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7566 W Harbor Highway, Glen Arbor
$3,795,000
4 Beds ⋅ 3 Baths ⋅ 1946197 MLS ⋅ N/A BLDG.
7566 West Harbor Highway is the dream beach escape conjured in an easy summer read or as the backdrop to your favorite, cozy film. It's nestled along the shores of Sleeping Bear Bay, within a short distance of charming, downtown Glen Arbor, and sits in the heart of the peaceful, Sleeping Bear Dunes National Lakeshore. Its decking wraps around both cottages, creating meandering spaces and walkways to soak in the turquoise waters, breathtaking scenery, the scent of lake air, and the gentle rustle of the surrounding hardwoods and pines. This property consists of two original cottages, filled with charm but updated with comfort in mind. Between the two, there are four bedrooms, two and one half bathrooms, two kitchens, two fireplaces, and a screened in porch on each cottage. The walls are lined with ship lap, a welcoming addition to any classic cottage setting. Sitting just next to the main, waterside cottage, is a separate little cottage, entirely its own screened in porch, outfitted like an additional living room. It's where you sip your morning coffee covered by a blanket, laugh with friends over a cocktail or glass of wine, play board games with your kids, or read away a rainy day. Dare we say it's even the ideal home office? This is a space that beckons comfort, lightheartedness, relaxation, ease, and a sense of peace. A place where nothing surrounding you is too precious to use or to touch, but is instead meant to act as a serene backdrop to the incredible memories you'll make. This is beach living in the way it was meant to be.

7566 W Harbor Highway, Glen Arbor

4868 W Whispering Pines Lane, Glen Arbor
$3,450,000
4 Beds ⋅ 5 Baths ⋅ 1945399 MLS
Set on the coveted south end of Big Glen Lake with 90 feet of private sandy frontage, this stately cedar shake and brick residence offers a rare opportunity to create generations of memories in one of Leelanau County’s most treasured settings. Designed for gathering and relaxed lakefront living, the 4,041 sq ft home features four bedrooms plus additional den and recreation spaces, offering flexibility for hosting family and friends year-round. A welcoming brick courtyard framed with seasonal blooms creates an elegant first impression, while inside, expansive lake views and warm gathering spaces invite connection. The thoughtfully designed kitchen offers extensive cabinetry, abundant counter workspace, a center island, double ovens, and a unique fold-up countertop bridge connecting the island to the counter—perfect for additional prep space, casual dining, or buffet-style entertaining. Oak hardwood flooring flows from the foyer and hall through the kitchen and dining area, complementing the home’s timeless character and comfortable layout. The living room centers around a wood-burning fireplace, creating a cozy gathering place after long days on the lake while expansive windows frame beautiful views of Big Glen Lake. The main-floor primary suite, main-floor laundry, and oversized two-car garage with built-in storage provide convenience for everyday living, while the additional guest bedrooms, den, and rec room offer plenty of space for multi-generational enjoyment. Outside, two spacious lakefront patios provide exceptional outdoor living with ample room for grilling, entertaining, dining, and sunbathing just steps from the shoreline. Spend your days boating, swimming, paddleboarding, or relaxing along the sandy beach while taking in panoramic lake views. Perfectly positioned near renowned local favorites Funistrada and La Becasse, this combines peaceful waterfront living with convenient access to Sleeping Bear Dunes, and Glen Arbor.

4868 W Whispering Pines Lane, Glen Arbor

4515 W Glen Eden Drive, Glen Arbor
$2,102,000
2 Beds ⋅ 2 Baths ⋅ 1945137 MLS ⋅ Metes And Bounds BLDG.
A beautiful and unique offering of a charming cottage and pole barn with 125' of Big Fisher Lake frontage, located on close to an acre of land. A serene, deep, manicured lawn opens up to a dock that is just a short jaunt across the lake to the channel leading to Big Glen Lake. This 1950's cottage retains its original charm while also being updated for comfort and livability, and has over 1,600 square feet of living. There are two sizable bedrooms, well sized closets, and two bathrooms, both with walk-in showers, and one with an additional soaking tub. There's a light and airy kitchen, spacious family room and dining area, and attached one car garage, as well. The detached pole building has an additional two car garage, currently being used for boat storage, and has a small living quarter area attached with sleeping bunks and a half bathroom (this is additional square footage to what is listed). Whether you're spending time beneath the trees on the expansive front porch, or taking in the Fisher Lake views from the back deck or dock, this is a heavenly little slice of Leelanau. Seller is a licensed realtor in the state of Michigan.

