66 Windsor Rd
Wellesley, MA 02481
- 5 Beds
- 6 Baths
- 5,026 sqft (on 0.57 acres)
5 Beds
6 Baths
5,026 sqft
(on 0.57 acres)
Local Information
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Description
An exceptional property set in one of Wellesley's most sought after locations. Abutting Centennial Park and in the heart of the Wellesley Country Club area, this gorgeous home has it all. The sensational two-story family room has a grand stone fireplace and a wall of windows that provides sweeping views of glorious grounds through every season. The generous-sized kitchen has rich wood cabinetry, an expansive center island and a breakfast area that is filled with natural light and views. There is a front-to- back living room with fireplace and built-ins, an elegant dining room and a study. Each of the bedrooms are spacious and three are ensuite, including the master with its four walk in closets and tastefully designed bath. The finished lower level has two playrooms and a workshop area. This very special property is complete with a three-car garage and central air conditioning . This is a home to treasure! Close to shops, the train and restaurants.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.
Home Highlights
Parking
No Info
Outdoor
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
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Listed
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Home Details for 66 Windsor Rd
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Heating & Cooling Heating: Other, GasAir ConditioningHeating Fuel: Other |
Levels, Entrance, & Accessibility Stories: 2 |
Interior Details Number of Rooms: 11 |
Fireplace & Spa Fireplace |
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Year Built Year Built: 1930Year Updated: 1999 |
Property Type / Style Property Type: Single Family HomeArchitecture: Colonial |
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Exterior Home Features Exterior: Wood |
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Units in Building: 1 |
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Lot Area: 0.57 acres |
Price History for 66 Windsor Rd
| Date | Price | Event | Source |
|---|---|---|---|
| 08/03/2021 | $2,750,000 | Sold | MLS PIN #72830323 |
| 08/10/2018 | $2,400,000 | Sold | N/A |
| 05/30/2018 | $2,549,000 | PriceChange | Agent Provided |
| 05/13/2018 | $2,695,000 | PendingToActive | Agent Provided |
| 05/13/2018 | $2,695,000 | Pending | Agent Provided |
| 05/02/2018 | $2,695,000 | Listed For Sale | Agent Provided |
| 05/17/1994 | $695,000 | Sold | N/A |
Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $31,498 |
| Assessment | $3,064,000 |
Home facts updated by county records
Comparable Sales for 66 Windsor Rd
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.08 | Single-Family Home | $2,900,000 | 07/24/25 | 4 | 4.5 | 3,272 | |
0.10 | Single-Family Home | $2,600,000 | 01/09/26 | 4 | 3.5 | 3,705 | |
0.37 | Single-Family Home | $3,600,000 | 10/22/25 | 6 | 5.5 | 5,900 | |
0.44 | Single-Family Home | $2,833,000 | 05/19/26 | 4 | 3.5 | 4,151 | |
0.61 | Single-Family Home | $3,300,000 | 08/08/25 | 6 | 5.5 | 4,897 | |
0.60 | Single-Family Home | $2,354,000 | 12/24/25 | 4 | 4.5 | 4,211 | |
0.53 | Single-Family Home | $2,335,000 | 07/01/25 | 5 | 3.5 | 4,635 | |
0.52 | Single-Family Home | $3,585,000 | 06/16/25 | 6 | 4.5 | 5,317 | |
0.64 | Single-Family Home | $2,350,000 | 07/30/25 | 4 | 4.5 | 4,300 | |
0.35 | Single-Family Home | $6,187,500 | 11/12/25 | 6 | 7 | 7,037 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.Assigned Schools
These are the assigned schools for 66 Windsor Rd.
What Locals Say about Wellesley
At least 123 Trulia users voted on each feature.
92 % Say it's dog friendly
87 % Say parking is easy
85 % Say people would walk alone at night
84 % Say yards are well-kept
80 % Say car is needed
79 % Say there are sidewalks
76 % Say kids play outside
76 % Say there's holiday spirit
74 % Say streets are well-lit
73 % Say there's wildlife
72 % Say it's quiet
70 % Say they plan to stay for at least 5 years
67 % Say it's walkable to restaurants
66 % Say neighbors are friendly
65 % Say there are community events
62 % Say it's walkable to grocery stores
Sourced by Trulia users. Learn more about our methodology.
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66 Windsor Rd, Wellesley, MA 02481 is a 5 bedroom, 7 bathroom, 5,026 sqft single-family home built in 1930. This property is not currently available for sale. 66 Windsor Rd was last sold on Aug 3, 2021 for $2,750,000. The current Trulia Estimate for 66 Windsor Rd is $4,213,000.

