Wellesley, MA Real Estate Search

Wellesley, MA 4 Bedroom Homes for Sale

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Newest Wellesley, MA 4 Bedroom Homes for Sale

18 Woodlawn Ave, Wellesley
$11,000
4 Beds ⋅ 3 Baths ⋅ 73593580 MLS
This Wellesley Farms gem is ideally situated close to local shops, schools, the commuter rail, parks & playgrounds making it easy to enjoy all the conveniences that Wellesley has to offer. Bathed in natural sunlight, this fabulous four-bedroom home offers the perfect blend of comfort, charm, and everyday convenience. Sun-filled interiors create a warm and inviting atmosphere, with bright, welcoming spaces ideal for both relaxed family living and entertaining. Thoughtfully designed to accommodate today’s lifestyle, the home offers four well-proportioned bedrooms, sun filled home office and fabulous finished lower level wonderful for get away space. The fenced backyard provides a private outdoor retreat, perfect for summer gatherings, outdoor dining, play, and quiet moments of relaxation.

18 Woodlawn Ave, Wellesley

Listing courtesy of Listing Agent: The Lara & Chelsea Collaborative from Listing Office: Coldwell Banker Realty - Wellesley.
11 Poplar Road, Wellesley
$2,795,000
4 Beds ⋅ 5 Baths ⋅ 73590649 MLS
Morning coffee on the front porch, evenings by the fire, and summer dinners on the patio—discover a home that makes everyday living feel special in Wellesley’s convenient College Heights neighborhood. Built in 2009, this custom Colonial pairs high ceilings and hardwood floors with inviting spaces to gather and unwind. At its heart, a spacious eat-in kitchen with an island opens to the fireside family room, with direct access to the bluestone patio and private backyard. A gracious living room and wainscotted dining room set the scene for entertaining, while a dedicated office with built-ins provides a welcoming place to work. Upstairs, the primary suite offers a private bath and walk-in closet. Three additional bedrooms include one with an en-suite bath and two sharing a connecting bath. Second-floor laundry adds everyday convenience. The finished lower level, complete with a full bath, offers flexible space for recreation, exercise, or movie nights. An expansive unfinished third floor presents possibilities for future expansion. With four bedrooms, four full baths, a half bath, and an attached two-car garage, this extraordinary home brings together comfort, flexibility, and access to Wellesley’s shops, schools, and commuter rail. Come experience how beautifully life can flow here.

11 Poplar Road, Wellesley

Listing courtesy of Listing Agent: The Wilson Group from Listing Office: Compass.
42 Sheridan Rd, Wellesley
$1,980,000
4 Beds ⋅ 3 Baths ⋅ 73587697 MLS
Welcome to this timeless New England Colonial, perfectly situated in one of Wellesley's most sought-after neighborhoods. Filled with natural light, the main level offers an inviting living room, elegant dining room, spacious kitchen with a sunny breakfast nook, and an expansive family room that opens effortlessly into a beautiful four-season sunroom overlooking the private backyard. Upstairs, the impressive primary suite features a vaulted ceiling, walk-in closet, spa-inspired bath, and a peaceful sitting area. Three additional generously sized bedrooms, a full bath, and a convenient second-floor laundry room complete the upper level. The finished lower level provides an oversized recreation room along with excellent storage space. Surrounded by mature landscaping, abutting conservation land and 3.3 miles of trails. Ideally located in close proximity to top rated Fiske elementary school, parks, shopping, dining, and major commuter routes.

