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Cliff Estates Homes

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  • /24

    $5,294,500

    • 6 Beds
    • 7 Baths
    • 8,100 Sq Ft

    99 Old Colony Rd, Wellesley Hills, MA 02481

    Exceptional craftsmanship in this custom-built home by a premier high-end builder, located in the sought-after Cliff Estates. This stunning 6-bedroom, 5 full bath, offers an expansive open floor plan. The main level features 10 ft. ceilings with a sophisticated living room, formal dining room, spacious family room along with a beautifully appointed private office. At the heart of the home is a

    Elizabeth Derenzo J. Derenzo & Associates, LLC

    99 Old Colony Rd, Wellesley Hills, MA 02481
  • /34

    $5,800,000 Sold Dec 11, 2025

    7 Mountview Rd, Wellesley Hills, MA 02481

    • 6 Beds
    • 7 Baths
    • 7,400 Sq Ft
    • Built 2025

    Last Sold Summary

    • 11% Below List Price
    • $784/SF
    • 60 Days On Market

    Current Estimated Value $5,684,328

    Last Listing Agent Christine Lawrence Rutledge Properties

    7 Mountview Rd, Wellesley Hills, MA 02481
    • /31

      Est $2,113,985 Not Listed For Sale

      104 Westgate Rd, Wellesley Hills, MA 02481

      • 4 Beds
      • 2.5 Baths
      • 2,725 Sq Ft
      • Built 1960
      104 Westgate Rd, Wellesley Hills, MA 02481

      Last Sold Summary

      • 8% Above List Price
      • $716/SF
      • 1 Day On Market

      Last Sold Price $1,950,000

      Last Listing Agent The Shulkin Wilk Group Compass

  • /25

    $3,795,000 Pending

    • 5 Beds
    • 6 Baths
    • 6,550 Sq Ft

    138 Lowell Rd, Wellesley Hills, MA 02481

    Set in the heart of the coveted Cliff Estates sits this stunning young Colonial. Tall ceilings and a beautifully flowing floor plan define the home’s elegant yet comfortable atmosphere. At the center is a spacious eat-in kitchen with stainless appliances and granite counters for work space. It opens seamlessly into a grand family room anchored by a fireplace and sliders to the outdoor patio.

    Teri Adler MGS Group Real Estate LTD - Wellesley

    138 Lowell Rd, Wellesley Hills, MA 02481
  • /30

    $2,015,000 Sold Jul 31, 2025

    234 Lowell Rd, Wellesley Hills, MA 02481

    • 4 Beds
    • 3 Baths
    • 3,054 Sq Ft
    • Built 1956

    Last Sold Summary

    • 16% Below List Price
    • $660/SF
    • 29 Days On Market

    Current Estimated Value $2,032,517

    Last Listing Agent Berkowitz Team Keller Williams Boston MetroWest

    234 Lowell Rd, Wellesley Hills, MA 02481
    • /29

      Est $3,137,358 Not Listed For Sale

      209 Bristol Rd, Wellesley Hills, MA 02481

      • 4 Beds
      • 4 Baths
      • 2,866 Sq Ft
      • Built 1962
      209 Bristol Rd, Wellesley Hills, MA 02481

      Last Sold Summary

      • 74% Above List Price
      • $628/SF
      • 260 Days On Market

      Last Sold Price $1,800,000

      Last Listing Agent Moira Lown Coldwell Banker Realty - Wellesley

  • /2

    $5,790,000 New Construction

    • 6 Beds
    • 7 Baths
    • 7,777 Sq Ft

    78 Suffolk Rd, Wellesley Hills, MA 02481

    Ready for the summer! This stately 6 bed colonial sits in the heart of Cliff Estates with a large flat lot. Spacious foyer opens to both a private office and living room. Butler pantry with wet bar leads to dining room with custom moldings. The entire back of home is a great open space for everyday living with south/west sun exposure. Family room with fireplace has picture windows and access to a

    Melissa Dailey Coldwell Banker Realty - Wellesley

    78 Suffolk Rd, Wellesley Hills, MA 02481
  • /29

    $1,365,000 Sold Oct 24, 2025

    1 Roberts Rd, Wellesley, MA 02481

    • 3 Beds
    • 3 Baths
    • 2,499 Sq Ft
    • Built 1929

    Last Sold Summary

    • 2% Below List Price
    • $546/SF
    • 8 Days On Market

    Current Estimated Value $1,380,270

    Last Listing Agent Allison David Poirier Coldwell Banker Realty - Wellesley

    1 Roberts Rd, Wellesley, MA 02481
    • /42

      Est $4,639,660 Not Listed For Sale

      241 Bristol Rd, Wellesley Hills, MA 02481

      • 5 Beds
      • 8 Baths
      • 6,558 Sq Ft
      • Built 2016
      241 Bristol Rd, Wellesley Hills, MA 02481

