OFF MARKET

Off Market Aug 2020 for $2.7M

$4,280,606

Est. refi paymentEst. refi $12,914/mo

•

5,450

sq ft

166 Winding River Rd, Wellesley, MA 02482

About this home

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.

Single-familyProperty Type

1963Year Built

1.25 acresLot Size

$785Est. Price/Sq.Ft.

2 garage spacesParking

Listed by Betsy Kessler • Rutledge Properties

Bought with Betsy Kessler • Rutledge Properties

Redfin checked: 3 minutes ago

•Source:MLS PIN #72662519

Redfin Estimate

$4,280,606

$1.5M since sold in August 2020$56K since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 124.5% higher than the average sale price ($1.91M) of 6 comparable homes.

SOLD AUG 28, 2026
$2,250,000
A
4 beds3.5 baths5,496 sq ft
11 Haven St, Dover, MA 02030
SOLD AUG 21, 2026
$2,135,000
B
4 beds5.5 baths5,216 sq ft
7 Circle Dr, Dover, MA 02030
SOLD MAY 22, 2026
$1,280,000
C
4 beds2.5 baths2,560 sq ft
42 Troutbrook Rd, Dover, MA 02030
SOLD JUL 20, 2026
$1,279,900
D
4 beds3 baths2,300 sq ft
9 Riverbend Dr, Natick, MA 01760
SOLD JAN 16, 2026
$1,395,000
E
4 beds2.5 baths4,245 sq ft
12 Cranberry Ln, Dover, MA 02030
SOLD AUG 25, 2026
$3,100,000
F
6 beds4.5 baths4,475 sq ft
10 Colgate Rd, Wellesley, MA 02482

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Earn from this home

Sell

$2,105,459

Est. take-home

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Est. cash available

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Rent

$8,868/mo

Redfin rental estimate

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Market trends in 02482, MA

Last updated August 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

100.4%

0.6% MoM

Median sale price

$1.9M

$277K MoM

Avg. days on market

15d

3 days MoM

Recently sold homes

7 MoM

New listings for sale

NEW 1 HR AGO
$5,350,000
5 beds6.5 baths8,700 sq ft
55 Ridge Hill Farm Rd, Wellesley, MA 02482
NEW 19 HRS AGO
$1,375,000
4 beds2 baths1,570 sq ft
7 Dexter Rd, Wellesley, MA 02482
EARLY ACCESS
$1,299,000
2 beds2 baths1,688 sq ft
65 Grove St #5, Wellesley, MA 02482
See all

Provided by Redfin

Sale history for 166 Winding River Rd

Date

Event

Price

MLS PIN #72662519

Aug 17, 2020

Sold

$2,785,000

$511/sq ft

Jun 17, 2020

Price Changed

$2,785,000

$511/sq ft

May 27, 2020

Listed

$2,925,000

$537/sq ft

MLS PIN #30780242

Nov 8, 2004

Sold

$2,040,000

$374/sq ft

Aug 14, 2004

Listing Removed

—

Oct 15, 2003

Listed

$2,195,000

$403/sq ft

+11

Location, Location, Location!!! Enjoy the summer in your own back yard with the banks of the Charles River at your door step. Outstanding european manor home on 1+ acres. One of the prettiest living rooms with tray ceiling, gracious entertaiment size dining room, pannelled library, fireplaced family room adjacent to newer kit with granite Four spacious bedrooms including a first floor bedroom for guests, in laws or au pair. Private and serene wooded setting. A very special property!

Public Records

Jul 1, 1989

Sold

$892,500

$164/sq ft

Year

Property tax

Land + Additions

Assessment*

2023

$32,300 (+7.8%)

$1,578,000 + $1,243,000

$2,821,000

2022

$29,959 (−0.6%)

$1,414,000 + $1,151,000

$2,565,000

2021

$30,139 (+7.6%)

$1,414,000 + $1,151,000

$2,565,000

2020

$28,021

$1,414,000 + $1,010,000

$2,424,000

2019

$28,046 (+7.6%)

$1,414,000 + $1,010,000

$2,424,000

2018

$26,063 (+1.4%)

$1,100,000 + $1,081,000

$2,181,000

2017

$25,714 (+0.5%)

$1,100,000 + $1,081,000

$2,181,000

2015

$25,582 (+10.2%)

$1,081,000 + $1,132,000

$2,213,000

2014

$23,207 (−0.9%)

$895,000 + $1,116,000

$2,011,000

2013

$23,423 (+1.9%)

$839,000 + $1,163,000

$2,002,000

2012

$22,983 (−3.7%)

$839,000 + $1,163,000

$2,002,000

2011

$23,866 (+6.1%)

