Active
46 Days on market
12 Winding River Cir Wellesley — Photo 1 of 39

12 Winding River Cir Wellesley — Photo 1 of 39

$4,999,000

Investment Analysis — 12 Winding River Cir

Wellesley, MA 02482 — Dana Hall

Based on HUD Small Area Fair Market Rent for Boston-Cambridge-Quincy, MA-NH HUD Metro FMR Area, a 6-bedroom in 02482 carries an estimated $5,270/mo in gross rent — about a -0.09% cap rate and $-4,446/yr in estimated NOI at the $4,999,000 list price. Adjust every assumption in the calculator below.

View Standard Listing

Beds

6

Baths

7

SqFt

8,729

Style

Single Family

Built

2004

Nature Lovers Paradise on the Charles River! Stunning in every season, each element of this spectacular property is crafted to maximize your enjoyment and access to the great outdoors. Reimagined by renowned architect Patrick Ahern, the exterior boasts a flat grassy backyard and stone patios with unobstructed views. Inside, a gracious and flexible floor plan is filled with light and views from myriad windows, French doors, and private balconies. First floor living with exquisite primary bedroom suite, 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 suite option. Large walk-out finished LL w/ bar, gym & media room. 3 car garage and flat courtyard driveway off protected cul de sac within minutes of extensive Wellesley Trails and Town Center. A notch above the rest. Bring your hiking shoes, kayaks, lounge chairs and lawn games!

ADU Potential

Massachusetts allows one accessory dwelling unit by right in single-family zoning districts statewide (M.G.L. c. 40A §3; 760 CMR 71.00, effective Feb 2025). Estimated maximum ADU size for this property: 900 sq ft (the lesser of 900 sq ft or half the 8,729 sq ft principal dwelling). Lot size: 125,888 sq ft.

Based on listing data, which indicates the property type — not the zoning district. Local dimensional, septic (Title 5), and historic-district requirements still apply. Not legal advice — verify with the municipality.

Estimates — not financial advice

These figures are illustrative estimates for informational purposes only — not an appraisal, valuation, or guarantee of rent, income, or returns, and not financial, tax, or investment advice. Rent is either the figure reported on the MLS listing — in-place rent that may differ from market and is not verified against the actual leases — or, where the listing reports none, an estimate from HUD Small Area Fair Market Rents, a government benchmark that may differ from actual market rent. Each figure is labelled with its source. Cap rate, NOI, and returns depend on the assumptions shown, which you can change. MLS and other third-party data may be inaccurate or out of date. Verify all figures independently and consult your own financial, tax, and legal advisors before making any investment decision.

Property Details

Financials

Original Price$4,999,000
Annual Taxes$52,507.71

Parking

Garage3
Off-Street9

Interior Specifications

Total Rooms13
Fireplaces5
FlooringCarpet, Hardwood, Flooring - Hardwood, Flooring - Wood
BasementFull, Partially Finished, Walk-Out Access

Climate & Utilities

HeatingForced Air, Natural Gas
CoolingCentral Air
WaterPublic
SewerPublic Sewer

Building & Exterior

ConstructionFrame
RoofWood
FoundationConcrete Perimeter
ZoningSR40

Property & Lot

Acres2.89
SqFt Lot125,888
Lot FeaturesCul-De-Sac, Level

Amenities & Appliances

Gas Water Heater • Plumbed For Ice Maker

Neighborhood

Public Transportation • Shopping • Park • Walk/Jog Trails • Stable(s) • Golf

Geography

Floorplan Breakdown

Structural Layout

Second
Bedroom 2Bedroom 3Bedroom 4
First
Living RoomDining RoomKitchenOfficeFamily RoomBedroom 5Bathroom 1Bathroom 2Bathroom 3
Main,First
Master Bedroom
Living Room
Lvl First

27 x 17

Flooring - Hardwood, Deck - Exterior, Exterior Access

Dining Room
Lvl First

16 x 17

Flooring - Hardwood, Window(s) - Bay/Bow/Box

Kitchen
Lvl First

16 x 30

Beamed Ceilings, Flooring - Hardwood, Window(s) - Picture, Countertops - Stone/Granite/Solid, Kitchen Island, Wet Bar, Breakfast Bar / Nook, Cabinets - Upgraded

Office
Lvl First
Family Room
Lvl First

20 x 20

Flooring - Hardwood, French Doors, Wet Bar, Exterior Access

Master Bedroom
Lvl Main,First

23 x 21

Bathroom - Full, Vaulted Ceiling(s), Walk-In Closet(s), Flooring - Hardwood, French Doors, Double Vanity, Exterior Access

Bedroom 2
Lvl Second

18 x 19

Bedroom 3
Lvl Second

19 x 16

Bathroom - Full, Closet, Flooring - Hardwood, Balcony - Exterior, French Doors

Bedroom 4
Lvl Second

15 x 18

Bathroom - Full, Closet, Flooring - Wall to Wall Carpet, Balcony / Deck

Bedroom 5
Lvl First

19 x 11

Bathroom - Full, Closet, Flooring - Hardwood

Bathroom 1
Lvl First
Bathroom 2
Lvl First
Bathroom 3
Lvl First

Property History

Listed
$4,999,000

Jul 28, 2026

MLS® 73555707

Terminated
$4,999,000

Jul 27, 2026

MLS® 73485582

Listed
$4,999,000

Mar 11, 2026

MLS® 73485582

Listing Provided By

Listing Agent: Christine Lawrence

Listing Office: Rutledge Properties

MLS® Number: 73555707

Related Insights

Massachusetts $1M Sale Trigger for 2026 Investors
Real Estate
Aug 27, 2026

Massachusetts $1M Sale Trigger for 2026 Investors

View All Insights