5 Chiltern Rd, Weston, MA 02493
OFF MARKET

$2,204,800

Trulia Estimate
  • 4 Beds
  • 3.5 Baths
  • 2,765 sqft (on 0.33 acres)

5 Chiltern Rd, Weston, MA 02493

Est. Refi. Payment $13,149/mo*
Refinance Your Home
Currently Off Market - Sold Aug 25, 2008 for $1,215,000

Home Value

Trulia Estimate
$2.21M
Since last month
Decreased$35K (-1.6%)
Since last year
Increased$69K (+3.2%)
Since last sale
Increased$990K (+81.5%)
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 +60% in the last 10 years
MonthEstimated value
2026
August 2026$2.2M
July 2026$2.24M
June 2026$2.28M
May 2026$2.31M
April 2026$2.25M
March 2026$2.21M
February 2026$2.13M
January 2026$2.07M
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
0.12
Single-Family Home
$1,975,000
01/06/26
5
4
2,614
25 Riverdale Rd, Wellesley, MA
0.40
Single-Family Home
$1,895,000
08/19/26
4
3
2,695
92 Woodlawn Ave, Wellesley, MA
0.58
Single-Family Home
$1,953,000
06/03/26
4
2.5
2,627
54 Colburn Rd, Wellesley, MA
0.65
Single-Family Home
$1,655,000
01/30/26
4
2.5
2,204
11 Grayson Ln, Newton, MA
0.63
Single-Family Home
$1,400,000
11/26/25
4
2.5
2,685
16 Intervale Rd, Wellesley, MA
0.48
Single-Family Home
$1,415,000
05/15/26
3
2.5
2,127
25 Columbia St, Wellesley, MA
0.63
Single-Family Home
$1,290,000
12/11/25
6
3
2,667
2 Longfellow Rd, Wellesley, MA
0.82
Single-Family Home
$1,740,000
03/23/26
4
3.5
2,664
7 Crescent St, Wellesley, MA
0.75
Single-Family Home
$1,975,000
12/10/25
4
2.5
2,533
80 Washington St, Wellesley, MA
0.75
Single-Family Home
$1,665,000
07/17/26
5
4
3,096

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
0.12
$3,361,600
5
6
5,680
Off Market
8 Old Town Rd, Wellesley, MA 02481
0.12
$1,975,000
5
4
2,614
Recently Sold
45 Chiltern Rd, Weston, MA 02493
0.14
$1,961,900
-
-
-
Off Market
37 Boulder Rd, Wellesley, MA 02481
0.14
$2,882,800
4
3
3,990
Off Market
33 Boulder Rd, Wellesley, MA 02481
0.17
$1,695,000
-
-
-
For Sale
50 Crestwood Dr, Wellesley, MA 02481
0.20
$2,883,400
5
5.5
4,361
Off Market
135 Glen Rd, Wellesley, MA 02481
0.20
$3,492,500
5
4
5,093
Off Market
243 Ridgeway Rd, Weston, MA 02493
0.19
$3,139,500
4
5
4,624
Off Market
121 Glen Rd, Wellesley, MA 02481
0.24
$4,739,600
5
5.5
4,586
Off Market
153 Ridgeway Rd, Weston, MA 02493
0.30
$3,750,000
5
5
5,387
Recently Sold
32 Intervale Rd, Weston, MA 02493
0.33
$2,299,000
4
3.5
4,200
Recently Sold
116 Glen Rd, Wellesley, MA 02481
0.29
$2,119,200
4
5
4,442
Off Market

Local Information

  • Map ViewExplore the area around 5 Chiltern Rd.
  • Schools2 Preschool Schools3 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1925
Lot Size
0.33 acres
Living Area
2,765 sqft
Price/Sqft
$797
Parking
Garage

About this House

Garrison Colonial in charming southside neighborhood. This four bedroom home with Marvin windows, central air, and two car garage features a spacious kitchen with breakfast nook, granite countertops, subzero fridge and gas cooktop. Mudroom with lots of storage. Bright sunny master bath in Carrera marble. Family room opens out to porch overlooking spectacular professionally landscaped level yard.
5 Chiltern Rd, Weston, MA 02493 is a 4 bedroom, 4 bathroom, 2,765 sqft single-family home built in 1925. It last sold for $1,215,000 on Aug 25, 2008. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,204,800, with a rent estimate of $6,302/month.

Home Details for 5 Chiltern Rd

Interior Features

Interior Details
BasementNumber of Rooms: 9Types of Rooms: Breakfast Nook, Dining Room, Family Room, Master Bath, Mud RoomCeiling Fan
Heating & Cooling
Heating: Baseboard, Radiant, GasAir ConditioningCooling System: CentralHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 3Floors: Carpet, Hardwood
Appliances & Utilities
DishwasherDisposalDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
FireplaceJetted Bath Tub
Windows, Doors, Floors & Walls
Double Paned Windows

Exterior Features

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

Property Information

Year Built
Year Built: 1925Year Updated: 1996
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 0.33 acres

Price and Tax history

DateEventPrice
Aug 25, 2008
Source: N/A
Sold
$1,215,000
Jul 16, 2008
Source: Agent Provided
PriceChange
$1,290,000
Price decreased by 7%
Jun 19, 2008
Source: Agent Provided
Listed For Sale
$1,385,000
Aug 2, 1994
Source: N/A
Sold
$440,000

Market trends in Weston

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
57
5MoM

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
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LGBTQ Local Legal Protections

Frequently asked questions about 5 Chiltern Rd

  • What is 5 Chiltern Rd estimated to be worth?
    Trulia's estimated value for 5 Chiltern Rd in Weston, MA is $2,204,800.
  • What is the price history for 5 Chiltern Rd?
    5 Chiltern Rd in Weston, MA last sold for $1,215,000 in August 2008.
  • 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 5 Chiltern Rd have air conditioning?
    Yes, 5 Chiltern Rd in Weston, MA has air conditioning.
  • Does 5 Chiltern Rd have laundry facilities?
    Yes, 5 Chiltern Rd in Weston, MA has in-unit laundry.

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