42 Sheridan Rd, Wellesley

Listing courtesy of Listing Agent: Aphrodite Karpouzis from Listing Office: Gibson Sotheby's International Realty.
31 Alba Rd, Wellesley
$2,495,000
4 Beds ⋅ 6 Baths ⋅ 73586180 MLS
Sophisticated, modern living in the heart of one of Wellesley’s most beloved neighborhoods! Completely reimagined through a comprehensive 2023 renovation, this exceptional 5,700+ sq. ft. Colonial offers the rare combination of privacy, generous living space, and exceptional walkability to top-ranked schools, Linden Square, Wellesley Hills Commuter Rail and all of Wellesley’s wonderful amenities. The sun-filled interior offers an effortless flow, beginning with a gracious formal fireplaced living room, an elegant dining room and an ideal work from home private office with custom built-ins. At the heart of the home, the renovated kitchen features upgraded appliances, two dishwashers, an expansive island and a generous dining area with direct access to a covered deck and the private backyard. A stylish bar / butler’s pantry connects the kitchen to the spacious family room, creating a seamless setting for both relaxed daily living and entertaining. A full bath, powder room, and mudroom, with direct access to the garage, complete the first floor. Upstairs, the impressive primary suite is a private retreat with soaring ceilings, two walk-in closets, a beautifully renovated spa-inspired bath, and its own private terrace. A second ensuite bedroom features a bonus room ideal for a second in-home office. Two additional generous bedrooms, a full bath with a double vanity, and a dedicated laundry space complete the second level. The expansive, finished lower level significantly extends the home’s versatility featuring a bonus room with a bar and kitchenette, fitness space, and rooms for recreation, play, or additional work-from-home needs. Outside, the level private yard is surrounded by mature trees creating an unexpected oasis just minutes to town. A large deck extends your living space outdoors with ample room for entertaining, relaxing, and play. Turnkey and beautifully updated throughout, this distinctive home delivers the space and privacy of a suburban retreat with the convenience of true in-town Wellesley living.

31 Alba Rd, Wellesley

Listing courtesy of Listing Agent: Beyond Boston Properties Group from Listing Office: Compass.
28 Jefferson Rd, Wellesley
$3,080,000
4 Beds ⋅ 4 Baths ⋅ 73584443 MLS
Be prepared to fall in love with this custom Colonial, beautifully sited on landscaped grounds with a private backyard in Wellesley’s Sheridan Estates neighborhood. Masterfully designed and crafted, the home offers nearly 5,000 sq. ft. of living space and the rare convenience of an elevator serving all three levels. A gracious two-story foyer with wainscoting opens to elegant living and dining rooms with 9-foot ceilings. The chef’s kitchen with custom cabinetry opens to a sun-filled family room with soaring cathedral ceiling, oversized windows and gas fireplace. A handsome library and powder room complete the first floor. Upstairs, the serene primary suite features a tray ceiling, generous walk-in closet, luxurious marble bath, along with three additional bedrooms with oak flooring and a second marble bath.The finished lower level offers flexible recreation space, extensive built-in storage and a full bath, with potential for an additional bedroom. Just 12 miles from Boston, this beautifully maintained home offers exceptional privacy and convenience in a sought-after Wellesley setting.

28 Jefferson Rd, Wellesley

Listing courtesy of Listing Agent: The Joni Shore Group from Listing Office: Douglas Elliman Real Estate.
29 Cottage Street, Wellesley
$6,500
4 Beds ⋅ 4 Baths ⋅ 73584265 MLS
Set on charming Cottage Street in Wellesley’s historic district, this 19th-century Colonial brings together old-world character, a private backyard retreat and flexible space to work from home. The Brook Path is moments away, while Wellesley Square’s boutiques, restaurants, and commuter rail station are less than a mile from the property.The four-bedroom main house offers wood floors, a fireplace, a sunroom, a main-level bedroom and three full baths. Outside, a deck overlooks the fenced yard and in-ground pool. The separate pool house offers space for an office or studio, plus a fourth full bath for poolside convenience.Enjoy mornings along the Brook Path, dinner in the Square, and afternoons by the pool, all from a home on one of Wellesley’s most appealing historic streets. The property is in the Hunnewell Elementary School district. 6- or 18-month lease options are available and the seller is open to discussing a purchase. Some photos contain virtual staging.

