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ActiveListed 39 days ago

$974,900

258 Cross St, Winchester, MA 01890

3
beds
2.5
baths
1,719
sqft
Lot sizeThe land that comes with the home, as reported to the MLS.
7,700 sqft
Year builtThe year the building was originally built, as reported by the listing agent.
1860
On the marketDays since the home was listed. New listings tend to move fastest.
39 days ago
Property type
Single Family Residence
Price per sqftList price divided by interior living area — handy for comparing homes of different sizes.
$567
ParkingSpaces that come with the home, as reported to the MLS.
4 spaces
Annual taxesLast annual property tax bill reported to the MLS. A new owner's bill can differ.
$9,592

What’s Special

  • Central Air
  • Patio
  • Fenced Yard
  • In Basement

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.

Listing courtesy of Justin Blankenship, Fiv Realty Co · MLS PIN #73575764

Facts & Features

Status
Active
Active status flag
Active
Bedrooms
3
Bathrooms
2 full, 1 half
Living area
1,719 sqft

Interior

1
  • Internet Available - Unknown

Exterior

5
  • Patio
  • Storage
  • Professional Landscaping
  • Fenced Yard
  • Garden

Parking

3
  • Off Street
  • Deeded
  • Paved

Laundry

1
  • In Basement

Heating

2
  • Central
  • Forced Air

Cooling

1
  • Central Air

Appliances

9
  • Gas Water Heater
  • Range
  • Dishwasher
  • Disposal
  • Microwave
  • Refrigerator
  • Freezer
  • Washer
  • Dryer

MLS PIN #73575764 · Listed September 10, 2026

Location

258 Cross St, Winchester · All Winchester homes

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.

$974,900

258 Cross St

96 Loring Ave1 / 29
Active

$919,999

4 bd · 2 ba · 2,326 sqft · Single Family

96 Loring Ave

Winchester, MA 01890

Listing courtesy of Jeremy Smith, StartPoint Realty · MLS PIN #73561829

17 Russell Rd1 / 25
Active

$1,098,000

3 bd · 1.5 ba · 1,657 sqft · Single Family

17 Russell Rd

Winchester, MA 01890

Listing courtesy of Tsz Mui Kwan, Kwan Realty Inc. · MLS PIN #73566405

24 Richardson St1 / 40
Active

$1,069,000

4 bd · 2.5 ba · 2,411 sqft · Single Family

24 Richardson St

Winchester, MA 01890

Listing courtesy of Andersen Group Realty, Keller Williams Realty Boston Northwest · MLS PIN #73571480

15 Clark St1 / 22
Active

$799,000

3 bd · 1.5 ba · 1,340 sqft · Single Family

15 Clark St

Winchester, MA 01890

Listing courtesy of Jeffrey Hsu, Coldwell Banker Realty - Milton · MLS PIN #73555218

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.