$832,000 + $1,256,000

$2,088,000

2010

$22,501 (+14.2%)

$891,000 + $1,256,000

$2,147,000

2009

$19,698

$978,000 + $1,102,000

$2,080,000

Tax history for 166 Winding River Rd

Year

Property tax

Land + Additions

Assessment*

2023

$32,300 (+7.8%)

$1,578,000 + $1,243,000

$2,821,000

2022

$29,959 (−0.6%)

$1,414,000 + $1,151,000

$2,565,000

2021

$30,139 (+7.6%)

$1,414,000 + $1,151,000

$2,565,000

2020

$28,021

$1,414,000 + $1,010,000

$2,424,000

2019

$28,046 (+7.6%)

$1,414,000 + $1,010,000

$2,424,000

2018

$26,063 (+1.4%)

$1,100,000 + $1,081,000

$2,181,000

2017

$25,714 (+0.5%)

$1,100,000 + $1,081,000

$2,181,000

2015

$25,582 (+10.2%)

$1,081,000 + $1,132,000

$2,213,000

2014

$23,207 (−0.9%)

$895,000 + $1,116,000

$2,011,000

2013

$23,423 (+1.9%)

$839,000 + $1,163,000

$2,002,000

2012

$22,983 (−3.7%)

$839,000 + $1,163,000

$2,002,000

2011

$23,866 (+6.1%)

$832,000 + $1,256,000

$2,088,000

2010

$22,501 (+14.2%)

$891,000 + $1,256,000

$2,147,000

2009

$19,698

$978,000 + $1,102,000

$2,080,000

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Beds

Baths

3.5

Stories

Lot width

—

Lot depth

—

Lot size

1.25 Acres

Year renovated

—

Sq. Ft.

5,450

Year built

1966

Style

Single Family Residential

County

Norfolk County

APN

262367

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 20, 2023.

Property details

Parking

Parking Information
Has Garage
Has Open Parking
# of Garage Spaces: 2
# of Covered Spaces: 2
Parking Spaces: 10
AttachedGarageYN: Yes
Parking Features: Attached, Under, Paved Drive, Off Street

Interior

Master Bedroom Information
Level: Second
Features: Bathroom - Full,Walk-In Closet(s),Closet,Closet/Cabinets - Custom Built,Flooring - Wall to Wall Carpet,Dressing Room,Recessed Lighting,Remodeled

Bedroom #2 Information
Level: First
Features: Bathroom - Full,Closet,Flooring - Hardwood

Bedroom #3 Information
Level: Second
Features: Fireplace,Closet,Flooring - Hardwood,Recessed Lighting

Bedroom #4 Information
Level: Second
Features: Walk-In Closet(s),Flooring - Hardwood,Balcony - Exterior,French Doors,Dressing Room,Exterior Access,Recessed Lighting

Bathroom Information
# of Bathrooms (Full): 3
# of Bathrooms (Half): 1
Master Bathroom Features: Yes

Bathroom #1 Information
Level: First
Features: Bathroom - Half,Flooring - Stone/Ceramic Tile,Countertops - Stone/Granite/Solid,Recessed Lighting,Remodeled,Lighting - Pendant

Bathroom #2 Information
Level: Second
Features: Bathroom - Full,Bathroom - Tiled With Shower Stall,Bathroom - With Tub,Skylight,Closet - Linen,Closet/Cabinets - Custom Built,Flooring - Stone/Ceramic Tile,Countertops - Stone/Granite/Solid,Double Vanity,Recessed Lighting,Remodeled

Bathroom #3 Information
Level: Second
Features: Bathroom - Full,Bathroom - Double Vanity/Sink,Bathroom - Tiled With Tub & Shower,Closet/Cabinets - Custom Built,Flooring - Stone/Ceramic Tile,Countertops - Stone/Granite/Solid,Recessed Lighting,Remodeled

Living Room Information
Level: First
Features: Flooring - Hardwood,French Doors,Exterior Access,Tray Ceiling(s)

Family Room Information
Level: First
Features: Flooring - Hardwood,Exterior Access,Open Floorplan,Recessed Lighting

Dining Room Information
Level: First
Features: Closet/Cabinets - Custom Built,Flooring - Hardwood,French Doors,Recessed Lighting,Remodeled

Kitchen Information
Level: First
Features: Closet/Cabinets - Custom Built,Flooring - Stone/Ceramic Tile,Dining Area,Pantry,Countertops - Stone/Granite/Solid,Kitchen Island,Cabinets - Upgraded,Exterior Access,Open Floorplan,Recessed Lighting,Remodeled,Stainless Steel Appliances,Wine Chiller

