Welcome to 258 Cross Street, a masterfully updated Winchester Colonial blending timeless character, modern comfort, and everyday function. Set on a level, fenced corner lot, this 4 bed, 2 bath home offers endless outdoor opportunity to relax, entertain, play, or dine al fresco. Inside, hardwood floors, crown molding, arched openings, bay windows, and ornate detail bring warmth and personality. The modernized kitchen beams with natural light and features upgraded cabinetry, stone counters, stainless appliances, and gas cooking. Both full baths have been tastefully updated with the larger featuring a tiled stand up shower, free standing soaking tub and a double vanity. Four bedrooms across the upper levels create flexibility for growing families, guests, WFH, fitness, or hobbies. Brand new central AC, central heat, full basement with laundry, and 4-car parking add functionality. Minutes from downtown Winchester with the most scenic downtown around, lined with shops, dining and even the T
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Winchester Highlands
258 Cross Street, Winchester MA 01890
Winchester, MA 01890
School information not available for this location.
| Date | Event | Price | Change | $/sqft | Details |
|---|---|---|---|---|---|
| 06/24/2026 | 🏠 Listed for Sale | $999,900 | - | - | Original listing |
| 06/01/2020 | 🏷️ Previously Sold | $699,000 | - | - | MLS #72585005 |
| 01/25/2019 | 🏷️ Previously Sold | $607,500 | - | - | MLS #72380664 |
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