4515 W Glen Eden Drive, Glen Arbor

5823 Sylvan Court, Glen Arbor
$1,905,000
4 Beds ⋅ 4 Baths ⋅ 1942610 MLS ⋅ Sylvan Shores BLDG.
THE BEST OF BOTH WORLDS! A rare offering of a spacious four bedroom, four bathroom home located in the heart of downtown Glen Arbor, but in a quiet cul-de sac with 60 ft of shared Lake Michigan frontage that can only be utilized by the residents who reside on Sylvan Court! The main floor of the home boasts a spacious living room with fireplace, a charming kitchen, and a mother-in-law suite with additional kitchenette. Off the kitchen is a large dining space and adjacent screened in porch. The lower level has a built in bunk area in its living room space, as well as two additional bedrooms and an additional bathroom. A two car attached garage and outdoor shower and kayak storage area make retaining your summer and seasonal items a breeze! The home is intelligently equipped with Geo furnace heat and air conditioning. House is in a rental program and has an excellent rental history. Sold with most furnishings.

5823 Sylvan Court, Glen Arbor

3 Vantage Pointe, Glen Arbor
$1,825,000
3 Beds ⋅ 3 Baths ⋅ 1948457 MLS ⋅ The Homestead BLDG.
Vantage Pointe is a highly sought after and exclusive area of The Homestead ~ an enclave of condominiums that feel much more akin to private homes, perched along one of the highest bluffs in the resort. The vistas allow for a clear view of Sleeping Bear Point, the blue and turquoise waters of Lake Michigan, as well as the North and South Manitou Islands. Upon pulling in to the property, there is abundant private parking and a two car detached garage. A tastefully adorned pathway lined with blooming flowers leads you to a soothing water feature and a courtyard that is peaceful and private. Extensive, fully irrigated landscaping surrounds the property providing year-round beauty and privacy. Through the front door, a bright, warm, and welcoming entryway and gourmet kitchen beckons one inside, with clear views of sparkling waters in the distance. Pass through the dining room with its charming, oil lit chandelier, and in to the living room, with its beamed ceilings, stone, wood burning fireplace, and expansive views. It's adjacent to a beautiful home office with the same, spectacular views. On the main floor of the property, there is a primary suite with a sliding door to the garden patio, an en-suite bathroom, as well as an additional powder room. One can't miss one of the hallmarks of this remodel - the captivating staircase of reclaimed Michigan barn wood that leads upstairs to the main primary suite with more spectacular views of Sleeping Bear Point, which is highlighted on the third level. A small deck is just off the upper floor primary suite for taking in one of the famous, west facing sunset views. In the lower level, a granite topped bar with custom cabinetry and built in beverage station greets you, as well as the ping pong/pool table area, and customized home theatre with surround sound and six leather recliners. A large laundry room, oversized storage room, and additional bedroom with lake views and en-suite bathroom round out this incredible space.

3 Vantage Pointe, Glen Arbor

5450 W MacFarlane Road, Glen Arbor
$1,520,000
3 Beds ⋅ 2 Baths ⋅ 1941509 MLS ⋅ Metes And Bounds BLDG.
If you've been waiting for a beautiful waterfront location to come along on Big Glen Lake - here it is! 5450 W. MacFarlane Rd. With a very level lot, perfect views of Alligator Hill and west facing sunset vistas, on over half an acre of land and with a well-kept home to customize and make your own - this property is calling your name! While the original footprint of the cottage is from the 1940's, it was rebuilt from the ground up in the late 1990's, and boasts three bedrooms, an additional sleeping space, two full bathrooms, laundry, air conditioning, and the most beautiful fieldstone fireplace in its light and airy living room! Expansive views of the lake are welcomed in through the living room windows, and the adjacent, open kitchen and dining area also allow for the same. There's a main floor primary bedroom, bathroom and laundry, with an additional two bedrooms, bathroom, and sleeping space upstairs! Outside, the 61' of Glen Lake frontage also comes with a brand new dock that is being included in the sale of the home! A detached, two car garage is ideal not only for parking, but for off season storage of kayaks, bikes, patio furniture, and more. This is a competitive price point for Big Glen Lake. Being sold furnished with few exceptions!

