OFF MARKET

Off Market May 2014 for $3.7M

$5,888,599

Est. refi paymentEst. refi $1,159/mo

•

8,600

sq ft

165 Winding River Rd, Wellesley, MA 02482

About this home

Located in one of Wellesley's most desirable neighborhoods, this breathtaking colonial is situated on a private acre abutting conservation land. State of the art chef's kitchen with breakfast room & butler's pantry opens to a spacious family room. Fireplaced master BR with marble bath, private balcony & his/hers walk-in closets. This elegant home features custom cabinets/built-ins & high-end details throughout. LL includes media, exercise and game room with custom bar. Relaxing covered patio

Single-familyProperty Type

2013Year Built

1.02 acresLot Size

$685Est. Price/Sq.Ft.

3 garage spacesParking

Listed by Jennifer and Hillary • Berkshire Hathaway HomeServices Town and Country Real Estate

Bought with Debi Benoit • Benoit Mizner Simon & Co. - Wellesley - Central St

Redfin checked: 3 minutes ago

•Source:MLS PIN #71538197

Redfin Estimate

$5,888,599

$2.2M since sold in May 2014$313K since July

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 11.8% higher than the average sale price ($5.27M) of 6 comparable homes.

SOLD JUL 27, 2026
$5,100,000
A
6 beds6.5 baths7,322 sq ft
1 Buckingham Ter, Wellesley, MA 02482
SOLD AUG 25, 2026
$3,725,000
B
6 beds6.5 baths8,182 sq ft
365 Charles River St, Needham, MA 02492
SOLD JAN 9, 2026
$5,489,000
C
7 beds7 baths8,257 sq ft
78 Pheasant Landing Rd, Needham, MA 02492
SOLD MAY 28, 2026
$6,660,000
D
6 beds8.5 baths10,090 sq ft
121 Livingston Rd, Wellesley, MA 02482
SOLD AUG 13, 2026
$5,696,375
E
6 beds6 baths7,040 sq ft
25 Kenilworth Rd, Wellesley, MA 02482
SOLD MAY 5, 2026
$4,925,000
F
7 beds7.5 baths10,047 sq ft
34 Stratford Rd, Needham, MA 02492

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Earn from this home

Sell

$3,454,760

Est. take-home

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Refinance

Est. cash available

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Rent

$9,291/mo

Redfin rental estimate

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Market trends in 02482, MA

Last updated July 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

101.0%

+0.0% MoM

Median sale price

$1.6M

$119K MoM

Avg. days on market

18d

3 days MoM

Recently sold homes

18 MoM

New listings for sale

$1,295,000
2 beds2.5 baths1,648 sq ft
5 Oakdale Ave, Wellesley, MA 02482
$1,675,000
4 beds4 baths2,086 sq ft
29 Cottage St, Wellesley, MA 02482
See all

Provided by Redfin

Sale history for 165 Winding River Rd

Date

Event

Price

MLS PIN #71538197

May 8, 2014

Sold

$3,700,000

$430/sq ft

Nov 6, 2013

Contingent

—

Jun 7, 2013

Listed

$3,850,000

$448/sq ft

MLS PIN #71375106

Aug 2, 2012

Sold

$1,215,000

$141/sq ft

May 24, 2012

Contingent

—

Apr 30, 2012

Listed

$1,595,000

$185/sq ft

Public Records

Jun 1, 1981

Sold

$185,000

$22/sq ft

Year

Property tax

Land + Additions

Assessment*

2023

$42,617 (+1.3%)

$1,423,000 + $2,299,000

$3,722,000

2022

$42,083 (−0.6%)

$1,275,000 + $2,328,000

$3,603,000

2021

$42,335 (+1.6%)

$1,275,000 + $2,328,000

$3,603,000

2020

$41,651

$1,275,000 + $2,328,000

$3,603,000

2019

$41,687 (+0.1%)

$1,275,000 + $2,328,000

$3,603,000

2018

$41,634 (+1.3%)

$1,079,000 + $2,405,000

$3,484,000

2017

$41,088 (−4.3%)

$1,079,000 + $2,406,000

$3,485,000

2016

$42,919 (+2.5%)

$1,061,000 + $2,567,000

$3,628,000

2015

$41,870 (+50.1%)

$1,061,000 + $2,561,000

$3,622,000

2014

$27,892 (+69.9%)

$878,000 + $1,539,000

$2,417,000

2013

$16,415 (+1.9%)

