849

Winter Haven, FL Homes for Sale with Pool

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  • /26

    $247,500

    • 3 Beds
    • 3 Baths
    • 2,070 Sq Ft

    35 Enclave Dr, Winter Haven, FL 33884

    NEW PRICE ON THIS SPACIOUS 3 BEDROOM ENCLAVE UNIT IN CYPRESSWOOD!!! VILLA WITH OVER 2,000 PLUS SQ. FT. LIVING 3 BEDROOM 3 BATH PLAN! YOU WILL ENJOY A TRUE FLORIDA LIFESTYLE WITH THE AMENITIES AT CYPRESSWOOD GOLF & COUNTRY CLUB!! This maintenance-free villa is pristine, the largest villa floor plan in the Cypresswood Enclave with over 2,000 sq. ft. of living area designed with an open floor plan,

    Catherine Kluytenaar THE K TEAM REAL ESTATE SERVICES LLC

    35 Enclave Dr, Winter Haven, FL 33884
  • /51

    $230,000

    • 2 Beds
    • 2 Baths
    • 1,078 Sq Ft

    715 Magnolia Place, Winter Haven, FL 33884

    Experience beautiful waterfront views, nightly sunsets, and direct access to the world-famous Winter Haven Chain of Lakes in this updated lakefront condo located in the gated community of Winterset. Offering 2 bedrooms, 2 bathrooms, and a private one-car garage, this second-floor residence blends comfort, style, and the relaxed Florida lakefront lifestyle.Inside, an open and airy floorplan

    Michael Stone THE STONES REAL ESTATE FIRM

    715 Magnolia Place, Winter Haven, FL 33884
  • /20

    $175,000

    • 2 Beds
    • 2 Baths
    • 1,040 Sq Ft

    6320 Grove Pointe Dr SE, Winter Haven, FL 33884

    Welcome to the inviting 55+ community of Garden Grove Oaks in Winter Haven, FL. This charming manufactured home offers comfortable living in a peaceful, amenity-rich neighborhood perfect for active adults. Inside, you’ll find a bright, open layout with a spacious living area ideal for relaxing or hosting company. Brand-new flooring has just been installed, giving the home a fresh, updated feel.

    Don Jerue KELLER WILLIAMS REALTY SMART 1

    6320 Grove Pointe Dr SE, Winter Haven, FL 33884
  • /38

    $159,900

    • 2 Beds
    • 2 Baths
    • 1,822 Sq Ft

    1125 La Costa Ln Unit 636, Winter Haven, FL 33881

    2 Bedrooms + Den | 2 Bathrooms | 1,822 Sq. Ft. | $159,900 Lot 636 | 1125 La Costa Elegant and Inviting Florida Retreat Step into the warmth and charm of this beautifully maintained home in the sought-after Four Lakes Golf Club community - where comfort meets sophistication and every detail has been lovingly cared for. The moment you enter, you're greeted by a bright and welcoming living room that

    Cheryl Dobbs CRF Communities

    1125 La Costa Ln Unit 636, Winter Haven, FL 33881
  • /32

    $47,500

    • 2 Beds
    • 2 Baths
    • 1,016 Sq Ft

    134 Mandarin Dr SE, Winter Haven, FL 33884

    Spacious Home with Bonus Living Spaces and Community Pool Access Homes in the Orange Manor East, a 55+ lake community, are on lot leased land in Winter Haven, Florida. Owning the home, but not the land, you pay a monthly lot rent of $530 which gives you and your guest access to the amenities of the community. Welcome to this charming and versatile 36' x 24' doublewide manufactured home, offering

    Bette Johnson Renee's Resales

    134 Mandarin Dr SE, Winter Haven, FL 33884
  • /10

    $124,900

    • 2 Beds
    • 1.5 Baths
    • 1,050 Sq Ft

    689 Lake Howard Dr NW Unit 1E, Winter Haven, FL 33880

    Beautiful property located in a remarkable location! Do not miss out on the opportunity of making this property yours. Discover the perfect blend of comfort and convenience in this beautiful Winter Haven property. Nestled in a peaceful neighborhood, this property offers spacious living areas and a welcoming atmosphere. Enjoy bright living, a well-appointed kitchen, and generously sized bedrooms.

