3 Cobblestone Dr, Winchester, MA 01890
OFF MARKET

3 Cobblestone Dr
Winchester, MA 01890

  • 3 Beds
  • 2.5 Baths
  • 3,591 sqft

$1,446,100

Trulia Estimate
as of Aug 24, 2026
Est. Refi. Payment $8,574/mo*
Refinance Your Home

$1,446,100

Trulia Estimate
as of Aug 24, 2026
Est. Refi. Payment $8,574/mo*
Refinance Your Home
3 Beds
2.5 Baths
3,591 sqft

Home Value

Trulia Estimate
$1.45M
Since last month
Decreased$8K (-0.6%)
Since last year
Increased$20K (+1.4%)
Since last sale
Increased$710K (+96.6%)
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 +62% in the last 10 years
MonthEstimated value
2026
August 2026$1.45M
July 2026$1.45M
June 2026$1.45M
May 2026$1.46M
April 2026$1.46M
March 2026$1.44M
February 2026$1.41M
January 2026$1.37M
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
171 Swanton St #58, Winchester, MA
0.28
Condo
$800,000
05/05/26
2
3
1,833
9 Charles Rd, Winchester, MA
0.33
Condo
$681,888
03/25/26
3
1.5
968
7 Conant Rd #53, Winchester, MA
0.42
Condo
$745,000
06/02/26
2
2
1,588
1 Conn St #1, Woburn, MA
0.53
Condo
$599,900
09/09/25
3
2
1,798
7 Conant Rd #33, Winchester, MA
0.42
Condo
$680,000
03/16/26
2
2
1,532
17 Charles Rd, Winchester, MA
0.32
Condo
$645,000
06/16/26
2
2
987
7 Conant Rd #20, Winchester, MA
0.41
Condo
$665,000
11/14/25
2
2
1,168
666 Main St #312, Winchester, MA
0.64
Condo
$750,000
02/05/26
2
2
1,240
18-20 Buck St #1, Woburn, MA
0.64
Condo
$609,000
07/31/26
4
1.5
1,308
666 Main St #206, Winchester, MA
0.64
Condo
$710,000
09/10/25
2
2
1,170

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
17 Russell Rd, Winchester, MA 01890
0.07
$1,098,000
3
1.5
1,657
For Sale
8-10 Russell Rd, Winchester, MA 01890
0.08
$960,000
4
2
1,800
Recently Sold
104 Wendell St, Winchester, MA 01890
0.12
$1,100,000
3
1.5
1,675
Recently Sold
112 Wendell St, Winchester, MA 01890
0.13
$1,335,000
4
3
2,854
Recently Sold
41 White St, Winchester, MA 01890
0.09
$1,529,600
4
3
2,442
Off Market
25 Shepard Ct #25, Winchester, MA 01890
0.10
$1,279,600
4
3.5
3,340
Off Market
96 Hemingway St, Winchester, MA 01890
0.12
$745,300
3
1.5
1,140
Off Market
8 Glenwood Ave #8, Winchester, MA 01890
0.13
-
3
2.5
2,225
Off Market
118 Wendell St, Winchester, MA 01890
0.15
$1,686,200
5
3
3,415
Off Market
21 Shepard Ct #21, Winchester, MA 01890
0.11
$731,600
2
1
1,393
Off Market
87 Wendell St, Winchester, MA 01890
0.14
$1,250,000
4
2
2,046
Recently Sold
16 Hemingway St, Winchester, MA 01890
0.13
$1,169,300
3
2.5
2,017
Off Market

Local Information

  • Map ViewExplore the area around 3 Cobblestone Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Condo
Year Built
2006
Living Area
3,591 sqft
Price/Sqft
$403
Parking
Garage

About this House

This condo is located at 3 Cobblestone Dr, Winchester, MA. 3 Cobblestone Dr is in Winchester, MA and in ZIP code 01890. This property has 3 bedrooms, 3 bathrooms and approximately 3,591 sqft of floor space. This property was built in 2006.
3 Cobblestone Dr, Winchester, MA 01890 is a 3 bedroom, 3 bathroom, 3,591 sqft condo built in 2006. It last sold for $735,000 on Apr 13, 2007. It is currently off market. The Trulia Estimate is $1,446,100, with a rent estimate of $5,801/month.