$823,000 + $580,000

$1,403,000

2012

$16,106 (−0.5%)

$823,000 + $580,000

$1,403,000

2011

$16,185 (+4.8%)

$817,000 + $599,000

$1,416,000

2010

$15,448 (+10.7%)

$875,000 + $599,000

$1,474,000

2009

$13,949

$961,000 + $512,000

$1,473,000

Tax history for 165 Winding River Rd

Year

Property tax

Land + Additions

Assessment*

2023

$42,617 (+1.3%)

$1,423,000 + $2,299,000

$3,722,000

2022

$42,083 (−0.6%)

$1,275,000 + $2,328,000

$3,603,000

2021

$42,335 (+1.6%)

$1,275,000 + $2,328,000

$3,603,000

2020

$41,651

$1,275,000 + $2,328,000

$3,603,000

2019

$41,687 (+0.1%)

$1,275,000 + $2,328,000

$3,603,000

2018

$41,634 (+1.3%)

$1,079,000 + $2,405,000

$3,484,000

2017

$41,088 (−4.3%)

$1,079,000 + $2,406,000

$3,485,000

2016

$42,919 (+2.5%)

$1,061,000 + $2,567,000

$3,628,000

2015

$41,870 (+50.1%)

$1,061,000 + $2,561,000

$3,622,000

2014

$27,892 (+69.9%)

$878,000 + $1,539,000

$2,417,000

2013

$16,415 (+1.9%)

$823,000 + $580,000

$1,403,000

2012

$16,106 (−0.5%)

$823,000 + $580,000

$1,403,000

2011

$16,185 (+4.8%)

$817,000 + $599,000

$1,416,000

2010

$15,448 (+10.7%)

$875,000 + $599,000

$1,474,000

2009

$13,949

$961,000 + $512,000

$1,473,000

*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

Stories

Lot width

—

Lot depth

—

Lot size

1.02 Acres

Year renovated

—

Sq. Ft.

6,837

Year built

2013

Style

Single Family Residential

County

Norfolk County

APN

262364

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: 3
# of Covered Spaces: 3
Parking Spaces: 6
AttachedGarageYN: Yes
Parking Features: Attached, Garage Door Opener, Heated Garage, Insulated, Paved Drive, Off Street, Paved

Interior

Master Bedroom Information
Area: 440
Length: 22
Width: 20
Level: Second
Features: Bathroom - Full,Coffered Ceiling(s),Walk-In Closet(s),Flooring - Hardwood,Recessed Lighting

Bedroom #2 Information
Area: 224
Length: 14
Width: 16
Level: Second
Features: Bathroom - Full,Flooring - Hardwood,Recessed Lighting

Bedroom #3 Information
Area: 240
Length: 16
Width: 15
Level: Second
Features: Bathroom - Full,Flooring - Hardwood,Recessed Lighting

Bedroom #4 Information
Area: 168
Length: 12
Width: 14
Level: Second
Features: Bathroom - Half,Flooring - Hardwood,Recessed Lighting

Bedroom #5 Information
Area: 255
Length: 15
Width: 17
Level: Second
Features: Bathroom - Full,Flooring - Hardwood,Recessed Lighting

Bathroom Information
# of Bathrooms (Full): 7
# of Bathrooms (Half): 2
Master Bathroom Features: Yes

Bathroom #1 Information
Level: Second
Features: Bathroom - Full,Bathroom - Double Vanity/Sink,Flooring - Stone/Ceramic Tile,Countertops - Stone/Granite/Solid,Jacuzzi / Whirlpool Soaking Tub,Recessed Lighting,Steam / Sauna

Bathroom #2 Information
Level: Second
Features: Bathroom - Full,Bathroom - Tiled With Tub & Shower,Flooring - Stone/Ceramic Tile,Countertops - Stone/Granite/Solid

Bathroom #3 Information
Level: Second
Features: Bathroom - Full,Bathroom - Tiled With Tub & Shower,Flooring - Stone/Ceramic Tile,Countertops - Stone/Granite/Solid,Recessed Lighting

Living Room Information
Area: 330
Length: 22
Width: 15
Level: First
Features: Coffered Ceiling(s),Flooring - Hardwood,Recessed Lighting

Family Room Information
Area: 418
Length: 22
Width: 19
Level: First
Features: Closet/Cabinets - Custom Built,Flooring - Hardwood,French Doors,Recessed Lighting