      Last Sold Summary

      • 8% Above List Price
      • $656/SF
      • 4 Days On Market

      Last Sold Price $4,300,000

      Last Listing Agent Migdol Moore Team Gibson Sotheby's International Realty

  • /42

    $3,950,000

    • 6 Beds
    • 5.5 Baths
    • 7,034 Sq Ft

    241 Lowell Rd, Wellesley Hills, MA 02481

    Exceptional Opportunity In Wellesley’s Highly Desirable Cliff Estates. Situated On A Large, Level Lot Offering Excellent Privacy, This Elegant Residence Provides Over 7,000 Sq Ft Of Beautifully Designed Living Space With 6 Bedrooms And 5.5 Bathrooms. Sun-Filled Interiors Feature High Ceilings, Oversized Windows, And Refined Finishes Throughout. A Grand Foyer Opens To Spacious Living Areas Ideal

    Alpha Group Compass

    241 Lowell Rd, Wellesley Hills, MA 02481
  • /32

    $4,250,000 Sold Mar 11, 2026

    39 Audubon Rd, Wellesley, MA 02481

    • 5 Beds
    • 6.5 Baths
    • 7,461 Sq Ft
    • Built 2024

    Last Sold Summary

    • 6% Below List Price
    • $570/SF
    • 131 Days On Market

    Last Listing Agent Patricia Bradley Rutledge Properties

    39 Audubon Rd, Wellesley, MA 02481
    • /25

      Est $2,409,711 Not Listed For Sale

      94 Suffolk Rd, Wellesley Hills, MA 02481

      • 4 Beds
      • 3.5 Baths
      • 3,227 Sq Ft
      • Built 1957
      94 Suffolk Rd, Wellesley Hills, MA 02481

      Last Sold Summary

      • 10% Above List Price
      • $682/SF
      • 2 Days On Market

      Last Sold Price $2,200,000

      Last Listing Agent Teri Adler MGS Group Real Estate LTD - Wellesley

  • /42

    $5,450,000 Pending

    • 7 Beds
    • 10 Baths
    • 9,116 Sq Ft

    43 Bristol Rd, Wellesley Hills, MA 02481

    Stately brick Colonial in sought-after Cliff Estates sits on a magnificent private corner lot. A dramatic two-story foyer welcomes you into this elegant home featuring a fireplaced living room with built-ins and a grand dining room with floor-to-ceiling windows and butler’s pantry—ideal for entertaining. The bright chef’s kitchen showcases white cabinetry, a large marble island, Wolf and Sub-Zero

    Debi Benoit William Raveis R.E. & Home Services

    43 Bristol Rd, Wellesley Hills, MA 02481
  • /4

    $2,180,000 Sold Aug 29, 2025

    67 Old Colony Rd, Wellesley Hills, MA 02481

    • Land
    • 0.53 Acre
    • $4,113,208 per Acre

    Last Sold Summary

    • 14 Days On Market

    Current Estimated Value $2,081,130

    Last Listing Agent Christine Lawrence Rutledge Properties

    67 Old Colony Rd, Wellesley Hills, MA 02481
    • /39

      Est $1,469,399 Not Listed For Sale

      721 Worcester St, Wellesley Hills, MA 02481

      • 4 Beds
      • 2.5 Baths
      • 2,416 Sq Ft
      • Built 1960
      721 Worcester St, Wellesley Hills, MA 02481

      Last Sold Summary

      • 35% Above List Price
      • $449/SF
      • 7 Days On Market

      Last Sold Price $1,085,000

      Last Listing Agent Peter Giannikopoulos Coldwell Banker Realty - Boston

  • /41

    $4,295,000 New Construction

    • 6 Beds
    • 5.5 Baths
    • 7,047 Sq Ft

    201 Lowell Rd, Wellesley Hills, MA 02481

    New home in Cliff Estates with the ideal floor plan and one of Wellesley's favorite designers creating the perfect interior! Gracious foyer with large kitchen family room off of the back of the home. Oversized kitchen island with fireplace in family room. First floor private study. Living room with another fireplace and dining room both with custom millwork. Mudroom with cubbies and closet.

