For sale

$1,649,000

Est. $10,560/mo —

•

2,421

sq ft

4 Churchill Rd, Winchester, MA 01890

About this home

Price Change!! **Open House this weekend or call for private showings** Great offering~ Extensively rebuilt and expanded, this impeccably maintained 3/4 Bed 2 BA home offers a spacious and versatile floor plan. The impressive 28’ x 20’ great room features vaulted ceilings, bay window, and a gas fireplace which flows nicely from the updated kitchen. Step outside to a new oversized Azek deck with plenty of room for grilling, dining, and relaxing. The main level also includes formal living and dining rooms, plus a bedroom & full bath. The formal dining room offers flexibility to serve as a fourth bedroom, if desired. Upstairs are two generously sized bedrooms with hardwood floors and ample closet space, along with a spacious hall bath featuring a skylight. Additional highlights include a finished lower level, laundry and storage areas, and direct access to a two-car garage. Beautifully landscaped grounds feature perennial gardens, flowering trees, natural stone walls, and exceptional privacy—nestled into one of Winchester’s most desired neighborhoods, all just 7 miles from Boston with convenient access to the town center, Fells trails, major routes and highways. Please see feature/ update list attached.

Single-familyProperty Type

1954Year Built

10,001 sq ftLot Size

$681Price/Sq.Ft.

2 garage spacesParking

Listed by Kim Covino & Co. Team • Compass

Listed by Kim Covino • Compass

Listing updated: Oct 11, 2026 at 10:35am

Redfin checked: a minute ago

•Source:MLS PIN #73572661

Payment calculator

$10,560 per month

Principal and interest$9,224

Property taxes

$1,116

HOA dues

Home insurance

$220

Utilities

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Open houses

No upcoming open houses.

Nearby open houses (10)

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Around this home

Schools

K - 12
Preschool & daycare

Muraco Elementary School

Public K-5 • Assigned • 1.0mi

9/10

McCall Middle School

Public 6-8 • Assigned • 1.7mi

9/10

Winchester High School

Public 9-12 • Assigned • 1.4mi

10/10

Provided by GreatSchools

About Winchester

Highlands

Winchester Highlands, located between the Middlesex Fells Reservation and Winchester Center, is a residential and wooded Winchester neighborhood with hillside streets and pocket parks. The neighborhood’s character concentrates around the Cambridge Street and Main Street junction, where small storefronts, cafés, and everyday errands cluster in a compact, walkable strip. Book Ends and the Winchester Community Music School act as cultural touchstones, with Wright-Locke Farm adding a seasonal, local-food rhythm nearby. Housing reads as classic New England—Colonial and Cape silhouettes, mature trees, and stone walls along curving roads. Trails and overlooks in the Fells shape the daily backdrop, while the town center’s civic buildings and shops keep the pace grounded.

Provided by Walk Score and Local Logic

Offer insights

4 Churchill Rd · $1,649,000

Strong offer

$1.64M and above

75% chance or better to win

Why $1.64M+ is a strong offer

DAYS ON MARKET

The average home goes pending in 23 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
Living/dining room combo
Insulated doors
Insulated windows with screens
Recessed lighting
Sconce lighting
Overhead lighting

Bedrooms
Primary bedroom on second floor with hardwood flooring, closet, and overhead lighting
Second bedroom on second floor with hardwood flooring, closet, and overhead lighting
Third bedroom on first floor with hardwood flooring, closet, and overhead lighting

Bathrooms
Two full bathrooms (one on first floor, one on second floor)

Kitchen
Hardwood floors
Stone/granite/solid countertops
Pantry
Breakfast bar / nook
Peninsula
Exterior access
Stainless steel appliances
Gas stove
Recessed lighting

Laundry & utility
Washer hookup in basement
Laundry area approximately 20 x 10 in basement

Flooring
Hardwood flooring throughout main living areas and bedrooms

Heating & cooling
Baseboard heating (natural gas)
Central air conditioning

Sale and tax history for 4 Churchill Rd

Sale History
Tax History

Year

Property tax

Land + Additions

Assessment*

2026

$13,569 (+1.3%)

