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About this home
MASSIVE PRICE IMPROVEMENT!!! 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 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 bedrooms 3 and 4 that allow you to expand your work and life styles, as your life changes, without needing to move. The bedrooms work well as kids rooms, guest suites, home office / gym, hobby spaces or all of the above! 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.
Make a winning offer with the help of a local agent
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
Offer insights
258 Cross St · $919,000
$918K and above
75% chance or better to win
Why $918K+ is a strong offer
DAYS ON MARKET
63 days
The average home goes pending in 23 days.
SALE-TO-LIST
100.6%
Most homes are selling 1% above list price.
About offer insights
Property details
Interior
Exterior
Finance
Kitchen
Bathroom
Bedroom
Living
Dining
Interior features
Custom-built closet cabinetry
Ceiling fans
Picture windows
Bay/bow/box window
Crown molding
Vestibule
Cable and high-speed internet hookups
Bedrooms
4 bedrooms: 2 on the second floor and 2 on the third floor
Bathrooms
2 full bathrooms and 1 half bathroom
Remodeled full bathroom with double vanity, tub and shower, soaking tub, bidet, upgraded cabinets, and upgraded stone counters
Remodeled full bathroom with tub, soaking tub, and pedestal sink
Kitchen
Remodeled kitchen with upgraded cabinets, stone counters, recessed lighting, and stainless steel appliances
Gas stove, range, dishwasher, disposal, microwave, refrigerator, and freezer
Laundry & utility
Washer and dryer
Laundry in basement
Gas water heater
Flooring
Hardwood, wood, tile, and carpet
Heating & cooling
Central forced-air heating
Central air conditioning
Exterior features
Patio
Storage
Professionally landscaped garden
Fenced yard
Level corner lot
Paved public road
Home design
Single-family residence
Parking
4 off-street deeded parking spaces
Paved parking
Construction
Frame construction
Stone foundation
Shingle roof
Gray exterior
Utilities
Public water
Public sewer
HOA & community
Nearby public transportation, shopping, pool, tennis courts, parks, walking and jogging trails, stables, golf, medical facilities, bike paths, conservation areas, highway access, places of worship, private and public schools, T-station, university, and sidewalks
Electricity and solar
View estimated energy costs and solar savings for this home
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*
2026
$9,592 (+4.9%)
$533,600 + $332,100
$865,700
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
4
Baths
2
Stories
2
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 16, 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)
34
20
36
21
51
32
60
40
69
51
80
61
84
66
80
60
75
56
63
46
53
36
39
24
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 Winchester. 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
$899,008
$20K under list price of $919K
Nearby comparable homes
The Redfin Estimate uses 6 recent nearby sales, priced between $860K to $1.4M.