$1,500,000
3 Beds
3 Baths
2,447 sqft (on 0.49 acres)
44 Windemere Rd, Wellesley, MA 02481
Est. Mortgage $8,959/mo*
Get Pre-QualifiedHome Highlights
Single-Family Home
Built in 1958
0.49 acre lot
$613/sqft
2 Car Garage
Local Information
- Map ViewExplore the area around 44 Windemere Rd.
- Schools1 Elementary School1 Middle School1 High School
- Shop & Eat
-- mins to
About this House
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 check for updates: about 8 hours ago
Listing courtesy of Aranson Maguire Group, (207) 252-6771
Compass, (617) 206-3333
Source: MLS PIN, MLS#73547678
Also Listed on MLS PIN.
Home Details for 44 Windemere Rd
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Interior Details Basement: Full,Finished,Walk-Out Access,Interior Entry,Garage AccessNumber of Rooms: 13Types of Rooms: Master Bedroom, Bedroom 2, Bedroom 3, Master Bathroom, Bathroom 1, Bathroom 2, Bathroom 3, Dining Room, Family Room, Kitchen, Living Room, Office |
Beds & Baths Number of Bedrooms: 3Number of Bathrooms: 3Number of Bathrooms (full): 3 |
Dimensions and Layout Living Area: 2447 Square Feet |
Appliances & Utilities Appliances: Range, Dishwasher, Disposal, Refrigerator, Freezer, Washer, Dryer, Range HoodDishwasherDisposalDryerLaundry: Walk-in Storage,In BasementRefrigeratorWasher |
Heating & Cooling Heating: Central,Forced Air,Natural GasHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Central |
Fireplace & Spa Number of Fireplaces: 3Fireplace: Dining Room, Family Room, Living RoomHas a FireplaceNo Spa |
Windows, Doors, Floors & Walls Flooring: Tile, Hardwood |
Levels, Entrance, & Accessibility Floors: Tile, Hardwood |
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Exterior Home Features Patio / Porch: PatioExterior: Patio, Storage, Professional Landscaping, Sprinkler SystemFoundation: Concrete PerimeterSprinkler System |
Parking & Garage Number of Garage Spaces: 2Number of Covered Spaces: 2Open Parking Spaces: 4No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 6Parking: Attached,Under,Garage Door Opener,Storage,Workshop in Garage,Paved Drive,Off Street |
Frontage Road Frontage: PublicNot on Waterfront |
Water & Sewer Sewer: Public Sewer |
Finished Area Finished Area (above surface): 1744Finished Area (below surface): 703 |
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Days on Market: 58 |
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Year Built Year Built: 1958 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Ranch,Raised Ranch |
Building Construction Materials: FrameNot Attached PropertyDoes Not Include Home Warranty |
Property Information Parcel Number: 260453 |
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Price List Price: $1,500,000Price Per Sqft: $613 |
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MLS Status: Active |
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Direction & Address City: Wellesley |
School Information Elementary School: Sprague ElementaryJr High / Middle School: Wellesley Middle SchoolHigh School: Wellesley High School |
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Listing Agent Listing ID: 73547678 |
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Building Area Building Area: 2447 Square Feet |
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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, UniversityNot Senior Community |
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No HOA |
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Lot Area: 0.49 acres |
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BasementMls Number: 73547678Above Grade Unfinished Area: 1744 |
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Public TransportationShoppingTennis Court(s)ParkWalk/Jog TrailsGolfMedical FacilityBike PathConservation AreaHighway AccessHouse of WorshipPrivate SchoolPublic SchoolT-StationUniversity |
Around this home
What Locals Say about Wellesley
At least 124 Trulia users voted on each feature.
92 % Say it's dog friendly
87 % Say parking is easy
85 % Say people would walk alone at night
84 % Say yards are well-kept
80 % Say car is needed
79 % Say there are sidewalks
76 % Say kids play outside
75 % Say there's holiday spirit
74 % Say streets are well-lit
73 % Say there's wildlife
72 % Say it's quiet
70 % Say they plan to stay for at least 5 years
67 % Say it's walkable to restaurants
66 % Say neighbors are friendly
65 % Say there are community events
63 % Say it's walkable to grocery stores
Sourced by Trulia users. Learn more about our methodology.
Market trends in Wellesley
Last updated July 2026
Avg. sale price
$2.15M
$161KMoM
Sale-to-List Price
100.6%
0.4%MoM
Price per sq ft
$666
$18MoM
Available listings
87
25MoM
Home Value
Trulia Estimate
$1.45MSince last month
Decreased$40K (-2.6%)Since last year
Decreased$32K (-2.2%)Since last sale
Increased$894K (+159.7%)Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.
