OPEN HOUSE Sun, Nov 15 2026 10:30 AM - 12:00 PM
258 Cross St Winchester, MA - Image 1258 Cross St Winchester, MA - Image 2258 Cross St Winchester, MA - Image 3258 Cross St Winchester, MA - Image 4258 Cross St Winchester, MA - Image 5258 Cross St Winchester, MA - Image 6258 Cross St Winchester, MA - Image 7258 Cross St Winchester, MA - Image 8258 Cross St Winchester, MA - Image 9258 Cross St Winchester, MA - Image 10258 Cross St Winchester, MA - Image 11258 Cross St Winchester, MA - Image 12258 Cross St Winchester, MA - Image 13258 Cross St Winchester, MA - Image 14258 Cross St Winchester, MA - Image 15258 Cross St Winchester, MA - Image 16258 Cross St Winchester, MA - Image 17258 Cross St Winchester, MA - Image 18258 Cross St Winchester, MA - Image 19258 Cross St Winchester, MA - Image 20258 Cross St Winchester, MA - Image 21258 Cross St Winchester, MA - Image 22258 Cross St Winchester, MA - Image 23258 Cross St Winchester, MA - Image 24258 Cross St Winchester, MA - Image 25258 Cross St Winchester, MA - Image 26258 Cross St Winchester, MA - Image 27258 Cross St Winchester, MA - Image 28258 Cross St Winchester, MA - Image 29258 Cross St Winchester, MA - Image 30258 Cross St Winchester, MA - Image 31258 Cross St Winchester, MA - Image 32258 Cross St Winchester, MA - Image 33
OPEN HOUSE Sun, Nov 15 2026 10:30 AM - 12:00 PM

$919,000

4 Beds 2 / 1 Full / Half Baths 1,719 SQFT 0.18 Acres
Type: Single Family

258 Cross St
Winchester, MA 01890

MLS#: 73575764
Chris Bernier
Chris Bernier
Churchill Properties
Principal Broker/Owner
Phone: 978.578.5013
Office: 833.668.4649
Presented by: Justin Blankenship with Fiv Realty Co.

Property Description

 

MASSIVE PRICE IMPROVEMENT!!! 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 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 bedrooms 3 and 4 that allow you to expand your work and life styles, as your life changes, without needing to move. The bedrooms work well as kids rooms, guest suites, home office / gym, hobby spaces or all of the above! 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.


 

Interior Features

Bedrooms

Bedroom 2 FeaturesCloset, Flooring - Hardwood, Window(s) - Picture, Cable Hookup, High Speed Internet Hookup, Lighting - Overhead
Bedroom 3 Area149 sqft
Bedroom 3 FeaturesCloset, Flooring - Hardwood, Window(s) - Picture, Attic Access, Remodeled
Bedroom 3 Length11 sqft
Bedroom 3 LevelThird
Bedroom 3 Width12 sqft
Bedroom 4 Area143 sqft
Bedroom 4 FeaturesCloset, Flooring - Wall to Wall Carpet, Window(s) - Picture, Attic Access, Remodeled
Bedroom 4 Length11 sqft
Bedroom 4 LevelThird
Bedroom 4 Width12 sqft
Primary Bedroom Area244 sqft
Primary Bedroom FeaturesCeiling Fan(s), Closet/Cabinets - Custom Built, Flooring - Hardwood, Window(s) - Picture, Cable Hookup, High Speed Internet Hookup
Primary Bedroom Length17 sqft
Primary Bedroom Width14 sqft
Primary on Main161.208333333
Second Bedroom Length13 sqft
Second Bedroom LevelSecond
Second Bedroom Width12 sqft
Total Bedrooms4

Bathrooms

Bathroom 1 LevelSecond
Bathroom 2 LevelSecond
Bathroom 3 LevelFirst
Half Baths1
Total Baths3

Kitchen

Kitchen Area205 sqft
Kitchen FeaturesCeiling Fan(s), Flooring - Stone/Ceramic Tile, Window(s) - Picture, Countertops - Stone/Granite/Solid, Cabinets - Upgraded, Exterior Access, Recessed Lighting, Remodeled, Stainless Steel Appliances, Gas Stove
Kitchen Length13 sqft
Kitchen LevelMain, First
Kitchen Width15 sqft

