821

Winter Haven, FL Homes for Sale with Pool

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  • /36

    $740,000

    • 4 Beds
    • 2 Baths
    • 2,217 Sq Ft

    264 Ruby Lake Ln, Winter Haven, FL 33884

    Discover a lakefront retreat in Southeast Winter Haven! This pristine, move-in-ready 4 Bedroom, 2Bathroom home with a dedicated office is perfectly positioned on private-access Lake Bess, complete with a slalom ski course. With direct connection to Lake Ruby, you'll enjoy access to TWO beautiful lakes featuring white sandy bottoms, tranquil waters, and limited boat traffic. These lakes are ideal

    Andrea Friedmann KELLER WILLIAMS REALTY SMART 1

    264 Ruby Lake Ln, Winter Haven, FL 33884
  • /46

    $79,900

    • 2 Beds
    • 2 Baths
    • 1,462 Sq Ft

    128 Lake Hazel Dr, Winter Haven, FL 33884

    Back on the market! Welcome to Orange Manor West in the desirable southeast Winter Haven area. This fully furnished double-wide manufactured home is located in a 55+ gated community. The spacious 2-bedroom, 2-bathroom home offers comfort, functionality, and a host of recent updates. The king-sized primary bedroom features dual walk-in closets and an ensuite bathroom with a new vanity sink

    Dawn Van Meter KELLER WILLIAMS REALTY SMART 1

    128 Lake Hazel Dr, Winter Haven, FL 33884
  • /26

    $242,500

    • 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
  • /17

    $165,000

    • 2 Beds
    • 2 Baths
    • 1,369 Sq Ft

    6236 Knotty Pine Drive South E, Winter Haven, FL 33884

    Welcome to Garden Grove Oaks – a friendly, active 55+ community in beautiful Winter Haven and you OWN THE LAND! This well-maintained 2-bedroom, 2-bathroom manufactured home with a bonus office/den and Florida room offers the perfect blend of comfort, functionality, and easy Florida living. Step inside and you’ll immediately appreciate the bright, open layout, featuring a spacious living area

    Nicole Castro DREAM REALTY GROUP

    6236 Knotty Pine Drive South E, Winter Haven, FL 33884
  • /51

    $219,000

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

    715 Magnolia Place, Winter Haven, FL 33884

    Waterfront condo on the Winter Haven Chain of Lakes! 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

    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

    $149,900

    • 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. | Priced Reduced to $149,900 from $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

    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

    $124,000

    • 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

    $345,000

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

    5197 Pebble Beach Blvd, Winter Haven, FL 33884

    PRICE REDUCED $10,000.00.. MOTIVATED SELLER!!!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

    Lori Raath LAKE ASHTON REALTY INC.

    5197 Pebble Beach Blvd, Winter Haven, FL 33884
  • /5

    $309,366 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
  • /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
  • /16

    $71,000

    • 1 Bed
    • 1 Bath
    • 931 Sq Ft

    100 El Camino Dr Unit 111, Winter Haven, FL 33884

    Owner motivated and ready to negotiate — WOW! This BEAUTIFUL 931 SF 1BR/1BA FIRST-FLOOR condo in Orchid Springs offers stunning lagoon views! Located in the 55+ Granada Building, where at least one occupant must be 55+. IMMEDIATELY AVAILABLE and MOVE-IN READY! Step into an open, airy floor plan with tile throughout, creating a bright and spacious feel. The dining area, living room, and bonus room

    Sharon Gastelbondo LPT REALTY, LLC

    100 El Camino Dr Unit 111, Winter Haven, FL 33884
  • /72

    $539,000

    • 3 Beds
    • 2 Baths
    • 2,443 Sq Ft

    5200 Pebble Beach Blvd, Winter Haven, FL 33884

    Back on the Market! Seller Motivated! With fabulous WATER VIEWS and GOLF COURSE views, this elegant residence offers a perfect tropical retreat. A large pool with a attached spa invites year-round outdoor enjoyment, framed by the beauty of Lake Ashton's natural surroundings. Ideally situated near Lake Wales and Winter Haven this home offers exceptional access to shopping and entertainment;

    Lori Raath LAKE ASHTON REALTY INC.

    5200 Pebble Beach Blvd, Winter Haven, FL 33884
  • /12

    $299,990 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

    $9,999

    • 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
  • /2

    $317,990 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,305 Sq Ft

    4057 Giorgio Dr, Winter Haven, FL 33884

    Under Construction. his BEATIFUL ELSTON II Model home has 4 bedrooms, 2.5 baths & a 2-car garage-2305 SqFt. NEWLY UPGRADED! Large 2-STORY open floor plan with spacious great room & kitchen to entertain & enjoy the company of your guests. All bedrooms & laundry located on the 2nd floor. Your very spacious master suite located on the 2nd floor with a large walk-closet & a double sink vanity with

    Paul King DR HORTON REALTY OF CENTRAL FLORIDA LLC

    4057 Giorgio Dr, Winter Haven, FL 33884
  • /64

    $144,900

    • 3 Beds
    • 2 Baths
    • 1,218 Sq Ft

    276 18th St NE, Winter Haven, FL 33881

    Discover the potential of this 3-bedroom, 2-bathroom home in Winter Haven, offering a versatile layout with a combined living and dining room perfect for everyday living or entertaining. The property features a fenced-in backyard, a spacious yard with room to customize, an empty pool ready for renovation or removal, and an enclosed back porch that adds extra flexible living space. With solid

