55 Chestnut St
Waltham, MA 02493
- 5 Beds
- 8 Baths
- 8,567 sqft (on 1.43 acres)
5 Beds
8 Baths
8,567 sqft
(on 1.43 acres)
Local Information
-- mins to
Home Highlights
Property Type
Single-Family Home
Year Built
1964
Lot Size
1.43 acres
Living Area
8,567 sqft
Price/Sqft
$799
Parking
Garage
About this House
On one of the most exclusive streets in Weston, this Colonial masterpiece, expanded and gut renovated by a custom builder in 2007 showcases exquisite quality details such as custom moldings and cabinetry throughout. Designed by top architects, it provides the perfect harmony between casual living and formal entertaining. The vast, open kitchen and family room, plus sunroom with views over the lush back yard, offer rooms for casual relaxation. The breathtaking galleried game room with Crotch Mahogany paneling, elegant dining room, living room and double-height foyer afford the home grand spaces for entertaining. A paneled office with gas fireplace completes the first floor. The luxurious master suite, with 2 walk-in closets, gas fireplace and balcony are on the second floor, along with 3 further bedroom suites. The 5th bedroom suite and large gym are on the 3rd floor. A playroom over the 3-car garage overlooks the sport court and the basement has a media room plus exquisite wine cellar.
55 Chestnut St, Waltham, MA 02493 is a 5 bedroom, 9 bathroom, 8,567 sqft single-family home built in 1964. It last sold for $5,100,000 on Jun 10, 2021. It is currently off market. The Trulia Estimate is $6,848,400, with a rent estimate of $5,663/month.
Home Details for 55 Chestnut St
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Interior Details BasementNumber of Rooms: 13Ceiling Fan |
Heating & Cooling Heating: Baseboard, Forced Air, Radiant, GasAir ConditioningCooling System: CentralHeating Fuel: Baseboard |
Levels, Entrance, & Accessibility Stories: 2Floors: Tile, Carpet, Hardwood, Slate |
Appliances & Utilities Cable ReadyDishwasherDisposalDryerMicrowaveRefrigeratorWasher |
Fireplace & Spa Fireplace |
Security Security System |
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Exterior Home Features Roof: AsphaltDeckExterior: StonePatioPorchSprinkler System |
Parking & Garage GarageParking Spaces: 10Parking: Garage Attached |
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Year Built Year Built: 1964 |
Property Type / Style Property Type: Single Family HomeArchitecture: Colonial |
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Units in Building: 1 |
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Lot Area: 1.43 acres |
Price History for 55 Chestnut St
| Date | Price | Event | Source |
|---|---|---|---|
| 06/10/2021 | $5,100,000 | Sold | N/A |
| 03/22/2021 | $5,495,000 | Pending | MLS PIN #72778754 |
| 03/17/2021 | $5,495,000 | Contingent | MLS PIN #72778754 |
| 01/26/2021 | $5,495,000 | Listed For Sale | MLS PIN #72778754 |
| 01/17/2021 | ListingRemoved | MLS PIN #72676299 | |
| 06/18/2020 | $5,495,000 | Listed For Sale | Agent Provided |
| 11/25/2019 | $5,995,000 | ListingRemoved | Agent Provided |
| 04/03/2019 | $5,995,000 | Listed For Sale | Agent Provided |
| 04/16/2004 | $2,125,000 | Sold | N/A |
| 10/17/1988 | $875,000 | Sold | N/A |
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
Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $60,575 |
| Assessment | $5,457,200 |
Home facts updated by county records
Comparable Sales for 55 Chestnut St
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.16 | Single-Family Home | $3,350,000 | 08/29/25 | 5 | 5 | 6,252 | |
0.28 | Single-Family Home | $7,255,000 | 10/02/25 | 5 | 6.5 | 8,205 | |
0.81 | Single-Family Home | $4,900,000 | 06/11/26 | 5 | 7 | 8,363 | |
0.19 | Single-Family Home | $11,000,000 | 12/04/25 | 7 | 10 | 12,120 | |
0.55 | Single-Family Home | $6,600,000 | 03/31/26 | 5 | 7.5 | 11,300 | |
0.88 | Single-Family Home | $5,700,000 | 12/02/25 | 5 | 6 | 8,210 | |
0.49 | Single-Family Home | $2,600,000 | 11/17/25 | 5 | 3.5 | 5,100 | |
0.93 | Single-Family Home | $3,750,000 | 01/15/26 | 6 | 6.5 | 9,064 | |
0.48 | Single-Family Home | $1,930,000 | 08/22/25 | 4 | 3 | 3,760 | |
1.23 | 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.Assigned Schools
These are the assigned schools for 55 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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