Other Interior Features

LivingAreaSource0 sqft
Above Grade Finished Area1,719 sqft
Air Conditioning Y/NYes
BasementFull, Concrete, Unfinished
Fireplace Y/NNo
FlooringWood, Tile, Carpet, Hardwood
Heating Y/NYes
Interior AmenitiesInternet Available - Unknown
Laundry FeaturesIn Basement
Total Fireplaces0

Other Rooms

Dining Room Area12 sqft
Dining Room Area185 sqft
Dining Room FeaturesFlooring - Hardwood, Window(s) - Picture, Lighting - Pendant, Crown Molding
Dining Room LevelMain, First
Dining Room Width14 sqft
Kitchen Area205 sqft
Kitchen FeaturesCeiling Fan(s), Flooring - Stone/Ceramic Tile, Window(s) - Picture, Countertops - Stone/Granite/Solid, Cabinets - Upgraded, Exterior Access, Recessed Lighting, Remodeled, Stainless Steel Appliances, Gas Stove
Kitchen Length13 sqft
Kitchen LevelMain, First
Kitchen Width15 sqft
Living Room Area238 sqft
Living Room FeaturesFlooring - Hardwood, Window(s) - Bay/Bow/Box, Cable Hookup, High Speed Internet Hookup, Lighting - Overhead, Crown Molding, Vestibule
Living Room Length13 sqft
Living Room LevelMain, First
Living Room Width17 sqft

General

AppliancesGas Water Heater, Range, Dishwasher, Disposal, Microwave, Refrigerator, Freezer, Washer, Dryer
Architectural StyleColonial
Building Area Units0 sqft
Certified TreatedUnknown
CityWinchester
Community FeaturesPublic 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-Sta
Construction MaterialsFrame
CoolingCentral Air
CountyMiddlesex
DirectionsGPS
DisclosuresSome photos have been adjusted using AI technology. Please park on River street for showings. Previously prepared 2020 conceptual addition plans available for review. Plans are historical only and ha
Elementary SchoolLynch Elementary School
Exclusions1/2 Bathroom Mirror
Full Baths2
Garage Spaces0
Garage Y/NNo
HOANo
HeatingCentral, Forced Air
High SchoolWinchester High School
Home Warranty Y/NNo
Lot Size Square Feet7,700 sqft
Lot Size UnitsAcres
MLS AreaWinchester Highlands
Middle/Junior High SchoolMccall Middle School
Parcel Number898,140
Patio/Porch FeaturesPatio
Primary Bedroom LevelSecond
Property Attached Y/NNo
Property SubtypeSingle Family Residence
Property TypeResidential
RoofShingle
Senior Community Y/NNo
SewerPublic Sewer
Standard StatusActive
StatusActive
Tax Annual Amount$9,592
Tax Assessed Value$865,700
Tax Year2026
Total Rooms7
Utilitiesfor Gas Range
WaterviewNo
Year Built1860
Year Built DetailsApproximate
Year Built SourcePublic Records
ZoningRG

Exterior

Building Area Total1,719 sqft
Covered Spaces0
Exterior AmenitiesPatio, Storage, Professional Landscaping, Fenced Yard, Garden
FencingFenced/Enclosed, Fenced
Foundation DetailsStone
Lot FeaturesCorner Lot, Level
Lot Size Acres0.18
Lot Size Area0 sqft
Parking FeaturesOff Street, Deeded, Paved
Road Frontage TypePublic
Road ResponsibilityPublic Maintained Road
Road Surface TypePaved
SpaNo
Total Parking4
Water SourcePublic
Waterfront Y/NNo

Additional Details

Price History

Schools 

Middle School McCall Middle School
High School Winchester High School
Elementary School Lynch Elementary School

  

Similar Properties

$919,000

4 Beds 2 / 1 Full / Half Baths 1,719 SQFT 0.18 Acres
Type: Single Family

258 Cross St
Winchester, MA 01890

MLS#: 73575764
Chris Bernier
Chris Bernier
Churchill Properties
Principal Broker/Owner
Phone: 978.578.5013
Office: 833.668.4649