1,339

Winter Haven, FL Homes for Sale

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  • /30

    $285,900

    • 3 Beds
    • 2 Baths
    • 1,537 Sq Ft

    1518 Fuji Ct, Winter Haven, FL 33881

    Discover resort-style living in this charming 3-bedroom, 2-bath home built in 2023, nestled in the amenity-rich Villages at BridgeWater community. Boasting 1,537 sq ft of modern comfort on a 5,998 sq ft lot, enjoy an open floor plan with vaulted ceilings, a modern kitchen with large island, and a private primary suite. Community perks include a pool, fitness center, tennis courts, and a

    John Crusinberry MARK SPAIN REAL ESTATE

    1518 Fuji Ct, Winter Haven, FL 33881
  • /41

    $269,000

    • 3 Beds
    • 2 Baths
    • 1,913 Sq Ft

    624 Avenue A NE, Winter Haven, FL 33881

    Experience the perfect blend of "Old Florida" soul and modern peace of mind in the heart of the desirable NE downtown grid! This enchanting 1937 vintage gem at 624 Avenue A NE has undergone a comprehensive mechanical evolution over the last 6 months, making it one of the most insurance-friendly historic homes on the market. Major 2025/2026 Upgrades Include:NEW ROOF (6 months old)NEW AC

    Veronica Bard LA ROSA REALTY PRESTIGE

    624 Avenue A NE, Winter Haven, FL 33881
  • /32

    $98,800

    • 2 Beds
    • 2 Baths
    • 1,344 Sq Ft

    502 Leyland Cypress Way Unit 61, Winter Haven, FL 33881

    CYPRESS CREEK VILLAGE #61 / 2 BED / 2 BATH / 1,344 SF / $98,800 POND VIEW HOME with Double Driveway! This Large WELL MAINTAINED updated home is partially furnished and move-in-ready for you! This 2006 Nobility Home features an open floor plan and large two-level lanai overlooking a pond! Lanai includes tile floors, vinyl windows, roman shades, and a covered patio that is perfect for grilling out!

    Jennifer Meyers CRF Communities

    502 Leyland Cypress Way Unit 61, Winter Haven, FL 33881
  • /54

    $230,000

    • 2 Beds
    • 2 Baths
    • 1,682 Sq Ft

    2813 Wingfoot Ct, Winter Haven, FL 33884

    Welcome to 2813 Wingfoot Court in the sought-after Cypresswood Golf Villas! Perfectly positioned along the 8th fairway of Cypresswood Golf & Country Club, this guard-gated community offers peaceful golf course views and a relaxed Florida lifestyle.This beautifully maintained 2-bedroom, 2-bathroom villa is being sold fully furnished and truly turn-key — just bring your suitcase. The professionally

    Corinna Weaver CROSBY & ASSOCIATES, INC.

    2813 Wingfoot Ct, Winter Haven, FL 33884
  • 1651 Hummingbird Rd Unit 39009648, Winter Haven, FL 33880

    $462,990 New Construction

    • 4 Beds
    • 3.5 Baths
    • 2,787 Sq Ft

    Camden Plan at Harmony at Lake Eloise, Winter Haven, FL 33880

    Harmony at Lake Eloise presents The Camden, available to build in Winter Haven, FL. This all-concrete block constructed, one-story multi-gen layout offers two homes under one roof. As you enter the foyer you are greeted with two guest bedrooms that share an en suite bathroom with a double vanity. Making your way down the hall you will find a large dining room perfect for the whole family. The

    D.R. Horton Builder
    1651 Hummingbird Rd Unit 39009648, Winter Haven, FL 33880
  • /59

    $589,900

    • 4 Beds
    • 3 Baths
    • 2,633 Sq Ft

    333 Lake Otis Dr SE, Winter Haven, FL 33880

    Welcome to this beautifully renovated pool home offering modern luxury, privacy, and ultimate functionality all with no HOA restrictions! Situated on a spacious corner lot, this 3-bedroom, 3-bath residence includes a dedicated office perfect for working from home or a 4th guest room. Inside, you'll find a brand-new designer kitchen with premium cabinetry, solid countertops, and stainless-steel

