44 Windemere Rd

2,447 Sq. Ft.
$613 / Sq. Ft.
2,447
Sq. Ft.
$613
per Sq. Ft.

Description

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...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.

Property Details for 44 Windemere Road

Town
Wellesley
Area
MA-Wellesley
Architectural Style
Ranch, Raised Ranch
Style
Ranch, Raised Ranch
Garage Spaces
2
Open Parking Spaces
4.00
Parking Spaces Total
6
LISTING UPDATED: 07/13/2026 03:09 AM

Property Details for 44 Windemere Road

StatusActive
MLS #73547678
Days on Market5
Taxes$13,444 / year
HOA Fees-
Property TypeSingle Family
MLS TypeSingle Family / Detached
Year Built1958
CountyNorfolk County

Location

Listing Courtesy of: .

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Building Information for 44 Windemere Road

Stories-Year Built1958Building Size-Lot Size0.49 AC / 21,220 SF

Payment Calculator

$8,595 per month

30 year fixed, 6.36% Interest

Principal and Interest

$7,475

Property Taxes

$1,120

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 44 Windemere Road

General Details
Property Details
  • Building Area Units: Square Feet
  • Community Features: Public Transportation, Shopping, Tennis Court, Park, Walk/Jog Trails, Golf Course, Medical Facility, Bike Path, Conservation Area, Highway Access, House of Worship, Private School, Public School, T-Station, University
  • Living Area: 2447.0
  • Color: White
  • SqFt with Basement: Yes
  • Property Attached: No
  • Single Family Type: Detached
  • Waterfront: No
  • Year Built Details: Actual
  • Year Built Source: Public Records
Location/School
  • Grade School: Sprague Elementary
  • High School: Wellesley High School
  • Middle School: Wellesley Middle School
Features
Interior Features
  • Appliances: Range, Dishwasher, Disposal, Refrigerator, Freezer, Washer, Dryer, Range Hood
  • Basement Features: Full, Finished, Walk Out, Interior Access, Garage Access
  • Num of Baths: 3.0
  • Num of Full Baths: 3
  • Num of Half Baths: 0
  • Bathrooms Total Decimal: 3.00
  • Bathrooms Total Integer: 3
  • FireplaceFeatures: Dining Room, Family Room, Living Room
  • FireplaceYN: Yes
  • Fireplaces: 3
  • Flooring: Tile, Hardwood
  • Interior Features: Closet/Cabinets - Custom Built, Storage, Home Office
  • Laundry Features: Walk-in Storage, In Basement
  • Primary Bath: Yes
  • SpaYN: No
Exterior Features
  • Construction: Frame
  • Exterior Features: Patio, Storage Shed, Professional Landscaping, Sprinkler System
  • Exterior Features: Storage Shed, Professional Landscaping, Sprinkler System, Patio
  • Lot Description: Cul-De-Sac, Wooded
  • Patio And Porch Features: Patio
Parking Features
  • Attached Garage: Yes
  • Carport: No
  • Covered Spaces: 2.00
  • Garage: Yes
  • Garage Parking: Attached, Under, Garage Door Opener, Storage, Work Area, Paved Drive, Off-Street
  • Open Parking: Yes
  • Parking Features: Attached, Under, Garage Door Opener, Storage, Work Area, Paved Drive, Off-Street
  • Parking Features: Work Area, Off-Street
Utilities
  • Cooling: Central Air
  • Cooling: Yes
  • Heating: Central, Forced Air, Natural Gas
  • Heating: Yes
  • Sewer: City/Town Sewer
  • Water: Public
Room Information
Primary Bedroom
  • Room Primary Bedroom Features: Bathroom - Full,Flooring - Wood
  • Primary Bedroom Level: First Floor
Bedroom 2
  • Bedroom2 Features: Flooring - Wood
  • Bedroom2 Level: First
Bedroom 3
  • Bedroom3 Features: Flooring - Wood
  • Bedroom3 Level: First
Bathroom 1
  • Bathroom1 Features: Bathroom - Full,Bathroom - Double Vanity/Sink,Bathroom - Tiled With Tub & Shower
  • Bathroom1 Level: First
Bathroom 2
  • Bathroom2 Features: Bathroom - Full,Bathroom - Tiled With Shower Stall
  • Bathroom2 Level: First
Bathroom 3
  • Bathroom3 Features: Bathroom - Full,Bathroom - Tiled With Shower Stall
  • Bathroom3 Level: Basement
Dining Room
  • Dining Room Features: Wood / Coal / Pellet Stove
  • Dining Room Level: First
Family Room
  • Family Room Features: Flooring - Wood
  • Family Room Level: Basement
Kitchen
  • Kitchen Features: Flooring - Wood,Window(s) - Picture,Countertops - Stone/Granite/Solid,Kitchen Island,Breakfast Bar / Nook,Remodeled,Stainless Steel Appliances,Gas Stove
  • Kitchen Level: Main,First
Living Room
  • Room Living Room Features: Flooring - Wood
  • Room Living Room Level: First
Other Room 1
  • Room Office Features: Closet/Cabinets - Custom Built,Walk-in Storage
  • Room Office Level: Basement
Property Information
Property Info
  • Farm Land Area Units: Square Feet
  • WARRANTY: No
  • Lot Size Units: Acres
  • Road Frontage Type: Public
  • Disclosures: Seller plans to take the marble fireplace in the upstairs living room.
Tax Information
  • Tax ID: 260453
  • Assessments: $1,322,000
  • Book: 26966
  • Tax Year: 2026
  • Zoning: SR10
Building / Association Information
Living Characteristics
  • Beds Total: 3
Other Building Characteristics
  • Foundation: Concrete Perimeter
Complex & Association Information
  • Adult Community: No

