63

Wellesley, MA Houses for Sale

Section Image Section Image
  • 29 Water St, Natick, MA 01760
    29 Water St, Natick, MA 01760
    29 Water St, Natick, MA 01760
    /42

    $1,740,000 Open Sat 12PM - 2PM

    • 5 Beds
    • 2.5 Baths
    • 3,422 Sq Ft

    29 Water St, Natick, MA 01760

    Set along the banks of the Charles River, this stunning home blends luxury, function, and an idyllic natural setting. Behind its modest facade, the interior unfolds as a custom contemporary retreat. Sweeping river views and frequent wildlife sightings keep you connected to nature. The 2nd-floor primary suite is a sanctuary with vaulted ceilings, a private balcony, and spa-like bath w/radiant heat

    Agent Photo

    Barbara Wales

    Engel & Volkers Newton

    (508) 290-6426

    29 Water St, Natick, MA 01760
  • 157 Edmunds Rd, Wellesley Hills, MA 02481
    157 Edmunds Rd, Wellesley Hills, MA 02481
    157 Edmunds Rd, Wellesley Hills, MA 02481
    /30

    $5,375,000 Open Sat 1PM - 2:30PM

    • 6 Beds
    • 8 Baths
    • 7,129 Sq Ft

    157 Edmunds Rd, Wellesley Hills, MA 02481

    Timeless elegance and classic architectural details entice you at 157 Edmunds Road, situated in a prime Cliff Estates neighborhood with lush landscaping and a serene setting. Approach the whitewashed brick exterior with slate roof and circular drive and experience the grandeur of this residence. Step into the generous foyer to access gracious living spaces including a stunning eat-in gourmet

    The Shulkin Wilk Group Compass

    157 Edmunds Rd, Wellesley Hills, MA 02481
  • 209 Bristol Rd, Wellesley Hills, MA 02481
    209 Bristol Rd, Wellesley Hills, MA 02481
    209 Bristol Rd, Wellesley Hills, MA 02481
    /28

    $3,495,000 Open Sat 11AM - 12:30PM

    • 6 Beds
    • 4.5 Baths
    • 4,424 Sq Ft

    209 Bristol Rd, Wellesley Hills, MA 02481

    Set on a tree-lined block in the coveted Cliff Estates enclave, this to-the-studs 2025 renovation and expansion of a classic New England Colonial is a singular achievement of brilliant design, timeless elegance, and refreshing livability. The expansive living spaces are distinguished by beautifully curated fixtures and finishes, from the fluted marble fireplace to bespoke lighting and hardware.

    Elisabeth Preis Compass

    209 Bristol Rd, Wellesley Hills, MA 02481
  • 182 Winding River Rd, Wellesley, MA 02482
    182 Winding River Rd, Wellesley, MA 02482
    182 Winding River Rd, Wellesley, MA 02482
    /40

    $5,895,000 Open Sat 11:30AM - 1PM

    • 6 Beds
    • 8 Baths
    • 9,848 Sq Ft

    182 Winding River Rd, Wellesley, MA 02482

    Custom home on the Charles River. Incredible views of the river and conservation land beyond plus a dock for kayaks, paddleboards & small electric boats! 2006 new construction w/over 9000 sq ft of living space on 1.73 acres. Walk into dramatic great room w/ 2 story windows plus one of four fireplaces & custom window seat perfect for entertaining. NEWLY renovated white kitchen w/ center island,

    Melissa Dailey Coldwell Banker Realty - Wellesley

    182 Winding River Rd, Wellesley, MA 02482
  • 3 Ravine Rd, Wellesley Hills, MA 02481
    3 Ravine Rd, Wellesley Hills, MA 02481
    3 Ravine Rd, Wellesley Hills, MA 02481
    /33

    $5,495,000

    • 5 Beds
    • 8 Baths
    • 7,720 Sq Ft

    3 Ravine Rd, Wellesley Hills, MA 02481

    Nestled in the heart of coveted Wellesley Farms, this chic sun-filled brick colonial seamlessly blends timeless elegance with modern comfort. Set on a beautifully landscaped private lot, the home welcomes with classic curb appeal and a gracious entry. Sunlight pours into the well-appointed formal living and dining rooms, creating inviting spaces ideal for entertaining. The thoughtful layout flows

    The Lara & Chelsea Collaborative Coldwell Banker Realty - Wellesley

    3 Ravine Rd, Wellesley Hills, MA 02481
  • 85 Monadnock Rd, Wellesley Hills, MA 02481
    85 Monadnock Rd, Wellesley Hills, MA 02481
    85 Monadnock Rd, Wellesley Hills, MA 02481
    /42

