Wellesley, MA Homes

/42
$6,150,000
- 6 Beds
- 9 Baths
- 9,036 Sq Ft
12 Winding River Cir, Wellesley, MA 02482

Welcome to 12 Winding River Circle in Wellesley, a stunning private retreat 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
/42
$2,175,000 Sold Mar 24, 2025
- 5,267 Sq Ft
- $413/SF
- 17 Days On Market
- 5 Beds
- 5.5 Baths
- Built 1957
75 Maugus Ave, Wellesley Hills, MA 02481

This is a rare opportunity to purchase a 1950s California ranch in Wellesley Hills. It offers the most incredible sunsets every day—expansive One-floor living with large windows overlooking the unobstructed views of conservation land. You will find hardwood floors, beautifully scaled large rooms, five bedrooms, and four and a half baths. The floor plan was mindfully created with a large living

David Ferrini Coldwell Banker Realty - Sudbury

75 Maugus Ave, Wellesley Hills, MA 02481

/24
Est $1,534,648 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,249 Sq Ft
44 Chesterton Rd, Wellesley Hills, MA 02481

44 Chesterton Rd, Wellesley Hills, MA 02481

/42
$5,995,000
- 6 Beds
- 8 Baths
- 9,848 Sq Ft
182 Winding River Rd, Wellesley, MA 02482

Enjoy life on the Charles River! Rarely available home that offers full backyard privacy w/ Elm Bank across. Incredible views of the river plus a dock for kayaks, paddleboards & small electric boats! 2006 custom 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

Melissa Dailey Coldwell Banker Realty - Wellesley

182 Winding River Rd, Wellesley, MA 02482
/3
$3,750,000 Sold Mar 24, 2025
- Land
- 0.98 Acre
- $3,826,531 per Acre
- 131 Days On Market
52 Valley Rd, Wellesley Hills, MA 02481

FULL ACRE LOT in the heart of exclusive Wellesley Farms! Bring your dreams and ideas and get started on designing and building your custom home. Shovel Ready - no demo delay. Half acre zoning. Particularly pretty, the property boasts a gentle rise in front with terrific privacy and extra large yard at one of the finest addresses in Wellesley. Plenty of room for pool or sport court. Rare chance to

Christine Lawrence Rutledge Properties

52 Valley Rd, Wellesley Hills, MA 02481

/30
Est $1,512,746 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,001 Sq Ft
2 Woodfield Rd, Wellesley, MA 02482

2 Woodfield Rd, Wellesley, MA 02482

/32
$1,199,000
- 3 Beds
- 2.5 Baths
- 2,388 Sq Ft
3 Sunnyside Ave, Wellesley, MA 02482

****This is the absolute best deal in Wellesley**** Why buy old when you can buy almost new for LESS? Why buy on Rt 9 or next to RR tracks when you can buy this house on a cul-de-sac? House is priced 200-300K- below market/comparable sales. Newly updated and energy-efficient (HERS-rated) 8-year-old house on cul-de-sac in a tranquil area of Wellesley. Enjoy seasonal views of a small creek in the

Constantine Iliev Brilliant Solution, Inc.

3 Sunnyside Ave, Wellesley, MA 02482
/4
$856,000 Sold Mar 21, 2025
- 1,367 Sq Ft
- $626/SF
- 180 Days On Market
- 3 Beds
- 1 Bath
- Built 1930
22 Stonecleve Rd, Wellesley, MA 02482

Heart of Morses Pond, this fixer-upper has great potential, ideal for builders and developers. This 3-bedroom, 1 bathroom home built in 1930 sits on a generous corner lot. Water views from three sides. The property features a backyard, unique to this Morses Pond neighborhood. Conveniently located to the brand new Hardy Elementary School. Nature trails and pond access just outside your front door.

