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Winter Haven, FL Homes for Sale with Pool

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  • /56

    $208,000

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

    492 Lakeside Ranch Cir, Winter Haven, FL 33881

    PRICE IMPROVEMENT!! LAKEFRONT LIVING...Why pay lot rent when you can enjoy the charm and tranquility in this beautifully renovated, Fully Furnished 2 Bedroom/2 Bath 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 Windows both replaced in

    Cheryl Brewer COLDWELL BANKER REALTY

    492 Lakeside Ranch Cir, Winter Haven, FL 33881
  • /37

    Price To Be Determined New Construction

    • 3 Beds
    • 2 Baths
    • 1,672 Sq Ft

    ARIA Plan at Annabelle Estates, Lake Wales, FL 33859

    The Aria is one of our one-story floorplans featured in Annabelle Estates in Lake Wales, Florida. With two exteriors to choose from, the Aria is a popular home. Inside this 3-bedroom, 2-bathroom home, you’ll find 1,672 square feet of comfortable living. This all-concrete block constructed, one-story layout optimizes living space with an open concept kitchen overlooking the living area, dining

    D.R. Horton Builder
    4019 Penelope Ave Unit 36202722, Lake Wales, FL 33859
  • /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
  • /79

    $643,000

    • 3 Beds
    • 4 Baths
    • 3,051 Sq Ft

    4310 Shadow Wood Trail, Winter Haven, FL 33880

    The owners remodeled their dream home, then took a promotion to a new city... their loss is your gain. Located just a few miles from the Polk Parkway and convenient to both Lakeland and Winter Haven, this spacious, newly remodeled home boasts an open floor plan that is perfect for a modern lifestyle. Step into an entryway that overlooks a large dining room, a beautifully updated eat-in kitchen,

    MaryAnn Bartlett NEX REALTY

    4310 Shadow Wood Trail, Winter Haven, FL 33880
  • /37

    $379,999

    • 3 Beds
    • 2.5 Baths
    • 1,926 Sq Ft

    502 Little Lake Ct, Winter Haven, FL 33884

    502 Little Lake Court, Winter Haven, FL 33884 — Your Resort-Style, Lake-Lifestyle Dream Home Awaits Imagine waking up each morning to a serene lake view and having direct access to the world-famous Winter Haven Chain of Lakes just steps from your front door. Welcome to 502 Little Lake Court, a remodeled pool home that blends luxury, comfort, and true Florida living. Located in the highly

    James Barris EXP REALTY LLC

    502 Little Lake Ct, Winter Haven, FL 33884
  • /29

    $275,490 New Construction

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

    4157 Giorgio Dr, Winter Haven, FL 33884

    The property is located at 4157 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
    4157 Giorgio Dr, Winter Haven, FL 33884
  • /23

    $115,000

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

    2605 Ashburn Place Unit 760, Winter Haven, FL 33881

    PRICE REDUCED $15,000 - COME VIEW AND MAKE OFFERS!!! Well-maintained, 3-bedroom/2-bath, 2001 Homes of Merit home located in the wonderful 55+ Four Lakes Golf Club Community. Priced at $115,000. Move-in Ready, two bedrooms fully furnished: 3rd bedroom currently used as an office. All other current furnishings & kitchen items included with purchase. Home roof replaced Sept 2018, NEW Lanai roof Jan

    Deb Bartholomew Sunset Home Sales

    2605 Ashburn Place Unit 760, Winter Haven, FL 33881
  • /45

    $47,900

    • 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. / $47,900.00 This home is located in the beautiful Hidden Cove East community, and is unusually hard to get into! 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 System Luxury Vinyl Plank Flooring 4" Blinds

    Jennifer Torres CRF Communities

    564 Chickasaw Loop Unit 34, Winter Haven, FL 33881
  • /32

    $330,490 New Construction

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

    4415 Blackwell Ave, Lake Wales, FL 33859

    The property is located at 4415 Blackwell Avenue LAKE WALES FL 33859 priced at 330490, the square foot and stories are 2077, 1.The number of bath is 3, halfbath is 0 there are 5 bedrooms and 2 garages. For more details please, call or email.

    D.R. Horton Builder
    4415 Blackwell Ave, Lake Wales, FL 33859
  • /33

    $119,900

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

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

    1315 Las Brisas Lane - Lot 611 2 Bedroom + Den | 2 Bath | 1,439 Sq Ft | $119,900 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
  • /17

    $189,500

    • 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
  • 807 Andrew St, Winter Haven, FL 33881

    $357,490 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
  • /16

    $275,000

    • 3 Beds
    • 2 Baths
    • 1,750 Sq Ft

    3643 Julius Estates Blvd, Winter Haven, FL 33881

    Move-in ready! This home in Lake Smart Estates offers value, comfort, and practical upgrades. Inside, you’ll find an open floor plan with plenty of natural light and modern finishes. The kitchen features 42-inch cabinetry, brand-new appliances, a double osmosis water filtration system, and a breakfast area that connects easily to the main living space. Recent improvements include a new roof, new

    Stacey Vazquez KELLER WILLIAMS REALTY AT THE LAKES

    3643 Julius Estates Blvd, Winter Haven, FL 33881
  • /37

    $179,000

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

    332 Siberian Cypress Cir, Winter Haven, FL 33881

    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 the luxury of a large master bedroom complete with His and Her

    Mary Sergent USA Mobile & Manufactured Home Sales, LLC.

