14 Cliff Rd, Wellesley, MA 02481
OFF MARKET

14 Cliff Rd
Wellesley, MA 02481

  • 4 Beds
  • 3.5 Baths
  • 3,233 sqft (on 1.02 acres)

$2,673,200

Trulia Estimate
as of May 27, 2026
Est. Refi. Payment $15,710/mo*
Refinance Your Home

$2,673,200

Trulia Estimate
as of May 27, 2026
Est. Refi. Payment $15,710/mo*
Refinance Your Home
4 Beds
3.5 Baths
3,233 sqft
(on 1.02 acres)

Local Information

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

Description

Beautiful Brick Cliff Estates Colonial. Set far above and back from the street on a lovely acre lot with mature landscaping, this property allows for the perfect combination of privacy and in town convenience. One of the prettiest foyers in town with sun drenched stair case leads to living room and dining rooms which are resplendent in period appointments and gracious proportions. The kitchen has been meticulously updated with stainless steel appliances including 6 burner wolf range, sub zero and beautiful marble island with barstool seating. Adjoining cozy family room boasts a fireplace. 4/5 bedrooms and 3 baths on second floor. Walk up attic perfect for storage or future expansion. Detached 2 bay carriage house with slate roof to match the main house has a surprise storage area below. A very short walk to Wellesley Hills Commuter Train and shops. Rise above the everyday...this is a special opportunity.
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
No Info

Home Details for 14 Cliff Rd

Interior Features

Interior Details
BasementNumber of Rooms: 9Types of Rooms: Walk In Closet, Dining Room, Family Room, Laundry Room, Library, Master Bath, Mud Room, Office, Workshop
Heating & Cooling
Heating: Baseboard, Other, Radiant, GasAir ConditioningCooling System: CentralHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 2Floors: Tile, Carpet, Hardwood, Slate
Appliances & Utilities
Cable ReadyDishwasherDisposalDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: SlateExterior: BrickGardenLawnPatioSprinkler System
Parking & Garage
GarageParking Spaces: 7Parking: Garage Detached, Off Street

Property Information

Year Built
Year Built: 1921
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 1.02 acres

Price History for 14 Cliff Rd

DatePriceEventSource
03/30/2023$2,500,000Sold
N/A
12/01/2016$1,554,375Sold
N/A
09/21/2016$1,645,000Listed For SaleAgent Provided
01/18/2005$1,325,000Sold
N/A
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Property Tax and Assessment

Year2025
Tax$25,978
Assessment$2,527,000
Home facts updated by county records

Comparable Sales for 14 Cliff Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
7 Cliff Rd, Wellesley, MA
0.08
Single-Family Home
$1,865,000
04/02/26
5
3.5
3,774
3 Garden Rd, Wellesley, MA
0.05
Single-Family Home
$2,500,000
03/05/26
4
3.5
4,870
5 Cliff Rd, Wellesley, MA
0.06
Single-Family Home
$3,200,000
07/02/25
5
4.5
5,210
7 Garden Rd, Wellesley, MA
0.10
Single-Family Home
$2,059,981
09/25/25
5
3.5
4,643
26 Edmunds Rd, Wellesley, MA
0.29
Single-Family Home
$3,115,000
01/09/26
4
3.5
4,294
500 Worcester St, Wellesley, MA
0.13
Single-Family Home
$1,340,000
08/28/25
4
2.5
3,257
40 Chestnut St, Wellesley, MA
0.25
Single-Family Home
$2,450,000
05/06/26
5
3.5
3,369
4 Arnold Rd, Wellesley, MA
0.41
Single-Family Home
$1,750,000
09/23/25
4
2.5
3,156
53 Abbott Rd, Wellesley, MA
0.45
Single-Family Home
$2,300,000
09/03/25
3
2.5
4,158
12 Cypress Rd, Wellesley, MA
0.32
Single-Family Home
$2,610,000
06/02/25
5
3.5
3,390

Nearby homes

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Assigned Schools

These are the assigned schools for 14 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 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"
    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
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  • Emilyperrottet
    "I take the Commuter rail from Wellesley to the T subway. 1.5 hours to Cambridge from south station. "
    0
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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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14 Cliff Rd, Wellesley, MA 02481 is a 4 bedroom, 4 bathroom, 3,233 sqft single-family home built in 1921. This property is not currently available for sale. 14 Cliff Rd was last sold on Mar 30, 2023 for $2,500,000. The current Trulia Estimate for 14 Cliff Rd is $2,673,200.