40 Pickering St, Winchester, MA 01890
Property image
Property image
SOLD
APR 14, 2026

$1,345,400

Trulia Estimate
  • 4 Beds
  • 2.5 Baths
  • 2,454 sqft

40 Pickering St, Winchester, MA 01890

Est. Refi. Payment $8,382/mo*
Refinance Your Home
Currently Off Market - Sold Apr 14, 2026 for $1,330,000 (6% above list price)

Home Value

Trulia Estimate
$1.34M
Since last month
Increased$4K (+0.3%)
Since last year
Increased$225K (+20.1%)
Since last sale
Increased$19K (+1.5%)
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 +82% in the last 10 years
MonthEstimated value
2026
September 2026$1.35M
August 2026$1.35M
July 2026$1.34M
June 2026$1.33M
May 2026$1.33M
April 2026$1.33M
March 2026$1.19M
February 2026$1.13M
January 2026$1.11M
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
9 Sylvester Ct, Winchester, MA
0.12
Single-Family Home
$1,015,000
12/01/25
4
1.5
2,001
112 Wendell St, Winchester, MA
0.21
Single-Family Home
$1,335,000
02/04/26
4
3
2,854
149 Horn Pond Brook Rd, Winchester, MA
0.23
Single-Family Home
$1,020,000
06/05/26
5
2
2,331
136 Sylvester Ave, Winchester, MA
0.13
Single-Family Home
$1,156,000
02/25/26
3
1.5
1,608
87 Wendell St, Winchester, MA
0.30
Single-Family Home
$1,250,000
05/29/26
4
2
2,046
104 Wendell St, Winchester, MA
0.25
Single-Family Home
$1,100,000
05/28/26
3
1.5
1,675
10 Farrow St, Winchester, MA
0.38
Single-Family Home
$1,660,000
08/07/26
4
3.5
2,768
28 Arlington St, Woburn, MA
0.42
Single-Family Home
$1,299,000
02/24/26
4
3.5
3,000
76 Woodside Rd, Winchester, MA
0.40
Single-Family Home
$1,080,000
05/12/26
4
2
1,552

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
38 Pickering St #A, Winchester, MA 01890
0.01
$1,082,000
3
2.5
2,056
Recently Sold
5 Lake Cir, Woburn, MA 01801
0.09
$700,000
-
-
-
For Sale
49 Sheridan Cir, Winchester, MA 01890
0.06
$2,409,000
5
4.5
5,881
Recently Sold
20 Lake Ave, Woburn, MA 01801
0.12
$768,700
3
2
1,892
Off Market
26 Lake Ave, Woburn, MA 01801
0.13
$748,800
3
2
1,665
Off Market
23-25 Glenwood Ave, Winchester, MA 01890
0.09
-
3
2
1,625
Off Market
2 Maria Ct, Woburn, MA 01801
0.17
$780,000
2
2
1,824
Recently Sold
136 Sylvester Ave, Winchester, MA 01890
0.13
$1,156,000
3
1.5
1,608
Recently Sold
9 Sylvester Ct, Winchester, MA 01890
0.12
$1,015,000
4
1.5
2,001
Recently Sold
5 Sylvester Ct, Winchester, MA 01890
0.13
$1,404,400
4
2
2,280
Off Market
16 Glenwood Ave, Winchester, MA 01890
0.12
$1,820,000
6
4.5
6,900
Recently Sold

Local Information

  • Map ViewExplore the area around 40 Pickering St.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1870
2,454 sqft
$542/sqft
2 Parking Spaces

About this House

This charming home retains period details while delivering flexible modern living. Through the glass-enclosed front porch, the first floor offers an entry stair hall, formal living room, a bedroom or home office with full bath and separate entrance, kid's homework room/drop zone, and - the star of the show - a sun-drenched open plan kitchen/family room with fireplace, massive island, and plenty of space for entertaining. Upstairs, there are three more bedrooms, a full bath and a half-bath, plus laundry and a sitting/play room. However you decide to use the 2400+sf, there's plenty of it. The roof, siding, water line and many windows were new when the sellers bought in 2017. Since then, they have installed new wiring, plumbing, heating and air conditioning. They re-did the kitchen and bathrooms. The floors are refinished, paint refreshed, and insulation upgraded. Outside, the sunny corner lot is partially fenced. Come take a look!
40 Pickering St, Winchester, MA 01890 is a 4 bedroom, 3 bathroom, 2,454 sqft single-family home built in 1870. It last sold for $1,330,000 on Apr 14, 2026 (6% above the $1,249,900 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,345,400, with a rent estimate of $4,787/month.
Last check for updates: about 14 hours ago
Listed by Timothy Haynes, (617) 905-3917
Keller Williams Realty Signature Properties, (781) 924-5766
Bought with: Bernadine Tsung Megason, (310) 562-3608, Dreamega International Realty LLC, (617) 655-9357
Source: MLS PIN, MLS#73484617

Home Details for 40 Pickering St

Interior Features

Interior Details
Number of Rooms: 8
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 3Number of Bathrooms (full): 2Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 2454 Square Feet
Heating & Cooling
Heating: Baseboard,Hot Water,PropaneHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Baseboard
Fireplace & Spa
Number of Fireplaces: 1Has a FireplaceNo Spa

Exterior Features

Exterior Home Features
Foundation: Stone
Parking & Garage
Open Parking Spaces: 2No GarageParking Spaces: 2
Frontage
Not on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 2454

Property Information

Year Built
Year Built: 1870
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial
Building
Not Attached PropertyDoes Not Include Home Warranty
Property Information
Parcel Number: M:014 B:0180 L:0, 898516

Price & Status

Price
List Price: $1,249,900Price Per Sqft: $542/sqft
Status Change & Dates
Off Market Date: Mon Mar 16 2026

Active Status

MLS Status: Sold

Location

Direction & Address
City: Winchester

Building

Building Area
Building Area: 2454 Square Feet

Community

Not Senior Community

HOA

No HOA

Lot Information

Lot Area: 6965 sqft

Offer

Contingencies: Pending P&S

Miscellaneous

Mls Number: 73484617Above Grade Unfinished Area: 2454

Price and Tax history

DateEventPrice
Apr 14, 2026
Source: MLS PIN #73484617
Sold
$1,330,000
Mar 12, 2026
Source: MLS PIN #73484617
Contingent
$1,249,900
Mar 10, 2026
Source: MLS PIN #73484617
Listed For Sale
$1,249,900
Oct 27, 2017
Source: N/A
Sold
$670,000
Sep 11, 2017
Source: Agent Provided
Pending
$679,000

Market trends in Winchester

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
62
2MoM

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

The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information are for the personal, non commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein.
The MLS listing information displayed is deemed reliable, but is not guaranteed accurate by the MLS.

Frequently asked questions about 40 Pickering St

  • What is 40 Pickering St estimated to be worth?
    Trulia's estimated value for 40 Pickering St in Winchester, MA is $1,345,400.
  • What is the price history for 40 Pickering St?
    40 Pickering St in Winchester, MA last sold for $1,330,000 in April 2026.
  • Is Winchester a buyer's or seller's market?
    Winchester is currently a buyer's market, based on recent for-sale activity.
  • What do residents say about Winchester?
    Residents describe Winchester, MA as dog-friendly, well-kept, and easy to park in. Most residents say you need a car. See recently sold homes in Winchester, MA.
  • Does 40 Pickering St have air conditioning?
    Yes, 40 Pickering St in Winchester, MA has air conditioning.
  • How big is the lot at 40 Pickering St?
    The lot at 40 Pickering St in Winchester, MA is about 0.16 acres (6,965 sq ft).

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