    Melissa Dailey Coldwell Banker Realty - Wellesley

    201 Lowell Rd, Wellesley Hills, MA 02481
  • /36

    $4,100,000 Sold Apr 01, 2026

    18 Sprague Rd, Wellesley Hills, MA 02481

    • 6 Beds
    • 6.5 Baths
    • 7,962 Sq Ft
    • Built 2024

    Last Sold Summary

    • 13% Below List Price
    • $515/SF
    • 135 Days On Market

    Current Estimated Value $4,409,261

    Last Listing Agent Catherine Bassick Douglas Elliman Real Estate - Park Plaza

    18 Sprague Rd, Wellesley Hills, MA 02481
    • /37

      Est $3,034,673 Not Listed For Sale

      40 Oakridge Rd, Wellesley Hills, MA 02481

      • 5 Beds
      • 4.5 Baths
      • 5,500 Sq Ft
      • Built 1963
      40 Oakridge Rd, Wellesley Hills, MA 02481

      Last Sold Summary

      • 15% Above List Price
      • $482/SF
      • 29 Days On Market

      Last Sold Price $2,650,000

      Last Listing Agent Melissa Dailey Coldwell Banker Realty - Wellesley

  • /25

    $1,995,000 Pending

    • 5 Beds
    • 3.5 Baths
    • 3,985 Sq Ft

    81 Audubon Rd, Wellesley Hills, MA 02481

    Welcome home to this wonderful Colonial. The fireplaced living room has beautiful cabinets and the adjacent sunny office space makes working from home a pleasure. The dining room with a custom built-in, is ready for holidays and celebrations, while the newly updated kitchen truly serves as the heart of the home. Featuring ample cabinetry, Cambria quartz countertops, stainless steel appliances,

    Teri Adler MGS Group Real Estate LTD - Wellesley

    81 Audubon Rd, Wellesley Hills, MA 02481
  • /40

    $4,350,000 Sold Dec 11, 2025

    15 Essex Rd, Wellesley Hills, MA 02481

    • 6 Beds
    • 8 Baths
    • 7,577 Sq Ft
    • Built 2010

    Last Sold Summary

    • 5% Below List Price
    • $574/SF
    • 36 Days On Market

    Current Estimated Value $4,431,964

    Last Listing Agent Allison David Poirier Coldwell Banker Realty - Wellesley

    15 Essex Rd, Wellesley Hills, MA 02481
    • /28

      Est $4,274,452 Not Listed For Sale

      22 Oakridge Rd, Wellesley Hills, MA 02481

      • 5 Beds
      • 5.5 Baths
      • 7,336 Sq Ft
      • Built 2017
      22 Oakridge Rd, Wellesley Hills, MA 02481

      Last Sold Summary

      • 11% Above List Price
      • $525/SF
      • 100 Days On Market

      Last Sold Price $3,850,000

      Last Listing Agent Meghan Sutherland MGS Group Real Estate LTD - Wellesley

  • /42

    $2,995,000

    • 6 Beds
    • 6 Baths
    • 5,806 Sq Ft

    42 Edmunds Rd, Wellesley Hills, MA 02481

    Welcome home to this spacious and elegant colonial farmhouse nestled on its own private hill in the coveted Cliff Estates. The home perfectly blends the charm and character of an original farmhouse (including 8 original fireplaces) with modern features that suit today's lifestyle, such as multiple options for home office spaces. Five bedrooms (including primary suite) are located on the second

    Rachel Lieberman Berkshire Hathaway HomeServices Commonwealth Real Estate

    42 Edmunds Rd, Wellesley Hills, MA 02481
  • /30

    $2,420,000 Sold Jun 30, 2025

    201 Bristol Rd, Wellesley Hills, MA 02481

    • 4 Beds
    • 2.5 Baths
    • 3,712 Sq Ft
    • Built 1957

    Last Sold Summary

    • 16% Above List Price
    • $652/SF
    • 2 Days On Market

    Current Estimated Value $2,435,228

    Last Listing Agent Melissa Dailey Coldwell Banker Realty - Wellesley

    201 Bristol Rd, Wellesley Hills, MA 02481
    • /38

      Est $5,112,102 Not Listed For Sale

      182 Bristol Rd, Wellesley Hills, MA 02481

      • 7 Beds
      • 6.5 Baths
      • 8,200 Sq Ft
      • Built 2024
      182 Bristol Rd, Wellesley Hills, MA 02481

