257 High Street

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!

9/5/2025 11:30AM - 12:30PM EDT

5
beds

7
baths

7,101 Sq.Ft. LIVING AREA

1.68 Acres lot

Kim Covino

title Principal Agent
PHONE (781) 249-3854
EMAIL [email protected]
DRE # 100731

Features & Amenities

Interior

total bedrooms5
Total bathrooms7
full bathrooms5
half bathrooms2
Laundry room Flooring - Stone/Ceramic Tile, First Floor, Electric Dryer Hookup
Flooring Tile, Marble, Hardwood, Flooring - Hardwood, Flooring - Stone/Ceramic Tile, Flooring - Wall to Wall Carpet
Fireplace Family Room, Master Bedroom
APPLIANCES Gas Water Heater, Range, Oven, Dishwasher, Disposal, Microwave, Refrigerator, Freezer, Washer, Dryer, Range Hood, Other
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

Area & Lot

Status For Sale
OPEN HOUSE

9/5/2025 11:30AM - 12:30PM EDT
Living Area7,101 Sq.Ft.
Total Area7,101 Sq.Ft.
Lot Area1.68 Acres
MLS® ID73426449
TypeResidential
YEAR BUILT1994
Architecture StylesColonial, Contemporary
Elementary SchoolVinson Owen
Middle SchoolMccall Middle
High SchoolWinchester High

Exterior

Garage Space2.0
water SourcePublic
utilitiesfor Gas Range, for Electric Range, for Gas Oven, for Electric Oven, for Electric Dryer
roofShingle
lot featuresWooded
parkingAttached, Paved Drive, Paved
HEAT TYPEForced Air, Natural Gas, Fireplace
AIR CONDITIONINGCentral Air
sewerPublic Sewer
SubstructureConcrete Perimeter
security FeaturesSecurity System
other exterior FeaturesPorch, Porch - Enclosed, Deck, Patio, Patio - Enclosed, Balcony, Rain Gutters, Sprinkler System

Financial

Sales Price$3,499,000
Real Estate Tax $26,758/yr
Zoning res

Schedule a Showing

We would love to show you our beautiful property. Please select your preferred date and time below. An agent will be in touch shortly to confirm your appointment.

In Person

Via Video Chat

Schedule a Showing

We would love to show you our beautiful property. Please select your preferred date and time below. An agent will be in touch shortly to confirm your appointment.

By providing Kim Covino & Co your contact information, you acknowledge and agree to our Privacy Policy and consent to receiving marketing communications, including through automated calls, texts, and emails, some of which may use artificial or prerecorded voices. This consent isn’t necessary for purchasing any products or services and you may opt out at any time. To opt out from texts, you can reply, ‘stop’ at any time. To opt out from emails, you can click on the unsubscribe link in the emails. Message and data rates may apply.

Middle Name

Thank you for your interest in 257 High Street, Winchester, MA 01890. We are reviewing your request and will be in touch shortly!

Change time

Mortgage Calculator

Estimate your monthly mortgage payment, including the principal and interest, property taxes, and HOA. Adjust the values to generate a more accurate rate.

All estimates are provided for informational purposes only. Actual amounts may vary.

$0,000 Your Payment

Work With Us

My team and I have a proven track record when it comes to negotiating skills and sourcing buyers from many different markets thanks to our premiere listings and strong referral base spanning Winchester and beyond. Referrals from past and present clients have become the base of our business, further proving our unmatched service!

257 High Street

$3,499,000

Kim Covino

Features & Amenities

Interior

Area & Lot

Exterior

Financial

Schedule a Showing

Schedule a Showing

Mortgage Calculator

Work With Us

Follow Us on Instagram

Properties

257 High Street

$3,499,000

Kim Covino

Features & Amenities

Interior

Area & Lot

Exterior

Financial

Schedule a Showing

Schedule a Showing

Mortgage Calculator

Work With Us

Follow Us on Instagram

Contact Details

Kim Covino & Co.

Submit a Message