21 Chestnut St

12,120 Sq. Ft.
$908 / Sq. Ft.
12,120
Sq. Ft.
$908
per Sq. Ft.

Description

This modern estate is a seamless blend of striking architecture and luxurious design. A grand 2 story foyer with soaring ceilings and a dramatic staircase creates a stunning first impression, while walls of glass connect the home’s interior to the scenic outdoors. The main level features a gourmet kitchen with a hidden pantry, chef’s kitchen, and office nook, flowing into a spacious family room with expansive views of private grounds, ideal for a future pool. The primary suite offers a private retreat...This modern estate is a seamless blend of striking architecture and luxurious design. A grand 2 story foyer with soaring ceilings and a dramatic staircase creates a stunning first impression, while walls of glass connect the home’s interior to the scenic outdoors. The main level features a gourmet kitchen with a hidden pantry, chef’s kitchen, and office nook, flowing into a spacious family room with expansive views of private grounds, ideal for a future pool. The primary suite offers a private retreat with dual spa-like bathrooms, large dressing rooms and a sitting area. Secondary bedrooms feature en-suite baths and generous closets, providing comfort and privacy. The lower level is designed for recreation and relaxation featuring a bar, exercise room, sauna, wine room and flexible spaces for a home theater or golf simulator. Conveniently located just a short drive from Boston, this estate is a rare opportunity to own a thoughtfully designed home.
  1. Listed by Maggie Gold Seelig • MGS Group Real Estate LTD

Property Details for 21 Chestnut Street

Town
Weston
Area
MA-Weston
Architectural Style
Other (See Remarks)
Style
Other (See Remarks)
Garage Spaces
3
Parking Spaces
15.00
Parking Spaces Total
18
LISTING UPDATED: 12/04/2025 11:40 AM

Property Details for 21 Chestnut Street

StatusSold
MLS #73356415
Days on Market232
Taxes$86,268 / year
HOA Fees-
Compass TypeSingle Family
MLS TypeSingle Family / Detached
Year Built2025
CountyMiddlesex County

Location

Listing Courtesy of MGS Group Real Estate LTD, Maggie Gold Seelig

Sold By MGS Group Real Estate LTD, Maggie Gold Seelig

Add your commute

Building Information for 21 Chestnut Street

Stories-Year Built2025Building Size-Lot Size2.11 AC / 91,911 SF

Payment Calculator

$60,801 per month

30 year fixed, 6.15% Interest

Principal and Interest

$53,612

Property Taxes

$7,189

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 21 Chestnut Street

General Details
Property Details
  • Building Area Units: Square Feet
  • Community Features: Public Transportation, Walk/Jog Trails, Golf Course, Conservation Area, Highway Access, Private School, Public School
  • Current Financing: Cash
  • Living Area: 12120.0
  • SqFt with Basement: Yes
  • Property Attached: No
  • Single Family Type: Detached
  • Waterfront: No
  • Year Built Details: Actual
  • Year Built Source: Builder
Location/School
  • Grade School: Weston Elem
  • High School: Weston Hs
  • Middle School: Weston Ms
Features
Interior Features
  • Appliances: Gas Water Heater, Range, Dishwasher, Refrigerator, Vacuum System, Range Hood
  • Basement Features: Full, Finished, Interior Access, Garage Access
  • Num of Baths: 11.0
  • Num of Full Baths: 9
  • Num of Half Baths: 2
  • Bathrooms Total Decimal: 10.00
  • Bathrooms Total Integer: 11
  • FireplaceYN: Yes
  • Fireplaces: 4
  • Flooring: Tile, Marble, Hardwood
  • Interior Features: Central Vacuum, Sauna/Steam/Hot Tub, Elevator
  • Interior Features: Central Vacuum, Sauna/Steam/Hot Tub, Elevator
  • Laundry Features: Gas Dryer Hookup
  • Primary Bath: Yes
  • SpaYN: No
Exterior Features
  • Construction: Frame
  • Exterior Features: Patio, Rain Gutters, Sprinkler System, Decorative Lighting, Outdoor Gas Grill Hookup
  • Exterior Features: Sprinkler System, Decorative Lighting, Patio
  • Lot Description: Gentle Sloping, Level
  • Patio And Porch Features: Patio
  • Roof Material: Rubber
Parking Features
  • Attached Garage: Yes
  • Carport: No
  • Covered Spaces: 3.00
  • Garage: Yes
  • Garage Parking: Attached, Heated, Off-Street
  • Parking Features: Attached, Heated, Off-Street
  • Parking Features: Heated, Off-Street
Utilities
  • Cooling: Central Air
  • Cooling: Yes
  • Electric: Generator
  • Green Energy Efficient: Thermostat
  • Green Energy Generation: Solar
  • Heating: Natural Gas, Hydro Air
  • Heating: Yes
  • Sewer: Private Sewerage
  • Utility Connections: for Gas Range, for Gas Dryer, Outdoor Gas Grill Hookup
  • Water: Public, Private
Property Information
Property Info
  • Farm Land Area Units: Square Feet
  • WARRANTY: No
  • Lot Size Units: Acres
Tax Information
  • Tax ID: M:032.0 L:0019 S:000.0,868218
  • Assessments: $7,771,900
  • Book: 76330
  • Tax Year: 2025
  • Zoning: RES
Building / Association Information
Living Characteristics
  • Beds Total: 7
Other Building Characteristics
  • Foundation: Concrete Perimeter
  • Cooling Zones: 13
  • Heat Zones: 13
Complex & Association Information
  • Adult Community: No

