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Winter Haven, FL Homes for Sale under $300,000

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  • /25

    $259,000

    • 3 Beds
    • 2 Baths
    • 1,580 Sq Ft

    715 Avenue B SW, Winter Haven, FL 33880

    Opportunity awaits in the heart of Winter Haven! This 3-bedroom, 2-bath home offers approximately 1,580 square feet of living space on a generously sized lot. Inside, you'll find a functional floor plan with spacious living areas and a layout ready for your personal updates. The kitchen and bathrooms offer the opportunity to customize the home to your own style and preferences. Conveniently

    Benjamin Crane CITARELLI REALTY GROUP LLC

    715 Avenue B SW, Winter Haven, FL 33880
  • /40

    $265,000

    $15K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,602 Sq Ft

    3022 Hickory St NW, Winter Haven, FL 33881

    This move-in ready 3-bedroom Winter Haven pool home offers a fantastic combination of comfort, upgrades, and true Florida living on an oversized lot with no HOA. The home features a brand-new roof, new HVAC system and thermostat, new water heater, new pool pump and chlorinator, new laundry units, new exterior front doors, and an expanded driveway with ample parking. Inside, you’ll find a

    Ashlee Morrell THE URBAN GROUP, INC.

    3022 Hickory St NW, Winter Haven, FL 33881
  • /29

    $253,990

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,463 Sq Ft

    4718 Tony St, Lake Wales, FL 33859

    The property is located at 4718 Tony Street LAKE WALES FL 33859 priced at 253990, the square foot and stories are 1463, 2.The number of bath is 2, halfbath is 1 there are 3 bedrooms and 1 garages. For more details please, call or email.

    D.R. Horton Builder
    4718 Tony St, Lake Wales, FL 33859
  • /38

    $189,000

    $10K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 1,080 Sq Ft

    121 Bates Ave SE, Winter Haven, FL 33880

    Located in the heart of downtown Winter Haven, FL, this versatile R-3 zoned property presents an excellent opportunity for homeowners, investors, or those seeking future development potential! This charming residence features 2 bedrooms and 1 full bathroom, offering a functional layout with comfortable living spaces. The home includes a spacious kitchen with ample cabinetry and room for dining,

    Emily Jones RE/MAX REALTY PLUS

    121 Bates Ave SE, Winter Haven, FL 33880
  • /34

    $274,990

    New Construction
    • 4 Beds
    • 2 Baths
    • 1,625 Sq Ft

    4097 Penelope Ave, Lake Wales, FL 33859

    The Bradley floor plan is a well-designed one-story home featuring four spacious bedrooms and two bathrooms. This layout emphasizes an open concept, with the dining room flowing seamlessly into the great room, creating a bright and airy central living space perfect for gatherings. The kitchen offers easy access to the dining area, making meal times and entertaining more convenient. The owner’s

    Dream Finders Homes Builder
    4097 Penelope Ave, Lake Wales, FL 33859
  • /10

    $4,000

    • 1 Bed
    • 1 Bath

    620 Jenny Wren Rd Unit 620, Winter Haven, FL 33881

    This Handyman Home is located in a peaceful 55+ community on a quiet dead-end street. The home has been cleared out and ready for someone to make it their own. Home has Spacious screened porch - larger bedroom - huge storage area along the back of home -Washer/dryer hook-ups are located in the outdoor storage area for convenience. Unit is sold AS IS. Asking $4,000 or best offer. Don't miss this

    Yvonne Straub Lake Deer Mobile Hamlet

    620 Jenny Wren Rd Unit 620, Winter Haven, FL 33881
  • /30

    $279,990

    • 3 Beds
    • 2 Baths
    • 1,698 Sq Ft

    136 Krenson Bay Loop, Winter Haven, FL 33881

    Welcome to the Winter Haven community of Krenson Bay. This 3bd/2ba home was built in 2022 with the property condition like new! Move in ready with an open layout of kitchen/dining/family room combo. The kitchen has stainless steel appliances and a large island to host gatherings. Located close to major highways and LEGOLAND! Schedule your showing today!

