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

$5,874,900

Trulia Estimate
  • 6 Beds
  • 6.5 Baths
  • 11,041 sqft (on 0.90 acres)

165 Cliff Rd, Wellesley, MA 02481

Est. Refi. Payment $34,868/mo*
Refinance Your Home
Currently Off Market - Sold Jan 15, 2025 for $5,150,000

Home Value

Trulia Estimate
$5.88M
Since last month
Increased$386K (+7%)
Since last year
Increased$647K (+12.4%)
Since last sale
Increased$725K (+14.1%)
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 +69% in the last 10 years
MonthEstimated value
2026
August 2026$5.87M
August 2026$5.83M
July 2026$5.49M
June 2026$5.32M
May 2026$5.27M
April 2026$5.28M
March 2026$5.24M
February 2026$5.29M
January 2026$5.23M
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
65 Woodcliff Rd, Wellesley, MA
0.18
Single-Family Home
$4,593,250
08/10/26
7
6.5
8,840
14 Greylock Rd, Wellesley, MA
0.30
Single-Family Home
$6,100,000
07/22/26
6
7.5
10,197
26 White Oak Rd, Wellesley, MA
0.23
Single-Family Home
$4,558,000
10/14/25
5
5
6,160
56 Ledgeways, Wellesley, MA
0.11
Single-Family Home
$4,400,000
12/01/25
6
8
7,000
3 Ravine Rd, Wellesley, MA
0.20
Single-Family Home
$4,750,000
05/11/26
5
7
7,720
64 Albion Rd, Wellesley, MA
0.32
Single-Family Home
$5,500,000
07/24/26
5
5
6,203
99 Old Colony Rd, Wellesley, MA
0.42
Single-Family Home
$5,097,250
05/15/26
6
6
8,100
52 Valley Rd, Wellesley, MA
0.37
Single-Family Home
$9,275,000
07/07/26
7
8
11,124
8 Glen Brook Rd, Wellesley, MA
0.40
Single-Family Home
$4,620,000
07/08/26
6
6.5
7,606
43 Bristol Rd, Wellesley, MA
0.50
Single-Family Home
$5,000,000
05/18/26
7
9
9,116

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
184 Cliff Rd, Wellesley, MA 02481
0.11
$15,367,400
6
7
14,663
Off Market
73 Ledgeways, Wellesley, MA 02481
0.12
$3,631,100
6
5.5
5,154
Off Market
56 Ledgeways, Wellesley, MA 02481
0.11
$4,400,000
6
8
7,000
Recently Sold
35 Albion Rd, Wellesley, MA 02481
0.18
$2,800,000
-
-
-
Recently Sold
65 Woodcliff Rd, Wellesley, MA 02481
0.18
$4,593,250
7
6.5
8,840
Recently Sold
45 White Oak Rd, Wellesley, MA 02481
0.15
$10,995,000
5
5.5
7,200
For Sale
200 Cliff Rd, Wellesley, MA 02481
0.19
$5,100,000
7
6
7,262
For Sale
56 Woodcliff Rd, Wellesley, MA 02481
0.22
$3,151,500
5
3.5
4,534
Off Market
56 White Oak Rd, Wellesley, MA 02481
0.16
$3,989,200
5
4.5
4,309
Off Market
29 Woodcliff Rd, Wellesley, MA 02481
0.23
$3,974,700
4
4.5
4,665
Off Market
70 Old Farm Rd, Wellesley, MA 02481
0.18
$2,963,100
2
2
3,736
Off Market

Local Information

  • Map ViewExplore the area around 165 Cliff Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1930
0.9 acre lot
11,041 sqft
$532/sqft
Garage

About this House

This captivating Tudor blends timeless elegance w/modern sophistication redesigned by the renowned architect, Patrick Ahern. It's situated on nearly an acre of lush, pristine grounds in the prestigious Cliff Estates. The magnificent Carriage House w/a vaulted ceiling studio & bath offers the perfect work from home setting. A residence w/impressive sunlit formal rooms, handsome library w/a fireplace & inviting sunroom. The gorgeous Chef's Kitchen w/adjacent butler's pantry flows seamlessly into the Family Room. Double French doors opens to stone patios & fenced in play yard for fun & entertaining. 2nd floor w/4 en suite bdrms, including a luxurious Primary suite w/a spa-like bath & 3 closets. 3rd fl is dedicated to the ideal guest suite w/2 bedrooms, sitting room & bath. The LL is a true haven for leisure, w/it's spacious playroom, wine cellar, exercise room & billiard room w/ French doors leading to a blue stone patio. A special home, long admired & the one you've been waiting for!
165 Cliff Rd, Wellesley, MA 02481 is a 6 bedroom, 8 bathroom, 11,041 sqft single-family home built in 1930. It last sold for $5,150,000 on Jan 15, 2025 (5% below the $5,400,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $5,874,900.
Last check for updates: 36 minutes ago
Listed by Patricia Bradley, (781) 910-1238
Rutledge Properties, (781) 235-4663
Bought with: Susan Bevilacqua, (781) 589-8257, Douglas Elliman Real Estate - Wellesley, (781) 472-1099
Source: MLS PIN, MLS#73297001

