Is Wellesley, MA dog-friendly?

As of early 2026, 92% of users say it's dog friendly

Is parking easy in Wellesley, MA?

As of early 2026, 87% of users say parking is easy

Would people walk alone at night in Wellesley, MA?

As of early 2026, 85% of users say people would walk alone at night

Are yards well-kept in Wellesley, MA?

As of early 2026, 84% of users say yards are well-kept

Is a car needed in Wellesley, MA?

As of early 2026, 80% of users say car is needed

Does Wellesley, MA have sidewalks?

As of early 2026, 79% of users say there are sidewalks

Do kids play outside in Wellesley, MA?

As of early 2026, 76% of users say kids play outside

Does Wellesley, MA show holiday spirit?

As of early 2026, 75% of users say there's holiday spirit

Are the streets well-lit in Wellesley, MA?

As of early 2026, 74% of users say streets are well-lit

Is there wildlife in Wellesley, MA?

As of early 2026, 73% of users say there's wildlife

Is Wellesley, MA quiet?

As of early 2026, 72% of users say it's quiet

Do residents of Wellesley, MA plan to stay at least 5 years?

As of early 2026, 70% of users say they plan to stay for at least 5 years

Is Wellesley, MA walkable to restaurants?

As of early 2026, 67% of users say it's walkable to restaurants

Are neighbors friendly in Wellesley, MA?

As of early 2026, 66% of users say neighbors are friendly

Are there community events in Wellesley, MA?

As of early 2026, 65% of users say there are community events

Is Wellesley, MA walkable to grocery stores?

As of early 2026, 63% of users say it's walkable to grocery stores

FOR SALE

OPEN SAT, 11:30-1PM

0.49 ACRES

44 Windemere Rd
Wellesley, MA 02481

3 Beds
3 Baths
2,447 sqft (on 0.49 acres)

$1,500,000

Est. Mortgage $8,951/mo*

Get Pre-Qualified

$1,500,000

Est. Mortgage $8,951/mo*

Get Pre-Qualified

3 Beds

3 Baths

2,447 sqft

(on 0.49 acres)

Home Highlights

Parking

2 Car Garage

Outdoor

Patio

A/C

Heating & Cooling

HOA

None

Price/Sqft

$613

Listed

12 days ago

Local Information

Map ViewExplore the area around 44 Windemere Rd.
Schools1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

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 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.

Open House

Saturday, July 25

11:30 AM to 1:00 PM

Home Details for 44 Windemere Rd

Interior Features
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

Exterior Features
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

Days on Market
Days on Market: 12

Property Information
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

Price & Status
Price List Price: $1,500,000Price Per Sqft: $613

Active Status
MLS Status: Active

Location
Direction & Address City: Wellesley
School Information Elementary School: Sprague ElementaryJr High / Middle School: Wellesley Middle SchoolHigh School: Wellesley High School

Agent Information
Listing Agent Listing ID: 73547678

Building
Building Area Building Area: 2447 Square Feet

Community
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

HOA
No HOA

Lot Information
Lot Area: 0.49 acres

Miscellaneous
BasementMls Number: 73547678Above Grade Unfinished Area: 1744

Additional Information
Public TransportationShoppingTennis Court(s)ParkWalk/Jog TrailsGolfMedical FacilityBike PathConservation AreaHighway AccessHouse of WorshipPrivate SchoolPublic SchoolT-StationUniversity

Last check for updates: about 20 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.

Market trends in Wellesley

Last updated June 2026

Avg. sale price

$1.99M

$300KMoM

Sale-to-List Price

100.1%

1.4%MoM

Price per sq ft

$649

$56MoM

Available listings

112

1MoM

Price History for 44 Windemere Rd

Date	Price	Event	Source
07/09/2026	$1,500,000	Listed For Sale	MLS PIN #73547678

06/16/2026	$1,595,000	ListingRemoved	MLS PIN #73522201

05/21/2026	$1,595,000	Listed For Sale	MLS PIN #73522201

08/07/2009	$560,000	Sold	N/A
Recording Date 08/07/2009 County Transfer Tax N/A Total Transfer Tax N/A
05/16/2009	$615,000	PriceChange	Agent Provided
Price Change $20,000 (3%)
05/01/2009	$595,000	Listed For Sale	Agent Provided