    Colin Wells SIGNATURE PROPERTIES OF CENTRAL FLORIDA LLC

    333 Lake Otis Dr SE, Winter Haven, FL 33880
  • /64

    $775,000

    • 4 Beds
    • 4 Baths
    • 3,440 Sq Ft

    2683 Wyndsor Oaks Way, Winter Haven, FL 33884

    Back on market, property passed inspections already. Welcome to 2683 Wyndsor Oaks Way, Winter Haven, FL – an extraordinary residence in the highly sought-after gated Wyndsor at Lake Winterset community, offering a luxurious lifestyle with lake access, tennis courts, and a playground. This stunning home blends timeless elegance with modern comforts, creating a perfect sanctuary for discerning

    Patricia de Graaff RE/MAX HERITAGE PROFESSIONALS

    2683 Wyndsor Oaks Way, Winter Haven, FL 33884
  • /23

    $149,500 Open House 3/22

    • 2 Beds
    • 2 Baths
    • 1,073 Sq Ft

    413 Winter Ridge Blvd Unit 90, Winter Haven, FL 33881

    Welcome to Winter Ridge Condominiums — Lakeside Living on the Winter Haven Chain of Lakes. Discover the charm of Winter Ridge, a desirable waterfront condominium community offering direct access to Lake Smart, part of the renowned Winter Haven Chain of Lakes. This inviting 2-bedroom, 2-bath home features an open floor plan with ceramic tile throughout, a galley-style kitchen equipped with a

    Christina Heath Century 21 Myers Realty

    413 Winter Ridge Blvd Unit 90, Winter Haven, FL 33881
  • /56

    $198,000

    • 2 Beds
    • 2 Baths
    • 1,620 Sq Ft

    492 Lakeside Ranch Cir, Winter Haven, FL 33881

    LAKEFRONT LIVING FOR UNDER $200K, MOTITVATED SELLER!!! Why pay lot rent when you can enjoy the charm and tranquility in this beautifully renovated, Fully Furnished 2 Bedroom/2 Bath 2006 home in Winter Haven! Nestled in the serene, gated 55+ Lakeside Ranch community on Lake Henry. This home is move-in ready and offers a host of modern updates, including New HVAC (2025) and New Roof and All New

    Cheryl Brewer COLDWELL BANKER REALTY

    492 Lakeside Ranch Cir, Winter Haven, FL 33881
  • /13

    $1,100,000

    • Land
    • 1.4 Acres
    • $785,714 per Acre

    0 Cypress Gardens Rd Unit MFRL4957987, Winter Haven, FL 33884

    Prime 1.4+-acre Commercial site adjacent to CVS Hard Corner with separate shared entrance to service the surrounding properties. 100+ Newly Constructed Apartment Facility wraps around northerly & westerly sides of the subject 1.4+-acres. Ideal for another prime medical facility benefiting from the nearby Emergency Centers, Eye Center, Cancer Treatment Facility,etc..

    Gregory Karlson ADVANTAGE REALTY 1

    0 Cypress Gardens Rd Unit MFRL4957987, Winter Haven, FL 33884
  • /28

    $148,900

    • 2 Beds
    • 2 Baths
    • 1,568 Sq Ft

    1221 Cypress Vine Rd Unit 256, Winter Haven, FL 33884

    Lot #256 - 2 Bed /2 Bath + Den /1,568 Sq. Ft./$148,900.00 Spectacular Pond Views from this 2016 Ashley Model in beautiful Cypress Creek Village! This spacious home is located on a waterfront lot with breathtaking views! It offers a double carport with an additional golf cart path! This gorgeous home offers: *Vaulted Ceilings *Kitchen with coffee station and pantry *French doors into large den

    Jennifer Meyers CRF Communities

    1221 Cypress Vine Rd Unit 256, Winter Haven, FL 33884
  • /45

    $45,000

    • 2 Beds
    • 2 Baths
    • 840 Sq Ft

    564 Chickasaw Loop Unit 34, Winter Haven, FL 33881

    Hidden Cove East / Lot #34 / 2 Bedroom/2 Bath / 840 Sq. Ft. / $45,000.00 PRICE REDUCED ALMOST 3K!!! This home is located in the beautiful Hidden Cove East community, and is unusually hard to find a home as gorgeous as this one! Once residents purchase, they stay, so homes do not come on the market very often. Jump on this gorgeous home that has: New A/C Compressor Roof (2 years old) Sprinkler

