89

Wellesley Hills, MA Homes for Sale with Acreage

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  • /42

    $34,000,000

    • 6 Beds
    • 8 Baths
    • 12,714 Sq Ft

    4 Willow Rd, Weston, MA 02493

    Step into a world of timeless elegance in this iconic English Revival Tudor. Prominently set high on a ridge abutting a tranquil pond and the lands surrounding the Weston Golf Club. The gated entry and winding approach reveal the commanding terraced property comprising over 6 secluded acres. The 1928 estate was originally designed by architect Eric Kibbon. A balance between modern comfort, beauty

    Mizner+ Montero Gibson Sotheby's International Realty

    4 Willow Rd, Weston, MA 02493
  • /25

    $9,950,000

    • 5 Beds
    • 9 Baths
    • 8,633 Sq Ft

    76 Robin Rd, Weston, MA 02493

    Magnificently sited on over two acres with breathtaking views of Weston Golf Club, this young Shingle and Stone estate blends timeless architecture with modern sophistication. Designed by award-winning architect Patrick Ahearn, this custom beauty offers over 8,600 square feet of freshly updated, Architectural Digest–worthy interiors filled with natural light. Highlights include a dazzling chef's

    The Shulkin Wilk Group Compass

    76 Robin Rd, Weston, MA 02493
  • /28

    $849,000

    • 2 Beds
    • 2 Baths
    • 1,285 Sq Ft

    250 Hammond Pond Pkwy Unit 1111s, Chestnut Hill, MA 02467

    Chestnut Hill! Feel the quiet and calm elegance of this sun-filled 2 bedroom 2 bath condominium at the Chestnut Hill Towers. Watch the changing New England seasons above the colorful treetops from the 11th floor. An abundance of natural light and gorgeous sunsets off in the west make this open floor plan home perfect for entertaining. The spacious primary suite includes ensuite bathroom and 2

    Richard C. Dore Hammond Residential Real Estate

    250 Hammond Pond Pkwy Unit 1111s, Chestnut Hill, MA 02467
  • /36

    $2,450,000

    • 5 Beds
    • 8 Baths
    • 6,800 Sq Ft

    9 Buttercup Ln, Dover, MA 02030

    Tucked away on a private road beside the natural beauty of Elm Bank Reservation, this exceptional Cape-style home offers thoughtfully designed living space with timeless charm and modern flexibility. The residence features five generously sized bedrooms, each with a private bath, ideal for multigenerational living or hosting long-term guests. A private au pair or in-law suite includes its own

    John Hughes Dover Country Properties Inc.

    9 Buttercup Ln, Dover, MA 02030
  • /37

    $940,000

    • 2 Beds
    • 2 Baths
    • 1,433 Sq Ft

    250 Hammond Pond Pkwy Unit 1503N, Chestnut Hill, MA 02467

    Sun-flooded 15th floor SW-facing showpiece! The largest 2BR/2BA floorplan at The Towers of Chestnut Hill has been transformed into a gorgeous turn-key residence. Beautiful HW floors, custom millwork & recessed lighting set the tone. Chef's kitchen boasts high-end custom cabinetry, counter seating & large dinette opening to a private balcony via glass sliders. The ultra-bright open LR/DR is made

    Mac Chinsomboon Coldwell Banker Realty - Boston

    250 Hammond Pond Pkwy Unit 1503N, Chestnut Hill, MA 02467
  • /23

    $4,750,000

    • 3 Beds
    • 4.5 Baths
    • 4,200 Sq Ft

    136 Dudley Rd, Newton Center, MA 02459

    Rarely available 3.25-acre property on Newton's South Side offers an exceptional development opportunity in an estate property area. The site is located on picturesque Dudley Road, surrounded by mature trees and expensive homes. There is currently a 4,200sf antique barn on the property that was converted to a residence 50 years ago. This residence has 4 bedrooms, 3 bathrooms and a 2-car garage.

