55

Wellesley, MA Homes for Sale

Section Image
  • 99 Old Colony Rd, Wellesley Hills, MA 02481
    99 Old Colony Rd, Wellesley Hills, MA 02481
    99 Old Colony Rd, Wellesley Hills, MA 02481
    /24

    $5,294,500 Open Sat 12:30PM - 2PM

    • 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
  • 12 Winding River Cir, Wellesley, MA 02482
    12 Winding River Cir, Wellesley, MA 02482
    12 Winding River Cir, Wellesley, MA 02482
    /40

    $5,250,000

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

    12 Winding River Cir, Wellesley, MA 02482

    Exceptional property on the Charles River! 2.89 acres of manicured lawn rolls down to the river giving you unobstructed views & private use of a nature lover's paradise. Gorgeous stone patios, multiple decks, & sun-filled rooms w/French Doors are all designed to maximize your enjoyment of this incredible retreat. Privately nestled on a quiet cul-de-sac, this stunning Cape is beautiful in all

    Betsy Kessler Rutledge Properties

    12 Winding River Cir, Wellesley, MA 02482
  • 78 Suffolk Rd, Wellesley Hills, MA 02481
    78 Suffolk Rd, Wellesley Hills, MA 02481
    /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
  • 8 Oakdale Ave, Wellesley, MA 02482
    8 Oakdale Ave, Wellesley, MA 02482
    8 Oakdale Ave, Wellesley, MA 02482
    /34

    $3,425,000

    • 5 Beds
    • 6 Baths
    • 5,073 Sq Ft

    8 Oakdale Ave, Wellesley, MA 02482

    Experience the epitome of luxury in this stunning new Colonial masterpiece in Wellesley, nestled on a serene dead-end street. With 5 bedrooms and 5 baths sprawled over 5,000 sq. ft., every inch exudes elegance. Experience gleaming hardwood floors beneath soaring 9’ ceilings, embraced by sunlit spaces. The first floor boasts refined living and dining areas, a chef’s eat-in kitchen with bespoke

    Donahue Maley & Burns Team Compass

    8 Oakdale Ave, Wellesley, MA 02482
  • 151 Oakland St, Wellesley Hills, MA 02481
    151 Oakland St, Wellesley Hills, MA 02481
    151 Oakland St, Wellesley Hills, MA 02481
    /42

    $4,650,000

    • 6 Beds
    • 5 Baths
    • 6,990 Sq Ft

    151 Oakland St, Wellesley Hills, MA 02481

    A rare Wellesley gem set on 1.15 acres, overlooking the 15th hole & 16th tee of Wellesley Country Club with sweeping scenic golf course views. Fully renovated in 2022, this distinguished home blends historic character with refined luxury, featuring wide pine floors, 6 fireplaces, and walls of windows overlooking the greens. Gracious living spaces include an inviting great room, sophisticated

    Beth Dickerson Gibson Sotheby's International Realty

    151 Oakland St, Wellesley Hills, MA 02481
  • 241 Lowell Rd, Wellesley Hills, MA 02481
    241 Lowell Rd, Wellesley Hills, MA 02481
    241 Lowell Rd, Wellesley Hills, MA 02481
    /42

    $3,950,000 Open Fri 3:30PM - 6:30PM

    • 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
  • 22 Cranmore Rd, Wellesley Hills, MA 02481
    22 Cranmore Rd, Wellesley Hills, MA 02481
    22 Cranmore Rd, Wellesley Hills, MA 02481
    /35

    $3,495,000

    • 5 Beds
    • 4.5 Baths
    • 5,738 Sq Ft

    22 Cranmore Rd, Wellesley Hills, MA 02481

    Experience modern luxury in this stunning 5,700 sqft home in the coveted Cliff Estates. Designed with contemporary elegance, the open-concept main level is ideal for everyday living and entertaining, featuring a sun-filled gourmet kitchen that flows seamlessly into spacious dining and living areas and a welcoming, vaulted family room. The first-floor primary suite offers a private retreat with