Home Details for 3 Cobblestone Dr

Interior Features

Interior Details
BasementAtticNumber of Rooms: 8Types of Rooms: Walk In Closet, Breakfast Nook, Dining Room, Family Room, Laundry Room, Master Bath, Office, Pantry, Recreation RoomCeiling Fan
Heating & Cooling
Heating: Forced Air, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Carpet, Hardwood
Appliances & Utilities
Cable ReadyDishwasherDisposalDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
FireplaceJetted Bath Tub
Windows, Doors, Floors & Walls
Double Paned Windows
Security
Security System

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: WoodLawnPatioSprinkler System
Parking & Garage
GarageParking Spaces: 5Parking: Garage Attached, Off Street, On Street

Property Information

Year Built
Year Built: 2006
Property Type / Style
Property Type: CondoArchitecture: townhouse

Community

Units in Building: 1

Price and Tax history

DateEventPrice
Apr 13, 2007
Source: N/A
Sold
$735,000

Market trends in Winchester

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.47M
$62.83KMoM
Sale-to-List Price
101.9%
0.2%MoM
Price per sq ft
$574
$3MoM
Available listings
64
13MoM

Around this home

What Locals Say about Winchester

At least 93 Trulia users voted on each feature.

  • 92 % Say it's dog friendly

  • 88 % Say yards are well-kept

  • 87 % Say people would walk alone at night

  • 85 % Say parking is easy

  • 79 % Say there are sidewalks

  • 79 % Say car is needed

  • 77 % Say it's walkable to restaurants

  • 77 % Say kids play outside

  • 75 % Say streets are well-lit

  • 74 % Say there's holiday spirit

  • 67 % Say they plan to stay for at least 5 years

  • 67 % Say there's wildlife

  • 66 % Say neighbors are friendly

  • 65 % Say it's walkable to grocery stores

  • 64 % Say it's quiet

  • 54 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Diana P.
    "Winchester is the cutest town, perfect for families. There is Town Say, and Enka, and everything is very family oriented. We even have great pubs/restaurants as well as sub shops, Greek food, nail salons, anything you could want in a home town!"
    7
    Flag
  • Dominic
    "Phenomenal public school system beginning from Kindergarten and extremely welcoming to new residents transferring in."
    0
    Flag
  • Stacie
    "Very family oriented. Not a great neighborhood if you don’t have children. Great, easy commute into the city. Not enough good restaurants that aren’t overpriced though. "
    0
    Flag
  • Yjchoi7
    "Very safe neighborhood.there are often summer events on the common. Teenagers can take train into Boston area fairly easily as there are two stops within Winchester. Fells is a great place for summer walks. "
    2
    Flag
  • Luis B.
    "perfect for my family It is livable stores Closer to me Barbershop computer store Restaurants I will love to buy a house in this area "
    2
    Flag
  • Yjchoiyjchoi
    "It’s very quiet and safe generally. Yet it’s close to Boston and Cambridge city life within a few stops of the commuter from Winchester. "
    0
    Flag
  • Tara
    "I have lived in this neighborhood for 25 years. I love it. Everybody is friendly and kind. The crime is minimal and it’s very quiet. "
    2
    Flag
  • Katie41287
    "I’m not afraid to walk home at 11pm, the town is clean and has plenty of events around town, the people are friendly and it is near public transportation. "
    1
    Flag
  • Anna S.
    "Excellent school Easy commute to Boston Downtown Great parks and pond nearby"
    0
    Flag
  • tod g.
    "Lovely town with easy access to Boston and easy getaway to northern New England."
    0
    Flag
  • jfrancis6
    "Family community built around three streets that form a circle that only has traffic of residents. The area borders the Town of Winchester forest that is great for walks and snow shoeing in winter. All homes are large and attract families were children can safely play and bike in the neighborhood. Many homes have residents who grow up in the neighborhood as children and returned to raise their families. A short walk 4/10 of a mile to train station for those who work in Boston a trip that takes 12 minutes with only one stop. Schools in Winchester are among the best in Massachusetts, a primary attraction to the Town. The Town center is only one mile away and has an addition train station there as well. The Mystic lakes are just beyond the train station with a Town beach and boating opportunities. The Town also borders a 2500 acre forest known as the Fells consisting of the Town water supply and miles of hiking or mountain biking."
    0
    Flag
  • marta3467
    "Can see kids playing ball in street; people walking their dog and Horn Pond and several nice restaurants all within walking distance"
    1
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 3 Cobblestone Dr

  • What is 3 Cobblestone Dr estimated to be worth?
    Trulia's estimated value for 3 Cobblestone Dr in Winchester, MA is $1,446,100.
  • What is the price history for 3 Cobblestone Dr?
    3 Cobblestone Dr in Winchester, MA last sold for $735,000 in April 2007.
  • Is Winchester a buyer's or seller's market?
    Winchester is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Winchester?
    The median sale price in Winchester is $1.47M. That is up $62.83K from the prior month.
  • Does 3 Cobblestone Dr have air conditioning?
    Yes, 3 Cobblestone Dr in Winchester, MA has air conditioning.
  • Does 3 Cobblestone Dr have laundry facilities?
    Yes, 3 Cobblestone Dr in Winchester, MA has in-unit laundry.

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