      Last Sold Summary

      • 3% Below List Price
      • $645/SF
      • 91 Days On Market

      Last Sold Price $5,285,000

      Last Listing Agent Donahue Maley & Burns Team Compass

  • /35

    $3,150,000 Pending

    • 5 Beds
    • 5.5 Baths
    • 4,785 Sq Ft

    44 Bradford Rd, Wellesley Hills, MA 02481

    Privately nestled on nearly an acre of land this exceptional Cliff Estates home offers timeless elegance in a stunning and serene setting. Sweeping heated driveway with gorgeous stone walls lead up to beautiful front yard. The gracious two story foyer welcomes you with soaring ceilings, intricate millwork and rich hardwood floors throughout. Sophisticated fireplaced living room and sun splashed

    The Shulkin Wilk Group Compass

    44 Bradford Rd, Wellesley Hills, MA 02481
  • /42

    $4,510,000 Sold Jul 23, 2025

    10 Taylor Rd, Wellesley Hills, MA 02481

    • 7 Beds
    • 7 Baths
    • 6,888 Sq Ft
    • Built 1999

    Last Sold Summary

    • 6% Above List Price
    • $655/SF
    • 2 Days On Market

    Current Estimated Value $4,296,079

    Last Listing Agent The Lara & Chelsea Collaborative Coldwell Banker Realty - Wellesley

    10 Taylor Rd, Wellesley Hills, MA 02481
    • /39

      Est $3,057,876 Not Listed For Sale

      37 Oakridge Rd, Wellesley Hills, MA 02481

      • 5 Beds
      • 5 Baths
      • 5,066 Sq Ft
      • Built 1963
      37 Oakridge Rd, Wellesley Hills, MA 02481

      Last Sold Summary

      • 3% Below List Price
      • $622/SF
      • 3 Days On Market

      Last Sold Price $3,150,000

      Last Listing Agent Jennifer Madden Coldwell Banker Realty - Wellesley

  • /27

    $2,349,800

    • 4 Beds
    • 3.5 Baths
    • 3,406 Sq Ft

    53 Audubon Rd, Wellesley Hills, MA 02481

    Elegant Colonial with exceptional curb appeal in Wellesley Hills’ coveted Cliff Estates. This beautifully updated home offers 4 beds/3.5 baths, and a flexible floor plan for everyday living and entertaining. The front-to-back living room with fireplace is filled with natural light, while the formal dining room adds classic charm. The renovated eat-in kitchen features an island, granite

    Dan Li Keller Williams Realty

    53 Audubon Rd, Wellesley Hills, MA 02481
  • /4

    $5,495,000 Sold Jun 11, 2025

    18 Old Colony Rd, Wellesley Hills, MA 02481

    • 5 Beds
    • 8 Baths
    • 7,417 Sq Ft
    • Built 2025

    Last Sold Summary

    • $741/SF
    • 3 Days On Market

    Current Estimated Value $5,348,772

    Last Listing Agent Prudence Hay Rutledge Properties

    18 Old Colony Rd, Wellesley Hills, MA 02481
    • /29

      Est $2,389,871 Not Listed For Sale

      66 Suffolk Rd, Wellesley Hills, MA 02481

      • 4 Beds
      • 4.5 Baths
      • 3,546 Sq Ft
      • Built 1956
      66 Suffolk Rd, Wellesley Hills, MA 02481

      Last Sold Summary

      • 6% Above List Price
      • $635/SF
      • 5 Days On Market

      Last Sold Price $2,251,000

      Last Listing Agent Adriano Varano Keller Williams Realty

  • /42

    $3,400,000 Sold May 02, 2025

    229 Bristol Rd, Wellesley Hills, MA 02481

    • 4 Beds
    • 4.5 Baths
    • 5,000 Sq Ft
    • Built 2016

    Last Sold Summary

    • 14% Above List Price
    • $680/SF
    • 0 Days On Market

    Current Estimated Value $3,371,793

    Last Listing Agent Jean Piazza Gibson Sotheby's International Realty

    229 Bristol Rd, Wellesley Hills, MA 02481
    • /39

      Est $4,706,952 Not Listed For Sale

      22 Suffolk Rd, Wellesley Hills, MA 02481

      • 7 Beds
      • 6.5 Baths
      • 7,200 Sq Ft
      • Built 2023
      22 Suffolk Rd, Wellesley Hills, MA 02481

      Last Sold Summary

      • 6% Above List Price
      • $618/SF
      • 118 Days On Market

      Last Sold Price $4,450,000

      Last Listing Agent The Lara & Chelsea Collaborative Coldwell Banker Realty - Wellesley

