Single Family Residence at 12 Winding River Cir, Wellesley MA 02482
Single Family Residence at 12 Winding River Cir, Wellesley MA 02482, photo 2 of 39
Single Family Residence at 12 Winding River Cir, Wellesley MA 02482, photo 3 of 39
Single Family Residence at 12 Winding River Cir, Wellesley MA 02482, photo 4 of 39
Single Family Residence at 12 Winding River Cir, Wellesley MA 02482, photo 5 of 39
Single Family Residence at 12 Winding River Cir, Wellesley MA 02482, photo 6 of 39
Single Family Residence at 12 Winding River Cir, Wellesley MA 02482, photo 7 of 39
Single Family Residence at 12 Winding River Cir, Wellesley MA 02482, photo 8 of 39
Single Family Residence at 12 Winding River Cir, Wellesley MA 02482, photo 9 of 39
Single Family Residence at 12 Winding River Cir, Wellesley MA 02482, photo 10 of 39
Single Family Residence at 12 Winding River Cir, Wellesley MA 02482, photo 11 of 39
Single Family Residence at 12 Winding River Cir, Wellesley MA 02482, photo 12 of 39
Single Family Residence at 12 Winding River Cir, Wellesley MA 02482, photo 13 of 39
Single Family Residence at 12 Winding River Cir, Wellesley MA 02482, photo 14 of 39
Single Family Residence at 12 Winding River Cir, Wellesley MA 02482, photo 15 of 39
Single Family Residence at 12 Winding River Cir, Wellesley MA 02482, photo 16 of 39
Single Family Residence at 12 Winding River Cir, Wellesley MA 02482, photo 17 of 39
Single Family Residence at 12 Winding River Cir, Wellesley MA 02482, photo 18 of 39
Single Family Residence at 12 Winding River Cir, Wellesley MA 02482, photo 19 of 39
Single Family Residence at 12 Winding River Cir, Wellesley MA 02482, photo 20 of 39
Single Family Residence at 12 Winding River Cir, Wellesley MA 02482, photo 21 of 39
Single Family Residence at 12 Winding River Cir, Wellesley MA 02482, photo 22 of 39
Single Family Residence at 12 Winding River Cir, Wellesley MA 02482, photo 23 of 39
Single Family Residence at 12 Winding River Cir, Wellesley MA 02482, photo 24 of 39
Single Family Residence at 12 Winding River Cir, Wellesley MA 02482, photo 25 of 39
Single Family Residence at 12 Winding River Cir, Wellesley MA 02482, photo 26 of 39
Single Family Residence at 12 Winding River Cir, Wellesley MA 02482, photo 27 of 39
Single Family Residence at 12 Winding River Cir, Wellesley MA 02482, photo 28 of 39
Single Family Residence at 12 Winding River Cir, Wellesley MA 02482, photo 29 of 39
Single Family Residence at 12 Winding River Cir, Wellesley MA 02482, photo 30 of 39
Single Family Residence at 12 Winding River Cir, Wellesley MA 02482, photo 31 of 39
Single Family Residence at 12 Winding River Cir, Wellesley MA 02482, photo 32 of 39
Single Family Residence at 12 Winding River Cir, Wellesley MA 02482, photo 33 of 39
Single Family Residence at 12 Winding River Cir, Wellesley MA 02482, photo 34 of 39
Single Family Residence at 12 Winding River Cir, Wellesley MA 02482, photo 35 of 39
Single Family Residence at 12 Winding River Cir, Wellesley MA 02482, photo 36 of 39
Single Family Residence at 12 Winding River Cir, Wellesley MA 02482, photo 37 of 39
Single Family Residence at 12 Winding River Cir, Wellesley MA 02482, photo 38 of 39
Single Family Residence at 12 Winding River Cir, Wellesley MA 02482, photo 39 of 39
39 photos

$4,999,000

12 Winding River Cir, Wellesley MA 02482
Wellesley, MA 02482
Listed by Betsy Kessler
Bedrooms
6
Bathrooms
7
Living area
9,036 sqft
Year built
2004

About this home

Exceptional property on the Charles River! 2.89 acres of manicured lawn rolls down to the river giving you unobstructed views & private use of a nature lover's paradise. Gorgeous stone patios, multiple decks, & sun-filled rooms w/French Doors are all designed to maximize your enjoyment of this incredible retreat. Privately nestled on a quiet cul-de-sac, this stunning Cape is beautiful in all seasons and offers a gracious and flexible floor plan including an exquisite first-floor primary bedroom suite w/ river view. A great room, expansive living room, dining and updated kitchen w/ light-filled breakfast room, an add’l bedroom suite and choice of offices complete the main floor. Upstairs, 4 more ensuite bedrooms, including a 2nd primary w/ a heavenly office. Large walk-out finished LL w/ bar, gym and media room and 3 car garage. Extensively rebuilt in 2004 renowned architect Patrick Ahearn, the design, quality and setting are a knotch above the rest. Bring your kayaks and lounge chairs!

Highlights

WaterfrontViewFireplace

Property details

MLS
MLS Property Information Network
MLS #
73485582
Property type
Single Family Residence
Subdivision
Dana Hall
Status
Active
Days on market
224
On market date
March 11, 2026
Stories
N/A
Total bathrooms
7
Garage spaces
3
Parking spaces
9
Lot size
2.89 acres
Loading map…

Nearby schools

Within 10 miles. School directory data from the National Center for Education Statistics (NCES), accessed via the Urban Institute Education Data API. Local Score is calculated by INNOVATE Real Estate; where a state rating is shown, it comes from that state's own official school report card.

Elementary
Memorial
1.34 mi away · Grades 0-4
Nearest school -- attendance-zone data not available here
4.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
396
Student:teacher ratio
14.1:1
District
Natick
Middle
Wellesley Middle
1.98 mi away · Grades 6-8
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
1,008
Student:teacher ratio
9.4:1
District
Wellesley
High
Wellesley Sr High
2.04 mi away · Grades 9-12
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
1,406
Student:teacher ratio
11.9:1
District
Wellesley

Walkability

Blended score for Wellesley's center, calculated by INNOVATE Real Estate from two sources: the EPA's National Walkability Index (street network, transit, land-use mix) and Google Places amenity data (what's actually reachable on foot from this point). 60% EPA National Walkability Index + 40% nearby-amenity density (Google Places).

62
Walkable
out of 100
EPA National Walkability Index
11.8 / 20 -- Above average walkable
Google Places amenity density
67 / 100
Restaurants & cafes20
Grocery stores0
Parks9
Schools13
Transit stops2
Pharmacies0

Market position

How this listing compares to current activity in Wellesley, from live MLS data.

On the market 224 days -- 109 more days than Wellesley's current average of 115 days.
For reference, the median list price across 183 active listings in Wellesley right now is $1,747,200.

Mortgage calculator

Estimate only - actual rate and payment depend on your lender, credit, and loan program.

$
%
%
Adjust tax / insurance estimates
% / yr
$
/mo
Est. monthly payment
$30,255/mo
$999,800 down
$3,999,200 loan
Principal & interest$25,939
Property tax (est.)$4,166
Home insurance (est.)$150

Similar homes you might like

Data source: Listing information provided by MLS Property Information Network via Trestle/CoreLogic. Last updated June 25, 2026.

Information herein deemed reliable but not guaranteed; all measurements, school assignments, HOA fees, taxes, and feature lists are approximate and should be independently verified. Equal Housing Opportunity.