29 Cottage Street, Wellesley

Listing courtesy of Listing Agent: Ayme Van Riet from Listing Office: Compass.
150 Pond Road, Wellesley
$4,395,000
4 Beds ⋅ 6 Baths ⋅ 73580323 MLS
Truly one of kind property nestled in renowned Hunnewell Estates with horses and cows with the feel of Vermont yet close to Wellesley Center. 3 acres of a private sanctuary surrounded by conservation land and trails.. Incredible opportunity in Wellesley to have gardens, fruit trees, chickens... Gorgeous outdoor space with fire pits, zen waterfall, vegetable gardens with hand hewn raised beds from trees on the property. Orchard with 30 fruit and nut trees, 10 sugar maples for maple sugaring, herb garden, fragrance garden and chicken coop with run. Over 7200 sq ft of living on 3 levels. First floor main bedroom with full bath and double walk-in closets. Spa-glass conservatory off the main bedroom with built-in hot tub. Both a library and 2nd office off the main bedroom each with custom woodwork and built-ins. Large fireplaced living room with French doors along entire rear. Dining room perfect size for entertaining. Custom kitchen with large island and show stopping gorgeous stone fireplace that opens to the family room. Mudroom and laundry room complete the first floor. Perfect guest suite over the garage. Second level consists of and additional 2 large beds with walk-in closets and full bath. Lower level with large game room including a wet bar and media area. Additional playroom plus 2 more rooms with bath perfect for guests. 3 car garage. A must see!

150 Pond Road, Wellesley

Listing courtesy of Listing Agent: Melissa Dailey from Listing Office: Coldwell Banker Realty - Wellesley.
8 Tennyson Rd, Wellesley
$2,795,000
4 Beds ⋅ 4 Baths ⋅ 73579886 MLS
Located in one of Wellesley’s most sought-after neighborhoods, this handsome 1924 Colonial offers the timeless character of its era paired with an exceptional floor plan and outdoor spaces that are truly special. From the moment you arrive, the original architectural details and craftsmanship are evident, giving the home a warmth and sense of character that is increasingly difficult to find. The first floor is thoughtfully designed for both everyday living and entertaining, with generously proportioned rooms and a seamless connection to the outdoors. A recently expanded deck, accessible from both the family room and living room, creates an ideal setting for summer dinners, morning coffee, or gathering with friends. Beyond it, the expansive backyard is an uncommon feature for this neighborhood—beautifully private, unusually spacious, and offering wonderful possibilities for outdoor living, recreation, and play. The second floor offers four bedrooms, including a generously sized primary suite with an updated bath and ample closet space. An oversized guest suite provides additional comfort and flexibility for family or visitors. The lower level adds another dimension of versatility with a full bath and flexible finished space that can easily accommodate a bedroom suite, home office, playroom, gym, or recreation area. An oversized garage is an exceptional bonus, offering additional space that could serve as a home gym, workshop, hobby area, or simply provide abundant storage. A rare combination of location, character, privacy, and flexible living space, this home offers the opportunity to enjoy all that makes this Wellesley neighborhood so desirable while having an outdoor setting that feels remarkably private and expansive.

8 Tennyson Rd, Wellesley

Listing courtesy of Listing Agent: Donahue Maley and Burns Team from Listing Office: Compass.
99 Pond Road Unit 99, Wellesley
$11,500
4 Beds ⋅ 5 Baths ⋅ 73578306 MLS
A truly exceptional offering, this private estate is one of Wellesley's most remarkable properties. Set on more than 10 breathtaking acres overlooking Lake Waban, this historic residence dating to 1732 offers an extraordinary combination of privacy, natural beauty, and timeless New England charm that is rarely available. With nearly 4,000 square feet of living space, the residence features a large open kitchen with French doors leading to the patio, pantry, large living room, formal dining room, library, 4 bedrooms, 3 full baths, 2 half baths and 8 fireplaces. Rich in period detail throughout, the home showcases craftsmanship and charm of a bygone era while modern updates throughout create spaces for everyday living and entertaining. Outside, beautifully landscaped gardens, an inviting stone patio and walking paths create a peaceful retreat. Stroll through the grounds, enjoy the changing seasons, or follow the trails around Lake Waban. Surrounded by natural beauty yet just minutes from Wellesley Center, top-rated schools, commuter rail service, and Boston, this remarkable property is a rare offering that blends history, elegance, and an exceptional lifestyle in one of Wellesley's most coveted locations.

