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Winter Haven, FL Homes for Sale with Pool

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  • /46

    $322,900

    • 3 Beds
    • 2 Baths
    • 1,871 Sq Ft

    4009 Bedford Ave, Winter Haven, FL 33884

    This fabulous Eco-Smart home is nestled in the highly desirable, maintenance-free, gated community of Traditions at Lake Ruby. Upon arrival, you’ll be welcomed by a charming front patio adorned with pavers, setting the stage for this beautifully maintained residence. Inside, the spacious great room boasts diagonally set tile flooring, crown molding, and oversized glass sliding doors that open to

    Eileen Belanger CENTURY 21 MYERS REALTY LAKE WALES

    4009 Bedford Ave, Winter Haven, FL 33884
  • /14

    $264,000 New Construction

    • 3 Beds
    • 2 Baths
    • 1,269 Sq Ft

    3880 Giorgio Dr, Winter Haven, FL 33884

    Prepare dinner while catching up on the day's events from this home's chef-inspired kitchen which overlooks a great room.

    Meritage Homes Builder
    3880 Giorgio Dr, Winter Haven, FL 33884
  • /12

    $344,999 New Construction

    • 5 Beds
    • 3 Baths
    • 2,471 Sq Ft

    5540 Taverna Loop, Winter Haven, FL 33884

    Check out the Indigo, a spacious two-story, 5-bedroom, 3-bathroom, 2-car garage home perfect for growing families or hosting guests. Enter the impressive foyer with soaring ceilings that creates an immediate sense of openness. From the foyer, the home effortlessly flows into the main living areas and kitchen. With quartz countertops throughout, stainless-steel appliances and a smart thermostat

    Casa Fresca Homes Builder
    5540 Taverna Loop, Winter Haven, FL 33884
  • /51

    $335,000

    • 3 Beds
    • 2 Baths
    • 2,140 Sq Ft

    731 Canberra Rd, Winter Haven, FL 33884

    Welcome to this beautifully maintained 3-bedroom, 2-bath home located in the highly sought-after Cypresswood golf community in Winter Haven. Enjoy resort-style living with an 18-hole golf course, 24-hour gated security, clubhouse, community pool, and more. Inside, the renovated kitchen features granite countertops and custom cabinetry. The spacious primary suite offers a large ensuite bath

    Melissa Witter KELLER WILLIAMS REALTY SMART 1

    731 Canberra Rd, Winter Haven, FL 33884
  • /39

    $280,000

    • 3 Beds
    • 2 Baths
    • 1,666 Sq Ft

    2817 Wingfoot Ct, Winter Haven, FL 33884

    Welcome to 2817 Wingfoot Ct, located in the desirable Cypresswood Golf Villas. This beautifully maintained villa sits along the 8th fairway of the prestigious Cypresswood Golf & Country Club, a guard-gated community offering both privacy and tranquility. Inside, you'll find three spacious bedrooms and two full bathrooms. The living and dining areas feature vaulted ceilings that enhance the open

    Dee Norris NEXTHOME NORRIS & COMPANY REAL

    2817 Wingfoot Ct, Winter Haven, FL 33884
  • /51

    $39,900

    • 2 Beds
    • 1.5 Baths
    • 672 Sq Ft

    866 Century Dr, Winter Haven, FL 33881

    You don't want to miss this lovely 2-bedroom/1.5-bath home in Hidden Golf Club, a 55+ community conveniently located on Lake Henry in Central Florida! This home comes partially furnished and has many of the extra features Florida living offers, not to mention, it is located in one of the few parks that still have fair monthly lot rent rates. The current lot rent for this home is $588. The home

    Patti Alvin Sunset Home Sales

    866 Century Dr, Winter Haven, FL 33881
  • /18

    $175,000

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

    523 Winter Terrace Unit 523, Winter Haven, FL 33881

    Welcome to this cozy 3-bedroom, 2-bath corner unit condo located in the lakefront community Winter Ridge on Lake Smart. Enjoy added privacy and convenience with two assigned parking spaces and a generously sized enclosed Florida Room—complete with a window unit for extra living space year-round.Inside, you’ll find tile flooring and carpet, and a split floorplan. Outside, take advantage of

