14 Cliff Rd, Wellesley, MA 02481
Property image
Property image
OFF MARKET

$2,962,100

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

14 Cliff Rd, Wellesley, MA 02481

Refinance Your Home
Currently Off Market - Sold Mar 30, 2023 for $2,500,000

Home Value

Trulia Estimate
$2.96M
Since last month
Increased$201K (+7.2%)
Since last year
Increased$309K (+11.6%)
Since last sale
Increased$473K (+18.9%)
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 +81% in the last 10 years
MonthEstimated value
2026
August 2026$2.97M
July 2026$2.77M
June 2026$2.71M
May 2026$2.69M
March 2026$2.67M
February 2026$2.7M
January 2026$2.67M
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
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
7 Garden Rd, Wellesley, MA
0.10
Single-Family Home
$2,059,981
09/25/25
5
3.5
4,643
44 Bradford Rd, Wellesley, MA
0.20
Single-Family Home
$3,100,000
06/02/26
5
5.5
4,785
26 Edmunds Rd, Wellesley, MA
0.29
Single-Family Home
$3,115,000
01/09/26
4
3.5
4,294
35 Arnold Rd, Wellesley, MA
0.35
Single-Family Home
$2,525,000
06/26/26
4
3.5
3,497
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

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
3 Garden Rd, Wellesley, MA 02481
0.05
$2,500,000
4
3.5
4,870
Recently Sold
5 Cliff Rd, Wellesley, MA 02481
0.06
$3,295,300
5
4.5
5,210
Off Market
7 Cliff Rd, Wellesley, MA 02481
0.08
$1,865,000
5
3.5
3,774
Recently Sold
500 Worcester St, Wellesley, MA 02481
0.13
$1,381,500
4
2.5
3,257
Off Market
36 Kimlo Rd, Wellesley, MA 02481
0.14
$1,130,000
3
2
1,431
Recently Sold
34 Bradford Rd, Wellesley, MA 02481
0.16
$2,740,700
5
3.5
3,954
Off Market
26 Kimlo Rd, Wellesley, MA 02481
0.16
$1,065,800
3
2
1,505
Recently Sold
40 Kimlo Rd, Wellesley, MA 02481
0.16
$1,925,000
4
2.5
2,896
For Sale
32 Rockland St, Wellesley, MA 02481
0.17
$748,200
3
1.5
1,798
Off Market
37 Garden Rd, Wellesley, MA 02481
0.21
$3,208,400
6
4.5
4,297
Off Market
44 Bradford Rd, Wellesley, MA 02481
0.20
$3,100,000
5
5.5
4,785
Recently Sold
22 Kimlo Rd, Wellesley, MA 02481
0.19
$857,600
3
2
1,466
Off Market

Local Information

  • Map ViewExplore the area around 14 Cliff Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1921
Lot Size
1.02 acres
Living Area
3,233 sqft
Price/Sqft
$916
Parking
Garage

About this House

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.
14 Cliff Rd, Wellesley, MA 02481 is a 4 bedroom, 4 bathroom, 3,233 sqft single-family home built in 1921. It last sold for $2,500,000 on Mar 30, 2023. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,962,100, with a rent estimate of $7,494/month.

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, 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 and Tax history

DateEventPrice
Mar 30, 2023
Source: N/A
Sold
$2,500,000
Dec 1, 2016
Source: N/A
Sold
$1,554,375
Sep 21, 2016
Source: Agent Provided
Listed For Sale
$1,645,000
Jan 18, 2005
Source: N/A
Sold
$1,325,000

Market trends in Wellesley

Last updated July 2026
Buyer'sMarketSeller'sMarket
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

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.
  • 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
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 14 Cliff Rd

  • What is 14 Cliff Rd estimated to be worth?
    Trulia's estimated value for 14 Cliff Rd in Wellesley, MA is $2,962,100.
  • What is the price history for 14 Cliff Rd?
    14 Cliff Rd in Wellesley, MA last sold for $2,500,000 in March 2023.
  • Is Wellesley a buyer's or seller's market?
    Wellesley is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Wellesley?
    The median sale price in Wellesley is $2.15M. That is up $161K from the prior month.
  • Does 14 Cliff Rd have air conditioning?
    Yes, 14 Cliff Rd in Wellesley, MA has air conditioning.
  • Does 14 Cliff Rd have laundry facilities?
    Yes, 14 Cliff Rd in Wellesley, MA has in-unit laundry.

Explore by feature - Pet Friendly

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Off Market Homes Near 14 Cliff Rd

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