5450 W MacFarlane Road, Glen Arbor

23 South Beach, Glen Arbor
$1,400,000
4 Beds ⋅ 3 Baths ⋅ 1948038 MLS ⋅ The Homestead Resort BLDG.
Situated along Lake Michigan's shoreline in the southernmost portion of The Homestead, less than one mile from downtown Glen Arbor, is South Beach 23. This full ownership condo is a lower level unit that walks directly out to the beach. It has four bedrooms, three bathrooms, two decks, and two living areas to accommodate almost any family or group! Updates include fresh paint, newer flooring, bathrooms, wet bar in lower level, and a more updated kitchen. Enjoy strolls along the water and breathtaking sunsets. The Crystal River is just a short walk away for tubing and kayaking, as well, and all restaurants, shops, wineries and galleries are at your fingertips. Sold furnished with some exceptions.

23 South Beach, Glen Arbor

10 Vantage Pointe, Glen Arbor
$1,400,000
3 Beds ⋅ 4 Baths ⋅ 1939840 MLS ⋅ The Homestead BLDG.
Some things are just worth the wait... This beautiful property will be available for possession in August of 2026. Stunning views of majestic Lake Michigan, Sleeping Bear Point, and the Manitou Islands from nearly every angle of this home in Vantage Pointe! Whether during the peak of summer, fall colors, or as the snow falls, there is quite possibly no better view in The Homestead (or even in Glen Arbor) for taking in sunset! The spacious, open floor plan of this three bedroom, four bathroom home located at The Homestead offers many possibilities for making this your own, unique space. Being an end unit in the Vantage Point Association, there's a large deck for entertaining and taking advantage of the spectacular views that is directly off the main floor living, dining and kitchen area. There's a main floor primary bedroom with its own lake view/deck access, and a large, en-suite bathroom, as well as a second bedroom and bathroom on the main floor. Upstairs, there's a lofted space used as an additional bedroom with a Jack and Jill bath, and office area with potential for different uses. An oversized, finished basement/family room (which also accommodates an additional bedroom with egress windows and a full bathroom) boasts a wet bar, laundry room, and a large, tiled space perfect for a billiards room, game room, or simply ample storage! Use your creativity! Two fireplaces, heat and air conditioning, cathedral ceilings, newly replaced skylights, and a two car detached garage add to the attractiveness of this terrific opportunity. This property has been well cared for and loved, and it shows! Sold furnished with some exceptions.

10 Vantage Pointe, Glen Arbor

4 Chimney Ridge, Glen Arbor
$1,250,000
4 Beds ⋅ 5 Baths ⋅ 1946381 MLS ⋅ The Homestead BLDG.
Chimney Ridge 4 is a beautiful and spacious private home, boasting nearly 3,500 square feet of living, perched along the ski hills of The Homestead with views of Big Glen Lake. It's within a short walk to the Village of the resort and near downtown Glen Arbor. The first element of this home that will draw you in isn't just the light flooding through the living room and dining room, the soaring sealings, or the expansive kitchen. The biggest draw (at least for us), is the beautiful, top of the line TimberTech Advanced PVC decking, upgraded in 2025. It's maintenance free, long lasting, has been upgraded for harsh weather conditions, looks beautiful, and it spans all external stairs, the front door landing, the main deck, and the deck off the upper floor primary bedroom. In this same vein, in 2026, all new door walls and windows on the main level and back of the house were installed. With this home, so much of its wonderful quality is the view and the outdoor space - and all of it is top tier in Chimney Ridge 4! Inside the main level of the home, there's a soaring, two story ceiling over the living space, a sleek, woodburning fireplace, an oversized kitchen perfect for entertaining, the first laundry space off a main hall closet, a powder room, and a main floor primary suite (there's an even larger one upstairs!). Moving up to the second level, past the built in bookshelves and office nook, is an entire floor of a primary suite. This bedroom also has its own gas fireplace, built in bookshelves, private deck with Glen Lake views, and not just one bathroom, but two with their own separate vanities, toilets, and a walk-thru shower that can be accessed from each bathroom. But we're not done yet! There's a full, walkout lower level with light streaming in to its living space, as well. This lower level is home to a third fireplace, two additional living room spaces, two more bedrooms and bathrooms, walkout access to the ski hill, and an attached, three car garage!

