OPEN TODAY, 5PM TO 6:30PM

For sale

$1,850,000

Est. $11,939/mo —

•

3,092

sq ft

1 Overlook Way, Winchester, MA 01890

About this home

Welcome to One Overlook Way in Winchester. This spacious 4+ bedroom center-entrance Colonial is tucked away on a short cul-de-sac off High Street, in a premier location close to Ambrose Elementary School and the Winchester Country Club. The foyer opens to a thoughtfully designed floor plan with wonderful flow for everyday living and entertaining. The generously sized eat-in kitchen features stone countertops and stainless steel appliances and connects to the beautiful dining room. The kitchen also opens naturally into the cozy family room - with gas fireplace, custom built-ins and access to the back and side yard, the family room will be well utilized! A larger front-to-back living room with fireplace and box windows is located off the foyer and is complemented by an adjoining oversized library or playroom. Upstairs, the spacious primary suite offers a private bath with double vanity, full shower and great closet space. Three additional bedrooms feature hardwood floors, generous closets and access to a shared full bath. The third-floor bonus space provides flexible room for guests, a home office or storage. The finished lower level adds even more usable space, with a fireplace and room for exercise, hobbies or relaxation. Enjoy the outdoors in this large, level yard with established plantings, brick patio and plenty of space to entertain. There is a two-car garage plus 300+sf of unfinished space above the garage. Please ask the agent for more information. This home truly has it all. This is one home you do not want to miss.

Single-familyProperty Type

1941Year Built

0.36 acresLot Size

$598Price/Sq.Ft.

2 garage spacesParking

Listed by Lynne Russo • Better Homes and Gardens Real Estate - The Shanahan Group

Listed by • Better Homes and Gardens Real Estate - The Shanahan Group

Listing updated: Sep 23, 2026 at 06:33pm

Redfin checked: a few seconds ago

•Source:MLS PIN #73581571

Payment calculator

$11,939 per month

Principal and interest$10,222

Property taxes

$1,471

HOA dues

Home insurance

$247

Utilities

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Open houses

Thursday, Sep 24

5:00pm - 6:30pm

Friday, Sep 25

12:00pm - 1:30pm

Saturday, Sep 26

11:00am - 12:30pm

Sunday, Sep 27

12:00pm - 1:30pm

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Around this home

Schools

K - 12
Preschool & daycare

Ambrose Elementary School

Public K-5 • Assigned • 0.3mi

10/10

McCall Middle School

Public 6-8 • Assigned • 1.4mi

9/10

Winchester High School

Public 9-12 • Assigned • 1.6mi

10/10

Provided by GreatSchools

About

Wedgemere

Wedgemere, located between Woburn Street and the Aberjona River, is a residential and commuter-friendly Winchester neighborhood with a leafy streetscape and a rail-stop rhythm. The neighborhood’s character concentrates around the Wedgemere Station area on Wedgemere Avenue, where morning foot traffic, dog walkers, and passing trains set a steady cadence. Early-20th-century Colonials and Capes line curving blocks, with stone walls and mature trees shaping the streetscape. The Aberjona River corridor and nearby trails add a green edge for walks and runs. For local pillars, the Winchester Community Music School, Wright-Locke Farm, and the Griffin Museum of Photography anchor culture beyond the commute.

Provided by Walk Score and Local Logic

Market insights

1 Overlook Way · $1,850,000

DAYS ON MARKET

The average home goes pending in 22 days.

SALE-TO-LIST

Most homes are selling 1% above list price.

LIST PRICE

Median sale price in this area is $919,982. (50% lower than this home)

PRICE DROP

18% of homes in this area have had a price drop in the past month.

Property details

Interior
Exterior
Finance

Kitchen

Bathroom

Bedroom

Living

Dining

Interior features
Custom built closets and cabinets
Walk-in closets
Cedar closet(s)
Ample storage
Library
Bonus room
Play room
Walk-up attic
Skylight
Window screens
Three fireplaces (in family room and living room)
Open floorplan
Recessed lighting

Bedrooms
Master bedroom on second floor with hardwood flooring, double vanity, ceiling fan and double closet
Second bedroom on second floor with hardwood flooring and double closet
Third bedroom on second floor with hardwood flooring, attic access and double closet
Fourth bedroom on second floor with hardwood flooring and closet

Bathrooms
Two full bathrooms (second-floor full baths feature tiled tub & shower)
One half bathroom on the main level with stone/ceramic tile flooring
Master suite includes a full master bathroom

