19 Pilgrim Dr, Winchester, MA 01890
OFF MARKET

$1,803,400

Trulia Estimate
  • 5 Beds
  • 3.5 Baths
  • 3,150 sqft (on 0.47 acres)

19 Pilgrim Dr, Winchester, MA 01890

Est. Refi. Payment $11,308/mo*
Refinance Your Home
Currently Off Market - Sold Aug 15, 2025 for $1,775,000

Home Value

Trulia Estimate
$1.8M
Since last month
Decreased$8K (-0.4%)
Since last year
Increased$21K (+1.1%)
Since last sale
Increased$31K (+1.7%)
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 +66% in the last 10 years
MonthEstimated value
2026
September 2026$1.81M
August 2026$1.81M
July 2026$1.81M
June 2026$1.78M
May 2026$1.78M
April 2026$1.76M
March 2026$1.77M
February 2026$1.79M
January 2026$1.76M
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
29 Pilgrim Dr, Winchester, MA
0.10
Single-Family Home
$1,700,000
06/29/26
5
3
3,271
8 Hawthorne Rd, Winchester, MA
0.30
Single-Family Home
$1,775,000
08/21/26
5
3
3,315
10 Olde Lyme Rd, Winchester, MA
0.25
Single-Family Home
$1,600,000
10/10/25
5
3.5
3,478
64 Westland Ave, Winchester, MA
0.25
Single-Family Home
$2,050,000
10/15/25
4
4
3,716
10 Hawthorne Rd, Winchester, MA
0.31
Single-Family Home
$2,100,000
03/19/26
5
4.5
3,191
2 Olde Lyme Rd, Winchester, MA
0.31
Single-Family Home
$1,857,000
09/15/26
3
3.5
2,513
205 Ridge St, Winchester, MA
0.57
Single-Family Home
$1,550,000
10/31/25
5
3
2,995
61 Westland Ave, Winchester, MA
0.30
Single-Family Home
$1,800,000
02/24/26
3
3.5
2,785
59 Johnson Rd, Winchester, MA
0.27
Single-Family Home
$1,165,000
10/14/25
3
2.5
2,458
34 Robinhood Rd, Winchester, MA
0.33
Single-Family Home
$1,450,000
06/12/26
4
2.5
3,380

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
9 Pilgrim Dr, Winchester, MA 01890
0.06
$1,760,600
3
2.5
2,541
Off Market
7 Russett Ln, Winchester, MA 01890
0.07
$2,700,000
5
6
7,292
Off Market
16 Johnson Rd, Winchester, MA 01890
0.09
$1,732,400
3
2
3,142
Off Market
29 Pilgrim Dr, Winchester, MA 01890
0.10
$1,700,000
5
3
3,271
Recently Sold
5 Pilgrim Dr, Winchester, MA 01890
0.12
$2,403,600
6
3.5
4,138
Off Market
21 Johnson Rd, Winchester, MA 01890
0.11
$1,868,800
4
2.5
2,814
Off Market
19 Johnson Rd, Winchester, MA 01890
0.12
$2,058,400
5
3.5
4,318
Off Market
8 Johnson Rd, Winchester, MA 01890
0.16
$2,334,000
6
5.5
5,800
Off Market
1 Socrates Way, Winchester, MA 01890
0.19
$2,043,100
5
3.5
5,123
Off Market
3 Socrates Way, Winchester, MA 01890
0.19
$1,260,700
4
2.5
2,570
Off Market
50 Johnson Rd, Winchester, MA 01890
0.21
$1,673,100
3
3
2,646
Off Market

Local Information

  • Map ViewExplore the area around 19 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
0.47 acre lot
3,150 sqft
$573/sqft
2 Car Garage

About this House

What's unique:Swimming poolPool houseComposite decksOversized family roomOpen-concept dining areaCul-de-sac-like neighborhood
Your very own private oasis tucked away in a cul-de-sac-like neighborhood just mins. to Winchester Center! Set on a deep, tree-lined lot, this stunning home offers 5 beds, 3.5 baths, & over 3,000 sq. ft. The versatile floor plan offers ground-level entry w/ a 2 car garage, 2 bedrooms (which can also function as work/play space,) & full bath/laundry area. The upper level is the heart of the home – The spacious living room w/ a wood-burning F/P & vaulted ceilings flows effortlessly into the open-concept dining area. The gourmet kitchen, anchored by a large center island, offers timeless finishes including sleek cabinetry, quartz, & S/S appliances. An oversized family room w/ abundant natural lighting completes the main living area. The opposite wing features 3 bedrooms & 2 full baths, including the primary w/ a newly renovated ensuite offering a soaking tub & dual sinks. Completing this retreat-like property is a swimming pool w/ pool house & 2 composite decks for summertime gatherings!
19 Pilgrim Dr, Winchester, MA 01890 is a 5 bedroom, 4 bathroom, 3,150 sqft single-family home built in 1961. It last sold for the $1,775,000 asking price on Aug 15, 2025. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,803,400, with a rent estimate of $7,106/month.
Last check for updates: about 10 hours ago
Listed by Gorfinkle Group, (617) 820-8085
eXp Realty, (888) 854-7493
Dan Gorfinkle, (617) 820-8085
Bought with: Gregory Cumings, (617) 721-4433, Prevu Real Estate LLC, (646) 603-6868
Source: MLS PIN, MLS#73389326

