OPEN SAT, 11AM TO 1PM

For sale

$974,900

Est. $6,113/mo —

•

1,719

sq ft

258 Cross St, Winchester, MA 01890

About this home

Looking for a quiet retreat, with a SIDE STREET DRIVEWAY, built in privacy but still connected to the urban hustle and bustle of Boston metro? A rare Winchester opportunity, has arrived, priced comfortably 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, 2.5 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. Owners JUST put in an unused half bathroom on the first floor PERFECT for entertaining and preserving the privacy of your 2nd floor bathrooms. 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. Minutes from the iconic, and picturesque downtown Winchester where you'll find quaint coffee shops, local boutiques, and even a Commuter rail stop! Quick entry to Boston, Burlington, and the surrounding metro Boston area via nearby I95, Rt2, Rt3. Like spending your free time outdoors? You are mere minutes from the Medford Fells, one of Greater Boston's greenest and most resident friendly (humans and dogs alike) stretches of nature. Smaller upstairs bathroom could be converted to a 1/2 bath with stackable laundry or a dedicated laundry room (SEE ATTACHED RENDERINGS). Some of the previously prepared conceptual expansion plans are in the photos, the rest are available for review upon request.

Single-familyProperty Type

1860Year Built

7,700 sq ftLot Size

$567Price/Sq.Ft.

4 spacesParking

Listed by Justin Blankenship • Fiv Realty Co

Listed by • Fiv Realty Co

Listing updated: Sep 11, 2026 at 03:58am

Redfin checked: a few seconds ago

•Source:MLS PIN #73575764

Redfin agents who toured

Corner lot with driveway access on a road with less traffic. Good ceiling height on the 1st level. Steep staircase to the 3rd level. Both bathrooms are on the 2nd level.
7 years ago• May not reflect the current state of the home
Travis Speck (R) B
Redfin Premier agent
In need of updating, but home appears to have solid bones.
7 years ago• May not reflect the current state of the home
Terence Egan
Redfin Associate agent
Home located close to the Woburn line, with drive way off of the quieter side street. Great, flat yard. The master bedroom and 2nd bedroom on the second floor are both very spacious. The stairs leading up the the third floor are a bit steep. Second...
8 years ago• May not reflect the current state of the home
Tara Williams
Redfin Associate agent

Payment calculator

$6,113 per month

Principal and interest$5,184

Property taxes

$799

HOA dues

Home insurance

$130

Utilities

Add

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Mortgage resources

See this home in person

Open houses

Saturday, Sep 12

11:00am - 1:00pm

Sunday, Sep 13

11:00am - 1:00pm

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Around this home

Schools

K - 12
Preschool & daycare

Lynch Elementary School

Public PreK-5 • Assigned • 0.8mi

9/10

McCall Middle School

Public 6-8 • Assigned • 1.1mi

9/10

Winchester High School

Public 9-12 • Assigned • 0.7mi

10/10

Provided by GreatSchools

About Woburn

Highlands

Woburn Highlands, located between Horn Pond and the Woburn Center historic district, is a residential and commuter-friendly Woburn neighborhood with leafy side streets and a classic New England streetscape. The neighborhood’s character concentrates around the Montvale Avenue and Main Street corridor, where small storefronts, corner eateries, and everyday errands create a steady street rhythm. Housing reads as a mix of mid-century capes, colonials, and tidy multifamily homes set behind mature trees. Horn Pond’s loop paths and water views shape the local pace, while nearby civic buildings and brick mill remnants hint at Woburn’s industrial roots. For culture and community touchstones, the Woburn Public Library, the Woburn Historical Society, and the Woburn Bowladrome anchor local routines.

Provided by Walk Score and Local Logic

Market insights

258 Cross St · $974,900

DAYS ON MARKET

The average home goes pending in 22 days.

SALE-TO-LIST

Most homes are selling 1% above list price.

