205 Winter St, Weston, MA 02493
OFF MARKET

$1,742,900

Trulia Estimate
  • 4 Beds
  • 3 Baths
  • 2,319 sqft (on 4.23 acres)

205 Winter St, Weston, MA 02493

Est. Refi. Payment $10,383/mo*
Refinance Your Home

Home Value

Trulia Estimate
$1.74M
Since last month
Decreased$57K (-3.2%)
Since last year
Increased$65K (+3.8%)
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 +64% in the last 10 years
MonthEstimated value
2026
August 2026$1.75M
August 2026$1.74M
July 2026$1.81M
June 2026$1.8M
May 2026$1.83M
April 2026$1.82M
March 2026$1.75M
February 2026$1.69M
January 2026$1.65M
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
620 South Ave, Weston, MA
0.55
Single-Family Home
$1,920,000
03/12/26
4
4
4,041
556 Wellesley St, Weston, MA
0.60
Single-Family Home
$1,710,000
05/18/26
4
2.5
2,596
30 Radcliffe Rd, Weston, MA
0.47
Single-Family Home
$1,788,000
02/03/26
5
3.5
5,482
43 Sherburn Cir, Weston, MA
0.84
Single-Family Home
$1,700,000
06/10/26
3
2.5
2,554
169 Hickory Rd, Weston, MA
0.73
Single-Family Home
$2,695,000
07/17/26
5
3
5,328
199 Country Dr, Weston, MA
0.75
Single-Family Home
$2,480,000
06/16/26
6
4
3,907
54 Woodchester Dr, Weston, MA
0.80
Single-Family Home
$2,600,000
10/22/25
4
3.5
4,130
482 Glen Rd, Weston, MA
0.84
Single-Family Home
$2,635,000
02/19/26
5
4.5
5,142
419 Wellesley St, Weston, MA
0.96
Single-Family Home
$3,560,000
06/05/26
5
4
5,372
16 Wayland Hills Rd, Wayland, MA
1.03
Single-Family Home
$1,365,000
06/27/26
4
2.5
2,964

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
11 Beaver Rd, Weston, MA 02493
0.12
$2,738,200
4
3
3,580
Off Market
181 Winter St, Weston, MA 02493
0.14
$2,008,900
5
3.5
3,034
Off Market
24 Sylvan Ln, Weston, MA 02493
0.21
$8,539,100
6
8
10,100
Off Market
15 Dickson Ln #15, Weston, MA 02493
0.27
-
3
2.5
2,777
Off Market
53 Beaver Rd, Weston, MA 02493
0.26
$2,954,000
4
3.5
4,136
Off Market
2 Dickson Ln, Weston, MA 02493
0.28
$1,221,600
3
3.5
2,930
Off Market
680 South Ave #8, Weston, MA 02493
0.31
$1,379,000
3
2.5
2,764
Off Market
680 South Ave #3, Weston, MA 02493
0.31
$1,330,400
3
3.5
2,586
Off Market
5 Upham Way #5, Weston, MA 02493
0.30
$1,459,000
3
2.5
3,240
Recently Sold
7 Upham Way #4, Weston, MA 02493
0.31
-
3
3.5
3,130
Off Market
680 South Ave #7, Weston, MA 02493
0.34
$1,560,000
3
3.5
3,536
Recently Sold
52 Sylvan Ln, Weston, MA 02493
0.30
$3,792,700
5
4
5,241
Off Market

Local Information

  • Map ViewExplore the area around 205 Winter St.
  • Schools2 Preschool Schools3 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1938
4.23 acre lot
2,319 sqft
$752/sqft
Garage

About this House

Original house is Red Cedar log construction from 1938. Expanded in 1957 and 1969 with vertical Cedar tongue-in-groove and planking additions. Sited on 4+ wooded acres with stream and pond. Extensive gardens and in-ground swimming pool.
205 Winter St, Weston, MA 02493 is a 4 bedroom, 3 bathroom, 2,319 sqft single-family home built in 1938. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,742,900, with a rent estimate of $5,271/month.

Home Details for 205 Winter St

Interior Features

Heating & Cooling
Heating: GasAir ConditioningCooling System: CentralHeating Fuel: Gas
Levels, Entrance, & Accessibility
Stories: 1Floors: Tile, Carpet
Interior Details
AtticNumber of Rooms: 9Types of Rooms: Dining Room, Family Room, Laundry Room, Master BathWet BarCeiling Fan
Appliances & Utilities
Cable ReadyDishwasherDisposalDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace
Windows, Doors, Floors & Walls
Double Paned Windows
Security
Security System

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: WoodGardenLawnPatioPorch
Pool
Pool
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1938Year Updated: 1957
Property Type / Style
Property Type: Single Family HomeArchitecture: Ranch / Rambler

Community

Units in Building: 1

Lot Information

Lot Area: 4.23 acres

Price and Tax history

YearProperty taxTax assessment
2025
$15,126
$1,362,700
Home facts updated by county records

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
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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."
    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."
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LGBTQ Local Legal Protections

Frequently asked questions about 205 Winter St

  • What is 205 Winter St estimated to be worth?
    Trulia's estimated value for 205 Winter St in Weston, MA is $1,742,900.
  • 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.
  • What are the closest schools to 205 Winter St?
    The closest schools to 205 Winter St in Weston, MA are Country Elementary School (Pre-K, rated 10/10), Field Elementary School (rated 8/10), Weston High School (rated 10/10).
  • Does 205 Winter St have air conditioning?
    Yes, 205 Winter St in Weston, MA has air conditioning.
  • Does 205 Winter St have a pool?
    Yes, 205 Winter St in Weston, MA has a pool.

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