165 Cliff Rd
Wellesley, MA 02481
6 Beds
6.5 Baths
11,041 sqft (on 0.90 acres)
6 Beds
6.5 Baths
11,041 sqft
(on 0.90 acres)
Local Information
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Description
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!
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. This description is from January 16, 2025
Home Highlights
Parking
Garage
Outdoor
Patio
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
180+ days ago
Home Details for 165 Cliff Rd
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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 |
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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 |
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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 |
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Price List Price: $5,400,000 |
Status Change & Dates Off Market Date: Sun Dec 01 2024 |
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MLS Status: Sold |
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Direction & Address City: Wellesley |
School Information Elementary School: SpragueJr High / Middle School: WmsHigh School: Whs |
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Building Area Building Area: 11041 Square Feet |
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Community Features: Public Transportation, Conservation AreaNot Senior Community |
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No HOA |
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Lot Area: 0.90 acres |
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Listing Terms: Contract |
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BasementMls Number: 73297001 |
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Public TransportationConservation Area |
Last check for updates: about 8 hours 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
Price History for 165 Cliff Rd
| Date | Price | Event | Source |
|---|---|---|---|
| 01/15/2025 | $5,150,000 | Sold | MLS PIN #73297001 |
| 10/18/2024 | $5,400,000 | PriceChange | MLS PIN #73297001 |
| 10/01/2024 | $5,600,000 | Listed For Sale | MLS PIN #73297001 |
| 01/28/2020 | $3,600,000 | Sold | N/A |
| 12/06/2019 | $3,975,000 | Pending | Agent Provided |
| 11/27/2019 | $3,975,000 | PendingToActive | Agent Provided |
| 11/21/2019 | $3,975,000 | Pending | Agent Provided |
| 11/03/2019 | $3,975,000 | PriceChange | Agent Provided |
| 08/18/2019 | $4,150,000 | PriceChange | Agent Provided |
| 06/23/2019 | $4,475,000 | PriceChange | Agent Provided |
| 04/10/2019 | $4,850,000 | Listed For Sale | Agent Provided |
| 03/14/2014 | $3,100,000 | Sold | N/A |
| 09/09/2013 | $3,595,000 | PriceChange | Agent Provided |
| 01/15/2013 | $3,995,000 | Listed For Sale | Agent Provided |
| 06/09/2012 | $4,650,000 | ListingRemoved | Agent Provided |
| 06/01/2012 | $4,650,000 | Listed For Sale | Agent Provided |
| 11/28/2011 | $4,650,000 | ListingRemoved | Agent Provided |
| 11/12/2010 | $4,650,000 | Listed For Sale | Agent Provided |
| 06/30/1999 | $249,750 | Sold | N/A |
Market trends in Wellesley
Last updated April 2026
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
108 6MoM
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Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $49,879 |
| Assessment | $4,852,000 |
Home facts updated by county records
Comparable Sales for 165 Cliff Rd
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.23 | Single-Family Home | $4,558,000 | 10/14/25 | 5 | 5 | 6,160 | |
0.11 | Single-Family Home | $4,400,000 | 12/01/25 | 6 | 8 | 7,000 | |
0.20 | Single-Family Home | $4,750,000 | 05/11/26 | 5 | 7 | 7,720 | |
0.37 | Single-Family Home | $5,600,000 | 08/04/25 | 6 | 5.5 | 7,391 | |
0.31 | Single-Family Home | $5,100,000 | 06/24/25 | 4 | 6 | 7,408 | |
0.42 | Single-Family Home | $5,097,250 | 05/15/26 | 6 | 6 | 8,100 | |
0.50 | Single-Family Home | $5,000,000 | 05/18/26 | 7 | 9 | 9,116 | |
0.28 | Single-Family Home | $3,475,000 | 07/31/25 | 5 | 5.5 | 5,359 | |
0.48 | Single-Family Home | $6,200,000 | 08/22/25 | 6 | 6.5 | 7,569 | |
0.11 | Single-Family Home | $14,750,000 | 09/30/25 | 6 | 7 | 14,663 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.
