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You are here:
Home Massachusetts Winchester Homes for Sale

276 High Street Winchester, MA 01890

144 Days on Boston Pads
Price Reduced $51,000
38 Photos
$2,299,000
5 Beds
4 Baths
5006 SQFT
0.46 Acre
HOA: N/A
276 High Street
Winchester, MA 01890

Property 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 Overview

Kitchen, Dining, and Appliances

  • Kitchen Dimensions: 16X15
  • Breakfast Bar / Nook, Closet/Cabinets - Custom Built, Countertops - Stone/Granite/Solid, Exterior Access, Flooring - Stone/Ceramic Tile, French Doors, Kitchen Island, Lighting - Pendant, Open Floor Plan, Recessed Lighting, Stainless Steel Appliances
  • Dishwasher, Disposal, Dryer, Freezer, Microwave, Range, Refrigerator, Wall Oven, Washer
  • Dining Room Dimensions: 15X15
  • Dining Room Level: First Floor
  • Dining Room Features: Flooring - Hardwood, French Doors, Lighting - Overhead, Lighting - Pendant, Window(s) - Picture

Bedrooms

  • Bedrooms: 5
  • Master Bedroom Dimensions: 26X23
  • Master Bedroom Level: Second Floor
  • Master Bedroom Features: Bathroom - Double Vanity/Sink, Bathroom - Full, Closet - Linen, Flooring - Stone/Ceramic Tile, French Doors, Lighting - Overhead, Lighting - Sconce
  • Bedroom 2 Dimensions: 17X14
  • Bedroom 2 Level: Second Floor
  • Master Bedroom Features: Ceiling Fan(s), Closet, Lighting - Overhead
  • Bedroom 3 Dimensions: 15X13
  • Bedroom 3 Level: Second Floor
  • Master Bedroom Features: Ceiling Fan(s), Closet, Lighting - Overhead

Other Rooms

  • Total Rooms: 11
  • Living Room Dimensions: 15X14
  • Living Room Level: First Floor
  • Living Room Features: Flooring - Hardwood, Lighting - Overhead, Open Floor Plan, Sunken
  • Family Room Dimensions: 30X22
  • Family Room Level: First Floor
  • Family Room Features: Balcony / Deck, Ceiling Fan(s), Deck - Exterior, Exterior Access, Fireplace, Flooring - Hardwood, Lighting - Overhead
  • Laundry Room Features: Finished, Full, Interior Access

Bathrooms

  • Full Baths: 3
  • Half Baths 1
  • Master Bath: 1
  • Bathroom 1 Dimensions: 8X5
  • Bathroom 1 Level: First Floor
  • Bathroom 1 Features: Bathroom - Half
  • Bathroom 2 Dimensions: 13X12
  • Bathroom 2 Level: Second Floor
  • Bathroom 2 Features: Bathroom - Double Vanity/Sink, Bathroom - Full, Bathroom - Tiled With Shower Stall, Bathroom - Tiled With Tub, Closet, Flooring - Stone/Ceramic Tile, Jacuzzi / Whirlpool Soaking Tub
  • Bathroom 3 Dimensions: 9X9
  • Bathroom 3 Level: Second Floor
  • Bathroom 3 Features: Bathroom - Double Vanity/Sink, Bathroom - Full, Bathroom - Tiled With Tub & Shower

Amenities

  • Bike Path
  • Golf Course
  • Highway Access
  • Park
  • Public School
  • Public Transportation
  • Shopping
  • Tennis Court

Utilities

  • Heating: Forced Air, Oil
  • Heat Zones: 6
  • Hot Water: Other (See Remarks)
  • Cooling: 2 Units, Central Air
  • Cooling Zones: 2
  • Electric Info: 200 Amps
  • Energy Features: Insulated Doors, Insulated Windows, Prog. Thermostat
  • Utility Connections: Icemaker Connection, Washer Hookup, for Electric Dryer, for Electric Oven, for Electric Range
  • Water: City/Town Water
  • Sewer: City/Town Sewer

Garage & Parking

  • Garage Parking: Attached
  • Garage Spaces: 3
  • Parking Features: Off-Street
  • Parking Spaces: 6

Interior Features

  • Square Feet: 5006
  • Fireplaces: 1
  • Interior Features: Central Vacuum, Security System
  • Accessability Features: Unknown

Construction

  • Year Built: 1992
  • Type: Detached
  • Style: Colonial
  • Construction Type: Frame
  • Foundation Info: Poured Concrete
  • Roof Material: Asphalt/Fiberglass Shingles
  • Flooring Type: Hardwood, Tile, Wall to Wall Carpet
  • Lead Paint: None
  • Warranty: No

Exterior & Lot

  • Exterior Features: Deck, Gazebo, Gutters, Sprinkler System

Other Information

  • MLS ID# 73404344
  • Last Updated: 09/29/25
  • HOA: No
  • Reqd Own Association: Unknown

Date Event Price Price/Sq Ft Source
09/29/2025Active$2,299,000$459MLSPIN
09/25/2025Price Change$2,299,000$459MLSPIN
07/18/2025Active$2,350,000$469MLSPIN
07/14/2025New$2,350,000$469MLSPIN
06/16/2025Canceled$2,399,000$473MLSPIN
04/08/2025Active$2,399,000$473MLSPIN
04/04/2025Price Change$2,399,000$473MLSPIN
03/28/2025Active$2,599,000$512MLSPIN
03/24/2025New$2,599,000$512MLSPIN
01/01/2025Expired$2,750,000$417MLSPIN
09/15/2024Temporarily Withdrawn$2,750,000$417MLSPIN
07/09/2024Active$2,750,000$417MLSPIN
07/05/2024Price Change$2,750,000$417MLSPIN
04/29/2024Active$2,870,000$435MLSPIN
04/25/2024Price Change$2,870,000$435MLSPIN
04/16/2024Active$2,830,000$429MLSPIN
04/12/2024Price Change$2,830,000$429MLSPIN
02/01/2024Active$2,930,000$444MLSPIN
01/28/2024Back on Market$2,930,000$444MLSPIN
11/29/2023Temporarily Withdrawn$2,590,000$393MLSPIN
10/18/2023Active$2,590,000$393MLSPIN
10/14/2023New$2,590,000$393MLSPIN

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Map & Resources

West Side Fire Station

Fire Station

0.39mi

Winchester Swim and Tennis Club

Swimming Pool. Sports: Tennis

0.32mi

Whipple Hill Conservation Land

Municipal Park

0.03mi

Locke Farm Conservation Area

Municipal Park

0.07mi

Smith Pond Conservation Area

Municipal Park

0.25mi

Lots 351-354

Municipal Park

0.45mi

Mullen Park

Municipal Park

0.41mi

Real Estate Resources

BayCoast Mortgage As a full-service lender providing industry-best solutions, BayCoast Mortgage can help make homeownership a reality for you. Want to get preapproved? Start today!
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Seller's Representative: Kim Covino & Co. Team, Compass
MLS ID#: 73404344

© 2025 MLS Property Information Network, Inc.. All rights reserved.

The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information 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. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein.

MLS PIN data last updated at 2025-09-29 03:05:00

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