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Street View
$974,900
Monthly Est:$4,852
3 Beds
- 3 Baths
2 full baths + 1 half bath
1,719sqft
258 Cross St, Winchester, MA 01890
$974,900
$4,852/moEst:
Get Pre-Approved
Single Family Residence
Built in 1860
$-- HOA
0.18 acre lot
$567/sq.ft
Description
Are rates making you feel like home buying is out of reach? The sellers are now offering A TWENTY THOUSAND DOLLAR ($20,000) CREDIT, PERFECT to put towards closing costs or a 2/1 rate buy down. Enjoy over a ONE THOUSAND ($1000) DOLLAR PER MONTH savings year one and over a FIVE HUNDRED ($500) DOLLAR PER MONTH savings year two. 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.
- Houzeo last checked: 14 minutes ago
- Listing updated: October 15, 2026 at 1:20 pm
- Listing Provided by: Justin Blankenship (617) 918-7419 | Fiv Realty Co. (781) 365-1984
- Source: MLS Property Information Network-MA | MLS#: 73575764

Property Details
Status
Active
Type
Single Family Residence
No. of Stories
-
County
City
Neighborhood
--
Year Built
1860
HOA Fees
-
Finished Area
1,719 sqft
Lot Size
0.18 acre lot
Basement Area
- sqft
MLS Name
MLS Property Information Network
MLS Number
73575764
MLS Status
Active
Days on Market
53

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Location
Facts & Features
Rooms
Bedrooms & bathrooms
Bedrooms: 3
Bathrooms: 3
Interior
Appliances
Gas Water Heater, Range, Dishwasher, Disposal, Microwave, Refrigerator, Freezer, Washer, Dryer
Heating
Central, Forced Air
Exterior Features
Patio, Storage, Professional Landscaping, Fenced Yard, Garden
Cooling
Central Air
Interior Features
Internet Available Unknown
Flooring
Wood, Tile, Carpet, Hardwood
Sewer
Public Sewer
Construction
Year Built
Year Built: 1860
Home type
Single Family Residence
Construction Materials
Frame
Architectural Style
Colonial
Roof
Shingle
Foundation Details
Stone
Utilities & Energy
Parking Features
Off Street, Deeded, Paved
Utilities
For Gas Range
Water Source
Public
Laundry Features
In Basement
Basement
Full, Concrete, Unfinished
Other Features
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.
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
Lot Features
Corner Lot, Level
Patio And Porch Features
Patio
Price History
| Date | Event | Price |
|---|---|---|
09/11/2026 Source: | Listing Removed | $999,900 $582/sqft |
06/24/2026 Source: | Listed for Sale | $999,900 +64.59% $582/sqft |
01/25/2019 Source: | Sold | $607,500 -6.54% $353/sqft |
01/25/2019 Source: | Price Decreased | $649,999 -7.01% $378/sqft |
08/17/2018 Source: | Listing Removed | $699,000 $407/sqft |
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Based on information provided to and compiled by MLS Property Information Network, Inc. covering through Nov 04, 2026, 12:45AM. 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. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified. © 2026 MLS Property Information Network, Inc. All Rights Reserved.
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