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29 Pilgrim Dr, Winchester MA 01890

Winchester, MA 01890
$1,749,000
Est. $10,508/month
5
Beds
3
Baths
3,271
Sq Ft
$535
Price/Sq Ft
0.47
Acres
1963
Year Built
2 hours 17 minutes
Time on Market
Active Open House Listed Mar 25, 2026 • MLS# 73491480 Copied!

About this home

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.

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Property Overview

Property Type
Single Family Residence
Listing Type
For Sale
Year Built
1963
Bedrooms
5
Full Bathrooms
3
Living Area
3,271 sq ft
Total Rooms
10
Main Level Bedrooms
3

Open House Schedule

27
Mar
Friday, March 27
5:00 PM - 6:30 PM EDT
27
Mar
Friday, March 27
12:00 PM - 1:00 PM EDT
28
Mar
Saturday, March 28
1:00 PM - 2:30 PM EDT
29
Mar
Sunday, March 29
1:00 PM - 2:30 PM EDT

Facts & Features

2 Car Garage
Central AC

Home Facts

Type Residential
Style Single Family Residence
Year Built 1963
Living Area 3,271 sq ft
Lot Size 0.47 acres
Bedrooms 5
Full Baths 3
Total Rooms 10

Interior

Heating Baseboard, Oil, Fireplace(s)
Cooling Central Air
Flooring Wood, Tile, Carpet, Engineered Hardwood, Flooring - Stone/ceramic Tile, Flooring - Engineered Hardwood
Appliances Water Heater, Tankless Water Heater, Range, Oven, Dishwasher, Disposal, Microwave, Refrigerator, Washer, Dryer, Wine Refrigerator, Plumbed For Ice Maker
Fireplace Living Room
Fireplaces 2
Basement Full, Partially Finished, Walk-out Access, Interior Entry, Garage Access, Sump Pump, Concrete
Laundry Flooring - Stone/ceramic Tile, Electric Dryer Hookup, Washer Hookup, Lighting - Overhead, Sink, First Floor
Features Closet/cabinets - Custom Built, Lighting - Overhead, Closet, Play Room, Center Hall

Exterior

Construction Frame
Architecture Raised Ranch
Roof Shingle
Features Rain Gutters, Professional Landscaping, Sprinkler System, Screens, Stone Wall
Pool None
Spa None
Fencing None
Patio/Porch None

Parking

Garage Spaces 2
Has Garage Yes
Features Attached, Under, Garage Door Opener, Oversized, Paved Drive, Off Street, Paved
Total Spaces 6

Utilities

Electric Circuit Breakers, 200+ Amp Service
Water Public
Sewer Public Sewer
Gas None
Other For Electric Range, For Electric Oven, For Electric Dryer, Washer Hookup, Icemaker Connection

Financial

Annual Tax $17,564
Assessed Value $1,585,200

Interior Features

Flooring: Wood, Tile, Carpet, Engineered Hardwood, Flooring - Stone/Ceramic Tile, Flooring - Engineered Hardwood
Appliances: Water Heater, Tankless Water Heater, Range, Oven, Dishwasher, Disposal, Microwave, Refrigerator, Washer, Dryer, Wine Refrigerator, Plumbed For Ice Maker
Interior Features: Closet/Cabinets - Custom Built, Lighting - Overhead, Closet, Play Room, Center Hall
Windows: Screens
Basement: Full, Partially Finished, Walk-Out Access, Interior Entry, Garage Access, Sump Pump, Concrete
Laundry: Flooring - Stone/Ceramic Tile, Electric Dryer Hookup, Washer Hookup, Lighting - Overhead, Sink, First Floor
Security: Security System

Construction & Materials

Style: Raised Ranch
Year Built: 1963
Structure Type:
Exterior Materials: Frame
Roof: Shingle
Foundation: Concrete Perimeter

Heating, Cooling & Utilities

Heating: Baseboard, Oil, Fireplace(s)
Heating Zones: 3
Cooling: Central Air
Cooling Zones: 1
Hot Water:
Water Source: Public
Sewer: Public Sewer
Energy Features:

