Beautifully renovated 19th century colonial unites the gracious elegance of yesterday with the modern amenities of today. One of Winchester's premier neighborhoods, Glen Road is a quaint one-way street close to downtown, schools and the train to Boston. The attached two car garage addition features a plumbed, unfinished second level with a separate entrance~ perfect for future in-law, home office or au pair space. The stunning white marble gourmet kitchen with over sized island enjoys a double wall oven, Wolf range, Sub Zero refrigerator and drawers, a large walk-in pantry with bar sink and a beverage refrigerator. The informal dining area, mudroom and office flow easily from the kitchen into a bright and open combination family/formal dining room with fireplace and sun room. The professionally landscaped yard with custom stonework and private patio add to the homes classic curb appeal.
Diamond in the rough - your opportunity to create the home of your dreams in a great Ambrose School neighborhood. Contractors and Buyers - this is a must see! Priced with improvements in mind, this is your chance to customize in a neighborhood where homes are selling for 1.3m and above. Enjoy the front to back living room with fireplace and consider adding heat to the 200 sf sunroom for year round use. The dining room features beautiful built-in buffet. NEW furnace (2015) and NEW hot water (2014). Second floor features large front to back master bedroom with 3/4 bath en suite; two additional bedrooms and a full bath. Two more rooms on third floor for bedrooms or office. Excellent location only a few blocks between Ambrose School and the Winchester Boat Club. Convenient to Commuter Rail from Wedgemere Station and Bus 350 to Alewife Station. Only 9 miles to Boston. Seller requests closing after June 27.
MLS PIN #30400188
Jun 1, 2000
Sold
$544,000
$220/sq ft
Apr 18, 2000
Listing Removed
—
Apr 7, 2000
Listed
$549,000
$222/sq ft
TASTEFULLY UPDATED COLONIAL FEATURING MANY PRESERVED DETAILS INCLUDING STAINED GLASS, LEADED GLASS CHINA CABINETS, BUTLERS PANTRY, HW FLOORS. FLEXIBLE 3RD FLOOR SPACE AWAITS YOUR NEED. SHORT WALK TO TOWN, TRAIN AND OPEN SPACE.
MLS PIN #50392480
Jun 1, 1998
Sold
$370,000
$149/sq ft
Apr 2, 1998
Listing Removed
—
Feb 20, 1998
Listed
$375,000
$151/sq ft
Public Records
Aug 10, 1984
Sold
$136,900
$55/sq ft
Year
Property tax
Land + Additions
Assessment*
2026
$18,375 (+3.1%)
$1,008,300 + $650,100
$1,658,400
2025
$17,828 (+2.7%)
$979,500 + $628,100
$1,607,600
2024
$17,363 (+0.9%)
$950,700 + $581,800
$1,532,500
2023
$17,206 (+4.4%)
$950,700 + $581,800
$1,532,500
2022
$16,483 (+5.6%)
$806,600 + $511,000
$1,317,600
2021
$15,612 (+5.8%)
$705,800 + $511,000
$1,216,800
2020
$14,760 (+12.9%)
$705,800 + $485,500
$1,191,300
2019
$13,070 (+11.8%)
$619,400 + $459,900
$1,079,300
2018
$11,693 (+2.0%)
$605,000 + $354,200
$959,200
2017
$11,463 (+10.0%)
$575,500 + $358,000
$933,500
2016
$10,422 (+3.8%)
$575,500 + $316,800
$892,300
2015
$10,040 (+3.1%)
$522,900 + $304,100
$827,000
2014
$9,734 (+0.2%)
$475,300 + $293,600
$768,900
2013
$9,712 (+4.2%)
$475,300 + $285,200
$760,500
2012
$9,318 (+3.7%)
$457,300 + $285,200
$742,500
2011
$8,984 (+3.9%)
$457,300 + $285,200
$742,500
2010
$8,644 (+2.1%)
$465,800 + $285,200
$751,000
2009
$8,464
$465,800 + $285,200
$751,000
Tax history for 50 Glen Rd
Year
Property tax
Land + Additions
Assessment*
2026
$18,375 (+3.1%)
$1,008,300 + $650,100
$1,658,400
2025
$17,828 (+2.7%)
$979,500 + $628,100
$1,607,600
2024
$17,363 (+0.9%)
$950,700 + $581,800
$1,532,500
2023
$17,206 (+4.4%)
$950,700 + $581,800
$1,532,500
2022
$16,483 (+5.6%)
$806,600 + $511,000
$1,317,600
2021
$15,612 (+5.8%)
$705,800 + $511,000
$1,216,800
2020
$14,760 (+12.9%)
$705,800 + $485,500
$1,191,300
2019
$13,070 (+11.8%)
$619,400 + $459,900
$1,079,300
2018
$11,693 (+2.0%)
$605,000 + $354,200
$959,200
2017
$11,463 (+10.0%)
$575,500 + $358,000
$933,500
2016
$10,422 (+3.8%)
$575,500 + $316,800
$892,300
2015
$10,040 (+3.1%)
$522,900 + $304,100
$827,000
2014
$9,734 (+0.2%)
$475,300 + $293,600
$768,900
2013
$9,712 (+4.2%)
$475,300 + $285,200
$760,500
2012
$9,318 (+3.7%)
$457,300 + $285,200
$742,500
2011
$8,984 (+3.9%)
$457,300 + $285,200
$742,500
2010
$8,644 (+2.1%)
$465,800 + $285,200
$751,000
2009
$8,464
$465,800 + $285,200
$751,000
*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.
Public record
Beds
5
Baths
3.5
Stories
2
Lot width
—
Lot depth
—
Lot size
8,712 Sq. Ft.
Year renovated
—
Sq. Ft.
2,897
Year built
1896
Style
Single Family Residential
County
Middlesex County
APN
1618436S
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Sep 16, 2026.
Property details
Parking
Parking Information
Has Garage
Has Open Parking
# of Garage Spaces: 2
# of Covered Spaces: 2
Parking Spaces: 4
AttachedGarageYN: Yes
Parking Features: Attached, Garage Door Opener, Storage, Garage Faces Side, Paved Drive, Off Street, Paved