258 Cross Street, Winchester HighlandsWinchester, MA 01890MLS Number 73575764

  • Price: $974,900
  • Est. Mortgage of $/month
  • 45 Days on Market
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$
%
$/month over payments
Federal 30-year interest rate: 7.32% last updated on Oct 22, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.
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258 Cross Street Winchester MA 01890258 Cross Street Winchester MA 01890258 Cross Street Winchester MA 01890258 Cross Street Winchester MA 01890258 Cross Street Winchester MA 01890258 Cross Street Winchester MA 01890258 Cross Street Winchester MA 01890258 Cross Street Winchester MA 01890258 Cross Street Winchester MA 01890258 Cross Street Winchester MA 01890258 Cross Street Winchester MA 01890258 Cross Street Winchester MA 01890258 Cross Street Winchester MA 01890258 Cross Street Winchester MA 01890258 Cross Street Winchester MA 01890258 Cross Street Winchester MA 01890258 Cross Street Winchester MA 01890258 Cross Street Winchester MA 01890258 Cross Street Winchester MA 01890258 Cross Street Winchester MA 01890258 Cross Street Winchester MA 01890258 Cross Street Winchester MA 01890258 Cross Street Winchester MA 01890258 Cross Street Winchester MA 01890258 Cross Street Winchester MA 01890258 Cross Street Winchester MA 01890258 Cross Street Winchester MA 01890258 Cross Street Winchester MA 01890258 Cross Street Winchester MA 01890258 Cross Street Winchester MA 01890258 Cross Street Winchester MA 01890258 Cross Street Winchester MA 01890258 Cross Street Winchester MA 01890258 Cross Street Winchester MA 01890
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  • 3Bedrooms
  • 0.18Acreage
  • 3Bathrooms
  • 1860Year Built

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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 of Fiv Realty Co

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More Info

Basic Information

  • Bedrooms3
  • Mls StatusActive
  • Bathroom3
  • Listing Terms Contract
  • Lot Features Corner Lot, Level
  • Parcel Number 898140
  • Road Frontage DescriptionPaved

Location

  • NeighborhoodWinchester Highlands
  • SubdivisionWinchester Highlands
  • Address258 Cross Street
  • Building Number258
  • CountyMiddlesex
  • StateMA
  • StreetCross Street
  • TownWinchester
  • Zip01890

Property

  • Acreage0.18

Interior

  • Flooring Wood, Tile, Carpet, Hardwood
  • Interior Features Internet Available - Unknown

Utilities

  • Cooling Central Air
  • Cooling YN Yes
  • Heat SystemYes
  • Heating Central, Forced Air
  • Sewer Public Sewer
  • Water Source Public

Other

  • Date Listed09/11/2026
  • Farm Land Area Units Square Feet

Tax Information

  • Tax Assessed Value $865,700
  • Tax Year 2026
  • Taxes$9,591

Parking

  • Parking Spaces4
  • Open Parking YN Yes
  • Parking Features Off Street, Deeded, Paved

Basic Information

  • List Price$974,900
  • MLS Number73575764
  • Modification Date10/15/2026
  • Property SubTypeSingle Family Residence
  • Virtual TourView Tour

Building

  • BasementFull, Concrete, Unfinished
  • Building Area Units Square Feet
  • Construction Materials Frame
  • FoundationStone
  • Patio And Porch Features Patio
  • Property StyleColonial
  • Rooms7
  • Utilities For Gas Range
  • Year Built1860
  • Year Built Details Approximate
  • Year Built Source Public Records

Amenities

  • Amenities
    • Bike Path
    • Conservation Area
    • Golf
    • Highway Access
    • House of Worship
    • Medical Facility
    • Park
    • Pool
    • Private School
    • Public School
    • Public Transportation
    • Shopping
    • Sidewalks
    • Stable(s)
    • T-Station
    • Tennis Court(s)
    • University
    • Walk/Jog Trails
  • Appliances IncludedGas Water Heater, Range, Dishwasher, Disposal, Microwave, Refrigerator, Freezer, Washer, Dryer

School Information

  • High School Winchester High School
  • Elementary SchoolLynch Elementary School
  • Junior HighMccall Middle School

Rooms

  • Bathroom 1 Second,9.083333333 x 8.833333333
  • Bathroom 2 Second,6.75 x 4.5
  • Bathroom 3 First,5 x 4
  • Bathrooms Total Decimal 2.5
  • Bedroom 2 Second,13.25 x 12.166666666
  • Bedroom 3 Third,11.75 x 12.75
  • Bedroom 4 Third,11.75 x 12.25
  • Dining Room Main, First,12.833333333 x 14.416666666
  • Full Bath2
  • Half Baths1
  • Kitchen Main, First,13 x 15.833333333
  • Living Room Main, First,13.333333333 x 17.916666666
  • Master Bedroom Second,17.25

Exterior

  • Exterior Features Patio, Storage, Professional Landscaping, Fenced Yard, Garden
  • Fencing Fenced/Enclosed, Fenced
  • RoofShingle

Property Information

  • Square Feet1,719
  • Building Area Source Public Records
  • Living Area 1,719
  • Lot Size Square Feet 7,700
  • Lot Size Units Acres
  • Road Responsibility Public Maintained Road

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The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. (MLSPIN) from third party sources, including sellers, lessors and public records, and were compiled by MLSPIN. The property listing data and information, and the Images, are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLSPIN and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

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