258 Cross Street, Winchester, MA 01890
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$999,900
4 Beds
2 Baths
1719 SQFT
0.18 Acre
HOA: N/A

Property Description

Welcome to 258 Cross Street, a masterfully updated Winchester Colonial blending timeless character, modern comfort, and everyday function. Set on a level, fenced corner lot, this 4 bed, 2 bath home offers endless outdoor opportunity to relax, entertain, play, or dine al fresco. Inside, hardwood floors, crown molding, arched openings, bay windows, and ornate detail bring warmth and personality. The modernized kitchen beams with natural light and features upgraded cabinetry, stone counters, stainless appliances, and gas cooking. Both full baths have been tastefully updated with the larger featuring a tiled stand up shower, free standing soaking tub and a double vanity. Four bedrooms across the upper levels create flexibility for growing families, guests, WFH, fitness, or hobbies. Brand new central AC, central heat, full basement with laundry, and 4-car parking add functionality. Minutes from downtown Winchester with the most scenic downtown around, lined with shops, dining and even the T

Property Details tap to expand

Amenities

  • Bike Path
  • Conservation Area
  • Golf Course
  • Highway Access
  • House of Worship
  • Medical Facility
  • Park
  • Private School
  • Public School
  • Public Transportation
  • Shopping
  • Stables
  • Swimming Pool
  • T-Station
  • Tennis Court
  • University
  • Walk/Jog Trails

Kitchen, Dining, and Appliances

  • Kitchen Dimensions: 13X15'10"
  • Cabinets - Upgraded, Ceiling Fan(s), Countertops - Stone/Granite/Solid, Exterior Access, Flooring - Stone/Ceramic Tile, Gas Stove, Recessed Lighting, Remodeled, Stainless Steel Appliances, Vestibule, Window(s) - Picture
  • Dishwasher, Disposal, Dryer, Freezer, Microwave, Range, Refrigerator, Washer
  • Dining Room Dimensions: 12'10"X14'5"
  • Dining Room Features: Crown Molding, Flooring - Hardwood, Lighting - Pendant, Window(s) - Picture

Bathrooms

  • Full Baths: 2
  • Bathroom 1 Dimensions: 9'1"X8'10"
  • Bathroom 1 Level: Second Floor
  • Bathroom 1 Features: Bathroom - Double Vanity/Sink, Bathroom - Full, Bathroom - With Tub & Shower, Bidet, Cabinets - Upgraded, Countertops - Stone/Granite/Solid, Countertops - Upgraded, Flooring - Stone/Ceramic Tile, Lighting - Overhead, Remodeled, Soaking Tub, Window(s) - Picture
  • Bathroom 2 Dimensions: 6'9"X4'6"
  • Bathroom 2 Level: Second Floor
  • Bathroom 2 Features: Bathroom - Full, Bathroom - With Tub, Flooring - Stone/Ceramic Tile, Lighting - Overhead, Pedestal Sink, Remodeled, Soaking Tub, Window(s) - Picture

Bedrooms

  • Bedrooms: 4
  • Master Bedroom Dimensions: 17'3"X14'2"
  • Master Bedroom Level: Second Floor
  • Master Bedroom Features: Cable Hookup, Ceiling Fan(s), Closet/Cabinets - Custom Built, Flooring - Hardwood, High Speed Internet Hookup, Window(s) - Picture
  • Bedroom 2 Dimensions: 13'3"X12'2"
  • Bedroom 2 Level: Second Floor
  • Master Bedroom Features: Cable Hookup, Closet, Flooring - Hardwood, High Speed Internet Hookup, Lighting - Overhead, Window(s) - Picture
  • Bedroom 3 Dimensions: 11'9"X12'9"
  • Bedroom 3 Level: Third Floor
  • Master Bedroom Features: Attic Access, Closet, Flooring - Hardwood, Remodeled, Window(s) - Picture

Other Rooms

  • Total Rooms: 7
  • Living Room Dimensions: 13'4"X17'11"
  • Living Room Features: Cable Hookup, Crown Molding, Flooring - Hardwood, High Speed Internet Hookup, Lighting - Overhead, Vestibule, Window(s) - Bay/Bow/Box
  • Laundry Room Features: Concrete Floor, Full, Unfinished Basement

Utilities

  • Heating: Central Heat, Forced Air
  • Heat Zones: 1
  • Hot Water: Natural Gas
  • Cooling: Central Air
  • Cooling Zones: 1
  • Utility Connections: for Gas Range
  • Water: City/Town Water
  • Sewer: City/Town Sewer

Garage & Parking

  • Parking Features: Deeded, Off-Street, Paved Driveway
  • Parking Spaces: 4

Interior Features

  • Square Feet: 1719
  • Interior Features: Internet Available - Unknown
  • Accessability Features: Unknown

Construction

  • Year Built: 1860
  • Type: Detached
  • Style: Colonial
  • Construction Type: Frame
  • Foundation Info: Fieldstone
  • Roof Material: Asphalt/Fiberglass Shingles
  • Flooring Type: Hardwood, Tile, Wall to Wall Carpet, Wood
  • Lead Paint: Unknown
  • Warranty: No

Exterior & Lot

  • Lot Description: Corner, Fenced/Enclosed, Level
  • Exterior Features: Fenced Yard, Garden Area, Patio, Professional Landscaping, Storage Shed
  • Road Type: Paved, Public, Publicly Maint., Sidewalk

Other Information

  • MLS ID# 73541288
  • Last Updated: 06/24/26
  • HOA: No
  • Reqd Own Association: Unknown
  • Terms: Contract for Deed

Property History tap to expand

Date Event Price Price/Sq Ft Source
06/24/2026New$999,900$582MLSPIN

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Map

Seller's Representative: Justin Blankenship, Fiv Realty Co
Sub Agent Compensation: n/a
Buyer Agent Compensation: n/a
Facilitator Compensation: n/a
Compensation Based On: n/a
Sub-Agency Relationship Offered: No

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MLS PIN data last updated at 2026-06-24 22:21:00

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