Winter Haven, FL Homes for Sale with Pool

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  $59,900

  • 2 Beds
  • 2 Baths

  83 Stebbins Dr Unit 43, Winter Haven, FL 33884

  Gabriel Dumeng AMAZING MOBILE HOMES LLC

  83 Stebbins Dr Unit 43, Winter Haven, FL 33884
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  $140,000

  $25K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,008 Sq Ft

  345 24th St NW Unit 25, Winter Haven, FL 33880

  Welcome to maintenance-free living in the heart of Winter Haven! This darling 2-bedroom, 2-bath villa is perfectly located in the desirable Imperial Villas a 55+ residential community, sitting within a short walking distance to beautiful Lake Howard. Inside, you’ll find updated flooring throughout and both bathrooms tastefully renovated, giving the home a fresh, move-in-ready feel. The open

  Michele Elchin DALTON WADE INC

  345 24th St NW Unit 25, Winter Haven, FL 33880
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  $99,990

  $20K PRICE DROP

  • 2 Beds
  • 2 Baths

  21 Key West Ave, Winter Haven, FL 33880

  A Must See well-maintained 2 Bedroom / 2 Bath - 2025 Build in Shipp Reck 55+ Community. Welcome to easy Florida living in the desirable Shipp Reck community in Winter Haven, Florida. This beautiful 2025-built home with only one owner features 2 bedrooms and 2 bathrooms and comes fully furnished making it move-in ready, the perfect seasonal getaway or full-time residence. Step inside to an open

  Linda Wilson Sunset Home Sales

  21 Key West Ave, Winter Haven, FL 33880
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  $765,000

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,678 Sq Ft

  3831 Gaines Dr, Winter Haven, FL 33884

  Welcome to this immaculate dream home at 3831 Gaines Dr!This beautifully updated 3-bedroom + office home features an open floor plan with stunning upgrades throughout, including an updated kitchen, modern bathrooms, and spacious living areas designed for both comfort and entertaining. The gorgeous kitchen is complete with brand-new appliances and flows seamlessly into the main living

  Vikki Thielen THE MARKET REALTY COMPANY

  3831 Gaines Dr, Winter Haven, FL 33884
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  $256,900

  $35K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,506 Sq Ft

  909 Cambridge Dr, Winter Haven, FL 33881

  Short Sale. – PRICED TO SELL! Welcome to this 2022-built 3-bedroom, 2-bathroom home located in the growing Lucerne Park Reserve community of Winter Haven. This newer construction single-story home features a desirable open-concept floor plan, perfect for comfortable everyday living and easy entertaining. The spacious kitchen overlooks the living and dining areas, creating a bright and inviting

  Mariel Espinal LPT REALTY, LLC

  909 Cambridge Dr, Winter Haven, FL 33881
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  $394,000

  $31K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,263 Sq Ft

  239 Golf Aire Blvd, Winter Haven, FL 33884

  PRICE IMPROVEMENT OF $5K MOTIVATED SELLERBEAUTIFUL GATED GOLF COURSE COMMUNITYAn exceptional opportunity to own a beautiful 3brm/2.5 bath home nestled on the 4th hole of the highly sought-after Lake Bess Country Club and Golf Course in Winter Haven. As you step inside, you are welcomed by a charming foyer featuring 10-ft ceilings that create an open and airy ambiance throughout the home.

  Christina Ashley DALTON WADE INC

  239 Golf Aire Blvd, Winter Haven, FL 33884
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  $187,900

  $21K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,458 Sq Ft

  1012 Medinah Dr, Winter Haven, FL 33884

  NOW OFFERING A HOME WARRANTY! Your opportunity to own in the highly sought-after Cypresswood Golf & Country Club just became even more appealing. Welcome to The Tennis Villas, where gated security, resort-style amenities, and maintenance-friendly living come together in one of Central Florida’s premier golf communities. A charming wrought iron gate welcomes you into a private front courtyard

  Corinna Weaver CROSBY & ASSOCIATES, INC.