99 Pond Road Unit 99, Wellesley

Listing courtesy of Listing Agent: Eleanor Bright from Listing Office: Berkshire Hathaway HomeServices Commonwealth Real Estate.
49 Cottonwood Road, Wellesley
$7,400
4 Beds ⋅ 4 Baths ⋅ 73569683 MLS
Gorgeous single-family residence in one of the nicer areas of Wellesley. Close to Whole Foods and Linden Square! Recently renovated, with 4 bedrooms & 4 full bathrooms. Its prime location speaks volumes, located just steps from public schooling and parks; this home has clearly defined living and dining spaces. Enormous family room addition with cathedral ceilings that lead out to a beautiful deck overlooking the homes beautifully landscaped grounds or down to a spacious au pair suite.

49 Cottonwood Road, Wellesley

Listing courtesy of Listing Agent: Ryan Drowne from Listing Office: Coldwell Banker Realty - Boston.
560 Worcester St, Wellesley
$1,349,000
4 Beds ⋅ 3 Baths ⋅ 73566903 MLS
Welcome to this inviting 4 bedroom, 2.5 bath home featuring a desirable open floor plan. The updated kitchen with high end appliances, showcases quartz countertops, a spacious island, and a seamless connection to the living areas, creating an ideal space for both daily living and entertaining. A generous dining room sits just off the kitchen and family room, offering an easy layout for gatherings with friends and family. Upstairs, you’ll find three well-sized bedrooms and two full baths, including a serene primary suite with marble bath. The expansive backyard provides a private outdoor retreat with ample space for recreation, dining, and relaxation. The landscaped setting enhances the outdoor experience while maintaining a sense of privacy. Thoughtfully designed and move-in ready, this home blends comfort, versatility and indoor-outdoor living. Conveniently located near shops, restaurants, commuter rail, and major highways for an easy commute into Boston! Come see all this home has to offer and discover this great opportunity to make it your own.

560 Worcester St, Wellesley

Listing courtesy of Listing Agent: Debi Benoit from Listing Office: William Raveis R.E. & Home Services.
29 Cottage Street, Wellesley
$1,650,000
4 Beds ⋅ 4 Baths ⋅ 73562667 MLS
Opportunity knocks for home-owners and builders alike! Nestled in the heart of Wellesley’s coveted Historic District on prestigious Cottage Street, this picturesque 1870s New England Colonial offers a blend of timeless historic character with unmatched expansion opportunity in a highly sought-after location. The main home offers 4 beds, 3 baths, and an incredible canvas for a buyer ready to bring their personal touch, or execute a complete vision without paying for someone else’s cosmetic choices.Step outside to discover a secluded backyard retreat built for relaxation and entertaining. A fabulous deck overlooks the private, fenced-in yard, and a dedicated pool house completes the oasis with the 4th bath, providing ultimate convenience for guests and poolside gatherings.What truly sets this residence apart is the substantial planning already secured for the next owner: the property comes with an approved 2025 Historic District Commission (HDC) Certificate of Appropriateness for a stunning custom expansion designed by renowned Royer Architects, allowing you to bypass the lengthy municipal review process and move straight toward building equity.The location delivers ultra-easy lifestyle access to the best of Wellesley: you are just steps from the scenic Brook Path for morning walks and a pleasant stroll from Wellesley’s vibrant town center with boutique shopping, top-tier dining, and the commuter rail station. Situated in the highly sought-after, state-of-the-art HUNNEWELL Elementary School district.Whether you choose to move in, refresh the interiors, or build out the approved expansion, this home represents a rare chance in an unbeatable neighborhood.

29 Cottage Street, Wellesley

Listing courtesy of Listing Agent: Paula Carens from Listing Office: Paula Carens.
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.
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