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Cypress Gardens, FL Homes for Sale with Pool

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  • /67

    $975,000

    • 4 Beds
    • 4 Baths
    • 3,555 Sq Ft

    200 Island Way, Winter Haven, FL 33884

    Welcome to your own slice of paradise on the private shores of Lake Lewis located in the highly sought-after gated community of Orchid Springs Estates! This stunning Mediterranean-style estate offers the perfect blend of luxury, comfort, and timeless elegance. Boasting 4 spacious bedrooms and 4 full baths, this custom-designed home features a beautifully appointed kitchen ideal for entertaining,

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    Steve Lockhart

    LOCKHART & ASSOCIATES INC

    (863) 343-1106

    200 Island Way, Winter Haven, FL 33884
  • /66

    $429,900

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

    144 Beverly Dr, Winter Haven, FL 33884

    *If you use the preferred lender, your appraisal fee will be reimbursed back to you at closing!* Immaculate and updated pool home ideally located in SE Winter Haven just two blocks from Chain of Lakes access. This well-cared for pool residence features a sleek modern appearance with comfortable living spaces and an impressive level of quality updates found throughout. Extensive list of recent

    Christina Loesch AGILE GROUP REALTY

    144 Beverly Dr, Winter Haven, FL 33884
  • /23

    $450,000

    • 4 Beds
    • 3 Baths
    • 2,206 Sq Ft

    252 Lake Link Rd, Winter Haven, FL 33884

    Welcome to this beautifully updated 4 bedroom, 3 bath pool home, ideally positioned on a half-acre lot in the highly desirable gated community of Lake Link. Surrounded by oak-lined streets and refreshing lake breezes, this home combines elegant updates with a functional layout designed for everyday living and entertaining.Inside, an inviting open floor plan is anchored by the gourmet

    Katie Melson THE STONES REAL ESTATE FIRM

    252 Lake Link Rd, Winter Haven, FL 33884
  • /32

    $434,000

    • 4 Beds
    • 3 Baths
    • 2,420 Sq Ft

    415 Smiley Ct, Winter Haven, FL 33884

    READY TO MOVE !!!! 4 spacious bedrooms ; Large great room with excellent natural light ??? Open kitchen integrated into the dining room, ideal for family sharing ?? 3 full bathrooms: ?? Covered garage for 5 vehicles ?? Large private pool with terrace area for outdoor enjoyment ?? Large side garden, perfect for games, pets, or relaxing Located in a quiet and safe area, this property combines

    Adriana Sanchez AGENT TRUST REALTY CORPORATION

    415 Smiley Ct, Winter Haven, FL 33884
  • /35

    $359,900

    • 4 Beds
    • 2 Baths
    • 1,977 Sq Ft

    111 Beverly Dr, Winter Haven, FL 33884

    Perfect 4 Bed / 2 Bath Pool Home for entertaining! Don’t miss this beautifully maintained 4-bedroom, 2-bath split-plan home featuring the sought-after John Wood floor plan. Enjoy Florida living with a large screened-in pool and an oversized lanai, perfect for entertaining or relaxing outdoors. Recent updates include * remodeled kitchen and baths with Granite Counter-tops * a 7-year-old roof *

    Barry Macchione REMAX EXPERTS

    111 Beverly Dr, Winter Haven, FL 33884
  • /44

    $118,900

    • 2 Beds
    • 2 Baths
    • 1,378 Sq Ft

    200 El Camino Dr Unit 202, Winter Haven, FL 33884

    WOW! THIS SPACIOUS 2 BEDROOM,2 BATH CONDO HAS SENSATIONAL VIEWS OF THE LAGOON,GARDENS AND FOUNTAIN OUT BACK. ORCHID SPRINGS IS KNOWN FOR BEING A TROPICAL OASIS THAT BACKS UP TO A PRESERVE WITH ALL KINDS OF WILDLIFE THAT YOU CAN WATCH FROM THE WALL OF WINDOWS IN YOUR FL. ROOM. A GREAT PLACE TO HAVE YOUR MORNING COFFEE OR A GLASS OF WINE IN THE LATE AFTERNOON. THE FOUNTAIN OUTSIDE YOUR BACK WINDOWS

