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Recently Sold Cliff Estates Homes

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  • /42

    $4,510,000 Sold Jul 23, 2025

    • 6,888 Sq Ft
    • $655/SF
    • 2 Days On Market
    • 7 Beds
    • 7 Baths
    • Built 1999

    10 Taylor Rd, Wellesley Hills, MA 02481

    Nestled in the prestigious Cliff Estates, this stunning young colonial offers a perfect blend of classic elegance and modern luxury. With 7 spacious bedrooms, including a private in-law suite, this home provides ample space for multi-generational living or guests. Designed for today’s lifestyle, it features two dedicated work-from-home spaces, ideal for productivity and privacy.The heart of the

    The Lara & Chelsea Collaborative Coldwell Banker Realty - Wellesley

    10 Taylor Rd, Wellesley Hills, MA 02481
  • /29

    $3,500,000 Sold Jul 14, 2025

    • 6,156 Sq Ft
    • $569/SF
    • 3 Days On Market
    • 6 Beds
    • 9 Baths
    • Built 2001

    202 Bristol Rd, Wellesley Hills, MA 02481

    Stunning Cliff Estates Colonial. This lovely and expansive home boasts soaring ceilings and sparkling hardwoods. There is a gorgeous kitchen with top appliances and a crisp clean design that opens to an exceptional breakfast area. The open fireplaced family room has coffered ceilings/built ins. Sliding doors lead to a new three season porch featuring blue stone floors, teak ceilings, a large wood

    Teri Adler MGS Group Real Estate LTD - Wellesley

    202 Bristol Rd, Wellesley Hills, MA 02481
  • /30

    $2,420,000 Sold Jun 30, 2025

    • 3,712 Sq Ft
    • $652/SF
    • 2 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1957

    201 Bristol Rd, Wellesley Hills, MA 02481

    Cliff Estates! Move into this 4 bedroom and 3 bath center entrance colonial! Kitchen with breakfast bar opens to both a very large family room and sunroom. Sunfilled family room with windows on 3 sides large enough for huge couches and even a second sitting area! Skylit sunroom with access to deck overlooks half acre lot with inground heated pool. Traditional living room with wood fireplace plus

    Melissa Dailey Coldwell Banker Realty - Wellesley

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

    $5,495,000 Sold Jun 11, 2025

    • 7,417 Sq Ft
    • $741/SF
    • 3 Days On Market
    • 5 Beds
    • 8 Baths
    • Built 2025

    18 Old Colony Rd, Wellesley Hills, MA 02481

    Discover the opportunity of a lifetime nestled in the prestigious Cliff Estates - a to be built Colonial merging architectural excellence w/ modern luxury. This inviting home will feature spacious rooms adorned w/ elegant white oak floors, custom cabinetry & built-ins. The expansive 1st floor will be an entertainer’s dream, boasting a stunning kitchen/family room combo & formal dining & living

    Prudence Hay Rutledge Properties

    18 Old Colony Rd, Wellesley Hills, MA 02481
  • /31

    $2,610,000 Sold Jun 02, 2025

    • 3,390 Sq Ft
    • $770/SF
    • 3 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 1927

    12 Cypress Rd, Wellesley Hills, MA 02481

    Elegant 10-room brick Colonial Revival-style residence in Old Cliff Estates. This lovely home features a welcoming entryway, a front-to-back living room w/fireplace and adjacent sunroom, dining room with custom built-in cabinets, and a chef’s kitchen with marble and stone countertops with stainless steel appliances including a wine chiller. A sunny family room, a large mudroom, and half bathroom

    Susan Evans Hammond Residential Real Estate

    12 Cypress Rd, Wellesley Hills, MA 02481
  • /39

    $2,875,000 Sold May 28, 2025

    • 3,829 Sq Ft
    • $751/SF
    • 7 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 1954

    110 Hampshire Rd, Wellesley Hills, MA 02481

    Located in the heart of Cliff Estates, this elegant center-entrance Colonial sits on a beautifully landscaped .64 acre private lot, seamlessly blending formal and casual living. The sun-drenched gourmet kitchen features 2” Calacatta countertops, Wolf & Sub-Zero appliances, custom cabinetry, wine cooler, and a charming breakfast nook.The first floor also boasts a spacious dining room, a family

