258 Cross St, Winchester, MA

$974,900

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3

Beds

Baths

1,719

Square feet

0.18

Acres

About 258 Cross St

A rare opportunity to own a detached home in Winchester under $1M—with the space, privacy and flexibility often missing from condo or townhome living. Tired of or can't imagine paying an HOA fee on top of fighting rising interest rates? Skip the added cost, lock in (REFI LATER) a lower monthly payment, and get more value at 258 Cross Street! The property is set on a level, fenced corner lot with a side-street driveway, ACCESSIBLE FROM RIVER STREET, parking for 4 cars, and offering 3 bedrooms, a versatile bonus room (4 beds on public record), 2.5 baths and a layout that can adapt as your needs change. The main level blends classic character with everyday function, featuring hardwood floors, crown molding, arched openings, bay windows and an updated eat-in kitchen with stone counters, upgraded cabinetry, stainless appliances and gas cooking. A brand-new first-floor powder room adds convenience for everyday living and entertaining. Upstairs, two generously sized bedrooms are joined by two updated full baths, including a larger bath with double vanity, tiled shower and soaking tub. The finished third floor provides a third bedroom plus an additional flex space ideal for a home office, fitness room, playroom, hobby space or guests. Major recent improvements, besides the unused, first floor half bath, include brand-new central AC and a newly sodded yard. Current owners have also invested considerably into improvements from the kitchen (countertops/appliances/backsplash/flooring), to the main bathroom remodel on the 2nd floor, and even a rebuilding of the lower two staircases to increase functionality. Outside, enjoy a fenced backyard, patio, storage shed and rare off-street parking for four vehicles. The full basement provides additional laundry and storage space. Convenient to Winchester Center, local shops and dining, the commuter rail, the Middlesex Fells and major routes connecting Boston, Cambridge, Burlington and the surrounding metro area. Previously prepared conceptual expansion plans are available for buyers interested in exploring future possibilities.

Open House

Sun, Sep 20th, 2026 @ 10:30am - 12pm

Features of 258 Cross St

MLS® # 73575764
Price $974,900
Bedrooms 3
Bathrooms 2.50
Full Baths 2
Half Baths 1
Square Footage 1,719
Acres 0.18
Year Built 1860
Type Residential
Sub-Type Single Family Residence
Style Colonial
Status Active

Community Information

Address 258 Cross St
Area Winchester Highlands
City Winchester
County Middlesex
State MA
Zip Code 01890

Amenities

Utilities for Gas Range
Parking Spaces 4
Parking Off Street, Deeded, Paved
Is Waterfront No
Has Pool No

Interior

Fireplace No

School Information

Elementary Lynch Elementary School
Middle Mccall Middle School
High Winchester High School

Additional Information

Zoning RG

Listing Details

Agent Justin Blankenship
Office Fiv Realty Co

Listing Map

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