Kitchen
Stone/granite countertops
Stainless steel appliances
Dining area in kitchen
Bay/Bow/Box window
Stone/ceramic tile flooring
Recessed lighting

Laundry & utility
Washer and dryer included
Washer hookup
Gas dryer hookup
Laundry located in basement

Flooring
Hardwood and engineered hardwood
Wood flooring
Tile (stone/ceramic)
Laminate
Wall-to-wall carpet

Heating & cooling
Central heating
Baseboard heating
Natural gas and electric heating options
Ductless cooling
Fireplace heating

Sale and tax history for 1 Overlook Way

Sale History
Tax History

Year

Property tax

Land + Additions

Assessment*

2026

$17,650 (+3.4%)

$961,800 + $631,200

$1,593,000

2025

$17,068 (+11.4%)

$924,800 + $614,200

$1,539,000

2023

$15,327 (+2.6%)

$850,800 + $567,100

$1,417,900

2022

$14,938 (−2.5%)

$665,900 + $528,200

$1,194,100

2021

$15,320 (+6.9%)

$665,900 + $528,200

$1,194,100

2020

$14,336 (+9.3%)

$628,900 + $528,200

$1,157,100

2019

$13,116 (+2.7%)

$554,900 + $528,200

$1,083,100

2018

$12,768 (+1.2%)

$534,600 + $512,800

$1,047,400

2017

$12,621 (+13.3%)

$534,600 + $493,200

$1,027,800

2016

$11,138 (+3.0%)

$476,300 + $477,300

$953,600

2015

$10,818 (+6.5%)

$432,800 + $458,300

$891,100

2014

$10,161 (+0.7%)

$360,700 + $441,900

$802,600

2013

$10,087 (+1.8%)

$360,700 + $429,200

$789,900

2012

$9,913 (+3.7%)

$360,700 + $429,200

$789,900

2011

$9,558 (+2.8%)

$360,700 + $429,200

$789,900

2010

$9,295 (+2.1%)

$386,600 + $421,000

$807,600

2009

$9,102

$386,600 + $421,000

$807,600

Public record

Beds

Baths

2.5

Stories

Lot width

—

Lot depth

—

Lot size

0.36 Acres

Year renovated

—

Finished Sq. Ft.

2,828

Unfinished Sq. Ft.

—

Total Sq. Ft.

2,828

Year built

1941

Style

Single Family Residential

County

Middlesex County

APN

601325S

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Sep 23, 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 days above 98° expected this year, 15 days in 30 years

6/10 Wind Factor

54% chance of strong winds in next 30 years

3/10 Air Factor

2 unhealthy days expected this year, 3 days in 30 years

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 9.2 hours in June and 4.4 hours in December, placing it below the U.S. average for solar exposure.

9.2 hrs

4.4 hrs

JuneDecember

Provided by Shadowmap

Redfin Estimate for 1 Overlook Way

$1,847,984

$2,016 under list price of $1.85M

Nearby comparable homes

The Redfin Estimate uses 6 recent nearby sales, priced between $1.5M to $2.2M.

SOLD JUL 9, 2026
$2,025,000 Last sold price
5 beds5 baths3,956 sq ft
36 Cambridge St, Winchester, MA 01890
$86/sq ft
85 years newer
SOLD AUG 14, 2026
$2,200,000 Last sold price
4 beds2.5 baths3,123 sq ft
15 Cabot St, Winchester, MA 01890
$106/sq ft
smaller lot
37 years older
SOLD AUG 3, 2026
$1,825,000 Last sold price
2 beds3.5 baths3,874 sq ft
10 Graystone Cir #10, Winchester, MA 01890
$127/sq ft
69 years newer
SOLD OCT 31, 2025
$1,750,000 Last sold price
4 beds2.5 baths2,397 sq ft
15 Westland Ave, Winchester, MA 01890
$132/sq ft
smaller lot
4 years older
SOLD APR 29, 2026
$1,475,000 Last sold price
3 beds2 baths2,344 sq ft
28 Emerson Rd, Winchester, MA 01890
$31/sq ft
smaller lot
11 years newer
SOLD DEC 30, 2025
$1,865,000 Last sold price
7 beds2.5 baths2,998 sq ft
1 Copley St, Winchester, MA 01890
$24/sq ft
smaller lot
28 years older

Rental earnings

Est. $5,200 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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