Wellesley, MA Homes

/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
/12
$4,400 total monthly price
- 3 Beds
- 1.5 Baths
- 1,625 Sq Ft
- Condo for Rent
22 Cleveland Rd Unit 1, Wellesley, MA 02481

Unit FeaturesBalcony Dining Room Dishwasher Disposal Eat-in Kitchen Fireplace Granite Counter Tops Hardwood Floors Laundry in Unit Stainless Steel Appliance(s)

22 Cleveland Rd Unit 1, Wellesley, MA 02481
/37
$5,400,000 Sold Aug 11, 2025
- 7,817 Sq Ft
- $691/SF
- 42 Days On Market
- 6 Beds
- 7 Baths
- Built 1925
15 Sumner Rd, Wellesley Hills, MA 02481

Rarely available colonial w/ immaculate grounds in prestigious Country Club location! Incredible renovation by esteemed architect, interior designer & builder featured in Traditional Home Magazine. Over 7800 sq ft of finished space in this 6 bedroom home on 4 floors. Elegant crown moulding throughout. High end plumbing fixtures, door & cabinet hardware, cabinetry, lighting & finishes gives this

Melissa Dailey Coldwell Banker Realty - Wellesley

15 Sumner Rd, Wellesley Hills, MA 02481

/32
Est $1,840,339 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 2,956 Sq Ft
25 Upson Rd, Wellesley, MA 02482

25 Upson Rd, Wellesley, MA 02482

/37
$1,995,000
- 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
/15
$5,400 per month plus fees
- 4 Beds
- 2.5 Baths
- 1,572 Sq Ft
- House for Rent
46 Cleveland Rd Unit 1, Wellesley Hills, MA 02481

Desirable Bates School district. Lovely classic Colonial home with updated kitchen with granite counters and high end appliances, living room with fireplace, study, formal dining room with built in cabinet. Gleaming hardwood floors, fenced level yard with patio for entertaining.

Fabiola Perry Coldwell Banker Realty - Wellesley

46 Cleveland Rd Unit 1, Wellesley Hills, MA 02481
/42
$1,400,000 Sold Aug 08, 2025
- 2,936 Sq Ft
- $477/SF
- 17 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2016
106 Edgemoor Ave, Wellesley, MA 02482

This beautiful 2016 farmhouse colonial blends timeless charm with contemporary luxury. Casually elegant, it features an open-concept, eat-in chef’s kitchen with an oversized quartz island, high-end stainless steel appliances and hardwood floors throughout—perfect for everyday living. The bright and stylish living room with a fireplace is filled with natural light while the dining area is

Debi Benoit William Raveis R.E. & Home Services

106 Edgemoor Ave, Wellesley, MA 02482

/37
Est $1,490,005 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 1,914 Sq Ft
7 Bacon St, Wellesley, MA 02482

7 Bacon St, 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
/23
$4,950 per month plus fees
- 3 Beds
- 3 Baths
- 2,100 Sq Ft
- House for Rent
116 Manor Ave, Wellesley, MA 02482

This spacious bright RENOVATED home is 2100+ sqft- 3 bed/ 3 full bath with Central A/C featuring a fab kitchen which is the heart of the home with Stainless Steel app's, GAS STOVE, granite counters, a picture window (looking out on to the 25x12 deck) and an eat in kitchen area. This opens up on one side into an inviting formal living room with a wood burning FP & bay window (Newer windows thru

Bob Ley Coldwell Banker Realty - Brookline

116 Manor Ave, Wellesley, MA 02482
/35
$3,300,000 Sold Aug 08, 2025
- 4,897 Sq Ft
- $674/SF
- 4 Days On Market
- 6 Beds
- 5.5 Baths
- Built 1920
1 Fletcher Rd, Wellesley Hills, MA 02481

Quintessential Wellesley Colonial in the coveted Country Club neighborhood offers a harmonious blend of historic elegance and modern comfort. With all the charming details intact, this center entrance colonial has been expanded and updated. Elegant thru hall to Kitchen/family room with formal dining and living room in front. Bright sunlit eat-in kitchen flows into a spacious family room with

Christine Lawrence Rutledge Properties

1 Fletcher Rd, Wellesley Hills, MA 02481

/29
Est $3,159,624 Not Listed For Sale
- 6 Beds
- 5 Baths
- 3,940 Sq Ft
27 College Rd, Wellesley, MA 02482