    $4,295,000 Open Sat 11AM - 12:30PM

    • 6 Beds
    • 7.5 Baths
    • 7,240 Sq Ft

    85 Monadnock Rd, Wellesley Hills, MA 02481

    Welcome to this inviting and thoughtfully designed home in the Pierce Estates neighborhood of Wellesley. With generous living areas and well-planned spaces throughout, this property is ideal for both everyday life and entertaining.As you step inside, you're welcomed by a striking two-story foyer that sets the stage for the rest of the home. The main level includes a quiet home office, perfect for

    Alina Wang Coldwell Banker Realty - Lexington

    85 Monadnock Rd, Wellesley Hills, MA 02481
  • 7 Mountview Rd, Wellesley Hills, MA 02481
    7 Mountview Rd, Wellesley Hills, MA 02481
    7 Mountview Rd, Wellesley Hills, MA 02481
    /34

    $6,500,000 Open Sat 11:30AM - 1PM

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

    7 Mountview Rd, Wellesley Hills, MA 02481

    Ready to Welcome you Home! Stunning New Construction Colonial w everything on your wish list. Exceptional sunny and private backyard - check! Quiet cul de sac - check! Prestigious Cliff Estates location - check! 10’ ceilings - check! GAS heat, cooking, and fireplaces - check! Open concept kitchen, family room, breakfast room - check! Beautiful formal rooms - check! Ensuite baths - check! Rec room

    Christine Lawrence Rutledge Properties

    7 Mountview Rd, Wellesley Hills, MA 02481
  • 9 Hampden St, Wellesley, MA 02482
    9 Hampden St, Wellesley, MA 02482
    9 Hampden St, Wellesley, MA 02482
    /37

    $2,700,000 Open Sun 12PM - 2PM

    • 8 Beds
    • 6 Baths
    • 5,559 Sq Ft

    9 Hampden St, Wellesley, MA 02482

    Ideally located in the heart of Wellesley Center, 9–11 Hampden Street is a rare offering of gracious proportion, charm and timeless detail. With nearly 5,600 sq. ft. of living space across three sun-splashed finished floors, this stately residence offers 8 bedrooms and versatile living areas awaiting a discerning buyer’s vision. Sited on .37 acres, with a freshly painted interior, it is equally

    Jill Boudreau eXp Realty

    9 Hampden St, Wellesley, MA 02482
  • 93 Seaver St, Wellesley, MA 02481
    93 Seaver St, Wellesley, MA 02481
    93 Seaver St, Wellesley, MA 02481
    /35

    $2,695,000 Open Sun 12PM - 1PM

    • 5 Beds
    • 5 Baths
    • 5,200 Sq Ft

    93 Seaver St, Wellesley, MA 02481

    Incredible value for luxury new construction in the Hunnewell school district. Ideally located close to Wellesley Center + just minutes from the High School, this 5 bed, 5 bath Colonial impresses with its luxurious finishes, soaring ceilings and abundant natural light. The 1st floor offers a chef’s kitchen w/stainless appliances, walk-in pantry, quartz countertops and white cabinetry w/white oak

    Beyond Boston Properties Group Compass

    93 Seaver St, Wellesley, MA 02481
  • 46 Lincoln Rd, Wellesley Hills, MA 02481
    46 Lincoln Rd, Wellesley Hills, MA 02481
    46 Lincoln Rd, Wellesley Hills, MA 02481
    /39

    $2,795,000 Open Sat 11:30AM - 1PM

    • 4 Beds
    • 3.5 Baths
    • 3,705 Sq Ft

    46 Lincoln Rd, Wellesley Hills, MA 02481

    Love at first sight! Highly coveted brick Colonial in superb country club neighborhood! This much admired residence has exquisite curb appeal & seamlessly blends traditional charm with modern day conveniences for everyday living. Beautiful front to back living room showcases a gorgeous oversized fireplace with custom built-ins & moldings. The formal dining room provides a warm space for

    The Lara & Chelsea Collaborative Coldwell Banker Realty - Wellesley

    46 Lincoln Rd, Wellesley Hills, MA 02481
  • 18 Patton Rd, Wellesley, MA 02482
    18 Patton Rd, Wellesley, MA 02482
    18 Patton Rd, Wellesley, MA 02482
    /39