    Maria Rivera RIVERA & ASSOCIATES REALTY

    689 Lake Howard Dr NW Unit 1E, Winter Haven, FL 33880
  • /54

    $355,000

    • 2 Beds
    • 2 Baths
    • 1,677 Sq Ft

    5197 Pebble Beach Blvd, Winter Haven, FL 33884

    Don't miss out on this opportunity to reside in a home located on the WEST golf course in Lake Ashton. This home is being sold FURNISHED; GOLF CART INCLUDED and WASHER/DRYER INCLUDED! This Callaway Floor plan with NEW A/C (December 2025) is a "Green" home with 2 Bedrooms, 2 Baths, Plus Office with over 1,660 sq. ft. of living space. Located on the 17th Fairway of the West Golf Course in Lake

    Lori Raath LAKE ASHTON REALTY INC.

    5197 Pebble Beach Blvd, Winter Haven, FL 33884
  • /48

    $349,900

    • 3 Beds
    • 2 Baths
    • 1,717 Sq Ft

    2220 Garden Lake Dr, Winter Haven, FL 33884

    Nestled behind the gates of Winterset, one of Winter Haven’s most sought-after lakefront communities, this meticulously maintained 3-bedroom, 2-bath home offers stunning water views and a serene natural setting surrounded by ponds and towering cypress trees. With water wrapping around the east and south sides, every day brings a new display of Florida wildlife, from graceful herons to playful

    Deanna Stone THE STONES REAL ESTATE FIRM

    2220 Garden Lake Dr, Winter Haven, FL 33884
  • /2

    $280,000 New Construction

    • 4 Beds
    • 7 Baths
    • 1,824 Sq Ft

    2228 Chris Dr, Winter Haven, FL 33884

    BEAUTIFUL home built in 2024 with 1,824 square feet on one story, featuring 3 bedrooms, 2 baths, and an open living area.The kitchen boasts an open and airy design, with a spacious center island perfect for entertaining, complemented by new stainless-steel appliances,and a walk-in pantry.The dining room is perfectly placed near the kitchen, providing the ideal setting for meals and

    Marian Capri Capriles Garcia LPT REALTY, LLC

    2228 Chris Dr, Winter Haven, FL 33884
  • /5

    $329,366 New Construction

    • 4 Beds
    • 3 Baths
    • 2,200 Sq Ft

    1533 Leamington Ln, Winter Haven, FL 33884

    Under Construction. Step into a home that instantly wraps you in warmth and possibility. Bathed in natural light from an impressive double window, this radiant space is more than just a room — it's a blank canvas ready for your next chapter.Imagine a serene home office, a play zone, an inspiring craft studio, or a cozy library nook — this flexible space effortlessly adapts to your lifestyle.

    Claudia Gutierrez ADAMS HOMES REALTY

    1533 Leamington Ln, Winter Haven, FL 33884
  • /56

    $470,000

    • 4 Beds
    • 3 Baths
    • 2,438 Sq Ft

    319 Terranova Blvd, Winter Haven, FL 33884

    Step into this elegant residence nestled within a serene gated community, where comfort meets sophistication. This home offers 4 spacious bedrooms and 3 full bathrooms, beautifully designed with thoughtful upgrades and stylish finishes throughout. Bask in the Florida sunshine by your sparkling screened-in pool—an inviting retreat for relaxation or entertaining. Perfectly positioned near Winter

    Laura Pizarro PIZARROS GROUP

    319 Terranova Blvd, Winter Haven, FL 33884
  • /18

    $309,990 New Construction

    • 5 Beds
    • 2.5 Baths
    • 2,112 Sq Ft

    Edison Plan at VillaMar, Winter Haven, FL 33884

    The first floor of this new two-story home is host to an open-concept layout that combines the kitchen with the living and dining areas, and an outdoor patio is easily reached off the main living space. Upstairs, five bedrooms surround a versatile loft, including the luxe owner’s suite, complete with a generous walk-in closet and en-suite bathroom.

    Lennar Builder
    6614 Crescent Loop Unit 38667750, Winter Haven, FL 33884
  • /13

    $314,390 New Construction

    • 4 Beds
    • 3 Baths
    • 1,988 Sq Ft

    3873 Giorgio Dr, Winter Haven, FL 33884

    Open floor plan creates a unified living space with a large great room that overlooks the kitchen.