    The Shulkin Wilk Group Compass

    22 Cranmore Rd, Wellesley Hills, MA 02481
  • 38 Parker Rd, Wellesley, MA 02482
    38 Parker Rd, Wellesley, MA 02482
    38 Parker Rd, Wellesley, MA 02482
    /42

    $3,395,000

    • 5 Beds
    • 4.5 Baths
    • 4,416 Sq Ft

    38 Parker Rd, Wellesley, MA 02482

    Incredible new construction opportunity in one of Wellesley’s most sought-after neighborhoods, ideally located within walking distance to the newly built John D. Hardy Elementary School and nearby Perrin Park. This exceptional home offers a fabulous floor plan featuring soaring ceilings, exquisite millwork, abundant natural light, and designer fixtures and finishes throughout. The first floor

    William Natoli Compass

    38 Parker Rd, Wellesley, MA 02482
  • 85 Grove St Unit 306, Wellesley, MA 02482
    85 Grove St Unit 306, Wellesley, MA 02482
    85 Grove St Unit 306, Wellesley, MA 02482
    /24

    $1,350,000

    • 2 Beds
    • 2 Baths
    • 1,528 Sq Ft

    85 Grove St Unit 306, Wellesley, MA 02482

    Elegant 2bed/2bath unit is now available at Wellesley Green! This thoughtfully designed home is filled with natural light and offers comfortable living and dining spaces, ideal for both everyday living and entertaining. The efficiently designed kitchen features newly replaced appliances. A stylish dining area flows seamlessly into the living room, where large balcony windows frame lovely,

    Meghan Sutherland MGS Group Real Estate LTD - Wellesley

    85 Grove St Unit 306, Wellesley, MA 02482
  • 14 Greylock Rd, Wellesley Hills, MA 02481
    14 Greylock Rd, Wellesley Hills, MA 02481
    14 Greylock Rd, Wellesley Hills, MA 02481
    /24

    $7,995,000

    • 6 Beds
    • 9 Baths
    • 10,197 Sq Ft

    14 Greylock Rd, Wellesley Hills, MA 02481

    Exceptional Peirce Estates residence offering over 10,000 sq ft of refined living on a level 0.85-acre lot with room for a pool. Renovated and expanded in 2006–07, the home features 16 rooms, including 6 ensuite bedrooms and 3 half baths. The expansive chef’s kitchen with dual refrigerators and dishwashers, walk-in pantry and breakfast area opens to a sun-filled family room with double-sided

    Bobby Morgenstern Gibson Sotheby's International Realty

    14 Greylock Rd, Wellesley Hills, MA 02481
  • 16 Oak St, Wellesley, MA 02482
    16 Oak St, Wellesley, MA 02482
    16 Oak St, Wellesley, MA 02482
    /33

    $2,695,000

    • 5 Beds
    • 5 Baths
    • 4,200 Sq Ft

    16 Oak St, Wellesley, MA 02482

    Sun-splashed historic renovation of an in-town Colonial offering 5 bedrooms, 3 full baths, and 2 half baths. This stunning home blends timeless character with modern comfort, featuring high ceilings, spacious living areas, and a finished walkout basement ideal for a home office, gym, or entertaining. The chef’s kitchen includes a 72-inch fridge/freezer, a large island, a pantry, and opens to a

    Joseph Fleming JT Fleming & Company

    16 Oak St, Wellesley, MA 02482
  • 32 Lantern Ln, Wellesley Hills, MA 02481
    32 Lantern Ln, Wellesley Hills, MA 02481
    32 Lantern Ln, Wellesley Hills, MA 02481
    /42

    $2,349,999 Open Sat 11:30AM - 1:30PM

    • 5 Beds
    • 4.5 Baths
    • 4,404 Sq Ft

    32 Lantern Ln, Wellesley Hills, MA 02481

    A stunning 2022 custom built home offering over 4,400 square feet designed from the ground up for exceptional interior quiet. Step inside and the outside world falls away.The open layout features nine and a half foot ceilings, expansive windows, and a chef's kitchen with built-in refrigerator, double ovens, commercial cooktop, farmhouse sink, and oversized island. The living room includes a

