
4 Churchill Road Winchester — Photo 1 of 42
Recent Drop: $50,000
$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
* Analysis is based on 24 actively listed and recently sold comparable properties strictly within Winchester, MA.
Property Details
Financials
Parking
Interior Specifications
Climate & Utilities
Building & Exterior
Property & Lot
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
Living Room
Lvl First18 x 12
Flooring - Hardwood, Lighting - Sconce
Dining Room
Lvl First15 x 11
Closet, Flooring - Hardwood, Chair Rail, Lighting - Overhead
Kitchen
Lvl First23 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,First28 x 20
Vaulted Ceiling(s), Flooring - Hardwood, Window(s) - Picture, Balcony / Deck, French Doors, Deck - Exterior, Open Floorplan, Recessed Lighting
Primary Bedroom
Lvl Second15 x 15
Closet, Flooring - Hardwood, Lighting - Overhead
Bedroom 2
Lvl Second15 x 12
Bedroom 3
Lvl First11 x 11
Closet, Flooring - Hardwood, Lighting - Overhead
Bathroom 1
Lvl First8 x 7
Bathroom - Full
Bathroom 2
Lvl Second8 x 6
Bathroom - Full
Property History
$1,649,000
Was $1,699,000
Sep 30, 2026
MLS® 73572661
$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 Agent: Kim Covino & Co. Team
Listing Office: Compass
MLS® Number: 73572661







