Skip to content
Bean Group
Offered at $974,900Active
beds
3
baths
3
sq ft
1,719
Built
1860

258 Cross St

Winchester, MA 01890

About this home

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.

Listing last checked: Listing updated:

Listed by Justin Blankenship · Fiv Realty Co · MLS #73575764

Request property information

Select a document to start a request. You can add others in the form. Availability varies.

Details at a glance

Interior5 property facts
Rooms
7
Heating
Central, Forced Air
Cooling
Central Air
Flooring
Wood, Tile, Carpet, Hardwood
Basement
Yes · Full, Concrete, Unfinished
Building5 property facts
Style
Single Family Residence
Year built
1860
Parking
4
Foundation
Stone
Roof
Shingle
Land & utilities5 property facts
Lot size
0.18 acres
Water
Public
Sewer
Public Sewer
Pool
Not reported
Zoning
RG
Financial2 property facts
Annual taxes
$9,592
Assessment year
2026

Location

Estimated monthly cost

Explore costs at the $974,900 asking price. Adjust the assumptions to your situation.

Known monthly costs$5,729 / monthAdjust
Principal & interest
$4,930
Property tax
$799
Insurance
Not entered
HOA
Not entered

Listing annual taxes: $9,592. Initial monthly tax is one twelfth of that amount. HOA amount was not supplied.

Partial estimate: add insurance, monthly HOA to include those costs. Blank amounts are unknown.

The initial 6.5% rate is illustrative, not a current rate or lender quote. Excludes utilities, maintenance, closing costs and mortgage insurance, which may apply with a down payment below 20%. Taxes and insurance can change.

More property insights

Automated value estimate $1,036,065

Estimated range $986,411–$1,085,718.

Automated estimates are not appraisals or guarantees of market value.

Request a professional market analysis
Comparable properties 1 supplied

Sold Aug 9, 2026

$992,500

35 Grove St.

Photo-based condition insights

Overall presentation: above average

Explore more of Winchester

Continue your search in Winchester.

Need help making sense of this home?

About 258 Cross St

Can I request a private showing?

Request a tour of 258 Cross St and a Bean Group agent will help coordinate an available time with the listing side.

Can you help me evaluate this property?

Yes. We can discuss condition, comparable sales, offer strategy and the questions worth asking before you decide whether to proceed.

Are property documents available?

Availability varies by property and source. Request the documents you need and we will help obtain what is available.