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258 Cross StWinchester, MA 01890

For Sale

$974,900

Smart Buyer Rebate $4,875

Are rates making you feel like home buying is out of reach? The sellers are now offering A TWENTY THOUSAND DOLLAR ($20,000) CREDIT, PERFECT to put towards closing costs or a 2/1 rate buy down. Enjoy over a ONE THOUSAND ($1000) DOLLAR PER MONTH savings year one and over a FIVE HUNDRED ($500) DOLLAR PER MONTH savings year two. A rare opportunity to own a detached home in Winchester under $1M—with the space, privacy and flexibility often missing from condo or townhome living. Tired of or can't imagine paying an HOA fee on top of fighting rising interest rates? Skip the added cost, lock in (REFI LATER) a lower monthly payment, and get more value at 258 Cross Street! The property is set on a level, fenced corner lot with a side-street driveway, ACCESSIBLE FROM RIVER STREET, parking for 4 cars, and offering 3 bedrooms, a versatile bonus room (4 beds on public record), 2.5 baths and a layout that can adapt as your needs change. The main level blends classic character with everyday function, featuring hardwood floors, crown molding, arched openings, bay windows and an updated eat-in kitchen with stone counters, upgraded cabinetry, stainless appliances and gas cooking. A brand-new first-floor powder room adds convenience for everyday living and entertaining. Upstairs, two generously sized bedrooms are joined by two updated full baths, including a larger bath with double vanity, tiled shower and soaking tub. The finished third floor provides a third bedroom plus an additional flex space ideal for a home office, fitness room, playroom, hobby space or guests. Major recent improvements, besides the unused, first floor half bath, include brand-new central AC and a newly sodded yard. Current owners have also invested considerably into improvements from the kitchen (countertops/appliances/backsplash/flooring), to the main bathroom remodel on the 2nd floor, and even a rebuilding of the lower two staircases to increase functionality. Outside, enjoy a fenced backyard, patio, storage shed and rare off-street parking for four vehicles. The full basement provides additional laundry and storage space. Convenient to Winchester Center, local shops and dining, the commuter rail, the Middlesex Fells and major routes connecting Boston, Cambridge, Burlington and the surrounding metro area. Previously prepared conceptual expansion plans are available for buyers interested in exploring future possibilities.

Listed by Justin Blankenship

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Fiv Realty Co

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6179187419

Last updated October 15, 2026

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Source: MLSPin #73575764

Listing Facts

  • TypeSingle-family
  • NeighborhoodWinchester Town Center
  • Bedrooms3
  • Bathrooms3
  • Days on Prevu50
  • Taxes$9,591.95/year
  • Size1,719 sqft
  • Price per sqft$567

Amenities

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

Location

Mortgage Calculator

Listing History

09/11/2026
Listed by Fiv Realty Co
$974,900
  1. 09/11/2026$974,900
    Listed by Fiv Realty Co

Property Details for 258 Cross St

Association

Amenities

  • Community Features: Pool, Tennis Court(s), Park, Stable(s), Golf, Sidewalks

Exterior

Construction

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

Features

  • Fencing: Fenced
  • Other Structures: Storage
  • Patio And Porch Features: Patio

Measurements

  • Building Area Total: 1,719
  • Building Area Units: Square Feet
  • Lot Features: Corner Lot, Level, Landscaped
  • 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: Crown Molding

Measurements

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

Rooms

  • Basement: Full, Concrete, Unfinished
  • Has Basement: Yes
  • Bathrooms Full: 2
  • Bathrooms Half: 1
  • Bathrooms Total Integer: 3
  • Bedrooms Total: 3
  • Rooms Total: 7

Other

General

  • Exclusions: 1/2 Bathroom Mirror

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
  • Water Source: Public

Frequently Asked Questions

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

There are 3 bedrooms and 3 bathrooms in this single-family home at 258 Cross St.

What schools are nearby to 258 Cross St?

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 St.

What are the annual taxes for 258 Cross St?

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

How does 258 Cross St 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 44 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 St is a 3-bedroom, 3-bath single-family home for sale in Winchester MA 01890. On Prevu for 50 days at $974,900. This residence 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 $919,999. Nearby schools include Lynch Elementary School, Mccall Middle School, and Winchester High School. Additional amenities include private outdoor space, dishwasher, air conditioning, parking, swimming pool, and washer/dryer. Browse more 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.