Dimensions11.75 x 12.75
FeaturesCloset, Flooring - Hardwood, Window(s) - Picture, Attic Access, Remodeled
LevelThird
258 Cross St, Winchester MA 01890
Winchester, MA 01890 • Winchester Highlands
$974,900
Est. $5,929/month
Estimate assumptions
20% down, a 30-year loan at 6.5%, and $200/month estimated insurance.
Includes the supplied property-tax and HOA inputs; missing inputs contribute $0. HOA fees with an unspecified frequency are treated as monthly. PMI and closing costs are excluded.
Adjust the payment calculatorTrack this home for price, status, and open-house alerts.
Open House Schedule
13
Sep
Sunday, September 13
11:00 AM - 1:00 PM EDT
12
Sep
Saturday, September 12
11:00 AM - 1:00 PM EDT
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.
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Recently Sold Nearby
Property History
Market Insights
37.7%
Price Range
2
Previous Sales
Property Timeline
Listed for Sale
Sep 11, 2026
$974,900
Original listing
Agent: Justin Blankenship
Office: Fiv Realty Co
Previous Transaction - MLS #72585005
Full transaction history available when tracking began
Previously Sold
Jun 1, 2020
$699,000
MLS #72585005
Previous Transaction - MLS #72380664
Full transaction history available when tracking began
Previously Sold
Jan 25, 2019
$607,500
MLS #72380664
| Date | Event | Price | Change | $/sqft | Details |
|---|---|---|---|---|---|
| 09/11/2026 | 🏠 Listed for Sale | $974,900 | - | - | Original listing |
| 06/01/2020 | 🏷️ Previously Sold | $699,000 | - | - | MLS #72585005 |
| 01/25/2019 | 🏷️ Previously Sold | $607,500 | - | - | MLS #72380664 |
Tax History
| Year | Taxes | Assessment |
|---|---|---|
| 2026 | $9,592 | $865,700 |
Financial Details
Annual Property Tax
$9,592
Tax Year 2026
Assessed Value
$865,700
Facts & Features
Central AC
Home Facts
Type
Residential
Style
Single Family Residence
Year Built
1860
Living Area
1,719 sq ft
Lot Size
0.18 acres
Bedrooms
4
Full Baths
2
Half Baths
1
Total Rooms
7
Interior
Heating
Central, Forced Air
Cooling
Central Air
Flooring
Wood, Tile, Carpet, Hardwood
Appliances
Gas Water Heater, Range, Dishwasher, Disposal, Microwave, Refrigerator, Freezer, Washer, Dryer
Fireplace
None
Basement
Full, Concrete, Unfinished
Laundry
In Basement
Features
Internet Available - Unknown
Exterior
Construction
Frame
Architecture
Colonial
Roof
Shingle
Features
Patio, Storage, Professional Landscaping, Fenced Yard, Garden
Pool
None
Spa
None
Fencing
Fenced/enclosed, Fenced
Patio/Porch
Patio
Parking
Features
Off Street, Deeded, Paved
Total Spaces
4
Utilities
Electric
None
Water
Public
Sewer
Public Sewer
Gas
None
Other
For Gas Range
Financial
Annual Tax
$9,592
Assessed Value
$865,700
HOA & Community
Fee Includes
None
Amenities
None
Optional Fee Includes
None
MA Disclosures
Lead Paint
Unknown
Seller Disclosures
Some Photos Have Been Adjusted Using Ai Technology. Please Park On River Street For Showings. Previously Prepared 2020 Conceptual Addition Plans Available For Review. Plans Are Historical Only And Have Not Been Verified As Currently Approved, Valid, Or Buildable. Buyer To Perform All Due Diligence.
Additional Details
Possession
None
Accepted Financing
Contract
Structure Type
[]
House Color
Grey
Sq Ft Source
Public Record
Sq Ft Disclosures
All measurements provided are for marketing purposes only. Buyer(s) to perform their due diligence
Documents
None
County
Middlesex
Total market time (incl. prior listings)
78 days
Property Overview
Property Type
Single Family Residence
Listing Type
For Sale
Year Built
1860
Bedrooms
4
Full Bathrooms
2
Half Bathrooms
1
Living Area
1,719 sq ft
Total Rooms
7
Floor Layout
Interactive room guide
Floor Layout
Finished Area
1,719 sq ft above grade
Dimensions11.75 x 12.25
FeaturesCloset, Flooring - Wall to Wall Carpet, Window(s) - Picture, Attic Access, Remodeled
LevelThird
Dimensions13.25 x 12.166666666
FeaturesCloset, Flooring - Hardwood, Window(s) - Picture, Cable Hookup, High Speed Internet Hookup, Lighting - Overhead
LevelSecond
Dimensions9.083333333 x 8.833333333
FeaturesBathroom - 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
LevelSecond
Dimensions6.75 x 4.5
FeaturesBathroom - Full, Bathroom - With Tub, Flooring - Stone/Ceramic Tile, Window(s) - Picture, Remodeled, Lighting - Overhead, Pedestal Sink, Soaking Tub
LevelSecond
Dimensions17.25 x 14.166666666
FeaturesCeiling Fan(s), Closet/Cabinets - Custom Built, Flooring - Hardwood, Window(s) - Picture, Cable Hookup, High Speed Internet Hookup
LevelSecond
Dimensions13 x 15.833333333
FeaturesCeiling 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
LevelMain,First
Dimensions5 x 4
FeaturesBathroom - Half
LevelFirst
Dimensions12.833333333 x 14.416666666
FeaturesFlooring - Hardwood, Window(s) - Picture, Lighting - Pendant, Crown Molding
LevelMain,First
Dimensions13.333333333 x 17.916666666
FeaturesFlooring - Hardwood, Window(s) - Bay/Bow/Box, Cable Hookup, High Speed Internet Hookup, Lighting - Overhead, Crown Molding, Vestibule
LevelMain,First
Display Options
Outdoor Areas
Patio & porchPatio
Room Markers
OOffice (1)
KKitchen (1)
BRBedroom (5)
BABathroom (4)
DDining (1)
LLiving (2)
Conceptual diagram based on MLS room data. It is not to scale and is not a substitute for architectural plans or on-site measurements.
