Primary bedroom
- Level
- Second
- Area
- 244.38 sqft
- Length
- 17.25 ft
- Width
- 14.17 ft
- Features
- Ceiling Fan(s) · Closet/Cabinets - Custom Built · Flooring - Hardwood · Window(s) - Picture · Cable Hookup · High Speed Internet Hookup
FOR SALE · MLS #73575764
258 Cross St
Winchester, MA 01890
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Are rates making you feel like home buying is out of reach? The sellers are now offering A TWENTY THOUSAND DOLLAR ($20,000) CREDIT, PERFECT to put towards closing costs or a 2/1 rate buy down. Enjoy over a ONE THOUSAND ($1000) DOLLAR PER MONTH savings year one and over a FIVE HUNDRED ($500) DOLLAR PER MONTH savings year two. 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.
Listed by Justin Blankenship · Fiv Realty Co
MLS PIN #73575764 · Updated 10/15/2026, 9:20:00 AM ET
| Year | Property tax | Assessed value |
|---|---|---|
| 2026 | $9,591.95 | $865,700 |
These records are supplied by the current listing. Assessed value is not market value; confirm taxes with the local assessor.
Estimate principal and interest using the asking price and your loan assumptions.
Results include principal and interest, plus property tax and HOA when MLS lists them; home and mortgage insurance and utilities are excluded. Tax uses the amount in this listing; a buyer’s actual tax may differ with reassessment or residential exemptions. The rate is your assumption, not a current market quote or loan offer.
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Listings updated