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$2,495,000
5 Beds 6 Baths UNDER AGREEMENT Status 73553688 MLS 4,453 SqFt.
Nestled in the prestigious Wellesley Farms neighborhood, this enchanting brick estate is set on over 35,000 square feet of beautiful grounds, offering exceptional privacy and timeless elegance. A grand foyer welcomes you into a thoughtfully designed home featuring five spacious bedrooms and four full bathrooms. Rich architectural details, grand living spaces, and refined finishes create an atmosphere of warmth and sophistication. Generous formal and casual living areas accommodate every lifestyle. Spanning four impressive levels of living space, the home offers remarkable flexibility with ample room for work, recreation, guests, or a private retreat. Expansive windows frame picturesque views of the lush property, seamlessly blending indoor comfort with outdoor beauty. Located in one of Wellesley’s most desirable neighborhoods, this exceptional estate presents a rare opportunity to enjoy gracious living, classic charm, and an extraordinary setting just minutes from town, commuter rail, and top-rated schools.

25 Hillside Rd, Wellesley

$3,250,000
4 Beds 4 Baths ACTIVE Status 73551561 MLS 3,712 SqFt.
Nestled in the heart of prestigious Wellesley Farms, this stately 1930 center entrance Colonial offers timeless curb appeal and an exceptional opportunity to reimagine a classic. Boasting approximately 3,712 square feet of living space, this gracious home features five spacious bedrooms, three full baths, and a convenient half bath. With a solid brick exterior, enduring slate roof, and rock-solid bones, this property exudes old-world craftsmanship rarely found today. While the interior awaits your personal vision and updates, the home's elegant proportions, rich architectural details, and prime location provide an incredible canvas to create your dream residence in one of Wellesley's most sought-after neighborhoods.Sold ASIS. Priced to sell.

25 Hundreds Cir, Wellesley

$839,000
2 Beds 2 Baths CONTINGENT Status 73550145 MLS 1,171 SqFt.
Completely renovated in 2015, this quiet, move-in ready unit in desirable Linden Square Townhomes offers quality craftsmanship, private outdoor space, and a convenient in-town Wellesley location. Hardwood floors, crown molding, updated lighting, and a fireplaced living room with a custom mantel create a warm, inviting space. French doors open to a newly renovated private paver patio, while the rear entrance provides direct access to the assigned parking space. The kitchen features marble countertops, a marble backsplash, custom cabinetry, stainless steel appliances, a wine cooler, and a peninsula with seating. Upstairs offers two spacious bedrooms, an updated full bath with marble flooring, a marble vanity, glass shower enclosure, Toto fixtures, and convenient second-floor laundry. Convenient to Linden Square, shops, restaurants, commuter rail, town fields, tennis courts, and walking paths.

11 Oak Street Unit 33, Wellesley

$1,349,000
3 Beds 3 Baths ACTIVE Status 73549723 MLS 2,140 SqFt.
Welcome to this beautifully newly renovated lakeview home in one of Wellesley's most desirable neighborhoods, just a short walk from Morses Pond. This move-in-ready home features 3 bedrooms, 2.5 full bathrooms, with a bright, open-concept layout ideal for everyday living and entertaining. The sun-filled living room showcases oversized windows with beautiful lake views, while the modern kitchen features stainless steel appliances and seamlessly connects to the main living areas. The second floor offers three generously sized bedrooms, including primary suite, all with hardwood floors. A finished lower level provides flexible space for a playroom, home gym, or media room, with a laundry area and storage. Recent upgrades, high-efficiency HERS Approved, brand-new HVAC system, 2 zone heating and central A/C, upgraded 400-amp electrical, energy-efficient spray foam insulation, and a paved driveway with 6 parkings. Enjoy breathtaking lake views, top-rated schools, and exceptional renovations in this beautiful home

63 Russell Rd, Wellesley

$1,500,000
3 Beds 3 Baths ACTIVE Status 73547678 MLS 2,447 SqFt.
Set on a quiet residential cul-de-sac, this thoughtfully renovated 3-bedroom, 3-bath home offers a host of upgrades designed for effortless everyday living. The kitchen flows naturally into the sun-drenched dining room, where windows on three sides and one of three wood-burning fireplaces add warmth and character to the space. Together they look out over an expansive backyard, where a paver patio and mature landscaping create a private outdoor retreat perfect for entertaining or simply unwinding after a long day. Downstairs, the finished lower level adds tremendous flexibility with a secondary living room, a private office, a full bathroom, ample storage, and direct access to the garage. Close to Wellesley's town center, middle school, and high school, this is a home that truly has it all.