    Jennifer Torres CRF Communities

    564 Chickasaw Loop Unit 34, Winter Haven, FL 33881
  • /2

    $21,450

    • Land
    • 0.5 Acre
    • $42,900 per Acre

    0 Valencia Dr SE, Winter Haven, FL 33884

    Keith Rappa Rappa Realty Group LLC

    0 Valencia Dr SE, Winter Haven, FL 33884
  • /22

    $285,000 Open Sat 9AM - 7PM

    • 3 Beds
    • 2 Baths
    • 1,757 Sq Ft

    7010 Summit Cir, Winter Haven, FL 33884

    Welcome to this beautifully maintained property located at 7010 Summit Cir. The living room sets a welcoming tone with fresh interior paint lending a modern, clean feel, while tasteful partial flooring updates add subtle elegance. The kitchen is a chef’s dream featuring all stainless steel appliances and a layout designed for effortless daily cooking. The bedrooms offer a peaceful retreat,

    Karen Albright OPENDOOR BROKERAGE LLC

    7010 Summit Cir, Winter Haven, FL 33884
  • /3

    $49,000

    • Land
    • 1.01 Acres
    • $48,515 per Acre

    0 N A Unit MFRO6227442, Winter Haven, FL 33880

    Vacant land for sale in Winter Haven, Florida (33880)! This 1.01-acre lot offers a great opportunity to build a custom spot or invest in a desirable Central Florida location. Enjoy the space, flexibility, and convenience of being close to local amenities while still having room to create your ideal retreat. Pin Location: Latitude 27.94512674, Longitude -81.74712260

    Samih Sadiq KELLY RIGHT REAL ESTATE

    0 N A Unit MFRO6227442, Winter Haven, FL 33880
  • /33

    $119,900

    • 2 Beds
    • 2 Baths
    • 1,439 Sq Ft

    1315 Las Brisas Ln Unit 611, Winter Haven, FL 33881

    2 Bedroom + Den | 2 Bath | 1,439 Sq Ft | $119,900 Four Lakes Golf Club Lot 611 Bright Open Layout Meets 2-Level Lanai for Ultimate Entertaining Welcome home to this beautifully maintained, entertainment-ready retreat located in the highly sought-after Four Lakes Golf Club community! With over 1,400 sq ft of thoughtfully designed living space, this 2-bedroom + den home offers comfort, style, and

    Cheryl Dobbs CRF Communities

    1315 Las Brisas Ln Unit 611, Winter Haven, FL 33881
  • /32

    $349,990 New Construction

    • 3 Beds
    • 2 Baths
    • 1,814 Sq Ft

    807 Andrew St, Winter Haven, FL 33881

    Welcome to the Baker floor plan a spacious 3-bedroom, 2-bath home with a versatile flex space designed to fit your lifestyle. As you walk through the front door, you’re greeted by a bright and inviting foyer that opens to two comfortable bedrooms at the front of the home, perfectly positioned around a beautifully appointed full bathroom. Down the hallway, you’ll find a convenient flex space ideal

    DRB Homes Builder
    807 Andrew St, Winter Haven, FL 33881
  • /28

    $174,500

    • 2 Beds
    • 2 Baths
    • 930 Sq Ft

    7904 Waterview Way Unit 7904, Winter Haven, FL 33884

    Welcome to resort-style living in the highly sought-after gated waterfront community of Winterset, where convenience meets comfort in this charming 2-bedroom, 2-bathroom downstairs condo. Step inside to discover a spacious living and dining room combo that creates an inviting atmosphere for relaxation and entertaining. The well appointed kitchen features stainless steel appliances and a

    David Small KELLER WILLIAMS REALTY SMART 1

    7904 Waterview Way Unit 7904, Winter Haven, FL 33884
  • /37

    $179,000

    • 3 Beds
    • 3 Baths
    • 1,749 Sq Ft

    332 Siberian Cypress Cir, Winter Haven, FL 33881

    **CHARMING 3B/3B HOME IN A 55+ PET FRIENDLY GATED COMMUNITY! ** Welcome to your new sanctuary in a vibrant 55+ gated community in beautiful Winter Haven Florida! This stunning like new 2022 Scot Built Manufactured Home offers a generous 1,749 sq. ft. of thoughtfully designed living space, perfect for enjoying your golden years. This home features a spacious master suite where you can indulge in

    Mary Sergent USA Mobile & Manufactured Home Sales, LLC.