    332 Siberian Cypress Cir, Winter Haven, FL 33881
  • /9

    $275,900 New Construction

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

    5117 Sylas Jax Ave, Winter Haven, FL 33884

    Move-in ready, open layout, 2-story home for sale in Winter Haven, Florida, with 3 bedrooms plus a loft! Downstairs, you'll enjoy a desirable open living area with luxury vinyl plank flooring. Upstairs, you'll find privacy in your owner's suite complete with an en-suite bath with dual vanities, a decorative tiled shower with glass enclosure, a closeted toilet, and a walk-in wardrobe. Two spacious

    Highland Homes Builder
    5117 Sylas Jax Ave, Winter Haven, FL 33884
  • /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
  • /43

    $130,000

    • 2 Beds
    • 2 Baths
    • 1,316 Sq Ft

    103 Lake Hazel Dr, 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

    103 Lake Hazel Dr, Winter Haven, FL 33884
  • /71

    $715,000

    • 4 Beds
    • 3 Baths
    • 2,591 Sq Ft

    105 Wyndham Dr, Winter Haven, FL 33884

    One or more photo(s) has been virtually staged. Discover luxury living in Wyndham at Lake Winterset, one of Winter Haven’s most prestigious gated and guarded lakefront communities. Welcome to 105 Wyndham Drive, an elegant waterfront residence on a sprawling 0.80-acre lot with peaceful pond views, mature landscaping, and timeless architectural appeal. Stately wrought-iron gates, a brick-paved

    Michael Stone THE STONES REAL ESTATE FIRM

    105 Wyndham Dr, Winter Haven, FL 33884
  • /82

    $99,900

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

    355 Putter Cir Unit 355, Winter Haven, FL 33881

    PRICE DROP...MOTIVATED SELLER! This beautifully well maintained one owner 2-bedroom 2-bath home features lots of extras! Highlights of this home are: Newer AC (2021) - Newer appliances (2021) - Updated kitchen and baths - New Florida room windows (2022) - California walk in closets - Large spacious shed that can accommodate the golf cart that is included! The master bath has a modern walk-in

    Brandi Sappington CRF Communities

    355 Putter Cir Unit 355, Winter Haven, FL 33881
  • /17

    $327,728 New Construction

    • 4 Beds
    • 2 Baths
    • 1,919 Sq Ft

    5183 Kinsley Dr, Lake Wales, FL 33859

    **Take advantage of special financing + Flex Funds on quick move-in homes** This beautiful Ruby floorplan boasts an upgraded "C" elevation with laytite stone and 8' exterior doorway. The kitchen is highlighted with preeminent quartz countertops, upgraded 42" cabinets, and a stainless GE dishwasher, microwave, and stovetop. Contemporary 7"x22" wood grain tile adorns the entry way, great room,

    Stephanie Morales THE REALTY EXPERIENCE POWERED BY LRR

    5183 Kinsley Dr, Lake Wales, FL 33859
  • /25

    $255,490 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,673 Sq Ft

    2717 Gladiola Rd, Winter Haven, FL 33884

    Under Construction. This beautiful and spacious townhome is currently under construction and built entirely in concrete blockacross both stories, offering durability and peace of mind. Featuring 3 bedrooms, 2.5 bathrooms, and anupstairs laundry room, the layout is thoughtfully designed for modern living. Luxury vinyl flooring enhancesthe common areas, while plush carpeting adds

    Paul King DR HORTON REALTY OF CENTRAL FLORIDA LLC

    2717 Gladiola Rd, Winter Haven, FL 33884
  • /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
  • 2815 Adeline Ave Unit 38507577, Winter Haven, FL 33881

    $321,990 New Construction

    • 5 Beds
    • 2 Baths
    • 1,708 Sq Ft

    DUNDEE Plan at Willowbrook South, Winter Haven, FL 33881

    Welcome to the Dundee, one of our one-story floorplans available in the beautiful community of Willowbrook South in Winter Haven, Florida. Choose between three thoughtfully designed exterior styles. This spacious 5-bedroom, 2-bathroom home offers 1,708 square feet of modern, comfortable living. Step inside to an inviting open-concept layout where the kitchen, living, and dining areas flow

    D.R. Horton Builder
    2815 Adeline Ave Unit 38507577, Winter Haven, FL 33881
  • /13

    $273,990 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
  • /19

    $99,900

    • 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
  • /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
  • /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!!! 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 & Countertops in Kitchen/Bathroom, Freshly

