Active

57 Days on market

258 Cross Street Winchester — Photo 1 of 39

$999,900

258 Cross Street, Winchester, MA 01890

Winchester, MA 01890 — Winchester Highlands

Beds

Baths

SqFt

1,719

Style

Single Family

Built

1860

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).

Market Value Analysis

This Property

Size (SqFt) →Price →

This Property$582/sqft

Local Avg (Winchester)$573/sqft

2% AboveMarket Average

* Analysis is based on 24 actively listed and recently sold comparable properties strictly within Winchester, MA.

Financials

Original Price$999,900

Annual Taxes$9,591.95

Parking

Garage0

Off-Street4

Interior Specifications

Total Rooms7

FireplacesNone

FlooringWood, Tile, Carpet, Hardwood

BasementFull, Concrete, Unfinished

Climate & Utilities

HeatingCentral, Forced Air

CoolingCentral Air

WaterPublic

SewerPublic Sewer

Building & Exterior

ConstructionFrame

RoofShingle

FoundationStone

ZoningRG

Property & Lot

Acres0.18

SqFt Lot7,700

Lot FeaturesCorner Lot, Level

Amenities & Appliances

Gas Water Heater • Range • Dishwasher • Disposal • Microwave • Refrigerator • Freezer • Washer • Dryer

Neighborhood

Public Transportation • Shopping • Pool • Tennis Court(s) • Park • Walk/Jog Trails

Geography

Floorplan Breakdown

Structural Layout

Third

Bedroom 3Bedroom 4

Second

Master BedroomBedroom 2Bathroom 1Bathroom 2

Main,First

Living RoomDining RoomKitchen

Living Room

Lvl Main,First

13.333333333 x 17.916666666

Flooring - Hardwood, Window(s) - Bay/Bow/Box, Cable Hookup, High Speed Internet Hookup, Lighting - Overhead, Crown Molding, Vestibule

Dining Room

Lvl Main,First

12.833333333 x 14.416666666

Flooring - Hardwood, Window(s) - Picture, Lighting - Pendant, Crown Molding

Kitchen

Lvl Main,First

13 x 15.833333333

Ceiling Fan(s), Flooring - Stone/Ceramic Tile, Window(s) - Picture, Countertops - Stone/Granite/Solid, Cabinets - Upgraded, Exterior Access, Recessed Lighting, Remodeled, Stainless Steel Appliances, Gas Stove, Vestibule

Master Bedroom

Lvl Second

17.25 x 14.166666666

Ceiling Fan(s), Closet/Cabinets - Custom Built, Flooring - Hardwood, Window(s) - Picture, Cable Hookup, High Speed Internet Hookup

Bedroom 2

Lvl Second

13.25 x 12.166666666

Bedroom 3

Lvl Third

11.75 x 12.75

Closet, Flooring - Hardwood, Window(s) - Picture, Attic Access, Remodeled

Bedroom 4

Lvl Third

11.75 x 12.25

Closet, Flooring - Wall to Wall Carpet, Window(s) - Picture, Attic Access, Remodeled

Bathroom 1

Lvl Second

9.083333333 x 8.833333333

Bathroom - Full, Bathroom - Double Vanity/Sink, Bathroom - With Tub & Shower, Flooring - Stone/Ceramic Tile, Window(s) - Picture, Countertops - Stone/Granite/Solid, Countertops - Upgraded, Bidet, Cabinets - Upgraded, Remodeled, Lighting - Overhead, Soaking Tub

Bathroom 2

Lvl Second

6.75 x 4.5

Bathroom - Full, Bathroom - With Tub, Flooring - Stone/Ceramic Tile, Window(s) - Picture, Remodeled, Lighting - Overhead, Pedestal Sink, Soaking Tub

Population

23,406

U.S. Census Bureau, ACS 2024 5-Year Estimates (B01003)

Median Household Income

$230K

U.S. Census Bureau, ACS 2024 5-Year Estimates (B19013)

Renter-Occupied Homes

18.3%

U.S. Census Bureau, ACS 2024 5-Year Estimates (B25003)

New Construction Permits — Middlesex County

2,667 housing units permitted in the last 12 months (-2% vs the prior 12 months) — 1,709 in 5+ unit buildings

U.S. Census Bureau, Building Permits Survey (through Jun '26)

ADU Potential

Massachusetts allows one accessory dwelling unit by right in single-family zoning districts statewide (M.G.L. c. 40A §3; 760 CMR 71.00, effective Feb 2025). Estimated maximum ADU size for this property: 860 sq ft (the lesser of 900 sq ft or half the 1,719 sq ft principal dwelling). Lot size: 7,700 sq ft.

Based on listing data, which indicates the property type — not the zoning district. Local dimensional, septic (Title 5), and historic-district requirements still apply. Not legal advice — verify with the municipality.

Full Winchester, MA market report ZIP 01890 market data

Listing Provided By

Listing Agent: Justin Blankenship

Listing Office: Hartley Realty Group

MLS® Number: 73541288