    Jay Terada Coldwell Banker Realty - Brookline

    32 Lantern Ln, Wellesley Hills, MA 02481
  • 200 Pond Rd, Wellesley, MA 02482
    200 Pond Rd, Wellesley, MA 02482
    200 Pond Rd, Wellesley, MA 02482
    /30

    $7,995,000

    • 8 Beds
    • 9 Baths
    • 9,662 Sq Ft

    200 Pond Rd, Wellesley, MA 02482

    Presenting a spectacular multi-acre estate set behind a private entry in Wellesley. This stately Georgian Colonial is the centerpiece of the compound on a scenic road and is surrounded by a parklike setting that couples luxury with sophistication. The stately exterior is captivating with stunning architectural detail. Inside the grand home boasts a two story foyer with a sweeping bridal

    Meghan Sutherland MGS Group Real Estate LTD - Wellesley

    200 Pond Rd, Wellesley, MA 02482
  • 31 College Rd, Wellesley, MA 02482
    31 College Rd, Wellesley, MA 02482
    31 College Rd, Wellesley, MA 02482
    /36

    $2,395,000

    • 5 Beds
    • 3.5 Baths
    • 3,398 Sq Ft

    31 College Rd, Wellesley, MA 02482

    5 bedroom home on Morses Pond with the most incredible water views. Swim, paddle board, kayak or fish from your own backyard. Large open kitchen family room with full picture windows offering stunning views of the pond. Kitchen with stainless appliances and large island. Dining room/sunroom with access to deck with more water views. Living room with fireplace and built-ins. First floor den. Main

    Melissa Dailey Coldwell Banker Realty - Wellesley

    31 College Rd, Wellesley, MA 02482
  • 90 Elmwood Rd, Wellesley Hills, MA 02481
    90 Elmwood Rd, Wellesley Hills, MA 02481
    90 Elmwood Rd, Wellesley Hills, MA 02481
    /37

    $1,875,000 Open Fri 4PM - 5:30PM

    • 4 Beds
    • 3.5 Baths
    • 3,428 Sq Ft

    90 Elmwood Rd, Wellesley Hills, MA 02481

    In a wonderful Bates School neighborhood, step inside & discover this thoughtfully expanded, well designed home w/ generous rooms, great flow, & exceptional living space. Versatile first-floor primary suite boasts an updated, stylish bath, great closet space & bonus room for exercise, nursery or study. Three generously sized second floor bedrooms accommodate family & guests. Sun-drenched living

    Petrone-Hunter Realty Group Coldwell Banker Realty - Wellesley

    90 Elmwood Rd, Wellesley Hills, MA 02481
  • 16 Stearns Rd Unit 101, Wellesley, MA 02482
    16 Stearns Rd Unit 101, Wellesley, MA 02482
    16 Stearns Rd Unit 101, Wellesley, MA 02482
    /29

    $1,699,000

    • 2 Beds
    • 2.5 Baths
    • 1,788 Sq Ft

    16 Stearns Rd Unit 101, Wellesley, MA 02482

    Now ready for occupancy! Masterfully crafted, the 24 unit condominiums at The Albion feature luxury living spaces w/ open floor plans, high end finishes & bordering green spaces. The Albion is the ultimate mix of contemporary design, modern amenities & is set in a prime location near Linden Square in Wellesley. This 2 bedroom, 2.5 bathroom, w den, features 9 foot high ceilings, hardwood floors,

    Bartlett Albion Group Hammond Residential Real Estate

    16 Stearns Rd Unit 101, Wellesley, MA 02482
  • 365 Worcester St, Wellesley, MA 02481
    365 Worcester St, Wellesley, MA 02481
    365 Worcester St, Wellesley, MA 02481
    /37

    $2,899,000 Open Sun 12PM - 1:15PM

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

    365 Worcester St, Wellesley, MA 02481

    Welcome to a luxurious,expansive 2026 new construction-a classic brick-front New England colonial in a 3 home subdivision! A stunning double storey staircase leads you to a family room full of windows & natural sunlight & a private backyard. Designed to entertain guests-a large Chef's kitchen with custom built cabinets, quartz waterfall island, induction cooking, S/S high end Thermador