    Pat Hancock THOMAS LYNNE REALTY GROUP LLC

    523 Winter Terrace Unit 523, Winter Haven, FL 33881
  • /17

    $268,999 New Construction

    • 3 Beds
    • 2 Baths
    • 1,615 Sq Ft

    6056 Navona Way, Winter Haven, FL 33884

    Feel at home with the Magenta, a single-story home with 3 bedrooms, 2 bathrooms, and a 2-car garage. This layout is a true gem, seamlessly blending modern comfort with Florida charm. Open concept living dazzles with luxury vinyl plank flooring throughout the main living areas. The kitchen, featuring quartz countertops, new stainless-steel appliances and ample storage overlooks the dining and

    Casa Fresca Homes Builder
    6056 Navona Way, Winter Haven, FL 33884
  • /32

    $119,000

    • 2 Beds
    • 2 Baths
    • 1,179 Sq Ft

    1264 Las Brisas Ln Unit 361, Winter Haven, FL 33881

    1264 Las Brisas Lane - Lot 361 2 Bedrooms | 2 Bathrooms | 1,179 Sq. Ft. | $119,000 Immaculate Home with Incredible Pond & Golf Course Views Welcome to this beautifully maintained, fully furnished Florida retreat located in the desirable Four Lakes community. Immaculate inside and out, this move-in-ready home offers drywall throughout, elegant crown molding, charming wainscoting, and easy-care

    Cheryl Dobbs CRF Communities

    1264 Las Brisas Ln Unit 361, Winter Haven, FL 33881
  • /34

    $435,000

    • 4 Beds
    • 3 Baths
    • 2,374 Sq Ft

    325 Terranova Blvd, Winter Haven, FL 33884

    Welcome home!! This 4 Bedroom, 3 Bath Pool home is what you have been waiting for. Recently remodeled, this home comes with a brand new roof, new screen on the pool cage, Remodeled pool with new marcit & new pool pump, new painting inside and out, new flooring, updated bathrooms and so much more! Located in the gated community of Terranova and just minutes from all that Winter Haven and Legoland

    Drew Swain SOHO RE AND CONSTRUCTION

    325 Terranova Blvd, Winter Haven, FL 33884
  • /69

    $165,000

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

    6315 Grove Pointe Drive South E, Winter Haven, FL 33884

    Welcome to 6315 Grove Pointe Drive SE, a beautifully maintained manufactured home in the highly sought after 55+ community of Garden Grove Oaks where you OWN your Land and enjoy low HOA fees in a peaceful, well-maintained neighborhood. This home features two generously sized bedrooms and two full bathrooms. The primary suite boasts a walk in closet and private en-suite bath with both a garden tub

    Anita Lowe LOCKHART & ASSOCIATES INC

    6315 Grove Pointe Drive South E, Winter Haven, FL 33884
  • /21

    $118,500

    • 2 Beds
    • 2 Baths
    • 1,347 Sq Ft

    1776 6th St NW Unit 303, Winter Haven, FL 33881

    Improved Price!! All new window in the building...Price improvement...Seller ready to sell! Beautifully maintained 55+ condominium located in Lake Ridge Winter Haven. This is a gated community offering a tranquil living space. Conveniently located near hospitals, restaurants, shopping, entertainment and so much more. This home offers everything you need to live a true Floridian lifestyle.

    Brenda Brooks CENTURY 21 MYERS REALTY

    1776 6th St NW Unit 303, Winter Haven, FL 33881
  • /31

    $59,900

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

    763 Century Ln, Winter Haven, FL 33881

    NEW PRICE! 2/2 home has open floor plan. Large eat-in kitchen has lots of cabinet space and opens into the dining room with built-in China cabinet. Appliances stay including the washer and dryer. Master bedroom has ensuite bathroom with a walk-in shower and added counter and storage space. Home comes furnished. Updated windows, Golf cart garage with negotiable golf cart has space for a workshop