    Ezra Stillman Hammond Residential Real Estate

    136 Dudley Rd, Newton Center, MA 02459
  • /28

    $4,800,000

    • 5 Beds
    • 6.5 Baths
    • 12,144 Sq Ft

    451 Wellesley St, Weston, MA 02493

    Set on 5.6 private acres on Weston’s highly desirable south side, this impressive estate offers exceptional privacy and timeless appeal. Tucked at the end of a long, winding driveway, this Federal Colonial blends classic architecture with comfortable living, featuring sun-filled interiors, a dramatic two-story family room with fireplace, a bright sunroom, and a stylish home office. The flexible

    Yang Liu Weston Realty LLC

    451 Wellesley St, Weston, MA 02493
  • /42

    $7,598,000

    • 6 Beds
    • 10 Baths
    • 9,000 Sq Ft

    56 Cart Path Rd, Weston, MA 02493

    Exquisite cape colonial estate in Weston’s golf club area. Perfect location on 2.85 acres in Weston's top neighborhood. Two floor grand foyer opens to the coffered great room, drenched in light from the floor to ceiling windows and the patio doors, which open out to the massive deck overlooking the large, flat, private back yard, while the grand fireplace and custom millwork impress. Large chef’s

    Rose Hall Blue Ocean Realty, LLC

    56 Cart Path Rd, Weston, MA 02493
  • /31

    $1,450,000

    • 4 Beds
    • 3 Baths
    • 3,004 Sq Ft

    75 High Rock St, Needham, MA 02492

    Circa 1843, this timeless 4 bedroom, 3 bath home blends historic character with gracious living, beautifully set on a picturesque 1-acre lot in a highly desirable location. Rich in period detail, the home features beautiful wide plank floors, two fireplaces, and thoughtfully designed living spaces filled with warmth and charm. The elegant dining room with classic built-ins is perfect for both

    Maryruth Perras William Raveis R.E. & Home Services

    75 High Rock St, Needham, MA 02492
  • /23

    $825,000

    • 2 Beds
    • 2 Baths
    • 1,285 Sq Ft

    250 Hammond Pond Pkwy Unit 705S, Chestnut Hill, MA 02467

    Welcome to luxury living at The Towers! This meticulously updated 2-bedroom, 2-bath residence blends luxury with functionality in one of the area's most prestigious full-service communities. Includes 2 deeded parking spaces. Enjoy resort style amenities: 24-hour concierge, indoor pool, fitness center, tennis/pickleball courts, club lounge, and game room. Benefit from additional storage and

    Richard C. Dore Hammond Residential Real Estate

    250 Hammond Pond Pkwy Unit 705S, Chestnut Hill, MA 02467
  • /25

    $2,195,500

    • 5 Beds
    • 3.5 Baths
    • 5,778 Sq Ft

    28 Centre St, Dover, MA 02030

    Brilliant contemporary colonial on Dover’s North side is a not-to be-missed opportunity for buyers seeking privacy, generous and versatile liv spaces and exceptional value. Architect Elise Stone designed dramatic and seamless 2 story extension taking the home from “nice” to “wow!” Enormous foyer w/HW flrs is elegant zone for welcoming guests. Step-down liv rm is where holiday memories are made.

    The Bauman Group Gibson Sotheby's International Realty

    28 Centre St, Dover, MA 02030
  • /39

    $1,749,000

    • 3 Beds
    • 4.5 Baths
    • 3,163 Sq Ft

    277 Nahanton St, Newton Center, MA 02459

    Stunning, fully renovated residence in the highly sought-after Ledgebrook community, offering modern design and exceptional comfort. This elegant home features high-end kitchen with stainless steel appliances and an open floor plan with dining area and a dramatic cathedral-ceiling living room with gas fireplace opening to a private backyard. The first-floor primary suite offers comfort and

    Osnat Levy eXp Realty

    277 Nahanton St, Newton Center, MA 02459
  • /42

    $14,850,000

    • 7 Beds
    • 12 Baths
    • 18,725 Sq Ft

    67 Byron Rd, Weston, MA 02493

    Timeless elegance meets modern luxury in this extraordinary Weston estate, situated on 5.3 stunning acres just minutes from Boston. Built by a renowned local builder and reimagined with Leslie Fine Interiors, this home blends superior craftsmanship, global influences and design. Bright, inviting spaces include a newly renovated kitchen, luxurious primary suite, soaring ceilings, and dramatic

