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23 Days on Jacob Realty
40
$999,900
4 Beds 2 Baths
HOA
N/A
SQFT
1719
258 Cross Street
Winchester, MA 01890
View Map

Property Description

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

Property Details

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: 07/08/26
  • HOA: No
  • Reqd Own Association: Unknown
  • Terms: Contract for Deed

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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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The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information 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. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein.

MLS PIN data last updated at 2026-07-08 12:49:00

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