$999,900 ($581.68 per sqft)

Est. Mortgage $4,860/mo *

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Missed out on the best value in Winchester pre-4th? Round 2 of open houses are out! This may feel like just a starter home but it is so much more than that. Come discover this hidden gem while it lasts. Please park on River street and be sure you and or your buyer sign in with my colleague Monica.

07/11/2026
12:30 PM to 2:00 PM
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07/12/2026
12:30 PM to 2:00 PM
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258 Cross Street, Winchester, (Winchester Highlands), MA, 01890

258 Cross Street, Winchester, (Winchester Highlands), MA, 01890
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7 rooms

4 beds

2 Full baths

1860

Colonial

1,719 sqft

A rare Winchester opportunity under $1M, 258 Cross Street blends timeless character, meaningful updates, everyday function, and exciting long-term upside. Set on a level, fenced corner lot, this 4 bed, 2 bath Colonial offers the space buyers need today with the flexibility to evolve over time. Inside - hardwood floors, crown molding, arched openings, bay windows, and detailed trim add warmth, while the updated kitchen features stone counters, upgraded cabinetry, stainless appliances, gas cooking, and great natural light. Both full baths have been tastefully updated, including a larger bath with double vanity, tiled shower, and soaking tub. Four bedrooms on the upper levels create options for guests, office, fitness, hobbies, or future needs. Brand new AC, central heat, full basement with laundry/storage, patio, fenced yard, shed, and 4-car parking add real utility. Previously prepared conceptual expansion plans are available for review. Minutes from the iconic, and picturesque downtown

Status:

Active

Town:

Winchester

Type:

Single-family residential

Laundry Remarks:

In Basement

Zoning:

RG

Heating:

Central, Forced Air

Cooling:

Central Air

Basement:

Full, Concrete, Unfinished

Parking:

4-car, Off Street, Deeded, Paved

Acreage:

0.18

Est. Taxes:

$9,592

Assessment

$865,700

Construction

Frame

Utilities

for Gas Range

Lot Description:

Corner Lot, Level

Amenities:

Public Transportation, Shopping, Pool, Tennis Court(s), Park, Walk/Jog Trails, Stable(s), Golf, Medical Facility, Bike Path, Conservation Area, Highway Access, House of Worship, Private School, Public School, T-Station, University, Sidewalks

Elementary School:

Lynch Elementary School

Middle School:

Mccall Middle School

High School:

Winchester High School

Appliances:

Gas Water Heater, Range, Dishwasher, Disposal, Microwave, Refrigerator, Freezer, Washer, Dryer

MLS #:

73541288

Community Info

School Info

Walk Score

Mass Transit

Yelp

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Listing courtesy of Justin Blankenship, FIV Realty Co 781-365-7984