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luxury houses for sale Milton, United States

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28

House with garden and terrace Milton (United States)

This wonderful Milton single family home is truly a classic, with seemingly endless features and updates showing true pride of ownership. It all starts with incredible curb appeal and a wide, updated front porch with composite decking, leading directly into a spacious foyer. The main living level offers high ceilings and great natural light throughout. Large living room connected to dining area with built in cabinet. Thoughtfully updated kitchen and half bath for guests. French doors provide easy access to the private rear deck, massive yard and garage. On the upper floors, this home offers four full bedrooms, with the opportunity to finish additional attic area on the third floor for a 5th bedroom or office area. While this turn key home is truly exceptional, the location simply can't be beat. Amazing neighborhood, with easy access to Milton Village, the Red Line Extension, commuter rail, and so much more!

… 
$799,000
4bedrooms
2bathrooms
land 526

By Gibson Sotheby's International Realty

Contract pending
36

Property Milton (United States)

Highly desirable East Milton Square location on a picturesque tree-lined street. This well-maintained 3 bedroom, 2 bathroom Colonial offers a light-filled interior with hardwood floors throughout and timeless charm. The updated kitchen features white cabinetry, stainless steel appliances, gas cooking, and a wine fridge, while the mudroom adds everyday convenience. Built-ins and a wood-burning fireplace enhance the home’s warmth and character. Enjoy relaxing on the inviting farmer’s porch or entertaining in the fenced backyard with a paver patio. Ideally located near highways, shopping, restaurants, Boston, and Milton’s highly regarded public school system, making this an excellent commuter location.

… 
$949,900
3bedrooms
2bathrooms
land 486

By Gibson Sotheby's International Realty

27

Property with garden Milton (United States)

Majestic and truly one of a kind, this exceptionally private equestrian estate is nestled behind gates within the Blue Hills Reservation, offering direct riding access to over 7,000 acres of protected landscape and year-round outdoor pursuits. Set on more than eight tree-lined acres, the grand compound includes a masterfully constructed main residence, carriage house, expansive garage, and beautifully appointed stables. Designed for both refined living and effortless entertaining, the home features a stunning chef’s kitchen, a soaring vaulted great room with an impressive fireplace and hearth, and seamless indoor-outdoor flow to a covered outdoor kitchen and generous fire pit terrace beneath the stars. Located moments from the prestigious Milton Academy and within easy reach of both Boston and Providence, this extraordinary offering delivers rare privacy, scale, and sophistication in a setting that is simply unparalleled.

… 
$11,900,000
5bedrooms
7bathrooms
land 3.3ha

By Gibson Sotheby's International Realty

27

House Milton (United States)

Perched atop prestigious Milton Hill and set on nearly an acre of beautifully landscaped grounds, this extraordinary estate offers over 7,100 square feet of refined living space. A dramatic atrium foyer welcomes guests into elegant interiors featuring rich hardwood floors, soaring ceilings, and exceptional craftsmanship throughout. Designed for both grand entertaining and everyday living, the home includes a chefs kitchen, wood-paneled library, media room, and temperature-controlled wine cellar. The luxurious primary suite serves as a private retreat with natural light and a spa-inspired bath, while four additional bedrooms provide ample space for family and guests. Outdoors, a resort-style setting awaits with a sparkling pool, cabana, expansive patios, and manicured grounds ideal for entertaining or relaxation. Complete with a three-car garage and offering the perfect balance of privacy and convenience, this residence is just minutes from Boston, renowned schools, and amenties. Granite Avenue to Adams Street. Granite post out front of driveway with house number 263.

