Active
86 Days on market
44 Windemere Rd Wellesley — Photo 1 of 39

44 Windemere Rd Wellesley — Photo 1 of 39

Recent Drop: $50,000

$1,500,000
$1,450,000

$1,450,000

44 Windemere Rd, Wellesley, MA 02481

Wellesley, MA 02481

Beds

3

Baths

3

SqFt

2,447

Style

Single Family

Built

1958

Set on a quiet residential cul-de-sac, this thoughtfully renovated 3-bedroom, 3-bath home offers a host of upgrades designed for effortless everyday living. The kitchen flows naturally into the sun-drenched dining room, where windows on three sides and one of three wood-burning fireplaces add warmth and character to the space. Together they look out over an expansive backyard, where a paver patio and mature landscaping create a private outdoor retreat perfect for entertaining or simply unwinding after a long day. Downstairs, the finished lower level adds tremendous flexibility with a secondary living room, a private office, a full bathroom, ample storage, and direct access to the garage. Close to Wellesley's town center, middle school, and high school, this is a home that truly has it all.

Key facts

It was listed on July 9, 2026. The price has come down from an original $1,500,000 to $1,450,000, most recently on September 10, 2026. The annual property taxes are $13,444 (2026 tax year). It sits on a 0.49-acre (21,220 sq ft) lot.

Open Houses

Market Value Analysis

This Property
Size (SqFt) →Price →
This Property$593/sqft
Local Avg (Wellesley)$676/sqft
12% BelowMarket Average

* Analysis is based on 24 actively listed and recently sold comparable properties strictly within Wellesley, MA.

Property Details

Financials

Original Price$1,500,000
Annual Taxes$13,444

Parking

Garage2
Off-Street6

Interior Specifications

Total Rooms13
Fireplaces3
FlooringTile, Hardwood
BasementFull, Finished, Walk-Out Access, Interior Entry, Garage Access

Climate & Utilities

HeatingCentral, Forced Air, Natural Gas
CoolingCentral Air
WaterPublic
SewerPublic Sewer

Building & Exterior

ConstructionFrame
Roof--
FoundationConcrete Perimeter
ZoningSR10

Property & Lot

Acres0.49
SqFt Lot21,220
Lot FeaturesCul-De-Sac, Wooded

Amenities & Appliances

Range • Dishwasher • Disposal • Refrigerator • Freezer • Washer • Dryer • Range Hood

Neighborhood

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

Geography

Floorplan Breakdown

Structural Layout

First
Living RoomDining RoomPrimary BedroomBedroom 2Bedroom 3Bathroom 1Bathroom 2
Basement
OfficeFamily RoomBathroom 3
Main,First
Kitchen
Living Room
Lvl First

Flooring - Wood

Dining Room
Lvl First

Wood / Coal / Pellet Stove

Kitchen
Lvl Main,First

Flooring - Wood, Window(s) - Picture, Countertops - Stone/Granite/Solid, Kitchen Island, Breakfast Bar / Nook, Remodeled, Stainless Steel Appliances, Gas Stove

Office
Lvl Basement

Closet/Cabinets - Custom Built, Walk-in Storage

Family Room
Lvl Basement

Flooring - Wood

Primary Bedroom
Lvl First

Bathroom - Full, Flooring - Wood

Bedroom 2
Lvl First
Bedroom 3
Lvl First

Flooring - Wood

Bathroom 1
Lvl First

Bathroom - Full, Bathroom - Double Vanity/Sink, Bathroom - Tiled With Tub & Shower

Bathroom 2
Lvl First

Bathroom - Full, Bathroom - Tiled With Shower Stall

Bathroom 3
Lvl Basement

Bathroom - Full, Bathroom - Tiled With Shower Stall

Property History

Price Drop
$1,450,000

Was $1,500,000

Sep 10, 2026

MLS® 73547678

Listed
$1,500,000

Jul 9, 2026

MLS® 73547678

Questions about this home

When was 44 Windemere Rd, Wellesley listed?

44 Windemere Rd, Wellesley was listed on July 9, 2026.

Has the price of 44 Windemere Rd, Wellesley changed?

The price has come down from an original $1,500,000 to $1,450,000, most recently on September 10, 2026.

What are the property taxes for 44 Windemere Rd, Wellesley?

The annual property taxes for 44 Windemere Rd, Wellesley are $13,444 (2026 tax year).

How big is the lot at 44 Windemere Rd, Wellesley?

44 Windemere Rd, Wellesley sits on a 0.49-acre (21,220 sq ft) lot.

What is the status of 44 Windemere Rd, Wellesley?

44 Windemere Rd, Wellesley is actively listed for sale.

Population

17,415

U.S. Census Bureau, ACS 2024 5-Year Estimates (B01003)

Median Household Income

$250K

U.S. Census Bureau, ACS 2024 5-Year Estimates (B19013)

Renter-Occupied Homes

12.7%

U.S. Census Bureau, ACS 2024 5-Year Estimates (B25003)

New Construction Permits — Norfolk County

1,524 housing units permitted in the last 12 months (+52% vs the prior 12 months) — 1,030 in 5+ unit buildings

U.S. Census Bureau, Building Permits Survey (through Jul '26)

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 2,447 sq ft principal dwelling). Lot size: 21,220 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.

Listing Provided By

Listing Agent: Aranson Maguire Group

Listing Office: Compass

MLS® Number: 73547678