100 Winchester St #2, Brookline, MA 02446
Property image
Property image
OFF MARKET

$2,026,300

Trulia Estimate
  • 4 Beds
  • 3 Baths
  • 2,564 sqft

100 Winchester St #2, Brookline, MA 02446

Corey Hill
Est. Refi. Payment $12,075/mo*
Refinance Your Home
Currently Off Market - Sold Oct 30, 2015 for $1,200,000

Home Value

Trulia Estimate
$2.03M
Since last month
Decreased$25K (-1.2%)
Since last year
Decreased$123K (-5.7%)
Since last sale
Increased$826K (+68.9%)
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$2.03M
August 2026$2.02M
July 2026$2.05M
June 2026$2.05M
May 2026$2.03M
April 2026$2M
March 2026$1.98M
February 2026$1.93M
January 2026$1.86M
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
151 Mason Ter #2, Brookline, MA
0.05
Condo
$2,150,000
10/23/25
4
3.5
2,704
17 Summit Ave #2, Brookline, MA
0.15
Condo
$2,400,000
07/15/26
4
2.5
2,454
373 Harvard St #1, Brookline, MA
0.18
Condo
$1,525,000
02/18/26
3
2.5
2,035
200 Winchester St #1, Brookline, MA
0.24
Condo
$1,650,000
03/31/26
3
3
2,820
50 Winchester St #413, Brookline, MA
0.10
Condo
$1,500,000
04/23/26
3
2.5
1,242
93 Centre St #2, Brookline, MA
0.11
Condo
$1,220,000
01/28/26
3
2
1,465
32 Columbia St, Brookline, MA
0.19
Condo
$1,995,000
05/15/26
3
3
2,063
32 Columbia St #1, Brookline, MA
0.19
Condo
$1,995,000
05/15/26
3
3
2,047
138 Mason Ter #1, Brookline, MA
0.09
Condo
$1,635,000
12/08/25
3
2
1,804
49 Winchester St #2, Brookline, MA
0.12
Condo
$1,250,000
05/26/26
3
2
1,377

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
65 Atherton Rd, Brookline, MA 02446
0.02
$2,650,000
6
3.5
3,277
Recently Sold
62 Atherton Rd #2, Brookline, MA 02446
0.04
$2,081,300
4
2
2,222
Off Market
151 Mason Ter #A, Brookline, MA 02446
0.05
-
4
5
3,745
Off Market
151 Mason Ter #2, Brookline, MA 02446
0.05
-
4
3.5
2,704
Off Market
106 Winchester St #2, Brookline, MA 02446
0.01
$828,600
2
1
1,165
Off Market
66 Winchester St #101, Brookline, MA 02446
0.08
$1,463,200
3
2
1,719
Off Market
66 Winchester St #203, Brookline, MA 02446
0.08
$1,138,800
2
2
1,236
Off Market
99 Winchester St #4, Brookline, MA 02446
0.03
$2,849,500
3
2.5
2,174
Off Market
66 Winchester St #PHB, Brookline, MA 02446
0.08
-
2
2
1,311
Off Market
103 Winchester St #1, Brookline, MA 02446
0.03
$1,564,100
3
2.5
1,734
Off Market
105 Winchester St #3, Brookline, MA 02446
0.03
$1,722,300
3
2
1,750
Off Market
148 Mason Ter #2, Brookline, MA 02446
0.07
$2,235,900
4
2.5
2,276
Off Market

Local Information

  • Map ViewExplore the area around 100 Winchester St #2.
  • Schools1 Preschool School2 Elementary Schools2 Middle Schools1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Condo
Built in 1898
2,564 sqft
$790/sqft
Garage