    Lisa Manzo WIN-WIN REAL ESTATE SERVICES LLC

    136 Krenson Bay Loop, Winter Haven, FL 33881
  • /2

    $259,900

    New Construction $20K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,544 Sq Ft

    137 Nemo Ln, Winter Haven, FL 33881

    Move-in ready 3-bedroom, 2-story townhome with a garage for sale in Winter Haven, FL! Downstairs, enjoy an open living area with a spacious gathering room, plus a convenient powder room, a flex space, and a private covered lanai. Upstairs, relax in your private owner's suite with a walk-in wardrobe and a private en-suite bathroom including dual vanities, a decorative tiled shower, closeted

    Highland Homes Builder
    137 Nemo Ln, Winter Haven, FL 33881
  • /33

    $219,900

    $14K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,368 Sq Ft

    10 Enclave Dr, Winter Haven, FL 33884

    WELCOME TO THIS CHARMING TOWNHOUSE located in the sought-after Cypresswood Golf & Country Club community in beautiful Winter Haven! This inviting 2 BD / 2 BA home offers comfortable Florida living with a spacious open-concept living and dining room combination, abundant natural light, and a thoughtfully designed layout perfect for both relaxing and entertaining. The kitchen features beautiful

    Erin Floyd COLDWELL BANKER REALTY

    10 Enclave Dr, Winter Haven, FL 33884
  • /5

    $267,000

    • 3 Beds
    • 2 Baths
    • 1,451 Sq Ft

    412 Avenue M NE, Winter Haven, FL 33881

    This lovely 3/2 home is only 2years old. Only one previous owner and now the home currently tenant occupied. Everything new, backyard spacious and has lots of potential. This is one charming home in a nice neighborhood that is a must see!

    Julie Joseph Charles & Charles Realty LLC

    412 Avenue M NE, Winter Haven, FL 33881
  • /55

    $225,000

    $10K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,396 Sq Ft

    2115 Kings Crossing SW, Winter Haven, FL 33880

    *PRICE IMPROVEMENT*~2/2 Winter Haven residence Offered for Sale~Great opportunity for a first-time home buyer or an investor! This adorable 2/2 property features 1396 square feet of living area, a split plan, two bonus rooms which could be used as bedrooms, vaulted ceilings, primary bedroom with walk-in closet and en-suite bath, wood burning fireplace, large, screened patio and a one car

    Andrea Muzzy HOUSE OF GLASS REAL ESTATE PM

    2115 Kings Crossing SW, Winter Haven, FL 33880
  • /61

    $175,000

    • 2 Beds
    • 2 Baths
    • 1,224 Sq Ft

    6733 Kensington Dr NE, Winter Haven, FL 33881

    Charming 2-Bedroom, 2-Bath Home on a Corner Lot Near Lake Henry. Welcome to this beautifully maintained 2-bedroom, 2-bathroom home, where pristine evidence is noticed from the moment you arrive. From the unique guitar-themed driveway artwork to the immaculate interior, this inviting residence is ready for you to move in and enjoy.Situated on a desirable corner lot, the home is located on a

    Cynthia Cole FLORIDA REALTY MARKETPLACE

    6733 Kensington Dr NE, Winter Haven, FL 33881
  • /33

    $279,990

    New Construction
    • 4 Beds
    • 2 Baths
    • 1,758 Sq Ft

    5055 Abigail Dr, Winter Haven, FL 33859

    The Hillcrest floorplan is a spacious and thoughtfully designed one-story home that includes 4 bedrooms and 2 bathrooms, complemented by a two-car garage. This layout features a large great room at the heart of the home, seamlessly flowing into the dining area and kitchen for easy entertaining and family gatherings. The owner's suite is privately positioned and includes a walk-in closet and an

    Dream Finders Homes Builder
    5055 Abigail Dr, Winter Haven, FL 33859
  • /24

    $288,990

    New Construction
    • 4 Beds
    • 2 Baths
    • 1,665 Sq Ft

    HARPER Plan at VillaMar, Winter Haven, FL 33884

    Introducing the Harper floorplan at Villamar, where every square foot is put to use with sophistication and comfort. Inside this 4 bedroom, 2 bathroom home, you’ll find 1,665 square feet of comfortable living. This meticulously designed residence combines modern convenience with timeless elegance, showcasing granite and tile floors throughout. As you step inside, you are greeted by an inviting

