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About this home
Prepare to be impressed by this extraordinary new construction residence on Canterbury Road, one of Winchester’s most sought-after and beloved neighborhoods. Beautifully designed with an exceptional sense of scale and luxurious appointments throughout, this remarkable home offers an unparalleled combination of elegance, comfort, and convenience, all just a short stroll from downtown Winchester, the commuter rail, shops, restaurants, and more. A spectacular first floor makes an immediate impression with soaring ceilings that carry throughout the home, creating an incredible sense of openness and grandeur. The beautifully proportioned formal living and dining rooms set the tone for the refined interiors. At the heart of the home, the showstopping chef’s kitchen features premium Sub-Zero and Wolf appliances, an oversized statement island, and an expansive eat-in area crowned by a skylight, opening seamlessly to a stunning family room with custom built-ins and a fireplace. A first-floor bedroom with en-suite bath offers wonderful flexibility as a private guest suite or sophisticated home office. Just beyond, an oversized deck extends the living space outdoors, overlooking a beautiful, private wooded backyard. The second level is equally impressive, with soaring ceilings continuing throughout and offering two generously sized bedrooms connected by a shared Jack-and-Jill bathroom, a spacious junior suite, and a spectacular primary retreat. The primary suite is a true escape, featuring a spa-inspired bath, two walk-in closets, and its own private deck overlooking the peaceful backyard. The finished lower level offers an entirely new dimension of living, complete with an additional bedroom and full bath, dedicated home theater, private gym, and expansive recreation room with endless possibilities for entertaining, relaxing, and recreation. An exceptional offering where sophisticated new construction, impressive living spaces, and an unbeatable walk-to-everything Winchester location come together to create a truly special place to make your own.
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Around this home
Schools
K - 12
Preschool & daycare
Ambrose Elementary School
Public K-5 • Assigned • 0.8mi
10/10
McCall Middle School
Public 6-8 • Assigned • 1.0mi
9/10
Winchester High School
Public 9-12 • Assigned • 1.4mi
10/10
Provided by GreatSchools
About Grove
Street
Grove Street, located between Main Street and Cambridge Street, is a residential and walkable Winchester neighborhood with leafy side streets and a commuter-rail rhythm. The neighborhood’s character concentrates around the Grove Street–Main Street junction, where café tables, small storefronts, and station-bound foot traffic set the daily pace. Community pillars include Book Ends, Winchester Community Music School, and the Jenks Center. Housing reads as classic New England, with well-kept Colonials and Victorians mixed with smaller cottages on tighter lots. A short walk leads to the Middlesex Fells Reservation trailheads for wooded loops and reservoir views. Sidewalks and pocket greens shape a calm, lived-in streetscape.
Provided by Walk Score and Local Logic
Market insights
25 Canterbury Rd · $3,499,000
DAYS ON MARKET
1 days
The average home goes pending in 23 days.
SALE-TO-LIST
100.8%
Most homes are selling 1% above list price.
LIST PRICE
$3,499,000
Median sale price in this area is $843,256. (76% lower than this home)
PRICE DROP
0 price drops
22% of homes in this area have had a price drop in the past month.
