$974,900
258 Cross St
Winchester, MA, 01890
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.
Property Details
Price:
$974,900
MLS #:
73575764
Status:
Active
Beds:
3
Baths:
2.5
Type:
Single Family
Subtype:
Single Family Residence
Neighborhood:
winchesterhighlands
Listed Date:
Sep 10, 2026
Finished Sq Ft:
1,719
Total Sq Ft:
1,719
Lot Size:
7,700 sqft / 0.18 acres (approx)
Year Built:
1860
Schools
Elementary School:
Lynch Elementary School
Middle School:
Mccall Middle School
High School:
Winchester High School
Interior
Above Grade Finished Area
1719
Appliances
Gas Water Heater, Range, Dishwasher, Disposal, Microwave, Refrigerator, Freezer, Washer, Dryer
Bathrooms
2 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air
Flooring
Wood, Tile, Carpet, Hardwood
Heating
Central, Forced Air
Interior Features
Internet Available – Unknown
Laundry Features
In Basement
Exterior
Architectural Style
Colonial
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
Construction Materials
Frame
Exterior Features
Patio, Storage, Professional Landscaping, Fenced Yard, Garden
Fencing
Fenced/Enclosed, Fenced
Lot Features
Corner Lot, Level
Open Parking Spaces
4
Open Parking YN
1
Parking Features
Off Street, Deeded, Paved
Parking Spots
4
Parking Total
4
Patio And Porch Features
Patio
Roof
Shingle
Financial
Tax Year
2026
Taxes
$9,592
Marie Andrews is an award-winning, licensed real estate broker with licenses in Massachusetts and Florida. She has been selling real estate in the greater Boston area for over 20 years. Over the past two decades, Marie has worked for Century 21 Advanced Realty, building a reputation as a multi-million dollar producer. She has developed an extensive network of investors, lenders, and attorneys. Marie has a wide knowledge base on property management, Massachusetts real estate law, and building…
More About MarieMortgage Calculator
Map
Current real estate data for Single Family in Winchester as of Oct 26, 2026
65
Single Family Listed
66
Avg DOM
566
Avg $ / SqFt
$2,179,412
Avg List Price
Community
- Address258 Cross St Winchester MA
- CityWinchester
- CountyMiddlesex
- Zip Code01890
Subdivisions in Winchester
- Brooks / Parkhurst / Town Forest
- Cox Road / High St Extension neighborhood
- Flats
- Flats neighborhood
- Lakeview/Wedgemere~ Near downtown & Wedgemere train station
- Macdonald field neighborhood
- Middlesex / downtown
- Near town/ Pine St neighborhood
- Old Village/ West Side
- Rangeley Historical Estate
- The Flats
- Vinson-Owen School District.
- West Side
- Winning Farm
Similar Listings Nearby
Property Summary
- 258 Cross St Winchester MA is a Single Family for sale in Winchester, MA, 01890. It is listed for $974,900 and features 3 beds, 3 baths, and has approximately 1,719 square feet of living space, and was originally constructed in 1860. The current price per square foot is $567. The average price per square foot for Single Family listings in Winchester is $566. The average listing price for Single Family in Winchester is $2,179,412. To schedule a showing of MLS#73575764 at 258 Cross St in Winchester, MA, contact your Pegasus Realty LLC agent at 781-858-3505.
Courtesy of Hartley Realty Group. The property listing data and information 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 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 set forth herein.
258 Cross St
Winchester, MA




