    Debi Benoit William Raveis R.E. & Home Services

    110 Hampshire Rd, Wellesley Hills, MA 02481
  • /13

    $2,600,000 Sold May 09, 2025

    • 3,266 Sq Ft
    • $796/SF
    • 2 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1935

    77 Arnold Rd, Wellesley Hills, MA 02481

    Unlock the potential of this substantial Wellesley Hills Colonial, set on a private 1.17-acre parcel. With over 3,200 sq ft of living space, this five-bedroom, 3.5-bath home offers remarkable flexibility. This home boasts a formal entry w/wainscoting & two closets. The front-to-back living room has a fireplace & ushers you to the tiled family room w/fireplace, built-in indoor grill & bar for

    Maura Rodino Berkshire Hathaway HomeServices Commonwealth Real Estate

    77 Arnold Rd, Wellesley Hills, MA 02481
  • /42

    $3,400,000 Sold May 02, 2025

    • 5,000 Sq Ft
    • $680/SF
    • 0 Days On Market
    • 4 Beds
    • 4.5 Baths
    • Built 2016

    229 Bristol Rd, Wellesley Hills, MA 02481

    Step into this stunning 2016 Cliff Estates Colonial, where timeless elegance meets modern convenience. The bright & open floor plan, soaring 9'+ ceilings, gleaming hardwood floors, including coffered ceilings, wainscoting, chair rail accents & designer window treatments. Designed for both work & play, the main level offers a dedicated home office space while seamlessly flowing into the chef's

    Jean Piazza Gibson Sotheby's International Realty

    229 Bristol Rd, Wellesley Hills, MA 02481
  • /31

    $3,700,000 Sold May 01, 2025

    • 4,558 Sq Ft
    • $812/SF
    • 13 Days On Market
    • 5 Beds
    • 6 Baths
    • Built 1909

    21 Cushing Rd, Wellesley Hills, MA 02481

    Discover luxury and sophistication in this renovated/expanded 5-bedroom, 6-bathroom Cliff Estates masterpiece. Set on a manicured lot, this home offers 4 levels of meticulously designed living space. The grand foyer leads to elegant living and dining areas with custom millwork, rich hardwood floors, and oversized windows. The chef’s kitchen boasts an oversized island, top-tier appliances, wet

    Jennifer Fish Gibson Sotheby's International Realty

    21 Cushing Rd, Wellesley Hills, MA 02481
  • /34

    $2,100,000 Sold Apr 29, 2025

    • 3,226 Sq Ft
    • $651/SF
    • 6 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1957

    3 Dukes Rd, Wellesley Hills, MA 02481

    In one of Wellesley’s most sought-after neighborhoods on a corner lot. This home is truly one of a kind. The main floor has stainless appliances, cherry cabinets and a spacious living/dining room that looks out through the bay window to the yard. First floor also offers a work from home space and a sun room. Upstairs, 3 full baths and yes, 7 bedrooms. There is a finished basement with a

    Jennifer Reidy Seaport Realty Group

    3 Dukes Rd, Wellesley Hills, MA 02481
  • /29

    $1,800,000 Sold Mar 25, 2025

    • 2,866 Sq Ft
    • $628/SF
    • 260 Days On Market
    • 4 Beds
    • 4 Baths
    • Built 1962

    209 Bristol Rd, Wellesley Hills, MA 02481

    Broker Open cancelled . Offer accepted. Now priced to sell !! Nestled in the heart of Cliff Estates, this expansive, charming colonial awaits its next owner. Lovely foyer leads to spacious kitchen, dining room and three season porch. Large living / great room with fireplace and wood accent wall. Hardwood floors in most rooms. The second level boasts a primary suite with ample closet space and

    Moira Lown Coldwell Banker Realty - Wellesley

    209 Bristol Rd, Wellesley Hills, MA 02481
  • /41

    $2,535,000 Sold Feb 27, 2025

    • 3,691 Sq Ft
    • $687/SF
    • 1 Day On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1940

    24 Arnold Rd, Wellesley Hills, MA 02481

    Nestled in the picturesque Cliff Estates a highly sought-after neighborhood, this sun-filled colonial is a true gem. From the moment you arrive, you will be captivated by its charming curb appeal and manicured landscaping.The natural light pours through oversized windows, illuminating the gleaming hardwood floors and highlighting the thoughtful design of every room. The spacious living room with

