Refine Search
Map
Sort by
12 Winding River Cir, Wellesley
$4,999,000
6 Beds ⋅ 9 Baths ⋅ 73555707 MLS
Nature Lovers Paradise on the Charles River! Stunning in every season, each element of this spectacular property is crafted to maximize your enjoyment and access to the great outdoors. Reimagined by renowned architect Patrick Ahern, the exterior boasts a flat grassy backyard and stone patios with unobstructed views. Inside, a gracious and flexible floor plan is filled with light and views from myriad windows, French doors, and private balconies. First floor living with exquisite primary bedroom suite, a great room, expansive living room, dining and updated kitchen w/ light-filled breakfast room, an add’l bedroom suite and choice of offices complete the main floor. Upstairs, 4 more ensuite bedrooms, including a 2nd primary suite option. Large walk-out finished LL w/ bar, gym & media room. 3 car garage and flat courtyard driveway off protected cul de sac within minutes of extensive Wellesley Trails and Town Center. A notch above the rest. Bring your hiking shoes, kayaks, lounge chairs and lawn games!

12 Winding River Cir, Wellesley

Listing courtesy of Listing Agent: Christine Lawrence from Listing Office: Rutledge Properties.
23 Bellevue, Wellesley
$3,600,000
5 Beds ⋅ 6 Baths ⋅ 73555589 MLS
Recently renovated expansive Cape with over 6200 sq ft of living space on three floors. Beautifully landscaped ½ acre lot in the very desirable and prestigious Peirce Estates. Generously proportioned living, dining, and family rooms, first floor Library/Office, updated eat in kitchen, renovated marble baths and optional first floor main suite. Total 5 Bedrooms, 3 full and 3 half baths. Crystal chandeliers throughout the house. Fully finished basement with checkered Italian marble floors in the front room. Fenced back yard with a deck and a stone fire pit. Attached two car garage. Bates elementary school. Meticulously maintained this home is perfect for peaceful living or entertaining friends.

23 Bellevue, Wellesley

Listing courtesy of Listing Agent: Ritu Chawla from Listing Office: Coldwell Banker Realty - Wellesley.
265 Weston Rd, Wellesley
$2,750,000
5 Beds ⋅ 6 Baths ⋅ 73552915 MLS
PRICE ADJUSTMENT! Exceptional opportunity to own 5,100+ sq. ft. of luxury 2024 construction offering outstanding value in one of Wellesley's most convenient in-town locations. Just steps to Hardy Elementary, Morse's Pond, Fells Library, Wellesley Center & commuter rail. Thoughtfully designed for modern living, this sun-filled home features soaring ceilings, exceptional craftsmanship & four finished levels. Stunning chef's kitchen w/ oversized island & premium appliances flows seamlessly into dramatic family room—ideal for everyday living & entertaining. Elegant dining room, thoughtfully designed mudroom & private bedroom suites on the 2nd, 3rd & lower levels provide exceptional flexibility for guests, au pair, home office or multigenerational living. Gorgeous primary bedroom suite w/ lavish bath. Expansive lower level offers endless possibilities for recreation, fitness or media. A rare opportunity to enjoy the quality, space & convenience of nearly new construction.

265 Weston Rd, Wellesley

Listing courtesy of Listing Agent: Petrone-Hunter Realty Group from Listing Office: Coldwell Banker Realty - Wellesley.
26 Pleasant St Unit B, Wellesley
$1,019,999
2 Beds ⋅ 2 Baths ⋅ 73551418 MLS
This Brighton 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, two bedrooms, two bathrooms and a versatile room on the third floor. The modern granite kitchen flows into a dining area that opens to a private patio, while the inviting family room with a fireplace creates the perfect space to relax. The finished lower level adds a recreation room and laundry, and two assigned outdoor parking spaces complete this exceptional offering. 2025 roof and skylight windows.

26 Pleasant St Unit B, Wellesley

Listing courtesy of Listing Agent: Zhen Guo from Listing Office: Coldwell Banker Realty - Brookline.
28 Longfellow, Wellesley
$34,000
6 Beds ⋅ 5 Baths ⋅ 73550778 MLS
Welcome to this exquisitely restored Victorian, where historic charm and contemporary sophistication come together in one of Wellesley's most desirable neighborhoods. Thoughtfully renovated, this exceptional residence offers luxurious living with designer finishes, custom craftsmanship, and an inviting floor plan designed for today's lifestyle. Designed with comfort and flexibility in mind, the home offers spacious bedrooms, multiple living and gathering areas, dedicated workspaces, and modern conveniences including high-speed internet, zoned heating and cooling, heated floors, and Smart TVs, The beautifully landscaped grounds feature a welcoming farmer's porch, expansive outdoor living and dining spaces, and a cozy fire pit—ideal for relaxing evenings, outdoor living, or enjoying New England's changing seasons. Rented furnished only!

