$3,250,000
OPEN SAT 1PM - 2:30PM

257 High St Winchester, MA 01890

West Side Neighborhood

Estimated payment $19,580/month

Total Views 128
5 Beds
7 Baths
7,101 Sq Ft
$458 Price per Sq Ft

Highlights

  • Media Room
  • Sauna
  • Open Floorplan
  • Vinson-Owen Elementary School Rated A+
  • 1.68 Acre Lot
  • Custom Closet System

About This Home

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!

Listing Agent

Kim Covino

Compass Listed on: 04/09/2026

Compass

Open House Schedule

Home Details

Home Type

  • Single Family

Est. Annual Taxes

  • $26,758

Year Built

  • Built in 1994

Lot Details

  • 1.68 Acre Lot
  • Sprinkler System
  • Wooded Lot

Parking

  • 2 Car Attached Garage
  • Driveway
  • 7 Open Parking Spaces

Home Design

  • Colonial Architecture
  • Contemporary Architecture
  • Frame Construction
  • Shingle Roof
  • Concrete Perimeter Foundation

Interior Spaces

  • 7,101 Sq Ft Home
  • Open Floorplan
  • Wet Bar
  • Central Vacuum
  • Crown Molding
  • Wainscoting
  • Tray Ceiling
  • Vaulted Ceiling
  • Ceiling Fan
  • Recessed Lighting
  • Decorative Lighting
  • Insulated Windows
  • Picture Window
  • French Doors
  • Sliding Doors
  • Insulated Doors
  • Mud Room
  • Family Room with Fireplace
  • 4 Fireplaces
  • Combination Dining and Living Room
  • Media Room
  • Home Office
  • Utility Room with Study Area
  • Sauna
  • Home Security System

Kitchen

  • Breakfast Bar
  • Oven
  • Stove
  • Range with Range Hood
  • Microwave
  • Freezer
  • Dishwasher
  • Wine Cooler
  • Stainless Steel Appliances
  • Kitchen Island
  • Solid Surface Countertops
  • Disposal

Flooring

  • Wood
  • Wall to Wall Carpet
  • Marble
  • Ceramic Tile

Bedrooms and Bathrooms

  • 5 Bedrooms
  • Fireplace in Primary Bedroom
  • Primary bedroom located on second floor
  • Custom Closet System
  • Walk-In Closet
  • Dressing Area
  • Dual Vanity Sinks in Primary Bathroom
  • Soaking Tub
  • Separate Shower

Laundry

  • Laundry on main level
  • Dryer
  • Washer

Finished Basement

  • Walk-Out Basement
  • Basement Fills Entire Space Under The House
  • Interior Basement Entry

Outdoor Features

  • Balcony
  • Deck
  • Enclosed Patio or Porch
  • Rain Gutters

Location

  • Property is near schools

Schools

  • Vinson Owen Elementary School
  • Mccall Middle School
  • Winchester High School

Utilities

  • Forced Air Heating and Cooling System
  • 3 Cooling Zones
  • 3 Heating Zones
  • Heating System Uses Natural Gas
  • 200+ Amp Service
  • Gas Water Heater

Listing and Financial Details

  • Assessor Parcel Number M:027 B:0342 L:0,901606

Community Details

Overview

  • No Home Owners Association
  • West Side Subdivision

Recreation

  • Jogging Path

Home Details

Home Type

Single Family

Est. Annual Taxes

$26,758

Year Built

Built in 1994

Lot Details

1.68 Acres

Parking

2

Listing Details

  • Property Type: Residential
  • Property Sub Type: Single Family Residence
  • Architectural Style: Colonial, Contemporary
  • Year Built: 1994
  • Subdivision Name: West Side
  • Year Built Details: Actual,Renovated Since
  • Year Round: Yes
  • Special Features: 4097

