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.
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About this home
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.
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Public Records & Permits
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Recently Sold Nearby
Property History
Property Timeline
Listed for Sale
Sep 11, 2026
$974,900
Original listing
Agent: Justin Blankenship
Office: Fiv Realty Co
| Date | Event | Price | Change | $/sqft | Details |
|---|---|---|---|---|---|
| 09/11/2026 | 🏠 Listed for Sale | $974,900 | - | - | Original listing |
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
3
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.
Exclusions
1/2 Bathroom Mirror
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)
83 days
Property Overview
Property Type
Single Family Residence
Listing Type
For Sale
Year Built
1860
Bedrooms
3
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 information not available for this location.
Monthly Payment Calculator
Monthly Payment
$0
Principal, interest, taxes & insurance
Loan Amount
$0
After down payment
Total Interest
$0
Over life of loan
Total Cost
$0
Including down payment
%
Down: $0
%
Monthly Payment Breakdown
Principal & Interest
$0
Property Tax
$799
Homeowners Insurance
$200
PMI (if <20% down)
$0
Loan Summary
Total of 360 payments
$0
Total principal paid
$0
Total interest paid
$0
Rate Impact
-0.5% Rate
$0/mo
Save $0/mo
Current Rate
$0/mo
+0.5% Rate
$0/mo
Cost $0/mo
Payment Over Time
Year 1
95% Interest
Year 15
50/50
Year 30
95% Principal
* Estimates only. Actual payments may vary. Consult with a lender for accurate figures.
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 15, 2026 1:40 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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