    Leslie Yokshas Flamingo Mobile Home Sales

    763 Century Ln, Winter Haven, FL 33881
  • /79

    $2,250,000

    • 4 Beds
    • 4.5 Baths
    • 5,178 Sq Ft

    950 N Lake Otis Dr SE, Winter Haven, FL 33880

    There was a time when homes were designed to last, and this is one of them. Designed by award-winning architect Gene Leedy, this south-facing lakefront residence embodies a legacy of modernism uniquely attuned to Florida's landscape and climate. As a founding voice of the Sarasota School of Architecture, Leedy's vision was ahead of its time, helping to shape a movement that left its mark on

    Ashley Nuccio MICHAEL SAUNDERS & COMPANY

    950 N Lake Otis Dr SE, Winter Haven, FL 33880
  • /26

    $74,900

    • 2 Beds
    • 2 Baths

    218 Green Meadow Dr, Winter Haven, FL 33884

    If you are looking for the perfect retirement home that is fully furnished, this is the one for you. Located in gated Orange Manor West, a very popular 55+ community located in Southeast Winter Haven. This home is on leased land with a monthly fee of $513, which includes cable, internet and trash pickup. Park Lane Mobile Home 2 bedroom/2 bath with approximately 1,152 sf , king sized master

    Emily Muscarella

    218 Green Meadow Dr, Winter Haven, FL 33884
  • /42

    $169,900

    • 2 Beds
    • 2 Baths
    • 1,525 Sq Ft

    6518 Raintree Ln NE, Winter Haven, FL 33881

    Welcome to this beautifully maintained 2-bedroom, 2-bathroom manufactured home with an office in the desirable 55+ community of Brookhaven Village, where you OWN your land! Situated on a large lot with no rear neighbors, this property offers an incredible sense of privacy and tranquility.From the moment you enter, you’ll notice the care and updates that have gone into this home over the

    Patricia de Graaff RE/MAX HERITAGE PROFESSIONALS

    6518 Raintree Ln NE, Winter Haven, FL 33881
  • /34

    $45,900

    • 2 Beds
    • 2 Baths
    • 1,320 Sq Ft

    378 Alpine Dr Unit 378, Winter Haven, FL 33881

    Swiss Village / Lot #378 / 2 Bedroom/2 Bath / 1,320 Sq. Ft. / $45,900.00 PRICE REDUCED TO AN ALL TIME LOW on this gorgeous home, in this much sought after community, with great curb appeal and popular floor plan. This home offers: Freshly Painted Walls, Luxury Vinyl Plank Flooring, Additional Square Footage in Florida Room, Roof Over Roof, Energy efficient French Doors, Irrigation, Screen Around

    Jennifer Torres CRF Communities

    378 Alpine Dr Unit 378, Winter Haven, FL 33881
  • /31

    $415,000

    • 4 Beds
    • 2 Baths
    • 2,232 Sq Ft

    1450 Haines Dr, Winter Haven, FL 33881

    Welcome to this well-maintained 4-bedroom, 2-bath residence built in 2021, offering over 2,200 sq. ft. of comfortable living space. This property combines modern construction and energy efficiency with solar power panels! The home features an open-concept layout with generously sized living and dining areas designed for everyday functionality as well as a loft upstairs. The kitchen connects

    Amanda Gribbin EMAJIN REALTY LLC

    1450 Haines Dr, Winter Haven, FL 33881
  • /44

    $119,900

    • 2 Beds
    • 2 Baths
    • 1,029 Sq Ft

    700 Mirror Terrace NW Unit 303, Winter Haven, FL 33881

    Welcome to SPRING LAKE TOWERS, a premier 55+ community in Winter Haven, Florida offering a relaxed lakefront lifestyle with this well-maintained 2-bedroom, 2-bath condo featuring an open floor plan with stunning lake views, a 12' x 22' great room connected to the kitchen via convenient pass-through, spacious 12' x 18' Primary suite with private bathroom and walk-in closet, 10' x 13' second

    Kevin Tison LPT REALTY, LLC

    700 Mirror Terrace NW Unit 303, Winter Haven, FL 33881
  • /95

    $695,000

    • 3 Beds
    • 2 Baths
    • 2,773 Sq Ft

    1336 Oakmont Dr, Winter Haven, FL 33884

    Welcome to your personal haven and next chapter in beautiful Lake Ashton—Central Florida’s premier 55+ active-adult community. This immaculate oasis radiates style, elegance, and Florida charm at every turn. From the striking bronze facia and windows to the fresh paint scheme and professional landscaping with concrete curbing, to the panoramic bronze-domed screened lanai with custom outdoor

