Active
3 Days on market
37 Mayflower Road Winchester — Photo 1 of 42

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

This Property
Size (SqFt) →Price →
This Property$369/sqft
Local Avg (Winchester)$555/sqft
34% BelowMarket Average

* Analysis is based on 24 actively listed and recently sold comparable properties strictly within Winchester, MA.

Property Details

Financials

Original Price$3,149,000
Annual Taxes$29,834

Parking

Garage3
Off-Street12

Interior Specifications

Total Rooms13
Fireplaces4
FlooringTile, Hardwood, Flooring - Hardwood, Flooring - Stone/Ceramic Tile
BasementFull, Finished, Walk-Out Access, Interior Entry

Climate & Utilities

HeatingForced Air, Natural Gas, Fireplace(s), Fireplace
CoolingCentral Air
WaterPublic
SewerPublic Sewer

Building & Exterior

ConstructionFrame
RoofShingle
FoundationConcrete Perimeter
ZoningRDA

Property & Lot

Acres0.46
SqFt Lot20,051
Lot FeaturesCul-De-Sac

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

Second
Master BedroomBedroom 2Bedroom 3Bedroom 4Bedroom 5Bathroom 2Bathroom 3
First
Living RoomDining RoomKitchenOfficeFamily RoomBathroom 1
Living Room
Lvl First

20 x 16

Flooring - Hardwood, Lighting - Sconce

Dining Room
Lvl First

20 x 15

Flooring - Hardwood, Lighting - Sconce, Lighting - Pendant

Kitchen
Lvl First

22 x 13

Flooring - Hardwood, Countertops - Upgraded, Kitchen Island, Breakfast Bar / Nook, Country Kitchen, Exterior Access, Recessed Lighting, Lighting - Pendant, Lighting - Overhead

Office
Lvl First

16 x 14

Fireplace, Flooring - Hardwood, Wet bar

Family Room
Lvl First

21 x 18

Ceiling Fan(s), Flooring - Hardwood, Recessed Lighting, Lighting - Sconce

Master Bedroom
Lvl Second

30 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 Second

17 x 16

Bedroom 3
Lvl Second

22 x 17

Bathroom - Full, Ceiling Fan(s), Walk-In Closet(s), Closet/Cabinets - Custom Built, Flooring - Hardwood, Flooring - Stone/Ceramic Tile

Bedroom 4
Lvl Second

18 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 Second

15 x 15

Bathroom - Full, Ceiling Fan(s), Walk-In Closet(s), Flooring - Hardwood, Recessed Lighting

Bathroom 1
Lvl First

9 x 6

Walk-In Closet(s), Closet/Cabinets - Custom Built, Flooring - Stone/Ceramic Tile

Bathroom 2
Lvl Second

15 x 13

Bathroom - Full, Flooring - Stone/Ceramic Tile

Bathroom 3
Lvl Second

10 x 9

Bathroom - Full, Flooring - Stone/Ceramic Tile

Property History

Listed
$3,149,000

Sep 8, 2026

MLS® 73573670

Terminated
$3,179,000

Sep 3, 2026

MLS® 73502853

Listed
$3,179,000

Apr 16, 2026

MLS® 73502853

Terminated
$3,537,000

Apr 14, 2026

MLS® 73475646

Listed
$3,537,000

Feb 9, 2026

MLS® 73475646

Terminated
$1,899,999

May 2, 2011

MLS® 71012550

Listed
$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 Provided By

Listing Agent: Kim Covino & Co. Team

Listing Office: Compass

MLS® Number: 73573670

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