258 Cross Street, Winchester MA 01890

Winchester, MA 01890 • Winchester Highlands

$999,900

Est. $6,055/month

4

Beds

2

Baths

1,719

Sq Ft

$582

Price/Sq Ft

0.18

Acres

1860

Year Built

Single Family Residence

Type

9 hours 44 minutes

Time on Market

Active Open House Listed Jun 24, 2026 • MLS# 73541288 Copied!

About this home

Welcome to 258 Cross Street, a masterfully updated Winchester Colonial blending timeless character, modern comfort, and everyday function. Set on a level, fenced corner lot, this 4 bed, 2 bath home offers endless outdoor opportunity to relax, entertain, play, or dine al fresco. Inside, hardwood floors, crown molding, arched openings, bay windows, and ornate detail bring warmth and personality. The modernized kitchen beams with natural light and features upgraded cabinetry, stone counters, stainless appliances, and gas cooking. Both full baths have been tastefully updated with the larger featuring a tiled stand up shower, free standing soaking tub and a double vanity. Four bedrooms across the upper levels create flexibility for growing families, guests, WFH, fitness, or hobbies. Brand new central AC, central heat, full basement with laundry, and 4-car parking add functionality. Minutes from downtown Winchester with the most scenic downtown around, lined with shops, dining and even the T

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Public Records

Current Owner

Owner CONNORS GRAYSON + KATHERINE BOOK

Mailing Address 258 CROSS ST, WINCHESTER, MA, 1890

Land Use

Use Code 101

Description Single Family

Zoning RG

Style OLD STYLE

Tax Information

Assessed Value $865,700

Assessment History

Year	Land	Building	Total	Change
FY2026	$533,600	$332,100	$865,700	—

Sale History

Date	Price	Book/Page
Jun 1, 2020	$699,000	74794/447

Building Permit History

Permit history not yet available for this municipality.

Municipal Context: WINCHESTER

Property Data Comparison

Discrepancies found between MLS and assessor records.

Field	Assessor	MLS	Match
Sqft	2,984	1,719	✗
Year built	1,860	1,860	✓

Match: address_exact (95.0% confidence) · Data as of Jun 1, 2026

Property Overview

Property Type

Single Family Residence

Listing Type

For Sale

Year Built

1860

Bedrooms

4

Full Bathrooms

2

Living Area

1,719 sq ft

Total Rooms

7

Open House Schedule

25

Jun

Thursday, June 25

4:30 PM - 5:30 PM EDT

27

Jun

Saturday, June 27

12:00 PM - 2:00 PM EDT

28

Jun

Sunday, June 28

12:00 PM - 2:00 PM EDT

Facts & Features

Central AC

Home Facts

Type Residential

Style Single Family Residence

Year Built 1860

Living Area 1,719 sq ft

Lot Size 0.18 acres

Bedrooms 4

Full Baths 2

Total Rooms 7

Interior

Heating Central, Forced Air

Cooling Central Air

Flooring Wood, Tile, Carpet, Hardwood

Appliances Gas Water Heater, Range, Dishwasher, Disposal, Microwave, Refrigerator, Freezer, Washer, Dryer

Fireplace None

Basement Full, Concrete, Unfinished

Laundry In Basement

Features Internet Available - Unknown

Exterior

Construction Frame

Architecture Colonial

Roof Shingle

Features Patio, Storage, Professional Landscaping, Fenced Yard, Garden

Pool None

Spa None

Fencing Fenced/enclosed, Fenced

Patio/Porch Patio

Parking

Features Off Street, Deeded, Paved

Total Spaces 4

Utilities

Electric None

Water Public

Sewer Public Sewer

Gas None

Other For Gas Range

Financial

Annual Tax $9,592

Assessed Value $865,700

Interior Features

Flooring: Wood, Tile, Carpet, Hardwood

Appliances: Gas Water Heater, Range, Dishwasher, Disposal, Microwave, Refrigerator, Freezer, Washer, Dryer

Interior Features: Internet Available - Unknown

Windows:

Basement: Full, Concrete, Unfinished

Laundry: In Basement

Security:

Construction & Materials

Style: Colonial

Year Built: 1860

Structure Type:

Exterior Materials: Frame

Roof: Shingle

Foundation: Stone

Heating, Cooling & Utilities

Heating: Central, Forced Air

Heating Zones: 1

Cooling: Central Air

Cooling Zones: 1

Hot Water:

Water Source: Public

Sewer: Public Sewer

Energy Features:

Exterior & Lot

Exterior Features: Patio, Storage, Professional Landscaping, Fenced Yard, Garden

Patio & Porch: Patio

Fencing: Fenced/Enclosed, Fenced

Other Structures:

