Active
5 Days on market
26 Mayflower Road Winchester — Photo 1 of 42

26 Mayflower Road Winchester — Photo 1 of 42

$1,950,000

26 Mayflower Road, Winchester, MA 01890

Winchester, MA 01890

Beds

5

Baths

4

SqFt

3,371

Style

Single Family

Built

1962

Welcome to 26 Mayflower Road, located in one of Winchester’s sought-after neighborhoods alongside Winchester Country Club. From the beautifully landscaped grounds to the updated front door, garage doors, and recently redone front steps, this home offers wonderful curb appeal from the moment you arrive. Inside, the main level is warm, inviting, and filled with natural light, featuring a comfortable living room with wood-burning fireplace, an open kitchen and dining area, and a sun-filled family room that opens directly to a private brick patio. Whether you're enjoying your morning coffee, grilling, gathering with friends, or simply relaxing at the end of the day, the indoor-outdoor flow makes this home especially easy to enjoy. The spacious primary suite offers double closets and a beautiful bath with double vanity sinks, soaking tub, and tiled walk-in shower. An attached guest/in-law suite with its own private entrance, full bath, and kitchenette provides exceptional flexibility for guests, extended family, an au pair, or a private work-from-home space. The finished lower level adds even more room to spread out, with two additional living spaces and a full bathroom—perfect for a teen suite, home office, gym, playroom, or media space. Outside, beautiful landscaping, irrigation, and the expansive brick patio create a private setting for entertaining or simply enjoying the outdoors. Ideally located near commuter routes, the MBTA Commuter Rail, shopping, restaurants, schools, and downtown Winchester, this is a home that offers the space and flexibility to fit the way you live, all in a location that makes getting where you need to go easy.

Key facts

It was listed on September 29, 2026. The annual property taxes are $20,383 (2026 tax year). It sits on a 0.38-acre (16,614 sq ft) lot.

Open Houses

Market Value Analysis

This Property
Size (SqFt) →Price →
This Property$578/sqft
Local Avg (Winchester)$540/sqft
7% AboveMarket Average

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

Property Details

Financials

Original Price$1,950,000
Annual Taxes$20,383

Parking

Garage2
Off-Street6

Interior Specifications

Total Rooms11
Fireplaces2
FlooringTile, Laminate, Hardwood, Flooring - Hardwood
BasementFull, Finished, Walk-Out Access, Bulkhead

Climate & Utilities

HeatingBaseboard, Oil, Ductless
CoolingCentral Air
WaterPublic
SewerPublic Sewer

Building & Exterior

ConstructionFrame
RoofShingle
FoundationConcrete Perimeter
ZoningRDA

Property & Lot

Acres0.38
SqFt Lot16,614
Lot Features--

Amenities & Appliances

Oven • Dishwasher • Microwave • Range • Refrigerator • Washer • Dryer

Neighborhood

Park • Walk/Jog Trails • Golf • Conservation Area • Highway Access • House of Worship

Geography

Floorplan Breakdown

Structural Layout

Third
Primary BedroomBedroom 4Bathroom 2
Second
Bedroom 2Bedroom 3Bathroom 1
First
Living RoomDining RoomKitchenFamily Room
Basement
OfficeBathroom 3
Living Room
Lvl First

Closet, Flooring - Hardwood, Recessed Lighting, Crown Molding

Dining Room
Lvl First

Flooring - Hardwood, Lighting - Overhead, Crown Molding

Kitchen
Lvl First

Flooring - Stone/Ceramic Tile, Countertops - Stone/Granite/Solid, Recessed Lighting, Stainless Steel Appliances, Peninsula

Office
Lvl Basement

Flooring - Laminate

Family Room
Lvl First

Flooring - Hardwood, Recessed Lighting, Lighting - Overhead, Crown Molding

Primary Bedroom
Lvl Third

Skylight, Closet - Linen, Closet, Flooring - Hardwood, Window(s) - Bay/Bow/Box, Lighting - Overhead, Window Seat

Bedroom 2
Lvl Second
Bedroom 3
Lvl Second

Closet, Flooring - Hardwood, Lighting - Overhead

Bedroom 4
Lvl Third

Closet, Flooring - Hardwood, Lighting - Overhead

Bathroom 1
Lvl Second

Bathroom - Full, Bathroom - Tiled With Shower Stall, Flooring - Stone/Ceramic Tile

Bathroom 2
Lvl Third

Bathroom - Full, Bathroom - Tiled With Tub & Shower, Flooring - Stone/Ceramic Tile, Countertops - Stone/Granite/Solid, Jacuzzi / Whirlpool Soaking Tub, Double Vanity

Bathroom 3
Lvl Basement

Bathroom - Full, Bathroom - With Shower Stall, Flooring - Stone/Ceramic Tile

Questions about this home

When was 26 Mayflower Road, Winchester listed?

26 Mayflower Road, Winchester was listed on September 29, 2026.

Has the price of 26 Mayflower Road, Winchester changed?

The price hasn't changed since it was listed at $1,950,000.

What are the property taxes for 26 Mayflower Road, Winchester?

The annual property taxes for 26 Mayflower Road, Winchester are $20,383 (2026 tax year).

How big is the lot at 26 Mayflower Road, Winchester?

26 Mayflower Road, Winchester sits on a 0.38-acre (16,614 sq ft) lot.

What is the status of 26 Mayflower Road, Winchester?

26 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 3,371 sq ft principal dwelling). Lot size: 16,614 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: Nicole M. Condon

Listing Office: The Simply Sold Realty Co.

MLS® Number: 73584117