166 Winding River Rd, Wellesley, MA 02482
OFF MARKET

166 Winding River Rd
Wellesley, MA 02482

  • 4 Beds
  • 3.5 Baths
  • 5,450 sqft (on 1.25 acres)

$3,928,800

Trulia Estimate
as of Jun 7, 2026
Est. Refi. Payment $22,889/mo*

$3,928,800

Trulia Estimate
as of Jun 7, 2026
Est. Refi. Payment $22,889/mo*
4 Beds
3.5 Baths
5,450 sqft
(on 1.25 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

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

Interior Features

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 Features

Exterior Home Features
Roof: AsphaltDeckExterior: StuccoPatioSprinkler System
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Property Information

Year Built
Year Built: 1963
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 1.25 acres

Price History for 166 Winding River Rd

DatePriceEventSource
08/17/2020$2,785,000Sold
N/A
06/17/2020$2,785,000PriceChange
Agent Provided
05/27/2020$2,925,000Listed For SaleAgent Provided
11/09/2004$2,040,000Sold
N/A
07/19/1989$892,500Sold
N/A

Market trends in Wellesley

Last updated April 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
Sale-to-List Price
Price per sq ft
Available listings
108
6
MoM
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Property Tax and Assessment

Year2025
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

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Assigned Schools

These are the assigned schools for 166 Winding River Rd.
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

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.
  • Mike Holiday
    "Everyone walks their dogs and lets their dogs say hello, most often. People know each other. It’s a great community"
  • Emilyperrottet
    "Nothing. It’s a changing neighborhood with a mix of old and new homes. Most of the homes are old and run down. "
  • Emilyperrottet
    "I take the Commuter rail from Wellesley to the T subway. 1.5 hours to Cambridge from south station. "
  • Trulia User
    "Lots of trails and other dogs in the area, many pet stores in the area as well. Dogs are well behaved and friendly. "
  • Shirley L.
    "The walking paths and yearly town celebrations are wonderful! A great sense of community and great schools. "
  • Sdipietro369
    "I am a visitor to this area. The neighborhood seems very nice with Babson College right around the corner. Shops within a close distance. "
  • Katrina C.
    "You feel you're kids are safe here in town. Everyone is friendly and we're all neighbors. It's a lovely town with a community feeling. "
  • Jamie.solomon1
    "I lived in Weston for two years and it’s a delightful town, with gorgeous land and large houses. Usually at least an acre"
  • Cmt138
    "Great access to commuter rail from either Wellesley Square or Wellesley Hills. Easy 10-15 min walk. Better parking from Wellesley Square. Usually takes about 1/2 hour to Back Bay. Driving into Boston can take a little more time with traffic to cross town to Mass Pike."
  • Laura M.
    "There are lots of dogs in our neighborhood- people walk them all the time. Dogs are welcome at Morse’s pond in the off season. "
  • Bruce C.
    "Lots of other dog owners who walk their dogs all the time. Also plenty of space to run with dogs on a trail or away from streets. "
  • Keith S.
    "Lots of trails and public spaces. Nationally acclaimed colleges. Variety of great shops and restaurants."
  • Srodousakis
    "Wellesley is a beautiful but very privileged neighborhood. It is very safe and people are friendly. Schools are great! There is a cute downtown and generally it’s a great place to raise kids. "
  • Molly R.
    "i love my neighborhood. everyone is so kind and welcoming. we often times have little gatherings or block parties. everyone knows each other and we are a very close community. "
  • Victoria V.
    "That I live on route 16 and nobody lets me out of my driveway in the morning and I have to leave for work an hour early just because of that."

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Homes for sale near 166 Winding River Rd

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Off Market Homes Near 166 Winding River Rd

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Homes for rent near 166 Winding River Rd

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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.