    D.R. Horton Builder
    3744 Giorgio Dr Unit 36202856, Winter Haven, FL 33884
  • /20

    $79,900

    $5K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,040 Sq Ft

    2505 Devon Place Unit 750, Winter Haven, FL 33881

    2 Bed | 2 Bath | 1040 sq ft | $79,900 Four Lakes Golf Club Lot 750 Price reduced from $85,000 to $79,900!Totally turnkey - everything you need - just bring your toothbrush. Experience the perfect blend of comfort, accessibility and resort-style living in this thoughtfully updated home. Offering exceptional value, this residence is ideal for those seeking an easy, low-maintenance lifestyle without

    Cheryl Dobbs CRF Communities

    2505 Devon Place Unit 750, Winter Haven, FL 33881
  • /6

    $277,900

    New Construction
    • 3 Beds
    • 2 Baths
    • 1,447 Sq Ft

    The Newport Plan at Crescent Pointe, Winter Haven, FL 33884

    Southern Homes Builder
    7623 State Highway 653 Hwy Unit 37275805, Winter Haven, FL 33884
  • /30

    $299,900

    New Construction $20K PRICE DROP
    • 5 Beds
    • 2 Baths
    • 1,708 Sq Ft

    2795 Adeline Ave, Winter Haven, FL 33881

    The property is located at 2795 Adeline Ave WINTER HAVEN FL 33881 priced at 299900, the square foot and stories are 1708, 1.The number of bath is 2, halfbath is 0 there are 5 bedrooms and 2 garages. For more details please, call or email.

    D.R. Horton Builder
    2795 Adeline Ave, Winter Haven, FL 33881
  • /36

    $249,000

    $16K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,442 Sq Ft

    2202 Garden Lake Dr, Winter Haven, FL 33884

    Experience resort-style living in the prestigious gated community of Winterset, just minutes from Legoland. This captivating 3-bedroom, 2-bath villa, featuring Mediterranean-inspired architecture, offers the perfect blend of elegance, comfort, and tranquility. Upon arrival, you’re welcomed by a charming covered screened porch accented with a leaded glass entry door, setting the tone for the

    Eileen Belanger CENTURY 21 MYERS REALTY LAKE WALES

    2202 Garden Lake Dr, Winter Haven, FL 33884
  • /28

    $185,000

    $30K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,439 Sq Ft

    2270 Firestone Place, Winter Haven, FL 33884

    Welcome to this spacious and well-maintained villa in Cypresswood Golf & Country Club, offering comfortable living in one of Winter Haven's established gated golf communities. Please note: The professional photos currently showing blue carpet were taken before the recent flooring update. New flooring has now been installed in the living room, dining room, kitchen, hallway, and Florida room.

    Darin Dobson COMPASS FLORIDA LLC

    2270 Firestone Place, Winter Haven, FL 33884
  • /17

    $293,900

    New Construction $9K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,672 Sq Ft

    3740 Giorgio Dr, Winter Haven, FL 33884

    The property is located at 3740 Giorgio Drive WINTER HAVEN FL 33884 priced at 293900, the square foot and stories are 1672, 1.The number of bath is 2, halfbath is 0 there are 3 bedrooms and 2 garages. For more details please, call or email.