    Brad Kirwan GLOBAL LIFESTYLE LLC

    1336 Oakmont Dr, Winter Haven, FL 33884
  • /32

    $121,000

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

    1255 Las Brisas Ln Unit 415, Winter Haven, FL 33881

    2 Bedroom | 2 Bath | 1,438 Sq Ft | $121,000 Welcome to your dream home in the heart of Four Lakes Golf Club! This one-of-a-kind property is designed for comfort - perfect for those looking to embrace the next chapter of life. Just walking up to the house, it already feels unique and inviting. As you enter the home, on your left, you will find the guest bedroom, accessible through elegant double

    Cheryl Dobbs CRF Communities

    1255 Las Brisas Ln Unit 415, Winter Haven, FL 33881
  • /39

    $399,900

    • 4 Beds
    • 2.5 Baths
    • 2,364 Sq Ft

    2674 San Marco Way, Winter Haven, FL 33884

    One or more photo(s) has been virtually staged. PRICE REDUCED and SELLERS MOTIVATED! Discover this stunning 2023 upgraded, move-in ready home that effortlessly blends style and space with great functionality. From the moment you step inside, you’re welcomed by a formal dining room which can also be a flex space or home office. The heart of the home features a bright, open-concept layout that

    Amy Kozelka CENTURY 21 CIRCLE

    2674 San Marco Way, Winter Haven, FL 33884
  • /20

    $40,000

    • 2 Beds
    • 2 Baths
    • 975 Sq Ft

    187 Valencia Dr SE, Winter Haven, FL 33884

    Incredible Opportunity! Fixer-Upper with Unlimited Potential & Unmatched Charm! Homes in Orange Manor East, a 55+ pet friendly community are on lot leased land in Winter Haven, Florida. Owning the home, but not the land, you pay a monthly lot rent of $536 which gives you and your guest access to the amenities of the community. Trash also included in the lot fee. Located in Orange Manor

    Bette Johnson Renee's Resales

    187 Valencia Dr SE, Winter Haven, FL 33884
  • /9

    $264,000 New Construction

    • 3 Beds
    • 2 Baths
    • 1,269 Sq Ft

    Denali Plan at VillaMar - Classic Series, Winter Haven, FL 33884

    Prepare dinner while catching up on the days events from this homes chef-inspired kitchen which overlooks a great room and dining area. Well appointed primary suite provides a restful retreat at the end of the day and has a spacious walk-in closet.

    Meritage Homes Builder
    3745 Giorgio Dr Unit 37076780, Winter Haven, FL 33884
  • /2

    $318,250 New Construction

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

    3857 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
    3857 Giorgio Dr, Winter Haven, FL 33884
  • /49

    $330,000

    • 5 Beds
    • 3 Baths
    • 2,616 Sq Ft

    2005 Carnostie Rd, Winter Haven, FL 33884

    Short Sale. Welcome home to this inviting 5-bedroom, 3-bath family home offering 2,601 sq. ft. of comfortable living on an oversized lot in the sought-after VillaMar community! ? This move-in ready home is priced to sell fast, and the seller is motivated; don’t wait on this one! Step inside and enjoy the spacious, open-concept layout designed with families in mind. The main floor features a

    Sharonda Lawrence ASCENSION REALTY INTERNATIONAL

    2005 Carnostie Rd, Winter Haven, FL 33884
  • /3

    $389,990 New Construction

    • 4 - 5 Beds
    • 3 Baths
    • 2,500 Sq Ft

    Winston Plan at Willowbrook North, Winter Haven, FL 33881

    The Winston floorplan offers a spacious two-story layout with four bedrooms and three full bathrooms. This well-designed home includes a two-car garage and features a functional flex room on the main level, ideal for a home office or extra living space. The first floor includes a cozy great room adjacent to the cafe and covered patio, creating an inviting space for relaxation and entertaining.