28 Longfellow, Wellesley

Listing courtesy of Listing Agent: Kristen DiBella from Listing Office: Boom Realty.
5 Westerly Street, Wellesley
$3,900
2 Beds ⋅ 2 Baths ⋅ 73546505 MLS
All renovated this 2 bedroom, 1.5 bathroom town house is conveniently located near Linden Square, Wellesley Center and commuter rail. High ceilings and great sunlight! The eat-in kitchen, living room, dining room and mudroom along with half bath are on the first floor. Bedrooms and laundry are on the second floor. Central AC and garage parking. The home features a lovely yard and extra storage space on the third floor and lower level.

5 Westerly Street, Wellesley

Listing courtesy of Listing Agent: Melissa Dailey from Listing Office: Coldwell Banker Realty - Wellesley.
22 Cedar St, Wellesley
$1,195,000
3 Beds ⋅ 3 Baths ⋅ 73545904 MLS
Classic charm meets modern luxury in this beautifully updated 3-bedroom, 3-bathroom 1920's Colonial. The main level welcomes you with high ceilings, an open concept layout and an abundance of natural light throughout. Flexible space for living and dining as well as generous family room. Gorgeous modern eat in kitchen with stainless steel appliances and gas cooking. Step outside to your private oasis featuring a gorgeous back deck and a meticulously landscaped terraced yard, perfect for outdoor entertaining and sunset views. Situated in a prime, highly sought-after Wellesley neighborhood, this home offers an unbeatable commuting location with easy access to all major routes and is just moments away from Schofield Elementary School.

22 Cedar St, Wellesley

Listing courtesy of Listing Agent: The Shulkin Wilk Group from Listing Office: Compass.
43 Monadnock Road, Wellesley
$4,995,000
6 Beds ⋅ 6 Baths ⋅ 73545332 MLS
One of Wellelsey's signature properties! Rarely available 18 room estate w/ 4 floors of living situated in the heart of Peirce Estates. Stunning foyer w/ curved staircase. Sunken living room w/ coffered ceilings & stone fireplace. Oversized dining room w/ bay window plus large butler's pantry. Kitchen w/ stainless appliances, center island & breakfast nook. One of a kind family room filled w/ built-in bookcases, coffered ceiling, fireplace & wet bar perfect for entertaining & everyday living. Wood panel den/office. Main bedroom w/ 2 walk-in closets & fireplace. 3 additional beds & 2 baths. Large sitting room/bonus room w/ fireplace completes 2nd floor. Third floor w/ 2 more beds & bath plus another large bonus room with built-in bunk beds. Lower level w/ playroom, game room & bar room. Over 7700 sq ft with almost one acre of privacy abutting the reservoir. Fieldstone patio. 400 amp service. 3 car garage & steel beam construction. Your chance to own one of Wellesley's most iconic homes!

43 Monadnock Road, Wellesley

Listing courtesy of Listing Agent: Melissa Dailey from Listing Office: Coldwell Banker Realty - Wellesley.
209 Bristol Rd, Wellesley
$3,095,000
6 Beds ⋅ 5 Baths ⋅ 73542007 MLS
Set on a tree-lined block in the coveted Cliff Estates enclave, this to-the-studs 2025-26 renovation + expansion of a classic NE 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. Anchored by a breathtaking central island and 42” Wolf range, the kitchen opens to a spacious family room, dining, and separate great room which all embrace views of the lushly landscaped nearly ½-acre lot. Versatile 1st fl ensuite guest room / office. Four gracious 2nd fl inc. four gracious bedrooms and three elegant new baths inc. a luxe primary suite + laundry. Amazing skylit 3rd fl with new 2026 dormer inc. a 6th bedroom or office + auxiliary living area. Walkout lower level w direct-entry garage, mudroom, ½ bath, open-plan LR or gym + sliders to covered patio and grassy yard. Premier location.