Home Details for 19 Pilgrim Dr

Interior Features

Interior Details
Number of Rooms: 10Types of Rooms: Master Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Bedroom 5, Master Bathroom, Bathroom 1, Bathroom 2, Bathroom 3, Dining Room, Family Room, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 5Number of Bathrooms: 4Number of Bathrooms (full): 3Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 3150 Square Feet
Appliances & Utilities
Utilities: for Electric Dryer, Washer HookupAppliances: Water Heater, Range, Dishwasher, Disposal, Trash Compactor, Refrigerator, Washer, DryerDishwasherDisposalDryerLaundry: First Floor,Electric Dryer Hookup,Washer HookupRefrigeratorWasher
Heating & Cooling
Heating: Baseboard,OilHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Baseboard
Fireplace & Spa
Number of Fireplaces: 2Fireplace: Living RoomHas a FireplaceNo Spa
Windows, Doors, Floors & Walls
Window: Insulated Windows, ScreensDoor: French DoorsFlooring: Wood, Tile, Carpet
Levels, Entrance, & Accessibility
Floors: Wood, Tile, Carpet
Security
Security: Security System

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: DeckFencing: FencedOther Structures: CabanaExterior: Deck, Pool - Above Ground, Cabana, Rain Gutters, Professional Landscaping, Sprinkler System, Decorative Lighting, Screens, Fenced YardFoundation: Concrete PerimeterHas a Private PoolSprinkler System
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2Open Parking Spaces: 6No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 8Parking: Under,Heated Garage,Paved Drive,Off Street
Pool
Pool: Above GroundPool
Frontage
Road Frontage: PublicNot on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 3150

Property Information

Year Built
Year Built: 1961
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Raised Ranch
Building
Construction Materials: FrameNot Attached PropertyDoes Not Include Home Warranty
Property Information
Not Included in Sale: See Broker For ExclusionsParcel Number: M:026 B:0093 L:0, 901130

Price & Status

Price
List Price: $1,775,000
Status Change & Dates
Off Market Date: Fri Jun 20 2025

Active Status

MLS Status: Sold

Location

Direction & Address
City: Winchester
School Information
Elementary School: Vinson OwenJr High / Middle School: MccallHigh School: Winchester

Building

Building Area
Building Area: 3150 Square Feet

Community

Community Features: Public Transportation, Shopping, Pool, Tennis Court(s), Park, Walk/Jog Trails, Stable(s), Golf, Medical Facility, Laundromat, Bike Path, Conservation Area, Highway Access, House of Worship, Public School, T-StationNot Senior Community

HOA

No HOA

Lot Information

Lot Area: 0.47 acres

Offer

Contingencies: Financing

Miscellaneous

Mls Number: 73389326Above Grade Unfinished Area: 3150

Additional Information

Public TransportationShoppingPoolTennis Court(s)ParkWalk/Jog TrailsStable(s)GolfMedical FacilityLaundromatBike PathConservation AreaHighway AccessHouse of WorshipPublic SchoolT-Station

Price and Tax history

DateEventPrice
Aug 15, 2025
Source: MLS PIN #73389326
Sold
$1,775,000
Jun 17, 2025
Source: MLS PIN #73389326
Contingent
$1,775,000
Jun 11, 2025
Source: MLS PIN #73389326
Listed For Sale
$1,775,000
Jun 2, 2015
Source: N/A
Sold
$1,025,000
Feb 3, 2015
Source: Agent Provided
Pending
$999,999

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

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

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 19 Pilgrim Dr

  • What is 19 Pilgrim Dr estimated to be worth?
    Trulia's estimated value for 19 Pilgrim Dr in Winchester, MA is $1,803,400.
  • What is the price history for 19 Pilgrim Dr?
    19 Pilgrim Dr in Winchester, MA last sold for $1,775,000 in August 2025.
  • 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 19 Pilgrim Dr have air conditioning?
    Yes, 19 Pilgrim Dr in Winchester, MA has air conditioning.
  • Does 19 Pilgrim Dr have a pool?
    Yes, 19 Pilgrim Dr in Winchester, MA has a pool.

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Off Market Homes Near 19 Pilgrim Dr

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