The Scott Group Advisors Living - Wellesley

22 Stonecleve Rd, Wellesley, MA 02482

/22
Est $2,368,355 Not Listed For Sale
- 5 Beds
- 3 Baths
- 2,938 Sq Ft
23 Northgate Rd, Wellesley Hills, MA 02481

23 Northgate Rd, Wellesley Hills, MA 02481

/30
$8,495,000
- 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
/32
$1,875,000 Sold Mar 19, 2025
- 4,257 Sq Ft
- $440/SF
- 44 Days On Market
- 4 Beds
- 3.5 Baths
- Built 2016
20 Westerly St Unit A, Wellesley, MA 02482

The search is over!!! Turn-key living in the heart of Wellesley Center. Just a stone's throw to Tatte, Starbucks, The Cottage, Roche Brothers, Captain Marden's & more.... plus the train! Three full floors of living in this 4 bedroom townhome boasts over 4000 sq ft of living space. Kitchen with center island opens to a family with fireplace and access to fenced-in backyard. Walk-in food pantry

Melissa Dailey Coldwell Banker Realty - Wellesley

20 Westerly St Unit A, Wellesley, MA 02482

/33
Est $2,858,156 Not Listed For Sale
- 5 Beds
- 4.5 Baths
- 4,700 Sq Ft
22 Northgate Rd, Wellesley Hills, MA 02481

22 Northgate Rd, Wellesley Hills, MA 02481

/25
$1,950,000
- 5 Beds
- 3.5 Baths
- 3,784 Sq Ft
7 Cliff Rd, Wellesley Hills, MA 02481

Sparkling home set back on one of Wellesley's much admired locations- Cliff Road. This property boasts beautiful renovations throughout including white oak floors and new systems. There is an impressive kitchen with the perfect layout for the "cook", a center island and a sunny dining area. The heartbeat of the house is the light and bright fireplaced family room framed by expansive windows.

Teri Adler MGS Group Real Estate LTD - Wellesley

7 Cliff Rd, Wellesley Hills, MA 02481
/25
$1,280,000 Sold Mar 18, 2025
- 1,648 Sq Ft
- $777/SF
- 3 Days On Market
- 3 Beds
- 1.5 Baths
- Built 1926
21 Intervale Rd, Wellesley Hills, MA 02481

This picture-perfect 1920's Colonial, nestled in one of Wellesley’s most beloved neighborhoods, blends historic charm with modern finishes. A welcoming front porch invites you in, where you’ll find hardwood floors, high ceilings & an abundance of natural light. The family room opens to the dining room with original cabinetry & custom built-ins- ideal for entertaining. The updated kitchen features

The Lara & Chelsea Collaborative Coldwell Banker Realty - Wellesley

21 Intervale Rd, Wellesley Hills, MA 02481

/40
Est $1,595,812 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,962 Sq Ft
16 Northgate Rd, Wellesley Hills, MA 02481

16 Northgate Rd, Wellesley Hills, MA 02481

/31
$5,895,000
- 6 Beds
- 7.5 Baths
- 9,494 Sq Ft
33 Royalston Rd, Wellesley, MA 02481

Setting the bar higher- this newly constructed home offers unparalleled luxury on four expansive levels with top quality finishes. The first floor invites relaxation and a backdrop for entertaining- a grand family room boasts a cathedral ceiling with wood trim, a wet bar, oversized windows and access to the covered patio. Equally impressive is the fireplaced family room. Crafted by the renowned

Teri Adler MGS Group Real Estate LTD - Wellesley

33 Royalston Rd, Wellesley, MA 02481
/23
$1,226,000 Sold Mar 17, 2025
- 1,522 Sq Ft
- $806/SF
- 9 Days On Market
- 2 Beds
- 2 Baths
- Built 1973
65 Grove St Unit 342, Wellesley, MA 02482

Discover comfortable, upscale living in this renovated 2-bedroom, 2-bathroom Wellesley Green condo with picturesque views. The white kitchen is open to the eating area making it sunny and bright. Lovely built in cabinets, shutters, and hardwood floors in large family room. Residents have the luxury of a private community pool. Plus, you'll have an elevator, underground garage space, and extra

