OPEN TODAY, 4:30PM TO 6PM

For sale

$1,950,000

Est. $13,000/mo —

•

3,371

sq ft

26 Mayflower Rd, Winchester, MA 01890

About this home

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.

Single-familyProperty Type

1962Year Built

0.38 acresLot Size

$578Price/Sq.Ft.

2 garage spacesParking

Listed by Nicole Condon • The Simply Sold Realty Co.

Listed by • The Simply Sold Realty Co.

Listing updated: Sep 29, 2026 at 07:45pm

Redfin checked: 3 minutes ago

•Source:MLS PIN #73584117

Payment calculator

$13,000 per month

Principal and interest$11,042

Property taxes

$1,699

HOA dues

Home insurance

$260

Utilities

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See this home in person

Open houses

Thursday, Oct 1

4:30pm - 6:00pm

Saturday, Oct 3

11:00am - 12:30pm

Sunday, Oct 4

11:00am - 12:30pm

Nearby open houses (10)

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Around this home

Schools

K - 12
Preschool & daycare

Vinson-Owen Elementary School

Public PreK-5 • Assigned • 0.7mi

9/10

McCall Middle School

Public 6-8 • Assigned • 1.8mi

9/10

Winchester High School

Public 9-12 • Assigned • 2.1mi

10/10

Provided by GreatSchools

About West

Side

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

Offer insights

26 Mayflower Rd · $1,950,000

Strong offer

$2.06M and above

75% chance or better to win

Why $2.06M+ is a strong offer

DAYS ON MARKET

The average home goes pending in 22 days.

SALE-TO-LIST

Most homes are selling 1% above list price.

About offer insights

Property details

Interior
Exterior
Finance

Kitchen

Bathroom

Bedroom

Living

Dining

Interior features
11 total rooms
Recessed lighting
Crown molding
Closets throughout
Accessory apartment
Den
Home office
Walk-up attic

Bedrooms
Primary bedroom on the third level with skylight, bay/bow/box window, window seat, linen closet and hardwood floors
Second-floor bedroom with hardwood floors and overhead lighting
Second-floor bedroom with hardwood floors and overhead lighting
Third-floor bedroom with hardwood floors and overhead lighting

Bathrooms
Four full bathrooms
Bathrooms feature stone/ceramic tile flooring
One bathroom has a tiled shower stall
One bathroom has a tub and shower, stone/granite countertops, double vanity and Jacuzzi/whirlpool soaking tub
Basement full bathroom with shower stall

Kitchen
Stone/granite countertops
Tile flooring
Peninsula
Recessed lighting
Stainless steel appliances
Oven, Range, Microwave, Dishwasher, Refrigerator

Laundry & utility
Washer and dryer included
Washer hookup
Electric dryer hookup
Laundry located in the basement

Flooring
Hardwood flooring in main living areas and bedrooms
Tile (stone/ceramic) flooring in bathrooms and kitchen
Laminate flooring in basement office

Heating & cooling
Heating: baseboard and oil with ductless options
Cooling: central air

Sale and tax history for 26 Mayflower Rd

Sale History
Tax History

Date

Event

Price

MLS PIN #73584117

Sep 29, 2026

Listed

$1,950,000

$578/sq ft

MLS PIN #72027320

Sep 15, 2016

Sold

$1,185,000

$352/sq ft

Jul 22, 2016

Pending

—

Jun 22, 2016

Listed

$1,199,000

$356/sq ft

+13

Looking for a beautifully maintained home on a gorgeous lot? This outstanding house is absolutely fabulous with its versatile floor plan for the active family. Located in "Birch Knoll", adjacent to the Country Club golf course and walking distance to the popular Vinson-Owen School, the major commuting routes are only minutes away. There is a family-room on the first floor plus an additional one on the lower level, complete with wood burning fireplace. and easy access to the large screened porch and lovely back yard. With updated kitchen and luxurious master suite, move right in and relax because the work has all been done. Come and share our enthusiasm for this fantastic home which shows pride of ownership from top to bottom, inside and out. We know you'll agree! A nice surprise are the seasonal views of the Boston skyline!

