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$1,749,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 5 Beds
  • 3 Full Baths
  • 3,271 Sq. Ft.
  • 0.47 Acres
  • 2 Car Garage
  • Updated 2 hours ago

Next open house:

Open House: 5:00 PM - 6:30 PM

Friday 3/27 5:00 PM - 6:30 PM

29 Pilgrim Dr,Winchester, MA 01890

29 Pilgrim DrWinchesterMA01890

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Join us at 29 Pilgrim Dr on:

  • Open House: 1:00 PM - 2:30 PM

    Saturday 3/28 1:00 PM - 2:30 PM

    29 Pilgrim Dr,Winchester, MA 01890
    29 Pilgrim DrWinchesterMA01890
  • Open House: 1:00 PM - 2:30 PM

    Sunday 3/29 1:00 PM - 2:30 PM

    29 Pilgrim Dr,Winchester, MA 01890
    29 Pilgrim DrWinchesterMA01890
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See This Home
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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.

Full Property Details for 29 Pilgrim Dr

General

  • Price: $1,749,000
  • Taxes: $17,564 (2026)
  • Status: Active
  • Type: Single Family
  • MLS ID: 73491480
  • Updated: Today (3/25/2026)
  • Added to Site: Today

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 3
  • Bathroom 1: 7.75 x 4.67, Main, Second
  • Bathroom 2: 10.25 x 6.92, Main, Second
  • Bathroom 3: 8.58 x 6.00, First

Bedrooms

  • Total Bedrooms: 5
  • Primary Bedroom: 15.00 x 13.00, Main, Second
  • Bedroom 2: 16.67 x 13.08, Main, Second
  • Bedroom 3: 13.25 x 13.08, Main, Second
  • Bedroom 4: 11.42 x 11.42, Second

Other Rooms

  • Living Room: 32.17 x 15.17, Main, Second
  • Family Room: 15.67 x 9.67, Main, Second
  • Kitchen: 16.50 x 13.42, Main, Second
  • Dining Room: 13.42 x 13.00, Main, Second

Parking

  • Garage: Yes
  • Garage Spaces: 2
  • Parking Features: Attached, Under, Garage Door Opener, Oversized, Paved Drive, Off Street, Paved

Location

  • County: Middlesex

Structural Information

  • Architectural Style: Raised Ranch
  • Basement: Yes
  • Square Feet: 3,271
  • Year Built: 1963

Lot Features

  • Lot Size (Acres): 0.47

Financial Considerations

  • Tax Amount: $17,564
  • Tax Year: 2026

Disclosures and Reports

  • Disclosures/Rstr.: A/C covers top level.
  • Property ID: M:021 B:0362 L:0, 900485

Listed by Barrett Sotheby's International Realty, Anne Spry

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Listing agent

— 29 Pilgrim Dr —

  • Anne Spry

    Barrett Sotheby's International Realty

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 29 Pilgrim Dr

School District:Winchester School District, Winchester, MA
NameGradesDistance
Vinson-Owen Elementary School
75 Johnson Road, Winchester, MA 01890
K-50.5 mi
Mccall Middle School
458 Main Street, Winchester, MA 01890
6-81.5 mi
Winchester High School
80 Skillings Road, Winchester, MA 01890
9-121.6 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 29 Pilgrim Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
3/25/2026
Listed
$1,749,000
342.78%
MLS
7/20/1994
Sold
$395,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 29 Pilgrim Dr

Year
Property Taxes
Change
Tax Assessment
Change
2025
$16,954
3%
$1,528,800
6%
2024
$16,414
15%
$1,448,700
20%
2023
$14,263
—
$1,208,700
6%
2022
$14,251
7%
$1,139,200
10%
2021
$13,333
4%
$1,039,200
—
2020
$12,876
6%
$1,039,200
4%
2019
$12,100
5%
$999,200
5%
2018
$11,555
3%
$947,900
3%
2017
$11,252
8%
$916,300
3%
2016
$10,409
7%
$891,200
12%
2015
$9,683
—
$797,600
4%
2014
$9,667
—
$763,600
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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NMLS#: 1598647

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Listed by Barrett Sotheby's International Realty, Anne Spry

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Listed by Erica Carson

29 Pilgrim Dr, Winchester, MA 01890 (MLS# 73491480) is a Single Family property with 5 bedrooms and 3 full bathrooms. 29 Pilgrim Dr is currently listed for $1,749,000 and was received on March 25, 2026. Want to learn more about 29 Pilgrim Dr? Do you have questions about finding other Single Family real estate for sale in Winchester? You can browse all Winchester real estate or contact a Coldwell Banker agent to request more information.

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