    Meritage Homes Builder
    3873 Giorgio Dr, Winter Haven, FL 33884
  • /45

    $14,900

    • 2 Beds
    • 1 Bath

    54 Dale Dr, Winter Haven, FL 33880

    Discover your new home at 54 Dale Dr in Winter Haven, FL! This 2-bedroom, 1-bathroom house is now on the market and ready for its next owner. Nestled in a peaceful, wooded neighborhood, this property offers the perfect blend of small-town living with big-city convenience. Recently updated with brand new flooring, this home will be move-in ready when you arrive. It's part of the Winter Haven MHC,

    Chrissy Walter Sunset Home Sales

    54 Dale Dr, Winter Haven, FL 33880
  • /64

    $19,990

    • 1 Bed
    • 1 Bath

    225 Mockingbird Ln, Winter Haven, FL 33884

    Discover your perfect retreat in this charming one-bedroom, one-bathroom home nestled in the vibrant Lake Deer community. This must-see property awaits your personal touch. Step into a world where relaxation meets recreation. The expansive clubhouse buzzes with engaging activities and friendly neighbors who know how to have a good time. Stay fit with convenient on-site fitness equipment, or soak

    Chrissy Walter Sunset Home Sales

    225 Mockingbird Ln, Winter Haven, FL 33884
  • /13

    $272,670 New Construction

    • 3 Beds
    • 2 Baths
    • 1,483 Sq Ft

    3889 Giorgio Dr, Winter Haven, FL 33884

    Retreat to your primary suite located in the back of the home for plenty of privacy and offers a huge walk-in closet.

    Meritage Homes Builder
    3889 Giorgio Dr, Winter Haven, FL 33884
  • /52

    $169,900

    • 2 Beds
    • 2 Baths
    • 1,248 Sq Ft

    6044 Grand Oaks Dr SE, Winter Haven, FL 33884

    Welcome to 6044 Grand Oaks Dr SE in Winter Haven, a beautifully updated waterfront home in the desirable 55+ community of Garden Grove Oaks, where you OWN THE LAND! Enjoy peaceful water views right from your backyard and take advantage of a recent $15,000 price improvement, making this home an incredible value. This charming 2-bedroom, 2-bath residence offers the perfect blend of comfort, modern

    Patricia de Graaff RE/MAX HERITAGE PROFESSIONALS

    6044 Grand Oaks Dr SE, Winter Haven, FL 33884
  • /16

    $306,950 New Construction

    • 3 Beds
    • 2 Baths
    • 1,700 Sq Ft

    5351 Mickey Ave, Lake Wales, FL 33859

    **Take advantage of special financing + Flex Funds on quick move-in homes** THIS HOME OFFERS, 9"4' CEILINGS AND 8' DOORS, 42' CABINETS, WHITE QUARTZ COUNTER TOPS IN KITCHEN, CERAMIC TILE THROUGHOUT THE WET AND MAIN LIVING AREAS OF THE HOME, ALL BEDROOMS, FAMILY ROOM, AND COVERED LANAI ARE PREWIRED FOR CEILING FANS. *Options may vary by community, so see your sales associate for details. These

    Stephanie Morales THE REALTY EXPERIENCE POWERED BY LRR

    5351 Mickey Ave, Lake Wales, FL 33859
  • /22

    $95,000

    • 2 Beds
    • 2 Baths
    • 1,456 Sq Ft

    214 Green Meadow Dr, Winter Haven, FL 33884

    Live the lifestyle you’ve been waiting for in this beautifully updated 2-bedroom, 2-bath mobile home that comes with one share of Orange Manor West Co Op, This home is nestled within a gated, active 55+ community. Step inside to a modern, refreshed interior that’s both stylish and easy to maintain. Spend your days soaking up the sun by the resort-style pool, enjoying friendly competition on the

    Darlene Bice BHHS FLORIDA PROPERTIES GROUP

    214 Green Meadow Dr, Winter Haven, FL 33884
  • /57

    $79,900

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

    281 Putter Cir, Winter Haven, FL 33881

    Beautifully updated and move-in ready home in a highly sought-after 55+ active golf community! This spacious open-layout home offers comfort, style, and plenty of room to relax or entertain. Partially furnished and loaded with upgrades, including a new roof and double carport (2023), AC (2021), new gutter guards, hurricane tie-downs, and side door. Features two living areas, a large kitchen with