    Shahani Real Estate Team Compass

    365 Worcester St, Wellesley, MA 02481
  • 121 Livingston Rd, Wellesley, MA 02482
    121 Livingston Rd, Wellesley, MA 02482
    121 Livingston Rd, Wellesley, MA 02482
    /37

    $6,995,000 Open Sat 11:30AM - 1PM

    • 6 Beds
    • 10 Baths
    • 10,090 Sq Ft

    121 Livingston Rd, Wellesley, MA 02482

    Set on nearly two acres with direct access to the Charles River and surrounded by conservation land, this custom-built Colonial offers a rare combination of privacy, scale, and waterfront living in Wellesley’s coveted Dana Hall neighborhood. Thoughtfully designed and crafted, the home delivers enduring quality and a lifestyle that is increasingly rare.A gracious foyer introduces formal living and

    Ying Sun Compass

    121 Livingston Rd, Wellesley, MA 02482
  • 45 White Oak Rd, Wellesley Hills, MA 02481
    45 White Oak Rd, Wellesley Hills, MA 02481
    45 White Oak Rd, Wellesley Hills, MA 02481
    /38

    $12,250,000

    • 5 Beds
    • 5.5 Baths
    • 7,200 Sq Ft

    45 White Oak Rd, Wellesley Hills, MA 02481

    A one-of-one, architect-led residence pairing timeless New England architecture with modern high-performance construction. This home was built as a fully realized home, not a speculative project. Every decision from proportion to materials, systems, and detailing was made to enhance daily living, long-term comfort, and architectural clarity. Behind its masonry exterior is a rigorously executed

    Megann Schiffer Northeast Development & Investment, Inc.

    45 White Oak Rd, Wellesley Hills, MA 02481
  • 6 Boulder Brook Rd, Wellesley Hills, MA 02481
    6 Boulder Brook Rd, Wellesley Hills, MA 02481
    6 Boulder Brook Rd, Wellesley Hills, MA 02481
    /34

    $1,995,000 Open Sat 1PM - 2:30PM

    • 4 Beds
    • 3.5 Baths
    • 2,813 Sq Ft

    6 Boulder Brook Rd, Wellesley Hills, MA 02481

    Beautifully expanded Cape set in the highly sought-after Bates neighborhood, offering a perfect blend of comfort and style. The chef’s kitchen opens seamlessly to a spacious family room featuring tray ceilings, custom built-in bookcases, a granite bar with wine refrigerator, and a gas fireplace—ideal for everyday living and entertaining. A sun-filled dining room and inviting living room with

    Jennifer Madden Coldwell Banker Realty - Wellesley

    6 Boulder Brook Rd, Wellesley Hills, MA 02481
  • 16 Stearns Rd Unit 106, Wellesley, MA 02482
    16 Stearns Rd Unit 106, Wellesley, MA 02482
    16 Stearns Rd Unit 106, Wellesley, MA 02482
    /12

    $1,348,050

    • 2 Beds
    • 2.5 Baths
    • 1,419 Sq Ft

    16 Stearns Rd Unit 106, Wellesley, MA 02482

    New Construction! Stunning 2-bedroom, 2.5-bath residence featuring soaring 9' ceilings and beautiful open views overlooking Sprague Field. The open-concept floor plan showcases a high-end chef’s kitchen with center island, premium finishes, and all the bells and whistles—perfect for everyday living and entertaining. The warm and inviting living room is highlighted by a cozy fireplace. The

    Bartlett Albion Group Hammond Residential Real Estate

    16 Stearns Rd Unit 106, Wellesley, MA 02482
  • 25 Washburn Ave, Wellesley Hills, MA 02481
    25 Washburn Ave, Wellesley Hills, MA 02481
    25 Washburn Ave, Wellesley Hills, MA 02481
    /35