    D.R. Horton Builder
    3740 Giorgio Dr, Winter Haven, FL 33884
  • /11

    $59,900

    $13K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 850 Sq Ft

    400 El Camino Dr Unit 223, Winter Haven, FL 33884

    Welcome Home to Orchid Springs Village! Step into comfort with this inviting 1-bedroom, 1.5-bath condo located on the second floor of the peaceful Orchid Springs 55+ community. Surrounded by mature landscaping, this residence offers a quiet and comfortable setting, ideal for those looking to enjoy a relaxed Florida lifestyle. You’ll appreciate being conveniently close to shopping, dining, medical

    Scott Cohara KELLER WILLIAMS CLASSIC

    400 El Camino Dr Unit 223, Winter Haven, FL 33884
  • /39

    $110,000

    • 2 Beds
    • 2 Baths
    • 1,030 Sq Ft

    333 Lake Howard Dr NW Unit 102D, Winter Haven, FL 33880

    FIRST FLOOR BEAUTY! This move-in-ready 2 bedroom 2 bath condo is just what you've been waiting to find. 2025 was a big year with loads of quality updates in each room. The kitchen boasts updated quartz countertops, sparkling glass backsplash, sleek white soft close Shaker cabinets, and various stainless steel appliances. The stack washer/dryer is @1yr, and is tucked in next to the new hot water

    Marti Sutton CENTURY 21 WATSON & MYERS REALTY

    333 Lake Howard Dr NW Unit 102D, Winter Haven, FL 33880
  • /31

    $29,900

    $8K PRICE DROP
    • 2 Beds
    • 1.5 Baths
    • 700 Sq Ft

    674 Century Ln Unit 674, Winter Haven, FL 33881

    2 Bed | 1 1/2 Bath | 700 square foot | $29,900 (Hidden Golf Club- Lot 674) 10K PRICE DROP, motivated seller! Enjoy the Florida lifestyle in this highly sought after 55+ community. This lovely furnished home boasts newer shingle roof (2025), newer flooring and new vanity and toilet in primary bathroom. Large pantry in the kitchen area. You will love the spacious lanai for relaxing and shed for

    Brandi Sappington CRF Communities

    674 Century Ln Unit 674, Winter Haven, FL 33881
  • /23

    $290,000

    $110K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,604 Sq Ft

    29 Golfview Cir NE, Winter Haven, FL 33881

    Short Sale. We are in the process of getting a short sale approved. So expect delays.Welcome to 29 Golfview Circle NE, a beautifully modernized Winter Haven property offering a rare combination of charm, flexibility, and income-producing potential. The main residence features 3 bedrooms and 2 baths with an open, inviting layout that includes spacious living and dining areas, stainless steel

    Chris Sakamoto MARK SPAIN REAL ESTATE

    29 Golfview Cir NE, Winter Haven, FL 33881
  • /8

    $189,000

    • 3 Beds
    • 1 Bath
    • 744 Sq Ft

    345 Avenue P NE Unit FVS, Winter Haven, FL 33881

    Great opportunity to obtain a house at a lower price. The house has new kitchen and new bathroom. No HOA fees. Can be purchase with a low monthly mortgage payment. New AC to be install.

    Ivette Graves RODRIGUEZ PROPERTY MANAGEMENT

    345 Avenue P NE Unit FVS, Winter Haven, FL 33881
  • /27

    $288,900

    New Construction $1K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,593 Sq Ft

    1726 Hummingbird Rd, Winter Haven, FL 33884

    The property is located at 1726 Hummingbird Road WINTER HAVEN FL 33884 priced at 288900, the square foot and stories are 1593, 1.The number of bath is 2, halfbath is 0 there are 3 bedrooms and 2 garages. For more details please, call or email.

    D.R. Horton Builder
    1726 Hummingbird Rd, Winter Haven, FL 33884
  • /27

    $274,990

    • 4 Beds
    • 2 Baths
    • 2,128 Sq Ft

    6004 Kaley Dr, Winter Haven, FL 33880

    Welcome to this well-located single-family home situated in Winter Haven, offering a comfortable layout and enjoyable outdoor space. This home features 4 bedrooms and 2 bathrooms with a practical floor plan that supports everyday living, along with a 2-car garage and a large driveway. The property also includes a newer shingle roof (2023) and newer LVP flooring. Inside, the living area offers two

