Winter Haven, FL Homes for Sale with Pool

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  $559,000

  • 4 Beds
  • 2.5 Baths
  • 3,114 Sq Ft

  725 Heritage Dr NE, Winter Haven, FL 33881

  One or more photo(s) has been virtually staged. Located in the desirable Hamilton Pointe community, this beautifully maintained 4-bedroom, 2.5-bath, 3,114 sf poolhome built in 1992, sits on a half-acre lot with no rear neighbors offering peaceful views of a protected conservationarea and ultimate backyard privacy. Features include a spacious kitchen with eat-in area and French doors to

  Laura Slocumb REMAX EXPERTS

  725 Heritage Dr NE, Winter Haven, FL 33881
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  $154,900

  $15K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,044 Sq Ft

  39 Kimberly Ct, Winter Haven, FL 33880

  Welcome to Brandy Chase Village!! This well desired 55+ community located in Winter Haven Florida is centrally located between Tampa and Orlando. The beautiful 2 bedroom and 2 bathroom home is well maintained and ready for you! Enjoy your oversized sunroom that adds extra square footage of living space for you to enjoy. Updated appliances and a new AC was installed in 2021 , as well as it was

  Rosalia Abreu ALLSTATE REALTY SERVICES

  39 Kimberly Ct, Winter Haven, FL 33880
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  /20

  $109,000

  $7K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,286 Sq Ft

  2909 Shoal Creek Place Unit 798, Winter Haven, FL 33881

  3 Bedroom | 2 Bath | 1,286 sq ft | $109,000 Four Lakes Golf Club Lot 798 PRICE REDUCED FROM $116,000 TO $109,000! Welcome to your move-in-ready home: Four Lakes Lot 798! This 3 bedroom, 2 bath doublewide boasts a unique split floor plan complete with office, pass-through kitchen, and Florida Room. Step into the freshly painted main living area, which feels warm and inviting. The living room flows

  Cheryl Dobbs CRF Communities

  2909 Shoal Creek Place Unit 798, Winter Haven, FL 33881
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  $420,104

  New Construction

  • 5 Beds
  • 3.5 Baths
  • 3,030 Sq Ft

  5110 Kinsley Dr, Lake Wales, FL 33859

  Under Construction. The main floor of the inviting Ammolite plan offers a private study and versatile flex space, which can be optioned as an additional bedroom and bathroom or a guest suite, complete with living room. You’ll also appreciate a convenient powder room; a nook; a great room and a well-appointed kitchen with a center island, a large pantry and optional additional cabinets. Upstairs,

  Stephanie Morales AXEN REALTY, LLC

  5110 Kinsley Dr, Lake Wales, FL 33859
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  $308,915

  New Construction $6K PRICE INCREASE

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

  5139 Kinsley Dr, Lake Wales, FL 33859

  Discover this exciting Azure home. Included features: an inviting covered entry; a thoughtfully designed kitchen offering quartz countertops, 42 white cabinets, stainless-steel appliances, a walk-in pantry and a center island; an elegant dining room; a large great room; a beautiful primary suite showcasing a spacious walk-in closet and a private bath; a convenient laundry; a mudroom and a covered

  Richmond American Homes Builder

  5139 Kinsley Dr, Lake Wales, FL 33859
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  /20

  $116,500

  $3K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,030 Sq Ft

  333 Lake Howard Dr NW Unit 103C, Winter Haven, FL 33880

  Welcome to 333 Lake Howard Drive – a bright and spacious 2 bedroom, 2-bath unit condo in the desirable Imperial Harbours 55+ lakefront community in Winter Haven. This unit has ample natural light, This well-maintained condo offers an open living and dining area, charming kitchen, primary suite offers a walk-in closet, in-unit laundry, Imperial Harbours offers more than just a home – it’s a

  Kevin Tison LPT REALTY, LLC

  333 Lake Howard Dr NW Unit 103C, Winter Haven, FL 33880
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  /21

  $22,900

  $2K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 672 Sq Ft

  139 Jay Dr, Winter Haven, FL 33880

  Affordable living in Central Florida makes your dream life-style a reality! Welcome to this quaint and well-kept 2-bedroom 1.5-bath bungalow in a beautiful resort-style 55+ pet-friendly community in Winter Haven, Florida. This lovely home features several updates: New laminate flooring throughout, New kitchen and bathroom countertops, Fresh paint throughout, New washer and dryer, and a large

  Teresa Gago Sunset Home Sales

  139 Jay Dr, Winter Haven, FL 33880
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  $145,000

  $20K 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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  $110,000

  $10K 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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  $281,900

  $10K 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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  $187,900

  $21K PRICE DROP

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

  1012 Medinah Dr, Winter Haven, FL 33884

  Fresh new price — NOW OFFERING A HOME WARRANTY! Your opportunity to own in Cypresswood just got better! Welcome to The Tennis Villas! Nestled in the highly desired Cypresswood Golf & Country Club, this gated community with 24/7 security offers the perfect blend of comfort, convenience, and resort-style living.At the entry, a classic wrought iron gate opens to a private front patio, creating a

  Corinna Weaver CROSBY & ASSOCIATES, INC.

  1012 Medinah Dr, Winter Haven, FL 33884
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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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  $404,990

  New Construction $5K PRICE DROP

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

  2543 Sage Valley Way, Winter Haven, FL 33884

  The property is located at 2543 Sage Valley Way WINTER HAVEN FL 33884 priced at 404990, the square foot and stories are 2601, 2.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

  2543 Sage Valley Way, 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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  $157,500

  $18K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 781 Sq Ft

  7705 Waterview Way Unit 7705, Winter Haven, FL 33884

  Beautiful condo located in the Garden Villas section of the Winterset community. This property is perfect for the person looking for a maintenance free lifestyle and resort style of living. Winterset offers a full time secured gated entryway, community pool, clubhouse, tennis courts, and more. The community overlooks beautiful Lake Winterset. You will enjoy not having to worry about lawn

  Alexander Matos THE SOMERDAY GROUP PL

  7705 Waterview Way Unit 7705, 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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  $339,900

  • 3 Beds
  • 2 Baths
  • 1,867 Sq Ft

  153 Stevenson Rd, Winter Haven, FL 33884

  Fully furnished, move in ready pool home located in a quiet, established Winter Haven neighborhood just minutes from LEGOLAND Florida.Situated in a community known for long term ownership and pride of ownership, this property offers a peaceful setting with exceptional convenience and no HOA. A gated side entrance provides rare RV or boat parking, adding flexibility and value.The interior

  Dee Norris NEXTHOME NORRIS & COMPANY REAL

  153 Stevenson Rd, Winter Haven, FL 33884
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  $149,900

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,120 Sq Ft

  1728 Glen Abby Ln Unit 692, Winter Haven, FL 33881

  3 Bedrooms | 2 Bathrooms | 2,120 Sq. | $149,900 Four Lakes Golf Club Lot 692 Price just reduced from $159,900 to $149,900! Triple the Space. Triple the Views. Triple the WOW! Welcome to a rare and truly spectacular triple-wide home offering breathtaking golf course, water and sunset views-all wrapped into one turnkey, fully furnished retreat in Four Lakes Golf Club. With windows galore framing

  Cheryl Dobbs CRF Communities

  1728 Glen Abby Ln Unit 692, 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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