Off Market
258 Cross St, Winchester, MA
Winchester · MA 01890
- $999,900
- Price
- 4
- Beds
- 2
- Baths
- 1719
- Sq. ft.
Overview
Property type:
Single Family
Year built:
Built in 1860
Lot size:
7,700 Sq.Ft Lot
Price per square foot:
$582 / Sq.Ft
Parking:
4 Off Street Spaces
Heating & cooling:
Heat, AC
About this home
A rare Winchester opportunity under $1M, 258 Cross Street blends timeless character, meaningful updates, everyday function, and exciting long-term upside. Set on a level, fenced corner lot, this 4 bed, 2 bath Colonial offers the space buyers need today with the flexibility to evolve over time. Inside - hardwood floors, crown molding, arched openings, bay windows, and detailed trim add warmth, while the updated kitchen features stone counters, upgraded cabinetry, stainless appliances, gas cooking, and great natural light. Both full baths have been tastefully updated, including a larger bath with double vanity, tiled shower, and soaking tub. Four bedrooms on the upper levels create options for guests, office, fitness, hobbies, or future needs. Brand new AC, central heat, full basement with laundry/storage, patio, fenced yard, shed, and 4-car parking add real utility. Previously prepared conceptual expansion plans are available for review. Minutes from the iconic, and picturesque downtown. Rear vestibule is the perfect place for a 1st floor half bath (see attached rendering). Smaller upstairs bathroom could be converted to a 1/2 bath with stackable laundry or a dedicated laundry room (SEE ATTACHED RENDERINGS).
Neighborhood & Transit
Winchester Highlands
258 Cross St, Winchester · MA 01890
Nearby transit
Within 0.5 mile, measured straight-line to the nearest station entrance.
No subway or commuter rail stations within 0.5 mile.
Price Insight
- Days on Market:
- 133 days
- Listing Price:
- $999,900
- Price per Sq.Ft:
- $582
- Tax Assessment:
- $865,700 in 2026
- Taxes:
- $799 / Monthly
Home Facts
Interior Features
- Bedrooms
- 4
- Full Bathrooms
- 2
- Half Bathrooms
- 0
- Living Area
- 1,719 Sq.Ft
- Broker Disclosure about Living Area
- All measurements provided are for marketing purposes only. Buyer(s) to perform their due diligence
- Kitchen
- Main Floor, Upgraded Cabinets, Gas Stove, Stainless Steel Appliances, Stone Countertops, Ceiling Fan(s), Flooring - Stone/Ceramic Tile, Window(s) - Picture, Main Level, Exterior Access, Recessed Lighting, Remodeled, Vestibule, Dishwasher, Range, Garbage Disposal, Microwave, Refrigerator, Freezer, Washer, Dryer
- Primary Bedroom
- Floor 2, Custom Built Closet/Cabinets, Ceiling Fan(s), Flooring - Hardwood, Window(s) - Picture, Cable Hookup, High Speed Internet Hookup
- Laundry
- Unknown
- Living levels
- Unknown
- Rooms
- 7
- Above grade area
- 1719
- Flooring
- Wood, Tile, Wall to Wall Carpet, Hardwood
- Lead paint
- Unknown
Utilities
- Heating Type
- Central Heat, Forced Air
- Heating Zone
- 1
- Cooling
- Central Air
- Cooling Zones
- 1
- Water
- City/Town Water
- Sewer
- City/Town Sewer
- Electric Features
- Unknown
Exterior Features
- Lot Size
- 7,700 Sq.Ft
- Lot Description
- Corner Lot, Fenced/Enclosed, Level
- Exterior Features
- Garden Area, Patio, Storage Shed, Professional Landscaping, Fenced Yard
Parking
- Garage Parking
- 0 Parking Spaces
- Off Street Parking
- 4 Parking Spaces, Off-Street, Paved Driveway, Deeded
Construction Details
- Construction Type
- Frame
- Siding
- Shingles, Wood, Aluminum
- Roof
- Asphalt/Fiberglass Shingles
Green Features
- Electric Vehicle Charger
- Unknown
- Solar Panels
- Unknown
- Green Certified
- Unknown
- Insulation Features
- Unknown
- Energy Features
- Unknown
Room details
- Living room level
- First Floor
- Living room dimensions
- 13'4X17'11
- Living room features
- Flooring - Hardwood, Window(s) - Bay/Bow/Box, Main Level, Cable Hookup, High Speed Internet Hookup, Lighting - Overhead, Crown Molding, Vestibule
- Dining room level
- First Floor
- Dining room dimensions
- 12'10X14'5
- Dining room features
- Flooring - Hardwood, Window(s) - Picture, Main Level, Lighting - Pendant, Crown Molding
- Kitchen dimensions
- 13'X15'10
- Primary bedroom dimensions
- 17'3X14'2
- Bedroom 2 level
- Second Floor
- Bedroom 2 dimensions
- 13'3X12'2
- Bedroom 2 features
- Closet, Flooring - Hardwood, Window(s) - Picture, Cable Hookup, High Speed Internet Hookup, Lighting - Overhead
- Bedroom 3 level
- Third Floor
- Bedroom 3 dimensions
- 11'9X12'9
- Bedroom 3 features
- Closet, Flooring - Hardwood, Window(s) - Picture, Attic Access, Remodeled
- Bedroom 4 level
- Third Floor
- Bedroom 4 dimensions
- 11'9X12'3
- Bedroom 4 features
- Closet, Flooring - Wall to Wall Carpet, Window(s) - Picture, Attic Access, Remodeled
- Bathroom 1 level
- Second Floor
- Bathroom 1 dimensions
- 9'1X8'10
- Bathroom 1 features
- Bathroom - Full, Bathroom - Double Vanity/Sink, Bathroom - With Tub & Shower, Flooring - Stone/Ceramic Tile, Window(s) - Picture, Countertops - Stone/Granite/Solid, Countertops - Upgraded, Bidet, Cabinets - Upgraded, Remodeled, Lighting - Overhead, Soaking Tub
- Bathroom 2 level
- Second Floor
- Bathroom 2 dimensions
- 6'9X4'6
- Bathroom 2 features
- Bathroom - Full, Bathroom - With Tub, Flooring - Stone/Ceramic Tile, Window(s) - Picture, Remodeled, Lighting - Overhead, Pedestal Sink, Soaking Tub
Listing information
- Listing agent
- Justin Blankenship
- Listing office
- Fiv Realty Co
- MLS PIN #
- 73541288
- Disclosure
- Some photos have been adjusted using AI technology. Please park on River street for showings but enter through the front door on Cross street.
- Disclosure
- All measurements provided are for marketing purposes only. Buyer(s) to perform their due diligence
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