257 High St Winchester, MA 01890
West Side NeighborhoodEstimated payment $19,584/month
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!
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
- Open Parking
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
Map
Home Values in the Area
Average Home Value in this Area
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 |
Property History
| Date | Event | Price | List to Sale | Price per Sq Ft |
|---|---|---|---|---|
| 10/14/2025 10/14/25 | Price Changed | $3,299,000 | -5.7% | $465 / Sq Ft |
| 09/04/2025 09/04/25 | For Sale | $3,499,000 | -- | $493 / Sq Ft |
Purchase History
| Date | Type | Sale Price | Title Company |
|---|---|---|---|
| Quit Claim Deed | -- | None Available | |
| Deed | -- | -- | |
| Deed | $600,300 | -- | |
| Deed | $600,300 | -- |
Mortgage History
| Date | Status | Loan Amount | Loan Type |
|---|---|---|---|
| Previous Owner | $900,000 | Purchase Money Mortgage | |
| Previous Owner | $425,000 | Purchase Money Mortgage |
Source: MLS Property Information Network (MLS PIN)
MLS Number: 73426449
APN: WINC-000027-000342
Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.
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.
- 30 Whipple Rd
- 31 Coolidge Rd
- 24 Tyler Rd
- 127 Lowell St
- 129 Madison Ave Unit 2
- 46 Lowell St Unit 2
- 8 Grace Rd
- 322 Lowell St
- 195 Forest St Unit 195
- 135 Maple St
- 14 Park Place Unit 16
- 12 Park Place Unit 12
- 32 Waltham St
- 10 Carson Rd
- 35 Rindge Ave Unit B
- 29 Wainwright Rd
- 17 Rockaway Ln
- 19 Newland Rd Unit 2
- 104 Forest St Unit 104
- 104 Forest St