81 Chestnut St, Weston, MA 02493
OFF MARKET

81 Chestnut St
Weston, MA 02493

  • 5 Beds
  • 7 Baths
  • 8,438 sqft (on 2.03 acres)

$6,954,200

Trulia Estimate
as of Aug 6, 2026
Est. Refi. Payment $41,643/mo*
Refinance Your Home

$6,954,200

Trulia Estimate
as of Aug 6, 2026
Est. Refi. Payment $41,643/mo*
Refinance Your Home
5 Beds
7 Baths
8,438 sqft
(on 2.03 acres)

Local Information

  • Map ViewExplore the area around 81 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
2002
Lot Size
2.03 acres
Living Area
8,438 sqft
Price/Sqft
$824

About this House

This single-family home is located at 81 Chestnut St, Weston, MA. 81 Chestnut St is in Weston, MA and in ZIP code 02493. This property has 5 bedrooms, 7 bathrooms and approximately 8,438 sqft of floor space. This property has a lot size of 2.03 acres and was built in 2002.
81 Chestnut St, Weston, MA 02493 is a 5 bedroom, 7 bathroom, 8,438 sqft single-family home built in 2002. It last sold for $2,400,000 on Jul 30, 2001. It is currently off market. The Trulia Estimate is $6,954,200, with a rent estimate of $22,147/month.

Home Details for 81 Chestnut St

Interior Features

Interior Details
BasementNumber of Rooms: 15
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: 2002
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 2.03 acres

Price History for 81 Chestnut St

DatePriceEventSource
07/30/2001$2,400,000Sold
N/A
08/06/1990$1,000,000Sold
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
8MoM
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Property Tax and Assessment

Year2025
Tax$66,924
Assessment$6,029,200
Home facts updated by county records

Comparable Sales for 81 Chestnut St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
100 Chestnut St, Weston, MA
0.15
Single-Family Home
$7,255,000
10/02/25
5
6.5
8,205
22 Chadwick Rd, Weston, MA
0.28
Single-Family Home
$3,350,000
08/29/25
5
5
6,252
180 Highland St, Weston, MA
0.45
Single-Family Home
$6,600,000
03/31/26
5
7.5
11,300
9 Sanderson Ln, Weston, MA
0.68
Single-Family Home
$4,900,000
06/11/26
5
7
8,363
72 Love Ln, Weston, MA
0.74
Single-Family Home
$5,700,000
12/02/25
5
6
8,210
21 Chestnut St, Weston, MA
0.33
Single-Family Home
$11,000,000
12/04/25
7
10
12,120
137 Wellesley St, Weston, MA
0.61
Single-Family Home
$2,600,000
11/17/25
5
3.5
5,100
42 Westerly Rd, Weston, MA
0.80
Single-Family Home
$3,750,000
01/15/26
6
6.5
9,064
10 Audubon Rd, Weston, MA
0.88
Single-Family Home
$3,500,000
03/30/26
5
5.5
5,409
39 Westerly Rd, Weston, MA
0.87
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 81 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. "
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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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LGBTQ Local Legal Protections

Apartments for Rent

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Explore by feature - Pet Friendly

8 pet-friendly rentals in Weston, MA

Explore by feature - Garage

Explore by feature - Air Conditioning

6 rentals with air conditioning in Weston, MA

Explore by feature - Washer/dryer

10 rentals with a washer/dryer in Weston, MA

Explore by feature - Outdoor Space

6 rentals with an outdoor space in Weston, MA

Homes for sale near 81 Chestnut St

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Off Market Homes Near 81 Chestnut St

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Frequently asked questions about 81 Chestnut St

  • What is 81 Chestnut St estimated to be worth?
    Trulia's estimated value for 81 Chestnut St in Weston, MA is $6,954,200.
  • What is the price history for 81 Chestnut St?
    81 Chestnut St in Weston, MA last sold for $2,400,000 in July 2001.
  • 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 81 Chestnut St?
    The lot at 81 Chestnut St in Weston, MA is about 2 acres.