$4,500
258 Cross Street # 0
Winchester, MA, 01890
–IMMEDIATELY AVAILABLE — A rare opportunity to rent a detached home in Winchester with the space, privacy and flexibility often missing from condo or townhome living. 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 4 bedrooms, 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. Pets negotiable. First month’s rent & security deposit due at lease signing. Lease term negotiable.
Property Details
Price:
$4,500
MLS #:
73590971
Status:
Active
Beds:
4
Baths:
2.5
Type:
Rental
Subtype:
Single Family Residence
Listed Date:
Oct 14, 2026
Finished Sq Ft:
1,719
Total Sq Ft:
1,719
Year Built:
1860
Schools
Interior
Above Grade Finished Area
1719
Appliances
Range, Dishwasher, Disposal, Microwave, Refrigerator, Freezer, Washer, Dryer
Bathrooms
2 Full Bathrooms, 1 Half Bathroom
Heating
Natural Gas
Laundry Features
In Building, In Unit
Exterior
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
Exterior Features
Patio, Storage, Fenced Yard, Garden
Fencing
Fenced
Open Parking Spaces
4
Parking Spots
4
Parking Total
4
Patio And Porch Features
Patio
Financial
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 Rental in Winchester as of Oct 17, 2026
38
Rental Listed
66
Avg DOM
3
Avg $ / SqFt
$4,128
Avg List Price
Community
- Address258 Cross Street # 0 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 # 0 Winchester MA is a Rental for sale in Winchester, MA, 01890. It is listed for $4,500 To schedule a showing of MLS#73590971 at 258 Cross Street # 0 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 # 0
Winchester, MA

























