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44 Windemere RdWellesley, MA 02481

For Sale

$1,450,000

Smart Buyer Rebate $7,250

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.

Last updated September 14, 2026

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Source: MLSPin #73547678

Listing Facts

  • TypeSingle-family
  • NeighborhoodLinden Square
  • Bedrooms3
  • Bathrooms3
  • Days on Prevu68
  • Taxes$13,444/year
  • Size2,447 sqft
  • Price per sqft$593

Amenities

  • Dishwasher
  • Private Outdoor Space
  • Washer/Dryer
  • Air Conditioning
  • Parking

Location

Mortgage Calculator

Listing History

09/11/2026
Price Decreased
$1,450,000
07/09/2026
Listed by
$1,500,000
  1. 09/11/2026$1,450,000
    Price Decreased
  2. 07/09/2026$1,500,000
    Listed by

Property Details for 44 Windemere Rd

Association

Amenities

  • Community Features: Tennis Court(s), Park, Golf

Exterior

Construction

  • Year Built: 1958
  • Year Built Details: Actual
  • Architectural Style: Ranch, Raised Ranch
  • Construction Materials: Frame
  • Exterior Features: Storage

Features

  • Other Structures: Storage
  • Patio And Porch Features: Patio

Measurements

  • Building Area Total: 2,447
  • Building Area Units: Square Feet
  • Lot Features: Cul-De-Sac, Wooded, Landscaped
  • Lot Size Acres: 0.49
  • Lot Size Area: 0
  • Lot Size Square Feet: 21,220
  • Lot Size Units: Acres

Financial

Taxes

  • Parcel Number: 260453
  • Tax Annual Amount: $13,444.00
  • Tax Assessed Value: $1,322,000.00
  • Tax Year: 2026

Interior

Features

  • Appliances: Range, Dishwasher, Disposal, Refrigerator, Freezer, Washer, Dryer, Range Hood
  • Fireplace Features: Dining Room, Family Room, Living Room
  • Fireplace: Yes
  • Fireplaces Total: 3
  • Flooring: Tile, Hardwood
  • Interior Features: Storage, Master Downstairs

Measurements

  • Living Area: 2,447
  • Living Area Source: Other

Rooms

  • Basement: Full, Finished, Walk-Out Access, Interior Entry
  • Has Basement: Yes
  • Bathrooms Full: 3
  • Bathrooms Total Integer: 3
  • Bedrooms Total: 3
  • Rooms Total: 13

Parking

Parking

  • Attached Garage: Yes
  • Covered Spaces: 2
  • Garage Spaces: 2
  • Garage: Yes
  • Open Parking Spaces: 4
  • Open Parking: Yes
  • Parking Features: Paved, Attached, Garage Door Opener, Storage, Workshop In Garage, Off Street, Garage
  • Parking Total: 6

Schools

Elementary School

  • Elementary School: Sprague Elementary

High School

  • High School: Wellesley High School

Middle or Junior School

  • Middle Or Junior School: Wellesley Middle School

Utilities

Equipment

  • Cooling: Central Air
  • Has Cooling: Yes
  • Heating: Natural Gas, Central, Forced Air
  • Has Heating: Yes
  • Laundry Features: In Basement
  • Sewer: Public Sewer
  • Water Source: Public

Frequently Asked Questions

How many bedrooms and bathrooms does this single-family home have?

There are 3 bedrooms and 3 bathrooms in this single-family home at 44 Windemere Rd.

What schools are nearby to 44 Windemere Rd?

Nearby schools include the Sprague Elementary, Wellesley Middle School, and Wellesley High School.

Does this single-family home have parking?

Yes, there are 2 parking spaces available for 44 Windemere Rd.

What are the annual taxes for 44 Windemere Rd?

Annual taxes for this single-family home are estimated at $13,444.

How does 44 Windemere Rd compare to other single-family homes in Linden Square?

This single-family home is listed 32% below the average price for single-family homes in Linden Square and has been on the market for 17 more days than the typical home in this area.

What is the square footage on this single-family home?

According to the MLS, this listing is 2,447 sqft.

44 Windemere Rd is a 3-bedroom, 3-bath single-family home for sale in Wellesley MA 02481. Listed on Prevu for 68 days at $1,450,000. This includes a recent price decrease of $50,000. This residence features 2,447 square feet of living space, located in Linden Square. The median listing price for single-family homes in this area is $1,612,000. Nearby schools include Sprague Elementary, Wellesley Middle School, and Wellesley High School. Additional amenities include private outdoor space, dishwasher, air conditioning, parking, and washer/dryer. Explore more single-family home listings in Norfolk County.

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. 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, leasing or renting 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, leasing or renting. MLS Property Information Network, Inc. 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.

Full MLS Disclaimers

Rebate estimate is indicative only and based on listing price and estimated buyer's agent commission paid by owner, if applicable. Final rebates are subject to Terms of Use and may vary due to final negotiated transaction terms.