    Dream Finders Homes Builder
    0 Fl-544 St Unit 37521594, Winter Haven, FL 33881
  • /25

    $465,000

    • 3 Beds
    • 2 Baths
    • 1,734 Sq Ft

    1151 Carefree Cove Dr, Winter Haven, FL 33881

    A Winter Haven Chain of Lakes Home with a large screened pool and boathouse for under 500K? Yes! This 3-bedroom, 2-bath home sits on Lake Conine and has received a first-class renovation from roof to floors. The beautiful lakefront home features a brand new roof, 4-ton A/C, and water heater all installed in 2025. The interior living area features new luxury vinyl plank, new fixtures, new doors,

    Jonathan Minerick HOMECOIN.COM

    1151 Carefree Cove Dr, Winter Haven, FL 33881
  • /33

    $260,000

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

    2809 Wingfoot Ct, Winter Haven, FL 33884

    GOLF COURSE HOME! WELCOME TO THIS AWESOME GOLF VILLA WITH A FAIRWAY VIEW OF THE 8TH HOLE. WELL MAINTAINED HOME. ALL APPLIANCES REMAIN. TANKLESS WATER HEATER. FRESH PAINT. GENEROUS SIZED ROOMS, BEAUTIFUL SUNROOM/FAMILY ROOM WITH OUTDOOR PATIO OVERLOOKS GOLF. FRONT COURTYARD IS PRIVATE AND INVITING. YOUR OWN COVERED PARKING, CARPORT KEEPS CAR PROTECTED. PRIVATE ENTRANCE. GUARD GATED COMMUNITY, LOW

    Patricia France HAPPY DAYS REALTY LLC

    2809 Wingfoot Ct, Winter Haven, FL 33884
  • /17

    $274,990 New Construction

    • 3 Beds
    • 2 Baths
    • 1,492 Sq Ft

    2751 San Marco Way, Winter Haven, FL 33884

    This thoughtfully designed single-story home offers 3 bedrooms, 2 bathrooms, and 1,492 square feet of functional living space with a 2-car garage. The open-concept layout features a spacious great room that flows into the dining area and kitchen, creating a comfortable space for everyday living and entertaining. The kitchen includes a center island, pantry, and dedicated refrigerator space, with

    Maronda Homes Builder
    2751 San Marco Way, Winter Haven, FL 33884
  • /80

    $421,900 Open Sat 11AM - 3PM

    • 4 Beds
    • 3 Baths
    • 1,927 Sq Ft

    4016 Carteret Dr, Winter Haven, FL 33884

    Welcome to 4016 Carteret Drive — a refined 4-bedroom, 3-bathroom lakefront sanctuary located in the incredible 55+ Traditions Community of Winter Haven. Perfectly positioned on one of the largest lots in the neighborhood and offering sweeping views of Ruby Lake, this exceptional residence blends luxury, comfort, and thoughtful upgrades throughout. From the moment you arrive, you'll appreciate the

    Drew Wilson AMPLIFY REAL ESTATE SERVICES FL

    4016 Carteret Dr, Winter Haven, FL 33884
  • /55

    $499,000 Open House 1/03

    • 3 Beds
    • 2 Baths
    • 2,805 Sq Ft

    5353 Hogan Ln, Winter Haven, FL 33884

    Welcome to 5353 Hogan Ln in Winter Haven, FL — a beautifully updated St John Floorplan located in the gated 55+ community of Lake Ashton. This freshly painted 3-bed, 2-bath residence features an open floor plan, an updated gourmet kitchen, a dedicated study with a stone fireplace, and a temperature-controlled oversized veranda (13' x 34') with panoramic views of the pond and conservation area.

    Susan Mayrant COLDWELL BANKER REALTY

    5353 Hogan Ln, Winter Haven, FL 33884
  • /42

    $309,990

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

    4202 San Rocco Way, Winter Haven, FL 33884

    Welcome to this move-in ready Cali floorplan corner home located in VillaMar, Winter Haven.This 4-bedroom, 2-bathroom residence offers 1,851 sq. ft. of well-designed living space. Built in 2023, the home features abundant natural light, granite countertops, ceramic tile flooring in the main living areas, carpeted bedrooms, and smart home technology for remote control and convenience.