209 Bristol Rd, Wellesley

Listing courtesy of Listing Agent: Elisabeth Preis from Listing Office: Compass.
45 White Oak Rd, Wellesley
$8,995,000
5 Beds ⋅ 6 Baths ⋅ 73540092 MLS
Not all new construction is created equal. The result of a visionary collaboration between acclaimed architecture firm Of Possible and renowned custom builder NS Builders, 45 White Oak Rd represents a rare opportunity to own a residence where design, craftsmanship, and performance were never compromised. Conceived as a showcase of what is possible when architecture and construction are executed at the highest level, this 7,200+ sq. ft. home balances architectural significance with the warmth and functionality required for everyday living. Expansive walls of glass create a seamless connection to the beautifully landscaped grounds, while custom German white oak millwork, curated natural stone finishes, and exceptional detailing reflect an uncompromising commitment to quality throughout. Designed for both grand entertaining and comfortable daily living, the home offers a level of craftsmanship, sophistication, and performance rarely found in today's market.

45 White Oak Rd, Wellesley

Listing courtesy of Listing Agent: The Sarkis Team from Listing Office: Douglas Elliman Real Estate - The Sarkis Team.
23 Bellevue, Wellesley
$15,000
5 Beds ⋅ 6 Baths ⋅ 73538689 MLS
Beautifully maintained and recently renovated single family home for rent in one of the prestigious neighborhoods in Wellesley. Main level bedroom suite, plus additional main suite on first floor and three other bedrooms on the second floor. Total 5 bedrooms. Three full and three half baths. Fully finished basement. Open floor plan and lots of natural light and professionally landscaped grounds that include a deck and a fire pit. Crystal chandeliers and high end light fixtures throughout the house. Great for everyday living and entertaining.

23 Bellevue, Wellesley

Listing courtesy of Listing Agent: Ritu Chawla from Listing Office: Coldwell Banker Realty - Wellesley.
30R Morses Pond Road, Wellesley
$1,300,000
3 Beds ⋅ 2 Baths ⋅ 73537936 MLS
Lovely Cottage on Morses Pond with stunning waterfront views, it's as if you are on a vacation everyday. Extensively renovated & thoughtfully reimagined to showcase the natural beauty of its surroundings with an easy open concept design. The 1st floor's spacious living room has a fireplace & built-ins that flow seamlessly to a timeless white shaker cabinetry kitchen w/SS appliances, marble & center island w/ seating. The adjacent dining room with a large bay window & window seat, is a wonderful spot for your morning coffee or sunset dinners. The 2nd floor has 3 well proportioned bedrooms all with terrific closet space, a full bath & laundry. Bonus rooms in the walk out lower level, offer flexibility for a home office, playroom or workroom. Outdoor fun all year round in a vibrant neighborhood, enjoy kayaking, canoeing to ice skating from your backyard. Relax at the end of the day on the wrap around deck watching the swans drift by on the pond. Surround yourself with nature and take in the tranquility of this special home.

30R Morses Pond Road, Wellesley

Listing courtesy of Listing Agent: Patricia Bradley from Listing Office: Rutledge Properties.
45 Longmeadow Rd, Wellesley
$5,500,000
7 Beds ⋅ 9 Baths ⋅ 73536264 MLS
Set on a beautifully flat lot in one of Wellesley’s most desirable neighborhoods, this exceptional Colonial offers a rare combination of luxury, space, and timeless design. Located in a special community with a picturesque meadow at its center, providing a peaceful setting. Featuring 7 bedrooms, 7 full and 2 half bathrooms, this thoughtfully designed home offers flexibility for today’s lifestyle. The stunning chef’s kitchen features a center island, top-of-the-line appliances, custom cabinetry, and separate walk-in pantry. Spacious living areas, elegant formal rooms, high ceilings, natural light, and beautiful finishes create an inviting atmosphere. The luxurious primary suite offers a private retreat, while the generous secondary bedrooms provide comfort for family and guests. Multiple spaces allow for work, recreation, and entertaining. The expansive backyard is ideal for outdoor enjoyment, conveniently located near Wellesley’s top-rated schools, town center, train, and major routes.

45 Longmeadow Rd, Wellesley

Listing courtesy of Listing Agent: Lisa Sewall from Listing Office: Coldwell Banker Realty - Wellesley.
5 Seaward Road Unit 3, Wellesley
$2,750
1 Beds ⋅ 1 Baths ⋅ 73531178 MLS
On-site Parking space available 24 hours per day - central air and in-unit laundry are included! 3rd floor, penthouse apartment has a unique floor plan! Living room, bedroom, reading loft, newer kitchen with separate dining area and newer tiled bathroom offer sun filled space throughout. Kitchen is fully applianced including a dishwasher. Other features include replacement windows and plenty of closets! Landlord pays for heat and hot water, snow removal and rubbish removal. Tenant pays for electricity. Minutes to Brook Path, Wellesley Hills train and Wellesley Hills shops and restaurants. Plentiful parking evenings, nights and weekends/holidays. “We do not discriminate on the basis of age, race, color, sex, national origin, religion, disability, familial status (having children under the age of 18), military status, gender identity, sexual orientation, marital status, or receipt of public assistance including housing vouchers.”