  1012 Medinah Dr, Winter Haven, FL 33884
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  $179,000

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

  332 Siberian Cypress Cir, Winter Haven, FL 33881

  $632 LOT RENT! Welcome home to Cypress Creek Village in Winter Haven, Florida! This beautifully designed 2022 ScotBilt home offers the perfect blend of comfort, space, and resort-style living in one of Winter Haven's sought-after 55+ gated communities. Featuring 3 bedrooms, 3 bathrooms, and 1749 square feet of living space, this home was built for easy living and entertaining. Step inside to an

  Daniel Butler Sun Realty of Florida

  332 Siberian Cypress Cir, Winter Haven, FL 33881
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  /25

  $287,990

  New Construction $8K PRICE INCREASE

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

  4129 Giorgio Dr, Winter Haven, FL 33884

  Under Construction. This BEAUTIFUL ALLEX II Model home is located in the quaint town of Winter Haven. Ski capital & home of LEGOLAND. The ALLEX II is3/2/2- 1504 S/F & newly upgraded! This new model has an open floor plan with a spacious DINING room off the kitchen to entertain & enjoy the company of your guests. You will love the split floor plan with beautiful & spacious master suite with walk

  Paul King DR HORTON REALTY OF CENTRAL FLORIDA LLC

  4129 Giorgio Dr, Winter Haven, FL 33884
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  $229,900

  $8K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,651 Sq Ft

  381 San Jose Dr, Winter Haven, FL 33884

  Welcome to this wonderful 3 bedroom, 2 bathroom home located on a spacious corner lot with NO rear neighbors in the desirable Orchid Springs community in SE Winter Haven. NEW METAL ROOF PUT ON IN 2021 AND AC REPLACED IN 2023! Offering a versatile split-bedroom floor plan, this home features a living room, dining room and family room, providing plenty of space for both everyday living and

  Patricia de Graaff RE/MAX HERITAGE PROFESSIONALS

  381 San Jose Dr, Winter Haven, FL 33884
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  $129,000

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

  4132 Sprucewood St, Winter Haven, FL 33880

  Location! Location! Location! This beautiful fully furnished home in Oakwood Estates is located next to the pool, tennis courts, and smaller clubhouse. Walk into the lanai as you enter the home. Once inside the home you will find a cozy family room and an open and and appealing kitchen just perfect for entertaining. The living room beyond the kitchen is open and spacious. The refrigerator was new

  Kathy Devor COLDWELL BANKER REALTY

  4132 Sprucewood St, Winter Haven, FL 33880
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  $350,990

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,308 Sq Ft

  1734 Hummingbird Rd, Winter Haven, FL 33884

  Under Construction. Welcome to the Campbell, a stunning four-bedroom, two and a half bathroom home located in the heart of Winter Haven, Florida at our Harmony at Lake Eloise community. A beautiful patio welcomes you to a home that optimizes living space with an open concept kitchen overlooking the living area, dining room, and outdoor lanai. Entertaining is a breeze, as this popular

  Paul King DR HORTON REALTY OF CENTRAL FLORIDA LLC

  1734 Hummingbird Rd, Winter Haven, FL 33884
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  $385,000

  $25K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,356 Sq Ft

  136 Lake Mariam Rd, Winter Haven, FL 33884

  *NEW-PRICE REDUCTION in a classic Winter Haven Community-Beautiful Home!**NEW ROOF 2026 * NEW INSULATION 2026 * NEW HOT WATER HEATER 2026* NEWER AIR CONDITIONER 2020*Welcome to the classic neighborhood of Lakewood, located in Southeast Winter Haven. This spacious 4 bedroom, 3 bath home, & with the additional 4th bedroom it offers versatility, including a closet, private sliding door

  Jill Baird KELLER WILLIAMS ADVANTAGE III

  136 Lake Mariam Rd, Winter Haven, FL 33884
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  $380,000

  $45K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 2,696 Sq Ft

  1328 Daisy Field Dr, Winter Haven, FL 33884

  HUGE $45,000 PRICE DROP! Welcome to one of the largest homes in the desirable Harmony Lake Eloise community! This spacious 5-bedroom, 3-bathroom residence offers a versatile and thoughtfully designed layout perfect for modern living. A generously sized flex room—currently used as a dining area—can easily be converted into a 6th bedroom, home office, or bonus space to suit your needs. The spacious

