0.24 mi
Distance
Prestigious Cliff Estates residence is generously sited on just under an acre of land. This chic and sophisticated home, completely renovated in 2015, offers exquisite and timeless architectural detail throughout. Stunning foyer leads to grand living room with gorgeous beamed ceiling and classic dining room with lovely butler's pantry. Stunning chef's kitchen with high end appliances, custom hood and oversized island opens to sun-filled eat-in area and magnificent family room overlooking manicured grounds. Second floor offers luxurious master suite with serene spa like bath, three well proportioned bedrooms and two beautifully renovated full baths. Special space on the third floor with quiet sitting room and two bedrooms is the perfect spot to get away. Lower level includes exercise space, handsome billiard room, elegant wine cellar and gracious playroom. Fabulous carriage house with art studio and full bath offers a private retreat. Nothing has been spared - a truly amazing property
Cliff Road
Source: School Digger
Preschool At Wellesley Schools
Public • PK - PK • Serves this home
Distance
Public • 6 - 8 • Serves this home
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Public • 9 - 12 • Serves this home
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Preschool At Wellesley Schools
Public • PK - PK • Serves this home
Distance
Public • PK - 3
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Public • PK - 3
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Public • PK - 5
Distance
William F. Stanley Elementary School
Public • PK - 5
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Public • PK - PK
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Public • PK - PK
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Public • PK - 5
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Public • PK - KG
Distance
Public • 6 - 8 • Serves this home
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Public • 6 - 8
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Public • 4 - 5
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Public • 6 - 8
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Public • 5 - 8
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Public • 7 - 8
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Public • 6 - 6
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Public • 6 - 8
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Public • 6 - 8
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Public • 6 - 8
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Public • 9 - 12 • Serves this home
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Public • 9 - 12
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Public • 9 - 12
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Public • 9 - 12
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Public • 9 - 12
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Public • 9 - 12
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Public • 9 - 12
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Private • 06 - 12
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Private • 05 - 12
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Private • 08 - 12
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Private • UG - UG
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Brandon School & Residental Treatment
Private • 02 - 12
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Private • 03 - 12
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Private • UG - UG
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Private • 08 - 11
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Walnut Hill School For The Arts
Private • 09 - 12
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Bais Yaakov Of Boston High School
Private • 09 - 12
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Source: Public Records
| Street Address | Beds | Baths | Sold Date | List Price | Valuation Date | Valuation Price |
|---|---|---|---|---|---|---|
| 58 Norwich Road | Listing | 4 | 4 | Jan 16, 2026 | $2,249,000 | Mar 21, 2024 | $2,012,445 |
| 26 Winter Street | Listing | 4 | 3 | Dec 22, 2025 | $1,088,000 | Feb 23, 2024 | $1,027,081 |
| 51 Radcliffe Road | Listing | 6 | 9 | Nov 24, 2025 | $5,199,000 | Mar 21, 2024 | $1,795,680 |
| 5 Walnut Road | 6 | 7 | Dec 02, 2025 | $6,195,000 | Jan 24, 2026 | - |
| 36 Oakridge Rd | 6 | 7 | Dec 06, 2025 | $4,999,000 | Jan 24, 2026 | - |
| 21 Chestnut Street | 7 | 11 | Dec 04, 2025 | $12,895,000 | Jan 24, 2026 | - |
| 217 Summer St | - | 0 | Jan 10, 2026 | $1,499,000 | Jan 24, 2026 | - |
| 48 Shady Hill Road | 4 | 5 | Dec 10, 2025 | $1,595,000 | Jan 24, 2026 | - |
| 45 Mayo Rd | 3 | 2 | Jan 11, 2026 | $1,300,000 | Jan 24, 2026 | - |
| 18 Patton Road | 6 | 7 | Dec 02, 2025 | $2,995,000 | Jan 24, 2026 | - |
Source: Sperling's Best Places
| Zip | City | County | National | |
|---|---|---|---|---|
| Population | N/A | 14,421 | 725,326 | 335,858,263 |
| Population Density | N/A | 2,879 | 1,831 | 95 |
| People per Household | N/A | 2.8 | 2.5 | 2.6 |
| Median Age | N/A | 33.9 | 43 | 39.1 |
| Median Income | N/A | $182,173 | $108,049 | $66,222 |
| Average Income | N/A | $96,489 | $57,162 | $35,475 |
| Cost of Living Index | 146 | 139 | 117 | 100 |
| Zip | City | County | National | |
|---|---|---|---|---|
| January Avg. High Temp | N/A°F | 17.29°F | 18.1°F | 22.6°F |
| July Avg. High Temp | N/A°F | 83.13°F | 81.2°F | 86.2°F |
| Annual Precipitation | N/A" | 45.45" | 51.22" | 38" |
9/100
Walk Score ®
23/100
Bike Score ®
The average walkability score in the surrounding area is Walk Score: 25/100, Transit Score: 7/100, Bike Score: 29/100.