    $2,995,000

    • 6 Beds
    • 6.5 Baths
    • 5,985 Sq Ft

    18 Patton Rd, Wellesley, MA 02482

    Exceptional 6-bedroom, 6.5-bath, Colonial, in Wellesley’s desirable Woodlands neighborhood. Bathed in natural light, this home offers elegance, comfort, and modern convenience. At the heart of the home is a chef’s kitchen with stone countertops, center island, and premium appliances. The kitchen flows seamlessly into a formal dining room and spacious family room with coffered ceiling and gas

    Jinyang Zhang Coldwell Banker Realty - Weston

    18 Patton Rd, Wellesley, MA 02482
  • 20 Oakland St, Wellesley, MA 02481
    20 Oakland St, Wellesley, MA 02481
    20 Oakland St, Wellesley, MA 02481
    /40

    $3,549,000

    • 6 Beds
    • 7.5 Baths
    • 6,499 Sq Ft

    20 Oakland St, Wellesley, MA 02481

    **ENTRANCE @ 367 WORCESTER STREET** This stunning 6,500 sq ft colonial blends timeless design & modern luxury. Set back from Worcester Street, the home features a dramatic 2-story foyer, white oak floors, soaring ceilings & sunlit open living/dining spaces. Chef’s kitchen w/ Thermador appliances, quartz counters, waterfall island & stylish pendant lighting. Two rear decks connected by a stone

    Michael Tinsley Longwood Residential, LLC

    20 Oakland St, Wellesley, MA 02481
  • 2 Summit Rd, Wellesley, MA 02482
    2 Summit Rd, Wellesley, MA 02482
    2 Summit Rd, Wellesley, MA 02482
    /34

    $2,675,000

    • 4 Beds
    • 4.5 Baths
    • 3,693 Sq Ft

    2 Summit Rd, Wellesley, MA 02482

    History curated with modern simplicity in this newly renovated and expanded home. No surface has been left untouched. Living room, dining room and grand foyer offer elegant modern space. Chef's kitchen includes 48" Sub Zero fridge, 36" Wolf induction range and Bosch dishwasher. Direct access to granite patio and private yard. Half bath, breakfast nook, mudroom and oversized 2 car garage complete

    James Mealey Defining Real Estate

    2 Summit Rd, Wellesley, MA 02482
  • 32 Twitchell St, Wellesley, MA 02482
    32 Twitchell St, Wellesley, MA 02482
    32 Twitchell St, Wellesley, MA 02482
    /42

    $3,495,000

    • 6 Beds
    • 6 Baths
    • 6,364 Sq Ft

    32 Twitchell St, Wellesley, MA 02482

    This stunning custom-designed home perfectly balances elegance and everyday comfort. It combines all the best features of a home – location, style, luxury, comfort, space, and usability. A distinctive stone turret adds architectural charm, creating a unique circular dining room and a cozy retreat in the spacious primary suite. Sunlight floods the home through generous windows, enhancing its warm

    Hui Zou StartPoint Realty

    32 Twitchell St, Wellesley, MA 02482
  • 365 Worcester St, Wellesley, MA 02481
    365 Worcester St, Wellesley, MA 02481
    365 Worcester St, Wellesley, MA 02481
    /26

    $3,590,000

    • 6 Beds
    • 7 Baths
    • 7,000 Sq Ft

    365 Worcester St, Wellesley, MA 02481

    New Construction 2025! This classic brick-front New England colonial offers the ultimate luxury for all lifestyles. Perched between Washington Street and Worcester Street, this south-facing home is centrally located with access to all Wellesley offers with great commuter access. Dramatic grand entrance with a stunning staircase, huge windows, and an inviting foyer. Seven en-suite bedrooms over

    Erika Welch Rettman Associates

    365 Worcester St, Wellesley, MA 02481
  • 42 Edmunds Rd, Wellesley Hills, MA 02481
    42 Edmunds Rd, Wellesley Hills, MA 02481
    42 Edmunds Rd, Wellesley Hills, MA 02481
    /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 modern 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
  • 53 Mayo Rd, Wellesley, MA 02482
    53 Mayo Rd, Wellesley, MA 02482
    53 Mayo Rd, Wellesley, MA 02482
    /26

    $1,950,000 Open Fri 4:30PM - 6PM

    • 4 Beds
    • 3.5 Baths
    • 2,993 Sq Ft

    53 Mayo Rd, Wellesley, MA 02482

    Discover refined living in this exquisitely renovated Cape, ideally located in the most beloved of neighborhoods. Bathed in natural light, the open-concept floorplan showcases impeccable design and effortless sophistication. The chef’s kitchen stuns with marble countertops, custom cabinetry and a statement island—perfect for busy mornings and entertaining. The dining area opens to the beautiful,