    Maggie Gold Seelig MGS Group Real Estate LTD

    67 Byron Rd, Weston, MA 02493
  • /31

    $3,349,000

    • 4 Beds
    • 3.5 Baths
    • 4,246 Sq Ft

    85 Strawberry Hill St, Dover, MA 02030

    Tucked inside the pastoral landscape of coveted Strawberry Hill, this exceptional Dover offering blends tranquility with timeless New England charm. The property's picturesque two-acre lot is framed by by classic stone walls, sweeping meadow views, and abuts conservation land steps from the Hale Reservation trailhead and Noanet woods. While peacefully situated, the home is minutes to Needham

    Meghan Sutherland MGS Group Real Estate LTD - Wellesley

    85 Strawberry Hill St, Dover, MA 02030
  • /28

    $1,090,000

    • 3 Beds
    • 2.5 Baths
    • 2,746 Sq Ft

    265 Bacon St, Natick, MA 01760

    This property is move-in ready and perfectly situated for commuters, families, or those seeking a lifestyle upgrade. This sun-drenched home features an expansive open floor plan designed for seamless entertaining. The chef-inspired white kitchen boasts a large center island and flows into a bright dining area with access to an enlarged private patio and backyard. Relax in the family room,

    Jason Zhang Compass

    265 Bacon St, Natick, MA 01760
  • /12

    $4,000,000

    • Land
    • 1.31 Acres
    • $3,053,435 per Acre

    74 Rumford Ave, Waltham, MA 02453

    57,255 sf parcel.Walking distance to vibrant Moody Street with retail shops and restaurants • Quiet setting with frontage on Cram’s Cove, an estuary of the Charles River • “Commercial” zone with “Riverfront Overlay” allows a variety of uses, including multifamily, with generous height and FAR allowances

    Ben Silva Acorn Property Management LLC

    74 Rumford Ave, Waltham, MA 02453
  • /33

    $665,000

    • 1 Bed
    • 1.5 Baths
    • 1,060 Sq Ft

    280 Boylston St Unit 308, Chestnut Hill, MA 02467

    Fully gut-renovated 1BR/1.5BA (in 2016) at prestigious Imperial Towers, Chestnut Hill. Reimagined floor to ceiling, no expense spared. Sun-filled open living area with signature oval tray ceiling, engineered hardwood floors, and insulated windows and balcony door installed in 2019. The showstopping Norwegian handcrafted kitchen offers lacquered cabinetry, waterfall stone island, integrated Miele

    Alexsandr Groza Zoom Realty, Inc.

    280 Boylston St Unit 308, Chestnut Hill, MA 02467
  • /42

    $6,695,000

    • 6 Beds
    • 8 Baths
    • 8,093 Sq Ft

    222 Grove St, Wellesley, MA 02482

    Discover exceptional elegance & privacy in Wellesley’s coveted Dana Hall neighborhood. Set on over an acre in one of the town’s most sought-after locations it offers the perfect balance of privacy & convenience. Designed by a renowned local architect, this stunning new home blends sophisticated design with modern comfort, creating a serene retreat moments from town. The main floor boasts an open,

    Steve & Nicole Connolly Group Coldwell Banker Realty - Wellesley

    222 Grove St, Wellesley, MA 02482
  • /39

    $31,500,000

    • 6 Beds
    • 12 Baths
    • 21,000 Sq Ft

    180 Ash St, Weston, MA 02493

    This extraordinary estate is set on one of Weston’s most prestigious enclaves and blends grand architecture with modern luxury, impeccable craftsmanship and state of the art systems. High ceilings, intricate moldings, and sun-drenched rooms create an atmosphere of timeless elegance. The main level is designed for both grand entertaining and comfortable living, featuring an expansive chef's

    Maggie Gold Seelig MGS Group Real Estate LTD

    180 Ash St, Weston, MA 02493
  • /40

    $9,888,000

    • 6 Beds
    • 11 Baths
    • 14,620 Sq Ft

    3 Idlewile Ln, Weston, MA 02493

    Set behind gates on more than 8 acres in Weston’s prestigious south side, this extraordinary estate abuts protected conservation land, offering rare privacy and natural seclusion. Spanning over 14,000 square feet, the residence is distinguished by soaring ceilings, finely detailed custom millwork, Venetian plaster, and imported stone—crafted to exacting standards throughout. Gracious yet

