166 Winding River Rd, Wellesley, MA 02482
Property image
Property image
OFF MARKET

$3,820,000

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

166 Winding River Rd, Wellesley, MA 02482

Est. Refi. Payment $22,759/mo*
Refinance Your Home
Currently Off Market - Sold Aug 17, 2020 for $2,785,000

Home Value

Trulia Estimate
$3.82M
Since last month
Decreased$44K (-1.1%)
Since last year
Increased$10K (+0.3%)
Since last sale
Increased$1M (+37.6%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +54% in the last 10 years
MonthEstimated value
2026
August 2026$3.83M
July 2026$3.88M
June 2026$3.94M
May 2026$3.93M
April 2026$3.84M
March 2026$3.86M
February 2026$3.72M
January 2026$3.66M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
193 Winding River Rd, Wellesley, MA
0.12
Single-Family Home
$4,375,000
11/17/25
5
5.5
7,000
389 Grove St, Needham, MA
0.38
Single-Family Home
$3,400,000
08/05/26
5
5.5
5,519
25 Longmeadow Rd, Wellesley, MA
0.46
Single-Family Home
$2,795,000
06/30/26
5
4.5
4,582
2 Kenilworth Rd, Wellesley, MA
0.81
Single-Family Home
$3,100,000
10/15/25
5
3.5
4,375
121 Livingston Rd, Wellesley, MA
0.31
Single-Family Home
$6,660,000
05/28/26
6
8.5
10,090
10 Colgate Rd, Wellesley, MA
0.76
Single-Family Home
$3,100,000
08/25/26
6
4.5
4,475
8 Warren Rd, Natick, MA
0.79
Single-Family Home
$2,210,000
07/30/26
4
4
4,030
78 Pheasant Landing Rd, Needham, MA
0.66
Single-Family Home
$5,489,000
01/09/26
7
7
8,257
1 Buckingham Ter, Wellesley, MA
0.76
Single-Family Home
$5,100,000
07/27/26
6
6.5
7,322
10 Cartwright Rd, Wellesley, MA
1.09
Single-Family Home
$2,535,000
10/31/25
4
4
4,282

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
193 Winding River Rd, Wellesley, MA 02482
0.12
$4,375,000
5
5.5
7,000
Recently Sold
198 Winding River Rd, Wellesley, MA 02482
0.15
$3,868,400
5
3.5
4,669
Off Market
12 Winding River Cir, Wellesley, MA 02482
0.19
$4,999,000
6
7
8,729
For Sale
80 Locust Ln, Needham, MA 02492
0.23
$3,385,000
7
5
5,969
For Sale
11 Winding River Cir, Wellesley, MA 02482
0.23
$3,384,500
5
4
4,125
Off Market
869 Charles River St, Needham, MA 02492
0.29
$1,756,200
4
2.5
3,879
Off Market
121 Livingston Rd, Wellesley, MA 02482
0.31
$6,660,000
6
8.5
10,090
Recently Sold
27 Locust Ln, Needham, MA 02492
0.34
$1,598,600
3
3
2,141
Off Market
389 Grove St, Needham, MA 02492
0.38
$3,400,000
5
5.5
5,519
Recently Sold
19 Ridge Hill Farm Rd, Wellesley, MA 02482
0.37
$2,750,900
2
3
2,930
Off Market
359 Grove St, Needham, MA 02492
0.41
$2,538,800
4
4.5
4,980
Off Market
430 Grove St, Needham, MA 02492
0.42
$2,519,000
7
5
6,658
Off Market

Local Information

  • Map ViewExplore the area around 166 Winding River Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1963
Lot Size
1.25 acres
Living Area
5,450 sqft
Price/Sqft
$701
Parking
Garage

About this House

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.
166 Winding River Rd, Wellesley, MA 02482 is a 4 bedroom, 4 bathroom, 5,450 sqft single-family home built in 1963. It last sold for $2,785,000 on Aug 17, 2020. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $3,820,000, with a rent estimate of $8,216/month.

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 and Tax history

DateEventPrice
Aug 17, 2020
Source: N/A
Sold
$2,785,000
Jun 17, 2020
Source: Agent Provided
PriceChange
$2,785,000
Price decreased by 5%
May 27, 2020
Source: Agent Provided
Listed For Sale
$2,925,000
Nov 9, 2004
Source: N/A
Sold
$2,040,000
Jul 19, 1989
Source: N/A
Sold
$892,500

Market trends in Wellesley

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$2.15M
$161KMoM
Sale-to-List Price
100.6%
0.4%MoM
Price per sq ft
$666
$18MoM
Available listings
87
25MoM

Around this home

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"
    0
    Flag
  • Emilyperrottet
    "Nothing. It’s a changing neighborhood with a mix of old and new homes. Most of the homes are old and run down. "
    0
    Flag
  • Emilyperrottet
    "I take the Commuter rail from Wellesley to the T subway. 1.5 hours to Cambridge from south station. "
    0
    Flag
  • 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. "
    0
    Flag
  • Shirley L.
    "The walking paths and yearly town celebrations are wonderful! A great sense of community and great schools. "
    0
    Flag
  • 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. "
    3
    Flag
  • 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. "
    2
    Flag
  • 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"
    1
    Flag
  • 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."
    2
    Flag
  • 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. "
    1
    Flag
  • 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. "
    1
    Flag
  • Keith S.
    "Lots of trails and public spaces. Nationally acclaimed colleges. Variety of great shops and restaurants."
    0
    Flag
  • 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. "
    0
    Flag
  • 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. "
    0
    Flag
  • 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."
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 166 Winding River Rd

  • What is 166 Winding River Rd estimated to be worth?
    Trulia's estimated value for 166 Winding River Rd in Wellesley, MA is $3,820,000.
  • What is the price history for 166 Winding River Rd?
    166 Winding River Rd in Wellesley, MA last sold for $2,785,000 in August 2020.
  • Is Wellesley a buyer's or seller's market?
    Wellesley is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Wellesley?
    The median sale price in Wellesley is $2.15M. That is up $161K from the prior month.
  • Does 166 Winding River Rd have air conditioning?
    Yes, 166 Winding River Rd in Wellesley, MA has air conditioning.
  • How big is the lot at 166 Winding River Rd?
    The lot at 166 Winding River Rd in Wellesley, MA is about 1.3 acres.

Explore by feature - Pet Friendly

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Off Market Homes Near 166 Winding River Rd

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