258 Cross St Winchester, MA 01890
Estimated payment $6,189/month
4
Beds
2
Baths
1,719
Sq Ft
$582
Price per Sq Ft
Highlights
- Community Stables
- Medical Services
- Colonial Architecture
- Lynch Elementary School Rated A+
- Custom Closet System
- Landscaped Professionally
About This Home
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 downtown Winchester with the most scenic downtown around, lined with shops, dining and even the T
Open House Schedule
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Thursday, June 25, 20264:30 to 5:30 pm6/25/2026 4:30:00 PM +00:006/25/2026 5:30:00 PM +00:00Please park on River Street and come through the gate at the top of the garage for touring.Add to Calendar
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Saturday, June 27, 202612:00 to 2:00 pm6/27/2026 12:00:00 PM +00:006/27/2026 2:00:00 PM +00:00Please park on River Street and come through the gate at the top of the garage for touring. Monica will get you / your client signed in and assist as much as she can as a fill in.Add to Calendar
Home Details
Home Type
- Single Family
Est. Annual Taxes
- $9,592
Year Built
- Built in 1860 | Remodeled
Lot Details
- 7,700 Sq Ft Lot
- Fenced Yard
- Landscaped Professionally
- Corner Lot
- Level Lot
- Garden
- Property is zoned RG
Home Design
- Colonial Architecture
- Stone Foundation
- Frame Construction
- Shingle Roof
Interior Spaces
- 1,719 Sq Ft Home
- Crown Molding
- Ceiling Fan
- Recessed Lighting
- Decorative Lighting
- Light Fixtures
- Bay Window
- Picture Window
- Entrance Foyer
- Attic Access Panel
Kitchen
- Stove
- Range
- Microwave
- Freezer
- Dishwasher
- Stainless Steel Appliances
- Solid Surface Countertops
- Disposal
Flooring
- Wood
- Wall to Wall Carpet
- Ceramic Tile
Bedrooms and Bathrooms
- 4 Bedrooms
- Primary bedroom located on second floor
- Custom Closet System
- 2 Full Bathrooms
- Double Vanity
- Bidet
- Pedestal Sink
- Freestanding Bathtub
- Soaking Tub
- Bathtub with Shower
Laundry
- Dryer
- Washer
Unfinished Basement
- Basement Fills Entire Space Under The House
- Laundry in Basement
Parking
- 4 Car Parking Spaces
- Paved Parking
- 4 Open Parking Spaces
- Off-Street Parking
- Deeded Parking
Outdoor Features
- Patio
- Outdoor Storage
Location
- Property is near golf course, public transit, and schools
Schools
- Lynch Elementary School
- Mccall Middle School
- Winchester High School
Utilities
- Forced Air Heating and Cooling System
- 1 Cooling Zone
- 1 Heating Zone
- Gas Water Heater
- High Speed Internet
- Internet Available
- Cable TV Available
Listing and Financial Details
- Assessor Parcel Number 898140
Community Details
Overview
- No Home Owners Association
- Near Conservation Area
Amenities
- Medical Services
- Shops
Recreation
- Tennis Courts
- Community Pool
- Park
- Community Stables
- Jogging Path
- Bike Trail
3D Interior and Exterior Tours
Floorplans
Map
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Tax History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
|---|---|---|---|---|
| 2025 | $91 | $824,900 | $502,200 | $322,700 |
| 2024 | $9,151 | $807,700 | $502,200 | $305,500 |
| 2023 | $8,725 | $739,400 | $439,500 | $299,900 |
| 2022 | $8,362 | $668,400 | $376,700 | $291,700 |
| 2021 | $8,273 | $644,800 | $353,100 | $291,700 |
| 2020 | $8,054 | $650,000 | $353,100 | $296,900 |
| 2019 | $7,508 | $620,000 | $255,000 | $365,000 |
| 2018 | $7,482 | $613,800 | $248,800 | $365,000 |
| 2017 | $7,169 | $583,800 | $248,800 | $335,000 |
| 2016 | $6,562 | $561,800 | $248,800 | $313,000 |
| 2015 | $6,543 | $539,000 | $226,000 | $313,000 |
| 2014 | $6,120 | $483,400 | $188,300 | $295,100 |
Source: Public Records
Property History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Event | Price | List to Sale | Price per Sq Ft | Prior Sale |
|---|---|---|---|---|---|
| 06/24/2026 06/24/26 | For Sale | $999,900 | +43.0% | $582 / Sq Ft | |
| 06/01/2020 06/01/20 | Sold | $699,000 | 0.0% | $407 / Sq Ft | View Prior Sale |
| 03/26/2020 03/26/20 | Pending | -- | -- | -- | |
| 12/05/2019 12/05/19 | Price Changed | $699,000 | -6.2% | $407 / Sq Ft | |
| 10/25/2019 10/25/19 | For Sale | $745,000 | +22.6% | $433 / Sq Ft | |
| 01/25/2019 01/25/19 | Sold | $607,500 | -6.5% | $348 / Sq Ft | View Prior Sale |
| 11/28/2018 11/28/18 | Pending | -- | -- | -- | |
| 10/31/2018 10/31/18 | Price Changed | $649,999 | -4.3% | $372 / Sq Ft | |
| 10/01/2018 10/01/18 | For Sale | $679,000 | +11.8% | $388 / Sq Ft | |
| 09/30/2018 09/30/18 | Off Market | $607,500 | -- | -- | |
| 08/17/2018 08/17/18 | For Sale | $699,000 | -- | $400 / Sq Ft |
Source: MLS Property Information Network (MLS PIN)
Purchase History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Type | Sale Price | Title Company |
|---|---|---|---|
| Not Resolvable | $699,000 | None Available | |
| Not Resolvable | $607,500 | -- | |
| Deed | $462,500 | -- | |
| Deed | $279,900 | -- | |
| Deed | $150,000 | -- |
Source: Public Records
Mortgage History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Status | Loan Amount | Loan Type |
|---|---|---|---|
| Open | $699,000 | Purchase Money Mortgage | |
| Previous Owner | $805,000 | Purchase Money Mortgage | |
| Previous Owner | $266,000 | No Value Available | |
| Previous Owner | $30,000 | No Value Available |
Source: Public Records
About the Listing Agent
I’m a North Andover-based Realtor with over 10 years of experience serving buyers, sellers, and investors throughout Andover, the North Shore, and Greater Boston. Over the course of my career, I’ve helped clients successfully close more than 100 home sales and assisted hundreds more with rentals and investment properties across Eastern Massachusetts.
Before joining Kadilak Realty Group under Fiv Realty Co., I owned and operated a boutique brokerage and a property management company,
Justin's Other Listings
Source: MLS Property Information Network (MLS PIN)
MLS Number: 73541288
APN: WINC-000013-000250
Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.
The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.
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Your Personal Tour Guide
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