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You are here:
Home Massachusetts Winchester Homes for Sale

257 High Street Winchester, MA 01890

113 Days on Boston Pads
Price Reduced $200,000
42 Photos
$3,299,000
5 Beds
7 Baths
7101 SQFT
1.68 Acre
HOA: N/A
257 High Street
Winchester, MA 01890

Property Description

Spectacular Winchester estate offering over 7000 sf of living space with exceptional privacy and exclusivity on an oversized lot. This grand home spans over three full levels with extraordinary living spaces highlighted by a soaring two-story family room, elegant mahogany library w/ fplc, custom built-ins. The large country kitchen offers commercial grade appliances, w access to glorious deck, mudroom, pantry & oversized 2 car garage. The 2nd floor offers a stunning master w sitting area, marble bath & walk in closet. 3 add'l BR's, all generously sized. The expansive lower level features an inviting screened "Florida room" family space that opens to a bluestone patio with fire pit, overlooking expansive meticulously maintained lawn & an outdoor shower! Additionally in the LL, there is a movie theatre, full kitchen, gym, bedroom, game room w fplc, perfect for ADU/ extended family or for everyday living and entertaining. Must see this fabulous home~ The ultimate home for hosting!

Property Overview

Kitchen, Dining, and Appliances

  • Kitchen Dimensions: 20X15
  • Balcony - Exterior, Breakfast Bar / Nook, Countertops - Stone/Granite/Solid, Crown Molding, Dining Area, Exterior Access, Flooring - Hardwood, French Doors, Gas Stove, Kitchen Island, Lighting - Pendant, Open Floor Plan, Pantry, Recessed Lighting, Stainless Steel Appliances, Wainscoting, Wet bar, Window(s) - Picture, Wine Chiller
  • Dishwasher, Disposal, Dryer, Freezer, Microwave, Other (See Remarks), Range, Refrigerator, Vent Hood, Wall Oven, Washer
  • Dining Room Dimensions: 14X13
  • Dining Room Level: First Floor
  • Dining Room Features: Flooring - Hardwood

Bedrooms

  • Bedrooms: 5
  • Master Bedroom Dimensions: 31X23
  • Master Bedroom Level: Second Floor
  • Master Bedroom Features: Balcony / Deck, Bathroom - Double Vanity/Sink, Ceiling Fan(s), Closet - Walk-in, Closet/Cabinets - Custom Built, Dressing Room, Fireplace, Flooring - Hardwood, Flooring - Marble, Slider
  • Bedroom 2 Dimensions: 14X13
  • Bedroom 2 Level: Second Floor
  • Master Bedroom Features: Bathroom - Full, Ceiling Fan(s), Closet, Crown Molding, Flooring - Hardwood
  • Bedroom 3 Dimensions: 15X15
  • Bedroom 3 Level: Second Floor
  • Master Bedroom Features: Bathroom - Full, Ceiling Fan(s), Closet, Flooring - Hardwood

Other Rooms

  • Total Rooms: 16
  • Living Room Dimensions: 20X14
  • Living Room Level: First Floor
  • Living Room Features: Flooring - Hardwood, French Doors
  • Family Room Dimensions: 26X16
  • Family Room Level: First Floor
  • Family Room Features: Ceiling - Vaulted, Fireplace, Flooring - Hardwood
  • Laundry Room Features: Finished, Full, Interior Access, Walk Out

Bathrooms

  • Full Baths: 5
  • Half Baths 2
  • Master Bath: 1
  • Bathroom 1 Dimensions: 8X5
  • Bathroom 1 Level: First Floor
  • Bathroom 1 Features: Bathroom - Half, Flooring - Stone/Ceramic Tile
  • Bathroom 2 Dimensions: 10X7
  • Bathroom 2 Level: First Floor
  • Bathroom 2 Features: Bathroom - Half, Flooring - Stone/Ceramic Tile
  • Bathroom 3 Dimensions: 16X12
  • Bathroom 3 Level: Second Floor
  • Bathroom 3 Features: Bathroom - Double Vanity/Sink, Bathroom - Full, Bathroom - With Shower Stall, Closet - Walk-in, Closet/Cabinets - Custom Built, Countertops - Stone/Granite/Solid, Flooring - Hardwood, Jacuzzi / Whirlpool Soaking Tub, Recessed Lighting

Amenities

  • Public School
  • Walk/Jog Trails

Utilities

  • Heating: Forced Air, Gas
  • Heat Zones: 3
  • Hot Water: Natural Gas
  • Cooling: Central Air
  • Cooling Zones: 3
  • Electric Info: 200 Amps
  • Energy Features: Insulated Doors, Insulated Windows
  • Utility Connections: for Electric Dryer, for Electric Oven, for Electric Range, for Gas Oven, for Gas Range
  • Water: City/Town Water
  • Sewer: City/Town Sewer

Garage & Parking

  • Garage Parking: Attached
  • Garage Spaces: 2
  • Parking Features: Paved Driveway
  • Parking Spaces: 9

Interior Features

  • Square Feet: 7101
  • Fireplaces: 4
  • Interior Features: Central Vacuum, Sauna/Steam/Hot Tub, Security System
  • Accessability Features: Unknown

Construction

  • Year Built: 1994
  • Type: Detached
  • Style: Colonial, Contemporary
  • Construction Type: Frame
  • Foundation Info: Poured Concrete
  • Roof Material: Asphalt/Fiberglass Shingles
  • Flooring Type: Hardwood, Marble, Tile
  • Lead Paint: Unknown
  • Warranty: No

Exterior & Lot

  • Lot Description: Wooded
  • Exterior Features: Balcony, Deck, Gutters, Patio, Patio - Enclosed, Porch, Porch - Enclosed, Sprinkler System
  • Road Type: Paved, Public, Publicly Maint.

Other Information

  • MLS ID# 73426449
  • Last Updated: 12/07/25
  • HOA: No
  • Reqd Own Association: Unknown

Date Event Price Price/Sq Ft Source
10/18/2025Active$3,299,000$465MLSPIN
10/14/2025Price Change$3,299,000$465MLSPIN
09/08/2025Active$3,499,000$493MLSPIN
09/04/2025New$3,499,000$493MLSPIN

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Map & Resources

Vinson-Owen Elementary School

Public Elementary School, Grades: PK-5

0.46mi

West Side Fire Station

Fire Station

0.3mi

Winchester Swim and Tennis Club

Swimming Pool. Sports: Tennis

0.23mi

Locke Farm Conservation Area

Municipal Park

0.08mi

Smith Pond Conservation Area

Municipal Park

0.14mi

Whipple Hill Conservation Land

Municipal Park

0.14mi

Sachem Swamp

Municipal Park

0.44mi

Addition To Sachem Swamp

Municipal Park

0.46mi

Mullen Park

Municipal Park

0.32mi

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#: 73426449

© 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 2025-12-07 17:39:00

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