Open House LogoIn-Person: 10/24 3:00 PM - 4:30 PM
$974,900
 $5,233 est/mo Sourced by Back At You

258 Cross St,Winchester, MA 01890

Winchester, MA 01890

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Description

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.

Details

MLS #73575764
Listing TypeFor Sale
StyleHouse
Sub-TypeResale
StatusActive
Year1860
Days On Site44
Listing Provided ByFiv Realty Co | Justin Blankenship

Features

Bed(s)3
Bath(s) 3 Total
SQ Feet1,719
BasementY
ZoningRG
Acreage0.18
Golf CourseYes

Interior

Rooms Total7
Cooling Yes / NoYes
CoolingCentral Air
Heating Yes / NoYes
HeatingCentral, Forced Air
Interior FeaturesInternet Available - Unknown
AppliancesGas Water Heater, Range, Dishwasher, Disposal, Microwave, Refrigerator, Freezer, Washer, Dryer
Fireplaces Total0
Fireplace Yes / NoNo
FlooringWood, Tile, Carpet, Hardwood

Exterior

Exterior FeaturesPatio, Storage, Professional Landscaping, Fenced Yard, Garden
RoofShingle
Construction MaterialsFrame
Foundation DetailsStone
Lot FeaturesCorner Lot, Level
FencingFenced/Enclosed, Fenced

Parking

Garage Yes / NoNo
Parking FeaturesOff Street, Deeded, Paved
Open Parking Yes / NoYes

Utilities

Utilitiesfor Gas Range
SewerPublic Sewer

Taxes

Tax Annual Amount9591.95
Tax Assessed Value865700
Tax Year2026

Location

Community FeaturesPublic 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 / NoNo

Area Information

StateMA
CountyMiddlesex
CityWinchester
Zip Code01890
AreaWinchester Highlands
School DistrictWinchester High School
Elementary SchoolLynch Elementary School
High SchoolWinchester High School
Listing VS Median (in 01890)
Price:
$974,900
low | high
Med:
$1,049,000
42.399220432865% of Average
sqft:
1,719
low | high
Med:
2,411
9.744037230948% of Average
$ / sqft:
$567
low | high
Med:
$435
73.28256322028% of Average
On site:
44
low | high
Med:
51
86.274509803922% of Average
Sourced by Back At You

Market Activity 01890

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Learn More About This Property

Open House
In-Person
10/24 3:00 PM - 4:30 PM
StateMA
CountyMiddlesex
CityWinchester
Zip Code01890
AreaWinchester Highlands
School DistrictWinchester High School
Elementary SchoolLynch Elementary School
High SchoolWinchester High School
Listing VS Median (in 01890)
Price:
$974,900
low | high
Med:
$1,049,000
42.399220432865% of Average
sqft:
1,719
low | high
Med:
2,411
9.744037230948% of Average
$ / sqft:
$567
low | high
Med:
$435
73.28256322028% of Average
On site:
44
low | high
Med:
51
86.274509803922% of Average
Sourced by Back At You
Nearby Listings (Within 1/2 mile)
Price: $731K - $1.218M
sqft: 1,000 - 2,000
Listing Updated: October 22, 2026 at 12:31:01 PM PDT