    Christina Ashley DALTON WADE INC

    200 El Camino Dr Unit 202, Winter Haven, FL 33884
  • /31

    $360,000

    • 3 Beds
    • 2 Baths
    • 1,847 Sq Ft

    144 Waterside Cir, Winter Haven, FL 33880

    Welcome home! This beautifully maintained 3-bedroom, 2-bathroom, 2 car garage home offers a perfect blend of comfort and style. Waterside Village is a boutique (48 homes) community located in the heart of Winter Haven. Step inside to discover an open-concept floor plan filled with natural light, high ceilings, and spacious living and dining areas ideal for both relaxing and entertaining. The

    Anita Lowe LOCKHART & ASSOCIATES INC

    144 Waterside Cir, Winter Haven, FL 33880
  • /35

    $485,000

    • 4 Beds
    • 3 Baths
    • 2,569 Sq Ft

    305 Hernando Rd, Winter Haven, FL 33884

    Welcome to your Dream home!! Step into this stunning residence through a spacious, light-filled foyer and prepare to be impressed by the thoughtfully, well maintained designed layout and exceptional features throughout. This home offers oversized bedrooms and a versatile bonus room—perfect for a game room, home office, or even a private in-law suite. This home has a formal living area, family

    Sherry Sapp COLDWELL BANKER REALTY

    305 Hernando Rd, Winter Haven, FL 33884
  • /40

    $135,000

    • 2 Beds
    • 1 Bath
    • 840 Sq Ft

    900 Avenue Z SE Unit B2, Winter Haven, FL 33880

    Discover relaxed Florida living in this delightful 2-bedroom, 1st-floor condo in the sought-after Sandy Cove community. Perfectly blending comfort and convenience, this charming residence offers a low-maintenance lifestyle with access to top-tier amenities, including a sparkling community pool and a private dock for fishing or relaxing on scenic Lake Lulu—part of the popular Winter Haven Chain of

    Josh Taylor VILLAGE REALTY OF WINTER HAVEN

    900 Avenue Z SE Unit B2, Winter Haven, FL 33880
  • /17

    $265,000

    • 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
  • /28

    $90,000

    • 2 Beds
    • 2 Baths
    • 1,361 Sq Ft

    100 El Camino Dr Unit 202, Winter Haven, FL 33884

    Beautiful 2 Bedroom, 2 Bathroom Condo in a Serene 55+ Community!Step into this gorgeous condo featuring an open floor plan that creates a spacious and inviting atmosphere. The home offers a large living room, open dining area, and two generously sized bedrooms—perfect for comfort and relaxation. Brand-new AC unit just installed!Nestled within a peaceful 55+ community, you'll enjoy

    Wes Brown MARK SPAIN REAL ESTATE

    100 El Camino Dr Unit 202, Winter Haven, FL 33884
  • /54

    $589,000

    • 3 Beds
    • 3 Baths
    • 1,900 Sq Ft

    125 Lake Roy Dr, Winter Haven, FL 33884

    Welcome to 125 Lake Roy Drive—an extraordinary, move-in-ready lakefront estate delivering the true Florida lifestyle with zero compromises and no HOA. Set on a beautifully landscaped lot with ample parking for vehicles, boats, RVs, and lake toys, this home offers unmatched flexibility and convenience for waterfront living. Perfectly positioned on the prestigious South Chain of Lakes, this

    Craig Murrell REMAX EXPERTS

    125 Lake Roy Dr, Winter Haven, FL 33884
  • /10

    $79,000

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

    100 El Camino Dr Unit 110, Winter Haven, FL 33884

    FIRST FLOOR 2 BED/2BATH Located in the Granada building of Orchid Springs with assigned parking right at your front door!. This property is situated within a 55+ age-restricted community. A small pet is allowed on the premises. Amenities include a clubhouse and community pool with views of the lagoon area right outside the back door of your unit. Additionally, Gas, Water, Trash, Sewer and

