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$1,249,900 Just Listed

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 2 Full Baths
  • 1 Partial Bath
  • 2,454 Sq. Ft.
  • 0.16 Acres
  • Updated 1 day ago
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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!

Full Property Details for 40 Pickering St

General

  • Price: $1,249,900
  • Taxes: $11,312 (2025)
  • Status: Active
  • Type: Single Family
  • MLS ID: 73484617
  • Updated: 3/10/2026
  • Added to Site: 2 day(s) ago

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 2
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 4

Location

  • County: Middlesex

Structural Information

  • Architectural Style: Colonial
  • Square Feet: 2,454
  • Year Built: 1870

Lot Features

  • Lot Size (Acres): 0.16

Financial Considerations

  • Tax Amount: $11,312
  • Tax Year: 2025

Disclosures and Reports

  • Disclosures/Rstr.: Central air system does not go into kitchen/family room. Small area of old, inactive insect damage in basement. Some photos are digitally altered.
  • Property ID: M:014 B:0180 L:0, 898516

Listed by Keller Williams Realty Signature Properties, Timothy Haynes

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Listing agent

— 40 Pickering St —

  • Timothy Haynes

    Keller Williams Realty Signature Properties

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 40 Pickering St

School District:Winchester School District, Winchester, MA
NameGradesDistance
Lynch Elementary School
10 Brantwood Road, Winchester, MA 01890
K-50.3 mi
Mccall Middle School
458 Main Street, Winchester, MA 01890
6-81.2 mi
Winchester High School
80 Skillings Road, Winchester, MA 01890
9-120.9 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 40 Pickering St Get Price Alerts and Save Property

Date
Details
Price
Change
Source
3/10/2026
Listed
$1,249,900
113.66%
MLS
1/11/2017
Sold
$585,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 40 Pickering St

Year
Property Taxes
Change
Tax Assessment
Change
2025
$11,312
3%
$1,020,000
6%
2024
$10,950
2%
$966,500
7%
2023
$10,683
1%
$905,300
7%
2022
$10,616
6%
$848,600
9%
2021
$9,996
4%
$779,100
—
2020
$9,653
14%
$779,100
11%
2019
$8,501
2%
$702,000
3%
2018
$8,301
19%
$681,000
20%
2017
$6,950
9%
$566,000
4%
2016
$6,382
2%
$546,400
6%
2015
$6,284
6%
$517,600
11%
2014
$5,915
—
$467,200
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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NMLS#: 1598647

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Listed by Keller Williams Realty Signature Properties, Timothy Haynes

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40 Pickering St, Winchester, MA 01890 (MLS# 73484617) is a Single Family property with 4 bedrooms, 2 full bathrooms and 1 partial bathroom. 40 Pickering St is currently listed for $1,249,900 and was received on March 10, 2026. Want to learn more about 40 Pickering St? Do you have questions about finding other Single Family real estate for sale in Winchester Highlands? You can browse all Winchester Highlands real estate or contact a Coldwell Banker agent to request more information.

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