$1,749,000
29 Pilgrim Dr
Winchester, MA, 01890
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
Property Details
Price:
$1,749,000
MLS #:
73491480
Status:
Pending
Beds:
5
Baths:
3
Type:
Single Family
Subtype:
Single Family Residence
Listed Date:
Mar 25, 2026
Finished Sq Ft:
3,271
Total Sq Ft:
3,271
Lot Size:
20,399 sqft / 0.47 acres (approx)
Year Built:
1963
Schools
Elementary School:
Vinson Owen
Middle School:
Mccall
High School:
Winchester Hs
Interior
Above Grade Finished Area
3271
Appliances
Water Heater, Tankless Water Heater, Range, Oven, Dishwasher, Disposal, Microwave, Refrigerator, Washer, Dryer, Wine Refrigerator, Plumbed For Ice Maker
Bathrooms
3 Full Bathrooms
Cooling
Central Air
Fireplaces Total
2
Flooring
Wood, Tile, Carpet, Engineered Hardwood, Flooring – Stone/Ceramic Tile, Flooring – Engineered Hardwood
Heating
Baseboard, Oil, Fireplace(s)
Interior Features
Closet/Cabinets – Custom Built, Lighting – Overhead, Closet, Play Room, Center Hall
Laundry Features
Flooring – Stone/Ceramic Tile, Electric Dryer Hookup, Washer Hookup, Lighting – Overhead, Sink, First Floor
Main Level Bathrooms
2
Main Level Bedrooms
3
Exterior
Accessibility Features
No
Architectural Style
Raised Ranch
Attached Garage YN
1
Community Features
Public Transportation, Shopping, Tennis Court(s), Park, Walk/Jog Trails, Golf, Medical Facility, Conservation Area, Highway Access, House of Worship, Public School
Construction Materials
Frame
Covered Spaces
2
Exterior Features
Rain Gutters, Professional Landscaping, Sprinkler System, Screens, Stone Wall
Garage Spaces
2
Lot Features
Gentle Sloping
Open Parking Spaces
4
Open Parking YN
1
Parking Features
Attached, Under, Garage Door Opener, Oversized, Paved Drive, Off Street, Paved
Parking Spots
6
Parking Total
6
Roof
Shingle
Security Features
Security System
Window Features
Screens
Financial
Tax Year
2026
Taxes
$17,564
Marie Andrews is an award-winning, licensed real estate broker with licenses in Massachusetts and Florida. She has been selling real estate in the greater Boston area for over 20 years. Over the past two decades, Marie has worked for Century 21 Advanced Realty, building a reputation as a multi-million dollar producer. She has developed an extensive network of investors, lenders, and attorneys. Marie has a wide knowledge base on property management, Massachusetts real estate law, and building…
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Map
Current real estate data for Single Family in Winchester as of May 04, 2026
71
Single Family Listed
48
Avg DOM
548
Avg $ / SqFt
$2,202,528
Avg List Price
Community
- Address29 Pilgrim Dr Winchester MA
- CityWinchester
- CountyMiddlesex
- Zip Code01890
Subdivisions in Winchester
- Brooks / Parkhurst / Town Forest
- Cox Road / High St Extension neighborhood
- Flats
- Flats neighborhood
- Lakeview/Wedgemere~ Near downtown & Wedgemere train station
- Macdonald field neighborhood
- Middlesex / downtown
- Near town/ Pine St neighborhood
- Old Village/ West Side
- Rangeley Historical Estate
- The Flats
- Vinson-Owen School District.
- West Side
- Winning Farm
Similar Listings Nearby
Property Summary
- 29 Pilgrim Dr Winchester MA is a Single Family for sale in Winchester, MA, 01890. It is listed for $1,749,000 and features 5 beds, 3 baths, and has approximately 3,271 square feet of living space, and was originally constructed in 1963. The current price per square foot is $535. The average price per square foot for Single Family listings in Winchester is $548. The average listing price for Single Family in Winchester is $2,202,528. To schedule a showing of MLS#73491480 at 29 Pilgrim Dr in Winchester, MA, contact your Pegasus Realty LLC agent at 781-858-3505.
Courtesy of Barrett Sotheby’s International Realty. The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information 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. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein.
29 Pilgrim Dr
Winchester, MA