    Brandi Sappington CRF Communities

    281 Putter Cir, Winter Haven, FL 33881
  • /50

    $124,000

    • 2 Beds
    • 2 Baths
    • 1,364 Sq Ft

    4119 Rolling Oaks Dr, Winter Haven, FL 33880

    A "FIVE STAR" GATED, RESIDENT OWNED COMMUNITY IN WINTER HAVEN, FLORIDA! Own your lot with this spacious two bedroom two bath manufactured home, which offers the finest in carefree living in this 55+ community. It boasts a fabulous floor plan that features a freshly painted kitchen with new kitchen cabinets, new hardware, new backsplash, new countertops, new sink, new faucet and updated

    Becky Blake CHARLES RUTENBERG REALTY ORLANDO

    4119 Rolling Oaks Dr, Winter Haven, FL 33880
  • /39

    $285,000

    • 2 Beds
    • 2 Baths
    • 1,295 Sq Ft

    3365 Raleigh Dr, Winter Haven, FL 33884

    Welcome to Traditions at Lake Ruby — a vibrant 55+ lakeside community where every day feels like a Florida resort getaway. Welcome to this lovely 2-bedroom, 2-bathroom home in the highly sought-after Traditions at Lake Ruby community!Walk through the front door into an open-concept living and dining area that flows seamlessly into the kitchen. With bright windows and quality finishes, the

    James Barris EXP REALTY LLC

    3365 Raleigh Dr, Winter Haven, FL 33884
  • /5

    $338,967 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,405 Sq Ft

    2331 Brassie Ct, Winter Haven, FL 33884

    Under Construction. This two-story home features 4 bedrooms and 2 and a half baths. This Home begins with a two-story foyer opening up to the spacious first floor living spaces. The kitchen shines with abundant counter space and an island perfect for entertaining, Upstairs, you will find all four bedrooms. CUSTOM EXTERIOR includes 30-year mildew resistant dimensional shingles Cementitious masonry

    Claudia Gutierrez ADAMS HOMES REALTY

    2331 Brassie Ct, Winter Haven, FL 33884
  • /29

    $315,000 Open House 1/03

    • 4 Beds
    • 2 Baths
    • 1,707 Sq Ft

    1228 Denali Dr, Winter Haven, FL 33881

    Better Than New 4 Bedroom Home, universal design features, No CDD, flexible floor plan, & Move-In Ready! This thoughtfully designed 4 bedroom, 2 bath home embraces the principles of universal design creating a comfortable, accessible, and intuitive living experience for people of all ages and abilities. You'll enjoy wide 36” interior doorways, no steps in or out of the home, and an open flowing

    Jackie Mazurowski KELLER WILLIAMS REALTY SMART 1

    1228 Denali Dr, Winter Haven, FL 33881
  • /70

    $144,990

    • 2 Beds
    • 2 Baths
    • 1,560 Sq Ft

    5330 Laurel Oak Dr, Winter Haven, FL 33880

    Discover this exceptional 2018 manufactured home nestled on a prime cul-de-sac location at 5330 Laurel Oak Drive in Winter Haven Oaks community. Offered mostly furnished for your convenience, this residence provides immediate move-in ready comfort. This thoughtfully designed two-bedroom, two-bathroom home offers the perfect blend of comfort and convenience for discerning homeowners seeking an

    Chrissy Walter Sunset Home Sales

    5330 Laurel Oak Dr, Winter Haven, FL 33880
  • /45

    $105,000

    • 2 Beds
    • 2 Baths
    • 1,184 Sq Ft

    1209 Cypress Vine Rd Unit 295, Winter Haven, FL 33881

    WELCOME to Your Stunning DREAM HOME...with Motivated Seller! Welcome to CYPRESS CREEK VILLAGE, one of Central Florida's NEWEST 55+ active ADULT, PET-FRIENDLY communities, where lifestyle comes first. Located in WINTER HAVEN, this land-LEASE community allows you to own your home while paying an approximate MONTHLY LOT RENT of $724, which includes full access to RESORT-STYLE amenities for you and

