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19 Glengarry RoadWinchester, MA 01890

For Sale

$2,099,000

Smart Buyer Rebate $10,495

A truly special opportunity to own a home in one of Winchester’s most desirable neighborhoods, just outside the vibrant town center! Welcome to 19 Glengarry Road~ this character-filled residence offers the perfect blend of charm, warmth & potential, making it ideal for buyers looking to personalize & create their dream home. Nestled in a top neighborhood near wedge pond, the home boasts classic details throughout, from original woodwork, beautiful fireplaces & hardwood floors to cozy, sun filled living spaces incl. a dreamy sun porch overlooking gorgeous back yard. 4 bedrooms & 2 baths on the 2nd floor, while the 3rd floor offers 2 additional beds. Full basement with flex living spaces including an additional bed or office & full bath. A large yard awaits with access/ frontage all the way to Grassmere Ave. With easy access to schools, shops, restaurants & the commuter rail, you’ll enjoy the best of Winchester living with unmatched convenience & one of the best neighborhoods around!

Listed by Kim Covino

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Compass

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781-249-3854

Listed by Kim Covino & Co. Team

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Compass

Last updated August 29, 2025

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Source: MLSPin #73418086

Listing Facts

  • TypeSingle-family
  • NeighborhoodThe Flats
  • Bedrooms6
  • Bathrooms4
  • Days on Prevu24
  • Taxes$20,054/year
  • Size3,521 sqft
  • Price per sqft$596

Amenities

  • Dishwasher
  • Private Outdoor Space
  • Washer/Dryer
  • Air Conditioning
  • Parking

Location

Mortgage Calculator

Listing History

08/14/2025
Listed by Compass
$2,099,000

Property Details for 19 Glengarry Road

Association

Amenities

  • Community Features: Public Transportation, Shopping, Tennis Court(s), Park, Walk/Jog Trails, Medical Facility, Bike Path, Highway Access, House Of Worship, Public School, T-Station

Exterior

Construction

  • Roof: Shingle
  • Year Built: 1897
  • Year Built Details: Approximate,Renovated Since
  • Architectural Style: Colonial
  • Construction Materials: Frame
  • Exterior Features: Porch - Enclosed, Porch - Screened

Features

  • Patio And Porch Features: Porch - Enclosed, Screened
  • View: Scenic View(s)

Measurements

  • Building Area Total: 3,521
  • Building Area Units: Square Feet
  • Lot Features: Gentle Sloping
  • Lot Size Acres: 0.25
  • Lot Size Area: 0
  • Lot Size Square Feet: 10,838
  • Lot Size Units: Acres

Financial

Taxes

  • Parcel Number: M:016 B:0230 L:0,899081
  • Tax Annual Amount: $20,054.00
  • Tax Assessed Value: $1,808,300.00
  • Tax Year: 2025

Interior

Features

  • Appliances: Range, Dishwasher, Disposal, Trash Compactor, Refrigerator, Freezer, Washer, Dryer
  • Fireplace Features: Dining Room, Family Room, Master Bedroom
  • Fireplace: Yes
  • Fireplaces Total: 3
  • Flooring: Hardwood, Flooring - Hardwood, Flooring - Stone/Ceramic Tile
  • Interior Features: Bathroom - With Shower Stall, Closet, Bathroom - Full, Bathroom, Bedroom, Foyer, Office

Measurements

  • Living Area: 3,521
  • Living Area Source: Public Record

Rooms

  • Basement: Full, Partially Finished
  • Bathrooms Full: 3
  • Bathrooms Half: 1
  • Bathrooms Total Integer: 4
  • Bedrooms Total: 6
  • Rooms Total: 13

Other

Location

  • Subdivision Name: Top Neighborhood Near Town Center

Parking

Parking

  • Attached Garage: Yes
  • Covered Spaces: 1
  • Garage Spaces: 1
  • Garage: Yes
  • Open Parking: Yes
  • Parking Features: Under, Paved Drive
  • Parking Total: 3

Schools

Elementary School

  • Elementary School: Ambrose

High School

  • High School: Whs

Middle or Junior School

  • Middle Or Junior School: Mccall

Utilities

Equipment

  • Cooling: Central Air
  • Has Cooling: Yes
  • Heating: Forced Air, Natural Gas
  • Has Heating: Yes
  • Laundry Features: In Basement
  • Sewer: Public Sewer
  • Utilities: For Gas Range
  • Water Source: Public

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. 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, leasing or renting 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, leasing or renting. 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, or as to the accuracy of any of the Images, set forth herein.

Full MLS Disclaimers

Rebate estimate is indicative only and based on listing price and estimated buyer's agent commission paid by owner, if applicable. Final rebates are subject to Terms of Use and may vary due to final negotiated transaction terms.