Property History for 21 Chestnut Street

DateEvent & SourcePriceAppreciation
Dec 4, 2025

Sold

MLS PIN #73356415

$11,000,000
Nov 26, 2025

Under Agreement

MLS PIN #73356415

Nov 26, 2025

Contingent

MLS PIN #73356415

Sep 3, 2025

Price Change

MLS PIN #73356415

$12,895,000
Apr 8, 2025

Listed (Active)

MLS PIN #73356415

$13,850,000
Nov 22, 2024

Expired

MLS PIN #73212017

$13,850,000
Oct 1, 2024

Temporarily Withdrawn

MLS PIN #73212017

$13,850,000
May 2, 2024

Expired

MLS PIN #73082610

$3,999,000
Mar 13, 2024

Listed (Active)

MLS PIN #73212017

$13,850,000
Oct 26, 2023

Temporarily Withdrawn

MLS PIN #73082610

$3,999,000
Feb 28, 2023

Listed (Active)

MLS PIN #73082610

$4,995,000
Dec 9, 2022

Expired

MLS PIN #73012753

$12,500,000
Jul 15, 2022

Listed (Active)

MLS PIN #73012753

$12,500,000
Dec 21, 2021

Canceled

MLS PIN #72817133

$9,450,000
Apr 19, 2021

Listed (Active)

MLS PIN #72817133

$9,450,000
Dec 2, 2020

Sold

MLS PIN #72607140

$1,900,000
Jul 24, 2020

Under Agreement

MLS PIN #72607140

Jul 24, 2020

Contingent

MLS PIN #72607140

Jan 12, 2020

Listed (Active)

MLS PIN #72607140

$2,699,000
Nov 1, 2019

Canceled

MLS PIN #72460435

$1,998,000
Feb 20, 2019

Listed (Active)

MLS PIN #72460435

$2,200,000
Jan 18, 2019

Expired

MLS PIN #72312667

$6,250,000
Aug 6, 2018

Expired

MLS PIN #72256892

$2,275,000
Apr 20, 2018

Canceled

MLS PIN #72256897

$2,275,000
Apr 20, 2018

Listed (Active)

MLS PIN #72312667

$6,250,000
Nov 17, 2017

Listed (Active)

MLS PIN #72256897

$2,395,000
Nov 17, 2017

Canceled

MLS PIN #72072588

$2,585,000
Nov 17, 2017

Listed (Active)

MLS PIN #72256892

$2,395,000
Nov 17, 2017

Canceled

MLS PIN #72072601

$2,585,000
Sep 25, 2016

Expired

MLS PIN #71956352

$8,995,000
Sep 24, 2016

Listed (Active)

