55 Cliff Rd, Wellesley, MA 02481
OFF MARKET

55 Cliff Rd
Wellesley, MA 02481

  • 4 Beds
  • 4 Baths
  • 5,628 sqft (on 0.62 acres)

$4,001,000

Trulia Estimate
as of Jun 18, 2026
Est. Refi. Payment $23,351/mo*
Refinance Your Home

$4,001,000

Trulia Estimate
as of Jun 18, 2026
Est. Refi. Payment $23,351/mo*
Refinance Your Home
4 Beds
4 Baths
5,628 sqft
(on 0.62 acres)

Local Information

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

Description

Exquisite brick colonial offers extraordinary curb appeal and more! Beautifully renovated to the highest quality and sited on a private oasis of lush, manicured grounds, this sun-splashed 4-5 bedroom residence offers a seamless blend of sophisticated entertaining and work from home spaces, smart home features, and chic, casual comfort. High ceilings, sparkling hardwood floors, and fine millwork greet you upon entering the gracious foyer opening to fireplaced living room with french doors leading to a study and an office. Entertainment sized dining room leads to butler's pantry, sunroom, and open kitchen/family room with gas fireplace opening to a stunning slate patio with stone wall and gardens. Second floor offers luxurious master suite with walk-in closet and newly renovated bath, two additional bedrooms, laundry and bath. Third floor includes a two room suite with fireplace and full bath. Walk-out lower level great room with coffered ceilings, wine room and spacious mudroom.Turnkey!
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
Garage
Outdoor
Patio
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 55 Cliff Rd

Interior Features

Heating & Cooling
Heating: Forced Air, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 3Floors: Hardwood
Interior Details
Number of Rooms: 11
Fireplace & Spa
Fireplace
Security
Security System

Exterior Features

Exterior Home Features
Roof: SlateExterior: Stone, BrickPatioSprinkler System
Parking & Garage
GarageParking Spaces: 3Parking: Garage Attached

Property Information

Year Built
Year Built: 1928Year Updated: 1998
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 0.62 acres

Price History for 55 Cliff Rd

DatePriceEventSource
12/15/2020$2,899,000Sold
N/A
10/18/2020$2,899,000PendingAgent Provided
10/16/2020$2,899,000Listed For SaleAgent Provided
08/14/2009$2,380,000Sold
N/A
04/07/2000$2,177,000Sold
N/A
09/08/1997$975,000Sold
N/A

Market trends in Wellesley

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
111
3MoM
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Property Tax and Assessment

Year2025
Tax$32,927
Assessment$3,203,000
Home facts updated by county records

Homeowner tools

Estimated monthly rent$7,899/mo
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Homes for rent near 55 Cliff Rd

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Comparable Sales for 55 Cliff Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
10 Lanark Rd, Wellesley, MA
0.11
Single-Family Home
$4,400,000
07/10/25
6
3.5
7,404
3 Garden Rd, Wellesley, MA
0.28
Single-Family Home
$2,500,000
03/05/26
4
3.5
4,870
26 Edmunds Rd, Wellesley, MA
0.40
Single-Family Home
$3,115,000
01/09/26
4
3.5
4,294
40 Chestnut St, Wellesley, MA
0.07
Single-Family Home
$2,450,000
05/06/26
5
3.5
3,369
44 Bradford Rd, Wellesley, MA
0.23
Single-Family Home
$3,100,000
06/02/26
5
5.5
4,785
5 Cliff Rd, Wellesley, MA
0.33
Single-Family Home
$3,200,000
07/02/25
5
4.5
5,210
7 Garden Rd, Wellesley, MA
0.31
Single-Family Home
$2,059,981
09/25/25
5
3.5
4,643
36 Old Farm Rd, Wellesley, MA
0.44
Single-Family Home
$3,475,000
07/31/25
5
5.5
5,359
7 Cliff Rd, Wellesley, MA
0.33
Single-Family Home
$1,865,000
04/02/26
5
3.5
3,774
81 Garden Rd, Wellesley, MA
0.24
Single-Family Home
$1,875,000
06/19/25
5
3
3,217

Nearby homes

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Assigned Schools

These are the assigned schools for 55 Cliff 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
    "Everyone walks their dogs and lets their dogs say hello, most often. People know each other. It’s a great community"
    0
    Flag
  • Emilyperrottet
    "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
    "I take the Commuter rail from Wellesley to the T subway. 1.5 hours to Cambridge from south station. "
    0
    Flag
  • 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. "
    0
    Flag
  • Shirley L.
    "The walking paths and yearly town celebrations are wonderful! A great sense of community and great schools. "
    0
    Flag
  • 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. "
    3
    Flag
  • 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. "
    2
    Flag
  • 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"
    1
    Flag
  • 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."
    2
    Flag
  • 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. "
    1
    Flag
  • 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. "
    1
    Flag
  • Keith S.
    "Lots of trails and public spaces. Nationally acclaimed colleges. Variety of great shops and restaurants."
    0
    Flag
  • 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. "
    0
    Flag
  • 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. "
    0
    Flag
  • 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."
    0
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Homes for sale near 55 Cliff Rd

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Off Market Homes Near 55 Cliff Rd

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55 Cliff Rd, Wellesley, MA 02481 is a 4 bedroom, 5 bathroom, 5,628 sqft single-family home built in 1928. This property is not currently available for sale. 55 Cliff Rd was last sold on Dec 15, 2020 for $2,899,000. The current Trulia Estimate for 55 Cliff Rd is $4,001,000.