100 Chestnut St
Weston, MA 02493
5 Beds
6.5 Baths
8,205 sqft (on 3.39 acres)
5 Beds
6.5 Baths
8,205 sqft
(on 3.39 acres)
Local Information
- Map ViewExplore the area around 100 Chestnut St.
- Schools2 Preschool Schools3 Elementary Schools1 Middle School1 High School
- Shop & Eat
-- mins to
Home Highlights
Property Type
Single-Family Home
Year Built
1992
Lot Size
3.39 acres
Living Area
8,205 sqft
Price/Sqft
$909
Parking
3 Car Garage
About this House
100 Chestnut Street is the epitome of New England privacy & elegance. This estate is nestled on 3.3 secluded acres in scenic Weston. The home offers the charm of rolling landscapes, stone walls, and lush gardens. Designed by Royal Barry Wills & extensively renovated, this home showcases stunning interiors with 10'-14' ceilings, a Christopher Peacock kitchen, limestone fireplaces, herringbone oak floors, & French doors leading to blue stone terraces. The expertly crafted layout features a secluded ground-floor primary suite as well as expansive 2nd-floor bedrooms, ideal for both family living & entertaining. Surrounded by hundreds of acres conservation land, the property boasts exceptional amenities including a tennis court, pool, and expansive lawns. Enjoy access to pristine trails for hiking, biking & horseback riding. Located just 20 minutes from Boston and minutes from Weston Center, this smart home with Control 4 automation promises modern convenience in a picturesque setting.
100 Chestnut St, Weston, MA 02493 is a 5 bedroom, 7 bathroom, 8,205 sqft single-family home built in 1992. It last sold for $7,255,000 on Oct 2, 2025 (9% below the $7,995,000 asking price). It is currently off market. The Trulia Estimate is $7,456,800, with a rent estimate of $19,413/month.
Home Details for 100 Chestnut St
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Interior Details Number of Rooms: 13Types of Rooms: Master Bathroom |
Beds & Baths Number of Bedrooms: 5Number of Bathrooms: 7Number of Bathrooms (full): 6Number of Bathrooms (half): 1 |
Dimensions and Layout Living Area: 8205 Square Feet |
Heating & Cooling Heating: Forced Air,Natural GasHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air |
Fireplace & Spa Number of Fireplaces: 4Has a FireplaceNo Spa |
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Exterior Home Features Patio / Porch: Patio, EnclosedExterior: Patio, Patio - Enclosed, Pool - Inground Heated, Tennis Court(s), Garden, Stone WallFoundation: Concrete PerimeterGardenHas a Private Pool |
Parking & Garage Number of Garage Spaces: 3Number of Covered Spaces: 3Open Parking Spaces: 5No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 8Parking: Attached,Driveway |
Pool Pool: Pool - Inground HeatedPool |
Frontage Not on Waterfront |
Water & Sewer Sewer: Public Sewer |
Finished Area Finished Area (above surface): 8205 |
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Year Built Year Built: 1992 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Cape |
Building Not Attached PropertyDoes Not Include Home Warranty |
Property Information Parcel Number: M:031.0 L:0006 S:000.0, 868171 |
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Price List Price: $7,995,000 |
Status Change & Dates Off Market Date: Thu Sep 25 2025 |
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MLS Status: Sold |
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Direction & Address City: Weston |
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Building Area Building Area: 8205 Square Feet |
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Not Senior Community |
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No HOA |
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Lot Area: 3.3874 Acres |
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Contingencies: Pending P&S |
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Mls Number: 73433821Above Grade Unfinished Area: 8205 |
Last check for updates: about 2 hours ago
Listed by The Mazer Group, (617) 905-7379
Compass, (617) 206-3333
Allison Mazer, (617) 905-7379
Bought with: Antonio Khoury, (781) 385-1695, Compass, (617) 206-3333
Source: MLS PIN, MLS#73433821
Price History for 100 Chestnut St
| Date | Price | Event | Source |
|---|---|---|---|
| 10/02/2025 | $7,255,000 | Sold | MLS PIN #73433821 |
| 09/23/2025 | $7,995,000 | Contingent | MLS PIN #73433821 |
| 09/22/2025 | $7,995,000 | Listed For Sale | MLS PIN #73433821 |
| 08/19/2025 | $7,995,000 | ListingRemoved | MLS PIN #73331634 |
| 06/04/2025 | $7,995,000 | PriceChange | MLS PIN #73331634 |
| 02/03/2025 | $8,395,000 | Listed For Sale | MLS PIN #73331634 |
| 11/30/2024 | $8,885,000 | ListingRemoved | MLS PIN #73275020 |
| 08/07/2024 | $8,885,000 | Listed For Sale | MLS PIN #73275020 |
| 02/10/2015 | $4,150,000 | Sold | N/A |
| 12/22/2014 | $4,750,000 | Pending | Agent Provided |
| 12/12/2014 | $4,750,000 | PriceChange | Agent Provided |
| 08/28/2014 | $4,975,000 | PriceChange | Agent Provided |
| 06/27/2014 | $5,295,000 | PriceChange | Agent Provided |
| 05/08/2014 | $5,700,000 | Listed For Sale | Agent Provided |
Market trends in Weston
Last updated June 2026
Avg. sale price
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Sale-to-List Price
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Price per sq ft
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Available listings
62
8MoM
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Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $64,826 |
| Assessment | $5,840,200 |
Home facts updated by county records
Comparable Sales for 100 Chestnut St
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.38 | Single-Family Home | $6,600,000 | 03/31/26 | 5 | 7.5 | 11,300 | |
0.60 | Single-Family Home | $5,700,000 | 12/02/25 | 5 | 6 | 8,210 | |
0.56 | Single-Family Home | $4,900,000 | 06/11/26 | 5 | 7 | 8,363 | |
0.41 | Single-Family Home | $3,350,000 | 08/29/25 | 5 | 5 | 6,252 | |
0.47 | Single-Family Home | $11,000,000 | 12/04/25 | 7 | 10 | 12,120 | |
0.68 | Single-Family Home | $3,750,000 | 01/15/26 | 6 | 6.5 | 9,064 | |
0.80 | Single-Family Home | $3,500,000 | 03/30/26 | 5 | 5.5 | 5,409 | |
0.76 | Single-Family Home | $3,287,500 | 08/22/25 | 5 | 3.5 | 6,461 | |
1.16 | Single-Family Home | $7,180,000 | 06/24/26 | 6 | 7.5 | 8,421 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.