Lot Features: Corner Lot, Level

Road Surface: Paved

Parking & Garage

Total Parking Spaces: 4

Parking Features: Off Street, Deeded, Paved

Location

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Neighborhood

Winchester Highlands

258 Cross Street, Winchester MA 01890

Winchester, MA 01890

Walkability

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Nearby Schools

School District

Winchester School District local

A+

✓ School Safety 2024-25

0.1% Very Low (Safest)

0.1% Suspensions 0.1% In-School

↓ 5.4% below state avg

E

Elementary Schools

3 schools

Acera School

0.2 mi

Grades K-08

A+

Muraco Elementary School

0.3 mi | #62 of 824 | Score: 61.6

Improved 62 spots from last year

+3.4 above state avg

352 students Diverse

Rising School Strong Attendance

Grades K-05

Creative Corner School Inc

0.5 mi

Grades PK-K

M

Middle Schools

3 schools

A+

McCall Middle School

1.1 mi | #16 of 352 | Score: 62.4

Dropped 3 spots from last year

+4.2 above state avg

1,036 students Diverse

Strong Attendance

Grades 06-08

B

John F Kennedy Middle School

1.9 mi | #176 of 352 | Score: 42.4

Improved 42 spots from last year

-15.8 below state avg

521 students Diverse

Rising School

Grades 06-08

C+

Daniel L Joyce Middle School

2.1 mi | #217 of 352 | Score: 39.5

Dropped 14 spots from last year

-18.7 below state avg

455 students Moderate

Grades 06-08

H

High Schools

3 schools

A+

Winchester High School

0.7 mi | #17 of 346 | Score: 73.6

Improved 18 spots from last year

+15.4 above state avg

1,404 students Diverse

20 sports • 2,818 athletes

Strong AP Program High Graduation Rate College Ready Curriculum Strong Athletics

Grades 09-12

B

Woburn High School

1.2 mi | #143 of 346 | Score: 56.1

Dropped 21 spots from last year

-2.1 below state avg

1,259 students Diverse

18 sports • 2,056 athletes

High Graduation Rate College Ready Curriculum Strong Athletics

Grades 09-12

A-

Stoneham High School

2.5 mi | #91 of 346 | Score: 61.0

Improved 37 spots from last year

+2.8 above state avg

599 students Moderate

17 sports • 1,334 athletes

High Graduation Rate Rising School College Ready Curriculum Strong Athletics

Grades 09-12

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95% Interest

Year 15

50/50

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Property History

Market Insights

39.2%

Price Range

2

Previous Sales

Property Timeline

🏠

Listed for Sale

Jun 24, 2026

$999,900

Original listing

Agent: Justin Blankenship Office: Fiv Realty Co

Previous Transaction - MLS #72585005

Full transaction history available when tracking began

🏷️

Previously Sold

Jun 1, 2020

$699,000

MLS #72585005

View Listing →

Previous Transaction - MLS #72380664

Full transaction history available when tracking began

🏷️

Previously Sold

Jan 25, 2019

$607,500

MLS #72380664

View Listing →

Date	Event	Price	Change	$/sqft	Details
06/24/2026	🏠 Listed for Sale	$999,900	-	-	Original listing
06/01/2020	🏷️ Previously Sold	$699,000	-	-	MLS #72585005
01/25/2019	🏷️ Previously Sold	$607,500	-	-	MLS #72380664

Price & Status History

Date	Event	Price	Change
Jun 24, 2026	New Listing Added	$999,900	—
Jun 1, 2020	Sold	$699,000	—
Jan 25, 2019	Sold	$607,500	—

Market Statistics

Time on Market

9 hours 44 minutes

Price per Sq Ft

$582

Tax History

Year	Taxes	Assessment
2026	$9,592	$865,700

Financial Details

Annual Property Tax

$9,592

Tax Year 2026

Assessed Value

$865,700

Elementary Schools

Middle Schools

High Schools

Monthly Payment Breakdown

Loan Summary

Listed for Sale

Previous Transaction - MLS #72585005

Previously Sold

Previous Transaction - MLS #72380664

Previously Sold

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258 Cross Street, Winchester MA 01890

About this home

Public Records

Current Owner

Land Use

Tax Information

Assessment History

Sale History

Building Permit History

Municipal Context: WINCHESTER

Property Data Comparison

Property Overview

Open House Schedule

Facts & Features

Home Facts

Interior

Exterior

Parking

Utilities

Financial

Interior Features

Construction & Materials

Heating, Cooling & Utilities

Exterior & Lot

Parking & Garage

Location

Neighborhood

Walkability

Nearby Schools

Elementary Schools

Middle Schools

High Schools

Monthly Payment Calculator

Monthly Payment Breakdown

Loan Summary

Rate Impact

Payment Over Time

Property History

Market Insights

Property Timeline

Listed for Sale

Previous Transaction - MLS #72585005

Previously Sold

Previous Transaction - MLS #72380664

Previously Sold

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Tax History

Financial Details

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