Year

Property tax

Land + Additions

Assessment*

2026

$20,383 (+3.7%)

$1,091,300 + $748,300

$1,839,600

2025

$19,659 (+12.3%)

$1,053,700 + $719,000

$1,772,700

2023

$17,499 (−1.0%)

$978,400 + $673,500

$1,651,900

2022

$17,680 (+9.1%)

$790,200 + $623,100

$1,413,300

2021

$16,202 (+6.7%)

$639,700 + $623,100

$1,262,800

2020

$15,180 (+5.5%)

$602,100 + $623,100

$1,225,200

2019

$14,382 (+8.5%)

$564,500 + $623,100

$1,187,600

2018

$13,260 (+21.5%)

$543,800 + $544,000

$1,087,800

2017

$10,913 (+6.7%)

$484,500 + $404,200

$888,700

2016

$10,232 (+8.0%)

$484,500 + $391,500

$876,000

2015

$9,476 (−3.2%)

$404,500 + $376,100

$780,600

2014

$9,793 (+5.7%)

$404,500 + $369,000

$773,500

2013

$9,265 (+1.8%)

$366,900 + $358,600

$725,500

2012

$9,105 (+3.7%)

$366,900 + $358,600

$725,500

2011

$8,779 (+1.5%)

$366,900 + $358,600

$725,500

2010

$8,649 (+2.1%)

$393,200 + $358,200

$751,400

2009

$8,468

$393,200 + $358,200

$751,400

Public record

Beds

Baths

Stories

Lot width

—

Lot depth

—

Lot size

0.38 Acres

Year renovated

—

Finished Sq. Ft.

3,371

Unfinished Sq. Ft.

—

Total Sq. Ft.

3,371

Year built

1962

Style

Single Family Residential

County

Middlesex County

APN

3791773S

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Sep 16, 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 hot days expected this year, 14 days in 30 years

Wind Factor

We're working on getting current and accurate wind risk information for this home.

Air Factor

We're working on getting current and accurate air risk information for this home.

Provided by First Street

Historical weather

Winchester, MA • 01890

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 9 hours in June and 4.4 hours in December, placing it below the U.S. average for solar exposure.

9 hrs

4.4 hrs

JuneDecember

Provided by Shadowmap

Redfin Estimate for 26 Mayflower Rd

$2,078,765

$129K over list price of $1.95M

Nearby comparable homes

The Redfin Estimate uses 6 recent nearby sales, priced between $1.2M to $2.1M.

BOUGHT WITH REDFIN MAY 8, 2026
$1,825,000 Last sold price
4 beds3.5 baths3,240 sq ft
143 Wright St, Arlington, MA 02474
$15/sq ft
smaller lot
55 years newer
SOLD APR 24, 2026
$2,150,000 Last sold price
6 beds3.5 baths3,464 sq ft
69 Edmund Rd, Arlington, MA 02474
$43/sq ft
larger lot
29 years older
SOLD APR 29, 2026
$1,475,000 Last sold price
3 beds2 baths2,344 sq ft
28 Emerson Rd, Winchester, MA 01890
$51/sq ft
smaller lot
10 years older
SOLD APR 29, 2026
$2,150,000 Last sold price
5 beds4 baths3,374 sq ft
72 Thesda St, Arlington, MA 02474
$59/sq ft
smaller lot
54 years newer
SOLD AUG 24, 2026
$1,200,000 Last sold price
5 beds2.5 baths2,730 sq ft
119 Ridge St, Arlington, MA 02474
$138/sq ft
smaller lot
2 years older
SOLD SEP 15, 2026
$1,857,000 Last sold price
3 beds3.5 baths2,513 sq ft
2 Olde Lyme Rd, Winchester, MA 01890
$161/sq ft
2 years older

Rental earnings

Est. $6,044 per month, based on comparable rentals

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Details provided by MLS PIN and may not match the public record. Learn more.

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