About this House

Spacious, light filled duplex condo in desirable Coolidge Corner! First showings at open house Sunday September 13 from 1:30-3:30 Four bed/3 bath + home office! Period detail, high ceilings, second and third floor of a two family home. French doors with cozy family room; fireplace in living room, bay windows, recessed lighting, central air and in unit laundry. Kitchen has breakfast nook. Home office could also be guest room as has easy access to one of the three full baths. All three (non master) bedrooms are good sized with their own shared bath and all bedrooms on same floor as master bedroom. Amazing closet space. Master bedroom has master bath AND a walk in closet. Private front porch "tree top" deck! Fenced back yard with shared patio + gardens and one car garage parking. Move right in to this lovingly cared for home in a great location! Please submit offers by Wednesday September 16 @ 7 PM.
100 Winchester St #2, Brookline, MA 02446 is a 4 bedroom, 3 bathroom, 2,564 sqft condo in Corey Hill, built in 1898. It last sold for $1,200,000 on Oct 30, 2015. More recently, it was listed as a rental in November 2023 with an asking price of $7,000 per month. That rental listing was removed on December 26, 2023. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,026,300.

Home Details for 100 Winchester St #2

Interior Features

Heating & Cooling
Heating: Forced AirAir ConditioningHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Number of Rooms: 9
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: SlateExterior: Wood
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1898
Property Type / Style
Property Type: CondoArchitecture: Other

Community

Units in Building: 2

Price and Tax history

DateEventPrice
Dec 26, 2023
Source: Zillow Rentals
ListingRemoved
Nov 13, 2023
Source: Zillow Rentals
Listed For Rent
$7,000
Oct 30, 2015
Source: N/A
Sold
$1,200,000
Sep 9, 2015
Source: Agent Provided
Listed For Sale
$1,100,000
Aug 23, 1999
Source: N/A
Sold
$540,000

Market trends in Brookline

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.22M
$182KMoM
Sale-to-List Price
99.7%
0.2%MoM
Price per sq ft
$816
$19MoM
Available listings
216
37MoM

Around this home

Neighborhood Overview

Corey Hill
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about Corey Hill

At least 48 Trulia users voted on each feature.

  • 100 % Say there are sidewalks

  • 97 % Say it's walkable to grocery stores

  • 96 % Say it's walkable to restaurants

  • 95 % Say it's dog friendly

  • 88 % Say people would walk alone at night

  • 84 % Say streets are well-lit

  • 77 % Say there's wildlife

  • 71 % Say kids play outside

  • 67 % Say there's holiday spirit

  • 62 % Say neighbors are friendly

  • 58 % Say parking is easy

  • 48 % Say they plan to stay for at least 5 years

  • 45 % Say there are community events

  • 45 % Say it's quiet

  • 28 % Say yards are well-kept

  • 22 % Say car is needed

Sourced by Trulia users. Learn more about our methodology.
  • Trulia User
    "Very dog friendly "
    0
    Flag
  • Trulia User
    "I’v stayed in a hotel in this neighborhood. It is a beautiful area with many shops to explore. Hope to move to this area. "
    0
    Flag
  • Pat B.
    "It's dog friendly...there's lots of parks around to take pets."
    0
    Flag
  • Pat B.
    "The commute is pretty easy. The train is pretty reliable around here so it makes getting to and from the area pretty simple. I wish there were more buses though."
    0
    Flag
  • Pat B.
    "The closeness of the transportation is great. All of the major green lines are very close to Corey Hill and it makes getting around very easy."
    3
    Flag
  • Pat B.
    "There's some strange people who are around, but they're harmless. There's lots of daycare places, so if someone has a young kid there's lots of options nearby."
    1
    Flag
  • Tkesav
    "corey hill is near coolidge corner. yoy can see skyline of Boston..close to Trader Joes, Wholefoods, Fenway,."
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 100 Winchester St #2

  • What is 100 Winchester St #2 estimated to be worth?
    Trulia's estimated value for 100 Winchester St #2 in Brookline, MA is $2,026,300.
  • What is the price history for 100 Winchester St #2?
    100 Winchester St #2 in Brookline, MA last sold for $1,200,000 in October 2015.
  • Is Brookline a buyer's or seller's market?
    Brookline is currently a buyer's market, based on recent for-sale activity.
  • What's the median sale price in Brookline?
    The median sale price in Brookline is $1.22M. That is down $182K from the prior month.

Explore by feature - Pet Friendly

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Explore by feature - Pool

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Explore by feature - Outdoor Space

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Apartments for Rent

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Off Market Homes Near 100 Winchester St #2

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