Active
7 Days on market
257 Cross Street Winchester — Photo 1 of 40

257 Cross Street Winchester — Photo 1 of 40

$1,050,000

257 Cross Street, Winchester, MA 01890

Winchester, MA 01890

Beds

5

Baths

2.5

SqFt

2,801

Style

Single Family

Built

1960

Situated on a large,10k+ level corner lot with frontage on both Cross Street and Verplast Avenue! The upper level features a fireplaced living room w picture window, updated kitchen, three bedrooms, 1.5 baths, and a large sunroom overlooking the expansive backyard. The first level offers additional flexible living space with a kitchenette, living area, two bedrooms, laundry, and a full bath, providing great potential for an in-law setup, guest space, home offices, or extended living. The generous lot and existing footprint create an ideal opportunity to modernize the home, expand the living space, or explore future possibilities. Put your personal touch on this home and build some great equity! This property is full of potential and ready for its next chapter!

Market Value Analysis

This Property
Size (SqFt) →Price →
This Property$375/sqft
Local Avg (Winchester)$541/sqft
31% BelowMarket Average

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

Property Details

Financials

Original Price$1,050,000
Annual Taxes$9,849

Parking

Garage0
Off-Street4

Interior Specifications

Total Rooms10
Fireplaces3
Flooring--
BasementFull, Finished, Walk-Out Access, Interior Entry

Climate & Utilities

HeatingBaseboard, Oil
CoolingCentral Air
WaterPublic
SewerPublic Sewer

Building & Exterior

Construction--
RoofShingle
FoundationConcrete Perimeter
ZoningRG

Property & Lot

Acres0.24
SqFt Lot10,365
Lot FeaturesCorner Lot, Level

Amenities & Appliances

Range • Dishwasher • Refrigerator • Freezer

Neighborhood

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

Geography

Floorplan Breakdown

Structural Layout

First
Living RoomDining RoomMaster BedroomBedroom 2Bedroom 3Bathroom 1Bathroom 2
Basement
Family RoomBedroom 4Bedroom 5Bathroom 3
Main,First
Kitchen
Living Room
Lvl First

17 x 15

Flooring - Hardwood, Window(s) - Picture

Dining Room
Lvl First

20 x 13

Kitchen
Lvl Main,First

18 x 12

Flooring - Hardwood, Dining Area

Family Room
Lvl Basement

22 x 20

Master Bedroom
Lvl First

14 x 12

Bathroom - Half, Closet, Flooring - Hardwood

Bedroom 2
Lvl First

14 x 11

Bedroom 3
Lvl First

11 x 11

Closet, Flooring - Hardwood

Bedroom 4
Lvl Basement

17 x 11

Closet

Bedroom 5
Lvl Basement

14 x 10

Closet

Bathroom 1
Lvl First

12 x 7

Bathroom - Full

Bathroom 2
Lvl First

5 x 4

Bathroom - Half

Bathroom 3
Lvl Basement

9 x 6

Bathroom - Full

Property History

Listed
$1,050,000

Sep 2, 2026

MLS® 73571418

Sold
$488,000

Jan 19, 2011

MLS® 71176694

Listed
$499,990

Jan 8, 2011

MLS® 71176694

Expired
$1,800

May 5, 2010

MLS® 71028758

Listed
$1,800

Feb 5, 2010

MLS® 71028758

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: 900 sq ft (the lesser of 900 sq ft or half the 2,801 sq ft principal dwelling). Lot size: 10,365 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.

Listing Provided By

Listing Agent: Kim Covino & Co. Team

Listing Office: Compass

MLS® Number: 73571418

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