Welcome to 258 Cross Street, a masterfully updated Winchester Colonial blending timeless character, modern comfort, and everyday function. Set on a level, fenced corner lot, this 4 bed, 2 bath home offers endless outdoor opportunity to relax, entertain, play, or dine al fresco. Inside, hardwood floors, crown molding, arched openings, bay windows, and ornate detail bring warmth and personality. The modernized kitchen beams with natural light and features upgraded cabinetry, stone counters, stainless appliances, and gas cooking. Both full baths have been tastefully updated with the larger featuring a tiled stand up shower, free standing soaking tub and a double vanity. Four bedrooms across the upper levels create flexibility for growing families, guests, WFH, fitness, or hobbies. Brand new central AC, central heat, full basement with laundry, and 4-car parking add functionality. Minutes from the iconic, and picturesque downtown Winchester, lined with shops, dining and even a T stop!
For sale
$999,900
258 Cross St, Winchester, MA 01890
4beds
1,719sqft
Single Family Residence
Built in 1860
7,700 Square Feet Lot
$983,100 Zestimate®
$582/sqft
$-- HOA
What's special
Brand new central acTiled stand up showerFull basement with laundryHardwood floorsOrnate detailArched openingsCentral heat
- 7 days |
- 1,271 |
- 61 |
Likely to sell faster than
Zillow last checked:
Listing updated:
Listed by:
Justin Blankenship 617-918-7419,
Fiv Realty Co 781-365-7984
Source: MLS PIN,MLS#: 73541288
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Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 2
- Full bathrooms: 2
Primary bedroom
- Features: Ceiling Fan(s), Closet/Cabinets - Custom Built, Flooring - Hardwood, Window(s) - Picture, Cable Hookup, High Speed Internet Hookup
- Level: Second
- Area: 244.38
- Dimensions: 17.25 x 14.17
Bedroom 2
- Features: Closet, Flooring - Hardwood, Window(s) - Picture, Cable Hookup, High Speed Internet Hookup, Lighting - Overhead
- Level: Second
- Area: 161.21
- Dimensions: 13.25 x 12.17
Bedroom 3
- Features: Closet, Flooring - Hardwood, Window(s) - Picture, Attic Access, Remodeled
- Level: Third
- Area: 149.81
- Dimensions: 11.75 x 12.75
Bedroom 4
- Features: Closet, Flooring - Wall to Wall Carpet, Window(s) - Picture, Attic Access, Remodeled
- Level: Third
- Area: 143.94
- Dimensions: 11.75 x 12.25
Bathroom 1
- Features: Bathroom - 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
- Level: Second
- Area: 80.24
- Dimensions: 9.08 x 8.83
Bathroom 2
- Features: Bathroom - Full, Bathroom - With Tub, Flooring - Stone/Ceramic Tile, Window(s) - Picture, Remodeled, Lighting - Overhead, Pedestal Sink, Soaking Tub
- Level: Second
- Area: 30.38
- Dimensions: 6.75 x 4.5
Dining room
- Features: Flooring - Hardwood, Window(s) - Picture, Lighting - Pendant, Crown Molding
- Level: Main,First
- Area: 185.01
- Dimensions: 12.83 x 14.42
Kitchen
- Features: Ceiling 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
- Level: Main,First
- Area: 205.83
- Dimensions: 13 x 15.83
Living room
- Features: Flooring - Hardwood, Window(s) - Bay/Bow/Box, Cable Hookup, High Speed Internet Hookup, Lighting - Overhead, Crown Molding, Vestibule
- Level: Main,First
- Area: 238.89
- Dimensions: 13.33 x 17.92
Heating
- Central, Forced Air
Cooling
- Central Air
Appliances
- Included: Gas Water Heater, Range, Dishwasher, Disposal, Microwave, Refrigerator, Freezer, Washer, Dryer
- Laundry: In Basement
Features
- Internet Available - Unknown
- Flooring: Wood, Tile, Carpet, Hardwood
- Basement: Full,Concrete,Unfinished
- Has fireplace: No
Interior area
- Total structure area: 1,719
- Total interior livable area: 1,719 sqft
- Finished area above ground: 1,719
Property
Parking
- Total spaces: 4
- Parking features: Off Street, Deeded, Paved
- Uncovered spaces: 4
Features
- Patio & porch: Patio
- Exterior features: Patio, Storage, Professional Landscaping, Fenced Yard, Garden
- Fencing: Fenced/Enclosed,Fenced
Lot
- Size: 7,700 Square Feet
- Features: Corner Lot, Level
Details
- Parcel number: 898140
- Zoning: RG
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Colonial
- Property subtype: Single Family Residence
Materials
- Frame
- Foundation: Stone
- Roof: Shingle
Condition
- Year built: 1860