Home Details for 165 Cliff Rd

Interior Features

Interior Details
Basement: Finished,Walk-Out Access,Sump Pump,Radon Remediation SystemNumber of Rooms: 19Types of Rooms: Master Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Bedroom 5, Master Bathroom, Bathroom 1, Bathroom 2, Bathroom 3, Dining Room, Family Room, Kitchen, Living Room, OfficeWet Bar
Beds & Baths
Number of Bedrooms: 6Number of Bathrooms: 8Number of Bathrooms (full): 5Number of Bathrooms (half): 3
Dimensions and Layout
Living Area: 11041 Square Feet
Appliances & Utilities
Utilities: for Gas RangeAppliances: Range, Dishwasher, Disposal, Microwave, Refrigerator, Washer, Dryer, Wine Refrigerator, Range Hood, Wine CoolerDishwasherDisposalDryerLaundry: Stone/Granite/Solid Countertops,In BasementMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Forced Air,Radiant,Natural Gas,FireplaceHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air
Fireplace & Spa
Number of Fireplaces: 4Fireplace: Living Room, Master BedroomHas a FireplaceNo Spa
Gas & Electric
Electric: Circuit Breakers
Windows, Doors, Floors & Walls
Window: ScreensDoor: French DoorsFlooring: Flooring - Hardwood, Flooring - Stone/Ceramic Tile, Flooring - Wall to Wall Carpet
Levels, Entrance, & Accessibility
Accessibility: NoFloors: Flooring Hardwood, Flooring Stone Ceramic Tile, Flooring Wall To Wall Carpet
Security
Security: Security System

Exterior Features

Exterior Home Features
Roof: SlatePatio / Porch: PatioFencing: FencedExterior: Patio, Rain Gutters, Professional Landscaping, Sprinkler System, Decorative Lighting, Screens, Fenced Yard, Fruit Trees, Stone WallFoundation: Concrete PerimeterSprinkler System
Parking & Garage
Number of Garage Spaces: 3Number of Covered Spaces: 3Open Parking Spaces: 10No CarportHas a GarageNo Attached GarageHas Open ParkingParking Spaces: 13Parking: Detached,Garage Door Opener,Heated Garage,Oversized,Paved Drive,Off Street,Driveway,Paved
Frontage
Road Frontage: PublicNot on Waterfront
Water & Sewer
Sewer: Public Sewer

Property Information

Year Built
Year Built: 1930
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Tudor
Building
Not Attached PropertyDoes Not Include Home Warranty
Property Information
Parcel Number: M:094 R:052 S:, 260316

Price & Status

Price
List Price: $5,400,000
Status Change & Dates
Off Market Date: Sun Dec 01 2024

Active Status

MLS Status: Sold

Location

Direction & Address
City: Wellesley
School Information
Elementary School: SpragueJr High / Middle School: WmsHigh School: Whs

Building

Building Area
Building Area: 11041 Square Feet

Community

Community Features: Public Transportation, Conservation AreaNot Senior Community

HOA

No HOA

Lot Information

Lot Area: 0.90 acres

Offer

Listing Terms: Contract

Miscellaneous

BasementMls Number: 73297001

Additional Information

Public TransportationConservation Area

Price and Tax history

DateEventPrice
Jan 15, 2025
Source: MLS PIN #73297001
Sold
$5,150,000
Oct 18, 2024
Source: MLS PIN #73297001
PriceChange
$5,400,000
Price decreased by 4%
Oct 1, 2024
Source: MLS PIN #73297001
Listed For Sale
$5,600,000
Jan 28, 2020
Source: N/A
Sold
$3,600,000
Dec 6, 2019
Source: Agent Provided
Pending
$3,975,000

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
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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
    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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LGBTQ Local Legal Protections

The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information are for the personal, non commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein.
The MLS listing information displayed is deemed reliable, but is not guaranteed accurate by the MLS.

Frequently asked questions about 165 Cliff Rd

  • What is 165 Cliff Rd estimated to be worth?
    Trulia's estimated value for 165 Cliff Rd in Wellesley, MA is $5,874,900.
  • What is the price history for 165 Cliff Rd?
    165 Cliff Rd in Wellesley, MA last sold for $5,150,000 in January 2025.
  • 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 165 Cliff Rd have air conditioning?
    Yes, 165 Cliff Rd in Wellesley, MA has air conditioning.
  • Does 165 Cliff Rd have laundry facilities?
    Yes, 165 Cliff Rd in Wellesley, MA has in-unit laundry.

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Off Market Homes Near 165 Cliff Rd

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