5 Seaward Road Unit 3, Wellesley

Listing courtesy of Listing Agent: Mary Ann Figoni from Listing Office: Centre Realty Group.
16 Stearns Rd. Unit 203, Wellesley
$1,498,000
2 Beds ⋅ 3 Baths ⋅ 73512685 MLS ⋅ ['The Albion'] BLDG.
Welcome to the ALBION! 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. This unit includes two 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 spacious living room offers a cozy fireplace and flows seamlessly into a separate dining area.The primary suite includes a walk-in closet and a luxurious primary bath. The second bedroom opens to a private deck. There is in-unit laundry. Conveniently located close to shopping, restaurants, and major highway access.

16 Stearns Rd. Unit 203, Wellesley

Listing courtesy of Listing Agent: Bartlett Albion Group from Listing Office: Hammond Residential Real Estate.
2 Marigold Ave, Wellesley
$1,149,000
4 Beds ⋅ 2 Baths ⋅ 73511385 MLS
Top condition 4 bed room, single family, 1.5 bath on the corner of a cul-de- sac. Great location with easy access to Routes 9, 16 & 30. Updated kitchen and baths. Insulated windows Finished basement with large laundry/storage room.

2 Marigold Ave, Wellesley

Listing courtesy of Listing Agent: William Gath from Listing Office: Realty Executives Boston West.
100 Albion Rd, Wellesley
$2,650,000
5 Beds ⋅ 4 Baths ⋅ 73507050 MLS
Located on one of Wellesley’s most coveted roads in Cliff Estates, 100 Albion is a beautifully appointed pillared white Colonial set on .77 acres of professionally landscaped grounds. Blending timeless architecture with modern living, the main level offers a gracious fireplaced living room with a large picture window, an elegant dining room, a private office, and an expansive kitchen centered around a large island. These spaces flow seamlessly into a spacious fireplaced family room with custom cabinetry and out to a brand-new deck ideal for indoor/outdoor entertaining. The first floor also includes a well-placed laundry room with a full bath. Upstairs are five bedrooms, including a serene primary suite with a walk-in closet, along with four additional bedrooms and two full baths. The finished walk-out lower level features a full bath and bar, providing versatile living space. Exceptional curb appeal, a circular driveway, and beautifully landscaped grounds complete this impressive home.

100 Albion Rd, Wellesley

Listing courtesy of Listing Agent: Debi Benoit from Listing Office: William Raveis R.E. & Home Services.
144 Washington Street, Wellesley
$3,450,000
5 Beds ⋅ 6 Baths ⋅ 73499362 MLS
Beautiful New Construction in desirable Wellesley Hills near Warren Park. The inviting front porch sets the tone of the home's warmth & craftsmanship. It's 5,800 sq.ft. of living over 4 levels. No detail has been overlooked, from the layout, custom built-ins, coffered ceiling & shiplap accents. The Chef's kitchen has Thermador appliances, large center island and sunny eat-in area that abuts a spacious family room. Flexible first floor w/office or living room & a formal dining room. 5 bedrooms, including a Primary Suite w/walk-in closet & spa-like bath. The expansive lower level has a full bath offering plenty of space for a playroom & gym. The oversized mudroom w/custom built-ins, easy access to the stone patio will not disappoint. A 2 car garage w/overflow parking space, making coming & going a breeze. It's an ideal commuter location near the Hills Train and short distance to shops, restaurants, & Hills Library...ready and waiting for you!

