Dimensions11.75 x 12.25
FeaturesCloset, Flooring - Wall to Wall Carpet, Window(s) - Picture, Attic Access, Remodeled
LevelThird
258 Cross Street, Winchester MA 01890
Winchester, MA 01890 • Winchester Highlands
$999,900
Est. $6,055/month
About this home
A rare Winchester opportunity 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 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. 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. Previously prepared conceptual expansion plans are available for review. Minutes from the iconic, and picturesque downtown. Rear vestibule is the perfect place for a 1st floor half bath (see attached rendering). Smaller upstairs bathroom could be converted to a 1/2 bath with stackable laundry or a dedicated laundry room (SEE ATTACHED RENDERINGS).
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Property History
Market Insights
39.2%
Price Range
2
Previous Sales
Property Timeline
Listed for Sale
Jun 24, 2026
$999,900
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 |
|---|---|---|---|---|---|
| 06/24/2026 | 🏠 Listed for Sale | $999,900 | - | - | 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
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
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)
41 days
Property Overview
Property Type
Single Family Residence
Listing Type
For Sale
Year Built
1860
Bedrooms
4
Full Bathrooms
2
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 12.75
FeaturesCloset, Flooring - Hardwood, Window(s) - Picture, Attic Access, Remodeled
LevelThird
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
Dimensions13.25 x 12.166666666
FeaturesCloset, Flooring - Hardwood, Window(s) - Picture, Cable Hookup, High Speed Internet Hookup, Lighting - Overhead
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
Dimensions12.833333333 x 14.416666666
FeaturesFlooring - Hardwood, Window(s) - Picture, Lighting - Pendant, Crown Molding
LevelMain,First
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
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
BABathroom (4)
BRBedroom (5)
DDining (1)
KKitchen (1)
LLiving (2)
OOffice (1)
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
10 schools
Acera School
0.2 mi
Grades K-08
The Wilder School
0.5 mi
Grades K-12
A+
Muraco Elementary School
0.3 mi
|
#62 of 824
|
Score: 61.6
Improved 62 spots from last year
+3.4 above state avg
352 students
Diverse
Rising School
Strong Attendance
Grades K-05
Creative Corner School Inc
0.5 mi
Grades PK-K
A
Lynch Elementary School
0.8 mi
|
#113 of 824
|
Score: 58.6
Dropped 31 spots from last year
+0.4 above state avg
426 students
Diverse
Grades PK-05
St. Mary Elementary School
0.8 mi
Grades PK-05
A+
Lincoln Elementary School
1.0 mi
|
#74 of 824
|
Score: 60.7
Dropped 29 spots from last year
+2.5 above state avg
334 students
Moderate
Strong Attendance
Grades K-05
A+
Ambrose Elementary School
1.7 mi
|
#11 of 824
|
Score: 66.1
Improved 36 spots from last year
+7.9 above state avg
398 students
Moderate
Rising School
Strong Attendance
Grades K-05
Children's Own School
1.9 mi
Grades PK-K
A+
Vinson-Owen Elementary School
2.2 mi
|
#40 of 824
|
Score: 63.2
Improved 112 spots from last year
+5 above state avg
441 students
Diverse
Rising School
Strong Attendance
Grades PK-05
Middle Schools
1 school
A+
McCall Middle School
1.1 mi
|
#16 of 352
|
Score: 62.4
Dropped 3 spots from last year
+4.2 above state avg
1,036 students
Diverse
Strong Attendance
Grades 06-08
High Schools
1 school
A+
Winchester High School
0.7 mi
|
#17 of 346
|
Score: 73.6
Improved 18 spots from last year
+15.4 above state avg
1,404 students
Diverse
20 sports
• 2,818 athletes
Strong AP Program
High Graduation Rate
College Ready Curriculum
Strong Athletics
Grades 09-12
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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 Street, 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
Aug 4, 2026 4:12 PM 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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