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.
For sale
$974,900
258 Cross St, Winchester, MA 01890
3beds
1,719sqft
Single Family Residence
Built in 1860
7,700 Square Feet Lot
$956,300 Zestimate®
$567/sqft
$-- HOA
What's special
Brand-new central acTiled showerStorage shedUpdated eat-in kitchenHardwood floorsBrand-new first-floor powder roomFinished third floor
- 6 days
- 371
- 40
Zillow last checked:
Listing updated:
Listed by:
Justin Blankenship 617-918-7419,
Fiv Realty Co 781-365-7984
Source: MLS PIN,MLS#: 73575764
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 3
- Full bathrooms: 2
- 1/2 bathrooms: 1
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
Bathroom 3
- Features: Bathroom - Half
- Level: First
- Area: 20
- Dimensions: 5 x 4
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: $567/sqft
- Tax assessed value: $865,700
- Annual tax amount: $9,591
- Date on market: 9/24/2026
- Listing terms: Contract
- Exclusions: 1/2 Bathroom Mirror
- Road surface type: Paved
Estimated market value
$956,300
$908,000 - $1.00M
$3,781/mo
Price history
| Date | Event | Price |
|---|---|---|
| 9/11/2026 | Listed for sale | $974,900-2.5%$567/sqft |
Source: MLS PIN #73575764 Report a problem | ||
| 9/11/2026 | Listing removed | $999,900$582/sqft |
Source: MLS PIN #73541288 Report a problem | ||
| 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
Payment breakdown
Explore the cost of this home by adjusting the details. Changes won't be saved.Climate risks
Neighborhood: 01890
Nearby schools
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.
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