    Collin Sullivan William Raveis R.E. & Home Services

    3 Idlewile Ln, Weston, MA 02493
  • /40

    $5,695,000

    • 6 Beds
    • 8 Baths
    • 9,848 Sq Ft

    182 Winding River Rd, Wellesley, MA 02482

    Custom home on the Charles River. Incredible views of the river and conservation land beyond plus a dock for kayaks, paddleboards & small electric boats! 2006 new construction w/over 9000 sq ft of living space on 1.73 acres. Walk into dramatic great room w/ 2 story windows plus one of four fireplaces & custom window seat perfect for entertaining. NEWLY renovated white kitchen w/ center island,

    Melissa Dailey Coldwell Banker Realty - Wellesley

    182 Winding River Rd, Wellesley, MA 02482
  • /39

    $7,590,000

    • 6 Beds
    • 7.5 Baths
    • 8,421 Sq Ft

    286 Country Dr, Weston, MA 02493

    This custom-built modern estate sits prominently on a 1.42-acre corner lot and pairs striking architectural design with uncompromising craftsmanship across ~8,421 SF and 3 curated levels. A dramatic entry welcomes you into a soaring foyer anchored by a sculptural staircase and statement lighting, setting the tone for the home’s sophisticated aesthetic. Expansive floor-to-ceiling glass floods each

    George Sarkis Douglas Elliman Real Estate - The Sarkis Team

    286 Country Dr, Weston, MA 02493
  • /42

    $1,890,000

    • 3 Beds
    • 6 Baths
    • 3,345 Sq Ft

    40 Hobbs Brook Rd, Weston, MA 02493

    Introducing a sophisticated contemporary home, perched on a hill with exceptional privacy, serene surroundings and a true connection to nature. The versatile and open design integrates the inside with the zen-like landscape for an elevated entertainment experience. The well-equipped kitchen and large dining area are complemented by multiple sitting areas. Three well-appointed bedrooms, including

    Mizner+ Montero Gibson Sotheby's International Realty

    40 Hobbs Brook Rd, Weston, MA 02493
  • /28

    $639,000

    • 1 Bed
    • 1.5 Baths
    • 899 Sq Ft

    250 Hammond Pond Pkwy Unit 604N, Chestnut Hill, MA 02467

    Towers of Chestnut Hill, residence 604N, no expense has been spared to create this sophisticated home. This magazine worthy unit is renovated to the highest standard with quality craftmanship throughout. Top of line finishes and thoughtfully designed choices created this perfect condominium. This home showcases tremendous space, light and well-proportioned rooms and allows entertaining on an

    Richard C. Dore Hammond Residential Real Estate

    250 Hammond Pond Pkwy Unit 604N, Chestnut Hill, MA 02467
  • /31

    $7,295,000

    • 6 Beds
    • 7.5 Baths
    • 8,773 Sq Ft

    5 Deer Path Ln, Weston, MA 02493

    This newly-constructed, Contemporary offers the pinnacle of luxury living on Weston’s coveted Southside. The dramatic, 2-story foyer flows seamlessly into both formal & informal spaces. The dining/living room is optimal for family gatherings & entertaining, and the custom kitchen w/an exceptional quartz island, high-end appliances & wet bar adjoins a generous eat-in area & fireplaced family room

    Beyond Boston Properties Group Compass

    5 Deer Path Ln, Weston, MA 02493
  • /36

    $1,099,000

    • 4 Beds
    • 2.5 Baths
    • 2,393 Sq Ft

    169 Woodland St, Natick, MA 01760

    Rare opportunity to acquire an updated home with all the amenities on one level in Beautiful South Natick. A professionally landscaped property with an integrated irrigation system. Stone patio, fenced in back yard with dog park area. This spacious home features a vaulted entertainment room, fire-placed Livingroom with a wood stove, and a reading room. Open chefs' kitchen with pantry. Laundry

    Mark Woodbury Cameron Real Estate Group

    169 Woodland St, Natick, MA 01760
  • /24

    $489,000

    • 1 Bed
    • 1 Bath
    • 1,060 Sq Ft

    280 Boylston St Unit 804, Chestnut Hill, MA 02467

    Come bring your personal touch to this sun-filled 1-bedroom, 1-bath unit at Imperial Towers in Chestnut Hill. Situated on the 8th floor this condo has a terrific view and great bones! Located in the heart of Chestnut Hill, this Concierge building features a heated seasonal pool, new fitness center, clubroom, beautiful lobby, library, EV Charging Station, extra storage and on-site management.