Exterior & Lot

Exterior Features: Rain Gutters, Professional Landscaping, Sprinkler System, Screens, Stone Wall
Patio & Porch:
Fencing:
Other Structures:
Lot Features: Gentle Sloping
Road Surface: Paved

Parking & Garage

Garage Spaces: 2
Garage Type: Attached
Total Parking Spaces: 6
Parking Features: Attached, Under, Garage Door Opener, Oversized, Paved Drive, Off Street, Paved

Special Features

Fireplaces: 2
Fireplace Type: Living Room
Community Amenities: Public Transportation, Shopping, Tennis Court(s), Park, Walk/Jog Trails, Golf, Medical Facility, Conservation Area, Highway Access, House of Worship, Public School

Location

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Neighborhood

29 Pilgrim Dr, Winchester MA 01890

Winchester, MA 01890

Walkability

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Nearby Schools

School District
Winchester School District local
A+
School Safety 2024-25
0.1% Very Low (Safest)
0.1% Suspensions 0.1% In-School
5.4% below state avg
E

Elementary Schools

10 schools
Acera School
2.0 mi
Grades K-08
The Wilder School
2.2 mi
Grades K-12
A+
Ambrose Elementary School
0.5 mi | #11 of 824 | Score: 66.1
Improved 36 spots from last year
+7.9 above state avg
398 students Moderate
Rising School Strong Attendance
Grades K-05
A+
Vinson-Owen Elementary School
0.5 mi | #40 of 824 | Score: 63.2
Improved 112 spots from last year
+5 above state avg
441 students Diverse
Rising School Strong Attendance
Grades PK-05
A
Lynch Elementary School
1.1 mi | #113 of 824 | Score: 58.6
Dropped 31 spots from last year
+0.4 above state avg
426 students Diverse
Grades PK-05
Creative Corner School Inc
1.4 mi
Grades PK-K
A+
Lincoln Elementary School
1.5 mi | #74 of 824 | Score: 60.7
Dropped 29 spots from last year
+2.5 above state avg
334 students Moderate
Strong Attendance
Grades K-05
St. Mary Elementary School
1.7 mi
Grades PK-05
Children's Own School
1.7 mi
Grades PK-K
A+
Muraco Elementary School
2.0 mi | #62 of 824 | Score: 61.6
Improved 62 spots from last year
+3.4 above state avg
352 students Diverse
Rising School Strong Attendance
Grades K-05
M

Middle Schools

1 school
A+
McCall Middle School
1.5 mi | #16 of 352 | Score: 62.4
Dropped 3 spots from last year
+4.2 above state avg
1,036 students Diverse
Strong Attendance
Grades 06-08
H

High Schools

1 school
A+
Winchester High School
1.6 mi | #17 of 346 | Score: 73.6
Improved 18 spots from last year
+15.4 above state avg
1,404 students Diverse
20 sports • 2,818 athletes
Strong AP Program High Graduation Rate College Ready Curriculum Strong Athletics
Grades 09-12
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Including down payment
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Down: $0
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Monthly Payment Breakdown

Principal & Interest $0
Property Tax $1,464
Homeowners Insurance $200
PMI (if <20% down) $0

Loan Summary

Total of 360 payments $0
Total principal paid $0
Total interest paid $0

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Payment Over Time

Interest
Principal
Year 1
95% Interest
Year 15
50/50
Year 30
95% Principal
* Estimates only. Actual payments may vary. Consult with a lender for accurate figures.

Property History

Property Timeline

🏠
Listed for Sale
Mar 25, 2026
$1,749,000
Original listing
Agent: Anne Spry Office: Barrett Sotheby's International Realty

Price & Status History

Date Event Price Change
Mar 25, 2026 New Listing Added $1,749,000

Market Statistics

Time on Market
2 hours 17 minutes
Price per Sq Ft
$535

Tax History

Year Taxes Assessment
2026 $17,564 $1,585,200

Financial Details

Annual Property Tax
$17,564
Tax Year 2026
Assessed Value
$1,585,200

Listing Information

Listing Agent Anne Spry
Listing Office Barrett Sotheby's International Realty
Agent MLS ID B9500374
Office MLS ID AN6380
Listing information is deemed reliable but not guaranteed. Data provided by MLS Property Information Network, Inc. All information should be independently verified.

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