27 College Rd, Wellesley, MA 02482

/32
$1,995,000 Open Sat 11AM - 12:30PM
- 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
/23
$8,500 per month plus fees
- 4 Beds
- 2.5 Baths
- 2,164 Sq Ft
- House for Rent
11 Nantucket Rd Unit 11, Wellesley Hills, MA 02481

Attractive 4 bedroom Colonial near Bates Elementary School. First floor family room off eat-in kitchen with granite countertops, formal dining room and living room with fireplace. Second floor has main bedroom with bath, 3 additional bedrooms plus hall bath, hardwood floors throughout 1st and 2nd floors. 4th bedroom connects to main bedroom perfect for nursery or office. Lower level work

Jane Collinson Advisors Living - Wellesley

11 Nantucket Rd Unit 11, Wellesley Hills, MA 02481
/3
$2,800,000 Sold Aug 08, 2025
- 5,310 Sq Ft
- $527/SF
- 98 Days On Market
- 5 Beds
- 5 Baths
- Built 1930
27 Boulevard Rd, Wellesley Hills, MA 02481

New Construction and ideally located, this one-of-a-kind modern farmhouse blends thoughtful design with everyday comfort. Just minutes from the Wellesley Farms commuter rail, the Riverside green line, Route 95, and the Mass Pike, it offers both convenience and charm. Inside, three floors of well-planned living space flow effortlessly from one to the next. The sleek, open-concept kitchen features

Diane Marcoux Coldwell Banker Realty - Wellesley

27 Boulevard Rd, Wellesley Hills, MA 02481

/40
Est $1,999,642 Not Listed For Sale
- 5 Beds
- 3.5 Baths
- 3,398 Sq Ft
31 College Rd, Wellesley, MA 02482

31 College Rd, Wellesley, MA 02482

/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
/28
$30,000 per month plus fees
- 6 Beds
- 6.5 Baths
- 8,000 Sq Ft
- House for Rent
18 Sprague Rd, Wellesley Hills, MA 02481

A rare blend of timeless elegance and modern luxury in prime Wellesley Hills. This sun-drenched estate on 1⁄2 acre offers soaring ceilings, a stunning open floor plan, and high-end finishes throughout. The gourmet kitchen, luxurious owner’s suite with private roof deck, and versatile lower level with gym and guest suite create the perfect balance of comfort and style. The beautifully landscaped

Catherine Bassick Douglas Elliman Real Estate - Park Plaza

18 Sprague Rd, Wellesley Hills, MA 02481
/18
$1,280,000 Sold Aug 07, 2025
- 1,650 Sq Ft
- $776/SF
- 9 Days On Market
- 3 Beds
- 2 Baths
- Built 1958
1 Bow St, Wellesley Hills, MA 02481

Sparkling 3-bedroom, 2-bath home freshly updated and thoughtfully designed, offers comfort, style, and modern conveniences. Sun filled living room w/gas fireplace. The open-concept kitchen/dining features Caesar stone quartz countertops, a farmhouse sink, stylish backsplash & stainless steel appliances. Easy, one-level living with all bedrooms and a bathroom on the main floor. There is a

Patricia Bradley Rutledge Properties

1 Bow St, Wellesley Hills, MA 02481

/17
Est $900,774 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,218 Sq Ft
1 Dale St, Wellesley, MA 02482

1 Dale St, Wellesley, MA 02482

/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
/20
$5,300 per month plus fees
- 3 Beds
- 2.5 Baths
- 1,850 Sq Ft
- House for Rent
35 Bay State Rd, Wellesley Hills, MA 02481

Wonderful renovated Colonial home in beautiful Wellesley Farms neighborhood. Gleaming hardwood floors and new replacement windows throughout. Renovated kitchen featuring quartz counter tops & stainless steel appliance with kitchen island. Dining room off kitchen with built in hutch, fireplaced living room, 1/2 bath on 1st floor, BONUS room - could be home office, playroom, etc. Sliders to

Cynthia Parrella Cynthia Parrella

35 Bay State Rd, Wellesley Hills, MA 02481
/35
$2,200,000 Sold Aug 07, 2025
- 3,200 Sq Ft
- $688/SF
- 1 Day On Market
- 4 Beds
- 2.5 Baths
- Built 1938
9 Lafayette Cir, Wellesley, MA 02482