    $2,495,000 Open Fri 4PM - 5:30PM

    • 6 Beds
    • 4 Baths
    • 3,694 Sq Ft

    25 Washburn Ave, Wellesley Hills, MA 02481

    Charming Colonial in Wellesley’s beloved Poets Corner area, seamlessly blends character with modern updates. Originally built in 1905, thoughtfully expanded and renovated since, offering 6 bedrooms, 4 full bathrooms, with great flow and versatile layout. Enclosed front porch leads to formal livingroom with stunning wood floors. Bright kitchen with FisherPaykel double ovens, Subzero, counter

    Benna Lynch Rondini Charlesgate Realty Group LLC

    25 Washburn Ave, Wellesley Hills, MA 02481
  • 200 Cliff Rd, Wellesley Hills, MA 02481
    200 Cliff Rd, Wellesley Hills, MA 02481
    200 Cliff Rd, Wellesley Hills, MA 02481
    /41

    $5,350,000

    • 7 Beds
    • 7 Baths
    • 7,262 Sq Ft

    200 Cliff Rd, Wellesley Hills, MA 02481

    Much admired 7 bedroom, 7000+sf estate home on an acre of manicured lawns on famed Cliff Road. Built and re designed by two of New England’s most acclaimed architects, this home boasts the grandeur of stately proportions and sumptuous millwork with a newly renovated and superbly equipped chef’s Kitchen and butler’s pantry with adjacent family room. A banquet sized dining room and gracious living

    Donahue Maley & Burns Team Compass

    200 Cliff Rd, Wellesley Hills, MA 02481
  • 12 Bird Hill Ave, Wellesley, MA 02481
    12 Bird Hill Ave, Wellesley, MA 02481
    12 Bird Hill Ave, Wellesley, MA 02481
    /37

    $3,895,000

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

    12 Bird Hill Ave, Wellesley, 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

    12 Bird Hill Ave, Wellesley, MA 02481
  • 43 Bristol Rd, Wellesley Hills, MA 02481
    43 Bristol Rd, Wellesley Hills, MA 02481
    43 Bristol Rd, Wellesley Hills, MA 02481
    /42

    $5,450,000

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

    43 Bristol Rd, Wellesley Hills, MA 02481

    Stately brick Colonial in sought after Cliff Estates is beautifully sited on a magnificent private corner lot. The exquisite two story foyer welcomes you into this spectacular property. Elegant living room with fireplace, built-ins and grand dining room with floor to ceiling windows and butler's pantry are perfectly suited for entertaining. Bright chef's kitchen with oversized center island,

    Debi Benoit William Raveis R.E. & Home Services

    43 Bristol Rd, Wellesley Hills, MA 02481
  • 84 Royalston Rd, Wellesley Hills, MA 02481
    84 Royalston Rd, Wellesley Hills, MA 02481
    84 Royalston Rd, Wellesley Hills, MA 02481
    /42

    $3,874,000

    • 6 Beds
    • 5.5 Baths
    • 6,406 Sq Ft

    84 Royalston Rd, Wellesley Hills, MA 02481

    A rare offering in Wellesley, located in Cliff estates—this nearly one-acre private, park-like property features quality outdoor living and an elegant brick-front colonial. Royalston Road is a very exclusive and private location. Considered by many as one of the best streets and location in the town of Wellesley. Professionally landscaped grounds frame a spacious patio, sweeping lawn, and

    William Montero Gibson Sotheby's International Realty

    84 Royalston Rd, Wellesley Hills, MA 02481
  • 33 Boulder Rd, Wellesley, MA 02481
    33 Boulder Rd, Wellesley, MA 02481
    33 Boulder Rd, Wellesley, MA 02481
    /6

    $1,995,000

    • Land
    • 0.51 Acre
    • $3,911,765 per Acre

    33 Boulder Rd, Wellesley, MA 02481

    OPEN BUILDING LOT in exclusive Wellesley Farms! Bring your dreams and ideas and get started on designing and building your custom home in one of the finest neighborhoods in Wellesley. Conforming, flat and fenced 22,388 sq ft lot with no existing structure. Town water, sewer, electricity and gas at street. 20,000 SF zoning, 170' of frontage. Geotechinical Data Report completed. SHOVEL READY!