    Sharminee Lopez PARALLEL REALTY LLC

    100 El Camino Dr Unit 110, Winter Haven, FL 33884
  • /40

    $250,000

    • 2 Beds
    • 2 Baths
    • 1,667 Sq Ft

    454 San Jose Dr, Winter Haven, FL 33884

    Fall in love with the laid-back Florida lifestyle! *** BRAND NEW TILE ROOF *** This standout 2-bedroom, 2-bathroom patio home sits on an expansive, oversized lot that offers unmatched outdoor space, lush landscaping, and total privacy with no rear neighbors. Originally built as a model home and lovingly cared for by its one and only family, this property combines charm, space, and serenity in a

    Bethany Cromwell KELLER WILLIAMS REALTY SMART

    454 San Jose Dr, Winter Haven, FL 33884
  • /54

    $215,000

    • 2 Beds
    • 2 Baths
    • 1,250 Sq Ft

    386 San Jose Dr, Winter Haven, FL 33884

    A Patio Home in Orchid Spring a well-maintained Community. Located in Winter Haven within 3 miles of Lego Land. It’s a 2 Bedroom 2 bath home with a living room, back porch screened in perfect for Barbeques or entertaining. A living room a dinette adjacent to the kitchen that has a pantry the closet in the dinette is located behind the front door. The laundry room is in the 2-car garage. Also,

    Lamont Nixon CHARLES RUTENBERG REALTY ORLANDO

    386 San Jose Dr, Winter Haven, FL 33884
  • /37

    $299,000

    • 2 Beds
    • 2 Baths
    • 1,843 Sq Ft

    441 San Jose Dr, Winter Haven, FL 33884

    Welcome to this exceptional 2-bedroom, 2-bathroom patio home nestled within the highly sought after Orchid Springs community. Positioned on an expansive double lot, this residence offers a serene and secluded wooded vista visible from the open kitchen and the generously proportioned screened patio. Noteworthy exteri9or features; Paved drive and walkways, attractive canopies and covered front

    Dee Norris NEXTHOME NORRIS & COMPANY REALTY

    441 San Jose Dr, Winter Haven, FL 33884
  • /13

    $105,000

    • 2 Beds
    • 2 Baths
    • 851 Sq Ft

    817 Orchid Springs Dr Unit 817, Winter Haven, FL 33884

    PRICE REDUCED! Great Investment Property! Clean and move in ready! Ground Floor so no steps! 2 Bedroom 1 1/2 Bath Condo in the convenient community of Orchid Springs. Laminate Flooring! Schedule a showing today!

    Lisa Anderson LA ROSA REALTY PRESTIGE

    817 Orchid Springs Dr Unit 817, Winter Haven, FL 33884
  • /59

    $330,000

    • 3 Beds
    • 2 Baths
    • 1,788 Sq Ft

    53 Paine Dr, Winter Haven, FL 33884

    PRICE REDUCED! Come take a look at this beautiful pool home in Garden Grove. Located in the desirable SE Winter Haven and only 5 minutes from LegoLand. This home has 3 Bedrooms and 2 Baths, sits on a corner lot and has NO HOA. Walk up the front steps to be welcomed into the home. This home has been well maintained and upgraded so you don't have to. With new windows and sliding glass doors, the AC

    Bree Allison KELLER WILLIAMS TAMPA CENTRAL

    53 Paine Dr, Winter Haven, FL 33884
  • /52

    $98,000

    • 2 Beds
    • 2 Baths
    • 1,579 Sq Ft

    100 El Camino Dr Unit 309, Winter Haven, FL 33884

    Cable and Internet included in HOA Fees, valued around $250 monthly. Cable coverage should follow to a secondary home. Move-in ready with room to make it your own! Check out this 3rd FLOOR UNIT spanning over 1,500 square feet, located in the beautifully maintained 55+ Granada Building in Orchid Springs! This bright and spacious 2 bedroom, 2 bath condo with an OVERSIZED bonus room offers GORGEOUS