Christine Lawrence Rutledge Properties

65 Grove St Unit 342, Wellesley, MA 02482

/41
Est $1,644,001 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,400 Sq Ft
12 Northgate Rd, Wellesley Hills, MA 02481

12 Northgate Rd, Wellesley Hills, MA 02481

/22
$1,350,000 Open Sun 11:30AM - 1PM
- 3 Beds
- 2.5 Baths
- 1,800 Sq Ft
58 Oak St, Wellesley, MA 02482

MAJOR PRICE REDUCTION~OPEN HOUSE SUNDAY 6/22 11:30 to 1:00~READY TO MOVE IN~JUST COMPLETED professionally interior paint, exterior porch deck(s) painted, interior hardwood floors just refinished today(6/18/25)~GREAT LOCATION minutes to Schools, Commuter Train to Boston, Shopping/Restaurants, Close drive time to City Of Boston~Builder's own custom stand alone condo~Two covered porches, 7 Rms/3

Bob Carey Carey Realty Group, Inc.

58 Oak St, Wellesley, MA 02482
/42
$1,428,000 Sold Mar 17, 2025
- 1,997 Sq Ft
- $715/SF
- 8 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1936
20 Sunset Rd, Wellesley, MA 02482

OFFER DEADLINE 1/14/2025 at 6 p.m. W elcome to this Charming home in the sought-after College Heights area of Wellesley. This center entry New England Colonial offers a rare opportunity to live in a Norman Rockwell-esque setting and is truly a fabulous opportunity with tremendous potential. You are welcomed into the center foyer that opens into a fireplaced living room with an attached sunroom

Karole O'Leary Lamacchia Realty, Inc.

20 Sunset Rd, Wellesley, MA 02482

/32
Est $1,936,670 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,868 Sq Ft
36 S River St, Wellesley, MA 02482

36 S River St, Wellesley, MA 02482

/20
$1,350,000 Open Sun 11:30AM - 1PM
- 3 Beds
- 2.5 Baths
- 1,800 Sq Ft
58 Oak St Unit 58, Wellesley, MA 02482

MAJOR PRICE REDUCTION~OPEN HOUSE SUNDAY 6/22–11:30 to 1:00~JUST COMPLETED professionally interior paint, exterior porch deck(s) painted, interior hardwood floors refinished today(6/18/25)~GREAT LOCATION minutes to Schools, Commuter Train to Boston, Shopping/Restaurants~Close drive time to the City Of Boston~Builder's own home/stand alone condo-Two covered porches, 7 Rms/3 Bedrooms/2.5 Baths, 1

Bob Carey Carey Realty Group, Inc.

58 Oak St Unit 58, Wellesley, MA 02482
/19
$675,000 Sold Mar 10, 2025
- 840 Sq Ft
- $804/SF
- 80 Days On Market
- 2 Beds
- 1 Bath
- Built 1870
40 Cedar St, Wellesley Hills, MA 02481

Attention contractors, renovators, and end-users: unlock the potential of this fixer-upper nestled in the heart of Wellesley. This property is now ready for a visionary owner to breathe new life into its classic appeal. This four-room farmhouse presents an exceptional opportunity for those eager to create their dream residence. The spacious backyard further elevates the overall appeal.

Krongel & Paul Hammond Residential Real Estate

40 Cedar St, Wellesley Hills, MA 02481

/40
Est $1,542,319 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 3,012 Sq Ft
30 S River St, Wellesley, MA 02482

30 S River St, Wellesley, MA 02482

/6
$7,995,000 New Construction
- 6 Beds
- 7 Baths
- 8,093 Sq Ft
222 Grove St, Wellesley, MA 02482

Discover unrivaled elegance and privacy in Wellesley’s coveted Dana Hall Neighborhood. Set on over an acre in one of Wellesley’s most sought-after neighborhoods, 222 Grove Street offers the perfect balance of privacy, and convenience. Designed by a renowned local architect, this stunning new home combines sophisticated design with modern comfort, creating a serene retreat just moments from town.

