Active
159 Days on market
276 High Street Winchester — Photo 1 of 36

276 High Street Winchester — Photo 1 of 36

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

Investor Analysis

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)$540/sqft
19% 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 First

15 x 14

Flooring - Hardwood, Open Floorplan, Sunken, Lighting - Overhead

Dining Room
Lvl First

15 x 15

Flooring - Hardwood, Window(s) - Picture, French Doors, Lighting - Pendant, Lighting - Overhead

Kitchen
Lvl Main,First

16 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 First

14 x 11

Closet, Flooring - Hardwood, Lighting - Overhead

Family Room
Lvl First

30 x 22

Ceiling Fan(s), Flooring - Hardwood, Balcony / Deck, Deck - Exterior, Exterior Access, Lighting - Overhead

Master Bedroom
Lvl Second

26 x 23

Bathroom - Full, Bathroom - Double Vanity/Sink, Closet - Linen, Flooring - Stone/Ceramic Tile, French Doors, Lighting - Sconce, Lighting - Overhead

Bedroom 2
Lvl Second

17 x 14

Bedroom 3
Lvl Second

15 x 13

Ceiling Fan(s), Closet, Lighting - Overhead

Bedroom 4
Lvl Second

14 x 12

Ceiling Fan(s), Closet, Lighting - Overhead

Bedroom 5
Lvl Third

24 x 22

Ceiling Fan(s), Closet, Lighting - Overhead

Bathroom 1
Lvl First

8 x 5

Bathroom - Half

Bathroom 2
Lvl Second

13 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 Second

9 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.

Full Winchester, MA market report ZIP 01890 market data
Listing Provided By

Listing Agent: Kim Covino & Co. Team

Listing Office: Compass

MLS® Number: 73496396

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