    Chrissi Jasso ASSOCIATE REALTY

    100 El Camino Dr Unit 309, Winter Haven, FL 33884
  • /37

    $299,900

    • 3 Beds
    • 2 Baths
    • 1,729 Sq Ft

    3817 Osprey Pointe Cir, Winter Haven, FL 33884

    This 3 bedroom 2 bath home is located in Osprey Pointe, a waterfront community on Lake Ned. The eat-in kitchen has beautiful wood cabinets complete with refrigerator, microwave, and cook top stove. Sliding glass doors lead to the lanai providing a great view of the back yard. The exterior has pre-caste walls built to withstand winds up to 140 mph. This quiet and well kept community has a

    Bob Gibilisco COLDWELL BANKER REALTY

    3817 Osprey Pointe Cir, Winter Haven, FL 33884
  • /23

    $155,000

    • 2 Beds
    • 2 Baths
    • 888 Sq Ft

    845 Orchid Springs Dr, Winter Haven, FL 33884

    MOTIVATED SELLER!!!! Unique Opportunity Near LEGOLAND® and Shopping Area Excellent condo in a prime location, ideal for living or investing. Just minutes from LEGOLAND® Florida, in a quiet and high-demand area. Key Features:Strategic Location: Close to shops, restaurants, supermarkets, and with easy access to major roads.Well-Maintained Condo: Located in a residential complex

    Silis Marquez Leon PROPERTY OUTLET INTERNATIONAL

    845 Orchid Springs Dr, Winter Haven, FL 33884
  • /28

    $314,990

    • 3 Beds
    • 3 Baths
    • 1,594 Sq Ft

    1808 4th Ct SE, Winter Haven, FL 33880

    Welcome home, where comfort and elegance await at every turn. Upon entering, you're greeted by a warm fireplace, framed by nicely painted walls in a soothing neutral color scheme. The 3 bedrooms 2 baths and the study room home at Winter Haven location! The perfect comfort and convenience area. The big pool size, with lot of fruits trees. This home is minutes from LEGOLAND Florida Resort and just

    Trinh Le SOGO REAL ESTATE SERVICES LLC

    1808 4th Ct SE, Winter Haven, FL 33880
  • /33

    $99,999

    • 2 Beds
    • 2 Baths
    • 1,361 Sq Ft

    100 El Camino Dr Unit 102, Winter Haven, FL 33884

    Welcome to 100 El Camino Dr. Apt 102, a beautifully renovated 2-bedroom, 2-bathroom condo nestled in the serene Orchid Springs community of Winter Haven, Florida. This spacious 1,361 square-foot residence offers modern comforts and stylish finishes, making it the perfect place to call home.The condo has been fully updated, featuring contemporary fixtures and finishes throughout. With an

    Xiao Pang BLUE CHIP INTERNATIONAL REALTY LLC

    100 El Camino Dr Unit 102, Winter Haven, FL 33884
  • /52

    $249,900

    • 2 Beds
    • 2 Baths
    • 1,329 Sq Ft

    1644 Linz Ct, Winter Haven, FL 33884

    CUSTOM CUTIE! EXTERIOR PAINT, ROOF, IRRIGATION WATER, YARD MOWING, SHRUB TRIMMING, and SPECTRUM Internet/TV package is included in the reasonable monthly fees. This amazing 2022 Vienna Square end unit Villa has all the superb custom features you've been looking to find. Step into the bright, and open living area finished with smart home light switches to pair with your Alexa, accented walls,

    Marti Sutton CENTURY 21 WATSON & MYERS REALTY

    1644 Linz Ct, Winter Haven, FL 33884
  • /48

    $1,350,000

    • 5 Beds
    • 4.5 Baths
    • 4,513 Sq Ft

    1441 S Lake Roy Dr, Winter Haven, FL 33884

    CHAIN OF LAKES!!! POOL!!! 5 BEDROOMS AND 4.5 BATHROOMS!!! This is the listing you have been waiting for - look no further. This incredible residence is situated on over half an acre of maturely landscaped waterfront property and has a remarkable list of features and finishes. The sprawling floor plan encompasses 4,513SqFt of LIVING AREA with 5 generous bedrooms and 4.5 beautiful baths; 3.5 of

