
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.
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
* Analysis is based on 24 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
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 Agent: Aranson Maguire Group
Listing Office: Compass
MLS® Number: 73547678









