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Properties

  • 29 Pilgrim Dr, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 10 Rooms Rooms,3 BathroomsBathrooms,Residential,For Sale,Pilgrim Dr,73491480
  • 29 Pilgrim Dr, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 10 Rooms Rooms,3 BathroomsBathrooms,Residential,For Sale,Pilgrim Dr,73491480
  • 29 Pilgrim Dr, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 10 Rooms Rooms,3 BathroomsBathrooms,Residential,For Sale,Pilgrim Dr,73491480
  • 29 Pilgrim Dr, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 10 Rooms Rooms,3 BathroomsBathrooms,Residential,For Sale,Pilgrim Dr,73491480
  • 29 Pilgrim Dr, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 10 Rooms Rooms,3 BathroomsBathrooms,Residential,For Sale,Pilgrim Dr,73491480
  • 29 Pilgrim Dr, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 10 Rooms Rooms,3 BathroomsBathrooms,Residential,For Sale,Pilgrim Dr,73491480
  • 29 Pilgrim Dr, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 10 Rooms Rooms,3 BathroomsBathrooms,Residential,For Sale,Pilgrim Dr,73491480
  • 29 Pilgrim Dr, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 10 Rooms Rooms,3 BathroomsBathrooms,Residential,For Sale,Pilgrim Dr,73491480
  • 29 Pilgrim Dr, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 10 Rooms Rooms,3 BathroomsBathrooms,Residential,For Sale,Pilgrim Dr,73491480
  • 29 Pilgrim Dr, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 10 Rooms Rooms,3 BathroomsBathrooms,Residential,For Sale,Pilgrim Dr,73491480
  • 29 Pilgrim Dr, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 10 Rooms Rooms,3 BathroomsBathrooms,Residential,For Sale,Pilgrim Dr,73491480
  • 29 Pilgrim Dr, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 10 Rooms Rooms,3 BathroomsBathrooms,Residential,For Sale,Pilgrim Dr,73491480
  • 29 Pilgrim Dr, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 10 Rooms Rooms,3 BathroomsBathrooms,Residential,For Sale,Pilgrim Dr,73491480
  • 29 Pilgrim Dr, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 10 Rooms Rooms,3 BathroomsBathrooms,Residential,For Sale,Pilgrim Dr,73491480
  • 29 Pilgrim Dr, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 10 Rooms Rooms,3 BathroomsBathrooms,Residential,For Sale,Pilgrim Dr,73491480
  • 29 Pilgrim Dr, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 10 Rooms Rooms,3 BathroomsBathrooms,Residential,For Sale,Pilgrim Dr,73491480
  • 29 Pilgrim Dr, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 10 Rooms Rooms,3 BathroomsBathrooms,Residential,For Sale,Pilgrim Dr,73491480
  • 29 Pilgrim Dr, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 10 Rooms Rooms,3 BathroomsBathrooms,Residential,For Sale,Pilgrim Dr,73491480
  • 29 Pilgrim Dr, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 10 Rooms Rooms,3 BathroomsBathrooms,Residential,For Sale,Pilgrim Dr,73491480
  • 29 Pilgrim Dr, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 10 Rooms Rooms,3 BathroomsBathrooms,Residential,For Sale,Pilgrim Dr,73491480
  • 29 Pilgrim Dr, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 10 Rooms Rooms,3 BathroomsBathrooms,Residential,For Sale,Pilgrim Dr,73491480
  • 29 Pilgrim Dr, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 10 Rooms Rooms,3 BathroomsBathrooms,Residential,For Sale,Pilgrim Dr,73491480
  • 29 Pilgrim Dr, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 10 Rooms Rooms,3 BathroomsBathrooms,Residential,For Sale,Pilgrim Dr,73491480
  • 29 Pilgrim Dr, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 10 Rooms Rooms,3 BathroomsBathrooms,Residential,For Sale,Pilgrim Dr,73491480
  • 29 Pilgrim Dr, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 10 Rooms Rooms,3 BathroomsBathrooms,Residential,For Sale,Pilgrim Dr,73491480
  • 29 Pilgrim Dr, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 10 Rooms Rooms,3 BathroomsBathrooms,Residential,For Sale,Pilgrim Dr,73491480
  • 29 Pilgrim Dr, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 10 Rooms Rooms,3 BathroomsBathrooms,Residential,For Sale,Pilgrim Dr,73491480
  • 29 Pilgrim Dr, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 10 Rooms Rooms,3 BathroomsBathrooms,Residential,For Sale,Pilgrim Dr,73491480
  • 29 Pilgrim Dr, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 10 Rooms Rooms,3 BathroomsBathrooms,Residential,For Sale,Pilgrim Dr,73491480
  • 29 Pilgrim Dr, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 10 Rooms Rooms,3 BathroomsBathrooms,Residential,For Sale,Pilgrim Dr,73491480
  • 29 Pilgrim Dr, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 10 Rooms Rooms,3 BathroomsBathrooms,Residential,For Sale,Pilgrim Dr,73491480
  • 29 Pilgrim Dr, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 10 Rooms Rooms,3 BathroomsBathrooms,Residential,For Sale,Pilgrim Dr,73491480
  • 29 Pilgrim Dr, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 10 Rooms Rooms,3 BathroomsBathrooms,Residential,For Sale,Pilgrim Dr,73491480
  • 29 Pilgrim Dr, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 10 Rooms Rooms,3 BathroomsBathrooms,Residential,For Sale,Pilgrim Dr,73491480
  • 29 Pilgrim Dr, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 10 Rooms Rooms,3 BathroomsBathrooms,Residential,For Sale,Pilgrim Dr,73491480
  • 29 Pilgrim Dr, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 10 Rooms Rooms,3 BathroomsBathrooms,Residential,For Sale,Pilgrim Dr,73491480
  • 29 Pilgrim Dr, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 10 Rooms Rooms,3 BathroomsBathrooms,Residential,For Sale,Pilgrim Dr,73491480
  • 29 Pilgrim Dr, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 10 Rooms Rooms,3 BathroomsBathrooms,Residential,For Sale,Pilgrim Dr,73491480
  • 29 Pilgrim Dr, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 10 Rooms Rooms,3 BathroomsBathrooms,Residential,For Sale,Pilgrim Dr,73491480
  • 29 Pilgrim Dr, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 10 Rooms Rooms,3 BathroomsBathrooms,Residential,For Sale,Pilgrim Dr,73491480
  • 29 Pilgrim Dr, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 10 Rooms Rooms,3 BathroomsBathrooms,Residential,For Sale,Pilgrim Dr,73491480
  • 29 Pilgrim Dr, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 10 Rooms Rooms,3 BathroomsBathrooms,Residential,For Sale,Pilgrim Dr,73491480
Property Description

