257 High Street, Winchester MA 01890

Winchester, MA 01890 • West Side

$3,299,000

Est. $19,111/month

5

Beds

6

Baths

7,101

Sq Ft

$465

Price/Sq Ft

1.68

Acres

1994

Year Built

Single Family Residence

Type

92

Days on Market

Active Price Drop -$200,000 Listed Sep 5, 2025 • MLS# 73426449 Copied!

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!

Property Overview

Property Type

Single Family Residence

Listing Type

For Sale

Year Built

1994

Bedrooms

5

Full Bathrooms

5

Half Bathrooms

2

Living Area

7,101 sq ft

Total Rooms

16

Facts & Features

2 Car Garage

Central AC

Home Facts

Type Residential

Style Single Family Residence

Year Built 1994

Living Area 7,101 sq ft

Lot Size 1.68 acres

Bedrooms 5

Full Baths 5

Half Baths 2

Total Rooms 16

Interior

Heating Forced Air, Natural Gas, Fireplace

Cooling Central Air

Flooring Tile, Marble, Hardwood, Flooring - Hardwood, Flooring - Stone/ceramic Tile, Flooring - Wall To Wall Carpet

Appliances Gas Water Heater, Range, Oven, Dishwasher, Disposal, Microwave, Refrigerator, Freezer, Washer, Dryer, Range Hood, Other

Fireplace Family Room, Master Bedroom

Fireplaces 4

Basement Full, Finished, Walk-out Access, Interior Entry

Laundry Flooring - Stone/ceramic Tile, First Floor, Electric Dryer Hookup

Features 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

Exterior

Construction Frame

Architecture Colonial, Contemporary

Roof Shingle

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

Pool None

Spa None

Fencing None

Patio/Porch Porch, Porch - Enclosed, Deck, Patio, Enclosed

Parking

Garage Spaces 2

Has Garage Yes

Features Attached, Paved Drive, Paved

Total Spaces 9

Utilities

Electric 200+ Amp Service

Water Public

Sewer Public Sewer

Gas None

Other For Gas Range, For Electric Range, For Gas Oven, For Electric Oven, For Electric Dryer

Financial

Annual Tax $26,758

Assessed Value $2,412,800

Interior Features

Flooring: Tile, Marble, Hardwood, Flooring - Hardwood, Flooring - Stone/Ceramic Tile, Flooring - Wall to Wall Carpet

Appliances: Gas Water Heater, Range, Oven, Dishwasher, Disposal, Microwave, Refrigerator, Freezer, Washer, Dryer, Range Hood, Other

Interior Features: 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

Windows: Insulated Windows

Basement: Full, Finished, Walk-Out Access, Interior Entry

Laundry: Flooring - Stone/Ceramic Tile, First Floor, Electric Dryer Hookup

Security: Security System

Construction & Materials

Style: Colonial, Contemporary

Year Built: 1994

Structure Type:

Exterior Materials: Frame

Roof: Shingle

Foundation: Concrete Perimeter

Heating, Cooling & Utilities

Heating: Forced Air, Natural Gas, Fireplace

Heating Zones: 3

Cooling: Central Air

Cooling Zones: 3

Hot Water:

Water Source: Public

Sewer: Public Sewer

Energy Features:

Exterior & Lot

Exterior Features: Porch, Porch - Enclosed, Deck, Patio, Patio - Enclosed, Balcony, Rain Gutters, Sprinkler System

Patio & Porch: Porch, Porch - Enclosed, Deck, Patio, Enclosed

Fencing:

Other Structures:

Lot Features: Wooded

Road Surface: Paved

Parking & Garage

Garage Spaces: 2

Garage Type: Attached

Total Parking Spaces: 9

Parking Features: Attached, Paved Drive, Paved

Special Features

Fireplaces: 4

Fireplace Type: Family Room, Master Bedroom

Community Amenities: Walk/Jog Trails, Public School

Location

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Neighborhood

West Side

257 High Street, Winchester MA 01890

Winchester, MA 01890

Walkability

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Schools

Elementary School

Vinson Owen

Rating information coming soon

Middle School

Mccall Middle

Rating information coming soon

High School

Winchester High

Rating information coming soon

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Principal & Interest $0

Property Tax $2,230

Homeowners Insurance $200

PMI (if <20% down) $0

Loan Summary

Total of 360 payments $0

Total principal paid $0

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Payment Over Time

Interest

Principal

Year 1

95% Interest

Year 15

50/50

Year 30

95% Principal

* Estimates only. Actual payments may vary. Consult with a lender for accurate figures.

Property History

Property Timeline

🏠

Listed for Sale

Sep 5, 2025

$3,299,000

Original listing

Agent: Kim Covino & Co. Team Office: Compass

Date	Event	Price	Change	$/sqft	Details
09/05/2025	🏠 Listed for Sale	$3,299,000	-	-	Original listing

Price & Status History

Date	Event	Price	Change
Sep 5, 2025	New Listing Added	$3,299,000	—

Market Statistics

Days on Market

92 days

Price per Sq Ft

$465

Total Price Drop

-$200,000

Tax History

Year	Taxes	Assessment
2025	$26,758	$2,412,800

Financial Details

Annual Property Tax

$26,758

Tax Year 2025

Assessed Value

$2,412,800

Monthly Payment Breakdown

Loan Summary

Listed for Sale

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257 High Street, Winchester MA 01890

About this home

Property Overview

Facts & Features

Home Facts

Interior

Exterior

Parking

Utilities

Financial

Interior Features

Construction & Materials

Heating, Cooling & Utilities

Exterior & Lot

Parking & Garage

Special Features

Location

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Schools

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