44 Windemere Rd, Wellesley

$1,198,000
3 Beds 2 Baths ACTIVE Status 73547038 MLS 1,813 SqFt.
Location, Location, Location! Lovingly maintained Victorian home on a beautifully landscaped, fenced, level yard. First floor offers bright and inviting living room, dining room with French doors that lead to a large private brick patio, expanded and updated eat-in kitchen, and a large updated half bathroom. Three bedrooms and an updated full bath are located on the second floor. Additionally, there is a flexible bonus room located on the third floor that can be used as an office/playroom or fourth bedroom. This home is ideally situated just minutes from Linden Square, local shops, restaurants, schools, commuter rail, and Wellesley town center, with easy access to major routes and highways.

296 Linden St., Wellesley

$1,895,000
4 Beds 4 Baths UNDER AGREEMENT Status 73546822 MLS 2,695 SqFt.
Timeless charm meets modern comfort in this beautifully maintained 1912 Colonial, offering 8 well-proportioned rooms, including 4 bedrooms and 4 baths (2 full, 2 half). The heart of the home is a beautifully renovated eat-in kitchen with stone counters, custom cabinetry, and stainless appliances, flowing effortlessly out to a generous patio that opens onto a private outdoor space with plenty of room to play and a magnificent beech tree as its centerpiece. Upstairs, the main bedroom features walk-in closets and full bath, alongside three additional bedrooms and a beautifully renovated family bath. The finished lower level adds flexible living space ideal for a playroom, home office, or bonus TV room, complete with a wet bar and half bath. Additional highlights include central air conditioning, an attached garage, and an unbeatable location with easy access to the commuter rail, the Mass Pike, and Rte 95—keeping you close to everything while making commuting a breeze.

25 Riverdale Rd, Wellesley

$1,625,000
3 Beds 3 Baths ACTIVE Status 73546159 MLS 2,212 SqFt.
Come see the perfect blend of sophisticated design and everyday comfort in this stunning 3-bedroom, 2.5-bathroom brick home situated on a picturesque, tree-lined street. The inviting open floor plan is bathed in natural light, accentuating the gleaming hardwood floor running throughout the entire home. A chef’s kitchen on the first floor featuring high-end appliances, custom cabinets, and ample prep space. An elegant French door leads directly from the dining area to a spacious deck for relaxing & entertaining. A sun-drenched space perfect for a quiet home office/sunroom. Primary bedroom on 2nd floor is your private sanctuary featuring a beautiful ensuite bath with heated floor. Two additional well-sized bedrooms offer flexibility for family, guests or hobby rooms. The versatile lower-level finished space provides ultimate setting for a game/exercise room. Enjoy the convenience of "walk-to" living, whether you are commuting via nearby train station or exploring the vibrant town center.

20 Shaw Rd, Wellesley

$1,275,000
3 Beds 3 Baths ACTIVE Status 73545904 MLS 1,848 SqFt.
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

$1,699,900
5 Beds 4 Baths UNDER AGREEMENT Status 73545530 MLS 2,802 SqFt.
Welcome to 18 Benvenue Street! This sun-filled Colonial in the coveted Dana Hall neighborhood offers thoughtful updates and exceptional living space throughout. The open-concept first floor features an updated eat-in kitchen with custom cabinetry, quartz countertops, stainless steel appliances, tiled backsplash, and peninsula, flowing seamlessly into the dining and family rooms. A fireplaced living room, half bath, and spacious laundry room with built-ins complete the main level. Upstairs are four generously sized bedrooms, including a primary suite with a walk-in closet and private bath, plus an additional full bath in the hallway. The finished lower level offers a large gym/playroom, fifth bedroom, and full bath, ideal for guests or extended family. Enjoy the beautifully landscaped backyard with your own private oasis patio and level lawn, perfect for entertaining. Central A/C, one-car garage and newer shed complete this exceptional home.