    Lindsey Fay Kisielius Rutledge Properties

    53 Mayo Rd, Wellesley, MA 02482
  • 30 Southgate Rd, Wellesley, MA 02482
    30 Southgate Rd, Wellesley, MA 02482
    30 Southgate Rd, Wellesley, MA 02482
    /36

    $2,395,000 Open Sat 11:30AM - 1:30PM

    • 4 Beds
    • 2.5 Baths
    • 3,144 Sq Ft

    30 Southgate Rd, Wellesley, MA 02482

    Beautifully sited in one of Wellesley's most desirable neighborhoods, this classic Colonial offers easy access to the Brook Path, commuter rail to Boston, top-rated schools, playgrounds, and Wellesley's vibrant downtown. The expansive kitchen features a generous center island & sunny breakfast area with French doors leading to the stunning patio with built-in grill and refrigerator. The dining &

    Jane Collinson Advisors Living - Wellesley

    30 Southgate Rd, Wellesley, MA 02482
  • 50 Upson Rd, Wellesley, MA 02482
    50 Upson Rd, Wellesley, MA 02482
    50 Upson Rd, Wellesley, MA 02482
    /24

    $2,495,000 Open Sat 1PM - 2:30PM

    • 4 Beds
    • 3.5 Baths
    • 3,524 Sq Ft

    50 Upson Rd, Wellesley, MA 02482

    Nestled in Wellesley’s most upbeat neighborhood, this architect built residence offers elegant lifestyle within a vibrant community. Upon entry the flow of natural light, flawless floor plan, & master craftsmanship provides a seamless blend of comfort & practicality. 1st floor incl. a spacious living room w/ box beam ceilings, holiday sized formal dining room, stunning gourmet eat-in kitchen w/

    The Shulkin Wilk Group Compass

    50 Upson Rd, Wellesley, MA 02482
  • 8 Old Town Rd, Wellesley Hills, MA 02481
    8 Old Town Rd, Wellesley Hills, MA 02481
    8 Old Town Rd, Wellesley Hills, MA 02481
    /18

    $2,250,000

    • 5 Beds
    • 5 Baths
    • 2,614 Sq Ft

    8 Old Town Rd, Wellesley Hills, MA 02481

    Welcome to this Wellesley Farms Colonial, brimming with charm and maintained in excellent condition. Spacious dining and living rooms greet you on the first floor, flanked by an updated kitchen and bright sun room, respectively. In addition to the large primary and two additional bedrooms, the second floor boasts charming built-in bookshelves and a cozy office overlooking the front yard. Fourth

    Brian McMahon Rutledge Properties

    8 Old Town Rd, Wellesley Hills, MA 02481
  • 50 Parker Rd, Wellesley, MA 02482
    50 Parker Rd, Wellesley, MA 02482
    50 Parker Rd, Wellesley, MA 02482
    /26

    $1,595,000 Open Fri 4:30PM - 6PM

    • 4 Beds
    • 2.5 Baths
    • 2,147 Sq Ft

    50 Parker Rd, Wellesley, MA 02482

    This charming 1940 brick-front Garrison Colonial seamlessly marries timeless design with modern-day comfort. Situated in a highly desirable neighborhood, the home welcomes you with undeniable curb appeal and a warm, inviting presence. Inside, you’ll find 9 thoughtfully arranged rooms, including 4 spacious bedrooms and 2.5 baths, all spread across more than 2,000 square feet of living space. The

    Jennifer Madden Coldwell Banker Realty - Wellesley

    50 Parker Rd, Wellesley, MA 02482
  • 39 Twitchell St, Wellesley, MA 02482
    39 Twitchell St, Wellesley, MA 02482
    39 Twitchell St, Wellesley, MA 02482
    /37

    $1,995,000 Open Fri 4PM - 6PM

    • 4 Beds
    • 3 Baths
    • 2,475 Sq Ft

    39 Twitchell St, Wellesley, MA 02482

    Truly unique home in fabulous walk to everything location! Wonderful 1930’s Victorian Farmhouse loaded with charm and potential. Welcoming and large front porch, terrific high ceilings, original fir hardwood floors, plenty of sunshine and a natural open flow connecting all the living areas. Lovely entrance hall, wide open dining room and great room, and white eat-in kitchen. 4 bedrooms - with 3