    Tammy Barnhart Renee's Resales

    1209 Cypress Vine Rd Unit 295, Winter Haven, FL 33881
  • /38

    $36,900

    • 2 Beds
    • 1.5 Baths
    • 756 Sq Ft

    595 Century Dr, Winter Haven, FL 33881

    Priced to Sell in Hidden Golf - A Highly Sought-After 55+ Gated Community! Own your slice of paradise in the desirable, gated 55+ community of Hidden Golf! This lovely, affordable 2-bedroom, 1.5-bath home is ideal for those seeking the best of Florida living. The large carport with LANAI located behind for relaxation and an attached shed for extra storage, greets you upon entering the property.

    Cynthia Cole Sunset Home Sales

    595 Century Dr, Winter Haven, FL 33881
  • /17

    $367,990 New Construction

    • 4 Beds
    • 3 Baths
    • 2,631 Sq Ft

    Primrose Plan at VillaMar - Signature Series, Winter Haven, FL 33884

    Entertain guests with ease with an open kitchen which overlooks the dining and great room. First floor flex space can be best used to fit your family's needs. Upstairs primary suite features an oversized walk-in closet.

    Meritage Homes Builder
    3745 Giorgio Dr Unit 37076789, Winter Haven, FL 33884
  • /59

    $150,000

    • 2 Beds
    • 2 Baths

    353 Siberian Cypress Cir, Winter Haven, FL 33881

    Welcome home to this impeccable 2-bedroom 2-bath sanctuary awaiting your arrival! This STUNNING 2023-built residence is nestled in one of Winter Haven's most sought-after 55+ communities, Cypress Creek Village. **LOW LOT LEASE $660** and Close to all! With Palm trees lining the streets, this lovely community offers resort-style living at its finest. FULLY FURNISHED with well-appointed features,

    Linda Wilson Sunset Home Sales

    353 Siberian Cypress Cir, Winter Haven, FL 33881
  • /63

    $129,900

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

    5 Marina Dr, Winter Haven, FL 33881

    Fully renovated lakefront home located directly on beautiful Lake Henry in a highly desirable 55+ community. This home offers stunning lake views from all main living areas and exceptional indoor-outdoor living. Completely updated to include a brand-new roof, brand new AC system, and brand-new siding. Features include a spacious lanai with double sliding doors overlooking the lake, dedicated

    Brandi Sappington CRF Communities

    5 Marina Dr, Winter Haven, FL 33881
  • /19

    $349,950 New Construction

    • 4 Beds
    • 3 Baths
    • 2,077 Sq Ft

    5355 Mickey Ave, Lake Wales, FL 33859

    *Take advantage of special financing + Flex Funds on quick move-in homes* This home offers, 9"4' ceilings and 8' doors, 42' cabinets, white quartz counter tops in kitchen, ceramic tile throughout the wet and main living areas of the home, all bedrooms, family room, and covered lanai are prewired for ceiling fans, secondary bedroom with its own bathroom. Seasons at Annabelle Estates is a must-see

    Stephanie Morales THE REALTY EXPERIENCE POWERED BY LRR

    5355 Mickey Ave, Lake Wales, FL 33859
  • 3111 Laurel Oak Ln, Winter Haven, FL 33884

    $334,700 New Construction

    • 4 Beds
    • 2 Baths
    • 1,857 Sq Ft

    3111 Laurel Oak Ln, Winter Haven, FL 33884

    Move-in ready 4-bedroom home for sale in Winter Haven, Florida! This home features a spacious, open living area, a luxuriously appointed kitchen, and outdoor living space with a covered lanai and craftsman-style front porch! Enjoy privacy and relaxation in your spacious owner's suite complete with a large walk-in wardrobe and en-suite bath including a large tiled shower, dual vanities, a closeted

    Highland Homes Builder
    3111 Laurel Oak Ln, Winter Haven, FL 33884
  • /35

    $315,000

    • 3 Beds
    • 2 Baths
    • 1,553 Sq Ft

    3307 Costello Cir, Winter Haven, FL 33884

    The original owner upgraded this property with a fenced in yard. In addition, all carpeting has been replaced in the bedrooms to vinyl flooring. A water softener/filtration system was installed to service the entire house. Luxury wood vinyl plank flooring is in living area, laundry room and baths. Despite this property being new construction two years ago, all rooms were painted to add to the