    332 Siberian Cypress Cir, Winter Haven, FL 33881
  • /39

    $350,000

    • 3 Beds
    • 2 Baths
    • 1,595 Sq Ft

    122 22nd St NW, Winter Haven, FL 33880

    Welcome to your dream oasis—a stunning craftsman-style 3-bedroom, 2-bath saltwater pool home nestled on just over a quarter acre. This charming property features a large front porch, perfect for relaxing with your morning coffee or enjoying beautiful sunsets. Step inside to find a warm and inviting interior with classic crown molding throughout. The formal dining room offers an elegant space for

    Tiffany Russell KELLER WILLIAMS REALTY SMART 1

    122 22nd St NW, Winter Haven, FL 33880
  • /17

    $269,900

    • 3 Beds
    • 2 Baths
    • 1,526 Sq Ft

    29 Enclave Dr, Winter Haven, FL 33884

    New to the market is this "one owner" villa located in the sought-after Enclave neighborhood located in Cypresswood Golf and Country Club in SE Winter Haven. This 3 bedroom 2 bathroom end unit is in the midst of a professional interior paint job. (new photos will be loaded after painting is complete) Enjoy Easterly pasture views from the lanai. Ideal for sunrise viewing. The country club

    Steven Smith, PA LOCKHART & ASSOCIATES INC

    29 Enclave Dr, Winter Haven, FL 33884
  • /30

    $359,950

    • 2 Beds
    • 2 Baths
    • 1,517 Sq Ft

    265 Lake Thomas Dr, Winter Haven, FL 33880

    Welcome to this beautifully renovated lakefront retreat on Thomas Lake in Winter Haven! This stunning two-story home combines modern upgrades with warm character and breathtaking water views.Step inside to tall vaulted ceilings creating an open, airy layout filled with natural light. The home features all-new flooring throughout and a completely updated kitchen showcasing stainless steel

    Angie Reynolds PORCHLIGHT HOMES LLC

    265 Lake Thomas Dr, Winter Haven, FL 33880
  • /28

    $99,900

    • 2 Beds
    • 2 Baths
    • 1,352 Sq Ft

    134 Lake Hazel Dr, Winter Haven, FL 33884

    2-Bedroom, 2-Bathroom Mobile Home in a 55+ Community of ORANGE MANOR WEST-NO LOT RENT!-This spacious 1,352 sq. ft. double wide mobile home located in a 55+ community that offers a wealth of amenities for an active lifestyle. BRAND NEW A/C! The living room features sliding glass doors that open to a front enclosed Florida room, perfect for enjoying the view of your front yard. The kitchen comes

    Kelley Vogel Blackburn COLDWELL BANKER REALTY

    134 Lake Hazel Dr, Winter Haven, FL 33884
  • /13

    $275,490 New Construction

    • 3 Beds
    • 2 Baths
    • 1,429 Sq Ft

    Belmont Plan at Peace Creek Reserve - Manor Key Collection, Winter Haven, FL 33884

    This new home is laid out on a single level for low maintenance living. Two secondary bedrooms share a bathroom in the hall at the front of the home, while the owner’s suite is tucked into the back corner with an attached bathroom and walk-in closet. Down the foyer is the open-concept living area, which includes a fully equipped kitchen, an intimate dining room and family room with patio access.

    Lennar Builder
    1108 Tyler Loop Unit 36037860, Winter Haven, FL 33884
  • /43

    $350,000

    • 3 Beds
    • 2 Baths
    • 2,431 Sq Ft

    1218 37th St NW, Winter Haven, FL 33881

    Welcome to this beautifully built home in a super convenient Winter Haven location. Its central position makes it easy to get anywhere you need to go. You are close to Legoland, an easy drive to Disney attractions, and have quick access to Florida's beaches, shopping, restaurants, and everyday essentials. Inside, the home features an impressive open concept design with soaring 12 foot ceilings,