Basement Information
Basement: Full, Partially Finished, Garage Access

Fireplace Information
Has Fireplace
# of Fireplaces (Total): 3
Fireplace Features: Family Room, Living Room

Interior Features
# of Rooms (Total): 10
Door Features: French Doors
Window Features: Window(s) - Bay/Bow/Box
Flooring: Tile, Carpet, Hardwood, Flooring - Stone/Ceramic Tile, Flooring - Hardwood
Interior Features: Bathroom - Full, Bathroom - Double Vanity/Sink, Bathroom - Tiled With Shower Stall, Closet/Cabinets - Custom Built, Countertops - Stone/Granite/Solid, Recessed Lighting, Wainscoting, Lighting - Pendant, Bathroom, Library, Sun Room

Exterior

Building Information
Building Area (Total): 5,450
Foundation Details: Concrete Perimeter
Construction Materials: Frame
Year Built Source: Public Records
Year Built Details: Approximate

Exterior Features
Fencing: Fenced/Enclosed, Fenced
Roof: Shingle
Patio And Porch Features: Deck, Patio
Exterior Features: Deck, Patio, Professional Landscaping, Sprinkler System, Fenced Yard, Garden

Property Information
Accessibility Features: No
PropertySubType: Single Family Residence
Property Condition: Updated/Remodeled, Remodeled
Security Features: Security System
Has Waterview
River

Lot Information
Lot Size (Acres): 1.25
WaterfrontYN: Yes
Road Frontage Type: Public

Financial

Tax Information
Tax Annual Amount: $28,021
Tax Year: 2020

Utilities

Utility Information
Sewer: Public Sewer
Water Source: Public

Heating & Cooling
Has Heating
Has Cooling
Heating: Baseboard, Natural Gas
Cooling: Central Air

Location

Location Information
Directions: Dover Rd to Livingston to Winding River.
UnparsedAddress: 166 Winding River Rd, Wellesley MA 02482

Community Information
Senior CommunityYN: No
Community Features: Public Transportation, Shopping, Walk/Jog Trails, Stable(s), Golf, Medical Facility, Conservation Area, Highway Access, House of Worship, Private School, Public School, University

Public facts

Beds: 4
Baths: 3.5
Sq. Ft.: 5,450
Stories: 2.0
Lot Size: 1.25 acres
Style: Single Family Residential
Year Built: 1966
Year Renovated: —
County: Norfolk County
APN: 262367

Home facts updated by county records on Jul 20, 2023

Other

Miscellaneous Information
Heat Zones: 9

Listing Information
StandardStatus: Closed

Around this home

Schools

Hunnewell Elementary School

Public K-5 • Assigned • 1.5mi

9/10

Wellesley Middle School

Public 6-8 • Assigned • 2.1mi

8/10

Wellesley High School

Public 9-12 • Assigned • 2.1mi

10/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

5/10 Heat Factor

7 days above 98° expected this year, 15 days in 30 years

6/10 Wind Factor

52% chance of strong winds in next 30 years

2/10 Air Factor

1 unhealthy days expected this year, 2 days in 30 years

Provided by First Street

Historical weather

Wellesley, MA • 02482

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 9 hours in June and 4.4 hours in December, placing it below the U.S. average for solar exposure.

9 hrs

4.4 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$4.07M – $4.92M

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New listings for sale in 02482

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Home values near 166 Winding River Rd

Data from public records.

Address	Redfin Estimate
131 Winding River Rd, Needham, MA 4 Beds \| 4.5 Baths \| 2836 Sq. Ft.	$2,168,465
150 Winding River Rd, Needham, MA 5 Beds \| 4 Baths \| 3279 Sq. Ft.	$2,286,617

Address	Redfin Estimate
145 Winding River Rd, Needham, MA 5 Beds \| 5.5 Baths \| 6346 Sq. Ft.	$3,776,340
130 Winding River Rd, Needham, MA 4 Beds \| 2.5 Baths \| 3026 Sq. Ft.	$2,278,332

Address	Redfin Estimate
161 Winding River Rd, Needham, MA 4 Beds \| 3.5 Baths \| 3000 Sq. Ft.	$2,598,663
100 Winding River Rd, Needham, MA 5 Beds \| 4.5 Baths \| 5083 Sq. Ft.	$2,614,009

Property information provided by MLS PIN when last listed in 2020. This data may not match . Learn more.

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GreatSchools Ratings provided by GreatSchools.org.

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About this home

Redfin Estimate

Earn from this home

Market trends in 02482, MA

Sale history for 166 Winding River Rd

Tax history for 166 Winding River Rd

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 02482

Home values near 166 Winding River Rd

More real estate resources