4 Chimney Ridge, Glen Arbor

6 Twisted Oak, Glen Arbor
$985,000
3 Beds ⋅ 3 Baths ⋅ 1948094 MLS ⋅ Woodstone BLDG.
There are places that ask you to slow down the moment you arrive, and Woodstone is one of them. Tucked among mature hardwoods in one of Glen Arbor's most sought-after neighborhoods, this beautifully refreshed home offers the perfect balance of peaceful surroundings and effortless access to everything that makes life in Leelanau County so special. Here, quiet mornings begin with coffee on the deck, afternoons spent on the shores of Lake Michigan or enjoying a round of golf, and evenings end with dinner in downtown Glen Arbor before making the short trip home beneath a canopy of trees. Inside, you'll find warm, comfortable living spaces with updates that allow you to move in with confidence and immediately begin enjoying your Up North lifestyle. Recent improvements include fresh interior paint throughout, new upstairs carpeting, a new furnace installed in 2025, and updated kitchen and laundry appliances including a new refrigerator, dishwasher, washer, and dryer. Beyond your front door, the Woodstone community offers a lifestyle that is difficult to duplicate. Walk to nearby pickleball and tennis courts, browse local art galleries, enjoy Glen Arbor's restaurants and shops, or take a short bike ride to the Lake Michigan shoreline. When adventure calls, Sleeping Bear Dunes National Lakeshore, Big and Little Glen Lakes, championship golf, wineries, and the charming villages of Leland and Empire are all just minutes away. With the convenience of municipal sewer, a peaceful neighborhood setting, and one of Northern Michigan's most desirable locations, this is more than a home. It's an invitation to experience Glen Arbor the way it was meant to be lived.

6 Twisted Oak, Glen Arbor

28 Loggers Run, Glen Arbor
$825,000
3 Beds ⋅ 2 Baths ⋅ 1944947 MLS ⋅ The Homestead BLDG.
Stunning blue and aqua views of Lake Michigan and Sleeping Bear shorelines greet you from every inch of the living space in this fully renovated 3 bed, 2 bath condo at The Homestead. Sitting on the ridge like a treehouse with a sunset view, 28 Loggers Run is truly spectacular and unmatched. Sparkling updated kitchen, lofted ceilings, panoramic views, tasteful fresh decor, new furniture and bedding, a wood fireplace, newer appliances, and decks on both the water side and sunrise side in the trees off the primary. Delivered with everything that is needed to start enjoying your full ownership immediately. Fully renovated in 2018. Owners have recently replaced the washer, dryer, dishwasher, all bed frames in the home and upgraded to quality organic mattresses in the primary and 2nd bed, as well as new trundle mattress in guest room, new dresser, new dining table, and all dishware and glassware. There is an outdoor storage closet at the parking lot. Excellent rental history, information upon request. Please know there are a significant number of stairs to reach the unit, and this view is well worth it.

28 Loggers Run, Glen Arbor

31 Wilderness, Glen Arbor
$699,000
3 Beds ⋅ 2 Baths ⋅ 1950221 MLS ⋅ The Homestead BLDG.
This is the condo in The Homestead so many of you have been anticipating! Located in the south entrance of the resort and directly on the Crystal River, it also has beach access just steps away (with three fire pits available!), as part of the Wilderness Association is located on Lake Michigan. Being situated in the south entrance of the resort, it's also an easy walk, bike ride or drive in to downtown Glen Arbor, and is only a 5 mile drive to the Sleeping Bear Dunes. The aptly named Crystal River is ideal for tubing, kayaking, fishing, and is as clean and pure as rivers come! Lake Michigan has a solid, sandy beach, and clear, rippled sand beneath its turquoise waters. It doesn't get much better! Inside, Wilderness 31 is a light filled, tastefully decorated, three bedroom (one is a lofted bedroom) two bathroom townhouse style condo with a wide open living and dining space, one bedroom and bathroom on the main floor, and two bedrooms and an additional bathroom on the second floor. The vaulted, cedar ceilings and cozy, riverside aesthetic add to the appeal. It can comfortably accommodate 8 people. *It is also being sold furnished with few exceptions* Strong rental history.