    Christine Lawrence Rutledge Properties

    39 Twitchell St, Wellesley, MA 02482
  • 56 Pine Plain Rd, Wellesley Hills, MA 02481
    56 Pine Plain Rd, Wellesley Hills, MA 02481
    56 Pine Plain Rd, Wellesley Hills, MA 02481
    /17

    $1,475,000 Open Fri 4PM - 5:30PM

    • 4 Beds
    • 3 Baths
    • 2,265 Sq Ft

    56 Pine Plain Rd, Wellesley Hills, MA 02481

    Set on a quiet cul-de-sac near Bates Elementary in one of Wellesley’s most desirable neighborhoods, this elegant Colonial offers timeless charm with thoughtful updates. A new roof, refinished hardwood floors, and freshly painted interiors create a move-in ready home. The landscaped yard features fencing, stone patio, and irrigation system—ideal for outdoor living. Inside are four bedrooms, three

    Christine Norcross William Raveis R.E. & Home Services

    56 Pine Plain Rd, Wellesley Hills, MA 02481
  • 98 Great Plain Ave, Wellesley, MA 02482
    98 Great Plain Ave, Wellesley, MA 02482
    98 Great Plain Ave, Wellesley, MA 02482
    /33

    $2,499,000

    • 4 Beds
    • 4 Baths
    • 4,304 Sq Ft

    98 Great Plain Ave, Wellesley, MA 02482

    Step into 98 Great Plain Avenue—a newly transformed residence where modern sophistication meets classic appeal. Flooded with natural light, this exceptional home features soaring ceilings and a thoughtfully designed open-concept layout tailored to contemporary living. Rich hardwood floors and premium finishes define every inch of the interior, creating a refined yet welcoming ambiance. The chef’s

    Prudence Hay Rutledge Properties

    98 Great Plain Ave, Wellesley, MA 02482
  • 2 Longfellow Rd, Wellesley Hills, MA 02481
    2 Longfellow Rd, Wellesley Hills, MA 02481
    2 Longfellow Rd, Wellesley Hills, MA 02481
    /32

    $1,995,000 Open Fri 4PM - 6PM

    • 4 Beds
    • 3.5 Baths
    • 2,664 Sq Ft

    2 Longfellow Rd, Wellesley Hills, MA 02481

    Welcome to 2 Longfellow Road, this move-in ready gem is an exceptional opportunity to enjoy Wellesley living at its best. The newly renovated kitchen is the heart of the home, featuring white cabinetry, quartz countertops, and stainless steel appliances. With seamless flow into the dining room and direct access to the deck and private grounds, this space is perfect for entertaining family and

    George Sarkis Douglas Elliman Real Estate - The Sarkis Team

    2 Longfellow Rd, Wellesley Hills, MA 02481
  • 9 Ravine Rd, Wellesley Hills, MA 02481
    9 Ravine Rd, Wellesley Hills, MA 02481
    9 Ravine Rd, Wellesley Hills, MA 02481
    /42

    $8,490,000

    • 6 Beds
    • 11 Baths
    • 11,686 Sq Ft

    9 Ravine Rd, Wellesley Hills, MA 02481

    Discover the private compound you thought you'd never find - a hidden treasure in Wellesley Farms. This elusive signature property, with luxury amenities & a prime location, includes an exquisite primary residence, and an indoor outdoor clubhouse/sports complex, with state of the art facilities. Set amidst over an acre and a half of lush landscaped manicured grounds, including patios, putting

    The Lara & Chelsea Collaborative Coldwell Banker Realty - Wellesley

    9 Ravine Rd, Wellesley Hills, MA 02481
  • 19 Marvin Rd, Wellesley, MA 02482
    19 Marvin Rd, Wellesley, MA 02482
    19 Marvin Rd, Wellesley, MA 02482
    /33

    $2,299,000 Open Sat 11AM - 1PM

    • 4 Beds
    • 3 Baths
    • 3,606 Sq Ft

    19 Marvin Rd, Wellesley, MA 02482

    Beautiful Colonial set on a quiet, tree-lined street across from the Brook Path. The welcoming front porch sets the tone, while the location offers unmatched proximity to Wellesley Center, train, shops, schools, including the new Hunnewell Elementary. The bright, white kitchen w/quartzite & high-end appliances flows seamlessly to a step-down Great Room with a fireplace, & access to the outdoors

    Patricia Bradley Rutledge Properties

    19 Marvin Rd, Wellesley, MA 02482
  • 6 Southgate Rd, Wellesley, MA 02482
    6 Southgate Rd, Wellesley, MA 02482
    6 Southgate Rd, Wellesley, MA 02482
    /40

