44 Windemere Rd Wellesley — Photo 1 of 39
Recent Drop: $50,000
$1,450,000
Investment Analysis — 44 Windemere Rd
Wellesley, MA 02481
Based on HUD Small Area Fair Market Rent for Boston-Cambridge-Quincy, MA-NH HUD Metro FMR Area, a 3-bedroom in 02481 carries an estimated $4,830/mo in gross rent — about a 2.11% cap rate and $30,606/yr in estimated NOI at the $1,450,000 list price. Adjust every assumption in the calculator below.
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.
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.
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.
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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
Master 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
Listing Agent: Aranson Maguire Group
Listing Office: Compass
MLS® Number: 73547678