31 Wilderness, Glen Arbor

9 Ridge Top, Glen Arbor
$680,000
2 Beds ⋅ 2 Baths ⋅ 1946054 MLS ⋅ The Homestead Ridge Top BLDG.
One of the very best views of Sleeping Bear Bay in both The Homestead and Leelanau County! Stunning vistas of turquoise water, the Manitou Islands, and Sleeping Bear Point from this two bedroom, two bathroom, freshly remodeled condo in The Homestead. West facing sunsets bring in even more magic! Two wood-burning fireplaces (in the living room and primary bedroom), private baths for both bedrooms, and an open concept living, kitchen, and dining area complete the space. The primary bedroom also has sweeping views of Lake Michigan, and the secondary bathroom has an in-condo washer and dryer. All spaces are tastefully designed, decorated, and allow for a light, breathable space that highlights the phenomenal scenery! New flooring, paint, kitchen and bathrooms, as well as a new doorwall slider in the primary bedroom, and a new roof on the Ridge Top Association! Excellent rental history. Sold furnished with a few exceptions, making this almost entirely turn-key. Don't miss this gem! *This property currently has rentals in place with The Homestead Resort in the summer of 2026.

9 Ridge Top, Glen Arbor

4 Tall Timber Unit #D3, Glen Arbor
$450,000
1 Beds ⋅ 1 Baths ⋅ 1947200 MLS ⋅ The Homestead BLDG.
A fantastic water view location in The Homestead! This one bedroom, one bathroom, mid-level condo in Tall Timbers provides lovely Lake Michigan, Crystal River, and western facing sunset views. The Crystal River is directly in front of the condo for easy access to tubing, kayaking, or fishing, and just over the very near by foot bridge is the stunning Lake Michigan beach for walking, sunbathing, swimming, and general enjoyment! This light and breezy space has white, tongue and groove paneling along the walls, white kitchen cabinets, white bathroom cabinetry, a newer oven/range, and every convenience needed. There is great ease of use with this turn-key property that is sold furnished with some exceptions. Heat, air conditioning, in-building laundry, storage lockers and parking directly in front of the building all make this a comfortable space to make your getaway!

4 Tall Timber Unit #D3, Glen Arbor

47 Hawks Nest, Glen Arbor
$450,000
2 Beds ⋅ 2 Baths ⋅ 1942029 MLS ⋅ Homestead Resort BLDG.
Whole ownership. Peaceful forest views in the Hawks Nest condominium association at The Homestead. Just a few hundred foot walk to the ski hills of the resort. The screened in upper level porch offers views of towering trees, and the gentle, sloping hillside, and the lower level porch offers another way to enjoy summer breezes and crisp, winter snowfalls. Two bedrooms, two bathrooms (one with a walk in shower, and the other with a tub/shower combo), a wood burning fireplace (so cozy for fall and winter nights!), a full kitchen and in-condo laundry (in a convenient location in the lower level bathroom) make this the perfect getaway or even full time residence. Many updates have taken place in this condominium, including newer flooring, paint, countertops, bathroom vanities, fixtures and more! ?Sold entirely furnished (dishes and all!) with the exception of artwork and personal items. If you are looking to purchase and rent, this condo is in an excellent location for both summer and winter rentals!

47 Hawks Nest, Glen Arbor

D2 Tall Timber, Glen Arbor
$385,000
1 Beds ⋅ 1 Baths ⋅ 1944838 MLS ⋅ The Homestead Resort BLDG.
On the banks of the Crystal River, just steps to a pristine sand dune and the Lake Michigan beachfront at The Homestead Resort, is this move-in ready studio featuring up-to-date furniture, West Elm outfitted kitchenette, plush bedding, and all the latest electronics...a beautiful place to relax and enjoy! From the convenient gated parking lot by the beach to the footbridge to cross the river, you will experience breathtaking nightly sunsets. This 295 sq ft condo is equipped with heat and air conditioning, a Roku Smart TV, fast WiFi for internet access, and an Amazon echo for playing music from streaming devices. Fresh updates include new paint, new fixtures, and all new furniture throughout including a luxurious queen sized bed, leather sofa, and comfy boucle chairs. The condo has a full bath with a shower/tub combination, and a kitchenette complete with West Elm design. Walk the beach, and stroll along the riverbank or boardwalk just outside the condo building. Climb the dunes, kayak the river. hike or bike the nearby paved Heritage Bike Trail to scenic Northern Michigan destinations. Enjoy four seasons of outdoor recreation and a beautiful place to call your home away from home. This freshly updated condo is only two miles from the town of Glen Arbor. This unit currently has rental nights booked between early May and early October that will be honored and buyer will collect rental income for dates that occur after closing.