    $4,895,000

    • 6 Beds
    • 9 Baths
    • 7,500 Sq Ft

    6 Southgate Rd, Wellesley, MA 02482

    Stunning New Construction in one of Wellesley’s most desirable Dana Hall neighborhoods. This sun-splashed home features 7 bedrooms, 6 full bathrooms, and 3 half bathrooms. The home sits majestically on a large, level lot, providing outstanding space for outdoor activities, entertaining, or the addition of a pool. This home checks all the boxes: a custom mudroom, 2 offices, butler's pantry, pantry

    Joseph Fleming JT Fleming & Company

    6 Southgate Rd, Wellesley, MA 02482
  • 12 Winding River Cir, Wellesley, MA 02482
    12 Winding River Cir, Wellesley, MA 02482
    12 Winding River Cir, Wellesley, MA 02482
    /42

    $5,675,000 Open Sat 11:30AM - 1PM

    • 6 Beds
    • 9 Baths
    • 9,036 Sq Ft

    12 Winding River Cir, Wellesley, MA 02482

    Welcome to 12 Winding River Circle. Move right in! This stunning retreat is set on nearly three acres along the picturesque Charles River. Renovated and designed by renowned architect Patrick Ahearn, this exquisite home seamlessly blends timeless elegance with modern luxury. This residence, tucked on a cul-de-sac, offers over 7700 square feet of beautifully designed living space. Sun-filled

    Debi Benoit William Raveis R.E. & Home Services

    12 Winding River Cir, Wellesley, MA 02482
  • 15 Essex Rd, Wellesley Hills, MA 02481
    15 Essex Rd, Wellesley Hills, MA 02481
    15 Essex Rd, Wellesley Hills, MA 02481
    /40

    $4,595,000

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

    15 Essex Rd, Wellesley Hills, MA 02481

    Experience luxury in this exquisite 6-bedroom Colonial in Cliff Estates. Impeccable craftsmanship and high-end upgrades blend elegance with comfort. The open-concept kitchen flows into a cozy family room with custom built-ins, while sophisticated living and dining areas set the stage for refined entertaining. A striking wrap-around mahogany bar extends to the outdoor patio, featuring a saltwater

    Allison David Poirier Coldwell Banker Realty - Wellesley

    15 Essex Rd, Wellesley Hills, MA 02481
  • 99 Old Colony Rd, Wellesley Hills, MA 02481
    99 Old Colony Rd, Wellesley Hills, MA 02481
    99 Old Colony Rd, Wellesley Hills, MA 02481
    /22

    $5,850,000 Open Sat 12PM - 1:30PM

    • 6 Beds
    • 7 Baths
    • 7,287 Sq Ft

    99 Old Colony Rd, Wellesley Hills, MA 02481

    Custom built by high-end builder, this Cliff Estates masterpiece fuses timeless and classic design with the newer systems and finishes found in a young home to create a truly unique offering. Nestled on over a half acre of park like grounds & with wonderful curb appeal, there is over 7200 square feet of luxurious living spaces. Upon entry into the grand foyer, you sense the soaring 10' ceilings,

    The Shulkin Wilk Group Compass

    99 Old Colony Rd, Wellesley Hills, MA 02481
  • 78 Hunnewell St, Wellesley Hills, MA 02481
    78 Hunnewell St, Wellesley Hills, MA 02481
    78 Hunnewell St, Wellesley Hills, MA 02481
    /42

    $2,200,000 Open Sun 1PM - 2:30PM

    • 5 Beds
    • 4.5 Baths
    • 4,043 Sq Ft

    78 Hunnewell St, Wellesley Hills, MA 02481

    Your dream home awaits! This beautiful, 2013-built colonial sits on over half an acre abutting Sudbury Path and offers an expansive, timeless layout with 3 levels of living. The first floor features a dramatic entryway, front-to-back formal living & dining spaces, half bath, and a chef’s kitchen with breakfast nook that opens to a gracious step-down family room with gas fireplace – all

    Fleet Homes Group Keller Williams Realty

    78 Hunnewell St, Wellesley Hills, MA 02481
  • 1 Roberts Rd, Wellesley, MA 02481
    1 Roberts Rd, Wellesley, MA 02481
    1 Roberts Rd, Wellesley, MA 02481
    /29

    $1,395,000

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

    1 Roberts Rd, Wellesley, MA 02481

    Completely renovated beautiful 3 bedroom, 3 full bathroom house! Gorgeous new open kitchen with large island opens to a private patio with firepit great for entertaining. Gracious living room with fireplace, charming den/family/bedroom on the first floor with window seats and full bathroom. New Main bedroom with sky lights and vaulted ceiling, a 2nd bedroom and office/nursey with 2 full

