24 Windsor Rd, Wellesley, MA 02481
OFF MARKET

24 Windsor Rd
Wellesley, MA 02481

  • 5 Beds
  • 4 Baths
  • 3,653 sqft (on 0.38 acres)

$2,835,700

Trulia Estimate
as of May 25, 2026
Est. Refi. Payment $16,571/mo*

$2,835,700

Trulia Estimate
as of May 25, 2026
Est. Refi. Payment $16,571/mo*
5 Beds
4 Baths
3,653 sqft
(on 0.38 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

Sun-filled brick mission-style colonial in quiet Country Club neighborhood adjacent to Centennial Park Reservation, 42-acres of town park land. High ceilings, one-of-a-kind craftsman-built mantels and cabinetry with leaded glass doors and original finishes, egg and dart moldings on all three floors, large living room with wood-burning fireplace, fabulous dining room with original wainscoting and china cabinets, light-filled granite and stainless steel kitchen, breakfast room and family room with plantation shutters, and library with built-in cabinets and desk. Master suite comprises three closets, marble master bath, two-person designer shower with five shower sprays, hot-tub, custom double-sink cabinet, vaulted ceiling, plantation shutters and radiant heat in floor. Second master bedroom includes views of surrounding forests, vaulted ceiling, two double closets and ensuite bath with radiant heat. Bedroom #3 has walk-in closet. Third floor has two bedrooms with built in dressers and sunny bathroom. Attic eaves have storage space. Ground floor family room with gas fireplace, built-ins, refrigerator and half-bath is perfect for tweens and teens. Hardwood floors throughout. Full basement with, garage stall. Detached second garage festooned with roses. Large deck overlooks perennial gardens, roses, and forest park land. Slate and copper roof, recently overhauled. Original details have been preserved throughout this house, and all renovations consist of top-quality design, workmanship and materials. Walk to the train, bank and shopping.

Neighborhood Description

Dead end street with little traffic. You can walk the neighborhood with dogs or baby strollers and feel safe from traffic. Friendly neighbors on the circle enjoy neighborhood events - annual Progressive Dinner, and annual Halloween Party on the Triangle.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
No Info
Outdoor
Deck
A/C
Heating only
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 24 Windsor Rd

Interior Features

Interior Details
BasementAtticNumber of Rooms: 11Types of Rooms: Walk In Closet, Breakfast Nook, Dining Room, Family Room, Laundry Room, Master Bath, Mud Room, Office, Recreation RoomCeiling Fan
Heating & Cooling
Heating: Baseboard, Radiant, GasHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 3Floors: Hardwood
Appliances & Utilities
Cable ReadyDishwasherDisposalRefrigerator
Fireplace & Spa
FireplaceJetted Bath Tub
Windows, Doors, Floors & Walls
Double Paned Windows

Exterior Features

Exterior Home Features
Roof: SlateDeckExterior: BrickGardenLawn
Parking & Garage
Parking Spaces: 2

Property Information

Year Built
Year Built: 1915Year Updated: 2000
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 0.38 acres

Price History for 24 Windsor Rd

DatePriceEventSource
03/24/2021ListingRemovedN/A
08/22/2011$2,225,000ListingRemovedN/A
02/23/2011$2,225,000Listed For SaleN/A
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Property Tax and Assessment

Year2025
Tax$20,077
Assessment$1,953,000
Home facts updated by county records

Comparable Sales for 24 Windsor Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
0.31
Single-Family Home
$2,335,000
07/01/25
5
3.5
4,635
0.21
Single-Family Home
$2,600,000
01/09/26
4
3.5
3,705
0.16
Single-Family Home
$2,900,000
07/24/25
4
4.5
3,272
0.37
Single-Family Home
$2,625,000
11/03/25
4
3.5
4,720
0.41
Single-Family Home
$2,625,000
04/30/26
4
3.5
3,433
0.39
Single-Family Home
$2,354,000
12/24/25
4
4.5
4,211
0.12
Single-Family Home
$6,187,500
11/12/25
6
7
7,037
0.38
Single-Family Home
$3,300,000
08/08/25
6
5.5
4,897
0.44
Single-Family Home
$3,300,000
08/01/25
4
4.5
4,200
0.46
Single-Family Home
$1,675,000
09/08/25
5
2.5
3,347

Nearby homes

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Assigned Schools

These are the assigned schools for 24 Windsor Rd.
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 123 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

  • 76 % 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

  • 62 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Mike Holiday
    "Everyone walks their dogs and lets their dogs say hello, most often. People know each other. It’s a great community"
  • Emilyperrottet
    "Nothing. It’s a changing neighborhood with a mix of old and new homes. Most of the homes are old and run down. "
  • Emilyperrottet
    "I take the Commuter rail from Wellesley to the T subway. 1.5 hours to Cambridge from south station. "
  • Trulia User
    "Lots of trails and other dogs in the area, many pet stores in the area as well. Dogs are well behaved and friendly. "
  • Shirley L.
    "The walking paths and yearly town celebrations are wonderful! A great sense of community and great schools. "
  • Sdipietro369
    "I am a visitor to this area. The neighborhood seems very nice with Babson College right around the corner. Shops within a close distance. "
  • Katrina C.
    "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. "
  • Jamie.solomon1
    "I lived in Weston for two years and it’s a delightful town, with gorgeous land and large houses. Usually at least an acre"
  • Cmt138
    "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."
  • Laura M.
    "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. "
  • Bruce C.
    "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. "
  • Keith S.
    "Lots of trails and public spaces. Nationally acclaimed colleges. Variety of great shops and restaurants."
  • Srodousakis
    "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. "
  • Molly R.
    "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. "
  • Victoria V.
    "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."

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24 Windsor Rd, Wellesley, MA 02481 is a 5 bedroom, 4 bathroom, 3,653 sqft single-family home built in 1915. This property is not currently available for sale. The current Trulia Estimate for 24 Windsor Rd is $2,835,700.