Interior Features
Flooring:
Wood, Tile, Carpet, Hardwood
Appliances:
Gas Water Heater, Range, Dishwasher, Disposal, Microwave, Refrigerator, Freezer, Washer, Dryer
Interior Features:
Internet Available - Unknown
Windows:
Basement:
Full, Concrete, Unfinished
Laundry:
In Basement
Security:
Construction & Materials
Style:
Colonial
Year Built:
1860
Structure Type:
Exterior Materials:
Frame
Roof:
Shingle
Foundation:
Stone
Heating, Cooling & Utilities
Heating:
Central, Forced Air
Heating Zones:
1
Cooling:
Central Air
Cooling Zones:
1
Hot Water:
Water Source:
Public
Sewer:
Public Sewer
Energy Features:
Exterior & Lot
Exterior Features:
Patio, Storage, Professional Landscaping, Fenced Yard, Garden
Patio & Porch:
Patio
Fencing:
Fenced/Enclosed, Fenced
Other Structures:
Lot Features:
Corner Lot, Level
Road Surface:
Paved
Parking & Garage
Total Parking Spaces:
4
Parking Features:
Off Street, Deeded, Paved
Nearby Schools
School District
Winchester School District local
A+
School Safety
2024-25
0.1%
Very Low (Safest)
0.1%
Suspensions
0.1%
In-School
5.4% below state avg
Elementary Schools
3 schools
Acera School
0.2 mi
Grades K-08
A+
Muraco Elementary School
0.3 mi
|
#64 of 825
|
Score: 61.2
Improved 60 spots from last year
+3 above state avg
296 students
Diverse
Rising School
Strong Attendance
Grades K-05
Creative Corner School Inc
0.5 mi
Grades PK-K
Middle Schools
3 schools
A+
McCall Middle School
1.1 mi
|
#15 of 352
|
Score: 62.8
Dropped 2 spots from last year
+4.6 above state avg
1,053 students
Diverse
Strong Attendance
Grades 06-08
B
John F Kennedy Middle School
1.9 mi
|
#168 of 352
|
Score: 42.9
Improved 50 spots from last year
-15.3 below state avg
498 students
Diverse
Rising School
Diverse Student Body
Strong Attendance
Grades 06-08
C+
Daniel L Joyce Middle School
2.1 mi
|
#218 of 352
|
Score: 39.3
Dropped 15 spots from last year
-18.9 below state avg
434 students
Diverse
Strong Attendance
Grades 06-08
High Schools
3 schools
A+
Winchester High School
0.7 mi
|
#16 of 346
|
Score: 74.0
Improved 19 spots from last year
+15.8 above state avg
1,418 students
Diverse
20 sports
• 2,818 athletes
Strong AP Program
High Graduation Rate
College Ready Curriculum
Strong Athletics
Grades 09-12
B
Woburn High School
1.2 mi
|
#147 of 346
|
Score: 56.6
Dropped 25 spots from last year
-1.6 below state avg
1,203 students
Diverse
18 sports
• 2,056 athletes
Strong AP Program
High Graduation Rate
College Ready Curriculum
Strong Athletics
Grades 09-12
A-
Stoneham High School
2.5 mi
|
#89 of 346
|
Score: 61.7
Improved 39 spots from last year
+3.5 above state avg
598 students
Moderate
17 sports
• 1,334 athletes
Strong AP Program
High Graduation Rate
Rising School
College Ready Curriculum
Grades 09-12
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Property Tax
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Homeowners Insurance
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95% Interest
Year 15
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Location
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Neighborhood
Winchester Highlands
258 Cross St, Winchester MA 01890
Winchester, MA 01890
Listing Information
Listing Agent
Justin Blankenship
Listing Office
Fiv Realty Co
Office Phone
781-365-7984
Agent MLS ID
CN213602
Office MLS ID
AN8709
Listing Data Updated
Sep 11, 2026 12:09 AM EDT
Listing information is deemed reliable but not guaranteed. Data provided by MLS Property Information Network, Inc. All information should be independently verified.
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