Single Family for Sale: 2 Chestnut St, Winchester, MA 01890

6 beds
5 full baths
5,500 sqft
$3,599,000
$3,599,000
2 Chestnut St, Winchester, MA 01890
6 beds
5 full baths
5,500 sqft
$3,599,000
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Price:
$3,599,000

Type Single Family
Style Colonial
Beds 6
Baths 5 full baths
Square Feet 5,500 sqft
Garage Spaces 2
Lot Size 0.25 acres
Year Built 2025

City Winchester
County Middlesex

MLS 73333668
Status Active
DOM 10 days
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

Room Features

Bathroom 1 8 x 5 First Floor
Bathroom 2 14 x 12 Second Floor
Bathroom 3 12 x 6 Second Floor
Bedroom 2 14 x 13 Second Floor
Bedroom 3 14 x 11 Second Floor
Bedroom 4 17 x 12 Second Floor
Bedroom 5 14 x 14 Third Floor
Dining Room 15 x 11 First Floor
Kitchen 18 x 15 First Floor
Living Room 20 x 16 First Floor
Master Bedroom 20 x 16 Second Floor
Office 14 x 13 Basement Floor

Lot & Building Features

Appliances Electric Water Heater
Construction Frame
Cooling Central Air, Heat Pump
Heating Central, Electric
Sewer Public Sewer
Tax Year 2025
Taxes Paid $15,641
Water Public
Foundation Concrete Perimeter
Exterior Features Decorative Lighting, Stone Wall, Sprinkler System, Professional Landscaping, Patio
Interior Features Bathroom - Full, Study, Play Room, Office, Mud Room, Exercise Room, Bedroom, Bathroom - Tiled With Shower Stall
Roof Shingle
Full Baths 5
Parking Attached, Off Street
Total Rooms 15
Basement Feature Full, Walk-Out Access, Partially Finished
Garage Spaces 2
Fireplaces 1

Price History of 2 Chestnut St, Winchester, MA

Date Name Price Difference
02/09/2025 Listing Price $3,599,000 N/A
*Information provided by REWS for your reference only. The accuracy of this information cannot be verified and is not guaranteed.

Comparable Properties Sold Near By

Low
$2,550,000
$465 / sqft
Average
$2,887,333
$523 / sqft
High
$3,800,000
$691 / sqft

Address City Zip Beds Baths Price Sq. Ft. $/SQFT Sold Date
This Listing Winchester 01890 6 5.0 $3,599,000 5,500 $654 N/A
1 Alice Lane Winchester 01890 6 5.5 $2,625,000 5,524 $475 07/30/2024
19 Socrates Way Winchester 01890 5 5.0 $2,650,000 5,678 $467 06/03/2024
44 Thornberry Rd Winchester 01890 5 5.5 $2,550,000 5,486 $465 05/13/2024
35 Kensington Park Arlington 02476 5 5.5 $2,599,000 5,323 $488 06/28/2024
6 Pocahontas Dr Winchester 01890 5 5.5 $3,100,000 5,600 $554 10/03/2024
25 Ledgewood Rd Winchester 01890 5 4.5 $3,800,000 5,500 $691 12/03/2024

Map of 2 Chestnut St, Winchester, MA

Location Map Street View
Photo of Karen Lopilato
Karen Lopilato
Principal Broker/Owner
Direct: 603-553-4334
Office
185 Plaistow Road, Suite 1
Plaistow, NH 03865
603-382-0360 x11
Listed by Advisors Living - Winchester, Mark Donnellan
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2 Chestnut St (MLS #73333668) is a colonial single family home located in Winchester, MA. This single family home is 5,500 sqft and on a lot of 11,090 sqft (or 0.25 acres) with 6 bedrooms and 5 baths. This property was listed on 02/09/2025 and has been priced for sale at $3,599,000.

The 5 bedroom single family home at 25 Ledgewood Rd in Winchester is nearby and sold for $3,800,000 on 12/03/2024. Another nearby 6 bedroom single family home, 1 Alice Lane in Winchester sold for $2,625,000 on 07/30/2024.

Nearby zip codes are 01244, 01801, 02144, 02155 and 02474. This property neighbors other cities such as Arlington, Medford, Somerville, Stoneham and Woburn.

MLS PIN

Listing Last updated . Some properties which appear for sale on this web site may subsequently have sold or may no longer be available. Walk Score map and data provided by Walk Score. Google map provided by Google. Bing map provided by Microsoft Corporation.

All information provided is deemed reliable but is not guaranteed and should be independently verified.

Listing information courtesy of: Advisors Living - Winchester

The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information are for the personal, non commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein.