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

Single Family Residence

Type

16

Days on Market

Active Open House Listed Mar 25, 2026 • MLS# 73491480 Copied!

About this home

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

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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

12

Apr

Sunday, April 12

12:30 PM - 2:00 PM EDT

11

Apr

Saturday, April 11

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

3 schools

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

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

2 schools

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

Lexington Christian Academy

1.7 mi

Grades 06-12

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Property History

Property Timeline

🏠

Listed for Sale

Mar 25, 2026

$1,749,000

Original listing

Agent: Anne Spry Office: Barrett Sotheby's International Realty

Date	Event	Price	Change	$/sqft	Details
03/25/2026	🏠 Listed for Sale	$1,749,000	-	-	Original listing

Price & Status History

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

Market Statistics

Days on Market

16 days

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

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29 Pilgrim Dr, Winchester MA 01890

About this home

Property Overview

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Parking

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Interior Features

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Heating, Cooling & Utilities

Exterior & Lot

Parking & Garage

Special Features

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