258 Cross St · Winchester

FOR SALE · MLS #73575764

$974,900

beds
3
baths
2.5
sqft
1,719

258 Cross St

Winchester, MA 01890

LOCATION

Property location

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258 Cross St, Winchester, MA 01890Open Street View

GPS

Home type
Single Family Residence
Interior living area
1,719 sqft
Year built
1860
Lot size
7,700 sqft (about 0.18 acres)
Parking spaces
4
Price per sqft
$567/sqft

About this home

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.

Listed by Justin Blankenship · Fiv Realty Co
MLS PIN #73575764 · Updated 10/15/2026, 9:20:00 AM ET

Facts & features

Home overview
Property subtype
Single Family Residence
Property category
Residential
MLS status
Active
Bedrooms
3
Full bathrooms
2
Half bathrooms
1
Total bathrooms
2.5
Total rooms
7
Living area
1,719 sqft
Living area source
Public Record
Above grade finished area
1,719 sqft
Building area
1,719
Building area units
Square Feet
Building area source
Public Records
Area includes basement
No
Area disclosures
All measurements provided are for marketing purposes only. Buyer(s) to perform their due diligence
Interior & systems
Heating
Central · Forced Air
Heating available
Yes
Heating zones
1
Cooling
Central Air
Cooling available
Yes
Cooling zones
1
Appliances
Gas Water Heater · Range · Dishwasher · Disposal · Microwave · Refrigerator · Freezer · Washer · Dryer
Flooring
Wood · Tile · Carpet · Hardwood
Interior features
Internet Available - Unknown
Laundry
In Basement
Basement
Full · Concrete · Unfinished
Fireplace
No
Fireplaces
0
Room details

Primary bedroom

Level
Second
Area
244.38 sqft
Length
17.25 ft
Width
14.17 ft
Features
Ceiling Fan(s) · Closet/Cabinets - Custom Built · Flooring - Hardwood · Window(s) - Picture · Cable Hookup · High Speed Internet Hookup

Bedroom 2

Level
Second
Area
161.21 sqft
Length
13.25 ft
Width
12.17 ft
Features
Closet · Flooring - Hardwood · Window(s) - Picture · Cable Hookup · High Speed Internet Hookup · Lighting - Overhead

Bedroom 3

Level
Third
Area
149.81 sqft
Length
11.75 ft
Width
12.75 ft
Features
Closet · Flooring - Hardwood · Window(s) - Picture · Attic Access · Remodeled

Bedroom 4

Level
Third
Area
143.94 sqft
Length
11.75 ft
Width
12.25 ft
Features
Closet · Flooring - Wall to Wall Carpet · Window(s) - Picture · Attic Access · Remodeled

Living room

Level
Main,First
Area
238.89 sqft
Length
13.33 ft
Width
17.92 ft
Features
Flooring - Hardwood · Window(s) - Bay/Bow/Box · Cable Hookup · High Speed Internet Hookup · Lighting - Overhead · Crown Molding · Vestibule

Dining room

Level
Main,First
Area
185.01 sqft
Length
12.83 ft
Width
14.42 ft
Features
Flooring - Hardwood · Window(s) - Picture · Lighting - Pendant · Crown Molding

Kitchen

Level
Main,First
Area
205.83 sqft
Length
13 ft
Width
15.83 ft
Features
Ceiling Fan(s) · Flooring - Stone/Ceramic Tile · Window(s) - Picture · Countertops - Stone/Granite/Solid · Cabinets - Upgraded · Exterior Access · Recessed Lighting · Remodeled · Stainless Steel Appliances · Gas Stove · Vestibule

Bathroom 1

Level
Second
Area
80.24 sqft
Length
9.08 ft
Width
8.83 ft
Features
Bathroom - Full · Bathroom - Double Vanity/Sink · Bathroom - With Tub & Shower · Flooring - Stone/Ceramic Tile · Window(s) - Picture · Countertops - Stone/Granite/Solid · Countertops - Upgraded · Bidet · Cabinets - Upgraded · Remodeled · Lighting - Overhead · Soaking Tub

Bathroom 2

Level
Second
Area
30.38 sqft
Length
6.75 ft
Width
4.5 ft
Features
Bathroom - Full · Bathroom - With Tub · Flooring - Stone/Ceramic Tile · Window(s) - Picture · Remodeled · Lighting - Overhead · Pedestal Sink · Soaking Tub

Bathroom 3

Level
First
Area
20 sqft
Length
5 ft
Width
4 ft
Features
Bathroom - Half

Price & tax details

Current asking price$974,900
Original asking price$974,900
Listed on2026-09-10
Days on market35
Tax record supplied by MLS
YearProperty taxAssessed value
2026$9,591.95$865,700

These records are supplied by the current listing. Assessed value is not market value; confirm taxes with the local assessor.

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SCHOOLS & EDUCATION

Schools & performance

2026 MA DESE

School names, grades and state-reported measures are listed below.

Schools named in the listing

93DESE percentile

MLS-listed elementary

Lynch Elementary

Grades PK · K · 1 · 2 · 3 · 4 · 5

Progress toward targets 78%

95DESE percentile

MLS-listed middle

McCall Middle

Grades 6 · 7 · 8

Progress toward targets 86%

97DESE percentile

MLS-listed high school

Winchester High School

Grades 9 · 10 · 11 · 12

Progress toward targets 88%

MLS school names do not guarantee attendance. Assignment can vary by school year, grade and admissions policy; confirm with the district before committing.
What do these numbers mean?

DESE accountability percentiles (1–99) compare schools administering similar assessments, using up to two years of indicators. These are not test scores out of 100 or GreatSchools 1–10 ratings. Progress toward targets is a separate state measure. Consider programs, support services and your child’s needs as well.

School names link to available school or district websites.

Information is deemed reliable but is not guaranteed. © 2026 MLS Property Information Network, Inc. All rights reserved.

Listings updated