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Property Tax and Assessment

Year	2025
Tax	$13,251
Assessment	$1,289,000

Home facts updated by county records

Comparable Sales for 44 Windemere Rd

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
35 Windemere Rd, Wellesley, MA	0.05	Single-Family Home	$1,275,000	07/30/25	3	2.5	1,774
4 Arnold Rd, Wellesley, MA	0.20	Single-Family Home	$1,750,000	09/23/25	4	2.5	3,156
33 Upwey Rd, Wellesley, MA	0.14	Single-Family Home	$1,850,000	07/31/25	4	2.5	3,346
32 Donizetti St, Wellesley, MA	0.31	Single-Family Home	$1,610,000	01/27/26	4	2.5	1,958
1 Roberts Rd, Wellesley, MA	0.34	Single-Family Home	$1,365,000	10/24/25	3	3	2,499
15 Barnstable Rd, Wellesley, MA	0.26	Single-Family Home	$2,500,000	08/14/25	4	4	3,097
15 Clifton Rd, Wellesley, MA	0.34	Single-Family Home	$1,635,650	04/16/26	4	2.5	2,112
69 Donizetti St, Wellesley, MA	0.26	Single-Family Home	$1,560,000	06/18/26	3	2	2,786
36 Donizetti St, Wellesley, MA	0.29	Single-Family Home	$1,300,000	08/26/25	3	2.5	1,697

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Get a sense of prices in the area by checking nearby homes.

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FOR SALE
0.31 ACRES
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Zhichao Chen, Space Realty
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3D VIEW
0.31 ACRES
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Erica Lockberg, Berkshire Hathaway HomeServices Town and Country Real Estate
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Teri Adler, MGS Group Real Estate LTD - Wellesley
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Janet Giesser, Rutledge Properties
OFF MARKET
Est. $3,437,400
4 bd
4.5 ba
4,620 sqft
23 Wall St,
Wellesley, MA 02481
Melissa Dailey, Coldwell Banker Realty - Wellesley
OFF MARKET
Est. $3,018,200
4 bd
4.5 ba
3,964 sqft
33 Chatham Cir,
Wellesley, MA 02481
The Madden David Real Estate Group, Coldwell Banker Realty - Wellesley
OFF MARKET
Est. $2,129,500
3 bd
3 ba
2,902 sqft
19 Wall St,
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Ezra Stillman, Hammond Residential Real Estate

Skip to first item

Additional Cost

Assigned Schools

These are the assigned schools for 44 Windemere Rd.

View nearby schools on GreatSchools

The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

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.

Mike Holiday
Resident
1y ago
"Everyone walks their dogs and lets their dogs say hello, most often. People know each other. It’s a great community"
0
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Emilyperrottet
Resident
2y ago
"Nothing. It’s a changing neighborhood with a mix of old and new homes. Most of the homes are old and run down. "
0
Flag
Emilyperrottet
Resident
2y ago
"I take the Commuter rail from Wellesley to the T subway. 1.5 hours to Cambridge from south station. "
0
Flag
Trulia User
Resident
4y ago
"Lots of trails and other dogs in the area, many pet stores in the area as well. Dogs are well behaved and friendly. "
0
Flag
Shirley L.
Resident
6y ago
"The walking paths and yearly town celebrations are wonderful! A great sense of community and great schools. "
0
Flag
Sdipietro369
Visitor
6y ago
"I am a visitor to this area. The neighborhood seems very nice with Babson College right around the corner. Shops within a close distance. "
3
Flag
Katrina C.
Resident
6y ago
"You feel you're kids are safe here in town. Everyone is friendly and we're all neighbors. It's a lovely town with a community feeling. "
2
Flag
Jamie.solomon1
Resident
6y ago
"I lived in Weston for two years and it’s a delightful town, with gorgeous land and large houses. Usually at least an acre"
1
Flag
Cmt138
Resident
7y ago
"Great access to commuter rail from either Wellesley Square or Wellesley Hills. Easy 10-15 min walk. Better parking from Wellesley Square. Usually takes about 1/2 hour to Back Bay. Driving into Boston can take a little more time with traffic to cross town to Mass Pike."
2
Flag
Laura M.
Resident
7y ago
"There are lots of dogs in our neighborhood- people walk them all the time. Dogs are welcome at Morse’s pond in the off season. "
1
Flag
Bruce C.
Resident
7y ago
"Lots of other dog owners who walk their dogs all the time. Also plenty of space to run with dogs on a trail or away from streets. "
1
Flag
Keith S.
Resident
8y ago
"Lots of trails and public spaces. Nationally acclaimed colleges. Variety of great shops and restaurants."
0
Flag
Srodousakis
Resident
8y ago
"Wellesley is a beautiful but very privileged neighborhood. It is very safe and people are friendly. Schools are great! There is a cute downtown and generally it’s a great place to raise kids. "
0
Flag
Molly R.
Resident
8y ago
"i love my neighborhood. everyone is so kind and welcoming. we often times have little gatherings or block parties. everyone knows each other and we are a very close community. "
0
Flag
Victoria V.
Resident
8y ago
"That I live on route 16 and nobody lets me out of my driveway in the morning and I have to leave for work an hour early just because of that."
0
Flag

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.
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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.

44 Windemere Rd Wellesley, MA 02481

$1,500,000

$1,500,000

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44 Windemere Rd
Wellesley, MA 02481