… 
$3,095,000
697
4bedrooms
4bathrooms

By Annonceur International

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30

House with pool Milton (United States)

A rare and private Blue Hills retreat set on 2.6 wooded acres abutting conservation land, approached by a winding drive. Designed for those who value privacy and refined living, this exceptional property offers a peaceful escape just minutes from Boston and major routes. The beautifully renovated residence features 4 bedrooms and 2.5 baths, including a luxurious first-floor primary suite with a spa-style bath, custom cabinetry/closets and attached sunroom, perfect for quiet mornings and serene evenings. Elevated finishes and craftsmanship are showcased throughout, highlighted by a chef's kitchen with Wolf double oven, built-in Miele coffee machine and striking marble and custom concrete countertops. Three bedrooms upstairs offer flexibility. The estate includes a detached 3-car barn-style garage with game room, plus a newly built garage connected by a slate-accented portico. A heated in-ground pool and cabana complete this private, resort-like setting. A truly exceptional offering.

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$2,725,000
293
4bedrooms
2bathrooms

By Annonceur International

30

House with pool Milton (United States)

This spacious 9-room home on Hillside Street offers 4 bedrooms in one of Milton's most coveted settings, nestled at the edge of the Blue Hills Reservation. With miles of trails, open space, and stunning natural scenery right outside your door, the location is truly special. The generous layout gives buyers real flexibility to update and personalize, with good bones and a highly desirable address to build from. The property includes a pool currently in need of repair, presenting a great opportunity to create a standout outdoor space on your own terms. Milton is known for its excellent schools, beautiful neighborhoods, and easy access to Boston, and Hillside Road delivers all of it. For a buyer with vision and an eye for value, this is a rare chance to put your stamp on a property where nature and neighborhood come together beautifully.

… 
$1,200,000
207
4bedrooms
1bathroom

By Annonceur International

15

Contemporary house Milton (United States)

Set along one of Miltons most distinguished streets, this Modern Victorian residence blends timeless architecture with refined contemporary living. A classic silhouette, steep gables, and deep porch welcome you home, while 5,600 square feet above grade unfold with intention and warmth. Sunlight pours through tall windows into gracious living spaces designed for gathering and quiet retreat alike. Mornings begin in a kitchen both beautiful and inspiring, anchored by custom detailing, curated finishes, and a hidden pantry. Imagine evenings cozied up in the library or beside the lounging in the family room. Upstairs, the primary suite offers a private escape with a remarkable dressing room, while additional bedrooms provide comfort and flexibility. A third-floor retreat invites creativity, work, or play beneath cathedral ceilings. Set on nearly 0.6 acres, this is a home meant to be lived in slowly and beautifully. Use GPS

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$3,499,000
520
5bedrooms
4bathrooms

By Annonceur International

10

House with pool and garden Milton (United States)

Experience unparalleled scale in this reimagined nearly 5,000 sq. ft. ft. Split-Colonial conversion. Fully renovated within the last 5 years, this estate sits on a rare 1-acre corner lot near Wollaston Country Club. The exterior shines with premium Hardie Board siding, a new roof, and high-efficiency windows. Inside, a chef's kitchen features a 12-foot waterfall quartz island and professional Thermador appliances. The layout seamlessly integrates a split-entry with a massive two-story Colonial addition, offering a sun-drenched great room and expansive family room. An entertainer's dream, the home boasts Sonos in-ceiling speakers throughout, a lower-level wet bar, and a versatile gym space. The backyard is a private resort featuring an in-ground pool, custom paver patio, fire pit, and an architectural 30 ft. Trex deck with a built-in Weber grill. Minutes from Blue Hills and top schools, This home combines massive living space with a pristine outdoor sanctuary. A true turn-key masterpiece.

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$2,399,999
443
4bedrooms
3bathrooms

By Annonceur International

30

House Milton (United States)

Set down a meandering, tree-lined drive, this spectacular turn-of-the-century Manor estate in Milton is a truly rare offering. From the moment you step into the welcoming foyer, elegance abounds. Three gracious floors of seamless living provide an exceptional balance of grand scale and warmth, featuring multiple bedroom suites and generous gathering spaces designed to accommodate both everyday living and memorable entertaining. This is a home where families gather, laughter fills the rooms, and life's most cherished moments are made. A true architectural gem, the residence showcases exquisite period details including thick dentil moldings, rich hardwood floors, and finely preserved craftsmanship throughout. The home has undergone a thoughtful, major renovation that honors its historic character while seamlessly incorporating modern comforts and functionality. Privately sited on an impressive 7.32 acres, the grounds offer serenity, space, and a sense of timeless estate living.

