$999,900
258 Cross Street
Winchester, MA, 01890
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
Property Details
Price:
$999,900
MLS #:
73541288
Status:
Active
Beds:
4
Baths:
2
Type:
Single Family
Subtype:
Single Family Residence
Neighborhood:
winchesterhighlands
Listed Date:
Jun 24, 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
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 Jul 12, 2026
70
Single Family Listed
67
Avg DOM
542
Avg $ / SqFt
$2,029,207
Avg List Price
Community
- Address258 Cross Street 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 Street Winchester MA is a Single Family for sale in Winchester, MA, 01890. It is listed for $999,900 and features 4 beds, 2 baths, and has approximately 1,719 square feet of living space, and was originally constructed in 1860. The current price per square foot is $582. The average price per square foot for Single Family listings in Winchester is $542. The average listing price for Single Family in Winchester is $2,029,207. To schedule a showing of MLS#73541288 at 258 Cross Street 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 Street
Winchester, MA