Active
26 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.

Key facts

It was listed on September 8, 2026. The annual property taxes are $29,834 (2025 tax year). It sits on a 0.46-acre (20,051 sq ft) lot.

Immersive Experience

Open Houses

Market Value Analysis

This Property
Size (SqFt) →Price →
This Property$369/sqft
Local Avg (Winchester)$588/sqft
37% 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
Primary 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

Primary 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

Sold
$1,455,000

Sep 16, 2011

MLS® 71228382

Listed
$1,599,999

May 6, 2011

MLS® 71228382

Terminated
$1,899,999

May 2, 2011

MLS® 71012550

Listed
$1,899,999

Dec 23, 2009

MLS® 71012550

Questions about this home

When was 37 Mayflower Road, Winchester listed?

37 Mayflower Road, Winchester was listed on September 8, 2026.

Has the price of 37 Mayflower Road, Winchester changed?

The price hasn't changed since it was listed at $3,149,000.

What are the property taxes for 37 Mayflower Road, Winchester?

The annual property taxes for 37 Mayflower Road, Winchester are $29,834 (2025 tax year).

How big is the lot at 37 Mayflower Road, Winchester?

37 Mayflower Road, Winchester sits on a 0.46-acre (20,051 sq ft) lot.

What is the status of 37 Mayflower Road, Winchester?

37 Mayflower Road, Winchester is actively listed for sale.

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

2,698 housing units permitted in the last 12 months (+3% vs the prior 12 months) — 1,713 in 5+ unit buildings

U.S. Census Bureau, Building Permits Survey (through Jul '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