0.24 mi
Distance
0.3 mi
Distance
Recreation
0.48 mi
Distance
0.53 mi
Distance
0.55 mi
Distance
0.56 mi
Distance
0.57 mi
Distance
0.24 mi
Distance
0.3 mi
Distance
0.57 mi
Distance
0.21 mi
Distance
0.26 mi
Distance
0.27 mi
Distance
0.28 mi
Distance
0.28 mi
Distance
0.29 mi
Distance
0.31 mi
Distance
0.43 mi
Distance
0.47 mi
Distance
0.54 mi
Distance
0.58 mi
Distance
0.6 mi
Distance
0.61 mi
Distance
6 bds • 6 ba • 6,406 sqft
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5 bds • 6 ba • 6,378 sqft
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5 bds • 5 ba • 6,255 sqft
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6 bds • 7 ba • 7,867 sqft
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6 bds • 7 ba • 7,885 sqft
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7 bds • 8 ba • 8,107 sqft
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5 bds • 8 ba • 6,700 sqft
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6 bds • 8 ba • 7,185 sqft
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6 bds • 6 ba • 6,281 sqft
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8 bds • 10 ba • 6,228 sqft
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5 bds • 7 ba • 7,523 sqft
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7 bds • 9 ba • 8,056 sqft
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7 bds • 9 ba • 8,056 sqft
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6 bds • 6 ba • 6,400 sqft
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7 bds • 8 ba • 7,236 sqft
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6 bds • 7 ba • 6,300 sqft
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9 bds • 7 ba • 6,292 sqft
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6 bds • 6 ba • 6406 sqft
84 Royalston Rd
6 bds • 6 ba • 5806 sqft
42 Edmunds Road
5 bds • 7 ba • 7461 sqft
39 Audubon Rd
6 bds • 6 ba • 7047 sqft
201 Lowell Road
6 bds • 7 ba • 7962 sqft
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5 bds • 6 ba • 5833 sqft
12 Bird Hill Ave
5 bds • 6 ba • 4886 sqft
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6 bds • 5 ba • 6990 sqft
151 Oakland Street
3 bds • 3 ba • 2310 sqft
148 Weston Rd 207
2 bds • 3 ba • 2270 sqft
148 Weston Rd 208
10 bds • 9 ba • 10318 sqft
5-7 Abbott Street
6 bds • 7 ba • 7658 sqft
83 Brown
5 bds • 6 ba • 5073 sqft
8 Oakdale Ave
6 bds • 7 ba • 6100 sqft
177 Varick Rd
6 bds • 6 ba • 5993 sqft
310 Oakland
7 bds • 8 ba • 6501 sqft
34 Pershing Rd
6 bds • 7 ba • 5830 sqft
3 Hancock Road
5 bds • 6 ba • 6378 sqft
873 Chestnut Street
6 bds • 8 ba • 7340 sqft
52 Hancock Street
5 bds • 5 ba • 6255 sqft
19 Gordon Road
Source: Realty.com
165 Cliff Rd, Wellesley, MA 02481 is a Single Family 7,143 sq. ft. home listed for sale. Realty.com has 29 photos available of this 6 bed, 8 bath house, listed at $3,975,000. View sales and tax history, use our mortgage calculator and more on Realty.com
Realty.com has 29 photos of 165 Cliff Rd.
Our records indicate that 165 Cliff Rd was built in 1929.
The full address for this home is 165 Cliff Rd, Wellesley, MA 02481.
165 Cliff Rd has been listed on Realty.com since Wed April 10, 2019
Almost all errands require a car. It is possible to get on a bus. Minimal bike infrastructure.
The average walkability score in the surrounding area is Walk Score: 25/100, Transit Score: 7/100, Bike Score: 29/100.
There are 3 schools assigned to this home. Check out the schools near 165 Cliff Rd. Preschool At Wellesley Schools (Grades: PK - PK), Wellesley Middle School (Grades: 6 - 8), Wellesley Senior High School (Grades: 9 - 12)
Listing provided courtesy of:
Gibson Sotheby's International Realty
(tel: 781-237-8181)
Listing agent:
Debi Benoit
(tel: 617-962-9292)
(#BB980372)
This content last refreshed on 2026-01-24 07:48:30. Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.
Export listing data of 165 Cliff Rd, Wellesley, MA 02481 : MLS# 72479607