
37 Mayflower Road Winchester — Photo 1 of 42
$3,149,000
37 Mayflower Road, Winchester, MA 01890
Winchester, MA 01890
Beds
7
Baths
7.5
SqFt
8,540
Style
Single Family
Built
2009
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.
Market Value Analysis
* Analysis is based on 24 actively listed and recently sold comparable properties strictly within Winchester, MA.
Property Details
Financials
Parking
Interior Specifications
Climate & Utilities
Building & Exterior
Property & Lot
Amenities & Appliances
Gas Water Heater • Oven • Dishwasher • Disposal • Microwave • Range • Refrigerator • Freezer • Washer • Dryer • Wine Refrigerator
Neighborhood
Shopping • Pool • Tennis Court(s) • Park • Walk/Jog Trails • Golf
Geography
Floorplan Breakdown
Structural Layout
Living Room
Lvl First20 x 16
Flooring - Hardwood, Lighting - Sconce
Dining Room
Lvl First20 x 15
Flooring - Hardwood, Lighting - Sconce, Lighting - Pendant
Kitchen
Lvl First22 x 13
Flooring - Hardwood, Countertops - Upgraded, Kitchen Island, Breakfast Bar / Nook, Country Kitchen, Exterior Access, Recessed Lighting, Lighting - Pendant, Lighting - Overhead
Office
Lvl First16 x 14
Fireplace, Flooring - Hardwood, Wet bar
Family Room
Lvl First21 x 18
Ceiling Fan(s), Flooring - Hardwood, Recessed Lighting, Lighting - Sconce
Master Bedroom
Lvl Second30 x 20
Bathroom - Full, Ceiling Fan(s), Walk-In Closet(s), Closet/Cabinets - Custom Built, Flooring - Hardwood, Double Vanity, Dressing Room, Recessed Lighting, Lighting - Sconce, Closet - Double
Bedroom 2
Lvl Second17 x 16
Bedroom 3
Lvl Second22 x 17
Bathroom - Full, Ceiling Fan(s), Walk-In Closet(s), Closet/Cabinets - Custom Built, Flooring - Hardwood, Flooring - Stone/Ceramic Tile
Bedroom 4
Lvl Second18 x 17
Bathroom - Full, Ceiling Fan(s), Walk-In Closet(s), Closet/Cabinets - Custom Built, Flooring - Hardwood, Flooring - Stone/Ceramic Tile, Recessed Lighting
Bedroom 5
Lvl Second15 x 15
Bathroom - Full, Ceiling Fan(s), Walk-In Closet(s), Flooring - Hardwood, Recessed Lighting
Bathroom 1
Lvl First9 x 6
Walk-In Closet(s), Closet/Cabinets - Custom Built, Flooring - Stone/Ceramic Tile
Bathroom 2
Lvl Second15 x 13
Bathroom - Full, Flooring - Stone/Ceramic Tile
Bathroom 3
Lvl Second10 x 9
Bathroom - Full, Flooring - Stone/Ceramic Tile
Property History
$3,149,000
Sep 8, 2026
MLS® 73573670
$3,179,000
Sep 3, 2026
MLS® 73502853
$3,179,000
Apr 16, 2026
MLS® 73502853
$3,537,000
Apr 14, 2026
MLS® 73475646
$3,537,000
Feb 9, 2026
MLS® 73475646
$1,899,999
May 2, 2011
MLS® 71012550
$1,899,999
Dec 23, 2009
MLS® 71012550
Population
23,406
U.S. Census Bureau, ACS 2024 5-Year Estimates (B01003)
Median Household Income
$230K
U.S. Census Bureau, ACS 2024 5-Year Estimates (B19013)
Renter-Occupied Homes
18.3%
U.S. Census Bureau, ACS 2024 5-Year Estimates (B25003)
New Construction Permits — Middlesex County
2,667 housing units permitted in the last 12 months (-2% vs the prior 12 months) — 1,709 in 5+ unit buildings
U.S. Census Bureau, Building Permits Survey (through Jun '26)
ADU Potential
Massachusetts allows one accessory dwelling unit by right in single-family zoning districts statewide (M.G.L. c. 40A §3; 760 CMR 71.00, effective Feb 2025). Estimated maximum ADU size for this property: 900 sq ft (the lesser of 900 sq ft or half the 8,540 sq ft principal dwelling). Lot size: 20,051 sq ft.
Based on listing data, which indicates the property type — not the zoning district. Local dimensional, septic (Title 5), and historic-district requirements still apply. Not legal advice — verify with the municipality.
Listing Agent: Kim Covino & Co. Team
Listing Office: Compass
MLS® Number: 73573670
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