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257 Cross StWinchester, MA 01890

For Sale

$1,099,000

Smart Buyer Rebate $5,495

Exceptional two-family opportunity with incredible potential to renovate/expand! Situated on a large, level corner lot with frontage on both Cross Street and Verplast Avenue, this property offers endless possibilities for investors, builders, or owner-occupants. The first-floor unit features a fireplaced living room, an updated kitchen, three bedrooms, 1.5 baths and sunroom overlooking the expansive backyard. The second unit offers a spacious and flexible layout with a living room, kitchen, 2 bedrooms, laundry room and full bath. The generous lot, separate entrances, and existing footprint create an ideal opportunity to modernize the current two-family, expand the living space, or explore redevelopment possibilities. Whether you're looking for a strong income property or your next renovation project, this property is full of potential and ready for its next chapter!

Listed by Kim Covino

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Compass

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781-249-3854

Listed by Kim Covino & Co. Team

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Compass

Last updated July 31, 2026

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Source: MLSPin #73553083

Listing Facts

  • TypeMulti-family
  • NeighborhoodWinchester Town Center
  • Bedrooms5
  • Bathrooms3
  • Days on Prevu11
  • Taxes$9,849/year
  • Size2,801 sqft
  • Price per sqft$392

Amenities

  • Private Outdoor Space
  • Air Conditioning
  • Parking

Location

Mortgage Calculator

Listing History

07/21/2026
Listed by Compass
$1,099,000

Property Details for 257 Cross St

Association

Amenities

  • Community Features: Public Transportation, Shopping, Tennis Court(s), Park, Walk/Jog Trails, Golf, Medical Facility, Highway Access, Public School, T-Station

Exterior

Construction

  • Number Of Units Total: 2
  • Roof: Shingle
  • Stories: 2
  • Stories Total: 2
  • Year Built: 1960
  • Year Built Details: Actual

Features

  • Patio And Porch Features: Patio

Measurements

  • Building Area Total: 2,801
  • Building Area Units: Square Feet
  • Lot Features: Corner Lot, Level
  • Lot Size Acres: 0.24
  • Lot Size Area: 0
  • Lot Size Square Feet: 10,367
  • Lot Size Units: Acres

Financial

Taxes

  • Parcel Number: M:013 B:0137 L:0,898030
  • Tax Annual Amount: $9,849.00
  • Tax Assessed Value: $888,100.00
  • Tax Year: 2025

Interior

Features

  • Fireplace: Yes
  • Fireplaces Total: 3
  • Interior Features: Living Room, Kitchen, Laundry Room, Sunroom

Measurements

  • Living Area: 2,801
  • Living Area Source: Public Record

Rooms

  • Basement: Full, Finished, Walk-Out Access
  • Bathrooms Full: 2
  • Bathrooms Half: 1
  • Bathrooms Total Integer: 3
  • Bedrooms Total: 5
  • Rooms Total: 11

Parking

Parking

  • Open Parking Spaces: 4
  • Parking Total: 4

Schools

Elementary School

  • Elementary School: Lynch

High School

  • High School: Whs

Middle or Junior School

  • Middle Or Junior School: Mccall

Utilities

Equipment

  • Cooling: Central Air
  • Has Cooling: Yes
  • Heating: Oil
  • Has Heating: Yes
  • Sewer: Public Sewer
  • Water Source: Public

Frequently Asked Questions

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

There are 5 bedrooms and 3 bathrooms in this multi-family home at 257 Cross St.

What schools are nearby to 257 Cross St?

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

Does this multi-family home have parking?

Yes, there are 4 parking spaces available for 257 Cross St.

What are the annual taxes for 257 Cross St?

Annual taxes for this multi-family home are estimated at $9,849.

How does 257 Cross St compare to other multi-family homes in Winchester Town Center?

This multi-family home is listed 27% below the average price for multi-family homes in Winchester Town Center and has been on the market for 31 less days than the typical home in this area.

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

According to the MLS, this listing is 2,801 sqft.

257 Cross St is a 5-bedroom, 3-bath multi-family home for sale in Winchester MA 01890. On Prevu for 11 days at $1,099,000. This residence features 2,801 square feet of living space, located in Winchester Town Center. The median listing price for multi-family homes in this area is $999,900. Nearby schools include Lynch Elementary School, Mccall Middle School, and Whs High School. Property amenities include private outdoor space, air conditioning, and parking. Browse more multi-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.