5,006 Sq. Ft.
$459 / Sq. Ft.
5,006
Sq. Ft.
$459
per Sq. Ft.

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...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!

Listing Agents

  1. Kim Covino

    Kim Covino

    Alternative Listing Agent

    Compass

    kim.covino@compass.com

    P: (781)-249-3854

Property Details for 276 High Street

Town
Winchester
Area
MA-Winchester
Architectural Style
Colonial
Style
Colonial
Garage Spaces
3
Open Parking Spaces
6.00
Parking Spaces Total
9

Open Houses

Sunday, Apr 26th1:00 PM - 2:30 PM
LISTING UPDATED: 04/10/2026 03:07 AM

Property Details for 276 High Street

StatusActive
MLS #73496396
Days on Market18
Taxes$23,217 / year
HOA Fees-
Property TypeSingle Family
MLS TypeSingle Family / Detached
Year Built1992
CountyMiddlesex County
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Building Information for 276 High Street

Stories-Year Built1992Building Size-Lot Size0.46 AC / 19,998 SF

Payment Calculator

$13,511 per month

30 year fixed, 6.46% Interest

Principal and Interest

$11,577

Property Taxes

$1,935

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 276 High Street

General Details
Property Details
  • Building Area Units: Square Feet
  • Community Features: Public Transportation, Shopping, Tennis Court, Park, Golf Course, Bike Path, Highway Access, Public School
  • Living Area: 5006.0
  • Color: Green
  • SqFt with Basement: Yes
  • Property Attached: No
  • Single Family Type: Detached
  • Waterfront: No
  • Year Built Details: Actual
  • Year Built Source: Public Records
Location/School
  • Grade School: Vinson Owen
  • High School: Whs
  • Middle School: Mccall
  • Neighborhood: Cox Road / High St Extension neighborhood
Features
Interior Features
  • Appliances: Water Heater, Range, Oven, Dishwasher, Disposal, Trash Compactor, Microwave, Refrigerator, Freezer, Washer, Dryer, Plumbed For Ice Maker
  • Basement Features: Full, Finished, Interior Access
  • Num of Baths: 4.0
  • Num of Full Baths: 3
  • Num of Half Baths: 1
  • Bathrooms Total Decimal: 3.50
  • Bathrooms Total Integer: 4
  • DoorFeatures: Insulated Doors
  • FireplaceFeatures: Family Room
  • FireplaceYN: Yes
  • Fireplaces: 1
  • Flooring: Tile, Carpet, Hardwood, Flooring - Wall to Wall Carpet, Flooring - Hardwood
  • Interior Features: Bathroom - Tiled With Shower Stall, Bathroom - Full, Bathroom - With Shower Stall, Recessed Lighting, Closet, Lighting - Overhead, Bathroom, Game Room, Office, Central Vacuum, Walk-up Attic
  • Interior Features: Central Vacuum, Security System
  • Laundry Features: Second Floor, Electric Dryer Hookup, Washer Hookup
  • Primary Bath: Yes
  • SpaYN: No
  • Window Features: Insulated Windows
Exterior Features
  • Construction: Frame
  • Exterior Features: Deck, Rain Gutters, Sprinkler System, Gazebo
  • Exterior Features: Gazebo, Sprinkler System, Deck
  • Other Structures: Gazebo
  • Patio And Porch Features: Deck
  • Roof Material: Shingle
Parking Features
  • Attached Garage: Yes
  • Carport: No
  • Covered Spaces: 3.00
  • Garage: Yes
  • Garage Parking: Attached, Paved Drive, Off-Street
  • Open Parking: Yes
  • Parking Features: Attached, Paved Drive, Off-Street
  • Parking Features: Off-Street
Utilities
  • Cooling: Central Air, 2 Units
  • Cooling: Yes
  • Electric: 200+ Amp Service
  • Green Energy Efficient: Thermostat
  • Heating: Forced Air, Oil
  • Heating: Yes
  • Sewer: City/Town Sewer
  • Utility Connections: for Electric Range, for Electric Oven, for Electric Dryer, Washer Hookup, Icemaker Connection
  • Water: Public
Room Information
Primary Bedroom
  • Room Primary Bedroom Area: 598.0
  • Room Primary Bedroom Features: Bathroom - Full,Bathroom - Double Vanity/Sink,Closet - Linen,Flooring - Stone/Ceramic Tile,French Doors,Lighting - Sconce,Lighting - Overhead
  • Room Primary Bedroom Length: 26.0
  • Primary Bedroom Level: Second Floor
  • Room Primary Bedroom Width: 23.0
Bedroom 2
  • Bedroom2 Area: 238.0
  • Bedroom2 Features: Ceiling Fan(s),Closet,Lighting - Overhead
  • Bedroom2 Length: 17.0
  • Bedroom2 Level: Second
  • Bedroom2 Width: 14.0
Bedroom 3
  • Bedroom3 Area: 195.0
  • Bedroom3 Features: Ceiling Fan(s),Closet,Lighting - Overhead
  • Bedroom3 Length: 15.0
  • Bedroom3 Level: Second
  • Bedroom3 Width: 13.0
Bedroom 4
  • Bedroom4 Area: 168.0
  • Bedroom4 Features: Ceiling Fan(s),Closet,Lighting - Overhead
  • Bedroom4 Length: 14.0
  • Bedroom4 Level: Second
  • Bedroom4 Width: 12.0
Bedroom 5
  • Bedroom5 Area: 528.0
  • Bedroom5 Features: Ceiling Fan(s),Closet,Lighting - Overhead
  • Bedroom5 Length: 24.0
  • Bedroom5 Level: Third
  • Bedroom5 Width: 22.0
Bathroom 1
  • Bathroom1 Area: 40.0
  • Bathroom1 Features: Bathroom - Half
  • Bathroom1 Length: 8.0
  • Bathroom1 Level: First
  • Bathroom1 Width: 5.0
Bathroom 2
  • Bathroom2 Area: 156.0
  • Bathroom2 Features: Bathroom - Full,Bathroom - Double Vanity/Sink,Bathroom - Tiled With Shower Stall,Bathroom - Tiled With Tub,Closet,Flooring - Stone/Ceramic Tile,Jacuzzi / Whirlpool Soaking Tub
  • Bathroom2 Length: 13.0
  • Bathroom2 Level: Second
  • Bathroom2 Width: 12.0
Bathroom 3
  • Bathroom3 Area: 81.0
  • Bathroom3 Features: Bathroom - Full,Bathroom - Double Vanity/Sink,Bathroom - Tiled With Tub & Shower
  • Bathroom3 Length: 9.0
  • Bathroom3 Level: Second
  • Bathroom3 Width: 9.0
Dining Room
  • Dining Room Area: 225.0
  • Dining Room Features: Flooring - Hardwood,Window(s) - Picture,French Doors,Lighting - Pendant,Lighting - Overhead
  • Dining Room Length: 15.0
  • Dining Room Level: First
  • Dining Room Width: 15.0
Family Room
  • Family Room Area: 660.0
  • Family Room Features: Ceiling Fan(s),Flooring - Hardwood,Balcony / Deck,Deck - Exterior,Exterior Access,Lighting - Overhead
  • Family Room Length: 30.0
  • Family Room Level: First
  • Family Room Width: 22.0
Kitchen
  • Kitchen Area: 240.0
  • Kitchen Features: 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
  • Kitchen Length: 16.0
  • Kitchen Level: Main,First
  • Kitchen Width: 15.0
Laundry
  • Laundry Dimen: 7X3
Living Room
  • Room Living Room Area: 210.0
  • Room Living Room Features: Flooring - Hardwood,Open Floorplan,Sunken,Lighting - Overhead
  • Room Living Room Length: 15.0
  • Room Living Room Level: First
  • Room Living Room Width: 14.0
Other Room 1
  • Room Office Area: 154.0
  • Room Office Features: Closet,Flooring - Hardwood,Lighting - Overhead
  • Room Office Length: 14.0
  • Room Office Level: First
  • Room Office Width: 11.0
Property Information
Property Info
  • Farm Land Area Units: Square Feet
  • WARRANTY: No
  • Lot Size Units: Acres
  • Disclosures: Common driveway entry then splits off
Tax Information
  • Tax ID: M:025 B:0146 L:0,900972
  • Assessments: $2,093,500
  • Book: 0
  • Tax Year: 2025
  • Zoning: RDA
Building / Association Information
Living Characteristics
  • Beds Total: 5
Other Building Characteristics
  • Foundation: Concrete Perimeter
  • Cooling Zones: 2
  • Heat Zones: 6
Complex & Association Information
  • Association Security: Security System
  • Adult Community: No