Interior Features

  • Flooring: Tile, Marble, Hardwood, Flooring - Hardwood, Flooring - Stone/Ceramic Tile, Flooring - Wall to Wall Carpet
  • Interior Amenities: Breakfast Bar / Nook, Closet, Closet/Cabinets - Custom Built, Ceiling Fan(s), Dining Area, Countertops - Stone/Granite/Solid, Recessed Lighting, Slider, Study, Home Office, Kitchen, Living/Dining Rm Combo, Media Room, Central Vacuum, Sauna/Steam/Hot Tub, Wet Bar
  • Door Features: Insulated Doors
  • Fireplace Features: Family Room, Master Bedroom
  • Fireplace YN: Yes
  • Fireplaces: 4
  • Appliances: Gas Water Heater, Range, Oven, Dishwasher, Disposal, Microwave, Refrigerator, Freezer, Washer, Dryer, Range Hood, Other
  • Total Bedrooms: 5
  • Room Bedroom2 Level: Second
  • Room Bedroom2 Features: Bathroom - Full, Ceiling Fan(s), Closet, Flooring - Hardwood, Crown Molding
  • Room Bedroom3 Features: Bathroom - Full, Ceiling Fan(s), Closet, Flooring - Hardwood
  • Room Bedroom3 Level: Second
  • Room Bedroom4 Level: Second
  • Room Bedroom4 Features: Ceiling Fan(s), Closet, Flooring - Hardwood, Recessed Lighting
  • Room Bedroom5 Level: Basement
  • Room Bedroom5 Features: Bathroom - Full
  • Basement YN: Yes
  • Full Bathrooms: 5
  • Half Bathrooms: 2
  • Total Bathrooms: 7
  • Room Master Bedroom Features: Bathroom - Double Vanity/Sink, Ceiling Fan(s), Walk-In Closet(s), Closet/Cabinets - Custom Built, Flooring - Hardwood, Flooring - Marble, Balcony / Deck, Dressing Room, Slider, Tray Ceiling(s)
  • Room Master Bedroom Level: Second
  • Master Bathroom Features: Yes
  • Bathroom 1 Features: Bathroom - Half, Flooring - Stone/Ceramic Tile
  • Bathroom 1 Level: First
  • Bathroom 2 Level: First
  • Bathroom 2 Features: Bathroom - Half, Flooring - Stone/Ceramic Tile
  • Bathroom 3 Features: Bathroom - Full, Bathroom - Double Vanity/Sink, Bathroom - With Shower Stall, Walk-In Closet(s), Closet/Cabinets - Custom Built, Flooring - Hardwood, Countertops - Stone/Granite/Solid, Jacuzzi / Whirlpool Soaking Tub, Recessed Lighting
  • Bathroom 3 Level: Second
  • Room Dining Room Features: Flooring - Hardwood
  • Room Dining Room Level: First
  • Room Family Room Level: First
  • Room Family Room Features: Vaulted Ceiling(s), Flooring - Hardwood
  • Room Kitchen Level: Main,First
  • Room Kitchen Features: Flooring - Hardwood, Window(s) - Picture, Dining Area, Balcony - Exterior, Pantry, Countertops - Stone/Granite/Solid, French Doors, Kitchen Island, Wet Bar, Breakfast Bar / Nook, Exterior Access, Open Floorplan, Recessed Lighting, Stainless Steel Appliances, Wainscoting, Wine Chiller, Gas Stove, Lighting - Pendant, Crown Molding
  • Laundry Features: Flooring - Stone/Ceramic Tile, First Floor, Electric Dryer Hookup
  • Room Living Room Level: First
  • Room Living Room Features: Flooring - Hardwood, French Doors
  • Room Office Level: Second
  • Room Office Features: Closet/Cabinets - Custom Built
  • Basement: Full, Finished, Walk-Out Access, Interior Entry
  • Above Grade Finished Sq Ft: 7101
  • Living Area: 7101
  • Spa YN: No
  • Window Features: Insulated Windows
  • MAIN LO: AN2383
  • Insulation: Full