    Shirley Fitzsimmons UNITED REAL ESTATE PREFERRED

    3307 Costello Cir, Winter Haven, FL 33884
  • /2

    $311,990 New Construction

    • 4 Beds
    • 2 Baths
    • 1,562 Sq Ft

    2775 San Marco Way, Winter Haven, FL 33884

    This well-planned single-story home offers 4 bedrooms, 2 bathrooms, and approximately 2,100 square feet of living space with a 2-car garage. The open-concept layout features a spacious great room that flows seamlessly into the dining area and kitchen, creating an inviting space for everyday living and entertaining. The kitchen includes a center island, pantry, and ample counter space, with clear

    Maronda Homes Builder
    2775 San Marco Way, Winter Haven, FL 33884
  • /74

    $34,900

    • 2 Beds
    • 2 Baths
    • 896 Sq Ft

    62 Dale Dr, Winter Haven, FL 33880

    Whether you're looking to downsize, retire, or simply embrace the best of Florida's lifestyle, this 2 bedroom|2 bathroom in Winter Haven is the perfect place to make your dreams a reality. Winter Haven MHC is a 55+ pet-friendly community for active seniors. There is plenty of additional living space to entertain family/friends and/or enjoy the Florida weather in the large air conditioned lanai,

    Patti Alvin Sunset Home Sales

    62 Dale Dr, Winter Haven, FL 33880
  • /46

    $37,900

    • 2 Beds
    • 2 Baths
    • 924 Sq Ft

    445 Dolphin Dr, Winter Haven, FL 33881

    Hidden Cove West/ Lot #445 / 2 Bedroom/2 Bath / 924 Sq. Ft. / $37,900.00 This amazing home is at an incredible price and a great floor plan with plenty of square footage! It offers the buyer: Roof (2 years old) A/C (2 years old) New Awnings New Front Door New Underpinning Updated Luxury Vinyl Plank Flooring Updated Bathrooms Split Floor Plan Newer Windows Sprinkler System Large Master

    Jennifer Torres CRF Communities

    445 Dolphin Dr, Winter Haven, FL 33881
  • /32

    $119,000

    • 3 Beds
    • 2 Baths
    • 1,226 Sq Ft

    333 Lake Howard Dr NW Unit 204D, Winter Haven, FL 33880

    Welcome to 333 Lake Howard Drive, where comfort, convenience, and a vibrant 55+ lifestyle come together in the heart of Winter Haven’s charming lakefront community. Nestled within the desirable Imperial Harbours 55+ community, this spacious and sunlit 3-bedroom, 2-bathroom corner-unit condo that oversees the pool offers the ideal space for those seeking a relaxed, maintenance-free lifestyle. From

    Jason Prieto LPT REALTY, LLC

    333 Lake Howard Dr NW Unit 204D, Winter Haven, FL 33880
  • /4

    $297,900 New Construction

    • 4 Beds
    • 2 Baths
    • 1,754 Sq Ft

    3119 Laurel Oak Ln, Winter Haven, FL 33884

    Move-in ready 4-bedroom home for sale in Winter Haven, Florida! The Paisley features a Craftsman-style exterior and a fully open living area that includes a spacious gathering room, an open kitchen with a counter-height bar and walk-in pantry, and a sunny dining cafe, all under an airy volume ceiling. Unwind in your private owner's suite complete with a large walk-in wardrobe with linen shelves

    Highland Homes Builder
    3119 Laurel Oak Ln, Winter Haven, FL 33884
  • /24

    $350,900 New Construction

    • 4 - 5 Beds
    • 3.5 Baths
    • 2,587 Sq Ft

    Wesley II Plan at VillaMar - Highland Homes at VillaMar, Winter Haven, FL 33884

    Welcome home to the Wesley II by Highland Homes, a two-story Florida home that lives large with an open living area on the first story and a flexible second-story layout! Downstairs, enjoy a fully open living area with: A large gathering room. An open kitchen with a counter-height buttery island or optional galley island, a walk-in pantry, and a sunny dining cafe. A convenient powder room. An

    Highland Homes Builder
    521 Vittorio Dr Unit 37316138, Winter Haven, FL 33884

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