Steve & Nicole Connolly Group Coldwell Banker Realty - Wellesley

222 Grove St, Wellesley, MA 02482
/10
$800,000 Sold Mar 07, 2025
- Land
- 0.33 Acre
- $2,424,242 per Acre
- 1 Day On Market
22-24 Edgemoor Ave, Wellesley, MA 02482

Offer accepted! A rare opportunity for new construction in Wellesley in popular Edgemoor/Overbrook neighborhood. Level lot with 120 feet of frontage on Wellesley side. Buyer to do their own due diligence.

Jane Neilson Douglas Elliman Real Estate - Wellesley

22-24 Edgemoor Ave, Wellesley, MA 02482

/42
Est $3,290,442 Not Listed For Sale
- 6 Beds
- 4.5 Baths
- 5,320 Sq Ft
64 Halsey Ave, Wellesley, MA 02482

64 Halsey Ave, Wellesley, MA 02482

/40
$4,695,000 New Construction
- 7 Beds
- 8 Baths
- 6,800 Sq Ft
30 Hobart Rd, Wellesley, MA 02482

NEW CONSTRUCTION,walk-to-town location,this stunning home boasts 7 spacious bedrooms, 6 full baths, and 2 half baths. Step into elegance with high-end finishes and modern amenities throughout. This sun-splashed floor plan flows seamlessly from the gourmet kitchen with 72' fridge freezer tower, 60 inch Gas Range with dual oven, 2 dishwashers, 2 sinks and a stunning oversized island that is the

Joseph Fleming JT Fleming & Company

30 Hobart Rd, Wellesley, MA 02482
/26
$3,150,000 Sold Mar 07, 2025
- 6,000 Sq Ft
- $525/SF
- 42 Days On Market
- 6 Beds
- 6.5 Baths
- Built 1929
21 Colburn Rd, Wellesley Hills, MA 02481

Meticulous renovation & expansion of a 1920's white-washed brick & clapboard colonial. A highly-regarded local builder has created a luxurious oasis in a coveted Wellesley neighborhood. With natural light throughout, the property boasts perfect entertaining spaces. The living + dining rooms are anchored by a gorgeous double-sided fireplace, and the custom kitchen w/a walk-in pantry + oversized

Beyond Boston Properties Group Compass

21 Colburn Rd, Wellesley Hills, MA 02481

/40
Est $2,566,334 Not Listed For Sale
- 4 Beds
- 4.5 Baths
- 5,025 Sq Ft
18 Halsey Ave, Wellesley, MA 02482

18 Halsey Ave, Wellesley, MA 02482

/37
$1,699,000 Pending
- 5 Beds
- 4 Baths
- 3,272 Sq Ft
6 Willow Park, Wellesley Hills, MA 02481

Priced to sell! Best value in Wellesley. This expansive 5 beds 4 baths Colonial offers the perfect blend of space, style, & location-just a short walk to Fiske Elementary with easy access to highways, town center, and parks.The main level features a front-to-back layout with a formal dining room and fireplace, updated kitchen with stainless steel appliances, sunny sunroom, & large deck, ideal for

Bonnie Lai RE/MAX Real Estate Center

6 Willow Park, Wellesley Hills, MA 02481
/26
$2,895,000 Sold Mar 06, 2025
- 4,436 Sq Ft
- $653/SF
- 6 Days On Market
- 5 Beds
- 5 Baths
- Built 2014
88 Hopkinson St, Wellesley Hills, MA 02481

Welcome to this stunning, young colonial set within the sought-after Hunnewell School District. With its thoughtfully designed floor plan, this home is perfect for modern living, offering both space and style. As you step inside, you'll immediately appreciate the tall ceilings and gleaming hardwood floors. A spacious family room boasts a cozy fireplace and large windows that allow natural light

