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340 Weston Road, Wellesley
$1,650,000
5 Beds ⋅ 4 Baths ⋅ 73593846 MLS
Welcome to 340 Weston Road. Set well back from the road on 1+ acre, this classic 1998 Colonial offers the space, scale, and setting that are increasingly hard to find in Wellesley. With 11 rooms, 5 bedrooms, and 3.5 baths across 4,420 square feet, the home is ready for its next owner to bring their own vision to life. The main level features oversized rooms and a traditional layout, with formal living and dining rooms for entertaining and a fireplace for cozy nights. A two-car attached garage with direct entry makes everyday living easy. Upstairs are all 5 bedrooms, including two en suite bedrooms and three additional well-proportioned bedrooms. A walk-up third floor room provides flexible space for an office, studio, or retreat, and the full basement offers room to expand. In original condition, the home presents a rare chance to personalize a substantial Colonial on over an acre, without starting from the ground up. Central air, natural gas heat, and a spacious footprint provide a strong foundation for your plans. Conveniently located near the Hardy Elementary School, highways, Morses Pond, Whole Foods Market, and the commuter rail. 340 Weston Road is the opportunity to create your own vision of home in Wellesley, with all that this exceptional town has to offer.

340 Weston Road, Wellesley

Listing courtesy of Listing Agent: Migdol Moore Team from Listing Office: Gibson Sotheby's International Realty.

80 Washington Street, Wellesley
$9,500
5 Beds ⋅ 4 Baths ⋅ 73589351 MLS
Exceptional Indoor & Outdoor Living in the Heart of Wellesley HillsDiscover the perfect blend of space, comfort, and convenience in this beautifully situated 5-bedroom, 4-bath home in sought-after Wellesley Hills. Offering generous, sun-filled living spaces and exceptional outdoor amenities, this home is ideally suited for today's lifestyle, with flexible accommodations for family, guests, home offices, and entertaining.The thoughtfully designed layout features multiple living and gathering spaces, including an additional second-floor family room and the convenience of second-floor laundry. Five spacious bedrooms offer versatility, while the finished lower level provides additional room for recreation, fitness, or play. Abundant storage and a dedicated workshop adds everyday practicality.A standout feature is the expansive outdoor living area, creating a seamless extension of the home and an inviting setting for alfresco dining, entertaining, or simply relaxing in a private outdoor retreat.Ideally located in one of Wellesley's most desirable neighborhoods, the home is just moments from Warren Playground and Recreation Center, the Crosstown Trail, and the iconic Boston Marathon route. Enjoy easy access to Wellesley Hills shops and restaurants, commuter rail, the T, and major commuting routes, offering the perfect balance of suburban living and accessibility to Boston.An exceptional rental opportunity offering the space, flexibility, outdoor lifestyle, and prime location that make Wellesley Hills so desirable.

80 Washington Street, Wellesley

Listing courtesy of Listing Agent: Donna Scott Group from Listing Office: Coldwell Banker Realty - Wellesley.

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.

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.

3 Macarthur Rd, Wellesley
$2,995,000
5 Beds ⋅ 4 Baths ⋅ 73578376 MLS
Located in Wellesley’s highly desirable Generals neighborhood, this distinguished Colonial welcomes you with an elegant foyer, spectacular three-story staircase, and beautiful hardwood floors throughout. The thoughtfully designed floor plan features five bedrooms, three full baths, one half bath, and a convenient second-floor laundry room. At the heart of the home is a spacious open-concept kitchen and living area, creating a warm and inviting setting for everyday living and entertaining. A comfortable den and formal dining room provide additional spaces for relaxing and gathering. The home also offers two versatile bonus rooms, currently used as a home gym and TV room, providing flexible space for a home office, playroom, media room, exercise space, or other needs. The deck extends the living space outdoors and is ideal for relaxing or entertaining. A two-car garage provides convenient parking and additional storage, while the unfinished basement offers substantial storage and potential for future use. The location is a standout feature, just minutes from Hardy Elementary School, Wellesley Middle School and Wellesley High School. The home is also conveniently located near the Wellesley commuter rail station, providing easy access for Boston-area commuters. Combining classic Colonial character, generous living space, flexible bonus rooms, and a convenient location in one of Wellesley’s established neighborhoods, this home offers a wonderful opportunity to enjoy all that Wellesley has to offer.