OPEN HOUSE CANCELLED OFFER ACCEPTED Impeccable sun-filled Colonial on a quaint cul de sac steps away from the new Hardy Elementary School and convenient to town, train, and Morses Pond. Chef’s kitchen and family room are a 1st floor highlight, opening onto the private brick patio and fenced backyard with stone wall and mature landscaping. A fireplaced living room with built-ins, elegant

Elke Cardella Compass

9 Lafayette Cir, Wellesley, MA 02482

/30
Est $1,511,169 Not Listed For Sale
- 3 Beds
- 1.5 Baths
- 1,562 Sq Ft
36 Bay View Rd, Wellesley, MA 02482

36 Bay View Rd, Wellesley, MA 02482

/15
$1,650,000
- Land
- 0.35 Acre
- $4,714,286 per Acre
39 College Rd, Wellesley, MA 02482

Build your dream waterfront home in Wellesley's coveted Hunnewell neighborhood. Building plans by renowned AD Design 100 architect, Michael Kim is designed for a sophisticated 4/5 bedroom home. Set on a cul-de-sac, this rare property offers stunning views of Morses Pond,100 acres of natural beauty with a swimming beach. Enjoy a private boat launch and easy access to Lake Waban walking trails.

Mizner+ Montero Gibson Sotheby's International Realty

39 College Rd, Wellesley, MA 02482
/9
$3,400 per month plus fees
- 2 Beds
- 1 Bath
- 1,100 Sq Ft
- House for Rent
16 Stonecleve Rd Unit 16, Wellesley, MA 02482

All new windows with updated kitchen and bathroom. Perfect two bedroom rental for anyone looking for kayaking, canoeing & swimming just steps from the back door on Morses Pond and the Crosstown trail to the public beach. Separate entrance for an office or workout room. Washer and dryer included. Walk out basement for easy storage of yard and outdoor toys. Very close to schools and Rt 9.

Mark Messina Domus Ave Realty

16 Stonecleve Rd Unit 16, Wellesley, MA 02482
/26
$2,380,000 Sold Aug 05, 2025
- 4,133 Sq Ft
- $576/SF
- 16 Days On Market
- 4 Beds
- 3 Baths
- Built 1966
73 Greylock Rd, Wellesley Hills, MA 02481

A New Price for a Rare Opportunity in Peirce Estates. This stately oversized Cape offers 4 beds with first floor primary suite and 3 full baths. Generous room sizes with gorgeous windows throughout the first floor. Pristine hardwoods in most rooms and lovely screened porch leading to a peaceful back yard. A treasure !

Mary Beth Grimm Coldwell Banker Realty - Wellesley

73 Greylock Rd, Wellesley Hills, MA 02481

/38
Est $3,365,552 Not Listed For Sale
- 5 Beds
- 6 Baths
- 4,857 Sq Ft
68 Parker Rd, Wellesley, MA 02482

68 Parker Rd, Wellesley, MA 02482

/42
$4,295,000 Open Sun 12PM - 1:30PM
- 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
/17
$1,950 per month plus fees
- 1 Bed
- 1 Bath
- 509 Sq Ft
- Apartment for Rent
410 Washington St Unit 2, Wellesley Hills, MA 02481

Great 1 bedroom apartment available on the second floor of a 4 unit building. Large and sunny eat-in kitchen, carpeted bedroom, living room with hardwood floors and bathroom with tub. Good closet space throughout, 1 car off-street parking included and coin-op laundry in the basement. All utilities included! -Heat, Hot Water and Electricity- Tenant pays for their Internet/Cable choice. Easy access

Colby Auger - Auger Realty Services Keller Williams Boston MetroWest

410 Washington St Unit 2, Wellesley Hills, MA 02481
/25
$1,560,000 Sold Aug 04, 2025
- 2,054 Sq Ft
- $759/SF
- 16 Days On Market
- 4 Beds
- 2.5 Baths
- Built 1920
145 Grove St, Wellesley, MA 02482

Welcome to this unique and inviting 4-bedroom, 2.5-bath Colonial nestled in the heart of Wellesley’s coveted Dana Hall neighborhood. Brimming with character and period details, this property offers high ceilings, sun-filled spaces and timeless charm. The home flows seamlessly with a gracious foyer, fireplaced living room and family room just off the eat-in-kitchen. Amazing yard with entertaining

Betsy Kessler Rutledge Properties

145 Grove St, Wellesley, MA 02482

/42
Est $2,508,608 Not Listed For Sale
- 4 Beds
- 4.5 Baths
- 4,400 Sq Ft
19 Bryn Mawr Rd, Wellesley, MA 02482