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$4,495,000
814
6bedrooms
7bathrooms

By Annonceur International

30

House Milton (United States)

Set on a private lane within a five-home enclave, this 10,000+ SF estate is bordered by 7,000 acres of protected land in the Blue Hills Reservation, offering a level of privacy rarely found this close to Boston. Accessed by a stone bridge, the home unfolds across 20 thoughtfully designed rooms with 6 bedrooms and 6 bathrooms. A grand foyer leads to vaulted ceilings, a paneled library with fireplace, multiple living and recreation spaces, a home gym, and a dedicated home theater. The kitchen, equipped with premium appliances, opens seamlessly to a large family room anchored by a floor-to-ceiling stone fireplace. The primary suite features a five-piece bath, steam shower, and multiple walk-in closets. Set on 4+ acres, the grounds include a stone terrace with outdoor kitchen, fireplace, jacuzzi, and mature landscaping. A heated four-car garage, dual driveways, and circular motor court complete the offering. Not just a Milton home; an estate with a Milton address.

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$5,995,000
978
6bedrooms
4bathrooms

By Annonceur International

14

House with garden Milton (United States)

Milton—Rare New 2-Family find! This fully renovated 2016 duplex offers 5 rooms, 3 bedrooms, and 2.5 baths. The first floor features a spacious kitchen with stainless steel appliances, granite countertops, an open living/dining area, and first-floor laundry. The second floor boasts 2 bedrooms and 2 full baths, while the third-floor bedroom includes a walk-in closet. A generous yard is ideal for summer gatherings, and the unfinished basement offers storage or expansion potential. Convenient highway access, near Milton Academy and public schools. Located in the heart of Milton, close to The Blue Hills’ scenic trails, Cunningham Park’s ballfields and pool, and East Milton Square’s dining and shopping at Abby Park, Novara, The Fruit Center, The Cue & Nutshell.

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$1,575,000
3,216
6bedrooms
4bathrooms
land 9,461

By Annonceur International

406 listings near Milton

Nearby
25

House Boston (United States)

Come visit us this weekend at The Residences at Kinsale Lane, located on Fairmount Hill, Hyde Park on the Milton line. All the benefits and advantages of city living and services in a dynamic newly constructed cul-de-sac, offering privacy and eight new custom luxury homes. These new homes feature cutting edge open floor plan design with attached two car garages, 3/4 bedrooms, stunningly appointed bathrooms and chef's kitchens. Cozy up to the fireplace, or outside on the private deck and wonderful backyard. No detail has been overlooked and you'll dream of future expansion possibilities with unfinished vaulted 3rd floor spaces and ample additional unfinished space in the basements. Come check out the Residences at Kinsale Lane and see all that we have to offer. WE HAVE 5 OF THE 8 HOMES UNDER AGREEMENT. COME CHECK OUT THE 3 REMAINING PLANS FOR 6, 7, AND 8 !!!

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$1,375,000
190
3bedrooms
2bathrooms

By Annonceur International

Nearby
Contract pending
36

House with garden Boston (United States)

A rare opportunity for single-home privacy with space for future customization in Hyde Park’s commuter friendly Fairmount neighborhood. Set on a prominent corner lot, this thoughtfully designed property blends timeless character with flexible living. Original details like custom wood railings, handcrafted trim, antique fixtures, and a split-level tiled entry add warmth and personality throughout. A sun-filled bay window anchors the living room, flowing seamlessly into the dining area and kitchen for everyday functionality. The window-lined all-season patio offers a versatile extension of living space. This home ideal for makers, collectors, or doers ready to utilize the abundant storage & flex spaces throughout. The lower level presents compelling potential for an ADU, guest suite, or multigenerational living, complete with direct entry, full bath, and kitchenette. This home is a distinctive offering for buyers seeking character, expansion, income potential, and long-term value.