Trulia Estimate
The of this home's value increased by +67% in the last 10 years
| Month | Estimated value |
|---|---|
2026 | |
| September 2026 | $1.45M |
| August 2026 | $1.45M |
| July 2026 | $1.49M |
| June 2026 | $1.52M |
| May 2026 | $1.67M |
| April 2026 | $1.54M |
| March 2026 | $1.61M |
| February 2026 | $1.53M |
| January 2026 | $1.5M |
2025 | |
2024 | |
2023 | |
2022 | |
2021 | |
2020 | |
2019 | |
2018 | |
2017 | |
2016 | |
Comparable sales
These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.24 | Single-Family Home | $1,177,000 | 08/06/26 | 3 | 2.5 | 3,129 | |
0.20 | Single-Family Home | $1,750,000 | 09/23/25 | 4 | 2.5 | 3,156 | |
0.31 | Single-Family Home | $1,610,000 | 01/27/26 | 4 | 2.5 | 1,958 | |
0.34 | Single-Family Home | $1,365,000 | 10/24/25 | 3 | 3 | 2,499 | |
0.34 | Single-Family Home | $1,635,650 | 04/16/26 | 4 | 2.5 | 2,112 | |
0.26 | Single-Family Home | $1,560,000 | 06/18/26 | 3 | 2 | 2,786 | |
0.21 | Single-Family Home | $1,913,000 | 05/20/26 | 6 | 3 | 2,980 | |
0.23 | Single-Family Home | $2,300,000 | 04/07/26 | 5 | 3.5 | 3,985 | |
0.31 | Single-Family Home | $2,525,000 | 06/26/26 | 4 | 3.5 | 3,497 |
Nearby home prices
Get a sense of expected prices in the area by checking the value of nearby homes.Address | Distance | Price | Bed | Bath | Sqft | Status |
|---|---|---|---|---|---|---|
0.05 | $1,322,100 | 3 | 2.5 | 1,774 | Off Market | |
0.11 | $1,755,000 | 3 | 2.5 | 2,188 | Off Market | |
0.15 | $2,450,000 | 4 | 4 | 4,676 | Recently Sold | |
0.14 | $4,250,000 | 5 | 6.5 | 7,461 | Recently Sold | |
0.11 | $2,295,000 | 4 | 3.5 | 3,776 | For Sale | |
0.17 | $2,296,700 | 4 | 3.5 | 3,832 | Off Market | |
0.12 | $2,220,300 | 4 | 3.5 | 3,286 | Off Market | |
0.17 | $3,360,300 | 4 | 4.5 | 4,620 | Off Market | |
0.13 | $2,878,400 | 4 | 4.5 | 3,964 | Off Market | |
0.18 | $2,092,000 | 3 | 3 | 2,902 | Off Market | |
0.19 | $2,895,000 | 5 | 4.5 | 3,706 | Recently Sold |
Price and Tax history
| Date | Event | Price |
|---|---|---|
Jul 9, 2026 Source: MLS PIN #73547678 | Listed For Sale | $1,500,000 |
Jun 16, 2026 Source: MLS PIN #73522201 | ListingRemoved | $1,595,000 |
May 21, 2026 Source: MLS PIN #73522201 | Listed For Sale | $1,595,000 |
Aug 7, 2009 Source: N/A | Sold | $560,000 |
May 16, 2009 Source: Agent Provided | PriceChange | $615,000 Price increased by 3% |
May 1, 2009 Source: Agent Provided | Listed For Sale | $595,000 |
| Year | Property tax | Tax assessment |
|---|---|---|
| 2025 | $13,251 | $1,289,000 |
Home facts updated by county records
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections
Aranson Maguire Group, Compass, (617) 206-3333
Agent Phone: (207) 252-6771
The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information 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. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein.
The MLS listing information displayed is deemed reliable, but is not guaranteed accurate by the MLS.
The MLS listing information displayed is deemed reliable, but is not guaranteed accurate by the MLS.
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Frequently asked questions about 44 Windemere Rd
- What is the estimated monthly payment for 44 Windemere Rd?Based on a $1,500,000 list price with 20% down at today's rates, the estimated monthly payment for 44 Windemere Rd in Wellesley, MA is approximately $9,276 (about $7,926 principal & interest, $1,275 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
- How does the list price for 44 Windemere Rd compare to homes in Wellesley?44 Windemere Rd in Wellesley, MA is listed at $1,500,000, about 30% below the $2.15M median sale price in Wellesley.
- What do residents say about Wellesley?Residents describe Wellesley, MA as dog-friendly, easy to park in, and well-kept. Most residents say you need a car. See homes for sale in Wellesley, MA.
- What are the closest schools to 44 Windemere Rd?The closest schools to 44 Windemere Rd in Wellesley, MA are Sprague Elementary School (rated 9/10), Wellesley High School (rated 10/10), Wellesley Middle School (rated 8/10).
- Does 44 Windemere Rd have air conditioning?Yes, 44 Windemere Rd in Wellesley, MA has air conditioning.
- Does 44 Windemere Rd have laundry facilities?Yes, 44 Windemere Rd in Wellesley, MA has in-unit laundry.
44 Windemere Rd, Wellesley, MA 02481 is a 3 bedroom, 3 bathroom, 2,447 sqft single-family home built in 1958. This property is currently available for sale and was listed by MLS PIN on Jul 9, 2026. The MLS # for this home is MLS# 73547678.