior Features

Interior Details
Number of Rooms: 13Types of Rooms: Master Bathroom
Beds & Baths
Number of Bedrooms: 5Number of Bathrooms: 7Number of Bathrooms (full): 6Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 8205 Square Feet
Heating & Cooling
Heating: Forced Air,Natural GasHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air
Fireplace & Spa
Number of Fireplaces: 4Has a FireplaceNo Spa

Exterior Features

Exterior Home Features
Patio / Porch: Patio, EnclosedExterior: Patio, Patio - Enclosed, Pool - Inground Heated, Tennis Court(s), Garden, Stone WallFoundation: Concrete PerimeterGardenHas a Private Pool
Parking & Garage
Number of Garage Spaces: 3Number of Covered Spaces: 3Open Parking Spaces: 5No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 8Parking: Attached,Driveway
Pool
Pool: Pool - Inground HeatedPool
Frontage
Not on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 8205

Property Information

Year Built
Year Built: 1992
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Cape
Building
Not Attached PropertyDoes Not Include Home Warranty
Property Information
Parcel Number: M:031.0 L:0006 S:000.0, 868171

Price & Status

Price
List Price: $7,995,000
Status Change & Dates
Off Market Date: Thu Sep 25 2025

Active Status

MLS Status: Sold

Location

Direction & Address
City: Weston

Building

Building Area
Building Area: 8205 Square Feet

Community

Not Senior Community

HOA

No HOA

Lot Information

Lot Area: 3.3874 Acres

Offer

Contingencies: Pending P&S

Miscellaneous

Mls Number: 73433821Above Grade Unfinished Area: 8205

Price and Tax history

DateEventPrice
Oct 2, 2025
Source: MLS PIN #73433821
Sold
$7,255,000
Sep 23, 2025
Source: MLS PIN #73433821
Contingent
$7,995,000
Sep 22, 2025
Source: MLS PIN #73433821
Listed For Sale
$7,995,000
Aug 19, 2025
Source: MLS PIN #73331634
ListingRemoved
$7,995,000
Jun 4, 2025
Source: MLS PIN #73331634
PriceChange
$7,995,000
Price decreased by 5%

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

The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information are for the personal, non commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein.
The MLS listing information displayed is deemed reliable, but is not guaranteed accurate by the MLS.

Frequently asked questions about 100 Chestnut St

  • What is 100 Chestnut St estimated to be worth?
    Trulia's estimated value for 100 Chestnut St in Weston, MA is $7,417,200.
  • What is the price history for 100 Chestnut St?
    100 Chestnut St in Weston, MA last sold for $7,255,000 in October 2025.
  • 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.
  • Does 100 Chestnut St have air conditioning?
    Yes, 100 Chestnut St in Weston, MA has air conditioning.
  • Does 100 Chestnut St have a pool?
    Yes, 100 Chestnut St in Weston, MA has a pool.

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