MLS PIN #72072601

$3,335,000
Sep 24, 2016

Listed (Active)

MLS PIN #72072588

$3,335,000
Feb 5, 2016

Listed (Active)

MLS PIN #71956352

$8,995,000
DateEvent & SourcePrice
12/04/2025

Sold

MLS PIN #73356415

$11,000,000
11/26/2025

Under Agreement

MLS PIN #73356415

11/26/2025

Contingent

MLS PIN #73356415

09/03/2025

Price Change

MLS PIN #73356415

$12,895,000
04/08/2025

Listed (Active)

MLS PIN #73356415

$13,850,000
11/22/2024

Expired

MLS PIN #73212017

$13,850,000
10/01/2024

Temporarily Withdrawn

MLS PIN #73212017

$13,850,000
05/02/2024

Expired

MLS PIN #73082610

$3,999,000
03/13/2024

Listed (Active)

MLS PIN #73212017

$13,850,000
10/26/2023

Temporarily Withdrawn

MLS PIN #73082610

$3,999,000
02/28/2023

Listed (Active)

MLS PIN #73082610

$4,995,000
12/09/2022

Expired

MLS PIN #73012753

$12,500,000
07/15/2022

Listed (Active)

MLS PIN #73012753

$12,500,000
12/21/2021

Canceled

MLS PIN #72817133

$9,450,000
04/19/2021

Listed (Active)

MLS PIN #72817133

$9,450,000
12/02/2020

Sold

MLS PIN #72607140

$1,900,000
07/24/2020

Under Agreement

MLS PIN #72607140

07/24/2020

Contingent

MLS PIN #72607140

01/12/2020

Listed (Active)

MLS PIN #72607140

$2,699,000
11/01/2019

Canceled

MLS PIN #72460435

$1,998,000
02/20/2019

Listed (Active)

MLS PIN #72460435

$2,200,000
01/18/2019

Expired

MLS PIN #72312667

$6,250,000
08/06/2018

Expired

MLS PIN #72256892

$2,275,000
04/20/2018

Canceled

MLS PIN #72256897

$2,275,000
04/20/2018

Listed (Active)

MLS PIN #72312667

$6,250,000
11/17/2017

Listed (Active)

MLS PIN #72256897

$2,395,000
11/17/2017

Canceled

MLS PIN #72072588

$2,585,000
11/17/2017

Listed (Active)

MLS PIN #72256892

$2,395,000
11/17/2017

Canceled

MLS PIN #72072601

$2,585,000
09/25/2016

Expired

MLS PIN #71956352

$8,995,000
09/24/2016

Listed (Active)

MLS PIN #72072601

$3,335,000
09/24/2016

Listed (Active)

MLS PIN #72072588

$3,335,000
02/05/2016

Listed (Active)

MLS PIN #71956352

$8,995,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 21 Chestnut Street

Taxable ValueLand$1,752,800Additions$6,019,100Total$7,771,900
Tax Record2025$86,268 ($7,189 / month)
Home Facts
Beds6Baths3.5Total Finished SqFt9,310 SqFtAbove Grade Finished SqFt9,310 SqFtStories2Lot Size91,799 SqFtStyleSingle Family ResidenceYear Built2023CountyMIDDLESEXAPNWEST M:032.0 L:0019 S:000.0Fireplace TypeHas Fireplace

Schools near 21 Chestnut Street

This home is within Weston School District.
Rating
School
Type
Grades
Distance
Public - PK to 3
Public - PK to 3
Public - 4 to 5
Public - 6 to 8
Rating
School
Distance
Country Elementary School
PublicPK to 3

Woodland Elementary School
PublicPK to 3

Field Elementary School
Public4 to 5

Weston Middle School
Public6 to 8

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of MGS Group Real Estate LTD, Maggie Gold Seelig

The property listing data and information, or the images, set forth herein were provided to MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS. The property listing data and information, and the images, 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., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the images, set forth herein.