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About this home
Magnificent newer sun-filled Colonial ideally situated in a premier West Side cul-de-sac, offering over 8,000 sq ft of beautifully finished living space across four levels-A great price at only $368psf! !Designed for grand-scale entertaining and multi-generational living, this exceptional home features 7 bedrooms, 7.5 baths, four fireplaces and a 3-car direct-entry garage, all complemented by custom built-ins, fine cabinetry and beautiful millwork throughout. The newly renovated chef’s kitchen showcases quartz countertops, an oversized center island, two dishwashers and a butler’s pantry with wine fridge and ice maker, flowing seamlessly into the elegant dining room, living room and fireplaced family room overlooking the meticulously maintained grounds. A dedicated first-floor wing offers incredible flexibility for extended family, au pair or guests, while a private office with custom wet bar and additional spaces can easily accommodate two executive home offices. Upstairs, the grand primary suite is joined by four additional bedroom suites, each offering a private bath, sitting area and generous closet space. The third floor provides a completely private guest or teen suite with a full bath and two closets.The finished lower-level offers media, game and gym areas with a full bath and direct access to the inviting heated pool and lush landscaped grounds. Unmatched in scale and versatility with resort-like amenities, exceptional craftsmanship and a coveted West Side location, this remarkable home offers luxury living at its finest.
West Side, located between the Aberjona River and the Middlesex Fells Reservation, is a residential and commuter-friendly Winchester neighborhood with leafy side streets and trail-forward green space. The neighborhood’s character concentrates around the Winchester Center area at Main Street and Church Street, where independent cafes, small shops, and the commuter rhythm of the station set the pace. Community pillars include the Winchester Community Music School, the Winchester Unitarian Society’s historic campus, and the Jenks Center. Housing reads as classic New England—Colonial Revivals, Victorians, and well-kept mid-century homes—on walkable blocks with stone walls and mature trees. The Fells’ trailheads and reservoirs shape daily routines, while the river corridor adds a quieter, tucked-away geography. A short ride to the station keeps Boston-bound schedules in view without turning the streetscape into a thoroughfare.
Provided by Walk Score and Local Logic
Market insights
37 Mayflower Rd · $3,149,000
DAYS ON MARKET
1 days
The average home goes pending in 22 days.
SALE-TO-LIST
101.2%
Most homes are selling 1% above list price.
LIST PRICE
$3,149,000
Median sale price in this area is $919,982. (71% lower than this home)
PRICE DROP
0 price drops
18% of homes in this area have had a price drop in the past month.
Property details
Interior
Exterior
Finance
Kitchen
Bathroom
Bedroom
Living
Interior features
Wet bar
Walk-in closets
Custom built closets/cabinets
Ceiling fans
Recessed and overhead lighting
Sconce lighting
Office
Foyer
Game room
Exercise room
Wired for sound
Total of 13 rooms
Insulated and storm windows with screens
Tile and hardwood flooring
Stone/ceramic tile flooring
Full finished walk-out basement with interior entry
Bedrooms
Primary bedroom on second floor with double vanity, dressing room, recessed lighting, sconce lighting and hardwood floors
Additional bedrooms on second floor with ceiling fans, walk-in closets and hardwood (some with stone/ceramic tile accents)
Bathrooms
Seven full bathrooms
One half bathroom
Master bath present
Kitchen
Upgraded countertops
Kitchen island
Breakfast bar / nook
Country-style kitchen
Exterior access
Recessed, pendant and overhead lighting
Hardwood flooring
Laundry & utility
Laundry on second floor (approx. 17x8) with hardwood flooring
Gas water heater
Flooring
Hardwood throughout main living areas
Tile
Stone/ceramic tile in bathrooms and select rooms
Heating & cooling
Forced air heating (natural gas)
Fireplaces contribute to heat
Central air conditioning
Exterior features
Inground private pool
Deck and patio
Professional landscaping with garden
Sprinkler system
Decorative exterior lighting
Fenced/enclosed yard
Cul-de-sac lot
Public, paved road frontage on a dead-end street
Home design
Single family residence
Approximately renovated since original construction
Beige exterior
Shingle roof
Concrete perimeter foundation
Parking
Attached oversized garage with 3 garage spaces and garage door opener
Three covered spaces
Nine open/off-street paved parking spaces (12 total parking spaces)
Paved driveway
Security
Security system
Construction
Frame construction
Concrete perimeter foundation
Shingle roof
Utilities
Public water
Public sewer
Gas available for range
HOA & community
Community amenities nearby: shopping, pool, tennis courts, parks, walk/jog trails, golf and sidewalks
Financial info
Heat zones: 6
Other
Above-grade finished living area approximately 7,226
Below-grade finished area approximately 1,314
Total building area approximately 8,540
Electricity and solar
View estimated energy costs and solar savings for this home
Magnificent new sun filled center entrance colonial home with 3 car garage. Attention to the finest details - gleaming hard wood floors, beautiful built-ins & custom cabinetry, classic tile & granite, 3 gas fireplaces, decorative crown molding. This expansive home has a stunning state-of-the art kitchen with pantry, each bedroom offers baths & walk in closets. Separate office or bedroom suite on 1st floor. 3rd floor suite with bath & 2 walk in closets. Situated on a corner lot with IG pool.
