20 Cliff Rd, Wellesley, MA 02481
OFF MARKET

20 Cliff Rd
Wellesley, MA 02481

  • 3 Beds
  • 2 Baths
  • 2,532 sqft (on 0.46 acres)

$1,634,900

Trulia Estimate
as of Aug 20, 2026
Est. Refi. Payment $9,741/mo*
Refinance Your Home

$1,634,900

Trulia Estimate
as of Aug 20, 2026
Est. Refi. Payment $9,741/mo*
Refinance Your Home
3 Beds
2 Baths
2,532 sqft
(on 0.46 acres)

Home Value

Trulia Estimate
$1.64M
Since last month
Decreased$29K (-1.8%)
Since last year
Increased$36K (+2.3%)
Since last sale
Increased$455K (+38.5%)
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 +49% in the last 10 years
MonthEstimated value
2026
August 2026$1.63M
July 2026$1.66M
June 2026$1.69M
May 2026$1.7M
April 2026$1.67M
March 2026$1.68M
February 2026$1.6M
January 2026$1.55M
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
6 Wareland Rd, Wellesley, MA
0.38
Single-Family Home
$1,282,000
07/15/26
3
2
2,122
36 Kimlo Rd, Wellesley, MA
0.17
Single-Family Home
$1,130,000
08/14/26
3
2
1,431
26 Kimlo Rd, Wellesley, MA
0.18
Single-Family Home
$1,065,800
12/02/25
3
2
1,505
500 Worcester St, Wellesley, MA
0.16
Single-Family Home
$1,340,000
08/28/25
4
2.5
3,257
22 Kimlo Rd, Wellesley, MA
0.22
Single-Family Home
$830,000
10/01/25
3
2
1,466
12 Wareland Rd, Wellesley, MA
0.39
Single-Family Home
$1,250,000
06/16/26
3
3
1,808
4 Southwick Cir, Wellesley, MA
0.33
Single-Family Home
$1,690,000
11/20/25
3
1.5
2,014
3 Garden Rd, Wellesley, MA
0.04
Single-Family Home
$2,500,000
03/05/26
4
3.5
4,870
15 Clifton Rd, Wellesley, MA
0.32
Single-Family Home
$1,635,650
04/16/26
4
2.5
2,112
7 Garden Rd, Wellesley, MA
0.09
Single-Family Home
$2,059,981
09/25/25
5
3.5
4,643

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
0.04
$2,500,000
4
3.5
4,870
Recently Sold
5 Cliff Rd, Wellesley, MA 02481
0.07
$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
7 Garden Rd, Wellesley, MA 02481
0.09
$1,799,999
5
3.5
4,643
Foreclosure
500 Worcester St, Wellesley, MA 02481
0.16
$1,386,500
4
2.5
3,257
Off Market
36 Kimlo Rd, Wellesley, MA 02481
0.17
$1,130,000
3
2
1,431
Recently Sold
34 Bradford Rd, Wellesley, MA 02481
0.16
$2,733,500
5
3.5
3,954
Off Market
26 Kimlo Rd, Wellesley, MA 02481
0.18
$1,065,800
3
2
1,505
Recently Sold
40 Kimlo Rd, Wellesley, MA 02481
0.18
$1,925,000
4
2.5
2,896
For Sale
32 Rockland St, Wellesley, MA 02481
0.19
$749,300
3
1.5
1,798
Off Market
37 Garden Rd, Wellesley, MA 02481
0.19
$3,219,000
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

Local Information

  • Map ViewExplore the area around 20 Cliff Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1954
Lot Size
0.46 acres
Living Area
2,532 sqft
Price/Sqft
$646
Parking
Garage

About this House

Location, Location, Location. Sited on .46 acres in the heart of Wellesley Hills, this gracious 7 room home is a stone's throw from the Wellesley Hills commuter rail station, Café Nero and bakeries, restaurants, the Brook Path, and town parks. 5 minutes to the Mass Pike. Open and airy with a vaulted, granite and stainless kitchen flowing seamlessly to a large eating area, glass doors to a brick patio, and family room that overlooks secluded property from a private mahogany deck. Three well-proportioned bedrooms and two updated bathrooms, including Master, make for easy one floor living. Lower level is finished for playroom, teen suite, and/or home office. Home has a permit for second curb cut for easy one level access. 20 Cliff is an elegant home in an irreplaceable location.
20 Cliff Rd, Wellesley, MA 02481 is a 3 bedroom, 2 bathroom, 2,532 sqft single-family home built in 1954. It last sold for $1,180,000 on Oct 20, 2020. It is currently off market. The Trulia Estimate is $1,634,900, with a rent estimate of $4,891/month.

Home Details for 20 Cliff Rd

Interior Features

Interior Details
BasementAtticNumber of Rooms: 7Types of Rooms: Dining Room, Family Room, Master Bath, Recreation Room
Heating & Cooling
Heating: Forced Air, Heat Pump, GasAir ConditioningCooling System: Central, WallHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 1Floors: Hardwood
Appliances & Utilities
Cable ReadyDishwasherDisposalDryerRefrigeratorWasher
Fireplace & Spa
Fireplace
Windows, Doors, Floors & Walls
Double Paned Windows
Security
Security System

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: WoodLawnSprinkler System
Parking & Garage
GarageParking Spaces: 6Parking: Garage Attached, Off Street

Property Information

Year Built
Year Built: 1954Year Updated: 1975
Property Type / Style
Property Type: Single Family HomeArchitecture: Ranch / Rambler

Community

Units in Building: 1

Lot Information

Lot Area: 0.46 acres

Price and Tax history

DateEventPrice
Oct 20, 2020
Source: N/A
Sold
$1,180,000
Jul 21, 2020
Source: Agent Provided
ListingRemoved
$1,220,000
Jul 8, 2020
Source: Agent Provided
Listed For Sale
$1,220,000
Jun 21, 2007
Source: N/A
Sold
$840,000

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 20 Cliff Rd

  • What is 20 Cliff Rd estimated to be worth?
    Trulia's estimated value for 20 Cliff Rd in Wellesley, MA is $1,634,900.
  • What is the price history for 20 Cliff Rd?
    20 Cliff Rd in Wellesley, MA last sold for $1,180,000 in October 2020.
  • 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 20 Cliff Rd have air conditioning?
    Yes, 20 Cliff Rd in Wellesley, MA has air conditioning.
  • Does 20 Cliff Rd have laundry facilities?
    Yes, 20 Cliff Rd in Wellesley, MA has in-unit laundry.

Explore by feature - Pet Friendly

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Off Market Homes Near 20 Cliff Rd

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