D2 Tall Timber, Glen Arbor

5707 (5A) S Lake Street Unit 5G, Glen Arbor
$385,000
2 Beds ⋅ 3 Baths ⋅ 1942441 MLS ⋅ Le Bear Resort BLDG.
Experience your own slice of paradise in one of the most coveted units at LeBear Resort! This exclusive 2-bedroom, 2.5-bathroom retreat features a well-appointed den with a queen pull-out sofa, offering plenty of space for family and friends. Inside, you'll find a gourmet kitchen, two cozy gas fireplaces, and stunning views of Lake Michigan. Step outside to your private wraparound deck--complete with patio furniture and a grill--or head down to your own private beach frontage with kayaks and paddle boards at your disposal. Enjoy breathtaking western-facing sunsets overlooking Sleeping Bear Point and the Manitou Islands. The resort itself offers both indoor and outdoor pools, a shared clubhouse, billiards table, kitchen, and gym. Agent Remarks Showings to be scheduled on Fridays between 12pm-2pm. ? fractional interest ownership with 6 weeks each year on a rotation schedule. Weeks owned run Friday to Friday. Le Bear closes for two weeks in early May and in early November for maintenance weeks. Buyer's agent to verify all measurements.

5707 (5A) S Lake Street Unit 5G, Glen Arbor

18 South Village, Glen Arbor
$362,500
1 Beds ⋅ 1 Baths ⋅ 1950171 MLS ⋅ The Homestead Resort BLDG.
Whole ownership. This cozy, lower level, one bedroom, one bathroom condominium in the hillside of The Homestead is only a 10 minute walk to Lake Michigan and the Crystal River (and also mere steps from the "Village" of the resort, Whisker's outdoor bar, Cavanaugh's convenience store, the ski hills and cross country trails!). This condo has a spacious living room with a wood burning fireplace, an adjacent outdoor deck, and is open to the kitchen and dining space. The bedroom is located on the same level, as is the bathroom, which has a Jacuzzi tub, shower, and two vanities. This property is also equipped with an efficiency kitchen, washer and dryer hookups, and parking directly in front of the building. There's a walking path just steps away which meanders down to the Lake Michigan beach and the Crystal River in an under 10 minute walk! And, just outside its front door, there's also an owners' storage shed for storage. Sold furnished.

18 South Village, Glen Arbor

5707 (6A) S Lake Street Unit #6A, Glen Arbor
$355,000
3 Beds ⋅ 3 Baths ⋅ 1944684 MLS ⋅ Le Bear Resort BLDG.
Fractional, 1/8 share ownership on Lake Michigan in downtown Glen Arbor at the luxury resort, Le Bear! This beautiful property boasts both an indoor and outdoor pool, full concierge service, daily housekeeping, a shared clubhouse with a bar, billiards table, kitchen and gym, private parking and a one car garage each. Phenomenal views of Sleeping Bear Bay and the Manitou Islands with western facing sunset views. Le Bear is Part of "The Registry Collection." Not a detail was spared in creating this incredible fractional ownership experience. The condos themselves have two bedrooms, a den with a murphy bed, two and one half bathrooms, a gourmet kitchen, two fireplaces (in this unit - both in the living room and family room spaces), incredible Lake Michigan views, decks with patio furniture and a grill, beach access, and are located adjacent to the fabulous fine dining restaurant, Blu. Each condo is decorated in the same, tasteful style, and the fractional ownership unit available, 6A, is a mid level unit (and there is an elevator available!). The 1/8th fractional ownership is broken down to each share having 6 weeks of use on a rotating calendar- 1 full week at a time. The calendar rotates every year so that every owner experiences different weeks. Owners have the option to rent their weeks, which can be very effective at covering association costs and taxes.

5707 (6A) S Lake Street Unit #6A, Glen Arbor

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