    The Lara & Chelsea Collaborative Coldwell Banker Realty - Wellesley

    24 Arnold Rd, Wellesley Hills, MA 02481
  • /40

    $1,300,000 Sold Jan 31, 2025

    • 3,291 Sq Ft
    • $395/SF
    • 79 Days On Market
    • 6 Beds
    • 3 Baths
    • Built 1870

    679 Worcester St, Wellesley, MA 02481

    Stately Mansard Colonial sits on oversized 3/4 acre lot. This home is perfect for entertaining with its updated eat in kitchen with granite counters & gas cooking that leads to a large deck for summer pleasure. A formal dining room with gas fireplace & a living room with wood burning fire place and a 1st floor office or bedroom, most with glistening hardwood floors, plus an updated bath w/ 1st

    Cammy Bille J. Barrett & Company

    679 Worcester St, Wellesley, MA 02481
  • /39

    $1,085,000 Sold Jan 17, 2025

    • 2,416 Sq Ft
    • $449/SF
    • 7 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1960

    721 Worcester St, Wellesley Hills, MA 02481

    Introducing a charming 4-bedroom, 2.5-bath Colonial in Wellesley. This well-maintained home offers a versatile floor plan designed for both comfort and functionality. The sunlit living room featuring a cozy fireplace, flows seamlessly into the formal dining room, perfect for hosting gatherings. The kitchen boasts ample cabinet space, a breakfast nook, and direct access to the side entry. A

    Peter Giannikopoulos Coldwell Banker Realty - Boston

    721 Worcester St, Wellesley Hills, MA 02481
  • /29

    $2,251,000 Sold Jan 08, 2025

    • 3,546 Sq Ft
    • $635/SF
    • 5 Days On Market
    • 4 Beds
    • 4.5 Baths
    • Built 1956

    66 Suffolk Rd, Wellesley Hills, MA 02481

    This welcoming colonial home offers a spacious and comfortable retreat with features designed for both comfort and style. The main floor features a sunlit kitchen w/ granite countertops, a large family room w/ a cozy fireplace ideal for gatherings w/access to the private deck & yard, a formal living w/fireplace and formal dining room w/built in cabinet, powder room & direct access to the two car

    Adriano Varano Keller Williams Realty

    66 Suffolk Rd, Wellesley Hills, MA 02481
  • /34

    $2,995,000 Sold Dec 06, 2024

    • 5,195 Sq Ft
    • $577/SF
    • 19 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 1936

    45 Old Colony Rd, Wellesley Hills, MA 02481

    Stately center entrance colonial set in the heart of the Cliff Estates with park-like grounds. This is a truly special home that embraces light and has airy interior design. The open family room is inviting with clean lines and serves as a welcoming gathering space. There is a classic white eat-in kitchen that is clean and fresh with quartz counters and stainless appliances. A front to back

    Teri Adler MGS Group Real Estate LTD - Wellesley

    45 Old Colony Rd, Wellesley Hills, MA 02481
  • /38

    $5,285,000 Sold Nov 08, 2024

    • 8,200 Sq Ft
    • $645/SF
    • 91 Days On Market
    • 7 Beds
    • 6.5 Baths
    • Built 2024

    182 Bristol Rd, Wellesley Hills, MA 02481

    Magnificent 7-bedroom home in Wellesley's Cliff Estates blends transitional design, custom craftsmanship, and state-of-the-art systems. Thoughtfully designed with soaring ceilings, oversized windows, and curated stone and wood accents, this home is filled with warmth and light. The first floor features a dramatic foyer, entertainment-sized living and dining rooms, a custom kitchen with 2 islands,

    Donahue Maley & Burns Team Compass

    182 Bristol Rd, Wellesley Hills, MA 02481
  • /6

    $2,450,000 Sold Oct 04, 2024

    • Land
    • 0.74 Acre
    • $3,310,811 per Acre
    • 9 Days On Market

    17 Suffolk Rd, Wellesley Hills, MA 02481

    This property is in an uninhabitable, tear down condition, value is in the LAND. Rarely available 0.74 Acre (32,303 Sf) level lot with gentle slope in the back, surrounded by new construction homes. Subject to license to sell from Norfolk County Probate Court.

