For Sale
HotHot
Single family home for sale at 258 Cross St, Winchester, MA 01890 | MLS# 73575764 | Listing updated on 2026-10-15
Photo 1 of Single family home for sale at 258 Cross St, Winchester, MA 01890 | MLS# 73575764 | Listing updated on 2026-10-15
Photo 2 of Single family home for sale at 258 Cross St, Winchester, MA 01890 | MLS# 73575764 | Listing updated on 2026-10-15
Photo 3 of Single family home for sale at 258 Cross St, Winchester, MA 01890 | MLS# 73575764 | Listing updated on 2026-10-15
Photo 4 of Single family home for sale at 258 Cross St, Winchester, MA 01890 | MLS# 73575764 | Listing updated on 2026-10-15
30+
Beds Icon

Street View

$974,900

Monthly Est:$4,852

  • Beds Icon3 Beds
  • Beds Icon
    3 Baths
  • Beds Icon1,719sqft

258 Cross St, Winchester, MA 01890

$4,852/moEst:

Get Pre-Approved

  • Single Family Residence

  • Built in 1860

  • $-- HOA

  • 0.18 acre lot

  • $567/sq.ft

Description

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.

  • Houzeo last checked: 14 minutes ago
  • Listing updated: October 15, 2026 at 1:20 pm
  • Listing Provided by: Justin Blankenship (617) 918-7419 | Fiv Realty Co. (781) 365-1984
  • Source: MLS Property Information Network-MA | MLS#: 73575764 MLS Property Information Network-MA

Property Details

  • Status

    Active

  • Type

    Single Family Residence

  • No. of Stories

    -

  • County

    Middlesex County

  • City

    Winchester

  • Neighborhood

    --

  • Year Built

    1860

  • HOA Fees

    -

  • Finished Area

    1,719 sqft

  • Lot Size

    0.18 acre lot

  • Basement Area

    - sqft

  • MLS Name

    MLS Property Information Network

  • MLS Number

    73575764

  • MLS Status

    Active

  • Days on Market

    53

Continue Your Journey in App

Find your dream home, receive real-time updates, and many more!

Location

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 3

    Bathrooms: 3

Interior

  • Appliances

    Gas Water Heater, Range, Dishwasher, Disposal, Microwave, Refrigerator, Freezer, Washer, Dryer

  • Heating

    Central, Forced Air

  • Exterior Features

    Patio, Storage, Professional Landscaping, Fenced Yard, Garden

  • Cooling

    Central Air

  • Interior Features

    Internet Available Unknown

  • Flooring

    Wood, Tile, Carpet, Hardwood

  • Sewer

    Public Sewer

Construction

  • Year Built

    Year Built: 1860

  • Home type

    Single Family Residence

  • Construction Materials

    Frame

  • Architectural Style

    Colonial

  • Roof

    Shingle

  • Foundation Details

    Stone

Utilities & Energy

  • Parking Features

    Off Street, Deeded, Paved

  • Utilities

    For Gas Range

  • Water Source

    Public

  • Laundry Features

    In Basement

  • Basement

    Full, Concrete, Unfinished

Other Features

  • Disclosures

    Some Photos Have Been Adjusted Using Ai Technology. Please Park On River Street For Showings. Previously Prepared 2020 Conceptual Addition Plans Available For Review. Plans Are Historical Only And Have Not Been Verified As Currently Approved, Valid, Or Buildable. Buyer To Perform All Due Diligence.

  • 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

  • Lot Features

    Corner Lot, Level

  • Patio And Porch Features

    Patio

Price History

DateEventPrice

09/11/2026

Source: mls_logoMLS Property Information Network-MA #73541288

Listing Removed

$999,900

$582/sqft

06/24/2026

Source: mls_logoMLS Property Information Network-MA #73541288

Listed for Sale

$999,900 +64.59%

$582/sqft

01/25/2019

Source: mls_logoMLS Property Information Network-MA #72380664

Sold

$607,500 -6.54%

$353/sqft

01/25/2019

Source: mls_logoMLS Property Information Network-MA #72380664

Price Decreased

$649,999 -7.01%

$378/sqft

08/17/2018

Source: mls_logoMLS Property Information Network-MA #72357284

Listing Removed

$699,000

$407/sqft

Nearby Homes

Based on information provided to and compiled by MLS Property Information Network, Inc. covering through Nov 04, 2026, 12:45AM. 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 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 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, or as to the accuracy of any of the Images, set forth herein. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified. © 2026 MLS Property Information Network, Inc. All Rights Reserved.

Advertising Broker: Derek Greene | The Greene Realty Group

Skip to Main Content