See Home Value
$1,580,000
● House - Off Market

2 Chestnut Street

Winchester, MA 01890
bedrooms
4 Beds
bathrooms
3 Baths, 1 Half Bath
square feet
3,171 Ft²
$9,611
Est. Monthly

About This Property

Top location close to Winchester Center! This 4 bd, 3.5 br home is situated on a generous lot, offering abundance of space & functional floor plan for multi-generational or au-pair living. Greeted by a sunlit interior, showcasing hardwood floors & a cozy fireplace, creating a warm & inviting atmosphere. Enjoy the well-appointed kitchen w granite countertops & breakfast bar w/seating open into the spacious dining room. This home has 2 primary suite options as well as a recent 3rd floor addition w a secondary family room or office space plus a large bedroom suite w full bath! You will love the fenced in yard & 2 car garage with direct entry into the mudroom & the lower level family room w fireplace and wall of windows. The lower level also offers a full br/laundry room. Enjoy all the space this great home offers w/ close proximity to town, schools, dining, shopping, the fells & more! LAN upgrade & little to no electricity bill w solar panels! Don't miss out on this highly desirable home!
Unit Size
3,171 Ft²
Days on Market
-
Land Size
0.25 acres
Price per sqft
$536
Property Type
House
Property Taxes
$1,268
HOA Dues
-
Year Built
1958

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Last updated: 4 months ago (MLSPIN #73211061)

Price History

Date / Event Date Event Price
Jun 26, 2025 Sold
Sold
Apr 5, 2025 In contract -
In contract
Feb 9, 2025 Listed $3,599,000
Listed
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
Dec 28, 2024 No longer available -
No longer available
Nov 11, 2024 Withdrawn -
Withdrawn
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Property Highlights

Garage
Parking Available
Air Conditioning
Fireplace

Building Info

Overview

    General

  • Year Built: 1958
  • Effective Year Built: 1958
  • Building Count: 1
  • Total Rooms: 9
  • Bedroom Count: 4
  • Bathroom Count: 4
  • Full Bathrooms: 3
  • Partial Bathrooms: 4
  • Building Condition: 3
  • Building Quality: 0
  • Construction Type: 6
  • Building Style: 42
  • Exterior Walls Type: 18
  • Interior Walls Type: 0
  • Roof Shape Type: 1
  • Roof Cover Type: 15
  • Floor Count: 200
  • Living Units: 1
  • Floor Cover: 0
  • Basement Type: 7
  • Basement Area: 1,508
  • Garage Type: 17
  • Parking Space Count: 2
  • Patio Type: 0
  • Porch Type: 0
  • Pool Type: 0

    Dimensions

  • Lot Size Square Feet: 11,090
  • Total Building Area: 3,272
  • Gross Building Area: 4,580
  • Building Area: 3,272
  • Building Area Measurement: L

    Heating and Cooling

  • Fireplace Count: 1
  • Air Conditioning: 0
  • Heating: 10
  • Heated Square Feet: 3,272
  • Heating Fuel Type: 6

    Utilities

  • Sewer System: 0
  • Water Service: 0

Building

  • Building Type: 0
  • Property Class: R
  • Land Acres: 0000000255
  • Standard Land Use Code: 1001
  • County Land Use Code: 101

Neighborhood

  • School District Name: Winchester School District
  • School Tax School District: WINCHESTER SD
  • Census Tract: 338500

Zoning

  • Zoning: RDB

Geography

  • Parcel: WINC M:005 B:0132 L:0
  • Block: 132
  • Municipality: WINCHESTER
  • Latitude: 42.445
  • Longitude: -71.1342

    Address

  • Full Address: 2 Chestnut St
  • Address - House Number: 2
  • Address - Street Name: Chestnut
  • Address - Suffix Type: St
  • State: MA
  • City Name: Winchester
  • Carrier Code: C016
  • 4-Digit Zip Code: 3019
  • Zip Code: 01890

Valuation

    Tax

  • Tax Year: 2024
  • Tax Amount: $1,521,500

    Appraisal Valuation

  • Standard Deviation: 0.177
  • Valuation Date: Mar 06, 2024
  • Confidence Score: 77
  • Final Value: 1,616,145
  • High Value: 1,902,103
  • Low Value: 1,330,186

    Assessments Valuation

  • Assessed Year: 2024
  • Assessed Total Value: $1,342,900
  • Assessed Land Value: $877,900
  • Assessed Improvements Value: $465,000

    Sales

  • Current Sale Recording Date: Nov 30, 2009
  • Current Sale Price:
  • Current Sale Document Type: 27
  • Current Sale Input Document Number: 00230364
Data used for valuation calculations is provided by RealtyHop, and other third party sources

Comparables

Unit
Status
Type
Beds
Baths
ft²
Price/ft²
Asking Price
Listed On
Closing Price
Sold On
HOA + Taxes

About Winchester Town Center


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Frequently Asked Questions

When was property at 2 Chestnut Street built and last sold?
The property at 2 Chestnut Street was built in 1958 and last sold on Jan 1, 1970 for $607,000.
How much is this home worth?
The estimated value of the home located at 2 Chestnut Street is $3,557,559.
What are some comparable homes to 2 Chestnut Street?
There are currently no comparable homes to 2 Chestnut Street.