258 Cross Street Winchester, MA ^$ 999,900

258 Cross Street

^$ 999,900

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258 Cross Street

Winchester, MA, 01890

^$ 999,900

Bedrooms4 Baths2.0 Sq 1,719

Monthly Estimate*

^$ 6,313

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Single Family Home for sale in Winchester, MA

for $999,900 with 4 bedrooms and 2 full baths. This 1,719 square foot home was built in 1860 on a lot size of 0.18.

A rare Winchester opportunity under $1M, 258 Cross Street blends timeless character, meaningful updates, everyday function, and exciting long-term upside. Set on a level, fenced corner lot, this 4 bed, 2 bath Colonial offers the space buyers need today with the flexibility to evolve over time. Inside - hardwood floors, crown molding, arched openings, bay windows, and detailed trim add warmth, while the updated kitchen features stone counters, upgraded cabinetry, stainless appliances, gas cooking, and great natural light. Both full baths have been tastefully updated, including a larger bath with double vanity, tiled shower, and soaking tub. Four bedrooms on the upper levels create options for guests, office, fitness, hobbies, or future needs. Brand new AC, central heat, full basement with laundry/storage, patio, fenced yard, shed, and 4-car parking add real utility. Previously prepared conceptual expansion plans are available for review. Minutes from the iconic, and picturesque downtown. Rear vestibule is the perfect place for a 1st floor half bath (see attached rendering). Smaller upstairs bathroom could be converted to a 1/2 bath with stackable laundry or a dedicated laundry room (SEE ATTACHED RENDERINGS).

Single Family Active

Price

^$ 999,900

Bedrooms

Full Bath

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

73541288

List By

Justin Blankenship

Listing Agent

Fiv Realty Co

Broker

Affordability Calculator

$7,113

Per Month

Monthly Principal & Interest: $6,313
Monthly Property Taxes: $799
Monthly Home Insurance: --

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Default based on a 30-year fixed rate of 6.49% 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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Trends

Single family listings in Winchester, MA

Average List Price ^$2,102,027

Percent of Sale Price 110%

About Winchester, MA

22,228 Population

7% Since 2002

^$152,119 Median Income

45.68 Median Age

42% Households with Children

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Trends Information provided by ATTOM Data Solutions.

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Pricing History

Date	Price	Price Change	Description
6/25/2026	$999,900		Listed Price

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258 Cross Street, Winchester, MA, 01890 is a Single Family Home for sale at $999,900 with 1,719 sqft and a lot size of 0.18. 258 Cross Street has 4 bedrooms, 2.0 baths, and was built in 1860. The property's zip code is 01890 which is in Winchester, MA

*Information deemed reliable but not guaranteed.

Financial calculator disclaimer: Default based on a 30-year fixed rate of 6.49% 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.

Data is updated as of 8/13/2026.

The real estate information and related content displayed on this site is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

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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258 Cross Street

Single Family Home for sale in Winchester, MA

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