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

More Info

Basic Information

  • Bedrooms5
  • Mls StatusUnder Agreement
  • Bathroom3
  • Contingency Pending P&S
  • Lot Features Gentle Sloping
  • Parcel Number M:021 B:0362 L:0,900485
  • Road Frontage DescriptionPaved

Tax Information

  • Tax Assessed Value $1,585,200
  • Tax Year 2026
  • Taxes$17,564

School Information

  • High School Winchester Hs
  • Elementary SchoolVinson Owen
  • Junior HighMccall

Parking

  • Parking Spaces6
  • Covered Spaces 2
  • Garage YN Yes
  • Open Parking YN Yes
  • Parking Features
    • Attached
    • Garage Door Opener
    • Off Street
    • Oversized
    • Paved
    • Paved Drive
    • Under

Rooms

  • Bathroom 1 Main, Second,7.75 x 4.666666666
  • Bathroom 2 Main, Second,10.25 x 6.916666666
  • Bathroom 3 First,8.583333333 x 6
  • Bathrooms Total Decimal 3
  • Bedroom 2 Main, Second,16.666666666 x 13.083333333
  • Bedroom 3 Main, Second,13.25 x 13.083333333
  • Bedroom 4 Second,11.416666666 x 11.416666666
  • Bedroom 5 First,13 x 10.5
  • Dining Room Main, Second,13.416666666 x 13
  • Family Room Main, Second,15.666666666 x 9.666666666
  • Full Bath3
  • Kitchen Main, Second,16.5 x 13.416666666
  • Living Room Main, Second,32.166666666 x 15.166666666
  • Main Level Bathrooms 2
  • Main Level Bedrooms 3
  • Master Bedroom Main, Second,15

Basic Information

  • List Price$1,749,000
  • MLS Number73491480
  • Modification Date04/27/2026
  • Property SubTypeSingle Family Residence
  • PurchaseContractDate04/14/2026
  • Virtual TourView Tour

Location

  • Address29 Pilgrim Drive
  • Building Number29
  • CountyMiddlesex
  • StateMA
  • StreetPilgrim Drive
  • TownWinchester
  • Zip01890

Building

  • Attached Garage YN Yes
  • Basement
    • Concrete
    • Full
    • Garage Access
    • Interior Entry
    • Partially Finished
    • Sump Pump
    • Walk-Out Access
  • Building Area Units Square Feet
  • Construction Materials Frame
  • FireplaceYes
  • Fireplace Features Living Room
  • Fireplaces Total 2
  • FoundationConcrete Perimeter
  • Garage Spaces2
  • Property StyleRaised Ranch
  • Rooms10
  • Utilities For Electric Range, For Electric Oven, For Electric Dryer, Washer Hookup, Icemaker Connection
  • Window Features Screens
  • Year Built1963
  • Year Built Details Approximate
  • Year Built Source Public Records

Property

  • Acreage0.47

Interior

  • Flooring
    • Carpet
    • Engineered Hardwood
    • Flooring - Engineered Hardwood
    • Flooring - Stone/Ceramic Tile
    • Tile
    • Wood
  • Interior Features Closet/Cabinets - Custom Built, Lighting - Overhead, Closet, Play Room, Center Hall

Exterior

  • Exterior Features Rain Gutters, Professional Landscaping, Sprinkler System, Screens, Stone Wall
  • RoofShingle

Utilities

  • Cooling Central Air
  • Cooling YN Yes
  • Electric Circuit Breakers,200+ Amp Service
  • Heat SystemYes
  • Heating Baseboard, Oil, Fireplace(s)
  • Sewer Public Sewer
  • Water Source Public

Property Information

  • Square Feet3,271
  • Building Area Source Public Records
  • Living Area 3,271
  • Lot Size Square Feet 20,399
  • Lot Size Units Acres
  • Road Responsibility Public Maintained Road

Amenities

  • Amenities
    • Conservation Area
    • Golf
    • Highway Access
    • House of Worship
    • Medical Facility
    • Park
    • Public School
    • Public Transportation
    • Shopping
    • Tennis Court(s)
    • Walk/Jog Trails
  • Appliances IncludedWater Heater, Tankless Water Heater, Range, Oven, Dishwasher, Disposal, Microwave, Refrigerator, Washer, Dryer, Wine Refrigerator, Plumbed For Ice Maker
  • Security Features Security System

Other

  • Date Listed03/25/2026
  • Farm Land Area Units Square Feet

Map Location

Driving Directions

Listed by Anne Spry of Barrett Sotheby's International Realty

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