
44 Windemere Rd Wellesley — Photo 1 of 39
Recent Drop: $50,000
$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.
Market Value Analysis
* Analysis is based on 22 actively listed and recently sold comparable properties strictly within Wellesley, MA.
Property Details
Financials
Parking
Interior Specifications
Climate & Utilities
Building & Exterior
Property & Lot
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
Living Room
Lvl FirstFlooring - Wood
Dining Room
Lvl FirstWood / Coal / Pellet Stove
Kitchen
Lvl Main,FirstFlooring - Wood, Window(s) - Picture, Countertops - Stone/Granite/Solid, Kitchen Island, Breakfast Bar / Nook, Remodeled, Stainless Steel Appliances, Gas Stove
Office
Lvl BasementCloset/Cabinets - Custom Built, Walk-in Storage
Family Room
Lvl BasementFlooring - Wood
Primary Bedroom
Lvl FirstBathroom - Full, Flooring - Wood
Bedroom 2
Lvl FirstBedroom 3
Lvl FirstFlooring - Wood
Bathroom 1
Lvl FirstBathroom - Full, Bathroom - Double Vanity/Sink, Bathroom - Tiled With Tub & Shower
Bathroom 2
Lvl FirstBathroom - Full, Bathroom - Tiled With Shower Stall
Bathroom 3
Lvl BasementBathroom - Full, Bathroom - Tiled With Shower Stall
Property History
$1,450,000
Was $1,500,000
Sep 10, 2026
MLS® 73547678
$1,500,000
Jul 9, 2026
MLS® 73547678
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 Agent: Aranson Maguire Group
Listing Office: Compass
MLS® Number: 73547678
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