SOLDSEP 30, 2025Melissa Dailey, Coldwell Banker Realty - Wellesley
OFF MARKETChristine Lawrence, Rutledge Properties
SOLDDEC 1, 2025Debi Benoit, William Raveis R.E. & Home Services
FOR SALE0.75 ACRESBeyond Boston Properties Group, Compass
FOR SALE0.97 ACRESDonahue Maley and Burns Team, Compass
OFF MARKETDonahue Maley and Burns Team, Compass- OFF MARKETMelissa Dailey, Coldwell Banker Realty - Wellesley
OFF MARKETJill Finkelstein & Associates, Compass
SOLDOCT 15, 2025The Lara & Chelsea Collaborative, Coldwell Banker Realty - Wellesley
OFF MARKETDonahue Maley and Burns Team, Compass
Assigned Schools
These are the assigned schools for 165 Cliff Rd.
- Sprague Elementary School
- K-5
- Public
- 276 Students
9/10GreatSchools RatingParent Rating AverageWe love Sprague school! We have had 3 children in the school and love the atmosphere, teachers, and new principal. Updated building and playgrounds, with beautiful fields adjacent. The parents are WONDERFUL.Parent Review5y ago - Wellesley Middle School
- 6-8
- Public
- 910 Students
8/10GreatSchools RatingParent Rating AverageAfter an amazing experience at Wellesley public schools for elementary school, I entered middle school optimistic and excited. However, I was incredibly disappointed to find that Wellesley Middle School did not at all live up to my expectations. Most teachers seemed disinterested in their work and in teaching students. Little effort was given to support students who had difficulty learning material. Administrators were harsh and unkind to students. Students experiencing discrimination or bullying received next to no help from the school. The unfortunate reality is that Wellesley Middle School is a three year hell, and many other students and parents I have spoken to agree.Other Review1y ago - Wellesley High School
- 9-12
- Public
- 1231 Students
10/10GreatSchools RatingParent Rating AverageThis High School is excellent in that the teaching staff is top notch. There are so many courses to choose from and the individual departments and teacher encourage student to challenge themselves, stretch themselves and not limit them to mid-level course offerings. There seems to be a lot of communication between families, teachers and administration. The communication is open and the atmosphere is positive. Our kids all got great educations and had their choice of top tier colleges. The principal is very open to talking with parents and makes sure that the faculty adopts a similar open policy. I feel like they are concerned with your child and work with the student to achieve success.Parent Review12y ago 
Check out schools near 165 Cliff Rd.
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.
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Homes for sale near 165 Cliff Rd
- 0.97 ACRESDonahue Maley and Burns Team, Compass
- 0.75 ACRESBeyond Boston Properties Group, Compass
1.13 ACRESDonahue Maley and Burns Team, Compass
0.97 ACRESMelissa Dailey, Coldwell Banker Realty - Wellesley
OFF MARKETThe Lara & Chelsea Collaborative, Coldwell Banker Realty - Wellesley
NEW - 18 HRS AGO0.89 ACRESJake Farrell, Keller Williams Realty
0.59 ACRESRachel Lieberman, Berkshire Hathaway HomeServices Commonwealth Real Estate
See more homes for sale inWellesley
Off Market Homes Near 165 Cliff Rd
SOLDJUN 5, 2026Stephanie Lau, Bellafi Real Estate, Inc.
SOLDJUN 5, 2026The Lara & Chelsea Collaborative, Coldwell Banker Realty - Wellesley
SOLDJUN 5, 2026Petrone-Hunter Realty Group, Coldwell Banker Realty - Wellesley
SOLDJUN 5, 2026Mizner + Montero, Gibson Sotheby's International Realty
SOLDJUN 5, 2026Tish Kennedy Dolan, Louise Condon Realty
SOLDJUN 5, 2026Mary Dunlavey, Brewster & Berkowitz R. E.
SOLDJUN 5, 2026Judith Brady, Berkshire Hathaway HomeServices Commonwealth Real Estate
SOLDJUN 5, 2026Ed Lyon, Preservation Properties
SOLDJUN 5, 2026The Shulkin Wilk Group, Compass
SOLDJUN 5, 2026Renu Shukla, Engel & Volkers Wellesley- See more homes for sale inWellesley
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.
The MLS listing information displayed is deemed reliable, but is not guaranteed accurate by the MLS.
Homes for rent near 165 Cliff Rd
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165 Cliff Rd, Wellesley, MA 02481 is a 6 bedroom, 8 bathroom, 11,041 sqft single-family home built in 1930. This property is not currently available for sale. 165 Cliff Rd was last sold on Jan 15, 2025 for $5,150,000 (5% lower than the asking price of $5,400,000).