    Jennifer NG CANVAS REAL ESTATE

    4202 San Rocco Way, Winter Haven, FL 33884
  • /30

    $350,990 New Construction

    • 5 Beds
    • 3 Baths
    • 2,601 Sq Ft

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

    Find all the space you need in our popular two-story Hayden floorplan in Harmony at Lake Eloise, one of our communities in Winter Haven, Florida. Inside this 5-bedroom, 3-bathroom home, you’ll find 2,601 square feet of flexible living space and a two-car garage. Step thru the front foyer and you're greeted with a flex room designed for work or play. Make your way to the kitchen on the first

    D.R. Horton Builder
    1651 Hummingbird Rd Unit 36202783, Winter Haven, FL 33880
  • /38

    $179,900

    • 2 Beds
    • 1.5 Baths
    • 1,280 Sq Ft

    2304 Isle Royale Ct SE, Winter Haven, FL 33880

    Calling all investors! This could be a great investment opportunity to add to your portfolio. This unit in a desirable neighborhood, close to shopping, walking distance to restaurants. Next to the Chain of Lakes Complex. The new Super Target is set to open next year and this unit is within walking distance of it. Lots of new development coming to the area. Property is move-in ready, new carpet,

    Angie Garcia RE/MAX HERITAGE PROFESSIONALS

    2304 Isle Royale Ct SE, Winter Haven, FL 33880
  • /35

    $369,000

    • 3 Beds
    • 3 Baths
    • 2,032 Sq Ft

    2733 Attwater Loop, Winter Haven, FL 33884

    DON'T MISS THIS HOME!!! This stunning split 3-bedroom, 3-bathroom home offers a spacious and thoughtful layout, complete with a versatile den/bonus room perfect for an office, craft space, or quiet retreat. HOA covers Lawn Care among other benefits! TWO OF THE BEDROOMS FEATURE EN-SUITE BATHROOMS ensuring privacy and luxury for guests or family. The primary suite is a true haven, boasting TWO

    Andrea Friedmann KELLER WILLIAMS REALTY SMART 1

    2733 Attwater Loop, Winter Haven, FL 33884
  • /31

    $259,900

    • 2 Beds
    • 2 Baths
    • 1,368 Sq Ft

    14 Enclave Dr, Winter Haven, FL 33884

    Fresh on the market is this meticulously maintained and professionally updated 2 bedroom 2 bath villa located in the sought after "Enclave" neighborhood in Cypresswood, a gated golf community in SE Winter Haven.The open floor plan features an expansive kitchen with breakfast nook, spacious living/dining room combo, split bedrooms with ample closets, inside laundry area equipped with a washer

    Steven Smith, PA LOCKHART & ASSOCIATES INC

    14 Enclave Dr, Winter Haven, FL 33884
  • /84

    $1,549,000

    • 7 Beds
    • 7 Baths
    • 7,448 Sq Ft

    3824 Gaines Dr, Winter Haven, FL 33884

    A true luxury lakefront masterpiece on the shores of Lake Eloise, one of the most beautiful lakes on the world-famous Winter Haven Chain of Lakes. This architecturally stunning modern estate delivers more than 7,400 sq ft of interior living space with 7 bedrooms, 5 full baths, and 2 half baths, blending contemporary design, industrial-inspired details, and resort-style outdoor

    Michael Stone THE STONES REAL ESTATE FIRM

    3824 Gaines Dr, Winter Haven, FL 33884
  • /34

    $82,500

    • 2 Beds
    • 2 Baths
    • 700 Sq Ft

    7094 Fairview Village Cir, Winter Haven, FL 33881

    Welcome to 7094 Fairview Village Circle in Winter Haven—a charming and well-maintained 2-bedroom, 2-bathroom split-level mobile home located in the peaceful, gated 55+ community of Fairview Village. This lakefront community offers an inviting and active lifestyle with access to a beautiful waterway—ideal for boating, kayaking, or fishing. The home features a unique layout with a cozy separation

    Patricia de Graaff RE/MAX HERITAGE PROFESSIONALS

    7094 Fairview Village Cir, Winter Haven, FL 33881

Showing Results 241 - 280, Page 7 of 18

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