LIST PRICE

Median sale price in this area is $919,982. (6% lower than this home)

PRICE DROP

18% of homes in this area have had a price drop in the past month.

Property details

Interior
Exterior
Finance

Interior features
Hardwood, wood and tile flooring throughout
Crown molding
Vestibule
Internet available
7 total rooms

Bedrooms
Primary bedroom on the second floor with ceiling fan, custom built closets, hardwood floors and picture window
Second bedroom on the second floor with hardwood floors, closet and picture window
Third bedroom on the third floor with hardwood floors, closet, picture window, attic access (remodeled)
Fourth bedroom on the third floor with wall-to-wall carpet, closet, picture window, attic access (remodeled)

Bathrooms
Two full bathrooms (remodeled) featuring stone/ceramic tile floors and upgraded countertops
Primary full bath with double vanity, tub and shower, soaking tub, upgraded cabinets, bidet and overhead lighting
Second full bath with tub, pedestal sink and overhead lighting
One half bathroom on the first floor

Kitchen
Remodeled kitchen with stone/granite countertops and upgraded cabinets
Stainless steel appliances
Gas stove
Recessed lighting and ceiling fan
Exterior access from kitchen

Laundry & utility
Washer and dryer included
Laundry located in the basement
Gas water heater

Flooring
Hardwood
Wood
Tile
Carpet

Heating & cooling
Central heating (forced air)
Central air conditioning

Sale and tax history for 258 Cross St

Sale History
Tax History

Date

Event

Price

MLS PIN #73575764

Sep 10, 2026

Listed

$974,900

$567/sq ft

MLS PIN #72585005

Jun 1, 2020

Sold

$699,000

$407/sq ft

Apr 9, 2020

Pending

—

Mar 26, 2020

Contingent

—

Dec 5, 2019

Price Changed

$699,000

$407/sq ft

Oct 25, 2019

Listed

$745,000

$433/sq ft

+25

AMAZING PRICE for this home with expansion potential located on the corner of River Street with huge yard, driveway access on the side road...Move right in and enjoy this quaint home with high ceilings and spacious rooms! Situated nicely on a large corner lot with great expansion potential! Sunny kitchen formal dining room, living room with original detail , large master, second floor laundry finished third floor With 2 more rooms - home is in great condition and awaiting its new owners! Easy access to downtown shopping and schools - please call for a private viewing!

MLS PIN #72380664

Jan 25, 2019

Sold

$607,500

$353/sq ft

Nov 28, 2018

Pending

—

Oct 31, 2018

Price Changed

$649,999

$378/sq ft

Oct 1, 2018

Relisted

—

Sep 30, 2018

Price Changed

$679,000

$395/sq ft

Sep 30, 2018

Listing Removed

—

Aug 17, 2018

Listed

$699,000

$407/sq ft

+22

Great opportunity to own in Winchester. This four bedroom two full bath Victorian is situated on a corner lot and offers possible expansion opportunities. The living room's high ceilings and large windows offer a sunny spot to relax or entertain. The second floor offers two full baths, a linen closet with laundry, and two bedrooms, including a spacious master with large closet. The third floor has two more bedrooms, and a large storage space.The basement offers plenty of storage space and a walk-out to spacious, fenced yard. There is also large side yard, perfect for outdoor games. Replacement windows throughout, central air, irrigation system. The 2,600 acre Middlesex Fells reservation is close by, known for walking, running & biking trails. Easy distance to Lynch Elementary School, McCall Middle & WHS, center of Winchester, library, restaurants, commuter rail, minutes to downtown Boston on Rt 93.

