2 Pilgrim Dr, Winchester, MA 01890
OFF MARKET

$1,608,300

Trulia Estimate
  • 4 Beds
  • 3 Baths
  • 2,725 sqft (on 0.71 acres)

2 Pilgrim Dr, Winchester, MA 01890

Est. Refi. Payment $9,587/mo*
Refinance Your Home
Currently Off Market - Sold Nov 16, 2007 for $675,000

Home Value

Trulia Estimate
$1.61M
Since last month
Decreased$44K (-2.7%)
Since last year
Increased$11K (+0.7%)
Since last sale
Increased$935K (+138.5%)
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 +59% in the last 10 years
MonthEstimated value
2026
August 2026$1.61M
August 2026$1.61M
July 2026$1.65M
June 2026$1.66M
May 2026$1.71M
April 2026$1.65M
March 2026$1.65M
February 2026$1.57M
January 2026$1.51M
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
59 Johnson Rd, Winchester, MA
0.10
Single-Family Home
$1,165,000
10/14/25
3
2.5
2,458
9 Pilgrim Dr, Winchester, MA
0.11
Single-Family Home
$1,725,000
09/19/25
3
2.5
2,541
29 Pilgrim Dr, Winchester, MA
0.25
Single-Family Home
$1,700,000
06/29/26
5
3
3,271
189 High St, Winchester, MA
0.41
Single-Family Home
$1,191,000
01/13/26
4
3
2,126
8 Hawthorne Rd, Winchester, MA
0.14
Single-Family Home
$1,775,000
08/21/26
5
3
3,315
94 Johnson Rd, Winchester, MA
0.41
Single-Family Home
$1,715,000
09/03/26
4
3
3,366
10 Olde Lyme Rd, Winchester, MA
0.17
Single-Family Home
$1,600,000
10/10/25
5
3.5
3,478
205 Ridge St, Winchester, MA
0.41
Single-Family Home
$1,550,000
10/31/25
5
3
2,995
44 Amberwood Dr, Winchester, MA
0.48
Single-Family Home
$1,713,000
09/26/25
3
2.5
3,002
10 Hawthorne Rd, Winchester, MA
0.16
Single-Family Home
$2,100,000
03/19/26
5
4.5
3,191

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
50 Johnson Rd, Winchester, MA 01890
0.04
$1,682,100
3
3
2,646
Off Market
5 Pilgrim Dr, Winchester, MA 01890
0.06
$2,419,100
6
3.5
4,138
Off Market
54 Johnson Rd, Winchester, MA 01890
0.07
$3,100,000
5
7.5
6,899
Recently Sold
59 Johnson Rd, Winchester, MA 01890
0.10
$1,393,600
3
2.5
2,458
Off Market
9 Pilgrim Dr, Winchester, MA 01890
0.11
$1,770,500
3
2.5
2,541
Off Market
8 Hawthorne Rd, Winchester, MA 01890
0.14
$1,775,000
5
3
3,315
Recently Sold
7 Russett Ln, Winchester, MA 01890
0.14
$2,703,600
5
6
7,292
Off Market
10 Hawthorne Rd, Winchester, MA 01890
0.16
$2,100,000
5
4.5
3,191
Recently Sold
8 Olde Lyme Rd, Winchester, MA 01890
0.17
$2,058,000
5
3.5
4,603
Off Market
10 Olde Lyme Rd, Winchester, MA 01890
0.17
$1,645,800
5
3.5
3,478
Off Market
4 Olde Lyme Rd, Winchester, MA 01890
0.17
$1,940,600
4
4
3,488
Off Market
12 Olde Lyme Rd, Winchester, MA 01890
0.18
$2,558,500
5
4.5
4,215
Off Market

Local Information

  • Map ViewExplore the area around 2 Pilgrim Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1961
0.71 acre lot
2,725 sqft
$590/sqft
Garage

About this House

This single-family home is located at 2 Pilgrim Dr, Winchester, MA. 2 Pilgrim Dr is in Winchester, MA and in ZIP code 01890. This property has 4 bedrooms, 3 bathrooms and approximately 2,725 sqft of floor space. This property has a lot size of 0.71 acres and was built in 1961.
2 Pilgrim Dr, Winchester, MA 01890 is a 4 bedroom, 3 bathroom, 2,725 sqft single-family home built in 1961. It last sold for $675,000 on Nov 16, 2007. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,608,300, with a rent estimate of $6,297/month.

Home Details for 2 Pilgrim Dr

Interior Features

Interior Details
BasementNumber of Rooms: 7
Heating & Cooling
Heating: OilHeating Fuel: Oil
Levels, Entrance, & Accessibility
Stories: 1
Fireplace & Spa
Fireplace

Exterior Features

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

Property Information

Year Built
Year Built: 1961
Property Type / Style
Property Type: Single Family HomeArchitecture: split level

Community

Units in Building: 1

Lot Information

Lot Area: 0.71 acres

Price and Tax history

DateEventPrice
Nov 16, 2007
Source: N/A
Sold
$675,000

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

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
    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 2 Pilgrim Dr

  • What is 2 Pilgrim Dr estimated to be worth?
    Trulia's estimated value for 2 Pilgrim Dr in Winchester, MA is $1,608,300.
  • What is the price history for 2 Pilgrim Dr?
    2 Pilgrim Dr in Winchester, MA last sold for $675,000 in November 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.
  • How big is the lot at 2 Pilgrim Dr?
    The lot at 2 Pilgrim Dr in Winchester, MA is about 0.71 acres (30,927 sq ft).
  • Does 2 Pilgrim Dr have a garage?
    Yes, 2 Pilgrim Dr in Winchester, MA has a garage.

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