FOR SALE1.39 ACRESRosemary McCready, Compass
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Assigned Schools
These are the assigned schools for 100 Chestnut St.
- Field Elementary School
- 4-5
- Public
- 337 Students
8/10GreatSchools RatingParent Rating AverageMy daughter has completed the first half of fourth grade, and we've been impressed with the principal, her homeroom teacher, teacher specialists, and the beautiful school facility itself. Field Elementary has some of the highest math scores in the state, and we particularly like the emphasis on social- emotional learning, which leverages the Responsive Classroom approach. The engagement of parents, in support of the teachers, is extremely strong.Parent Review6y ago - Weston Middle School
- 6-8
- Public
- 454 Students
9/10GreatSchools RatingParent Rating AverageWeston is amazing. They give so many resources to students. Not only that, there are a lot of after-school activities you can do, and they also offer transportation till 5:30. For example, there is a swimming pool at the Weston Middle School where the Weston swim teams train in every weekOther Review10mo ago - Country Elementary School
- PK-3
- Public
- 335 Students
10/10GreatSchools RatingParent Rating AverageOur kids have had an extremely positive experience at Country. We love the teachers and the principal.Parent Review2y ago - Weston High School
- 9-12
- Public
- 651 Students
10/10GreatSchools RatingParent Rating AverageThis school keeps declining due to a SC that continues to be comprised of parents who only want to please school administration. The relationship between the school committee and the superintendent is troubling, to say the least. The superintendent is completely uninterested in doing what is best for the students and Only rains to do what is easiest for her and for the teachers. She was unqualified and hastily appointed when no other candidates accepted the job. Think twice before moving here for the school system. Things look good on the surface but all parents here have their children individually tutored and/or send them to enrichment classes to keep them up to speed. It’s a town and a school system with a lot of money but not a lot of academic rigor. Simply look at some of the department heads and how pedestrian they are. It seems if you have enough years as a teacher you automatically get promoted and are responsible for running a department ( with no experience!) and making important decisions that negatively impact the student community. There are many good school systems out there: Wellesley, Newton, Brookline and Wayland to name a few. Do your research. Don’t bother talking to school committee members because they will just feed you some tired, prepared line. Look very closely at the test scores. Weston falls short.Parent Review3y ago - Woodland Elementary School
- PK-3
- Public
- 302 Students
10/10GreatSchools RatingParent Rating AverageGreat school with supportive teachers and parents.Parent Review6y ago 
Check out schools near 100 Chestnut St.
What Locals Say about Weston
At least 28 Trulia users voted on each feature.
90 % Say car is needed
85 % Say it's dog friendly
82 % Say it's quiet
80 % Say parking is easy
77 % Say people would walk alone at night
76 % Say there's holiday spirit
74 % Say they plan to stay for at least 5 years
73 % Say yards are well-kept
71 % Say there's wildlife
52 % Say kids play outside
50 % Say neighbors are friendly
44 % Say there are community events
38 % Say there are sidewalks
33 % Say it's walkable to grocery stores
29 % Say streets are well-lit
26 % Say it's walkable to restaurants
Sourced by Trulia users. Learn more about our methodology.
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Homes for sale near 100 Chestnut St
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Off Market Homes Near 100 Chestnut St
SOLDJUL 29, 2026Melissa Dailey, Coldwell Banker Realty - Wellesley
SOLDJUL 24, 2026Donahue Maley and Burns Team, Compass
SOLDJUL 22, 2026Bobby Morgenstern, Gibson Sotheby's International Realty
SOLDJUL 21, 2026Marc Charney, eXp Realty LLC - Corporate Office
SOLDJUL 8, 2026The Lara & Chelsea Collaborative, Coldwell Banker Realty - Wellesley
SOLDJUL 8, 2026The Shulkin Wilk Group, Compass
SOLDJUL 8, 2026Felicia Captain, Coldwell Banker Realty - Wellesley
SOLDJUL 7, 2026Melissa Dailey, Coldwell Banker Realty - Wellesley
SOLDJUN 30, 2026Collin Sullivan, William Raveis R.E. & Home Services
SOLDJUN 29, 2026Bell Petrini Group, Coldwell Banker Realty - Wellesley- See more homes for sale inWeston
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.
The MLS listing information displayed is deemed reliable, but is not guaranteed accurate by the MLS.
The MLS listing information displayed is deemed reliable, but is not guaranteed accurate by the MLS.