MLS PIN #70038174

Aug 10, 2004

Sold

$462,500

$269/sq ft

Jun 29, 2004

Listing Removed

—

May 21, 2004

Listed

$475,000

$276/sq ft

Public Records

Nov 24, 1998

Sold

$279,900

$163/sq ft

MLS PIN #50282837

Sep 21, 1995

Sold

$150,000

$87/sq ft

Jun 9, 1995

Listing Removed

—

May 2, 1995

Listed

$159,900

$93/sq ft

Year

Property tax

Land + Additions

Assessment*

2025

$9,148 (+4.8%)

$502,200 + $322,700

$824,900

2023

$8,725 (+4.3%)

$502,200 + $305,500

$807,700

2022

$8,362 (+1.1%)

$376,700 + $291,700

$668,400

2021

$8,273 (+2.7%)

$353,100 + $291,700

$644,800

2020

$8,054 (+7.3%)

$353,100 + $296,900

$650,000

2019

$7,508 (+0.3%)

$255,000 + $365,000

$620,000

2018

$7,482 (+4.4%)

$248,800 + $365,000

$613,800

2017

$7,169 (+9.3%)

$248,800 + $335,000

$583,800

2016

$6,562 (+0.3%)

$248,800 + $313,000

$561,800

2015

$6,543 (+6.9%)

$226,000 + $313,000

$539,000

2014

$6,120 (+9.9%)

$188,300 + $295,100

$483,400

2013

$5,568 (+1.8%)

$156,900 + $279,100

$436,000

2012

$5,472 (+3.7%)

$156,900 + $279,100

$436,000

2011

$5,276 (+5.6%)

$156,900 + $279,100

$436,000

2010

$4,998 (+2.1%)

$156,500 + $277,700

$434,200

2009

$4,893

$156,500 + $277,700

$434,200

Public record

Beds

Baths

Stories

Lot width

—

Lot depth

—

Lot size

7,841 Sq. Ft.

Year renovated

—

Finished Sq. Ft.

1,719

Unfinished Sq. Ft.

—

Total Sq. Ft.

1,719

Year built

1860

Style

Single Family Residential

County

Middlesex County

APN

3628703S

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Sep 11, 2026.

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

2/10 Fire Factor

0.00% chance of being in a wildfire in next 30 years

5/10 Heat Factor

7 days above 96° expected this year, 15 days in 30 years

6/10 Wind Factor

54% chance of strong winds in next 30 years

3/10 Air Factor

2 unhealthy days expected this year, 3 days in 30 years

Provided by First Street

Historical weather

Winchester, MA • 01890

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

89/ 100

Very good sunlight

Sunscore

This home ranks in the top 28% for direct sun exposure in the zip code. There appears to be minimal shading by surrounding buildings, terrain, and vegetation.

8.2 hrs

5.1 hrs

JuneDecember

Provided by Shadowmap

Redfin Estimate for 258 Cross St

$1,000,243

$25K over list price of $975K

Nearby comparable homes

The Redfin Estimate uses 6 recent nearby sales, priced between $730K to $1.1M.

SOLD SEP 1, 2026
$784,500 Last sold price
3 beds2 baths2,212 sq ft
24 Carter St, Woburn, MA 01801
$212/sq ft
107 years newer
SOLD JUL 14, 2026
$730,000 Last sold price
4 beds2 baths1,658 sq ft
4 Spring Ct, Woburn, MA 01801
$127/sq ft
smaller lot
100 years newer
SOLD SEP 26, 2025
$878,000 Last sold price
3 beds1.5 baths1,672 sq ft
17 Baldwin St, Winchester, MA 01890
$42/sq ft
larger lot
30 years newer
SOLD MAY 28, 2026
$1,100,000 Last sold price
3 beds1.5 baths1,675 sq ft
104 Wendell St, Winchester, MA 01890
$90/sq ft
91 years newer
SOLD MAR 20, 2026
$1,015,000 Last sold price
3 beds1.5 baths1,749 sq ft
320 Washington St, Winchester, MA 01890
$13/sq ft
smaller lot
10 years older
SOLD APR 23, 2026
$780,000 Last sold price
2 beds2 baths1,824 sq ft
2 Maria Ct, Woburn, MA 01801
$139/sq ft
larger lot
94 years newer

Rental earnings

Est. $4,163 per month, based on comparable rentals

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