Property History for 276 High Street

DateEvent & SourcePriceAppreciation
Apr 6, 2026

Listed (Active)

MLS PIN #73496396

$2,299,000—
Dec 16, 2025

Canceled

MLS PIN #73404344

$2,299,000—
Jul 14, 2025

Listed (Active)

MLS PIN #73404344

$2,350,000—
DateEvent & SourcePrice
04/06/2026

Listed (Active)

MLS PIN #73496396

$2,299,000
12/16/2025

Canceled

MLS PIN #73404344

$2,299,000
07/14/2025

Listed (Active)

MLS PIN #73404344

$2,350,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 276 High Street

Taxable ValueLand$889,200Additions$1,204,300Total$2,093,500
Tax Record2025$23,217 ($1,935 / month)
Home Facts
Beds4Baths3.5Total Finished SqFt3,788 SqFtAbove Grade Finished SqFt3,788 SqFtUnfinished Basement SqFt1,944 SqFtStories3Lot Size19,998 SqFtStyleSingle Family ResidenceYear Built1992ZoningRDACountyMIDDLESEXAPNWINC M:025 B:0146 L:0Fireplace TypeHas Fireplace

Schools near 276 High Street

This home is within Winchester School District.
Rating
School
Type
Grades
Distance
Public - PK to 5
Public - 6 to 8
Public - 9 to 12
Private - 6 to 12
Rating
School
Distance
Vinson-Owen Elementary School
PublicPK to 5

McCall Middle School
Public6 to 8

Winchester High School
Public9 to 12

Lexington Christian Academy
Private6 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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276 High Street is a single family home for sale in Winchester, MA 01890. This property was listed for sale on April 6, 2026 by Compass, it's currently listed at $2,299,000. It has been on the market for a total of 18 days and was last sold on February 16, 2000. This listing's school district is Winchester School District. Nearby schools include Vinson-Owen Elementary School, McCall Middle School and Winchester High School. 276 High Street is a 5-bed, 4-bath, 5,006 sqft single family home built in 1992.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.

The property listing data and information, or the images, set forth herein were provided to MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS. 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 or leasing 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 or leasing. MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS 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.