    Catherine Kluytenaar THE K TEAM REAL ESTATE SERVICES LLC

    1441 S Lake Roy Dr, Winter Haven, FL 33884
  • /46

    $259,000 New Construction

    • 2 Beds
    • 2 Baths
    • 1,164 Sq Ft

    1703 Linz Ct, Cypress Gardens, FL 33884

    **This property qualifies for a significant discount if closed by 10/31/2025. NEW CONSTRUCTION! This brand-new single-story, two bedroom, two bath Villa is located in Vienna Square, a 55+ gated community in Winter Haven. Live a low maintenance lifestyle with tranquil views from your screened lanai which is accessible from the villa’s open floor plan. This villa features a two car garage, paver

    Austin Schreiber DGCF REALTY ADVISORS LLC

    1703 Linz Ct, Cypress Gardens, FL 33884
  • /19

    $169,900

    • 3 Beds
    • 2.5 Baths
    • 1,584 Sq Ft

    5850 Cypress Gardens Blvd Unit 403, Winter Haven, FL 33884

    Discover the easy, maintenance-free living of this well-kept 3BR/2.5BA townhouse in SE Winter Haven. The downstairs shines with ceramic tile, a modern kitchen featuring granite countertops, wood cabinets, a breakfast bar, and a pantry. Enjoy separate living and family rooms, a handy half bath, inside laundry, and a private patio for relaxing. Upstairs, find three comfortable bedrooms, including a

    David Craig 1513 REALTY LLC

    5850 Cypress Gardens Blvd Unit 403, Winter Haven, FL 33884
  • /19

    $184,900

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

    2050 San Marcos Dr SE Unit 113, Winter Haven, FL 33880

    Welcome to this charming first-floor condominium in the heart of Winter Haven! Conveniently located on the renowned Chain of Lakes, this spacious 2-bedroom, 2-bathroom home offers the perfect blend of comfort and convenience. Step inside to enjoy an open and inviting floorplan with plenty of natural light throughout. The private outdoor patio provides a perfect space for morning coffee, relaxing

    Tony Insua Jr. CRAIG BURKE REAL ESTATE GROUP, LLC

    2050 San Marcos Dr SE Unit 113, Winter Haven, FL 33880
  • /27

    $215,000

    • 2 Beds
    • 2.5 Baths
    • 1,281 Sq Ft

    2352 Isle Royale Ct SE, Winter Haven, FL 33880

    Welcome Home to this charming 2 bedroom, 2.5 bathroom townhouse in Park Lake, one of Winter Haven's desirable communities located close to shopping, restaurants, schools, lakes, Legoland and the beautiful downtown Winter Haven area. This move in ready home offers a bright and spacious living area located on the first floor with new luxury vinyl flooring, fresh paint and a convenient half bath

    Wendy Watson KELLER WILLIAMS REALTY SMART 1

    2352 Isle Royale Ct SE, Winter Haven, FL 33880
  • /38

    $240,000

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

    1218 Vienna Square Dr, Winter Haven, FL 33884

    **This property qualifies for a closing cost credit up to $3,600 through the Seller’s preferred lender plus an additional $1,000 credit for carpet from the Seller.** Welcome to a peaceful and sought-after 55+ community of Vienna Square, this beautifully maintained 2-bedroom, 2-bathroom villa with a 2-car garage offers low-maintenance living with touches of elegance throughout. As you approach,

