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

44 Windemere Rd Wellesley — Photo 1 of 39

$1,500,000

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.

Market Value Analysis

This Property
Size (SqFt) →Price →
This Property$613/sqft
Local Avg (Wellesley)$690/sqft
11% BelowMarket Average

* Analysis is based on 21 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 RoomMaster 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

Master 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

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

1,189 housing units permitted in the last 12 months (+21% vs the prior 12 months) — 706 in 5+ unit buildings

U.S. Census Bureau, Building Permits Survey (through Jun '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

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