    Christine Lawrence Rutledge Properties

    33 Boulder Rd, Wellesley, MA 02481
  • 16 Stearns Rd Unit 103, Wellesley, MA 02482
    16 Stearns Rd Unit 103, Wellesley, MA 02482
    16 Stearns Rd Unit 103, Wellesley, MA 02482
    /19

    $1,523,800

    • 2 Beds
    • 2.5 Baths
    • 1,604 Sq Ft

    16 Stearns Rd Unit 103, Wellesley, MA 02482

    New Construction! Stunning 2-bedroom, 2.5-bath condo featuring an open floor plan and soaring 9' ceilings. Enjoy beautiful views overlooking Sprague Field in this boutique 24-unit association. Each unit includes one garage parking space, plus ample guest parking.The top-of-the-line kitchen boasts high-end appliances, a center island, and sleek finishes—perfect for cooking and entertaining. The

    Bartlett Albion Group Hammond Residential Real Estate

    16 Stearns Rd Unit 103, Wellesley, MA 02482
  • 16 Sunnyside Ave, Wellesley, MA 02482
    16 Sunnyside Ave, Wellesley, MA 02482
    16 Sunnyside Ave, Wellesley, MA 02482
    /27

    $1,375,000

    • 3 Beds
    • 1.5 Baths
    • 1,743 Sq Ft

    16 Sunnyside Ave, Wellesley, MA 02482

    Welcome to this lovingly maintained 3 BR home on a quiet cul-de-sac in Wellesley. The first floor offers a formal living room w/wood burning fireplace, formal dining room and a sun-splashed FR with vaulted ceiling, gas FP, AC and access to outdoor deck. The kitchen has updated, granite countertops, SS appliances and dining space. 1/2 BA completes the first floor. The 2nd floor has three bedrooms

    Susan Gear Coldwell Banker Realty - Wellesley

    16 Sunnyside Ave, Wellesley, MA 02482
  • 222 Grove St, Wellesley, MA 02482
    222 Grove St, Wellesley, MA 02482
    222 Grove St, Wellesley, MA 02482
    /42

    $7,495,000

    • 6 Beds
    • 8 Baths
    • 8,093 Sq Ft

    222 Grove St, Wellesley, MA 02482

    Discover exceptional elegance & privacy in Wellesley’s coveted Dana Hall neighborhood. Set on over an acre in one of the town’s most sought-after locations it offers the perfect balance of privacy & convenience. Designed by a renowned local architect, this stunning new home blends sophisticated design with modern comfort, creating a serene retreat moments from town. The main floor boasts an open,

    Steve & Nicole Connolly Group Coldwell Banker Realty - Wellesley

    222 Grove St, Wellesley, MA 02482
  • 148 Weston Rd Unit 208, Wellesley, MA 02482
    148 Weston Rd Unit 208, Wellesley, MA 02482
    148 Weston Rd Unit 208, Wellesley, MA 02482
    /29

    $3,375,000

    • 2 Beds
    • 2.5 Baths
    • 2,270 Sq Ft

    148 Weston Rd Unit 208, Wellesley, MA 02482

    Experience unparalleled luxury living at The Bristol in the heart of Wellesley. 23 unit condo community in concierge building designed for buyers seeking maintenance-free living and every modern convenience. Corner unit boasts 9 ft ceilings and white oak floors. Seating for four at waterfall island. Seamless walnut and glass cabinetry and handmade subway tile backsplash creates a crisp,

    The Bauman Group Gibson Sotheby's International Realty

    148 Weston Rd Unit 208, Wellesley, MA 02482
  • 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

    • 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
  • 26B Pleasant St Unit B, Wellesley, MA 02482
    26B Pleasant St Unit B, Wellesley, MA 02482
    26B Pleasant St Unit B, Wellesley, MA 02482
    /21

