29 Pilgrim DriveWinchester, MA 01890MLS Number 73491480

  • Price: $1,749,000
  • Est. Mortgage of $/month
  • 97 Days on Market
Print
$
$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Jun 25, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.
Under Agreement
29 Pilgrim Drive Winchester MA 0189029 Pilgrim Drive Winchester MA 0189029 Pilgrim Drive Winchester MA 0189029 Pilgrim Drive Winchester MA 0189029 Pilgrim Drive Winchester MA 0189029 Pilgrim Drive Winchester MA 0189029 Pilgrim Drive Winchester MA 0189029 Pilgrim Drive Winchester MA 0189029 Pilgrim Drive Winchester MA 0189029 Pilgrim Drive Winchester MA 0189029 Pilgrim Drive Winchester MA 0189029 Pilgrim Drive Winchester MA 0189029 Pilgrim Drive Winchester MA 0189029 Pilgrim Drive Winchester MA 0189029 Pilgrim Drive Winchester MA 0189029 Pilgrim Drive Winchester MA 0189029 Pilgrim Drive Winchester MA 0189029 Pilgrim Drive Winchester MA 0189029 Pilgrim Drive Winchester MA 0189029 Pilgrim Drive Winchester MA 0189029 Pilgrim Drive Winchester MA 0189029 Pilgrim Drive Winchester MA 0189029 Pilgrim Drive Winchester MA 0189029 Pilgrim Drive Winchester MA 0189029 Pilgrim Drive Winchester MA 0189029 Pilgrim Drive Winchester MA 0189029 Pilgrim Drive Winchester MA 0189029 Pilgrim Drive Winchester MA 0189029 Pilgrim Drive Winchester MA 0189029 Pilgrim Drive Winchester MA 0189029 Pilgrim Drive Winchester MA 0189029 Pilgrim Drive Winchester MA 0189029 Pilgrim Drive Winchester MA 0189029 Pilgrim Drive Winchester MA 0189029 Pilgrim Drive Winchester MA 0189029 Pilgrim Drive Winchester MA 0189029 Pilgrim Drive Winchester MA 0189029 Pilgrim Drive Winchester MA 0189029 Pilgrim Drive Winchester MA 0189029 Pilgrim Drive Winchester MA 0189029 Pilgrim Drive Winchester MA 0189029 Pilgrim Drive Winchester MA 01890
QR Code
  • 5Bedrooms
  • 0.47Acreage
  • 3Bathrooms
  • 1963Year Built

Driving Directions

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
Listed by Anne Spry of Barrett Sotheby's International Realty

Ask A Question

Do not fill in this field:

I agree to receive marketing and customer service calls and text messages from The Surrealtors. To opt out, you can reply 'stop' at any time or click the unsubscribe link in the emails. Consent is not a condition of purchase. Msg/data rates may apply. Msg frequency varies. Privacy Policy.

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

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

Basic Information

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

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

Other

  • Date Listed03/25/2026
  • Farm Land Area Units Square Feet
  • View Count5

Tax Information

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

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

Location

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

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

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

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

School Information

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

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

Exterior

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

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

Legal

  • ZoningRDA

Your Local Office

Real Brokerage

617-293-8070
MA
Our Agents

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. (MLSPIN) from third party sources, including sellers, lessors and public records, and were compiled by MLSPIN. The property listing data and information, and the Images, 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. MLSPIN and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

Hi there! How can we help you?

Contact us using the form below or give us a call.

Send Us A Message:

I agree to receive marketing and customer service calls and text messages from The Surrealtors. To opt out, you can reply 'stop' at any time or click the unsubscribe link in the emails. Consent is not a condition of purchase. Msg/data rates may apply. Msg frequency varies. Privacy Policy.

Do not fill in this field:

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Hi there! How can we help you?

Contact us using the form below or give us a call.

Send Us A Message:

Do not fill in this field:

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Hi there! How can we help you?

Contact us using the form below or give us a call.

Send Us A Message:

Do not fill in this field:

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Do not fill in this field:

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Do not fill in this field:

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Do not fill in this field:

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

$

Do not fill in this field:

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.