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
- Utilities for property: for Gas Range
Community & HOA
Community
- Features: Public Transportation, Shopping, Pool, Tennis Court(s), Park, Walk/Jog Trails, Stable(s), Golf, Medical Facility, Bike Path, Conservation Area, Highway Access, House of Worship, Private School, Public School, T-Station, University, Sidewalks
HOA
- Has HOA: No
Location
- Region: Winchester
Financial & listing details
- Price per square foot: $582/sqft
- Tax assessed value: $865,700
- Annual tax amount: $9,591
- Date on market: 6/24/2026
- Listing terms: Contract
- Road surface type: Paved
Estimated market value
$983,100
$934,000 - $1.03M
$4,817/mo
Price history
| Date | Event | Price |
|---|---|---|
| 6/24/2026 | Listed for sale | $999,900+43%$582/sqft |
Source: MLS PIN #73541288 Report a problem | ||
| 6/1/2020 | Sold | $699,000$407/sqft |
Source: Public Record Report a problem | ||
| 3/26/2020 | Pending sale | $699,000$407/sqft |
Source: Leading Edge Real Estate #72585005 Report a problem | ||
| 12/5/2019 | Price change | $699,000-6.2%$407/sqft |
Source: Leading Edge Real Estate #72585005 Report a problem | ||
| 10/25/2019 | Listed for sale | $745,000+22.6%$433/sqft |
Source: Leading Edge Real Estate #72585005 Report a problem | ||
| 1/25/2019 | Sold | $607,500-6.5%$353/sqft |
Source: Public Record Report a problem | ||
| 11/28/2018 | Pending sale | $649,999$378/sqft |
Source: Leading Edge Real Estate #72380664 Report a problem | ||
| 10/31/2018 | Price change | $649,999-4.3%$378/sqft |
Source: Leading Edge Real Estate #72380664 Report a problem | ||
| 10/1/2018 | Price change | $679,000-2.9%$395/sqft |
Source: Leading Edge Real Estate #72380664 Report a problem | ||
| 8/9/2018 | Price change | $699,000-5.4%$407/sqft |
Source: Leading Edge Real Estate #72380664 Report a problem | ||
| 7/27/2018 | Price change | $739,000-2.6%$430/sqft |
Source: Leading Edge Real Estate #72380664 Report a problem | ||
| 7/6/2018 | Listed for sale | $759,000+64.1%$442/sqft |
Source: Leading Edge Real Estate #72380664 Report a problem | ||
| 8/10/2004 | Sold | $462,500+65.2%$269/sqft |
Source: Public Record Report a problem | ||
| 11/24/1998 | Sold | $279,900+86.6%$163/sqft |
Source: Public Record Report a problem | ||
| 9/22/1995 | Sold | $150,000$87/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $9,148 0% | $824,900 +2.1% |
| 2024 | $9,151 +4.9% | $807,700 +9.2% |
| 2023 | $8,725 +4.3% | $739,400 +10.6% |
| 2022 | $8,362 +1.1% | $668,400 +3.7% |
| 2021 | $8,273 +2.7% | $644,800 -0.8% |
| 2020 | $8,054 +7.3% | $650,000 +4.8% |
| 2019 | $7,508 +0.3% | $620,000 +1% |
| 2018 | $7,482 +4.4% | $613,800 +5.1% |
| 2017 | $7,169 +9.3% | $583,800 +3.9% |
| 2016 | $6,562 +0.3% | $561,800 +4.2% |
| 2015 | $6,543 +6.9% | $539,000 +11.5% |
| 2014 | $6,120 +9.9% | $483,400 +10.9% |
| 2013 | $5,568 +1.8% | $436,000 |
| 2012 | $5,472 +3.7% | $436,000 |
| 2011 | $5,276 +5.6% | $436,000 +0.4% |
| 2010 | $4,998 +2.1% | $434,200 |
| 2009 | $4,893 +4.6% | $434,200 -1.9% |
| 2008 | $4,677 -0.3% | $442,500 -2.6% |
| 2007 | $4,691 +1.7% | $454,100 +2.1% |
| 2006 | $4,612 +2.8% | $444,700 +3.3% |
| 2005 | $4,487 +6.1% | $430,600 +15.9% |
| 2004 | $4,228 +4.9% | $371,500 +4.9% |
| 2003 | $4,029 +11.2% | $354,000 +8% |
| 2002 | $3,624 +65.3% | $327,700 +55.6% |
| 2000 | $2,193 -5.6% | $210,600 +32.7% |
| 1999 | $2,323 | $158,700 |
Find assessor info on the county website
Monthly payment
Est. payment$--/mo
Payment breakdown
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HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
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Climate risks
Neighborhood: 01890
Nearby schools
GreatSchools rating
- 8/10Lynch Elementary SchoolGrades: PK-5Distance: 0.8 mi
- 8/10McCall Middle SchoolGrades: 6-8Distance: 1.1 mi
- 10/10Winchester High SchoolGrades: 9-12Distance: 0.7 mi
Schools provided by the listing agent
- Elementary: Lynch Elementary School
- Middle: Mccall Middle School
- High: Winchester High School
Source: MLS PIN. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
A local agent can set up tours, give advice and negotiate with sellers.
- Massachusetts
- Middlesex County
- Winchester
- 01890
- 258 Cross St
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