Dining Room Information
Area: 288
Length: 16
Width: 18
Level: First
Features: Flooring - Hardwood,Recessed Lighting

Kitchen Information
Area: 425
Length: 25
Width: 17
Level: First
Features: Closet/Cabinets - Custom Built,Flooring - Hardwood,Countertops - Stone/Granite/Solid,Kitchen Island,Wet Bar,Recessed Lighting,Pot Filler Faucet,Wine Chiller

Basement Information
Basement: Full, Finished, Garage Access, Sump Pump, Concrete

Laundry Information
Laundry Features: Countertops - Stone/Granite/Solid, Dryer Hookup - Dual, Gas Dryer Hookup, Electric Dryer Hookup, Washer Hookup

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

Interior Features
# of Rooms (Total): 17
Door Features: Insulated Doors, French Doors
Window Features: Insulated Windows
Flooring: Wood, Carpet, Marble, Hardwood, Stone / Slate, Flooring - Wall to Wall Carpet, Flooring - Hardwood
Interior Features: Bathroom - Full, Coffered Ceiling(s), Closet/Cabinets - Custom Built, Recessed Lighting, Bedroom, Bonus Room, Library, Media Room, Exercise Room, Game Room, Central Vacuum, Sauna/Steam/Hot Tub, Wet Bar, Finish - Cement Plaster

Exterior

Building Information
Building Area (Total): 8,600
Foundation Details: Concrete Perimeter
Construction Materials: Frame, Stone
Year Built Source: Builder
Year Built Details: Under Construction
Lead Paint: None

Exterior Features
Roof: Shingle
Patio And Porch Features: Deck - Exterior, Screened, Deck - Wood, Patio, Covered
Exterior Features: Porch - Screened, Deck - Wood, Patio, Covered Patio/Deck, Rain Gutters, Professional Landscaping, Sprinkler System, Stone Wall

Property Information
PropertySubType: Single Family Residence
Security Features: Security System

Lot Information
Lot Size (Acres): 1.02
Frontage Length: 200
Road Surface Type: Paved
Road Frontage Type: Public

Financial

Tax Information
Tax Annual Amount: $16,415
Tax Year: 2013

Utilities

Utility Information
Utilities: for Gas Range, for Electric Oven, for Gas Dryer, for Electric Dryer, Washer Hookup, Icemaker Connection
Sewer: Public Sewer
Water Source: Public
Electric: Generator, 220 Volts, Circuit Breakers, Other (See Remarks)

Heating & Cooling
Has Heating
Has Cooling
Heating: Natural Gas, Hydro Air, Hydronic Floor Heat(Radiant)
Cooling: Central Air

Location

Location Information
Directions: Dover Rd to Livingston Rd to Winding River Rd
UnparsedAddress: 165 Winding River Rd, Wellesley MA 02482

Community Information
Senior CommunityYN: No
Community Features: Walk/Jog Trails, Conservation Area

Public facts

Beds: 5
Baths: 8.0
Sq. Ft.: 6,837
Stories: 3.0
Lot Size: 1.02 acres
Style: Single Family Residential
Year Built: 2013
Year Renovated: —
County: Norfolk County
APN: 262364

Home facts updated by county records on Jul 20, 2023

Other

Miscellaneous Information
Heat Zones: 8

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

53% 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

$5.60M – $6.77M

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Home values near 165 Winding River Rd

Data from public records.

Address	Redfin Estimate
131 Winding River Rd, Needham, MA 4 Beds \| 4.5 Baths \| 2836 Sq. Ft.	$2,126,229
150 Winding River Rd, Needham, MA 5 Beds \| 4 Baths \| 3279 Sq. Ft.	$2,390,006

Address	Redfin Estimate
145 Winding River Rd, Needham, MA 5 Beds \| 5.5 Baths \| 6346 Sq. Ft.	$3,967,520
130 Winding River Rd, Needham, MA 4 Beds \| 2.5 Baths \| 3026 Sq. Ft.	$2,443,462

Address	Redfin Estimate
161 Winding River Rd, Needham, MA 4 Beds \| 3.5 Baths \| 3000 Sq. Ft.	$2,697,361
100 Winding River Rd, Needham, MA 5 Beds \| 4.5 Baths \| 5083 Sq. Ft.	$2,598,526

Property information provided by MLS PIN when last listed in 2013. 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 165 Winding River Rd

Tax history for 165 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 165 Winding River Rd

More real estate resources