18 Benvenue Street, Wellesley

$5,995,000
6 Beds 6 Baths ACTIVE Status 73545332 MLS 7,738 SqFt.
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

$1,490,000
4 Beds 3 Baths ACTIVE Status 73542088 MLS 2,218 SqFt.
Meticulously updated and turnkey move in!32 Bobolink Rd combines classic charm with modern conveniences. Recent improvements including a new roof, updated HVAC systems & interior upgrades,unbeatable location close to all the Wellesley top schools, parks, shopping, and commuter routes.Bright and spacious raise ranch house which located on a quiet street. Gleaming hardwood floors , open concept updated kitchen with maple cabinets and granite countertops. The spacious living and dining areas flow effortlessly into a welcoming family room with sliding doors leading to a private patio—perfect for entertaining or relaxing outdoors. Master bedroom comes with a bonus room, two more bedrooms on the 1st level with lots of storage space. Lower level is a finished basement, comes with one more bedroom, full bath, laundry, mudroom and access to the attached two car garages. Fenced in yard, minutes from Schofield Elementery School. Don't miss your chance to make 32 Bobolink Rd your new home!

32 Bobolink Rd, Wellesley

$3,299,000
6 Beds 5 Baths ACTIVE Status 73542007 MLS 4,424 SqFt.
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

$1,088,000
3 Beds 2 Baths UNDER AGREEMENT Status 73541705 MLS 1,521 SqFt.
Nestled on a quiet side street in Wellesley, this charming residence offers the perfect blend of timeless elegance, comfort, and convenience. A great opportunity to enjoy one of Greater Boston's most desirable communities at an attractive price point. Enjoy close proximity to top-ranked Wellesley schools, vibrant shopping & dining, area amenities and it's located less than 1 mile from Wellesley Hills commuter rail station. Home features thoughtfully designed living spaces with efficient floor plan maximizing every square foot, creating warm and welcoming living spaces. Inside, functional spacious living/dining room, beautiful kitchen, 3 bedrooms, 2 full bathrooms, and a home office. Outside, enjoy a private setting with room to relax, garden, or entertain. A detached 2 car garage plus driveway parking space. Whether commuting to the city or working locally, this home provides the perfect balance of accessibility and comfort. Schedule a showing today.

6 Oakland Circle, Wellesley

$2,270,000
5 Beds 5 Baths UNDER AGREEMENT Status 73541195 MLS 4,507 SqFt.
They don't build them like this anymore! Wraparound porch, two staircases, tons of custom millwork, and period details woven into every room. Originally built in 1900, this home was expertly renovated and seriously expanded in 2002. The new kitchen is a showstopper with a beautiful eat-in area flowing into a step-down family room. Then you find the yard. Big, open, and private in a way that feels like a secret this close to town. Formal dining room, sitting room, crafted woodwork throughout, office around the corner. Upstairs the primary suite delivers. Soaring ceilings, bespoke detailing, a bath that holds its own. Four more bright bedrooms, marble counters in every bathroom, laundry up here too. Third floor is a fantastic bonus space for play or work. Finished basement rec room has its own kitchenette, bath, serious storage, and another laundry setup. Great location for easy commutes AND enjoyment of natural spaces with the abutting aquaduct trail, Longfellow Pond and Centennial Park

319 Oakland St, Wellesley

$2,950,000
6 Beds 5 Baths UNDER AGREEMENT Status 73540530 MLS 4,475 SqFt.
Privately sited on a beautifully landscaped 0.65-acre lot in Wellesley’s coveted Dana Hall neighborhood, this exceptional residence offers the perfect blend of elegance, privacy and convenience, just moments from town, Hunnewell Elementary School, WMS & WHS. Designed for both everyday living & entertaining, the main level centers around a beautifully appointed kitchen that flows seamlessly into expansive dining, living, & family rooms. French doors & a serene screened porch open to a generous deck all overlooking the lushly landscaped grounds. A laundry room & powder room complete the 1st floor. Upstairs, the luxurious primary suite features custom built-ins, a walk-in closet, and a spa-inspired bath. Five additional bedrooms and 2 full baths provide ample accommodations, including a private guest or au pair wing. The newly renovated walk-out LL offers flexible space for recreation, fitness, media, or remote work. 2 car garage, plus 2 newly constructed sheds & many recent updates!

10 Colgate Rd, Wellesley

$2,395,000
4 Beds 4 Baths UNDER AGREEMENT Status 73540509 MLS 3,610 SqFt.
Thoughtfully rebuilt & expanded in 2016, this exceptional 4-bedroom, 3.5-bath center-entrance Colonial blends timeless elegance with modern luxury. Designed for today’s lifestyle, the home features a stunning chef’s kitchen with high end appliances, an oversized island and dining area that opens seamlessly to a fireplaced family room with bar—perfect for everyday living & entertaining. A gracious living room with built-ins, private home office, walk-in pantry, mudroom & powder room complete the 1st floor. Upstairs, the expansive primary suite offers custom built-ins, 2 generous closets & a spa-inspired bath w/ soaking tub. Three additional bedrooms, a beautifully appointed double-vanity bath & laundry room complete the 2nd level. The lower level includes a large recreation room, flexible office or gym space & a full bath. 2 car garage. Sited on a beautifully landscaped level lot, this home is moments from Linden Square, Wellesley Hills Commuter Rail, Sprague Elementary, WMS & WHS.