    Thomas Nickley KELLER WILLIAMS REALTY AT THE PARKS

    1218 Vienna Square Dr, Winter Haven, FL 33884
  • /36

    $240,000

    • 3 Beds
    • 2.5 Baths
    • 1,407 Sq Ft

    301 Orange Blossom Dr, Winter Haven, FL 33880

    ~Beautiful 3/2.5 Waters Edge Townhome Offered for Sale~Nestled within the Water’s Edge Community, located between Lake Lulu and Lake Roy in Winter Haven Florida, this townhome offers endless recreational opportunities from an exquisitely designed home. Features include a neutral color scheme, renovated kitchen with plenty of cabinet space and a convenient pass-through/bar area leading to an

    Michael Jimenez HOUSE OF GLASS REAL ESTATE PM

    301 Orange Blossom Dr, Winter Haven, FL 33880
  • /51

    $15,000

    • 2 Beds
    • 1 Bath
    • 672 Sq Ft

    317 Jupiter Ave, Winter Haven, FL 33884

    WELCOME HOME TO THIS BEAUTIFULLY UPGRADED 2-BEDROOM, 1-BATHROOM. Combining modern comfort and thoughtful features. The home shines with all-new double-pane windows, which boost energy efficiency. Wide, comfortable front steps welcome you inside, where fresh vinyl plank flooring creates a clean, contemporary feel. In 2024, the roof was sealed with a Cool Seal coating. The kitchen has been updated

    Whitney Campbell-Conkey Pelican's Nest Mobile Home Sales, LLC.

    317 Jupiter Ave, Winter Haven, FL 33884
  • /31

    $295,000

    • 2 Beds
    • 2 Baths
    • 1,691 Sq Ft

    1452 Grand Cayman Cir, Winter Haven, FL 33884

    PRICE REDUCTION!! Discover this stunning lakefront gem on Lake Dexter—a peaceful 166-acre lake in southeast Winter Haven, accessible only through private community ramps. Perfect for fishing, waterskiing, or simply cruising, Lake Dexter has something for everyone.Located in the highly sought-after Lake Dexter Moorings Community, residents enjoy a sparkling community pool and private boat

    Tomi Miller-Troupe COLDWELL BANKER REALTY

    1452 Grand Cayman Cir, Winter Haven, FL 33884
  • /34

    $184,947

    • 2 Beds
    • 1.5 Baths
    • 1,332 Sq Ft

    5850 Cypress Gardens Blvd Unit 304, Winter Haven, FL 33884

    Welcome to your new home located directly across the street From Legoland. Home features community pool and tennis court and is ready for a new owner. Located in the central Hub of Winter Haven and close to anything any everything you need. Shopping, restaurants, schools.

    Matthew Davis FLORIDA HOMES REALTY & MTG

    5850 Cypress Gardens Blvd Unit 304, Winter Haven, FL 33884
  • /44

    $227,000

    • 2 Beds
    • 2 Baths
    • 1,231 Sq Ft

    1561 Vienna Square Dr, Winter Haven, FL 33884

    R E D U C E D ... YOU'LL LOVE THIS MAINTENANCE FREE LIFESTYLE IN DESIREABLE VIENNA SQUARE , LOCATED IN WINTER HAVEN. THIS VILLA IS MOVE IN READY. THIS 2BR-2BA VILLA OFFERS AN OPEN GREAT ROOM DESIGN WITH SPLIT BEDROOMS. THE MASTER ENSUITE HAS WALK IN CLOSET WITH STEP IN SHOWER FOR CONVENIENCE. THE 2ND BEDROOM OFF FRONT ENTRANCE OF HOME HAS AN ADJOINING BATH WITH TUB AND SHOWER. DON'T WAIT,

    Glenda Pruitt FLORIDA HOME CHOICE REALTY

    1561 Vienna Square Dr, Winter Haven, FL 33884

Home Trends in Cypress Gardens, FL

Housing Trends

Median Sale Price
$404,990
Median Single Family Sale Price
$364,995
Average Price Per Sq Ft
$189
Number of Homes for Sale
3
Last 12 months Home Sales
1
Months of Supply
36.00
Median List Price
$377,500
Median Change From 1st List Price
10%
Median Home Sale Price YoY Change
20%
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