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Ayden Hardy
REALTOR®
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257 High Street, Winchester, MA 01890

$3,250,000
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Active Under Contract
BEDS5 BATHS5 full 2 partial SQUARE FEET7,101 MLS#73499287
STATUSActive Under Contract PROPERTY TYPEResidential - Single Family SUBDIVISIONWest Side

Property Description

OPEN HOUSE CANCELLED 4/12 **OFFER ACCEPTED** 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 everyday living & entertaining. Must see this fabulous home~

257 High Street | MLS# 73499287

This single family home located at 257 High Street, Winchester, MA 01890 is currently listed for sale with an asking price of $3,250,000. This property was built in 1994 and has 5 bedrooms and 5 full and 2 partial baths with 7101 sq. ft. High Street is located in the West Side subdivision. Search West Side real estate on aydenhardy.masiellogrouprealestate.com today.

Property Features

Property Type: Residential - Single Family
Basement: Full, Finished, Walk-Out Access, Interior Entry
Basement: Yes
Cooling: Central Air
Fireplaces: 4
Garage: 2 car attached
Heating: Forced Air, Natural Gas, Fireplace
Home Style: Colonial, Contemporary
Lot Size: 1.68 Acres
Roof Type: Shingle
Taxes: $26,758
Year Built: 1994

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
Porch
Porch - Enclosed
Deck
Patio
Patio - Enclosed
Balcony
Rain Gutters
Sprinkler System

Feature Descriptions

Appliances: Gas Water Heater, Range, Oven, Dishwasher, Disposal, Microwave, Refrigerator, Freezer, Washer, Dryer, Range Hood, Other
Building Area Total: 7101
Community Features: Walk/Jog Trails, Public School
Compensation Based On: N/A
Compensation Broker Transaction: N/A
Compensation Buyer Agency: N/A
Compensation Sub Agency: N/A
Compensation Sub Agency Offered: N/A
Days on Site: 8
Dining Room: Flooring - Hardwood
Door Features: Insulated Doors
Electric: 200+ Amp Service
Exterior: Frame
Family Room: Vaulted Ceiling(s), Flooring - Hardwood
Fireplace Features: Family Room, Master Bedroom
Fireplace Y/N: Yes
Flooring: Tile, Marble, Hardwood, Flooring - Hardwood, Flooring - Stone/Ceramic Tile, Flooring - Wall to Wall Carpet
GarageY/N: Yes
HeatingY/N: 1
Hot Tub: Yes
Kitchen: 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, Wainscotin
Laundry: Flooring - Stone/Ceramic Tile, First Floor, Electric Dryer Hookup
Living Room: Flooring - Hardwood, French Doors
Lot Features: Wooded
Master Bathroom: Yes
Master Bedroom: 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)
Office: Closet/Cabinets - Custom Built
Open Parking Y/N: Yes
Parcel Number: M:027 B:0342 L:0,901606
Parking Features: Attached, Paved Drive, Paved
Parking Total: 9
Patio And Porch: Porch, Porch - Enclosed, Deck, Patio, Enclosed
Road Responsibility: Public Maintained Road
Rooms Total: 16
Sauna: Yes
Security: yes
Security Features: Security System
Sewer: Public Sewer
Utilities: for Gas Range, for Electric Range, for Gas Oven, for Electric Oven, for Electric Dryer
Water: Public
Window Features: Insulated Windows
Wooded: Yes

Room Sizes

Bathroom 1: 8.00 X 5.00 Level - First
Bathroom 2: 10.00 X 7.00 Level - First
Bathroom 3: 16.00 X 12.00 Level - Second
Bedroom 2: 14.00 X 13.00 Level - Second
Bedroom 3: 15.00 X 15.00 Level - Second
Bedroom 4: 17.00 X 14.00 Level - Second
Bedroom 5: 19.00 X 13.00 Level - Basement
Dining Room: 14.00 X 13.00 Level - First
Family Room: 26.00 X 16.00 Level - First
Kitchen: 20.00 X 15.00 Level - Main,First
Living Room: 20.00 X 14.00 Level - First
Primary Bedroom: 31.00 X 23.00 Level - Second
Office: 9.00 X 9.00 Level - Second

Local Schools

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

Listed By / Shown By

Listed By

Agency Name: Compass
Agency Phone: 781-219-0313
Agent Name: Kim Covino & Co. Team

Shown By

Agent Name: Ayden Hardy
Agent Phone:
Agency Title: Better Homes and Gardens Real Estate The Masiello Group

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Estimated Payment

$ 10,410.84 per month $7,233.09 Principal & Interest $2,229.83 Property Tax $947.92 Homeowner's Insurance

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 04/18/2026. The listing information on this page last changed on 04/18/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Sat 04/18/2026 12:02:31 AM EST) or MLSPIN MLS (last updated Fri 04/17/2026 11:38:27 PM EST) or Prime MLS (last updated Fri 04/17/2026 11:33:41 PM EST) or MREIS (last updated Fri 04/17/2026 11:55:33 PM EST). Real estate listings held by brokerage firms other than Better Homes and Gardens Real Estate The Masiello Group may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.
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