    Prudy Cole CENTURY 21 BE3

    1218 37th St NW, Winter Haven, FL 33881
  • /16

    $119,900

    • 2 Beds
    • 2 Baths
    • 1,056 Sq Ft

    4526 Redwood St, Winter Haven, FL 33880

    Come enjoy the beautiful Florida sunsets, In this beautiful, furnished home. You can relax in the enclosed Florida room, Carport is long enough to put two cars in. floors have the beautiful laminate wood flooring, all through out the livingroom,and dining areas. All located in a beautiful gated 55 plus park. Two heated pools, two clubhouses, tennis ,fishing pier, minature golf, shuffle board,

    Rita Stead SOUTHERN BELLE REALTY

    4526 Redwood St, Winter Haven, FL 33880
  • /19

    $90,000

    • 2 Beds
    • 2 Baths
    • 1,152 Sq Ft

    4165 Rolling Oaks Dr, Winter Haven, FL 33880

    Priced to sell, Home has a new metal roof, CHA is approximately five years old, and you will feel right at home from the moment you walk in. Come enjoy the beautiful Florida sunsets in this 55+ gated, five-star park.

    Rita Stead SOUTHERN BELLE REALTY

    4165 Rolling Oaks Dr, Winter Haven, FL 33880
  • /89

    $85,000

    • 2 Beds
    • 2 Baths
    • 1,550 Sq Ft

    325 Lakeview Ln SE, Winter Haven, FL 33884

    ** Exclusive Listing! Age 55+ Land Lease Community with monthly lot rent. Contact listing agent below for ALL showings and offers.** You'll soon have your very own slice of Florida paradise as the new owner of this super spacious and exceptionally well maintained 1985 Fuqua. Priced right at $85,000, and measuring 25x52, plus the 10x25 Florida room, this home will provide approximately 1550 total

    Shawna Kemp Mobile Home Spot Inc.

    325 Lakeview Ln SE, Winter Haven, FL 33884
  • /20

    $209,900

    • 3 Beds
    • 1 Bath
    • 1,008 Sq Ft

    520 35th St NW, Winter Haven, FL 33880

    Winter Haven Single Family Residential home, 3B/1ba offers a well landscaped Corner Lot. The Interior accommodates Electric AC & natural gas heat. This home still boasts original well maintained kitchen cabinets & oven appliances. The Exterior features are Concrete Block Detached storage/workshop 20x14’, covered carport 20x12’, exterior lighting, irrigation well, pole barn for RV parking 28x20’

    Wendy Gibbs WATSON & WATSON INC REALTORS

    520 35th St NW, Winter Haven, FL 33880
  • /32

    $345,000

    • 4 Beds
    • 2 Baths
    • 1,727 Sq Ft

    2221 20th St NW, Winter Haven, FL 33881

    This beautifully updated 4-bedroom, 2-bath home offers the perfect blend of modern comfort and classic Florida living. Located directly across from the Lake Hartridge boat ramp and Lake Hartridge Nature Park, you’ll enjoy instant access to the Winter Haven Chain of Lakes—one of Central Florida’s most desirable waterways for boating, fishing, and recreation. Inside, every detail has been

    Stetson Russell REAL FLORIDA REALTY LLC

    2221 20th St NW, Winter Haven, FL 33881
  • /22

    $139,900

    • 2 Beds
    • 2 Baths
    • 1,077 Sq Ft

    689 Lake Howard Dr NW Unit 2D, Winter Haven, FL 33880

    Price Improvement!! Welcome to this Charming 2-bedroom 2 bath move-in-ready condo in the well-established 55+ Wellington Community. This community has a beautiful lake front with a private dock and access to Lake Howard that connects to the Chain of Lakes. This spacious home provides plenty of living space, with large bedrooms, and sliding doors that lead to a screened in lanai with a side rear

    Rick Hemenway CROSBY & ASSOCIATES, INC.

    689 Lake Howard Dr NW Unit 2D, Winter Haven, FL 33880
  • /73

    $335,000

    • 3 Beds
    • 2 Baths
    • 2,011 Sq Ft

    5264 Green Dr, Winter Haven, FL 33884

    5264 Green Drive Winter Haven, Florida is a 3 Bedroom/2 Bath Provence floor plan located in Lake Ashton, a gated and guarded 55+ community with resort style amenities and activities. This spacious and split floor plan home offers a Formal Dining Area, Living Room, Primary Suite, Guest Bedroom and Bedroom 3 is a Flex Room that could be an Office or additional Entertainment area. There is a closet

    Lori Raath LAKE ASHTON REALTY INC.