    $1,129,000

    • 2 Beds
    • 2 Baths
    • 1,739 Sq Ft

    26B Pleasant St Unit B, Wellesley, MA 02482

    This bright end-unit townhouse offers four levels of comfortable living in a prime location, just a short stroll to Linden Square's shops, dining, and the train to Boston The home features hardwood floors throughout, central AC and hearing, two bedrooms, two bathrooms and a versatile bonus room on the third floor, The modern grante kitchen flows into a dining are that opens to a private patio,

    Zhen Guo Coldwell Banker Realty - Brookline

    26B Pleasant St Unit B, Wellesley, MA 02482
  • 20 Parker Rd, Wellesley, MA 02482
    20 Parker Rd, Wellesley, MA 02482
    20 Parker Rd, Wellesley, MA 02482
    /38

    $2,995,000

    • 6 Beds
    • 3.5 Baths
    • 4,393 Sq Ft

    20 Parker Rd, Wellesley, MA 02482

    Exceptional Colonial blends timeless architecture w modern refinement in one of Wellesley’s most coveted neighborhoods. Offering 6 generously sized bedrooms this home is thoughtfully designed for today’s lifestyle. Gracious foyer leads to elegant fireplaced living room & effortlessly connects to the sophisticated dining room w gleaming hardwood floors throughout. Gourmet kitchen w stainless steel

    George Sarkis Douglas Elliman Real Estate - The Sarkis Team

    20 Parker Rd, Wellesley, MA 02482
  • 18 Eaton Ct, Wellesley Hills, MA 02481
    18 Eaton Ct, Wellesley Hills, MA 02481
    18 Eaton Ct, Wellesley Hills, MA 02481
    /27

    $1,499,000

    • 5 Beds
    • 2.5 Baths
    • 2,728 Sq Ft

    18 Eaton Ct, Wellesley Hills, MA 02481

    This attached single-family townhome combines the best of in-town living with the privacy and independence of a single-family home. Tastefully renovated throughout, it preserves period character and millwork while introducing today’s modern comforts, including tall ceilings, light-filled rooms, Carrara marble baths, central air, and 200 AMP electrical service. The spacious and flexible floor plan

    Susan Lyman Douglas Elliman Real Estate - Wellesley

    18 Eaton Ct, Wellesley Hills, 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 Open Sat 1PM - 3PM

    • 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
  • 560 Worcester St, Wellesley Hills, MA 02481
    560 Worcester St, Wellesley Hills, MA 02481
    560 Worcester St, Wellesley Hills, MA 02481
    /42

    $1,599,000 Open Sat 1PM - 2:30PM

    • 4 Beds
    • 2.5 Baths
    • 1,716 Sq Ft

    560 Worcester St, Wellesley Hills, MA 02481

    Experience the pinnacle of Wellesley Hills living at 560 Worcester St, a distinguished location in the highly sought-after community of Wellesley. This classic center entrance colonial is sun drenched and updated throughout, offering a premier location with exceptional visibility and accessibility. Situated along one of the town’s primary streets and walkable to schools, parks, library, post

    Team ROVI Real Broker MA, LLC

    560 Worcester St, Wellesley Hills, MA 02481
  • 170 Benvenue St, Wellesley, MA 02482
    170 Benvenue St, Wellesley, MA 02482
    170 Benvenue St, Wellesley, MA 02482
    /31

    $2,195,000 Open Sat 12PM - 2PM

    • 5 Beds
    • 3 Baths
    • 2,465 Sq Ft

    170 Benvenue St, Wellesley, MA 02482

    Beautifully updated and move-in ready, this 5 bedroom Cape sits on nearly 1/2 acre in Wellesley’s desirable Dana Hall neighborhood. The 1st floor features a fireplace anchored living room with an oversized picture window that fills the space with natural light. From there, the layout flows into a thoughtfully updated kitchen with leathered quartzite countertops, a waterfall island, and new Bosch

    Sneha Patel Gibson Sotheby's International Realty

    170 Benvenue St, Wellesley, MA 02482
  • 23 Pilgrim Rd, Wellesley Hills, MA 02481
    23 Pilgrim Rd, Wellesley Hills, MA 02481
    23 Pilgrim Rd, Wellesley Hills, MA 02481
    /30