Property details
Interior
Exterior
Finance
Kitchen
Bathroom
Bedroom
Living
Dining
Interior features
Full finished basement with interior entry, sump pump, and radon remediation system
Exercise room, media room, playroom, and wet bar
Insulated doors and windows
Window screens
One fireplace in the family room
Open floor plan
Recessed lighting
Crown and decorative molding
Beamed ceilings
Custom built-in cabinets
Tray ceiling
Bedrooms
Five bedrooms: four on the second floor and one on the first floor
Bathrooms
Five full bathrooms and one half bathroom
Full bathrooms include tiled shower stalls; one also has a double vanity and a tiled tub
Kitchen
Kitchen island
Stone, granite, or solid-surface countertops
Dining area
Range, range hood, dishwasher, microwave, refrigerator, and wine refrigerator
Icemaker connection
Laundry & utility
Second-floor laundry with stone, granite, or solid-surface countertops and a sink
Washer hookup and electric dryer hookup
Flooring
Hardwood, tile, carpet, and wood laminate
Heating & cooling
Forced-air and electric heating
Dual central air conditioning
Thermostat
Exterior features
Wooded setting
Fenced yard
Professional landscaping and sprinkler system
Covered porch, composite deck, patio, and balcony
Rain gutters
Cistern water storage and water-recycling features
ET irrigation controller
Home design
Single-family residence
Parking
Attached garage with two spaces and garage door opener
Four open parking spaces
Side-facing garage with paved parking
Construction
Frame construction
Concrete perimeter and granite foundation
Shingle and rubber roof
Utilities
Public water and public sewer
Circuit breakers
HOA & community
Community amenities include public transportation, shopping, tennis courts, parks, walking and jogging trails, golf, medical facilities, bike paths, and conservation areas
Electricity and solar
View estimated energy costs and solar savings for this home
Don't miss your opportunity to own on Canterbury Road! This sun-drenched, 4-bedroom home with hardwood flooring offers an open and classic layout. Enjoy the spacious living room with built-ins, four, second floor bedrooms, and an expansive .37 acre lot. The versatile family room provides flexible space for a home office, playroom, or guest space! Imagine evenings on the covered porch or patio, taking in sunsets and seasonal Mystic Lake views. This well-preserved home awaits your personal touches. With an unfinished full basement and attic, there's plenty of room for growth, storage and potential. Winchester town center and West Medford village are each a pleasant, single mile away. Enjoy the restaurants, parks, shops and 3 convenient Commuter Rail stations for a quick 14-minute train ride to Boston. Welcome Home!
Year
Property tax
Land + Additions
Assessment*
2026
$14,186 (−0.8%)
$872,400 + $407,900
$1,280,300
2025
$14,302 (+5.8%)
$838,900 + $450,700
$1,289,600
2023
$13,516 (+4.3%)
$838,900 + $414,400
$1,253,300
2022
$12,964 (+4.3%)
$671,100 + $365,200
$1,036,300
2021
$12,435 (+3.6%)
$604,000 + $365,200
$969,200
2020
$12,008 (+9.9%)
$604,000 + $365,200
$969,200
2019
$10,924 (+6.8%)
$536,900 + $365,200
$902,100
2018
$10,227 (+11.2%)
$484,900 + $354,100
$839,000
2017
$9,195 (+9.9%)
$416,900 + $331,900
$748,800
2016
$8,366 (−2.0%)
$392,600 + $323,700
$716,300
2015
$8,533 (+7.7%)
$392,600 + $310,300
$702,900
2014
$7,926 (+0.6%)
$327,200 + $298,900
$626,100
2013
$7,882 (+1.8%)
$327,200 + $290,000
$617,200
2012
$7,746 (+3.7%)
$327,200 + $290,000
$617,200
2011
$7,468 (+6.2%)
$327,200 + $290,000
$617,200
2010
$7,034 (+2.1%)
$326,700 + $284,400
$611,100
2009
$6,887
$326,700 + $284,400
$611,100
Public record
Beds
3
Baths
1.5
Stories
2
Lot width
—
Lot depth
—
Lot size
0.37 Acres
Year renovated
—
Finished Sq. Ft.
2,349
Unfinished Sq. Ft.
—
Total Sq. Ft.
2,349
Year built
1948
Style
Single Family Residential
County
Middlesex County
APN
597832S
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Sep 16, 2026.
Climate risks
1/10 Flood Factor
Minimal risk of a flood reaching the building in the next 30 years
1/10 Fire Factor
Unlikely to be in a wildfire in next 30 years
5/10 Heat Factor
7 days above 98° expected this year, 15 days in 30 years
6/10 Wind Factor
58% chance of strong winds in next 30 years
3/10 Air Factor
3 unhealthy days expected this year, 3 days in 30 years
Provided by First Street
Historical weather
Winchester, MA • 01890
Average low and high temperatures (°F)
34
20
36
21
51
32
60
40
69
51
80
61
84
66
80
60
75
56
63
46
53
36
39
24
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Sun exposure
In this area, properties receive around 9.2 hours in
June and 4.4 hours in December, placing it below the
U.S. average for solar exposure.
9.2 hrs
4.4 hrs
JuneDecember
Provided by Shadowmap
Redfin Estimate for 25 Canterbury Rd
$3,506,542
$7,542 over list price of $3.50M
Nearby comparable homes
The Redfin Estimate uses 6 recent nearby sales, priced between $1.8M to $3.5M.