2 Pine St, Winchester, MA 01890
OFF MARKET

2 Pine St
Winchester, MA 01890

  • 6 Beds
  • 3.5 Baths
  • 4,034 sqft (on 0.44 acres)

$2,377,100

Trulia Estimate
as of May 31, 2026
Est. Refi. Payment $13,711/mo*
Refinance Your Home

$2,377,100

Trulia Estimate
as of May 31, 2026
Est. Refi. Payment $13,711/mo*
Refinance Your Home
6 Beds
3.5 Baths
4,034 sqft
(on 0.44 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

Welcome to 2 Pine Street, originally known as the Conant house. Don't miss this once in a lifetime opportunity to own one of Winchester's most iconic properties situated just outside the town center! Zoned as a two family, this majestic Colonial & Italianate revival-style home can also be reconfigured as a gorgeously ornate family home by itself or with an already existing apartment, perfect for an in-law or au pair suite. Inside the home, you'll immediately notice the incredible craftsmanship throughout, including soaring ceilings, leaded glass windows, fireplace & period detailing. Perhaps the most special bonus to this property is its large barn, an incredible piece of living history! Formally a working barn for horses, this generous space could accommodate multiple vehicles & includes a vast upstairs area, ready for imaginative renovation ideas. Located in walking distance to everything Winchester has to offer! This one-of-a-kind home is truly one of Winchester's finest gems!
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
Garage
Outdoor
Porch, Deck
A/C
Heating only
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 2 Pine St

Interior Features

Interior Details
BasementNumber of Rooms: 9Types of Rooms: Dining Room
Heating & Cooling
Heating: Other, GasHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 3Floors: Tile, Hardwood, Linoleum Vinyl
Appliances & Utilities
DishwasherDryerMicrowaveRefrigerator
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: SlateDeckExterior: WoodPorch
Parking & Garage
GarageParking Spaces: 5Parking: Garage Detached

Property Information

Year Built
Year Built: 1880
Property Type / Style
Property Type: TownhouseArchitecture: Conventional

Community

Units in Building: 2

Lot Information

Lot Area: 0.44 acres

Price History for 2 Pine St

DatePriceEventSource
12/10/2020$1,599,000Sold
N/A
10/07/2020$1,649,000PendingAgent Provided
09/24/2020$1,649,000Listed For SaleAgent Provided
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Property Tax and Assessment

Year2025
Tax$21,684
Assessment$1,955,300
Home facts updated by county records

Comparable Sales for 2 Pine St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
63 Church St #63, Winchester, MA
0.03
Townhouse
$1,100,000
06/27/25
4
2.5
3,157
4 Wyman Ct #4, Winchester, MA
0.15
Townhouse
$1,399,000
01/05/26
4
4.5
2,500
209 Washington St #209, Winchester, MA
0.72
Townhouse
$1,499,000
12/24/25
5
3.5
3,141
6 Wyman Ct #6, Winchester, MA
0.15
Townhouse
$1,379,000
01/05/26
3
4.5
2,722
20 Fletcher St #20, Winchester, MA
0.21
Townhouse
$1,400,000
07/14/25
3
2.5
2,282
36 Middlesex St #36, Winchester, MA
0.43
Townhouse
$1,380,000
02/26/26
4
3.5
2,259
31 Mystic Ave #31, Winchester, MA
0.37
Townhouse
$1,200,000
05/29/26
4
2
2,129
35 Rumford St #35, Winchester, MA
0.70
Townhouse
$1,635,000
07/11/25
4
2.5
2,470
83 Canal St #83, Winchester, MA
0.69
Townhouse
$1,149,000
07/31/25
4
2.5
2,300
162 Swanton St #162, Winchester, MA
0.73
Townhouse
$1,199,000
11/21/25
3
3.5
2,459

Nearby homes

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Assigned Schools

These are the assigned schools for 2 Pine St.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

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
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  • 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
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  • marta3467
    "Can see kids playing ball in street; people walking their dog and Horn Pond and several nice restaurants all within walking distance"
    1
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2 Pine St, Winchester, MA 01890 is a 6 bedroom, 4 bathroom, 4,034 sqft townhouse built in 1880. This property is not currently available for sale. 2 Pine St was last sold on Dec 10, 2020 for $1,599,000. The current Trulia Estimate for 2 Pine St is $2,377,100.