257 High Street, Winchester, MA 01890

Local realty services provided by:Better Homes and Gardens Real Estate The Shanahan Group
257 High Street,Winchester, MA 01890
$3,299,000
  • 5 Beds
  • 7 Baths
  • 7,101 sq. ft.
  • Single family
  • Active
Listed by:kim covino & co. team
Office:compass
MLS#:73426449
Source:MLSPIN

Price summary

  • Price:$3,299,000
  • Price per sq. ft.:$464.58

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!

Contact an agent

contact an agent

Yes, I would like more information from BHGRE®. Please use and/or share my information with an BHGRE affiliated agent to contact me about my real estate needs. By clicking Send message, I agree an BHGRE affiliated agent may contact me by phone or text message including by automated means about real estate services, and that I can access real estate services without providing my phone number. I acknowledge that I have read and agree to theTerms of useandPrivacy notice

Home facts

  • Year built:1994
  • Listing ID #:73426449
  • Updated:October 19, 2025 at 01:52 AM

Rooms and interior

  • Bedrooms:5
  • Total bathrooms:7
  • Full bathrooms:5
  • Half bathrooms:2
  • Living area:7,101 sq. ft.

Heating and cooling

  • Cooling:3 Cooling Zones, Central Air
  • Heating:Fireplace, Forced Air, Natural Gas

Structure and exterior

  • Roof:Shingle
  • Year built:1994
  • Building area:7,101 sq. ft.
  • Lot area:1.68 Acres

Schools

  • High school:Winchester High
  • Middle school:Mccall Middle
  • Elementary school:Vinson Owen

Utilities

  • Water:Public
  • Sewer:Public Sewer

Finances and disclosures

  • Price:$3,299,000
  • Price per sq. ft.:$464.58
  • Tax amount:$26,758 (2025)
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.

New listings near 257 High Street