Active
136 Days on market
276 High Street Winchester — Photo 1 of 38
Recent Drop: $104,000
$2,299,000$2,195,000
$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!
Immersive Experience
Market Value Analysis
This Property
Size (SqFt) →Price →This Property$438/sqft
Local Avg (Winchester)$551/sqft
21% BelowMarket Average
* Analysis is based on 24 actively listed and recently sold comparable properties strictly within Winchester, MA.
Property Details
Financials
Original Price$2,299,000
Annual Taxes$23,217
Parking
Garage3
Off-Street9
Interior Specifications
Total Rooms11
Fireplaces1
FlooringTile, Carpet, Hardwood, Flooring - Wall to Wall Carpet, Flooring - Hardwood
BasementFull, Finished, Interior Entry
Climate & Utilities
HeatingForced Air, Oil
CoolingCentral Air, Dual
WaterPublic
SewerPublic Sewer
Building & Exterior
ConstructionFrame
RoofShingle
FoundationConcrete Perimeter
ZoningRDA
Property & Lot
Acres0.46
SqFt Lot19,998
Lot Features--
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
Third
Bedroom 5
Second
Master BedroomBedroom 2Bedroom 3Bedroom 4Bathroom 2Bathroom 3
First
Living RoomDining RoomOfficeFamily RoomBathroom 1
Main,First
Kitchen
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
Master 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
Price Drop
$2,195,000
Was $2,299,000
May 13, 2026
MLS® 73496396
Listed
$2,299,000
Apr 6, 2026
MLS® 73496396
Terminated
$2,299,000
Dec 16, 2025
MLS® 73404344
Listed
$2,299,000
Jul 14, 2025
MLS® 73404344
Terminated
$2,399,000
Jun 16, 2025
MLS® 73349101
Listed
$2,399,000
Mar 24, 2025
MLS® 73349101
Expired
$2,750,000
Dec 31, 2024
MLS® 73170437
Listed
$2,750,000
Oct 14, 2023
MLS® 73170437
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
2,667 housing units permitted in the last 12 months (-2% vs the prior 12 months) — 1,709 in 5+ unit buildings
U.S. Census Bureau, Building Permits Survey (through Jun '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 Provided By
Listing Agent: Kim Covino & Co. Team
Listing Office: Compass
MLS® Number: 73496396
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