Active
27 Days on market
4 Churchill Road Winchester — Photo 1 of 42

4 Churchill Road Winchester — Photo 1 of 42

Recent Drop: $50,000

$1,699,000
$1,649,000

$1,649,000

4 Churchill Road, Winchester, MA 01890

Winchester, MA 01890

Beds

3

Baths

2

SqFt

2,421

Style

Single Family

Built

1954

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.

Key facts

It was listed on September 7, 2026. The price has come down from an original $1,699,000 to $1,649,000, most recently on September 30, 2026. The annual property taxes are $13,397 (2025 tax year). It sits on a 0.23-acre (10,001 sq ft) lot.

Immersive Experience

Open Houses

Market Value Analysis

This Property
Size (SqFt) →Price →
This Property$681/sqft
Local Avg (Winchester)$555/sqft
23% AboveMarket Average

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

Property Details

Financials

Original Price$1,699,000
Annual Taxes$13,397

Parking

Garage2
Off-Street8

Interior Specifications

Total Rooms7
Fireplaces2
FlooringHardwood
BasementFull, Partially Finished, Walk-Out Access, Interior Entry, Garage Access

Climate & Utilities

HeatingBaseboard, Natural Gas
CoolingCentral Air
WaterPublic
SewerPublic Sewer

Building & Exterior

ConstructionFrame
Roof--
FoundationConcrete Perimeter, Block
ZoningRDB

Property & Lot

Acres0.23
SqFt Lot10,001
Lot FeaturesLevel

Amenities & Appliances

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

Neighborhood

Public Transportation • Shopping • Pool • Tennis Court(s) • Park • Walk/Jog Trails

Geography

Floorplan Breakdown

Structural Layout

Second
Primary BedroomBedroom 2Bathroom 2
First
Living RoomDining RoomKitchenBedroom 3Bathroom 1
Main,First
Family Room
Living Room
Lvl First

18 x 12

Flooring - Hardwood, Lighting - Sconce

Dining Room
Lvl First

15 x 11

Closet, Flooring - Hardwood, Chair Rail, Lighting - Overhead

Kitchen
Lvl First

23 x 11

Flooring - Hardwood, Pantry, Countertops - Stone/Granite/Solid, Breakfast Bar / Nook, Exterior Access, Recessed Lighting, Stainless Steel Appliances, Gas Stove, Peninsula

Family Room
Lvl Main,First

28 x 20

Vaulted Ceiling(s), Flooring - Hardwood, Window(s) - Picture, Balcony / Deck, French Doors, Deck - Exterior, Open Floorplan, Recessed Lighting

Primary Bedroom
Lvl Second

15 x 15

Closet, Flooring - Hardwood, Lighting - Overhead

Bedroom 2
Lvl Second

15 x 12

Bedroom 3
Lvl First

11 x 11

Closet, Flooring - Hardwood, Lighting - Overhead

Bathroom 1
Lvl First

8 x 7

Bathroom - Full

Bathroom 2
Lvl Second

8 x 6

Bathroom - Full

Property History

Price Drop
$1,649,000

Was $1,699,000

Sep 30, 2026

MLS® 73572661

Listed
$1,699,000

Sep 7, 2026

MLS® 73572661

Questions about this home

When was 4 Churchill Road, Winchester listed?

4 Churchill Road, Winchester was listed on September 7, 2026.

Has the price of 4 Churchill Road, Winchester changed?

The price has come down from an original $1,699,000 to $1,649,000, most recently on September 30, 2026.

What are the property taxes for 4 Churchill Road, Winchester?

The annual property taxes for 4 Churchill Road, Winchester are $13,397 (2025 tax year).

How big is the lot at 4 Churchill Road, Winchester?

4 Churchill Road, Winchester sits on a 0.23-acre (10,001 sq ft) lot.

What is the status of 4 Churchill Road, Winchester?

4 Churchill 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 2,421 sq ft principal dwelling). Lot size: 10,001 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: 73572661