    Gabriel Andrada FLORIDA SPIRIT HOMES

    6004 Kaley Dr, Winter Haven, FL 33880
  • /2

    $49,000

    $10K PRICE INCREASE
    • Land
    • 1.04 Acres
    • $47,115 per Acre

    0 Gerber Dairy Rd Unit MFRO6269500, Winter Haven, FL 33880

    This 1.04-acre vacant lot on Gerber Dairy Road in Winter Haven, Florida, "Zoning: RC" offers a great opportunity to build your dream spot with space and privacy. Enjoy a peaceful setting while remaining conveniently close to local amenities, schools, and major roads. A perfect property to create your ideal Florida lifestyle.Pin Location: Latitude 27.94515187, Longitude -81.75007994. Note: buyers

    Samih Sadiq KELLY RIGHT REAL ESTATE

    0 Gerber Dairy Rd Unit MFRO6269500, Winter Haven, FL 33880
  • /41

    $67,400

    • 2 Beds
    • 2 Baths
    • 768 Sq Ft

    262 Fairway Cir Unit 262, Winter Haven, FL 33881

    2 Bed | 2 Bath | 768 square foot | $67,400 (Swiss Golf and Tennis- Lot 262) Beautifully landscaped and updated home in a highly sought-after 55+ active golf community! This fully furnished home has so many updates, including a new roof and carport (2024). Gorgeous kitchen with new cabinets and granite counter tops. All new vinyl tilt in windows. Both bathrooms have been updated with new vanities

    Brandi Sappington CRF Communities

    262 Fairway Cir Unit 262, Winter Haven, FL 33881
  • /39

    $280,000

    $20K PRICE DROP
    • 4 Beds
    • 2 Baths

    1536 Axel Cir, Winter Haven, FL 33880

    Welcome to this stunning 4-bedroom, 2-bath home located in the sought-after in Winter Haven! Designed for modern living, featuring a bright open-concept layout that seamlessly connects the living, dining, and kitchen spaces perfect for entertaining and everyday comfort. The kitchen shines with sleek cabinetry, ample counter space, and modern finishes, creating the perfect space to cook and

    Durshan Burke-Troutman Align Right Realty K1 Group

    1536 Axel Cir, Winter Haven, FL 33880
  • /14

    $275,000

    • 3 Beds
    • 2.5 Baths
    • 1,685 Sq Ft

    110 Morning Glory Cir, Winter Haven, FL 33884

    Move-in ready and thoughtfully maintained, this home checks every box a new A/C (2025), newer water heater (2021), and a newer tile roof so you can buy with confidence. Step outside to a private, lushly landscaped backyard garden, the perfect setting for morning coffee or evening unwinding, complemented by a bright, spacious Florida room overlooking tranquil lake views. Set in a highly desirable,

    Christopher Gallon, Pa EXP REALTY LLC

    110 Morning Glory Cir, Winter Haven, FL 33884
  • /43

    $105,000

    $12K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 864 Sq Ft

    4420 Limewood St, Winter Haven, FL 33880

    Welcome home to 4420 Limewood St in Winter Haven, located in the desirable 55+ co-op community of Oakwood Estates—a neighborhood known for active living, friendly neighbors, and resort-style amenities that make every day feel like a vacation.This home has been thoughtfully updated so you can move right in with confidence. One of the biggest improvements is the brand-new architectural shingle

    Chris Loschiavo RE/MAX HERITAGE PROFESSIONALS

    4420 Limewood St, Winter Haven, FL 33880
  • /54

    $65,500

    $4K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,120 Sq Ft

    1056 Eagle Dr Unit 1056, Winter Haven, FL 33881

    2 Bed | 2 Bath | 1120 square foot | $65,500 (Swiss Golf and Tennis- Lot 1056) Price drop! Beautiful turnkey, fully furnished home in a highly sought-after 55+ active golf community! This home has so many updates, including a new roof and carport (2025). Enjoy privacy and tranquility on this corner lot, where every window overlooks open surroundings rather than neighboring homes. Enjoy newer

    Brandi Sappington CRF Communities

    1056 Eagle Dr Unit 1056, Winter Haven, FL 33881
  • /2

    $282,990

    New Construction
    • 3 Beds
    • 2 Baths
    • 1,504 Sq Ft

    4149 Giorgio Dr, Winter Haven, FL 33884

    The property is located at 4149 Giorgio Drive WINTER HAVEN FL 33884 priced at 275490, the square foot and stories are 1504, 1.The number of bath is 2, halfbath is 0 there are 3 bedrooms and 2 garages. For more details please, call or email.