  • /13

    $2,600,000 Sold May 09, 2025

    77 Arnold Rd, Wellesley Hills, MA 02481

    • 4 Beds
    • 3.5 Baths
    • 3,266 Sq Ft
    • Built 1935

    Last Sold Summary

    • 24% Above List Price
    • $796/SF
    • 2 Days On Market

    Current Estimated Value $2,668,212

    Last Listing Agent Maura Rodino Berkshire Hathaway HomeServices Commonwealth Real Estate

    77 Arnold Rd, Wellesley Hills, MA 02481
    • /35

      Est $3,016,204 Not Listed For Sale

      49 Tanglewood Rd, Wellesley Hills, MA 02481

      • 5 Beds
      • 5 Baths
      • 5,455 Sq Ft
      • Built 1960
      49 Tanglewood Rd, Wellesley Hills, MA 02481

      Last Sold Summary

      • 9% Above List Price
      • $509/SF
      • 4 Days On Market

      Last Sold Price $2,775,000

      Last Listing Agent Chadwick White Compass

  • /42

    $4,280,000 Sold Dec 04, 2025

    36 Oakridge Rd, Wellesley Hills, MA 02481

    • 6 Beds
    • 6.5 Baths
    • 7,029 Sq Ft
    • Built 2021

    Last Sold Summary

    • 22% Below List Price
    • $609/SF
    • 247 Days On Market

    Current Estimated Value $4,403,557

    Last Listing Agent George Sarkis Douglas Elliman Real Estate - The Sarkis Team

    36 Oakridge Rd, Wellesley Hills, MA 02481
    • /41

      Est $3,197,210 Not Listed For Sale

      120 Hampshire Rd, Wellesley Hills, MA 02481

      • 4 Beds
      • 4.5 Baths
      • 3,200 Sq Ft
      • Built 1954
      120 Hampshire Rd, Wellesley Hills, MA 02481

      Last Sold Summary

      • 7% Below List Price
      • $1,078/SF
      • 1 Day On Market

      Last Sold Price $3,450,000

      Last Listing Agent Debi Benoit William Raveis R.E. & Home Services

  • /29

    $3,500,000 Sold Jul 14, 2025

    202 Bristol Rd, Wellesley Hills, MA 02481

    • 6 Beds
    • 9 Baths
    • 6,156 Sq Ft
    • Built 2001

    Last Sold Summary

    • 3% Above List Price
    • $569/SF
    • 3 Days On Market

    Current Estimated Value $3,771,611

    Last Listing Agent Teri Adler MGS Group Real Estate LTD - Wellesley

    202 Bristol Rd, Wellesley Hills, MA 02481
    • /24

      Est $1,964,623 Not Listed For Sale

      3 Sprague Rd, Wellesley Hills, MA 02481

      • 5 Beds
      • 5 Baths
      • 3,480 Sq Ft
      • Built 1955
      3 Sprague Rd, Wellesley Hills, MA 02481

      Last Sold Summary

      • 35% Above List Price
      • $420/SF
      • 2 Days On Market

      Last Sold Price $1,460,000

      Last Listing Agent Meghan Sutherland MGS Group Real Estate LTD - Wellesley

  • /24

    $2,500,000 Sold Aug 14, 2025

    15 Barnstable Rd, Wellesley Hills, MA 02481

    • 4 Beds
    • 4 Baths
    • 3,097 Sq Ft
    • Built 1950

    Last Sold Summary

    • $807/SF
    • 8 Days On Market

    Current Estimated Value $2,437,450

    Last Listing Agent Betsy Kessler Rutledge Properties

    15 Barnstable Rd, Wellesley Hills, MA 02481
    • /38

      Est $4,194,071 Not Listed For Sale

      178 Lowell Rd, Wellesley Hills, MA 02481

      • 5 Beds
      • 6 Baths
      • 6,253 Sq Ft
      • Built 2008
      178 Lowell Rd, Wellesley Hills, MA 02481

      Last Sold Summary

      • 9% Above List Price
      • $618/SF
      • 2 Days On Market

      Last Sold Price $3,865,000

      Last Listing Agent Melissa Dailey Coldwell Banker Realty - Wellesley

Showing Results 1 - 40, Page 1 of 18

Home Trends in Cliff Estates, MA

Housing Trends

Median Sale Price
$2,875,000
Median Single Family Sale Price
$3,115,000
Average Price Per Sq Ft
$666
Number of Homes for Sale
6
Last 12 months Home Sales
23
Months of Supply
3.10
Median List Price
$2,995,000
Median Change From 1st List Price
2%
Median Home Sale Price YoY Change
11%
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