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276 High Street, Winchester, MA 01890

Cox Road / High St Extension neighborhood · Middlesex County

Key Facts

5Beds
4Baths
5,006Sq Ft
1992Year Built
0.46Lot (acres)
3Garage

Description

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!

Property Information

Property Type

Residential

Sub-Type

Single Family Residence

Style

Colonial

Year Built

1992

Living Area

5,006 sq ft

Lot Size

0.46 acres

Garage Spaces

3

Parking Spaces

9

Zoning

RDA

Days on Market

97

MLS® Listing#

73496396

Property Features

Interior

Recessed LightingCentral VacuumOpen FloorplanCeiling Fan(s)

Exterior

Rain Gutters

Appliances

Trash CompactorWater HeaterRangeOvenDishwasherDisposalMicrowaveRefrigeratorFreezerWasherDryerPlumbed For Ice Maker

Cooling

Central AirDualZoned

Heating

Forced AirOilZoned

Flooring

TileCarpetHardwood

Fireplace

Family Room

Basement

FullFinishedInterior Entry

Parking

PavedAttachedOff StreetGarage

Laundry

Electric Dryer HookupWasher Hookup

Patio

Deck

Construction

Frame

Foundation

Concrete Perimeter

Roof

Shingle

Windows

Insulated Windows

Security

Security System

Other Structures

Gazebo

Community

Tennis Court(s)ParkGolf

Sewer

Public Sewer

Water Source

Public

Rooms

  • Bathroom 18x5First
  • Bathroom 213x12Second
  • Bathroom 39x9Second
  • Bedroom 217x14Second
  • Bedroom 315x13Second
  • Bedroom 414x12Second
  • Bedroom 524x22Third
  • Dining Room15x15First
  • Family Room30x22First
  • Kitchen16x15Main
  • Living Room15x14First
  • Master Bedroom26x23Second
  • Office14x11First

Schools

Elementary:
Vinson Owen
Middle:
Mccall
High:
Whs

Financial Details

HOA

None

Annual Taxes

$23,217

Tax year 2025

Assessed Value

$2,093,500

Parcel Number

M:025 B:0146 L:0,900972

Directions

Follow GPS. Mailbox 262 on your left. Take that turn. Go up the hill & stay right to get to 276

Affordability Calculator

$439,000

Estimated monthly payment

$11,683/mo

Principal $1,756,000 · Est. interest $2,449,776 over 30 yrs

Neighborhood Market Statistics

How this home compares to active listings in Winchester, MA

$1,000,000
Median Listing Price
39
Median Days on Market
2,513
Median Sq Ft
$536
Median Price / Sq Ft
47
Active Listings
  • This home’s price is 120% above the area median.
  • Its price per sq ft is 18% below the area median.

Market statistics compiled from active EXIT Realty® and MLS listings in Winchester, MA.

Location

Map showing the location of 276 High Street, Winchester, MA 01890

Points of Interest in Winchester, MA

Showing the Winchester area map.

Nearby Schools

  • Vinson-Owen Elementary School

    Elementary · 0.6 mi away

  • Harrington School

    Elementary · 0.9 mi away

  • Lexington Community Education

    School · 0.9 mi away

  • Peirce Elementary School

    Elementary · 1.0 mi away

  • New Covenant School

    School · 1.2 mi away

  • Stratton Elementary School

    Elementary · 1.2 mi away

  • Ambrose Elementary School

    Elementary · 1.3 mi away

  • Arlington Heights Nursery School

    Elementary · 1.4 mi away

  • Germaine Lawrence

    Secondary · 1.5 mi away

  • Reeves Elementary Pto

    Elementary · 1.5 mi away

  • The Waldorf School

    Elementary · 1.6 mi away

  • Ottoson Middle School

    Secondary · 1.6 mi away

  • Cyrus E Dallin

    Elementary · 1.8 mi away

  • Primrose School of Woburn

    School · 1.9 mi away

  • Primrose Schools

    Elementary · 1.9 mi away

  • Bishop Elementary School

    Elementary · 1.9 mi away

  • Lexington Children's Place

    School · 1.9 mi away

  • Armenian Sisters Academy

    School · 1.9 mi away

  • Lynch Elementary School

    Elementary · 2.0 mi away

  • Arlington Community Education

    School · 2.0 mi away

Commute Calculator

Travel mode

Nearby Homes

Similar Homes Nearby

Similar Home Values

Comparable nearby listings and their asking prices.

AddressPriceBedsBathsSq Ft
241 Ridge St, Winchester, MA$1,599,000442,480
117 Highland Ave, Winchester, MA$1,725,000543,722
8 Hawthorne Road, Winchester, MA$1,825,000543,315
79 Grove St, Winchester, MA$1,899,000543,210
16 & 16A Glenwood Ave, Winchester, MA$1,899,000656,900
16 Glenwood Ave, Winchester, MA$1,899,000656,900

Moving Cost Estimate

EXIT Agents in Winchester

Listing Courtesy: Compass - 7812190313

Presented by: Kim Covino & Co. Team

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non-commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein. Copyright ©2026 MLS Property Information Network, Inc. All Rights Reserved.

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Data provided by MLS Property Information Network. MLS® Listing#73496396. © 2026EXIT Realty®. All rights reserved.