19 Bryn Mawr Rd, Wellesley, MA 02482

/4
$6,250,000
- Land
- 2.06 Acres
- $3,033,981 per Acre
87 Hundreds Rd, Wellesley, MA 02481

2+ACRE LOT in the heart of exclusive Wellesley Farms! Bring your dreams and ideas and get started on designing and building your custom home at one of the finest addresses in Wellesley. Plenty of room for anything you can dream up. Provided here as inspiration is a custom 10,000 TLAG home designed by renowned architecture firm Catalano Associates. Let our team help you get started or bring your

Betsy Kessler Rutledge Properties

87 Hundreds Rd, Wellesley, MA 02481
/32
$4,950 per month plus fees
- 4 Beds
- 1.5 Baths
- 2,000 Sq Ft
- Apartment for Rent
12 Leighton Rd Unit 1, Wellesley, MA 02482

Gorgeous unit in one of Wellesley's most elegant homes! Breathtaking 1910 stucco two unit Colonial in one of the most desirable Dana Hall neighborhoods. With it's lovely curb appeal this gem is brimming with history, grace and character beckoning memories of earlier days in Wellesley. Lovely, well maintained home with good sized rooms and endless charm. Front and back porches, fire placed living

Dan Groob Prime Property Group

12 Leighton Rd Unit 1, Wellesley, MA 02482
/41
$5,600,000 Sold Aug 04, 2025
- 7,391 Sq Ft
- $758/SF
- 38 Days On Market
- 6 Beds
- 7 Baths
- Built 2000
1 Old Farm Rd, Wellesley Hills, MA 02481

Experience unparalleled luxury in this stunning, custom built estate, gracefully sited on over an acre of park-like grounds in the coveted enclave of Wellesley Farms. Designed with timeless elegance and masterful craftsmanship, this 6 bedroom, 4 bath residence features soaring ceilings, a luminous open floor plan, and exquisite architectural detail throughout. A grand foyer introduces formal

Debi Benoit William Raveis R.E. & Home Services

1 Old Farm Rd, Wellesley Hills, MA 02481

/35
Est $1,810,659 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 3,056 Sq Ft
38 Garrison Rd, Wellesley, MA 02482

38 Garrison Rd, Wellesley, MA 02482

/25
$3,475,000
- 3 Beds
- 2.5 Baths
- 2,310 Sq Ft
148 Weston Rd Unit 207, Wellesley, MA 02482

The Bristol sets a new standard for elite concierge condominium living, offering discerning residents a rare blend of sophistication, style, and ease located in the heart of Wellesley. These thoughtfully designed residences showcase a truly carefree lifestyle, combining modern design with the charm of Wellesley offering a sophisticated lifestyle just moments from the vibrant town center. Inside,

Debi Benoit William Raveis R.E. & Home Services

148 Weston Rd Unit 207, Wellesley, MA 02482
/14
$12,000 per month plus fees
- 5 Beds
- 3.5 Baths
- 4,086 Sq Ft
- House for Rent
62 Pond Rd, Wellesley, MA 02482

Come home to your own 3 acre private oasis overlooking Wellesley's iconic Lake Waban. This 1898 5 BR, 3.5BA offers the best of both worlds: grandeur & elegance yet updated for today's needs. The first floor offers soaring ceilings and fireplaces in almost every room. The renovated eat in kitchen has a double oven and all stainless steel appliances opening to the family room. The original butlers

Susan Gear Coldwell Banker Realty - Wellesley

62 Pond Rd, Wellesley, MA 02482
/42
$3,300,000 Sold Aug 01, 2025
- 4,200 Sq Ft
- $786/SF
- 3 Days On Market
- 4 Beds
- 4.5 Baths
- Built 2017
69 Forest St, Wellesley Hills, MA 02481

Welcome to this stunning Gambrel Colonial in the desirable Country Club neighborhood! This home features an expansive front porch that gets beautiful morning sun. Enter through a gracious double foyer, with a spacious living room/study and formal dining room flanking the sides. The recently upgraded eat-in kitchen boasts a large island, Viking appliances, and a wet bar, flowing into a cozy family

Bell Petrini Group Coldwell Banker Realty - Boston

69 Forest St, Wellesley Hills, MA 02481

/32
Est $1,979,582 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,790 Sq Ft
24 Garrison Rd, Wellesley, MA 02482

24 Garrison Rd, Wellesley, MA 02482

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