Exterior Features

  • Exterior Features: Porch, Porch - Enclosed, Deck, Patio, Patio - Enclosed, Balcony, Rain Gutters, Sprinkler System
  • Construction Materials: Frame
  • Foundation Details: Concrete Perimeter
  • Home Warranty YN: No
  • Patio And Porch Features: Porch, Porch - Enclosed, Deck, Patio, Enclosed
  • Road Frontage Type: Public
  • Road Surface Type: Paved
  • Roof: Shingle
  • Waterfront YN: No
  • Waterview Flag: No

Garage/Parking

  • Garage Spaces: 2
  • Attached Garage YN: Yes
  • Carport Y N: No
  • Covered Parking Spaces: 2
  • Garage YN: Yes
  • Open Parking Spaces: 7
  • Open Parking YN: Yes
  • Parking Features: Attached, Paved Drive, Paved
  • Total Parking Spaces: 9

Utilities

  • Sewer: Public Sewer
  • Utilities: for Gas Range, for Electric Range, for Gas Oven, for Electric Oven, for Electric Dryer
  • Cooling: Central Air
  • Heating: Forced Air, Natural Gas, Fireplace
  • Cooling Y N: Yes
  • Electric: 200+ Amp Service
  • Heating YN: Yes
  • Security Features: Security System
  • Water Source: Public
  • HEAT ZONES: 3
  • COOLING ZONES: 3

Condo/Co-op/Association

  • Association YN: No
  • Community Features: Walk/Jog Trails, Public School
  • Senior Community YN: No

Lot Info

  • Parcel Number: M:027 B:0342 L:0,901606
  • Zoning: res
  • Farm Land Area Units: Square Feet
  • Lot Features: Wooded
  • Lot Size Acres: 1.68
  • Lot Size Sq Ft: 73015
  • Lot Size Units: Acres
  • Property Attached YN: No

Tax Info

  • Tax Year: 2025
  • Tax Annual Amount: 26758

Multi Family

  • Basement Included Sq Ft: No

MLS Schools

  • High School: Winchester High
  • Elementary School: Vinson Owen
  • Middle Or Junior School: Mccall Middle

Map

Range of Values:

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Value Increase
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Percent Increase
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Adjusted for Inflation
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Home Values in the Area

Source: Public Records

Average Home Value in this Area

Source: Public Records

Tax History

Year Tax Paid Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. Land Improvement
2025 $26,758 $2,412,800 $1,073,500 $1,339,300
2024 $25,689 $2,267,300 $1,033,500 $1,233,800
2023 $25,097 $2,126,900 $913,500 $1,213,400
2022 $22,697 $1,814,300 $790,400 $1,023,900
2021 $21,994 $1,714,300 $690,400 $1,023,900
2020 $21,240 $1,714,300 $690,400 $1,023,900
2019 $20,760 $1,714,300 $690,400 $1,023,900
2018 $20,268 $1,662,700 $668,400 $994,300
2017 $19,118 $1,556,800 $608,400 $948,400
2016 $17,832 $1,526,700 $608,400 $918,300
2015 $17,452 $1,437,600 $555,400 $882,200
2014 $17,491 $1,381,600 $515,400 $866,200
Source: Public Records

Property History

Date Event Price List to Sale Price per Sq Ft
04/09/2026 04/09/26 For Sale $3,250,000 -- $458 / Sq Ft
Source: MLS Property Information Network (MLS PIN)

Purchase History

Date Type Sale Price Title Company
Quit Claim Deed -- None Available
Deed -- --
Deed $600,300 --
Deed $600,300 --
Source: Public Records

Mortgage History

Date Status Loan Amount Loan Type
Previous Owner $900,000 Purchase Money Mortgage
Previous Owner $425,000 Purchase Money Mortgage
Source: Public Records

Source: MLS Property Information Network (MLS PIN)

MLS Number: 73499287

MLS Property Information Network (MLS PIN)

APN: WINC-000027-000342

Massachusetts Middlesex County Winchester 01890 West Side

257 High St, Winchester, MA

For Sale

Detached

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MLS Property Information Network (MLS PIN) 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 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 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, or as to the accuracy of any of the Images, set forth herein.

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Kim Covino
Listing Agent
Kim Covino
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Compass
(781) 785-8771
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