    Betsy Kessler Rutledge Properties

    280 Boylston St Unit 804, Chestnut Hill, MA 02467
  • /32

    $2,585,000

    • 4 Beds
    • 5.5 Baths
    • 5,216 Sq Ft

    7 Circle Dr, Dover, MA 02030

    Built in 2025, this remarkable 4BR 5.5BA home is set off the road in a quiet cul de sac near the Wellesley/ Needham line. The open concept first floor boasts an eat in gourmet kitchen with beautiful cabinetry, large island, quartz countertops and Thermador appliances; an open family room w/sliders to the yard, fireplaced living room, dining area and powder room. Upstairs, a beautiful primary

    Mary Crane Berkshire Hathaway HomeServices Commonwealth Real Estate

    7 Circle Dr, Dover, MA 02030
  • /39

    $4,585,000

    • 6 Beds
    • 8 Baths
    • 9,825 Sq Ft

    68 Locust Ln, Needham, MA 02492

    Your chance to make this stunning new construction yours! Located on a private cul-de-sac set on the Needham- Wellesley border. The grand two-story entrance features an open-concept layout with a living room, a formal dining room, a home office with a fireplace, a guest en suite, and a chef's kitchen with two islands, a walk-in pantry, and a breakfast/dining area overlooking a beautiful backyard.

    Alex Kuzakovsky Luna Luxury Realty

    68 Locust Ln, Needham, MA 02492
  • /40

    $5,495,000

    • 5 Beds
    • 8 Baths
    • 9,200 Sq Ft

    300 Glen Rd, Weston, MA 02493

    Stunning shingle style 5 bedroom home on Weston's South side. Completely renovated kitchen & baths giving this home the ideal layout, style & convenient location. Light filled kitchen w/ large picture window overlooks the 2.68 acres plus abutting conservation land w/ trails. Huge center island & high end appliances w/ working fireplace in kitchen. Adjacent family room w/ coffered ceilings,

    Melissa Dailey Coldwell Banker Realty - Wellesley

    300 Glen Rd, Weston, MA 02493
  • /34

    $2,199,000

    • 4 Beds
    • 3.5 Baths
    • 4,195 Sq Ft

    60 Claybrook Rd, Dover, MA 02030

    Magnificent custom home in one of Dover’s most desirable neighborhoods, minutes to top schools, shopping and local amenities with premium craftsmanship and high-end finishes. Offering 4195 sq ft of living space, the flexible layout is ideal for everyday living and entertaining. The first-floor features elegant living and dining rooms, a warm family room with fireplace, and private home office or

    Denise Mosher Coldwell Banker Realty - Weston

    60 Claybrook Rd, Dover, MA 02030
  • /18

    $859,000

    • 2 Beds
    • 2 Baths
    • 1,735 Sq Ft

    210 Nahanton St Unit 522, Newton Center, MA 02459

    Beautiful penthouse living in Newton! This spacious 1,735 sqft residence offers spectacular, unobstructed views from the private balconies and every room. Situated in a professionally managed luxury building, this home features newly replaced windows and sliding glass doors that enhance natural light and indoor-outdoor flow. The interior boasts new hardwood floors throughout the living room and

    Nan Liang Longwood Homes Real Estate, LLC

    210 Nahanton St Unit 522, Newton Center, MA 02459
  • /42

    $3,250,000

    • 5 Beds
    • 6 Baths
    • 6,952 Sq Ft

    5 Pegan Ln, Natick, MA 01760

    Welcome to your private retreat in beautiful South Natick. Sited on 2.24 acres of impeccably manicured grounds, this move-in-ready home offers a rare blend of open, sun-filled living spaces and resort-style outdoor amenities. Oversized windows bathe the home in natural light, highlighting the spacious layout that’s perfect for both everyday living and entertaining. The first-floor primary suite

    Bill Paulson Keller Williams Realty

    5 Pegan Ln, Natick, MA 01760
  • /27

    $1,675,000

    • 4 Beds
    • 3 Baths
    • 2,840 Sq Ft

    37 School St, Weston, MA 02493

    Beautifully sited on over 2 private acres, this 8-room, 4-bed, 3-bath home offers comfort, charm, and room to grow. The spacious living room features a fireplace and hardwood floors, flowing into a formal dining room with two classic corner cabinets and a sun-filled kitchen with white cabinetry, stainless appliances, and center island. Two generous bedrooms and a full bath complete the first

