166 Winding River Rd
Wellesley, MA 02482
- 4 Beds
- 3.5 Baths
- 5,450 sqft (on 1.25 acres)
4 Beds
3.5 Baths
5,450 sqft
(on 1.25 acres)
Local Information
© Google
-- mins to
Description
Sited on over an acre of land with exquisite gardens and overlooking the Charles River, this custom-built European manor manages to provide sophisticated entertaining spaces with the warmth of a cherished family home. Renovated to perfection, this 10 room, 4 bedroom residence offers a gracious and flexible layout complete with an oversized living room boasting 12ft ceilings and large enough to host any event. A sun-filled chef's kitchen opens to a fireplaced family room and beautiful sun-room which both lead to a bluestone patio overlooking a private, fenced yard. The dining room, custom-paneled study, laundry and bedroom suite complete the first-floor. Three additional bedrooms are found on the second floor including the most beautiful master bedroom complete with built-ins, sitting area, closet space galore and a gorgeous bath. Central Air, underground sprinklers and an oversized 2-car garage complete the picture. Don't miss this very special property.
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
Garage
Outdoor
Patio, Deck
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago
Home Details for 166 Winding River Rd
|
|---|
Heating & Cooling Heating: Baseboard, GasAir ConditioningCooling System: CentralHeating Fuel: Baseboard |
Levels, Entrance, & Accessibility Stories: 2Floors: Tile, Carpet, Hardwood |
Interior Details Number of Rooms: 9 |
Appliances & Utilities Cable ReadyDishwasherDisposalMicrowaveRefrigeratorWasher |
Fireplace & Spa Fireplace |
Security Security System |
|
|---|
Exterior Home Features Roof: AsphaltDeckExterior: StuccoPatioSprinkler System |
Parking & Garage GarageParking Spaces: 2Parking: Garage Attached |
|
|---|
Year Built Year Built: 1963 |
Property Type / Style Property Type: Single Family HomeArchitecture: Colonial |
|
|---|
Units in Building: 1 |
|
|---|
Lot Area: 1.25 acres |
Price History for 166 Winding River Rd
| Date | Price | Event | Source |
|---|---|---|---|
| 08/17/2020 | $2,785,000 | Sold | N/A |
| 06/17/2020 | $2,785,000 | PriceChange | Agent Provided |
| 05/27/2020 | $2,925,000 | Listed For Sale | Agent Provided |
| 11/09/2004 | $2,040,000 | Sold | N/A |
| 07/19/1989 | $892,500 | Sold | N/A |
Market trends in Wellesley
Last updated April 2026
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
108 6MoM
Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $30,604 |
| Assessment | $2,977,000 |
Home facts updated by county records
Comparable Sales for 166 Winding River Rd
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.12 | Single-Family Home | $4,375,000 | 11/17/25 | 5 | 5.5 | 7,000 | |
0.54 | Single-Family Home | $3,190,000 | 07/18/25 | 5 | 5.5 | 6,695 | |
0.70 | Single-Family Home | $2,545,000 | 07/24/25 | 4 | 4 | 5,400 | |
0.81 | Single-Family Home | $3,100,000 | 10/15/25 | 5 | 3.5 | 4,375 | |
0.87 | Single-Family Home | $2,675,000 | 08/18/25 | 5 | 5 | 5,900 | |
0.31 | Single-Family Home | $6,660,000 | 05/28/26 | 6 | 8.5 | 10,090 | |
0.87 | Single-Family Home | $2,600,000 | 08/21/25 | 4 | 2.5 | 3,620 | |
0.96 | Single-Family Home | $1,700,000 | 08/22/25 | 4 | 4.5 | 4,162 | |
0.66 | Single-Family Home | $5,489,000 | 01/09/26 | 7 | 7 | 8,257 | |
1.17 | Single-Family Home | $2,275,000 | 08/13/25 | 4 | 5.5 | 5,216 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.Assigned Schools
These are the assigned schools for 166 Winding River Rd.
What Locals Say about Wellesley
At least 124 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
75 % 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
63 % Say it's walkable to grocery stores
Sourced by Trulia users. Learn more about our methodology.
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections
Apartments for Rent
Explore by feature
Homes for sale near 166 Winding River Rd
Off Market Homes Near 166 Winding River Rd
Homes for rent near 166 Winding River Rd
166 Winding River Rd, Wellesley, MA 02482 is a 4 bedroom, 4 bathroom, 5,450 sqft single-family home built in 1963. This property is not currently available for sale. 166 Winding River Rd was last sold on Aug 17, 2020 for $2,785,000. The current Trulia Estimate for 166 Winding River Rd is $3,928,800.