144 Washington Street, Wellesley

Listing courtesy of Listing Agent: Patricia Bradley from Listing Office: Rutledge Properties.
196 Pond Road, Wellesley
$5,695,000
5 Beds ⋅ 7 Baths ⋅ 73499334 MLS
Once in a lifetime opportunity to own in Wellesley's most coveted premier historic location, Pond Road. Featuring the finest custom craftsmanship throughout, professionally engineered mechanical systems, smart house and professionally designed ultra high end finishes. Over 9400 sq ft of living space on 3 floors. The floor plan everybody wants with a 1200 sq ft great room and over 10 foot ceilings. Oversized mudroom and pantry. First floor includes white oak herring bone hardwoods. 2nd floor ceilings 14-20 feet! An incredible main suite. All bedrooms en-suite with walk-in closets. Plus a 2nd floor lounge room or incredible guest suite. Lower level is unprecedented with 17 ft ceiling in 1/2 court basketball/ rec room (size of space also work for squash) with viewing room including wet bar. Theatre/media room with additional wet bar plus a gym with full bath including steam shower. Large flat yard. Close to Wellesley trails and town center.

196 Pond Road, Wellesley

Listing courtesy of Listing Agent: Melissa Dailey from Listing Office: Coldwell Banker Realty - Wellesley.
6 Willow Street, Wellesley
$999,900
3 Beds ⋅ 3 Baths ⋅ 73497359 MLS
A great opportunity for a buyer who understands the value of sweat equity and is willing to make some improvements! This delightfully charming Cape style home offers a versatile open concept floor plan.  The first floor flows seamlessly to two separate fireplace living areas as well as a dining room with hardwood flooring throughout. The updated kitchen boasts granite countertops, stainless appliances, ample storage and breakfast bar and opens to a large rear deck, perfect for entertaining.  Upstairs boasts  a large en-suite Primary bedroom, two additional bedrooms, another full bath along with an office/den bonus  space. There are plenty of custom built-ins, cabinets and quaint nooks that make this an adorable gem of a home.  The acreage is combined lots 6 & 6R and offers a half acre of privacy or possible room to grow. The home needs some exterior and basement improvements to reimagine it to your dream!  Terrific location, moments to Fiske elementary school & easy access to Rt.9,128.

6 Willow Street, Wellesley

Listing courtesy of Listing Agent: Frank Celeste from Listing Office: Gibson Sotheby's International Realty.
680 Worcester Street Unit 205, Wellesley
$4,100
2 Beds ⋅ 2 Baths ⋅ 73494081 MLS
Beautifully designed 2-bedroom apartment in newly built building featuring an open-concept kitchen and family room. This light-filled space offers two bedroom, two full bathrooms with in unit laundry, modern finishes and effortless living in prime location.

680 Worcester Street Unit 205, Wellesley

Listing courtesy of Listing Agent: Elizabeth Derenzo from Listing Office: J. Derenzo & Associates, LLC.
16 Stearns Rd Unit 208, Wellesley
$1,747,200
2 Beds ⋅ 3 Baths ⋅ 73488987 MLS ⋅ ['The Albion'] BLDG.
2 garage parking spots included if offers by 5/31!!! Welcome to the ALBION! New Construction Wellesley’s newest luxury condominium building. This stunning 2-bedroom, den/office and 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 spacious primary suite offers a walk-in closet and a spa-like bath designed for relaxation. The 2nd bedroom has outdoor access to a private balcony. In-unit laundry. Exercise & game rooms on 2nd & 3rd level. Within close proximity to vibrant Linden Square amenities including shopping and restaurants, & tennis & pickle ball courts at Sprague Field. Easy highway access. Please ask listing agent about the possibility of a second space.

16 Stearns Rd Unit 208, Wellesley

Listing courtesy of Listing Agent: Bartlett Albion Group from Listing Office: Hammond Residential Real Estate.
5-7 Abbott Street, Wellesley
$3,400,000
10 Beds ⋅ 9 Baths ⋅ 73445436 MLS
Rare Investment Opportunity in the Heart of Wellesley Square! Offered for the first time in almost 80 years, this exceptional TWO BUILDING/multi-family property is a rare find in one of Metro Boston’s most desirable communities. Situated on a quiet street just steps from vibrant Wellesley Square, this unique offering includes two buildings with a total of 7/8 units, providing excellent long-term income and countless possibilities for the savvy investor or owner-occupant. Live in one unit and let the other units work for you, or hold as a high-performing rental property with significant upside. This is an excellent opportunity to own in a prime Wellesley location — enjoy restaurants, boutique shops, the Commuter Rail, Wellesley College, and the Wellesley Library. Enjoy unbeatable access to Routes 16, 9, 95, and the Mass Pike, making commuting and travel effortless. Whether you're looking to invest, convert, or plant roots in a world-class community, this property delivers!

5-7 Abbott Street, Wellesley

Listing courtesy of Listing Agent: Linda Glennon from Listing Office: Conway - Hanover.

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

How much is your home worth?

Get instant property value now!