    Jennifer Torres CRF Communities

    277 Alpine Dr Unit 277, Winter Haven, FL 33881
  • /17

    $249,900

    • 2 Beds
    • 2 Baths
    • 1,438 Sq Ft

    3830 Osprey Pointe Cir, Winter Haven, FL 33884

    Beautiful community of Osprey Pointe on Lake Ned. This 2 bedroom/2 bath home is move in ready. Kitchen with stainless steel appliances, granite counter tops, tile flooring, dinette area. The open floor plan is great for entertaining complete with a large screened in porch and extended paver patio area. No rear neighbors. Living room has newer laminate flooring, master bath has ceramic tile, dual

    Jonathan Minerick HOMECOIN.COM

    3830 Osprey Pointe Cir, Winter Haven, FL 33884
  • /26

    $22,000

    • 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
  • /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
  • /18

    $308,990 New Construction

    • 4 Beds
    • 2.5 Baths
    • 1,880 Sq Ft

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

    This expansive two-story home boasts a well-designed layout, featuring a first floor dedicated to shared living and entertaining. The open concept design seamlessly connects the kitchen, dining room and family room, with a patio extending the interior space outdoors. Upstairs, a spacious loft separates the three secondary bedrooms from the serene owner's suite. Completing the home is a convenient

    Lennar Builder
    1108 Tyler Loop Unit 36037861, Winter Haven, FL 33884
  • /56

    $519,000

    • 4 Beds
    • 3.5 Baths
    • 3,377 Sq Ft

    824 Lake Elbert Ct, Winter Haven, FL 33881

    Welcome to 824 Lake Elbert Ct, a beautifully updated 4 bedroom, 3.5 bathroom pool home offering over 3,300 sq. ft. of living space near Lake Elbert. This spacious two-story home is designed for both everyday living and entertaining, with multiple areas to gather and relax. The main level features a formal living room, formal dining room, a bright breakfast nook, and a large family room that can

    Lizzette Crispin EMPIRE NETWORK REALTY

    824 Lake Elbert Ct, Winter Haven, FL 33881
  • /35

    $103,900

    • 3 Beds
    • 2 Baths
    • 1,760 Sq Ft

    2703 Lindrick Ct Unit 771, Winter Haven, FL 33881

    Experience luxury living in this stunning 1760 sq ft, triple-wide home, packed with numerous modern updates. Homes in the Four Lakes Golf & Country Club, a 55+ golf community in Winter Haven, are on lot leased land. Owning the home, but not the land, you pay a monthly lot rent of $ 783 which gives you and your guest access to the amenities of the community. Come experience luxury living and enjoy

    Kathy Sutak Renee's Resales

    2703 Lindrick Ct Unit 771, Winter Haven, FL 33881
  • /81

    $69,900

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

    630 Century Dr, Winter Haven, FL 33881

    If you're looking for that special home in the Central Florida Chain-of-Lakes area, this is it! This 1248 sq. ft. 2BR/2BA manufactured home is located close to the center of the popular, 55+ gated community, Swiss Golf and Tennis. It provides a totally updated, open concept floor plan with plenty of room for relaxing or entertaining family/friends. There are two enclosed Florida rooms, one in the

    Cynthia Cole Sunset Home Sales

    630 Century Dr, Winter Haven, FL 33881
  • /52

    $325,000 Open House 1/10

    • 3 Beds
    • 2 Baths
    • 2,022 Sq Ft

    240 Golf Aire Blvd, Winter Haven, FL 33884

    TEE TIME? YES! Welcome to Lake Bess Country Club, a hidden gem of Winter Haven. This custom built home combines timeless design, and thoughtful craftsmanship throughout every detail. Designed for gatherings large and small, this home has a unique floor plan, with wonderful golf course views of the #1 green from most rooms. The great room sports hardwood and tile accented floors, an electric built

    Marti Sutton CENTURY 21 WATSON & MYERS REALTY

    240 Golf Aire Blvd, Winter Haven, FL 33884
  • /39

    $56,900

    • 2 Beds
    • 2 Baths
    • 840 Sq Ft

    632 Lake Henry Dr, Winter Haven, FL 33881

    Hidden Cove West / Lot #632 / 2 Bedroom/2 Bath / 840 Sq. Ft. / $56,900.00 LARGE CANAL LOT WITH A DECK AND A DOCK!! This home is in the perfect location. It is right on the canal, which means easy access to Lake Henry & it is steps away from the clubhouse, pool and activities! This home has so many great features, but here are just a few: Florida Room with glass windows Bonus Room off of the back

    Jennifer Torres CRF Communities

    632 Lake Henry Dr, Winter Haven, FL 33881
  • /8

    $331,990 New Construction

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

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

    Open floor plan creates a unified living space with a large great room that overlooks the kitchen and dining area. The primary suite is tucked in the rear of the home offering plenty of privacy and features a spacious walk-in closet and shower.

    Meritage Homes Builder
    3745 Giorgio Dr Unit 37076787, Winter Haven, FL 33884

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