  David Small KELLER WILLIAMS REALTY SMART 1

  1328 Daisy Field Dr, Winter Haven, FL 33884
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  /19

  $249,900

  $13K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,426 Sq Ft

  297 Meadowbrook Blvd, Winter Haven, FL 33881

  Welcome to 297 Meadowbrook Boulevard, a well-maintained 3-bedroom, 2-bathroom home located in the Lucerne Park Reserve community of Winter Haven. Built in 2020, this single-story residence offers approximately 1,408 square feet of comfortable living space with a functional, open-concept floor plan designed for everyday living and entertaining. The kitchen flows seamlessly into the main living and

  Karina Alfonso LPT REALTY, LLC

  297 Meadowbrook Blvd, Winter Haven, FL 33881
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  $315,000

  $10K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,038 Sq Ft

  1670 17th St NW, Winter Haven, FL 33881

  BACK ON THE MARKET!! Winter Haven Chain of Lakes Home! Needs updating and repairs but this could be your paradise on Lake Mirror! This charming 2-bedroom, 1-bathroom home offers a unique blend of tranquility and recreation, creating a haven for those seeking the perfect retreat. Nestled on the shores of the picturesque Lake Mirror, this property is a true gem. Imagine waking up to breathtaking

  Lori Edwards COLDWELL BANKER REALTY

  1670 17th St NW, Winter Haven, FL 33881
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  $119,900

  • 2 Beds
  • 2 Baths
  • 1,404 Sq Ft

  2309 Prestwick Place Unit 313, Winter Haven, FL 33881

  2 Bedroom| 2 Bath | 1,404 sq. ft. | $119,900 Four Lakes Golf Club Lot 313 Welcome to resort-style living at Four Lakes Golf Club! This beautifully maintained manufactured home offers 1,404 sq. ft. of comfortable living space with stunning sunset water views overlooking the golf course and ponds. This fully furnished, turnkey home is move-in ready and packed with upgrades and extras. Step inside

  Cheryl Dobbs CRF Communities

  2309 Prestwick Place Unit 313, Winter Haven, FL 33881
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  /50

  $92,900

  $11K PRICE DROP

  • 2 Beds
  • 2 Baths

  1765 Glen Abby Ln Unit 738, Winter Haven, FL 33881

  This 2 Bedroom/2 Bath listed at $92,900 is located on a large corner lot, fully furnished and is ready for you to move in and take advantage of all that Four Lakes Golf Club community has to offer. This home includes many updates including new A/C unit in 2025, carport replacement 2024, updated appliances, in home washer/dryer, whole house air filtration and 4 passenger electric golf cart. The

  Deb Bartholomew Sunset Home Sales

  1765 Glen Abby Ln Unit 738, Winter Haven, FL 33881
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  $74,900

  • 2 Beds
  • 2 Baths
  • 1,159 Sq Ft

  1051 La Costa Ln Unit 116, Winter Haven, FL 33881

  This beautifully maintained 2‑bedroom, 2‑bath Jacobsen home offers 1,159 sq. ft. of immaculate living space in the highly desirable Four Lakes Golf Club community. The home features plantation shutters, six‑panel doors, and tasteful décor throughout. A large glass lanai welcomes you at the front of the home, providing a bright and relaxing space to enjoy Florida's sunshine. The decorator driveway

  Cheryl Dobbs CRF Communities

  1051 La Costa Ln Unit 116, Winter Haven, FL 33881
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  $190,000

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

  6229 Knotty Pine Dr SE, Winter Haven, FL 33884

  Beautifully Maintained Home in a Fun 55+ CommunityWelcome home to this beautifully maintained 3-bedroom, 2-bath home located in a well-established 55+ community where neighbors become friends and there is always something fun happening! Residents enjoy a lively social atmosphere with community gatherings, planned outings, and plenty of opportunities to get out, meet your neighbors, and

  Stacey Payne PREFERRED REAL ESTATE BROKERS

  6229 Knotty Pine Dr SE, Winter Haven, FL 33884

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