276 High Street Winchester — Photo 1 of 36
Recent Drop: $104,000
$2,195,000
276 High Street, Winchester, MA 01890
Winchester, MA 01890 — Cox Road / High St Extension neighborhood
Beds
5
Baths
3.5
SqFt
5,006
Style
Single Family
Built
1992
Discover this beautiful home with all the space you've been looking for! Set on a private half-acre lot in a serene cul-de-sac near the Winchester/Lexington border. This residence offers unparalleled privacy & is surrounded by nature. This home includes 5 bedrooms, 3.5 bathrooms & an oversized 3 car garage! The spacious grounds feature delightful front & back yards, a generous deck, & a charming gazebo, all beside Whipple Hill & Smith Pond w/ miles of walking trails nearby! Inside you will find a thoughtfully designed floor plan for every day living & entertaining featuring a sunken living room, sunny home office, lovely formal dining room & oversized family kitchen w dining area showcasing walls of windows overlooking the stunning rear yard & an adjacent family room w/ wood burning fireplace. The oversized primary suite incudes a walk in closet & spacious bath. Just 7 miles from Boston, Winchester is known for top-rated schools & great quality of life. Don't miss this fabulous home!
Key facts
It was listed on April 6, 2026. The price has come down from an original $2,299,000 to $2,195,000, most recently on May 13, 2026. The annual property taxes are $23,217 (2025 tax year). It sits on a 0.46-acre (19,998 sq ft) lot.
Immersive Experience
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
Water Heater • Range • Oven • Dishwasher • Disposal • Trash Compactor • Microwave • Refrigerator • Freezer • Washer • Dryer • Plumbed For Ice Maker
Neighborhood
Public Transportation • Shopping • Tennis Court(s) • Park • Golf • Bike Path
Geography
Floorplan Breakdown
Structural Layout
Living Room
Lvl First15 x 14
Flooring - Hardwood, Open Floorplan, Sunken, Lighting - Overhead
Dining Room
Lvl First15 x 15
Flooring - Hardwood, Window(s) - Picture, French Doors, Lighting - Pendant, Lighting - Overhead
Kitchen
Lvl Main,First16 x 15
Closet/Cabinets - Custom Built, Flooring - Stone/Ceramic Tile, Countertops - Stone/Granite/Solid, French Doors, Kitchen Island, Breakfast Bar / Nook, Exterior Access, Open Floorplan, Recessed Lighting, Stainless Steel Appliances, Lighting - Pendant
Office
Lvl First14 x 11
Closet, Flooring - Hardwood, Lighting - Overhead
Family Room
Lvl First30 x 22
Ceiling Fan(s), Flooring - Hardwood, Balcony / Deck, Deck - Exterior, Exterior Access, Lighting - Overhead
Primary Bedroom
Lvl Second26 x 23
Bathroom - Full, Bathroom - Double Vanity/Sink, Closet - Linen, Flooring - Stone/Ceramic Tile, French Doors, Lighting - Sconce, Lighting - Overhead
Bedroom 2
Lvl Second17 x 14
Bedroom 3
Lvl Second15 x 13
Ceiling Fan(s), Closet, Lighting - Overhead
Bedroom 4
Lvl Second14 x 12
Ceiling Fan(s), Closet, Lighting - Overhead
Bedroom 5
Lvl Third24 x 22
Ceiling Fan(s), Closet, Lighting - Overhead
Bathroom 1
Lvl First8 x 5
Bathroom - Half
Bathroom 2
Lvl Second13 x 12
Bathroom - Full, Bathroom - Double Vanity/Sink, Bathroom - Tiled With Shower Stall, Bathroom - Tiled With Tub, Closet, Flooring - Stone/Ceramic Tile, Jacuzzi / Whirlpool Soaking Tub
Bathroom 3
Lvl Second9 x 9
Bathroom - Full, Bathroom - Double Vanity/Sink, Bathroom - Tiled With Tub & Shower
Property History
$2,195,000
Was $2,299,000
May 13, 2026
MLS® 73496396
$2,299,000
Apr 6, 2026
MLS® 73496396
$2,299,000
Dec 16, 2025
MLS® 73404344
$2,299,000
Jul 14, 2025
MLS® 73404344
$2,399,000
Jun 16, 2025
MLS® 73349101
$2,399,000
Mar 24, 2025
MLS® 73349101
$2,750,000
Dec 31, 2024
MLS® 73170437
$2,750,000
Oct 14, 2023
MLS® 73170437
Questions about this home
When was 276 High Street, Winchester listed?
276 High Street, Winchester was listed on April 6, 2026.
Has the price of 276 High Street, Winchester changed?
The price has come down from an original $2,299,000 to $2,195,000, most recently on May 13, 2026.
What are the property taxes for 276 High Street, Winchester?
The annual property taxes for 276 High Street, Winchester are $23,217 (2025 tax year).
How big is the lot at 276 High Street, Winchester?
276 High Street, Winchester sits on a 0.46-acre (19,998 sq ft) lot.
What is the status of 276 High Street, Winchester?
276 High Street, 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 5,006 sq ft principal dwelling). Lot size: 19,998 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: 73496396