10 Kirkland Circle, Wellesley

$1,485,000
3 Beds 2 Baths UNDER AGREEMENT Status 73539867 MLS 1,835 SqFt.
This charming Bungalow with an inviting front porch complete with a swing, will steal your heart. A gracious foyer leads to a sun-filled open concept living room & kitchen for easy everyday living. The separate dining room is perfect for entertaining. The versatile first floor includes a full bath & laundry room and a bonus room offering flexibility as a home office, guest room, playroom & a mudroom. The 2nd floor has 3 generous bedrooms and a luxurious spa-like bath room featuring double sinks, a soaking tub, & a stall shower. Step outside to enjoy a terrific fenced in backyard and deck—ideal for pets and relaxing summer evenings with family & friends. Perfectly situated a short distance to the vibrant Linden Square shops & restaurants, public schools, and Commuter Train. Experience the best of both worlds, where urban convenience meets the peace, space and charm of the suburbs. It is the home you have been waiting for and one not to miss!

20 Hill Top Rd, Wellesley

$1,495,000
3 Beds 2 Baths UNDER AGREEMENT Status 73539248 MLS 2,300 SqFt.
Don’t Let the Classic Exterior Fool You— This Cape Lives Unexpectedly Large. From the street, it’s a picture-perfect, timeless New England Cape. Step inside, and it transforms into an open flow, sun-drenched sanctuary of modern luxury. This is the ultimate "don't judge a book by its cover" home, meticulously renovated with uncompromising attention to detail. The main level features a fully renovated chef’s kitchen boasting premium appliances, custom cabinetry, a large island, and white oak floors, which flows into a vaulted family room anchored by a gas fireplace that offers a beautiful view of the outdoor oasis. A flexible first-floor footprint provides space for a home office, den, or bedroom. Upstairs features two spacious bedrooms, a versatile third room ideal for a nursery or home office, and a full, modern bathroom. The finished lower level is the ultimate surprise, living like a secondary wing with a massive recreation area, a sunken professional-grade exercise room, and more.

58 Manor Ave, Wellesley

$2,750,000
5 Beds 3 Baths UNDER AGREEMENT Status 73538643 MLS 3,413 SqFt.
Set on a meticulously-landscaped lot in a coveted Wellesley neighborhood, this thoughtfully-renovated colonial offers the perfect blend of timeless design, expertly-crafted details and modern updates. Designed for everyday living and effortless entertaining, the first floor features an open floor plan with a living room, family room and a renovated, eat-in kitchen with Wolf + Subzero appliances. A generous mudroom and half bath complete this level. Upstairs is a serene primary suite with a stunning bath and two walk-in closets. There are four generous bedrooms, a renovated full bath and laundry also on this floor. The recently-finished lower level has excellent recreation space and a gym with an epoxy floor. The private grounds extend the living space offering a bluestone patio, lush yard and fire pit, ideal for outdoor entertaining and enjoyment. Close to Wellesley's top-rated schools, vibrant town center and amenities, commuting routes and more, your dream home awaits.

23 Northgate Rd, Wellesley

$1,395,000
3 Beds 2 Baths ACTIVE Status 73537936 MLS 1,640 SqFt.
Lovely Cottage on Morses Pond with stunning 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. Take in the tranquility of this special home.

30R Morses Pond Road, Wellesley

$2,295,000
4 Beds 3 Baths UNDER AGREEMENT Status 73536634 MLS 4,799 SqFt.
Nestled on a tranquil tree-lined street, this sun-filled expanded & spacious Cape will impress you at every turn! The front porch surrounded by lush landscaping is the perfect spot for morning coffee or lazy afternoons. When you step inside you will be amazed by the amount of living space. The open concept family room includes a wall of windows highlighting the scenic view, a magnificent stone fireplace & leads to the newly renovated stylish kitchen; creating an airy atmosphere for family gatherings. Relax, read & work from home in the beautiful library with soaring ceiling & custom built-ins. Rare first floor bedroom is ideal for guests/ au-pair. The second floor has the primary bedroom w/ a dressing room, full bathroom w/ double vanity & two additional bedrooms & full bath/ laundry. Fantastic lower level is a surprise with a playroom, game room & bonus room- wow! Outdoor setting is a nature lovers dream with lovely views & patio for entertaining. Beloved neighborhood near Perin Park.