3 Macarthur Rd, Wellesley

Listing courtesy of Listing Agent: Cynthia Hatch from Listing Office: William Raveis R.E. & Home Services.

21 Elmwood Rd, Wellesley
$2,395,000
5 Beds ⋅ 4 Baths ⋅ 73576607 MLS
Bates Elementary is on this street. Start there, then walk the half acre. Level, fenced and private, reworked in 2020 under a plan by Duckham Architecture and Interiors with a new fieldstone wall, walkways on both sides, irrigation, underground water management and expanded driveway. The house is a 1940 colonial that was expanded and re-sided the same year by Duckham Architecture and Interiors. New siding, windows and gutters on every side. An extra-large farmer's porch across the front. A new side entry where the bulkhead used to be. And a four-season room with a cathedral ceiling and glass on three sides, opening to a landing deck and bluestone patio. Inside, a twenty five foot eat-in kitchen with a Wolf range, double wall ovens, Sub-Zero wine refrigeration, custom cabinetry and a built-in banquette that seats eight. The living room has a fireplace and a wall of built-ins. The family room has a brick fireplace and a bay window. Upstairs, the primary suite occupies its own wing, with a fireplace, a step-up sitting room that doubles as an office, a walk-in closet, and a bath with a double vanity and a tiled walk-in shower. The lower level was rebuilt in 2014 and extended in 2020. Daylight windows, its own heating and cooling, a fifth bedroom, a second sitting room, a full bath, laundry, and an exercise room with direct outside access. Ideal for guests, an au pair, a parent, or a teenager who wants a floor of their own. New roof 2014. Fresh interior paint 2026. Gas heat, central air, 200-amp service. A short walk to the commuter rail and Linden Square.

21 Elmwood Rd, Wellesley

Listing courtesy of Listing Agent: Declan O'Toole from Listing Office: SelectRE Boston.

41 Longmeadow Road, Wellesley
$2,995,000
5 Beds ⋅ 4 Baths ⋅ 73573823 MLS
Enjoy the beauty and serenity of the picturesque Longmeadow setting in this stunning Colonial! Offering an exceptional open-concept layout, streaming with natural light & thoughtfully designed, renovated & expanded for today’s modern living- this home has it all! The expansive gathering spaces seamlessly connect the chef’s kitchen, sun-filled family room & elegant dining areas, creating the perfect backdrop for everyday living & entertaining alike. Walls of windows frame sweeping view of the gorgeous grounds & patios. A luxurious primary suite provides a peaceful retreat, while four additional bedrooms offer flexibility for family and guests. Across multiple levels, the home blends timeless architectural detail with contemporary comfort, including a gracious foyer, home office, mudroom and a fabulous lower level with a playroom and exercise area. Set in one of Wellesley's most admired neighborhoods this property offers rare proximity to walking trails, the new Hunnewell school & town.

41 Longmeadow Road, Wellesley

Listing courtesy of Listing Agent: The Lara & Chelsea Collaborative from Listing Office: Coldwell Banker Realty - Wellesley.

9 Fells Circle, Wellesley
$1,730,000
5 Beds ⋅ 4 Baths ⋅ 73573624 MLS
Welcome to 9 Fells Circle, a beautifully updated home offering bright, spacious, and flexible living in a desirable Wellesley neighborhood. Featuring hardwood floors, a fireplaced living room, formal dining room, spacious family room, updated kitchen and baths, and central air. The unique multi-level layout provides comfortable separation between living and sleeping spaces.The spacious primary bedroom features a finished bonus/flex space just a few steps up, perfect for a private home office, fitness area, sitting room, or additional flexible living space. Generously sized bedrooms, a beautiful yard, and an attached garage complete the home. Conveniently located near Wellesley schools, shopping, dining, and major routes. First showings at the Open Houses this Saturday and Sunday!

9 Fells Circle, Wellesley

Listing courtesy of Listing Agent: Qian Han from Listing Office: JW Real Estate Services, LLC.

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.

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.

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.

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