    5264 Green Dr, Winter Haven, FL 33884
  • /37

    $48,000

    • 2 Beds
    • 2 Baths
    • 1,484 Sq Ft

    277 Alpine Dr Unit 277, Winter Haven, FL 33881

    Swiss Village / Lot #277 / 2 Bed/2 Bath / 1,484 Sq. Ft. / LAKE VIEW FOR $48,000.00 PRICE HAS BEEN REDUCED ALMOST 5K!!! 4 POINT INSPECTION HAS ALREADY BEEN DONE!! This spacious home is right across from the water and on a corner lot. It provides: New Gutters & Fascia, Double carport, New Appliances, Refreshed Kitchen (with new countertops, paint, hardware), New Kitchen/bathroom LVP flooring &

    Jennifer Torres CRF Communities

    277 Alpine Dr Unit 277, Winter Haven, FL 33881
  • /38

    $105,000

    • 2 Beds
    • 2 Baths
    • 1,176 Sq Ft

    188 Sweet Cir, Winter Haven, FL 33884

    Become a share holder in this highly sought after 55+ gated community. If you are looking for the perfect retirement home, this one is for you! Located in Orange Manor West, it is one of the most popular 55+ communities in Winter Haven and surrounding area with many amenities. Pool, shuffle board, putt putt, horse shoes, crochet, bingo, lake access and much more. Legoland is around one mile away

    Chris Cain MOSAIC SERVICES LLC

    188 Sweet Cir, Winter Haven, FL 33884
  • /26

    $19,000

    • 2 Beds
    • 1.5 Baths
    • 800 Sq Ft

    424 Mockingbird Ave, Winter Haven, FL 33881

    Motivated Seller! Welcome to this charming 2-bedroom, 1.5-bath home nestled on a desirable corner lot in the beautiful 55+ community of Lake Deer Hamlet Mobile Home Park. Offering great value and comfort, this home features a spacious Florida room addition, perfect for relaxing, entertaining, or enjoying your morning coffee. A large storage shed provides plenty of space for tools, hobbies, or

    Lillian Lunsford TEAM SHERROD MOBILE HOME SALES, LLC.

    424 Mockingbird Ave, Winter Haven, FL 33881
  • /22

    $59,000

    • 2 Beds
    • 2 Baths
    • 1,215 Sq Ft

    11 Navel Dr, Winter Haven, FL 33884

    Seller is Motivated! Price Reduced! Welcome to this very well kept gem located in sunny central Florida in the quiet and tranquil neighborhood of orange manor 55+ community. With many amenities. Pool, shuffle board, putt putt, horse shoes, crochet, bingo, lake access and much more. Legoland is around one mile away! Become a share holder in this highly sought after 55+ gated community. This home

    Michael Dorman ELEVATE REAL ESTATE BROKERS

    11 Navel Dr, Winter Haven, FL 33884
  • /25

    $314,990

    • 4 Beds
    • 2 Baths
    • 1,851 Sq Ft

    3308 Country Walk Club Cir, Winter Haven, FL 33881

    Welcome to this stunning 4-bedroom, 2-bath home located in a vibrant and growing neighborhood. Built in 2020, this modern residence offers the perfect blend of style, comfort, and functionality—ideal for today’s lifestyle.Step inside to discover a bright and spacious open-concept floor plan, perfect for both everyday living and entertaining. The gourmet kitchen is a true centerpiece,

    Humberto Cuevas LA ROSA REALTY LLC

    3308 Country Walk Club Cir, Winter Haven, FL 33881
  • /38

    $358,500

    • 4 Beds
    • 3 Baths
    • 2,257 Sq Ft

    896 Vienna Dr, Winter Haven, FL 33884

    PRICE ADJUSTMENT LOWERED BY $11,500...YOU DON'T WANT TO MISS THIS OPPORTUNIY!!!LOOK AT THIS AMAZING MOVE IN READY HOME. Owner is ready to sell! This beautiful high-end Adams built home is located in SE Winter Haven. It is a stunning one story 4/3 move in ready home that was built in April 2022, less than a year old! When you enter the home, you will feel the magnitude of the open floor plan with

    Sherry Sapp COLDWELL BANKER REALTY

    896 Vienna Dr, Winter Haven, FL 33884

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