21 Chiltern Rd, Weston, MA 02493
Property image
Property image
OFF MARKET

$2,115,100

Trulia Estimate
  • 4 Beds
  • 4 Baths
  • 4,520 sqft (on 0.71 acres)

21 Chiltern Rd, Weston, MA 02493

Est. Refi. Payment $13,158/mo*
Refinance Your Home
Currently Off Market - Sold Jul 8, 2016 for $1,259,300

Home Value

Trulia Estimate
$2.12M
Since last month
Decreased$18K (-0.8%)
Since last year
Increased$64K (+3.1%)
Since last sale
Increased$855K (+67.9%)
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 +67% in the last 10 years
MonthEstimated value
2026
September 2026$2.11M
August 2026$2.13M
July 2026$2.17M
June 2026$2.21M
May 2026$2.22M
April 2026$2.16M
March 2026$2.14M
February 2026$2.07M
January 2026$2.02M
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
8 Old Town Rd, Wellesley, MA
0.14
Single-Family Home
$1,975,000
01/06/26
5
4
2,614
32 Intervale Rd, Weston, MA
0.31
Single-Family Home
$2,299,000
11/10/25
4
3.5
4,200
25 Riverdale Rd, Wellesley, MA
0.41
Single-Family Home
$1,895,000
08/19/26
4
3
2,695
50 Hubbard Rd, Weston, MA
0.43
Single-Family Home
$2,100,000
10/15/25
4
3.5
3,220
8 Blake Rd, Weston, MA
0.66
Single-Family Home
$1,085,000
07/17/26
5
3.5
4,932
25 Hillside Rd, Wellesley, MA
0.63
Single-Family Home
$2,280,000
08/28/26
5
5.5
4,453
21 Elm St, Wellesley, MA
0.75
Single-Family Home
$2,690,000
07/16/26
4
3.5
4,761
33 Hundreds Cir, Wellesley, MA
0.66
Single-Family Home
$3,900,000
08/14/26
5
3.5
5,074
153 Ridgeway Rd, Weston, MA
0.28
Single-Family Home
$3,750,000
07/08/26
5
5
5,387
135 Orchard Ave, Weston, MA
0.38
Single-Family Home
$4,170,000
04/02/26
5
4.5
4,340

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
40 Chiltern Rd, Weston, MA 02493
0.11
$3,332,500
5
6
5,680
Off Market
8 Old Town Rd, Wellesley, MA 02481
0.14
$1,975,000
5
4
2,614
Recently Sold
45 Chiltern Rd, Weston, MA 02493
0.12
$1,946,800
-
-
-
Off Market
37 Boulder Rd, Wellesley, MA 02481
0.16
$2,865,400
4
3
3,990
Off Market
50 Crestwood Dr, Wellesley, MA 02481
0.21
$2,908,200
5
5.5
4,361
Off Market
135 Glen Rd, Wellesley, MA 02481
0.21
$3,518,100
5
4
5,093
Off Market
243 Ridgeway Rd, Weston, MA 02493
0.20
$3,147,600
4
5
4,624
Off Market
121 Glen Rd, Wellesley, MA 02481
0.26
$4,757,700
5
5.5
4,586
Off Market
153 Ridgeway Rd, Weston, MA 02493
0.28
$3,750,000
5
5
5,387
Recently Sold
32 Intervale Rd, Weston, MA 02493
0.31
$2,495,100
4
3.5
4,200
Off Market
116 Glen Rd, Wellesley, MA 02481
0.31
$2,124,400
4
5
4,442
Off Market
39 River Glen Rd, Wellesley, MA 02481
0.36
$1,995,000
4
2.5
2,820
For Sale

Local Information

  • Map ViewExplore the area around 21 Chiltern Rd.
  • Schools2 Preschool Schools3 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1957
0.71 acre lot
4,520 sqft
$468/sqft
Garage

About this House

executive ranch with oversized rooms
21 Chiltern Rd, Weston, MA 02493 is a 4 bedroom, 4 bathroom, 4,520 sqft single-family home built in 1957. It last sold for $1,259,300 on Jul 8, 2016. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,115,100, with a rent estimate of $7,101/month.

Home Details for 21 Chiltern Rd

Interior Features

Interior Details
BasementAtticNumber of Rooms: 12Types of Rooms: Walk In Closet, Breakfast Nook, Dining Room, Family Room, Master Bath, Office, Recreation Room
Heating & Cooling
Heating: Baseboard, Forced Air, GasAir ConditioningCooling System: CentralHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 2Floors: Tile, Hardwood
Appliances & Utilities
Cable ReadyDishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace
Windows, Doors, Floors & Walls
Double Paned Windows
Security
Security System

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: BrickLawnPatioSprinkler System
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached, Off Street

Property Information

Year Built
Year Built: 1957Year Updated: 2016
Property Type / Style
Property Type: Single Family HomeArchitecture: Ranch / Rambler

Community

Units in Building: 1

Lot Information

Lot Area: 0.71 acres

Additional Information

Sport Court

Price and Tax history

DateEventPrice
Jul 8, 2016
Source: N/A
Sold
$1,259,300
May 7, 2016
Source: Agent Provided
Pending
$1,339,000
Mar 29, 2016
Source: Agent Provided
PriceChange
$1,339,000
Price decreased by 3%
Feb 10, 2016
Source: Agent Provided
Listed For Sale
$1,379,000
Sep 27, 2015
Source: Agent Provided
ListingRemoved
$1,379,000

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
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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."
    0
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LGBTQ Local Legal Protections

Frequently asked questions about 21 Chiltern Rd

  • What is 21 Chiltern Rd estimated to be worth?
    Trulia's estimated value for 21 Chiltern Rd in Weston, MA is $2,115,100.
  • What is the price history for 21 Chiltern Rd?
    21 Chiltern Rd in Weston, MA last sold for $1,259,300 in July 2016.
  • 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 21 Chiltern Rd have air conditioning?
    Yes, 21 Chiltern Rd in Weston, MA has air conditioning.
  • Does 21 Chiltern Rd have laundry facilities?
    Yes, 21 Chiltern Rd in Weston, MA has in-unit laundry.

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