258 Cross St Winchester, MA $ 974,900
258 Cross St
$ 974,900
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258 Cross St

Winchester, MA, 01890
$ 974,900
Bedrooms3 Baths2.1 Sq 1,719

Monthly Estimate*

$ 6,733

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Single Family Home for sale in Winchester, MA

for $974,900 with 3 bedrooms and 2 full baths, 1 half bath. This 1,719 square foot home was built in 1860 on a lot size of 0.18.

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.

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Single Family Active

Price

$ 974,900

Bedrooms

3

Full Bath

2

Half Bath

1

Property Type

Single Family

Taxes

$ 9,591

Style

Colonial

Lot Size

0.18

Year Built

1860

Town/City

Winchester

County/Region

Middlesex

MLS | Web ID

73575764

List By
Justin Blankenship

Listing Agent

Fiv Realty Co

Broker

Affordability Calculator

$7,533
Per Month
89%
11%
0%
Monthly Principal & Interest
$6,733
Monthly Property Taxes
$799
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 7.375% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Pricing History
DatePricePrice ChangeDescription
9/11/2026$974,900 Listed Price

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258 Cross St, Winchester, MA, 01890 is a Single Family Home for sale at $974,900 with 1,719 sqft and a lot size of 0.18. 258 Cross St has 3 bedrooms, 2.1 baths, and was built in 1860. The property's zip code is 01890 which is in Winchester, MA