LRG: Luxury Residential Group
  • Login  /
  • 355 Boylston St
  • (617) 233-5800
Redefining Boston Real Estate

258 Cross St, Winchester, MA

Winchester Highlands, Winchester Single Family Get directions

Click for Search Results
258 Cross St, Winchester, MA Photo #1
258 Cross St, Winchester, MA Photo #2
258 Cross St, Winchester, MA Photo #3
258 Cross St, Winchester, MA Photo #4
258 Cross St, Winchester, MA Photo #5
258 Cross St, Winchester, MA Photo #6
258 Cross St, Winchester, MA Photo #7
258 Cross St, Winchester, MA Photo #8
258 Cross St, Winchester, MA Photo #9
258 Cross St, Winchester, MA Photo #10
258 Cross St, Winchester, MA Photo #11
258 Cross St, Winchester, MA Photo #12
258 Cross St, Winchester, MA Photo #13
258 Cross St, Winchester, MA Photo #14
258 Cross St, Winchester, MA Photo #15
258 Cross St, Winchester, MA Photo #16
258 Cross St, Winchester, MA Photo #17
258 Cross St, Winchester, MA Photo #18
258 Cross St, Winchester, MA Photo #19
258 Cross St, Winchester, MA Photo #20
258 Cross St, Winchester, MA Photo #21
258 Cross St, Winchester, MA Photo #22
258 Cross St, Winchester, MA Photo #23
258 Cross St, Winchester, MA Photo #24
258 Cross St, Winchester, MA Photo #25
258 Cross St, Winchester, MA Photo #26
258 Cross St, Winchester, MA Photo #27
258 Cross St, Winchester, MA Photo #28
258 Cross St, Winchester, MA Photo #29
258 Cross St, Winchester, MA Photo #30
258 Cross St, Winchester, MA Photo #31
258 Cross St, Winchester, MA Photo #32
258 Cross St, Winchester, MA Photo #33
258 Cross St, Winchester, MA Photo #34
258 Cross St, Winchester, MA Photo #35
258 Cross St, Winchester, MA Photo #36
258 Cross St, Winchester, MA Photo #37
258 Cross St, Winchester, MA Photo #38
258 Cross St, Winchester, MA Photo #39
Previous Photo Next Photo

Image 1 of 39

previous
  • Photo #1
  • Photo #2
  • Photo #3
  • Photo #4
  • Photo #5
  • Photo #6
  • Photo #7
  • Photo #8
  • Photo #9
  • Photo #10
  • Photo #11
  • Photo #12
  • Photo #13
  • Photo #14
  • Photo #15
  • Photo #16
  • Photo #17
  • Photo #18
  • Photo #19
  • Photo #20
  • Photo #21
  • Photo #22
  • Photo #23
  • Photo #24
  • Photo #25
  • Photo #26
  • Photo #27
  • Photo #28
  • Photo #29
  • Photo #30
  • Photo #31
  • Photo #32
  • Photo #33
  • Photo #34
  • Photo #35
  • Photo #36
  • Photo #37
  • Photo #38
  • Photo #39
next

Unit Information

Looking for a quiet retreat, with a SIDE STREET DRIVEWAY, built in privacy but still connected to the urban hustle and bustle of Boston metro? A rare Winchester opportunity, has arrived, priced comfortably 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, 2.5 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. Owners JUST put in an unused half bathroom on the first floor PERFECT for entertaining and preserving the privacy of your 2nd floor bathrooms. 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. Minutes from the iconic, and picturesque downtown Winchester where you'll find quaint coffee shops, local boutiques, and even a Commuter rail stop! Quick entry to Boston, Burlington, and the surrounding metro Boston area via nearby I95, Rt2, Rt3. Like spending your free time outdoors? You are mere minutes from the Medford Fells, one of Greater Boston's greenest and most resident friendly (humans and dogs alike) stretches of nature. Smaller upstairs bathroom could be converted to a 1/2 bath with stackable laundry or a dedicated laundry room (SEE ATTACHED RENDERINGS). Some of the previously prepared conceptual expansion plans are in the photos, the rest are available for review upon request.

Additional Details
Status: NEW
Type: Single Family, Single Family Residence
Area: Winchester Highlands
Zip Code: 01890
Parking
Garage Capacity: 4
Parking: Off Street,Deeded,Paved
Parking Spaces: 4
Rooms and Dimensions
Total Rooms: 7
Has Basement: Yes
Login to view all MLS information
 

Loading...

$974,900

  • Status: New
  • Listing ID: 73575764
  • Bedrooms: 4
  • Full Baths: 2
  • Half Baths: 1
  • Living Area: 1,719 sqft Convert
  • Lot Size: 7,700 sqft Convert
  • Acres: 0.18

  • View description
Inquire About This Listing
Luxury Residential Group

Luxury Residential Group

(617) 233-5800

Receive more info or arrange a tour

When you are ready, please contact us and we will put our unrivaled knowledge of the Boston real estate market to work for you. Whether you are buying a luxury condo or renting a luxury apartment, we pledge to make your experience as stress free and enjoyable as possible.

Please call, email, or send us a message through the web form below. An LRG Real Estate agent will contact you promptly.

  • reset
 
Content © 2026 MLS Property Information Network, Inc. The information in this listing was gathered from third party resources including the seller and public records. Listing information provided courtesy of Justin Blankenship of Fiv Realty Co. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations or warranties as to the accuracy of this information.

close x
Forgot password?