For sale

Price cut: $50K (9/10)

$1,450,000

44 Windemere Rd, Wellesley, MA 02481

3beds

2,447sqft

$9,057/mo

Get pre-qualified

Single Family Residence

Built in 1958

0.49 Acres Lot

$1,399,800 Zestimate^®

$593/sqft

$-- HOA

What's special

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.

65 days
1,243
20

Facts & features

Interior

Bedrooms & bathrooms

Bedrooms: 3
Bathrooms: 3
Full bathrooms: 3

Primary bedroom

Features: Bathroom - Full, Flooring - Wood
Level: First

Bedroom 2

Features: Flooring - Wood
Level: First

Bedroom 3

Features: Flooring - Wood
Level: First

Primary bathroom

Features: Yes

Bathroom 1

Features: Bathroom - Full, Bathroom - Double Vanity/Sink, Bathroom - Tiled With Tub & Shower
Level: First

Bathroom 2

Features: Bathroom - Full, Bathroom - Tiled With Shower Stall
Level: First

Bathroom 3

Features: Bathroom - Full, Bathroom - Tiled With Shower Stall
Level: Basement

Dining room

Features: Wood / Coal / Pellet Stove
Level: First

Family room

Features: Flooring - Wood
Level: Basement

Kitchen

Features: Flooring - Wood, Window(s) - Picture, Countertops - Stone/Granite/Solid, Kitchen Island, Breakfast Bar / Nook, Remodeled, Stainless Steel Appliances, Gas Stove
Level: Main,First

Living room

Features: Flooring - Wood
Level: First

Office

Features: Closet/Cabinets - Custom Built, Walk-in Storage
Level: Basement

Heating

Central, Forced Air, Natural Gas

Cooling

Central Air

Appliances

Included: Range, Dishwasher, Disposal, Refrigerator, Freezer, Washer, Dryer, Range Hood
Laundry: Walk-in Storage, In Basement

Features

Closet/Cabinets - Custom Built, Storage, Home Office
Flooring: Tile, Hardwood
Basement: Full,Finished,Walk-Out Access,Interior Entry,Garage Access
Number of fireplaces: 3
Fireplace features: Dining Room, Family Room, Living Room

Interior area

Total structure area: 2,447
Total interior livable area: 2,447 sqft
Finished area above ground: 1,744
Finished area below ground: 703

Property

Parking

Total spaces: 6
Parking features: Attached, Under, Garage Door Opener, Storage, Workshop in Garage, Paved Drive, Off Street
Attached garage spaces: 2
Uncovered spaces: 4

Features

Patio & porch: Patio
Exterior features: Patio, Storage, Professional Landscaping, Sprinkler System

Lot

Size: 0.49 Acres
Features: Cul-De-Sac, Wooded

Details

Parcel number: 260453
Zoning: SR10

Construction

Type & style

Home type: SingleFamily
Architectural style: Ranch,Raised Ranch
Property subtype: Single Family Residence

Materials

Frame
Foundation: Concrete Perimeter

Condition

Year built: 1958

Utilities & green energy

Sewer: Public Sewer
Water: Public

Community & HOA

Community

Features: Public Transportation, Shopping, Tennis Court(s), Park, Walk/Jog Trails, Golf, Medical Facility, Bike Path, Conservation Area, Highway Access, House of Worship, Private School, Public School, T-Station, University

HOA

Has HOA: No

Location

Region: Wellesley

Financial & listing details

Price per square foot: $593/sqft
Tax assessed value: $1,322,000
Annual tax amount: $13,444
Date on market: 7/9/2026

Estimated market value

$1,399,800

$1.33M - $1.47M

$5,553/mo

Price history

Date	Event	Price
9/10/2026	Price change	$1,450,000-3.3%$593/sqft
Source: MLS PIN #73547678 Report a problem
7/9/2026	Listed for sale	$1,500,000-6%$613/sqft
Source: MLS PIN #73547678 Report a problem
6/16/2026	Listing removed	$1,595,000$652/sqft
Source: MLS PIN #73522201 Report a problem
5/21/2026	Listed for sale	$1,595,000+184.8%$652/sqft
Source: MLS PIN #73522201 Report a problem
8/7/2009	Sold	$560,000-8.9%$229/sqft
Source: Public Record Report a problem
5/16/2009	Price change	$615,000+3.4%$251/sqft
Source: NRT NewEngland #70909321 Report a problem
5/1/2009	Listed for sale	$595,000$243/sqft
Source: NRT NewEngland #70909321 Report a problem

Public tax history

Year	Property taxes	Tax assessment
2025	$13,251 +7.9%	$1,289,000 +9.2%
2024	$12,284 -3.3%	$1,180,000 +6.4%
2023	$12,698 +6.1%	$1,109,000 +8.2%
2022	$11,972 +3%	$1,025,000 +3.6%
2021	$11,621 +1.6%	$989,000
2020	$11,433 +3.8%	$989,000 +3.9%
2019	$11,015 +21%	$952,000 +24.9%
2018	$9,106 +1.2%	$762,000 -0.1%
2017	$8,996 +1.7%	$763,000 +2%
2016	$8,849 +12.4%	$748,000 +9.8%
2015	$7,872 +9.1%	$681,000 +9%
2014	$7,213 +4.4%	$625,000 +3.8%
2012	$6,911 +14.5%	$602,000 +14%
2011	$6,035 +7.4%	$528,000 -1.5%
2010	$5,617 +0.4%	$536,000 -9.3%
2009	$5,597 +3%	$591,000 -0.2%
2008	$5,435 +2.1%	$592,000 -1.3%
2007	$5,322 +7.5%	$600,000 +0.8%
2006	$4,950 +10%	$595,000 +11%
2005	$4,502 +22%	$536,000 +24.4%
2004	$3,689 +21.8%	$431,000 +15.5%
2003	$3,029 -13.2%	$373,000 -13.5%
2002	$3,491 +27.4%	$431,000 +55%
1999	$2,741	$278,000