2 Chestnut St, Winchester MA 01890

Winchester, MA 01890
$3,450,000
Est. $18,362/month
6
Beds
5
Baths
5,500
Sq Ft
$627
Price/Sq Ft
0.25
Acres
2025
Year Built
Single Family Residence
Type
67
Days on Market
Closed Listed Sep 27, 2025 • MLS# 73333668

About this home

Welcome to 2 Chestnut Street, an exquisite new construction home in progress by Mark Stephen Development. Situated off coveted Main Street in one of Winchester’s most sought-after neighborhoods, this residence is thoughtfully designed to blend timeless charm with modern conveniences. The home will feature five spacious bedrooms, five full bathrooms, a first-floor office, and a basement offering flexible space for an additional office, playroom, exercise room, or living area. The open-concept kitchen will include premium appliances, a grand nine-foot island, and custom cabinetry, while the primary suite will boast luxurious his-and-her closets and a spa-like bathroom with a soaking tub and marble-tiled shower. A third-floor bonus space adds versatility. With mature landscaping providing privacy and a spacious patio for outdoor living, this property is conveniently located near Winchester town center, top-rated schools, offers easy access to Boston, and promises an unparalleled lifestyle

Sale Statistics

Sale Overview
Original List Price: $3,599,000
Final Sale Price: $3,450,000
Difference: $149,000 (-4.1%)
Performance Metrics
95.9%
List to Sale Ratio
Sold below asking price
67
Days on Market
Extended listing
Price per Square Foot Analysis
Original $/sq ft: $654
Sale $/sq ft: $627
This property sold for $627 per square foot
Sale Summary

This property sold for 4.1% below the original asking price.

The property spent 67 days on market before selling.

Facts & Features

Property Overview

Property Type
Single Family Residence
Property Category
Residential
Year Built
2025
Bedrooms
6
Full Bathrooms
5
Living Area
5,500 sq ft
Total Rooms
15

Interior Features

Flooring
Wood, Flooring - Stone/Ceramic Tile, Flooring - Hardwood, Flooring - Wall to Wall Carpet, Flooring - Wood
Heating
Central, Electric
Has Heating
Yes
Cooling
Central Air, Heat Pump
Has Cooling
Yes
Fireplace Features
Living Room
Has Fireplace
Yes
Number of Fireplaces
1
Appliances
Electric Water Heater
Interior Features
Bathroom - Full, Bathroom - Tiled With Shower Stall, Mud Room, Bedroom, Study, Play Room, Office, Exercise Room
Laundry Features
Flooring - Stone/Ceramic Tile, Second Floor
Basement Details
Full, Partially Finished, Walk-Out Access

Exterior & Structure

Construction Materials
Frame
Architectural Style
Colonial
Roof
Shingle
Foundation
Concrete Perimeter
Exterior Features
Patio, Professional Landscaping, Sprinkler System, Decorative Lighting, Stone Wall
Patio/Porch Features
Patio
Has Spa
No
Waterfront Property
No

Lot & Land

Lot Size
0.25 acres
Lot Size
11,090 sq ft
Lot Size Area
0.2500
Lot Features
Corner Lot

Parking & Garage

Garage Spaces
2
Has Garage
Yes
Attached Garage
Yes
Has Carport
No
Total Non-Garage Parking Spaces
2
Parking Features
Attached, Off Street
Covered Parking Spaces
2

Utilities & Systems

Water Source
Public
Sewer
Public Sewer

Community & HOA

HOA
No
Senior Community
No

Financial & Tax Information

Annual Tax Amount
$15,641
Tax Year
2025
Tax Assessed Value
$1,410,400
Parcel Number
M:005 B:0132 L:0,895591
Zoning
RDB

Additional Details

Year Built Source
Owner
Year Built Details
Actual
Attached Property
No
Disclosures
Listing agent is owner

Location

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Neighborhood

2 Chestnut St, Winchester MA 01890

Winchester, MA 01890

Walkability

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Schools

School information not available

Monthly Payment Calculator

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Estimated Monthly Payment $0

Payment Breakdown

Principal & Interest $0
Property Tax $1,303
Homeowners Insurance $200
PMI $0

Property History

Market Insights

56.1%
Price Range
69
Total Days on Market
1
Previous Sales

Property Timeline

Sold
Jun 26, 2025
$3,450,000
Property sold
Days on Market: 69
🏠
Listed for Sale
Feb 9, 2025
$3,599,000
Original listing
Agent: Mark Donnellan Office: Advisors Living - Winchester
Previous Transaction - MLS #73211061
Full transaction history available when tracking began
🏷️
Previously Sold
Jun 11, 2024
$1,580,000
MLS #73211061

Price & Status History

Date Event Price Change
Feb 9, 2025 New Listing Added $3,599,000
Jun 11, 2024 Sold $1,580,000

Market Statistics

Days on Market
67 days
Price per Sq Ft
$627

Tax History

Year Taxes Assessment
2025 $15,641 $1,410,400

Financial Details

Annual Property Tax
$15,641
Tax Year 2025
Assessed Value
$1,410,400

Listing Information

Listing Agent Mark Donnellan
Listing Office Advisors Living - Winchester
Agent MLS ID NB112231
Office MLS ID AN8756

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