Property History for 44 Windemere Road

DateEvent & SourcePriceAppreciation
Jul 9, 2026

Listed (Active)

MLS PIN #73547678

$1,500,000—
Jun 16, 2026

Canceled

MLS PIN #73522201

$1,595,000—
May 20, 2026

Listed (Active)

MLS PIN #73522201

$1,595,000—
DateEvent & SourcePrice
07/09/2026

Listed (Active)

MLS PIN #73547678

$1,500,000
06/16/2026

Canceled

MLS PIN #73522201

$1,595,000
05/20/2026

Listed (Active)

MLS PIN #73522201

$1,595,000

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 44 Windemere Road

Taxable ValueLand$1,148,000Additions$141,000Total$1,289,000
Tax Record2025$13,251 ($1,104 / month)
Home Facts
Beds3Baths2.5Total Finished SqFt1,512 SqFtAbove Grade Finished SqFt1,512 SqFtStories1Lot Size21,220 SqFtStyleSingle Family ResidenceYear Built1958ZoningSR10CountyNORFOLKAPNWELL M:097 R:017 S:Fireplace TypeHas Fireplace

Schools near 44 Windemere Road

This home is within Wellesley School District.
Rating
School
Type
Grades
Distance
Public - K to 5
Public - 6 to 8
Public - 9 to 12
Private - PK to 8
Rating
School
Distance
Sprague Elementary School
PublicK to 5

Wellesley Middle School
Public6 to 8

Wellesley High School
Public9 to 12

St Paul School
PrivatePK to 8

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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44 Windemere Road is a single family home for sale in Wellesley, MA 02481. This property was listed for sale on July 9, 2026 by Compass, it's currently listed at $1,500,000. It has been on the market for a total of 5 days and was last sold on August 10, 2009. This listing's school district is Wellesley School District. Nearby schools include Sprague Elementary School, Wellesley Middle School and Wellesley High School. 44 Windemere Road is a 3-bed, 3-bath, 2,447 sqft single family home built in 1958.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity.

The property listing data and information, or the images, set forth herein were provided to MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS. The property listing data and information, and the images, are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the images, set forth herein.