In-Person: 10/24 3:00 PM - 4:30 PMAre 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.
| MLS # | 73575764 |
|---|---|
| Listing Type | For Sale |
| Style | House |
| Sub-Type | Resale |
| Status | Active |
| Year | 1860 |
| Days On Site | 44 |
| Listing Provided By | Fiv Realty Co | Justin Blankenship |
| Bed(s) | 3 |
|---|---|
| Bath(s) | 3 Total |
| SQ Feet | 1,719 |
| Basement | Y |
| Zoning | RG |
| Acreage | 0.18 |
| Golf Course | Yes |
| Rooms Total | 7 |
|---|---|
| Cooling Yes / No | Yes |
| Cooling | Central Air |
| Heating Yes / No | Yes |
| Heating | Central, Forced Air |
| Interior Features | Internet Available - Unknown |
| Appliances | Gas Water Heater, Range, Dishwasher, Disposal, Microwave, Refrigerator, Freezer, Washer, Dryer |
| Fireplaces Total | 0 |
| Fireplace Yes / No | No |
| Flooring | Wood, Tile, Carpet, Hardwood |
| Exterior Features | Patio, Storage, Professional Landscaping, Fenced Yard, Garden |
|---|---|
| Roof | Shingle |
| Construction Materials | Frame |
| Foundation Details | Stone |
| Lot Features | Corner Lot, Level |
| Fencing | Fenced/Enclosed, Fenced |
| Garage Yes / No | No |
|---|---|
| Parking Features | Off Street, Deeded, Paved |
| Open Parking Yes / No | Yes |
| Utilities | for Gas Range |
|---|---|
| Sewer | Public Sewer |
| Tax Annual Amount | 9591.95 |
|---|---|
| Tax Assessed Value | 865700 |
| Tax Year | 2026 |
| 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 |
|---|---|
| Senior Community Yes / No | No |
| State | MA |
|---|---|
| County | Middlesex |
| City | Winchester |
| Zip Code | 01890 |
| Area | Winchester Highlands |
| School District | Winchester High School |
| Elementary School | Lynch Elementary School |
| High School | Winchester High School |
| Listing VS Median (in 01890) | |
Price: $974,900 low | high Med: $1,049,000 sqft: 1,719 low | high Med: 2,411 $ / sqft: $567 low | high Med: $435 On site: 44 low | high Med: 51 | |
| Open House |
|---|
| In-Person 10/24 3:00 PM - 4:30 PM |
| State | MA |
|---|---|
| County | Middlesex |
| City | Winchester |
| Zip Code | 01890 |
| Area | Winchester Highlands |
| School District | Winchester High School |
| Elementary School | Lynch Elementary School |
| High School | Winchester High School |
| Listing VS Median (in 01890) | |
Price: $974,900 low | high Med: $1,049,000 sqft: 1,719 low | high Med: 2,411 $ / sqft: $567 low | high Med: $435 On site: 44 low | high Med: 51 | |
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