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

258 Cross Street, Winchester, MA

Winchester Highlands, Winchester Single Family Get directions

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

A rare Winchester opportunity 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 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. 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. Previously prepared conceptual expansion plans are available for review. Minutes from the iconic, and picturesque downtown. Rear vestibule is the perfect place for a 1st floor half bath (see attached rendering). Smaller upstairs bathroom could be converted to a 1/2 bath with stackable laundry or a dedicated laundry room (SEE ATTACHED RENDERINGS).

Additional Details
Status: ACT
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...

$999,900

  • Listing ID: 73541288
  • Bedrooms: 4
  • Full Baths: 2
  • 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?