99 Parker Road, Wellesley

$2,150,000
5 Beds 3 Baths CONTINGENT Status 73536258 MLS 2,628 SqFt.
Gracious Victorian w/an incredible Barn & workshop, a distinctive property zoned GR offering unmatched versatility. The inviting front porch sets the tone of warmth & charm of this beautifully renovated home brimming w/vintage details such as stain glass windows, turned staircase & 9' ceilings. Gorgeous chef's kitchen w/white shaker cabinetry, 2 copper sinks, high-end appliances, quartz & large center island for gathering. The expansive family & living rm w/cozy fireplace offers plenty of space for entertaining. 2nd floor has a home office and 3 bedrooms including a luxurious spa-like bath. The 3rd floor has a generous 4th bedroom or bonus room. Enjoy summer BBQs on the stone patio. There a garage plus extraordinary barn w/a heated workshop & room enough for 6 cars. Studio apartment at ground level w/a separate entrance & patio. Own a part of Wellesley's history. Conveniently located near the train, town center, schools, restaurants & more, all the best of Wellesley!

33 Linden Street, Wellesley

$1,925,000
4 Beds 3 Baths ACTIVE Status 73533550 MLS 2,896 SqFt.
Presenting this extraordinary, beautifully updated 1800s modern farmhouse in highly convenient Wellesley Hills. Privately set on a tucked-away lane w/ minimal traffic yet just a short walk to the train, shops & restaurants, this unique home features high ceilings, lovely appointments & a wonderful sense of connection throughout. A welcoming front porch & foyer open to sun-filled living spaces including a family room off the kitchen perfect for everyday living & entertaining. Dining & living rooms are enhanced by fireplaces & crown moldings. The primary suite offers a serene retreat w/ a stylish newer bath. Three additional bedrooms & second floor laundry. Wonderful, spacious living space above the 2-car garage provides versatility for home office, gym, studio, or possible ADU. Relax on the porches, patio & grounds—a special home that must be experienced in person.

40 Kimlo Rd, Wellesley

$2,500,000
4 Beds 5 Baths UNDER AGREEMENT Status 73533506 MLS 2,998 SqFt.
Set on a naturalized landscaped oversized lot in a sought-after Wellesley location, this sun-filled Arts and Crafts residence blends timeless character with refined versatility. Thoughtfully expanded with custom architectural details, the home offers primary suites on both the first and second floors, generous additional bedrooms and baths, and flexible spaces for work, guests, or quiet retreats. Skylights, fireplaces, and vaulted ceilings bring warmth, light, and scale throughout, and the landscaped grounds and specimen plantings complete the setting.•4 bedrooms, including primary suites on both the first and second floors•3 full baths and 2 half baths•Skylights, fireplaces, and vaulted ceilings throughout•Thoughtful expansion featuring custom architectural details•Spacious two-car garage with attached workroom•Lower level provides generous storage and oversized playroom •Outdoor patio. Plant lovers paradise . Near Town center/Dana Hall, Hunnewell School, library. West facing sunsets.

42 Temple Road, Wellesley

$3,195,000
5 Beds 6 Baths ACTIVE Status 73530659 MLS 5,735 SqFt.
Completely reimagined, this exceptional 5,700+ sq ft residence is ideally situated on a quiet residential loop just steps from top-ranked Wellesley schools, Linden Square, commuter rail, Whole Foods, and parks. Designed for modern living, the home features sun-filled open-concept spaces, seamless indoor-outdoor flow, and beautifully connected kitchen, wet bar, and family room overlooking a level backyard surrounded by mature trees with a private feel that's rare this close to town. The impressive primary suite offers soaring ceilings, a private terrace, dual walk-in closets, and a spa-inspired bath, while generously scaled bedroom suites provide exceptional flexibility for work, study, and relaxation. A spectacular lower level with kitchenette, theater, lounge, fitness, and recreation areas creates the ideal setting for entertaining and everyday living. Turnkey throughout, this is a rare opportunity to enjoy walkable in-town living without sacrificing space, privacy, or modern comfort.

31 Alba Rd, Wellesley

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