    Jana Lutz COLDWELL BANKER REALTY

    276 18th St NE, Winter Haven, FL 33881
  • /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
  • /12

    $260,000 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
  • /38

    $152,900

    • 3 Beds
    • 2 Baths
    • 1,785 Sq Ft

    6399 Lolly Bay Loop NE, Winter Haven, FL 33881

    Discover this rare find—a beautifully maintained three-bedroom, two-bath manufactured home nestled in a vibrant 55+ community. Boasting a bright and open floor plan, this home features formal living and dining areas, as well as a spacious family room, perfect for entertaining or relaxing. The living room’s large bay windows, all recently upgraded, provide stunning natural light and a view to

    Logan Coon KELLER WILLIAMS WINTER PARK

    6399 Lolly Bay Loop NE, Winter Haven, FL 33881
  • /16

    $289,950 New Construction

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

    5351 Mickey Ave, Lake Wales, FL 33859

    This Azure floor plan offers a welcoming formal entry and hallway. A spacious great room with kitchen is open to dining and family entertainment area that leads to a covered patio. Also included is a great sized primary bedroom with a primary bath and walk-in closet. Included features: 9"4' ceilings and 8' doors, 42' cabinets and white quartz counter tops in kitchen, ceramic tile throughout the

    Stephanie Morales AXEN REALTY, LLC

    5351 Mickey Ave, Lake Wales, FL 33859
  • /19

    $255,000

    • 3 Beds
    • 2 Baths
    • 1,467 Sq Ft

    878 Killearn Blvd, Winter Haven, FL 33880

    PRICE CHANGE – NO HOA & PRICED TO SELL! Opportunity meets value in this 3-bedroom, 2-bath home located in a well-established Winter Haven neighborhood. Positioned on a spacious, fully fenced corner lot, this property offers exceptional outdoor space and includes an above-ground pool, perfect for cooling off on hot Florida days, entertaining guests, or enjoying your own private backyard retreat.

    Barbi Rodriguez SIGNATURE INTERNATIONAL REAL E

    878 Killearn Blvd, Winter Haven, FL 33880
  • /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
  • /39

    $270,000

    • 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
  • /34

    $274,900 New Construction

    • 3 Beds
    • 2 Baths
    • 1,260 Sq Ft

    2362 Brassie Ct, Winter Haven, FL 33884

    One or more photo(s) has been virtually staged. Nestled in the growing Villamar community, this beautifully maintained 3-bedroom, 2-bath Meritage Home offers modern comfort and an ideal location near Chain of Lakes Elementary. Built with energy efficiency in mind, this newer home features an inviting open-concept floor plan where the kitchen flows seamlessly into the spacious great room—perfect

    Millie Brockmeyer RE/MAX INNOVATION

    2362 Brassie Ct, Winter Haven, FL 33884
  • /28

    $315,000

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

    1228 Denali Dr, Winter Haven, FL 33881

    Newer 4 bedroom home for sale in Winter Haven, Florida, located in the Lake Lucerne II community in Polk County with no CDD fees and a low quarterly HOA. Built in 2023 by KB Home, this single-story residence offers approximately 1,707 square feet of modern living space designed for comfort, accessibility, and long-term value. Thoughtfully designed with universal design features, the home includes

    Jackie Mazurowski KELLER WILLIAMS REALTY SMART 1

    1228 Denali Dr, Winter Haven, FL 33881
  • /41

    $305,000 Open Sun 11AM - 2PM

    • 3 Beds
    • 2 Baths
    • 1,597 Sq Ft

    3927 Palazzo Place, Winter Haven, FL 33884

    Do you want to own a true one of a kind? A true one of one? This is truly a special opportunity to own a home that is as unique as it is inviting. This property is the FINAL Amarylis model available in the entire community — a rare find that offers both distinction and immediate availability. Unlike new construction opportunities that often involve lengthy build timelines, unexpected delays, and

    Iliana Perez MAINFRAME REAL ESTATE

    3927 Palazzo Place, Winter Haven, FL 33884
  • /71

    $142,980

    • 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

    $98,000

    • 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
  • /20

    $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

    $144,900

    • 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
  • /12

    $268,396 New Construction

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

    3888 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
    3888 Giorgio Dr, Winter Haven, FL 33884
  • /43

    $225,000

    • 2 Beds
    • 2 Baths
    • 1,118 Sq Ft

    3343 Livingston Way, Winter Haven, FL 33884

    Located in the highly desirable 55+ maintenance-free gated community of Traditions on Lake Ruby, this wonderful 2-bedroom, 2-bathroom home offers charm, functionality, and an exceptional lifestyle. Upon arrival, you’re greeted by a welcoming Screened-in front porch decked out with tile flooring. Inside, the open-concept floor plan features a spacious living room with vaulted ceilings, Laminate

    Eileen Belanger CENTURY 21 MYERS REALTY LAKE WALES

    3343 Livingston Way, Winter Haven, FL 33884
  • /19

    $339,950 New Construction

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

    5355 Mickey Ave, Lake Wales, FL 33859

    This thoughtfully designed Slate home opens with two bedrooms flanking a full hall bath. Beyond the entry, you’ll find an open layout with a dining nook, a great room with access to an inviting covered patio, and a kitchen with a center island, walk-in pantry and abundant cabinetry. The owner’s suite is nearby, offering a generous walk-in closet and a private bath with a shower and a separate

    Stephanie Morales AXEN REALTY, LLC

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

    $312,900 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

    $356,990 New Construction

    • 4 Beds
    • 3.5 Baths
    • 2,298 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

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