    Allison David Poirier Coldwell Banker Realty - Wellesley

    1 Roberts Rd, Wellesley, MA 02481
  • 10 Bird Hill Ave, Wellesley Hills, MA 02481
    10 Bird Hill Ave, Wellesley Hills, MA 02481
    10 Bird Hill Ave, Wellesley Hills, MA 02481
    /40

    $3,895,000 Open Sun 12PM - 1:30PM

    • 5 Beds
    • 5.5 Baths
    • 5,833 Sq Ft

    10 Bird Hill Ave, Wellesley Hills, MA 02481

    One of 3 exceptional new construction homes by one of Wellesley’s premier builders -Copper Leaf Development. Sited on an ended way in Wellesley Farms, this 5800 square foot 5 bedroom 5/1 bath home has been thoughtfully designed with rich finishes, superb building materials, 9’ ceilings on the first and second floors and a floor plan which works for everyday life and formal entertaining. Grand

    Donahue Maley & Burns Team Compass

    10 Bird Hill Ave, Wellesley Hills, MA 02481
  • 56 Ledgeways St, Wellesley, MA 02481
    56 Ledgeways St, Wellesley, MA 02481
    56 Ledgeways St, Wellesley, MA 02481
    /39

    $5,200,000 Open Sat 1PM - 2:30PM

    • 6 Beds
    • 9 Baths
    • 7,000 Sq Ft

    56 Ledgeways St, Wellesley, MA 02481

    An extraordinary home in Wellesley Farms! A stunning staircase sets the stage for 3 floors of elegant living designed by award winning architect Jan Glysteen and constructed by a premier Wellesley builder .Renovated with incredible attention to detail, custom moldings, wainscoting and coffered ceilings. Amenities include radiant heated floors, heated driveway and patios. Lovely fireplaced living

    Gail Lockberg Berkshire Hathaway HomeServices Town and Country Real Estate

    56 Ledgeways St, Wellesley, MA 02481
  • 29 Denton Rd, Wellesley, MA 02482
    29 Denton Rd, Wellesley, MA 02482
    29 Denton Rd, Wellesley, MA 02482
    /12

    $1,700,000

    • 4 Beds
    • 2.5 Baths
    • 2,956 Sq Ft

    29 Denton Rd, Wellesley, MA 02482

    Nestled in the charming town of Wellesley, Massachusetts, discover the timeless elegance of 29 Denton Road, a single-family residence that presents an exceptional opportunity. This residence stands as a testament to enduring quality and craftsmanship. The generous layout of this home includes four bedrooms, offering ample space for rest and relaxation. Two full bathrooms and one half bathroom are

    Elisabeth LeBlanc Jack Gately Real Estate, LLC

    29 Denton Rd, Wellesley, MA 02482
  • 428 Weston Rd, Wellesley, MA 02482
    428 Weston Rd, Wellesley, MA 02482
    428 Weston Rd, Wellesley, MA 02482
    /30

    $1,599,900 Open Sun 1:30PM - 3PM

    • 5 Beds
    • 3.5 Baths
    • 2,558 Sq Ft

    428 Weston Rd, Wellesley, MA 02482

    Captivating Stone-Front Colonial with Versatile Layout offers a flexible floor plan featuring five spacious bedrooms including a first-floor suite with private full bath ideal for guests, in-laws or a Home Office. The sun filled main level is ideal for entertaining, offering generous spaces filled with natural light. The Kitchen features freshly painted Cabinets (2025) & newer Appliances.

    Rachel Bodner Coldwell Banker Realty - Sudbury

    428 Weston Rd, Wellesley, MA 02482
  • 25 Shaw Rd, Wellesley Hills, MA 02481
    25 Shaw Rd, Wellesley Hills, MA 02481
    25 Shaw Rd, Wellesley Hills, MA 02481
    /31

    $1,999,000

    • 5 Beds
    • 4.5 Baths
    • 4,580 Sq Ft

    25 Shaw Rd, Wellesley Hills, MA 02481

    Welcome to where luxury meets modern living in this stunning new construction home. Designed with a unique transitional aesthetic, this 5-bedroom, 4.5-bathroom residence offers an impeccable blend of timeless elegance and contemporary flair. Step inside to find a spacious open-concept layout, highlighted by a gourmet kitchen featuring high-end appliances, custom cabinetry, and an oversized island