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$784,000
4bedrooms
2bathrooms
land 607

By Gibson Sotheby's International Realty

Nearby
Contract pending
39

House with garden Boston (United States)

Seize this rare opportunity to make your Boston homeownership dream a reality with a thoughtfully updated single family offering true move-in ease in Hyde Park, “A Small Town in the City.” Set on a tree lined street, the home features sun-drenched interiors and gleaming wood floors that set the tone, while modern kitchen blends style and function with upgraded cabinetry, refined counters and stainless steel appliances. Fresh interior paint and an intuitive layout create a main level that feels both elevated and welcoming. The LL expands the living experience with a spacious family room, full bath, laundry and exceptional storage, ideal for media, guests or flexible living. Outside, a deep, level backyard becomes a natural extension of the home, perfect for summer entertaining, quiet mornings on the deck or future garden design. Three well-scaled bedrooms, mudroom, detached garage complete the offering. with easy access to downtown Boston and seamless reach to the South Shore and Cape.

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$650,000
3bedrooms
2bathrooms
land 526

By Gibson Sotheby's International Realty

Nearby
Contract pending
15

Property Boston (United States)

Own your slice of the American dream in this beautifully renovated Colonial, ideally located in one of Hyde Park’s most sought-after commuter locations—just steps to public transportation and Hyde Park Center. This move-in-ready home offers the perfect blend of convenience, comfort, and style. The first floor features an open-concept layout with hardwood floors throughout, creating a seamless flow between the living, dining, and kitchen spaces. The updated kitchen shines with stainless steel appliances, granite countertops, and maple cabinetry—perfect for everyday living and entertaining. Upstairs, you’ll find three well-proportioned bedrooms, all with hardwood flooring. Detached one-car garage and off-street parking. A rare opportunity to enjoy city living with space, charm, and unmatched accessibility. Showings start at open house Friday 3:30-5.

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$575,000
3bedrooms
2bathrooms
land 283

By Gibson Sotheby's International Realty

Nearby
23

House Boston (United States)

***OFFERS DUE MONDAY 10/28 @ 7PM ***Rare opportunity to own a turnkey multifamily in the RED HOT Dorchester market. Currently grossing $9,650/month & $116,280 annually. This massive 3 Family consisted of (2) 3 Bed units and (1) 4 Bed unit. Unit 1 will be delivered vacant. All 3 units come with Lead Compliance Certificates. Large finished basement with the potential for a bonus unit. Separate utilities (except water). Conveniently located near Fields Corner T Station, Target, Parks and other local amenities. Perfect property for both investors or owner occupants.

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$1,250,000
378
10bedrooms
3bathrooms
land 323

By Annonceur International

Nearby
Contract pending
33

Property Boston (United States)

A four-bedroom, two and a half -bath Roslindale single-family with great bones and a backyard that's been loved into something special. The covered front porch opens to a living room anchored by a pellet stove, then circles through to a dining room with original wood-panel wainscoting and into a semi-open eat-in kitchen. The kitchen sink looks straight onto the yard, as does the dining room. Afternoon light fills the upper-level front bedrooms, and the backyard enjoys sun throughout the day, including strong southern exposure. Out back, a fenced garden framed by peach and elderberry trees and raspberry brambles. Hydrangeas line the side of the house, peonies the front walk. Clean, dry basement with French drain and sump pump, plus real upside for future finishing. Tandem driveway pkg for two; on-street easy. Fresh exterior paint, new roof in 2025, driveway repaved 2024. Less than a mile to Roslindale Village, the farmers market, and the commuter rail. Conley Elementary a quarter mile away.