Public Records
Nov 24, 2008
Sold
$700,000
$82/sq ft
MLS PIN #30422731
Sep 29, 2000
Sold
$625,000
$73/sq ft
Jun 28, 2000
Listing Removed
—
Jun 22, 2000
Listed
$615,000
$72/sq ft
METICULOUSLY MAINTAINED HOME- E ON GORGEOUS, MANICURED CORNER LOT. QUALITY BLT. RANCH WITH GENEROUSLY SIZED ROOMS, HTD. GAR., CENTRAL A/C, SECURITY, INTERCOM, SCREENED PORCH. FABULOUS FAMILY ROOM. LOW MAINT.
Year
Property tax
Land + Additions
Assessment*
2025
$29,834 (+6.3%)
$1,040,100 + $1,650,100
$2,690,200
2023
$28,071 (+1.3%)
$1,000,100 + $1,529,900
$2,530,000
2022
$27,708 (+2.1%)
$760,100 + $1,454,800
$2,214,900
2021
$27,134 (+3.5%)
$660,100 + $1,454,800
$2,114,900
2020
$26,204 (+2.3%)
$660,100 + $1,454,800
$2,114,900
2019
$25,611 (+2.3%)
$660,100 + $1,454,800
$2,114,900
2018
$25,025 (+5.1%)
$638,100 + $1,414,800
$2,052,900
2017
$23,820 (+7.4%)
$578,100 + $1,361,600
$1,939,700
2016
$22,180 (+1.7%)
$578,100 + $1,320,900
$1,899,000
2015
$21,816 (−1.0%)
$525,100 + $1,271,900
$1,797,000
2014
$22,045 (+1.1%)
$485,100 + $1,256,200
$1,741,300
2013
$21,811 (+0.4%)
$485,100 + $1,222,900
$1,708,000
2012
$21,723 (−10.4%)
$485,100 + $1,245,800
$1,730,900
2011
$24,235 (+88.3%)
$485,100 + $1,517,800
$2,002,900
2010
$12,872 (+38.0%)
$451,300 + $667,000
$1,118,300
2009
$9,330
$451,300 + $376,600
$827,900
Public record
Beds
7
Baths
7.5
Stories
2
Lot width
—
Lot depth
—
Lot size
0.46 Acres
Year renovated
—
Finished Sq. Ft.
7,209
Unfinished Sq. Ft.
—
Total Sq. Ft.
7,209
Year built
2009
Style
Single Family Residential
County
Middlesex County
APN
3036595S
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Jul 29, 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
50% chance of strong winds in next 30 years
3/10 Air Factor
2 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
85
67
80
60
75
57
64
46
53
36
39
24
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Sun exposure
96/ 100
Exceptional sunlight
Sunscore
This home ranks in the top 1% for direct sun exposure in the zip code. There appears to be minimal shading by surrounding buildings, terrain, and vegetation.
10.7 hrs
5.9 hrs
JuneDecember
Provided by Shadowmap
Redfin Estimate for 37 Mayflower Rd
$3,188,545
$40K over list price of $3.15M
Nearby comparable homes
The Redfin Estimate uses 6 recent nearby sales, priced between $2.0M to $3.5M.