Beautifully updated home offers generous living spaces and a seamless, open flow. Sun-filled living and dining areas feature hardwood floors, elegant detailing, and a fireplace that creates an inviting atmosphere. The kitchen is thoughtfully designed with quartz countertops, custom cabinetry, stainless appliances, wine chiller, and large island that opens to the dining area, which flows into the family room with direct access outdoors – ideal for yard access and entertaining. French doors between the kitchen, dining, and family room help to create a quieter, more private setting for the bedroom and formal living areas. The primary suite provides a private retreat with a full bath, while three additional bedrooms and full bath complete this level. A finished walk-out lower level adds versatility with a fireplace playroom, 5th bedroom, full bath, and laundry. Enjoy professionally landscaped grounds and inviting outdoor areas, complemented by an attached garage and ample parking.

Features
Heating System:
Oil, Baseboard, Fireplace(s)
Cooling System:
Central Air
Basement:
Full, Partially Finished, Garage Access, Sump Pump, Walk-out Access, Interior Entry, Concrete
Fireplace:
Living Room
Security:
Security System
Parking:
Attached, Under, Garage Door Opener, Off Street, Paved, Paved Drive, Oversized
Appliances:
Disposal, Range, Dishwasher, Microwave, Refrigerator, Washer, Dryer, Plumbed For Ice Maker, Oven, Water Heater, Wine Refrigerator, Tankless Water Heater
Construction:
Frame
Exterior Unit Features:
Screens, Professional Landscaping, Sprinkler System, Stone Wall, Rain Gutters
Flooring:
Tile, Wood, Engineered Hardwood, Carpet, Flooring - Stone/ceramic Tile, Flooring - Engineered Hardwood
Sewer:
Public Sewer
Style:
Raised Ranch
Water:
Public
Disclosure:
Some images have been digitally enhanced and virtually staged using AI to illustrate the property’s potential.
Electric Feature:
Circuit Breakers, 200+ Amp Service
Garage Parking:
2
Interior Features:
Closet/cabinets - Custom Built, Closet, Play Room, Lighting - Overhead, Center Hall
Lead Paint:
Unknown
Laundry Features:
Washer Hookup, First Floor, Flooring - Stone/ceramic Tile, Electric Dryer Hookup, Lighting - Overhead, Sink
Road Type:
Paved
Additional Information
Grade School:
Vinson Owen
High School:
Winchester Hs
Middle School:
Mccall
Market Time:
5
Parking Spaces:
6
Tax Year:
2026
Status:
Active
Price Per Sqft:
$535
Zoning:
RDA
Orig Price:
$1,749,000
Fireplaces:
2
Waterfront:
No
MlsStatus:
Active
Address Map
City:
Winchester
State:
MA
County:
Middlesex
Postal Code:
01890
Longitude:
W72° 50' 8.2''
Latitude:
N42° 26' 56.2''
  • Google Map

Residential

29 Pilgrim Dr, Winchester, Massachusetts

5 Bedrooms
3 Total Bathrooms
3,271 Sqft
$1,749,000
Listing ID #73491480
Basic Details
Property Type :
Residential
Listing Type :
For Sale
Price :
$1,749,000
Bedrooms :
5
Rooms :
10
Total Bathrooms :
3
Full Bathrooms :
3
Square Footage :
3,271 Sqft
Year Built :
1963
Lot Area :
0.47 Acre
Listing ID :
73491480
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Agent info
Robb Enterprises
  • Stephen E. Robb
  • View website
  • 617-212-0251
  • srobb@robbenterprises.com

Contact Agent

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.

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