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$689,000
4bedrooms
3bathrooms
land 526

By Gibson Sotheby's International Realty

Nearby
Contract pending
11

House Roslindale (United States)

A brick-faced 1935 Ranch with vaulted ceilings, a fireplace, and stained glass details—sitting on a level 4,650 square foot lot on a quiet residential street at the JP/Roslindale line. The bones have character; the condition calls for vision. This is a gut renovation or new construction opportunity priced accordingly, in a location that continues to attract serious buyer interest on both sides of the zip line. 1F-4000 zoning. Two beds, one bath, 684 square feet of living area with a total footprint of 1,685 square feet. The lot is level and straightforward for an addition or a ground-up build. The brick facade, stained glass, and foundation may inform what comes next—or simply mark where it started. Sold as-is, where-is. Vacant and easy to show. Sellers reviewing offers April 27th; please make offers good through 5PM April 29th.

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$399,999
2bedrooms
1bathroom
land 445

By Gibson Sotheby's International Realty

Nearby
Contract pending
18

House with garden Braintree (United States)

Fall in love with this charming Craftsman style home where every detail has been carefully considered to create a cozy and inviting atmosphere. The welcoming front porch sets the tone for relaxed living. Inside you’ll find stylish touches and comfortable spaces throughout. Features include several important home improvements, lots of storage in the basement and a garage. The thoughtfully designed kitchen has abundant storage, and a sunny dining area overlooking the adorable backyard. Located on picture-perfect West Street, named one of Boston Magazine’s most desirable streets. Close proximity to the Red Line, major highways, shops and restaurants make this the perfect spot to call home.

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$778,000
3bedrooms
2bathrooms
land 486

By Gibson Sotheby's International Realty

Nearby
Contract pending
34

Property with garden Boston (United States)

Of all the Jamaica Plain neighborhoods, Woodbourne is the one people grow into. This 1922 stucco Colonial on a corner knoll is one of its bespoke originals, shaped over a century by four families. The front door opens into the living room: beamed ceiling, original mantel, working wood fireplace, and French doors bookending the hearth into a heated sunroom wrapped in conifers. To the right, a wainscoted, south-facing dining room with a solid wood deco door at its far end opening to a first-floor office suite — private entrance, full bath, originally the home's physician owner's consulting room. Renovated kitchen: Candlelight cabinetry, quartz, butcher-block peninsula, pro range vented outside. Three bedrooms up; primary with a second wood fireplace and renovated bath. Third floor: two flex rooms, skylight, preserved antique bath. Mostly original windows with storm sashes. Parking for two. A block from the 32 bus to Forest Hills; bordered by Forest Hills Cemetery's Olmsted-era landscape.

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$1,225,000
4bedrooms
3bathrooms
land 850

By Gibson Sotheby's International Realty

Nearby
Contract pending
39

Property with garden Boston (United States)

A delectable single family with fenced backyard, tucked on a side street near Roslindale Village. With three levels, this four-bed, one and a half-bath home offers extra potential in the partially finished top floor. Past the porch swing and foyer, a classic living room with bay windows greets you. Pocket doors open into a strikingly bright dining room with four windows, two facing the backyard’s majestic linden tree. The kitchen offers a 2024 induction range, ample cabinetry, and access to the patio and yard with raised beds and perennials. In the foyer, a half bathroom. The second level provides two good-sized bedrooms; a third smaller bedroom; and a bonus room that leads to the top floor. The top level offers a fourth bedroom and an adjacent unfinished attic space that hints at expansion potential. Enjoy four-zone cooling and a large basement with high ceilings. Bask in village life: just blocks to the farmer’s market in Adams Park, beloved shops in the square, and commuter train to South Station.