    D.R. Horton Builder
    4149 Giorgio Dr, Winter Haven, FL 33884
  • /35

    $225,000

    • 4 Beds
    • 2.5 Baths
    • 1,839 Sq Ft

    650 Avenue N SE, Winter Haven, FL 33880

    Welcome to this charming and versatile 4-bedroom, 2.5-bath home nestled on a quiet cul-de-sac in sought-after Southeast Winter Haven, offering the perfect combination of comfort, functionality, and thoughtful updates. Inside, you'll find a flexible floor plan featuring TWO SPACIOUS LIVING AREAS plus an additional FLEX SPACE that can easily serve as a home office, playroom, fitness room, or media

    David Small KELLER WILLIAMS REALTY SMART 1

    650 Avenue N SE, Winter Haven, FL 33880
  • /30

    $184,900

    $15K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 1,988 Sq Ft

    440 Midnight Cypress Dr Unit 97, Winter Haven, FL 33881

    Lot #97 / 3 B / 3 BA / 1,988 Sq. Ft. / $199,500.00 Spectacular Home! Completely Remodeled 2009 Erica Model in popular Cypress Creek Village! This large home is located on a spacious corner lot. It has a double carport with extra covered golf cart parking. Professionally remodeled upgrades include: - New Architectural Shingle Roof - New Air Conditioner and New Mr. Cool a/c for the tiled Florida

    Jennifer Meyers CRF Communities

    440 Midnight Cypress Dr Unit 97, Winter Haven, FL 33881
  • /22

    $45,000

    • 2 Beds
    • 2 Baths
    • 672 Sq Ft

    46 Odessa Dr SW, Winter Haven, FL 33880

    Fixer Upper with Split Floor Plan in a 55+ Community - Winter Haven, Florida Homes in Garden Mobile Village, a 55+ community are on lot leased land Winter Haven, Florida. Owning the home, but not the land, you pay a monthly lot rent of $462.00 which gives you and your guest access to the amenities of the community. Water, sewer & trash are included in the lot fee. Also, each home has a boat

    Bette Johnson Renee's Resales

    46 Odessa Dr SW, Winter Haven, FL 33880
  • /29

    $280,900

    New Construction
    • 3 Beds
    • 2 Baths
    • 1,504 Sq Ft

    4081 Giorgio Dr, Winter Haven, FL 33884

    The property is located at 4081 Giorgio Drive WINTER HAVEN FL 33884 priced at 280900, the square foot and stories are 1504, 1.The number of bath is 2, halfbath is 0 there are 3 bedrooms and 2 garages. For more details please, call or email.

    D.R. Horton Builder
    4081 Giorgio Dr, Winter Haven, FL 33884
  • /54

    $234,900

    $5K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,728 Sq Ft

    509 Sharon Hill Ct, Winter Haven, FL 33880

    USDA financing may be available for qualified buyers, potentially allowing 100% financing with no down payment. Buyers should verify eligibility with their lender. Welcome to your slice of country living with room to breathe! Situated on approximately 0.65 acres, this well-maintained 3-bedroom, 2-bath home offers the perfect blend of privacy, functionality, and convenience. Step inside to find

    Robert Miller MILLSHIRE REALTY

    509 Sharon Hill Ct, Winter Haven, FL 33880
  • /2

    $169,000

    $10K PRICE DROP
    • Land
    • 10,890 Sq Ft
    • $676,000 per Acre

    709 Lake Shipp Dr, Winter Haven, FL 33880

    Please note: Price reduction. Curt Campbell is my brother and I represent his interest in this Transaction. This property features access to the Winter Haven Chain of Lakes and there is NO HOA.

    Jim Campbell CENTURY 21 MYERS REALTY

    709 Lake Shipp Dr, Winter Haven, FL 33880

Showing Results 361 - 400, Page 10 of 18

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