Teri Adler MGS Group Real Estate LTD - Wellesley

88 Hopkinson St, Wellesley Hills, MA 02481

/25
Est $2,993,857 Not Listed For Sale
- 4 Beds
- 4.5 Baths
- 4,400 Sq Ft
6 Halsey Ave, Wellesley, MA 02482

6 Halsey Ave, Wellesley, MA 02482

/42
$1,835,000 Pending
- 4 Beds
- 2.5 Baths
- 2,856 Sq Ft
112 Woodside Ave, Wellesley, MA 02482

Pristine and secluded! This timeless young Colonial home, offers well-proportioned rooms, modern amenities, is nestled on a picturesque, beautifully landscaped lot. The highlights feature a welcoming portico/foyer, easy flow living and formal dining, a fireplaced family room with vaulted ceiling & skylights. A stately gourmet chef’s kitchen is delightfully laid out w/ample cabinets, granite

Anita Lin Coldwell Banker Realty - Lexington

112 Woodside Ave, Wellesley, MA 02482
/14
$2,400,000 Sold Mar 03, 2025
- 2,323 Sq Ft
- $1033/SF
- 5 Days On Market
- 4 Beds
- 2.5 Baths
- Built 1950
15 Allen Rd, Wellesley Hills, MA 02481

Wellesley's desirable Country Club neighborhood. This Colonial home offers 4 bedrooms and 2.5 baths on a level 20,381 sq ft lot!. Step inside to a spacious foyer that leads to a lovely, fire-placed living room to the left & spacious dining room to the right, perfect for relaxing or entertaining guests. The side entry door leads you to an eat-in kitchen. Upstairs, you'll find the primary suite

Jodie Zinna Coldwell Banker Realty - Wellesley

15 Allen Rd, Wellesley Hills, MA 02481

/35
Est $2,782,561 Not Listed For Sale
- 4 Beds
- 4.5 Baths
- 4,500 Sq Ft
45 Marshall Rd, Wellesley, MA 02482

45 Marshall Rd, Wellesley, MA 02482

/28
$1,225,000 Pending
- 3 Beds
- 2 Baths
- 2,896 Sq Ft
23 Wareland Rd, Wellesley Hills, MA 02481

Nestled on nearly half an acre, this charming Cape offers the perfect blend of comfort and convenience. With eight rooms, including three spacious bedrooms and two full baths, this home is thoughtfully designed for modern living. The updated kitchen, complete with a cozy dining area, seamlessly flows into a sun-drenched three-season porch, ideal for relaxing or entertaining. A fireplaced living

Jennifer Madden Coldwell Banker Realty - Wellesley

23 Wareland Rd, Wellesley Hills, MA 02481
/2
$1,115,000 Sold Feb 27, 2025
- 1,512 Sq Ft
- $737/SF
- 3 Days On Market
- 3 Beds
- 1.5 Baths
- Built 1928
32 Cavanaugh Rd, Wellesley Hills, MA 02481

One of Wellesley's most adored streets, close to the Bates school and the Boulder Brook Reservation. Charming 1920's home with high ceilings and set on a level lot is awaiting a contractor/builder/end-user to restore and renovate this wonderful opportunity in a beloved neighborhood. The property is being sold "as is". The buyer is responsible for removing all contents of the home/property. Offers

The Lara & Chelsea Collaborative Coldwell Banker Realty - Wellesley

32 Cavanaugh Rd, Wellesley Hills, MA 02481

/35
Est $3,143,899 Not Listed For Sale
- 5 Beds
- 4.5 Baths
- 4,600 Sq Ft
36 Patton Rd, Wellesley, MA 02482

36 Patton Rd, Wellesley, MA 02482

/41
$6,250,000 Pending
- 6 Beds
- 7 Baths
- 7,391 Sq Ft
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

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