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$875,000
4bedrooms
2bathrooms
land 283

By Gibson Sotheby's International Realty

Nearby
30

House Braintree (United States)

One of the the prettiest houses on one of Braintree's prettiest streets! This classic brick colonial will capture your heart! Gorgeous custom kitchen w/large island & Wolf/Sub zero appliances is the heart of the home OPEN to the stunning family room w/coffered ceiling, FP and custom built-ins. Charming butlers pantry w/nostalgic swing door connects the gracious dining room to the kitchen. A beautiful foyer welcomes guests upon entry, flanked by a sunny fireplaced living room and private Office/Library tucked away from all the hustle and bustle. Upstairs there are 4 bedrooms inc. a lovely primary suite w/priv. bath and opportunity for expansion over the library below. The lower level is finished offering a gym and kid play room space. Enjoy the MAGICAL and private back yard w/mature trees, blue stone patio, stone FP and plenty of lawn for play. Enchanting screen porch and brick 2 c. garage w/arched doors. Sidewalks to Thayer academy & downtown shops/restaurants. JUST 10 MILES to BOSTON!

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$1,995,000
377
4bedrooms
2bathrooms

By Annonceur International

Nearby
Contract pending
37

Property Quincy (United States)

Ideally located between the Merrymount and Adams Shore neighborhoods, this recently expanded home offers a surprising amount of living space spanning across three levels, plus 672 sq ft of additional finished space in the lower level. Gleaming hardwood floors with dark wood inlay have just been refinished throughout, adding warmth and character on every level. The main level features a spacious kitchen, dining room, and living room with a wood burning fireplace, along with a first floor bedroom and adjacent full bath—ideal for guests or flexible living needs. The second floor offers three oversized bedrooms and another full bath. Capping this off, the top floor provides a versatile open flex space with direct access to a large walk out deck with views of Quincy Bay. The partially finished basement adds even more usable space with a living room, gas fireplace, and half bath. A detached two car garage and updated systems throughout make this home truly move in ready.

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$895,000
4bedrooms
4bathrooms
land 526

By Gibson Sotheby's International Realty

Nearby
Contract pending
40

Property with garden Boston (United States)

The yellow door calls your attention from the street. The layout inside keeps it. A classic Roslindale Colonial with a first floor that moves in a loop - kitchen, living room, and dining room each with a distinct purpose but still connected, a bar counter keeping the kitchen part of the conversation, and a south-facing sunroom that earns its name. The 2nd floor offers two well-proportioned bedrooms, a dedicated laundry room, and a captured desk nook at the top of the stairs. The entire 3rd floor is the primary suite. Outside: a genuinely spacious fenced backyard with patio, deck, shed, and room for long dinners, garden projects, and dogs tearing laps. Owned solar (Dec. 2023) cuts electricity to near $0 most months; EV charger in the two-car tandem driveway. two-zone gas forced hot air and central AC (~2014), Navien tankless hot water (2024), 200A service, the to-do list here is short. On-street pkg easy. Beech Street puts you close to the best of Roslindale without being in the middle of it.

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$949,000
3bedrooms
3bathrooms
land 567

By Gibson Sotheby's International Realty

Nearby
Contract pending
16
Video

Property with garden Boston (United States)

Tucked along a private road at the edge of the Arboretum, this beautifully rebuilt 2009 single family offers a rare sense of calm within a connected urban setting. Rebuilt by master builder Chris DeSisto of Maplehurst Builders, the home reflects the sensibility of someone who understood not only how to build, but how to live. There is a feeling that is hard to name, something between a cabin in the woods and a well crafted boat, where every inch is thoughtfully considered and deeply comfortable. Warm natural wood, soaring ceilings, and abundant light define the main living space, anchored by a fireplace and an open, well designed kitchen with custom cabinetry. A first floor bedroom and full bath offer flexibility, with two bedrooms above. The finished lower level adds living space, a full bath, and room for work or recreation. Set on a 4,185 square feet lot with a small yard, ample parking, and a Tesla charger, this 2,244 square feet home lives with ease, shaped by both nature and neighborhood.

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$1,450,000
3bedrooms
3bathrooms
land 405

By Gibson Sotheby's International Realty

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