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258 Cross Street, Winchester MA 01890
258 Cross Street, Winchester MA 01890
Massachusetts>Middlesex County>Winchester Town Center

258 Cross StreetWinchester, MA 01890

For Sale

$999,900

Smart Buyer Rebate $5,000

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

Listed by Justin Blankenship

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Fiv Realty Co

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617-918-7419

Last updated July 08, 2026

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Source: MLSPin #73541288

Listing Facts

  • TypeSingle-family
  • NeighborhoodWinchester Town Center
  • Bedrooms4
  • Bathrooms2
  • Days on Prevu38
  • Taxes$9,591.95/year
  • Size1,719 sqft
  • Price per sqft$582

Amenities

  • Dishwasher
  • Private Outdoor Space
  • Washer/Dryer
  • Air Conditioning
  • Parking
  • Swimming Pool

Location

Mortgage Calculator

Listing History

06/24/2026
Listed by Fiv Realty Co
$999,900

Property Details for 258 Cross Street

Association

Amenities

  • Community Features: Public 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-Station, University, Sidewalks

Exterior

Construction

  • Roof: Shingle
  • Year Built: 1860
  • Year Built Details: Approximate
  • Architectural Style: Colonial
  • Construction Materials: Frame
  • Exterior Features: Patio, Storage, Professional Landscaping, Fenced Yard, Garden

Features

  • Fencing: Fenced/Enclosed, Fenced
  • Patio And Porch Features: Patio
  • Road Frontage Type: Public

Measurements

  • Building Area Total: 1,719
  • Building Area Units: Square Feet
  • Lot Features: Corner Lot, Level
  • Lot Size Acres: 0.18
  • Lot Size Area: 0
  • Lot Size Square Feet: 7,700
  • Lot Size Units: Acres

Financial

Taxes

  • Parcel Number: 898140
  • Tax Annual Amount: $9,591.95
  • Tax Assessed Value: $865,700.00
  • Tax Year: 2026

Interior

Features

  • Appliances: Gas Water Heater, Range, Dishwasher, Disposal, Microwave, Refrigerator, Freezer, Washer, Dryer
  • Flooring: Wood, Tile, Carpet, Hardwood
  • Interior Features: Internet Available - Unknown

Measurements

  • Living Area: 1,719
  • Living Area Source: Public Record

Rooms

  • Basement: Full, Concrete, Unfinished
  • Bathrooms Full: 2
  • Bathrooms Total Integer: 2
  • Bedrooms Total: 4
  • Rooms Total: 7

Parking

Parking

  • Open Parking Spaces: 4
  • Open Parking: Yes
  • Parking Features: Off Street, Deeded, Paved
  • Parking Total: 4

Schools

Elementary School

  • Elementary School: Lynch Elementary School

High School

  • High School: Winchester High School

Middle or Junior School

  • Middle Or Junior School: Mccall Middle School

Utilities

Equipment

  • Cooling: Central Air
  • Has Cooling: Yes
  • Heating: Central, Forced Air
  • Has Heating: Yes
  • Laundry Features: In Basement
  • Sewer: Public Sewer
  • Utilities: For Gas Range
  • Water Source: Public

Frequently Asked Questions

How many bedrooms and bathrooms does this single-family home have?

There are 4 bedrooms and 2 bathrooms in this single-family home at 258 Cross Street.

What schools are nearby to 258 Cross Street?

Nearby schools include the Lynch Elementary School, Mccall Middle School, and Winchester High School.

Does this single-family home have parking?

Yes, there are 4 parking spaces available for 258 Cross Street.

What are the annual taxes for 258 Cross Street?

Annual taxes for this single-family home are estimated at $9,591.

How does 258 Cross Street compare to other single-family homes in Winchester Town Center?

This single-family home is listed 42% below the average price for single-family homes in Winchester Town Center and has been on the market for 4 less days than the typical home in this area.

What is the square footage on this single-family home?

According to the MLS, this listing is 1,719 sqft.

258 Cross Street is a 4-bedroom, 2-bath single-family home for sale in Winchester MA 01890. On Prevu for 38 days at $999,900. This home features 1,719 square feet of living space, located in Winchester Town Center. The median listing price for single-family homes in this area is $999,900. Nearby schools include Lynch Elementary School, Mccall Middle School, and Winchester High School. The home offers private outdoor space, dishwasher, air conditioning, parking, swimming pool, and washer/dryer. View other single-family home listings in Middlesex County.

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. 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, leasing or renting 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, leasing or renting. 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, or as to the accuracy of any of the Images, set forth herein.

Full MLS Disclaimers

Rebate estimate is indicative only and based on listing price and estimated buyer's agent commission paid by owner, if applicable. Final rebates are subject to Terms of Use and may vary due to final negotiated transaction terms.