    Denise Mosher Coldwell Banker Realty - Weston

    37 School St, Weston, MA 02493
  • /38

    $4,795,000

    • 6 Beds
    • 7 Baths
    • 7,000 Sq Ft

    21 Westerly Rd, Weston, MA 02493

    1.38 acres of flat land in coveted Weston Estates! Stunning shingle and stone 6 bedroom Colonial. Extraordinary outdoor space featuring a pavilion with kitchen plus stone fireplace perfect for outdoor living and entertaining. Large kitchen with oversized island and seating area opens to double storeyed family room along with beautiful floor to ceiling stone fireplace, wet bar and incredible

    Melissa Dailey Coldwell Banker Realty - Wellesley

    21 Westerly Rd, Weston, MA 02493
  • /27

    $819,000

    • 2 Beds
    • 2 Baths
    • 1,285 Sq Ft

    250 Hammond Pond Pkwy Unit 609N, Chestnut Hill, MA 02467

    An opportunity to live behind the gates. The Towers of Chestnut Hill, Hammond Pond Parkway's most prominent building, embodies the very essence of luxury Chestnut Hill living. Fully amenitized living, including heated indoor swimming pool, newly installed fitness center, brand new pickleball court and 24-hour doorman underscores it all. On rare occasions, a two-bedroom, two full bath unit with

    Richard C. Dore Hammond Residential Real Estate

    250 Hammond Pond Pkwy Unit 609N, Chestnut Hill, MA 02467
  • /31

    $1,195,000

    • 3 Beds
    • 2 Baths
    • 1,627 Sq Ft

    250 Hammond Pond Pkwy Unit 1507N, Chestnut Hill, MA 02467

    A rare opportunity to own a three-bedroom home in one of Chestnut Hill’s most prominent luxury buildings on Hammond Pond Parkway. This 15th-floor corner residence offers breathtaking southwest views, beautiful sunsets, nearly 1,700 square feet of living space, and a layout that lives even larger. Three generously sized bedrooms, two full baths, and thoughtful details throughout create an

    Richard C. Dore Hammond Residential Real Estate

    250 Hammond Pond Pkwy Unit 1507N, Chestnut Hill, MA 02467
  • /18

    $7,200,000

    • Land
    • 3 Acres
    • $2,400,000 per Acre

    21 Eliot St, Natick, MA 01760

    Presenting 21 Eliot Street, 3 acres of beautifully maintained and natural grounds in Natick, Massachusetts. Currently improved by four well-preserved buildings featuring a mix of office and retail spaces, the property presents an unparalleled opportunity for commercial and residential redevelopment. The underlying zoning of 70% RSC and 30% CII allows for a multitude of development options. The

    Chris Sower Cushman & Wakefield

    21 Eliot St, Natick, MA 01760
  • /2

    $1

    • Land
    • 1.77 Acres
    • $1 per Acre

    0 Wellesley St, Weston, MA 02493

    An exceptional development opportunity on coveted Wellesley Street in Weston. Set on a generous, private lot, this rare offering invites builders, developers, and end-users alike to bring their vision to life in one of the town’s most desirable locations. The property provides an ideal canvas for a custom residence—whether a modern masterpiece or a timeless New England estate—surrounded by

    Maggie Gold Seelig MGS Group Real Estate LTD

    0 Wellesley St, Weston, MA 02493
  • /20

    $499,000

    • 2 Beds
    • 2 Baths
    • 897 Sq Ft

    655 Saw Mill Brook Pkwy Unit 9, Newton Center, MA 02459

    Set in a desirable and convenient setting, this beautifully updated 2-bedroom, 2-bath residence offers easy living in a peaceful residential neighborhood. The sun-filled open floor plan is ideal for everyday living and entertaining, featuring an updated kitchen with modern cabinetry. The spacious living room opens to a private balcony overlooking serene gardens. The primary bedroom features an

    The Kennedy Lynch Team Hammond Residential Real Estate

    655 Saw Mill Brook Pkwy Unit 9, Newton Center, MA 02459

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