    $2,795,000

    • 4 Beds
    • 3.5 Baths
    • 4,102 Sq Ft

    23 Pilgrim Rd, Wellesley Hills, MA 02481

    New Construction tucked away in the extremely popular Bates School neighborhood! Premium luxury finishes and high ceilings throughout. Chef’s kitchen offers Thermador appliances, quartz counters, huge center island & custom cabinetry, opening to a bright family room with fireplace. 2nd level is highlighted by the primary suite w/spa-like bath & walk-in closet. Lower level features a large flex

    Kathy Kelley Berkshire Hathaway HomeServices Town and Country Real Estate

    23 Pilgrim Rd, Wellesley Hills, MA 02481
  • 40 Kimlo Rd, Wellesley, MA 02481
    40 Kimlo Rd, Wellesley, MA 02481
    40 Kimlo Rd, Wellesley, MA 02481
    /37

    $2,000,000 Open Sat 1:30PM - 3PM

    • 4 Beds
    • 2.5 Baths
    • 2,896 Sq Ft

    40 Kimlo Rd, Wellesley, MA 02481

    Presenting this extraordinary, beautifully updated 1800s modern farmhouse in highly convenient Wellesley Hills location. Truly unique & rich in character, this home features high ceilings, lovely appointments, & a wonderful sense of connection throughout. A welcoming front porch & foyer open to beautiful living spaces, including a sun-filled family room directly off the kitchen, perfect for

    Petrone-Hunter Realty Group Coldwell Banker Realty - Wellesley

    40 Kimlo Rd, Wellesley, MA 02481

Showing Results 1 - 40, Page 1 of 2

Massachusetts Norfolk County Wellesley

Real Estate & Homes 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

Frequently Asked Questions

What is the average home price in Wellesley, MA?
Homes for sale in Wellesley, MA have an average home price of $2,272,695.
How many homes have sold over the last 12 months in Wellesley, MA?
91 homes have sold in Wellesley, MA over the last 12 months.
Is Wellesley, MA a safe city?
In general, the safest neighborhoods in Wellesley, MA with lower crime scores are Wellesley Square, Dana Hall, Wellesley Farms, Cliff Estates and Wellesley Hills.
What are the most popular zip codes in Wellesley, MA?
The most popular zip codes in Wellesley, MA include 02481, 02482, 02492, 02494 and 02493.
What are the most popular neighborhoods in Wellesley, MA?
The most popular neighborhoods in Wellesley, MA with the most homes for sale are Wellesley Square, Dana Hall, Wellesley Farms, Cliff Estates and Wellesley Hills.
How much do you need to make to afford a house in Wellesley?
The median home price in Wellesley is $1,949,000. If you put a 20% down payment of $389,800 and had a 30-year fixed mortgage with an interest rate of 6%, your estimated principal and interest payment would be $9,350 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $401K a year to afford the median home price in Wellesley. Learn how much home you can afford with our Home Affordability Calculator.
How are the schools in Wellesley, MA?
Wellesley, MA has highly rated public and private schools. Some of the best schools in Wellesley based on Niche Grades are Country Elementary School, Dana Hall School and Dover-Sherborn Regional High School. The neighborhoods in Wellesley with the highest rated schools are Wellesley Square, Dana Hall and Wellesley Farms. Browse all the schools in Wellesley, MA to learn more.

Home Trends in Wellesley, MA

On average, homes in Wellesley, MA sell after 30 days on the market compared to the national average of 54 days. The median sale price for homes in Wellesley, MA over the last 12 months is $1,960,000, up 1% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$1,960,000
Median Single Family Sale Price
$2,364,500
Median Townhouse Sale Price
$1,129,000
Median 2 Bedroom Sale Price
$1,345,000
Median 1 Bedroom Sale Price
$1,285,000
Average Price Per Sq Ft
$787
Number of Homes for Sale
7
Last 12 months Home Sales
91
Months of Supply
0.90
Median List Price
$1,949,000
Median Change From 1st List Price
2%
Median Home Sale Price YoY Change
1%
How to Buy a Home How to Finance a Home How to Sell a 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 © 2026 CoStar Group