    Vanessa Duguerre Coldwell Banker Realty - Easton

    25 Shaw Rd, Wellesley Hills, MA 02481
  • 7 Garden Rd, Wellesley Hills, MA 02481
    7 Garden Rd, Wellesley Hills, MA 02481
    7 Garden Rd, Wellesley Hills, MA 02481
    /38

    $2,295,000

    • 5 Beds
    • 4.5 Baths
    • 4,655 Sq Ft

    7 Garden Rd, Wellesley Hills, MA 02481

    Situated in coveted Wellesley Farms/Cliff Estates, this renovated, energy-efficient home sits back from the street with new sound-proof windows and 2024 systems. Airy kitchen with soaring ceiling connects seamlessly to the family and dining rooms, perfect for gatherings. The great room features custom built-ins and a wood-burning fireplace; the first floor also includes a chic powder room and a

    Rahel Choi eXp Realty

    7 Garden Rd, Wellesley Hills, MA 02481
  • 33 Royalston Rd, Wellesley, MA 02481
    33 Royalston Rd, Wellesley, MA 02481
    33 Royalston Rd, Wellesley, MA 02481
    /42

    $5,879,995

    • 6 Beds
    • 7.5 Baths
    • 9,494 Sq Ft

    33 Royalston Rd, Wellesley, MA 02481

    Welcome to 33 Royalston Road! A rare standout in the neighborhood, this newly constructed home offers four levels of luxury living with top-tier finishes and flexible spaces. The main floor features two dramatic living areas: a fireplace accompanied family room and a stunning great room with cathedral ceilings, custom trim, oversized windows, a wet bar, and access to a covered patio. The chef’s

    George Sariego Boston One Realty Group Inc

    33 Royalston Rd, Wellesley, MA 02481

Showing Results 1 - 40, Page 1 of 2

Massachusetts Norfolk County Wellesley

Houses for Sale in Wellesley, MA

Why Live in Wellesley

Wellesley, Massachusetts, is a peaceful academic town located approximately 15 miles from Boston. Known for its upscale residential community, Wellesley features stately homes, including spacious colonial-inspired properties, ranch-style homes, Cape Cods, and raised ranches. The town's housing inventory includes single-family homes, townhouses, and condominiums, with well-landscaped yards ranging from a quarter-acre to 1 acre in size. The town is home to Wellesley College and Babson College, and boasts one of the best public school systems in the state, including Wellesley Public Schools, Wellesley High School, and the prestigious Dana Hall School. Residents enjoy nearly 50 miles of trails, sports fields, playgrounds, and parks, with popular spots like Warren Park and Morses Pond offering recreational activities such as boating, fishing, and swimming. Wellesley Square serves as the main shopping district, featuring chain grocery stores, local restaurants, cafes, boutiques, and businesses. The town is accessible via Massachusetts State Route 9 and Interstate 95, with three MBTA commuter rail stations providing rail service to Boston. Logan International Airport is approximately 20 miles east. Community celebrations include seasonal festivals and Wellesley’s Wonderful Weekend, featuring a Veterans parade, fireworks, and various family-friendly activities. While violent crimes decreased in 2023, property crimes saw a slight increase compared to 2022.

Learn more about living in Wellesley

Home Trends in Wellesley, MA

On average, homes in Wellesley, MA sell after 27 days on the market compared to the national average of 52 days. The median sale price for homes in Wellesley, MA over the last 12 months is $1,995,000, up 11% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$1,995,000
Median Single Family Sale Price
$2,150,000
Median Townhouse Sale Price
$1,599,900
Median 2 Bedroom Sale Price
$1,457,750
Median 1 Bedroom Sale Price
$1,125,000
Average Price Per Sq Ft
$752
Number of Homes for Sale
29
Last 12 months Home Sales
127
Months of Supply
2.70
Median List Price
$1,950,000
Median Change From 1st List Price
1%
Median Home Sale Price YoY Change
11%
How to Buy a Home How to Finance a Home How to Sell a Home

In Wellesley, there are currently 63 houses for sale, offering an array of options for potential buyers. With houses priced between $725,000 to $9,250,000, there's a range to accomodate every budget. As of September, 2025 the median home price in Wellesley is $1,950,000, while the average sale price is $2,155,445, offering insights into the local housing market. On average, houses spend 27 days listed before being sold. Whether you're searching for a single-family residence, exploring single-family detached houses for sale, or considering new construction houses for sale, there are options to cater to different lifestyles. Explore the listings and houses for sale in Wellesley, MA and find the perfect place to call home.

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2025 CoStar Group