    Susie Hsu Move2Boston Group, LLC

    17 Suffolk Rd, Wellesley Hills, MA 02481
  • /27

    $2,830,000 Sold Sep 30, 2024

    • 3,050 Sq Ft
    • $928/SF
    • 6 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1957

    88 Albion Rd, Wellesley Hills, MA 02481

    Picture Perfect! A gracious circular driveway welcomes you to this sophisticated, stylish and inviting home in the heart of Cliff Estates. The stunning interior of this classic New England residence is the definition of living life to the fullest! Sun-splashed spaces and abundant windows highlight natural light and views of lush manicured grounds. A soothing palate throughout accentuates clean,

    Jill Boudreau eXp Realty

    88 Albion Rd, Wellesley Hills, MA 02481
  • /36

    $2,650,000 Sold Aug 30, 2024

    • 3,964 Sq Ft
    • $669/SF
    • 1 Day On Market
    • 4 Beds
    • 4.5 Baths
    • Built 1933

    33 Chatham Cir, Wellesley Hills, MA 02481

    OPEN HOUSE CANCELLED - OFFER ACCEPTED! This charming & sophisticated Cape in the sought after Cliff Estates has been significantly renovated from top to bottom by well-respected local builder. This inviting property features wonderful living space & custom detail throughout. The updated chef’s kitchen includes custom wood cabinetry, an oversized island w/gourmet chef prep sink & touch-less faucet

    Jennifer Madden Coldwell Banker Realty - Wellesley

    33 Chatham Cir, Wellesley Hills, MA 02481
  • /18

    $805,000 Sold Aug 15, 2024

    • 2,188 Sq Ft
    • $368/SF
    • 3 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1959

    603 Worcester St, Wellesley Hills, MA 02481

    Welcome to this open and spacious mid-century modern home with oversized rooms throughout. The house is designed with great architectural detail and 3 large bedrooms, living/dining rooms, family room and kitchen. This house has been immaculately maintained and cared for by one owner and all it needs now is for the new owner to bring their decorating flare to bring this home into the next century.

    Noah Pearlstein Gibson Sotheby's International Realty

    603 Worcester St, Wellesley Hills, MA 02481
  • /35

    $4,250,000 Sold Aug 09, 2024

    • 5,000 Sq Ft
    • $850/SF
    • 2 Days On Market
    • 5 Beds
    • 4.5 Baths
    • Built 1937

    14 Plymouth Rd, Wellesley Hills, MA 02481

    Spectacular 5 bedroom Colonial renovated to perfection and sited on one of the best lots in the Cliff estates. Filled with designer finishes and fixtures throughout with curated spaces designed to maximize efficiency and luxurious living, the first floor is anchored by the newly renovated kitchen with new Subzero/Wolf appliances, Quartz counters and custom cabinetry that opens to the breathtaking

    Donahue Maley & Burns Team Compass

    14 Plymouth Rd, Wellesley Hills, MA 02481
  • /39

    $3,150,000 Sold Aug 07, 2024

    • 5,066 Sq Ft
    • $622/SF
    • 3 Days On Market
    • 5 Beds
    • 5 Baths
    • Built 1963

    37 Oakridge Rd, Wellesley Hills, MA 02481

    A stunningly renovated and expanded Porter colonial located in the desirable Cliff Estates. This 12 room home features 5 bedrooms, 3 full and 2 half baths, spread over 5,066 square feet of generous living space. The large, open kitchen-family room is a chef's dream and is perfect for gatherings. A natural flow out to an expansive bluestone patio with sitting wall overlooks just under 1/2 acre of

    Jennifer Madden Coldwell Banker Realty - Wellesley

    37 Oakridge Rd, Wellesley Hills, MA 02481
  • /2

    $2,225,000 Sold Jun 12, 2025

    • 3,045 Sq Ft
    • $731/SF
    • 4 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1940

    30 Audubon Rd, Wellesley Hills, MA 02481

    Located in the coveted Cliff Estates, this well-maintained 4-bed, 2.5-bath home presents a rare opportunity to live in one of Wellesley’s most desirable tree-lined neighborhoods. First floor offers warm & inviting living spaces, including two fireplaces—one of which is double-sided, connecting living room & office. Chef’s kitchen features an exquisite concrete countertop, 48” Wolf cooktop w/6

    O & C Homes Team William Raveis R.E. & Home Services

    30 Audubon Rd, Wellesley Hills, MA 02481
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