$759,000 + $465,600

$1,224,600

2025

$13,397 (+11.2%)

$759,000 + $449,000

$1,208,000

2023

$12,049 (−0.9%)

$660,000 + $447,600

$1,107,600

2022

$12,155 (+2.7%)

$544,500 + $427,100

$971,600

2021

$11,831 (+3.6%)

$495,000 + $427,100

$922,100

2020

$11,425 (+11.7%)

$495,000 + $427,100

$922,100

2019

$10,228 (+1.9%)

$417,500 + $427,100

$844,600

2018

$10,041 (+2.6%)

$410,000 + $413,700

$823,700

2017

$9,788 (+9.7%)

$410,000 + $387,100

$797,100

2016

$8,922 (+3.1%)

$390,200 + $373,700

$763,900

2015

$8,650 (+2.2%)

$354,800 + $357,700

$712,500

2014

$8,467 (+6.8%)

$321,800 + $347,000

$668,800

2013

$7,930 (+1.7%)

$284,600 + $336,400

$621,000

2012

$7,794 (+3.7%)

$284,600 + $336,400

$621,000

2011

$7,514 (+2.8%)

$284,600 + $336,400

$621,000

2010

$7,312 (+2.1%)

$300,100 + $335,200

$635,300

2009

$7,160

$300,100 + $335,200

$635,300

Public record

Beds

Baths

Stories

Lot width

—

Lot depth

—

Lot size

10,019 Sq. Ft.

Year renovated

—

Finished Sq. Ft.

2,327

Unfinished Sq. Ft.

—

Total Sq. Ft.

2,327

Year built

1954

Style

Single Family Residential

County

Middlesex County

APN

2786819S

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

3/10 Fire Factor

0.15% chance of being in a wildfire in next 30 years

5/10 Heat Factor

7 days above 96° 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

84/ 100

Very good sunlight

Sunscore

This home receives average direct sun exposure in Winchester. There appears to be minimal shading by surrounding buildings, terrain, and vegetation.

8.8 hrs

4.3 hrs

JuneDecember

Provided by Shadowmap

Redfin Estimate for 4 Churchill Rd

$1,585,563

$63K under list price of $1.65M

Nearby comparable homes

The Redfin Estimate uses 6 recent nearby sales, priced between $752K to $1.2M.

SOLD JUL 30, 2026
$1,170,000 Last sold price
5 beds1.5 baths2,688 sq ft
6 Hancock St, Winchester, MA 01890
$246/sq ft
smaller lot
64 years older
SOLD JUL 8, 2026
$1,030,000 Last sold price
4 beds2.5 baths2,240 sq ft
6 Packard St, Woburn, MA 01801
$221/sq ft
larger lot
40 years newer
SOLD JUL 28, 2026
$860,000 Last sold price
4 beds3 baths2,200 sq ft
92 Garfield Ave, Woburn, MA 01801
$290/sq ft
smaller lot
1 year older
SOLD JUN 26, 2026
$752,000 Last sold price
4 beds2 baths2,058 sq ft
13 Wright St, Stoneham, MA 02180
$316/sq ft
smaller lot
104 years older
SOLD SEP 18, 2026
$1,035,000 Last sold price
4 beds1.5 baths1,777 sq ft
46 Clark St, Winchester, MA 01890
$99/sq ft
smaller lot
33 years older
SOLD AUG 21, 2026
$885,000 Last sold price
3 beds2 baths2,005 sq ft
4 Laurel St, Woburn, MA 01801
$240/sq ft
3 years newer

Rental earnings

Est. $4,580 per month, based on comparable rentals

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Early Access listings

EARLY ACCESSCOMPASS COMING SOON

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17 Churchill Rd, Winchester, MA 01890

OPEN SUN, 11:30AM TO 1PM3D WALKTHROUGH

$2,199,000

4 beds3.5 baths3,570 sq ft

19 Hancock St, Winchester, MA 01890

New listings for sale in 01890

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

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