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--IMMEDIATELY AVAILABLE --- A rare opportunity to rent a detached home in Winchester with the space, privacy and flexibility often missing from condo or townhome living. 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 4 bedrooms, 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. Pets negotiable. First month's rent & security deposit due at lease signing. Lease term negotiable.

More Info

Basic Information

  • Mls StatusNew
  • Parcel Number 898140
  • Rent Includes Water, Sewer

Parking

  • Parking Spaces4

Rooms

  • Bathroom3
  • Bathrooms Total Decimal 2.5
  • Bedrooms4
  • Full Bath2
  • Half Baths1

Basic Information

  • List Price$4,500
  • MLS Number73590971
  • Modification Date10/15/2026
  • Property SubTypeSingle Family Residence

Location

  • Address258 Cross Street
  • Building Number258
  • CountyMiddlesex
  • StateMA
  • StreetCross Street
  • TownWinchester
  • Zip01890

Building

  • Building Area Units Square Feet
  • Entry Level 1
  • Patio And Porch Features Patio
  • Rooms9
  • Year Built1860
  • Year Built Source Public Records

Exterior

  • Exterior Features Patio, Storage, Fenced Yard, Garden
  • Fencing Fenced

Utilities

  • Cooling YN Yes
  • Heat SystemYes
  • Heating Natural Gas

Property Information

  • Building Area Source Field Card
  • Living Area 1,719
  • Lot Size Square Feet 7,700
  • Lot Size Units Acres
  • Square Feet1,719

Amenities

  • Amenities
    • Bike Path
    • Conservation Area
    • Golf
    • Highway Access
    • House of Worship
    • Medical Facility
    • Park
    • Pool
    • Private School
    • Public School
    • Public Transportation
    • Shopping
    • Stable(s)
    • T-Station
    • Tennis Court(s)
    • University
    • Walk/Jog Trails
  • Appliances IncludedRange, Dishwasher, Disposal, Microwave, Refrigerator, Freezer, Washer, Dryer
  • Other AmenitiesBasement, Garden, Golf, Tennis
  • PetsYes w/ Restrictions

Other

  • Date Listed10/15/2026
  • Farm Land Area Units Square Feet

Map Location

Driving Directions

Listed by Justin Blankenship of Fiv Realty Co

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