Winter Haven, FL Homes

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  /50

  $253,900

  • 3 Beds
  • 1 Bath
  • 1,264 Sq Ft

  222 5th St, Winter Haven, FL 33880

  LARGE WORKSHOP - NO HOA -ELECTRIC BILLS UNDER $75.00 PER MONTH - This home has lots to offer. The back yard is totally fenced with two large gates on either side. This three bedroom one bath has new double pane windows that were installed in 2024. The cozy eat-in kitchen has warm colored wood cabinets. All appliances including the washer and dryer will remain with the home. There are two bonus

  

  Brenda J. Quinn

  QUINN & COMPANY REALTORS, LLC

  (863) 329-5409

  222 5th St, Winter Haven, FL 33880
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  /32

  $1,500 - $2,050 per month

  Lakeshore Club

  1 - 3 Beds

  1300 Lake Howard Dr SW, Winter Haven, FL 33880

  Welcome to luxury living in Winter Haven. Lakeshore Club is located on the Chain of Lakes between Lake Howard and Lake Mary minutes from downtown Winter Haven.

  1300 Lake Howard Dr SW, Winter Haven, FL 33880
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  $282,990 Sold Apr 24, 2025

  3440 Costello Cir, Winter Haven, FL 33884

  • 4 Beds
  • 2 Baths
  • 1,665 Sq Ft
  • Built 2025

  Last Sold Summary

  • 4% Below List Price
  • $170/SF
  • 52 Days On Market

  Current Estimated Value $280,909

  Last Listing Agent Paul King DR HORTON REALTY OF CENTRAL FLORIDA LLC

  3440 Costello Cir, Winter Haven, FL 33884
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  /44

  Est $300,981 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,842 Sq Ft

  7146 Summit Dr, Winter Haven, FL 33884

  7146 Summit Dr, Winter Haven, FL 33884
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  /43

  $375,000

  • 4 Beds
  • 3 Baths
  • 1,772 Sq Ft

  317 26th St SW, Winter Haven, FL 33880

  Welcome to this spacious and inviting 4-bedroom, 3 full-bath home, perfectly situated on more than one acre of land. Offering the best of comfort and privacy, this property is ideal for families, entertainers, or anyone looking to enjoy peaceful living with plenty of room to grow.Inside, you’ll find an open and functional layout with generously sized bedrooms, a bright kitchen, and

  Edward Tejada

  R&J REALTY AND PROPERTY MANAGEMENT LLC

  (863) 323-8452

  317 26th St SW, Winter Haven, FL 33880
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  /21

  $1,650 per month

  • 2 Beds
  • 2 Baths
  • 1,190 Sq Ft
  • Condo for Rent

  700 Mirror Terrace NW, Winter Haven, FL 33881

  Million dollar view overlooking the Winter Haven Chain of Lakes (17 connected lakes). Situated along the south shore of Lake Spring. Its the best maintained building in Winter Haven and likely the entire of Polk County. Brand new completely remodeled unit. Never lived in since refurbishment. New air conditioning system. 1-assigned covered parking space. Assigned storage locker on your floor.

  Scott Kline Kline Real Estate Services

  700 Mirror Terrace NW, Winter Haven, FL 33881
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  /2

  $267,900 Sold Aug 17, 2025

  2021 Oliver Place, Winter Haven, FL 33881

  • 3 Beds
  • 2 Baths
  • 1,627 Sq Ft
  • Built 1967

  Last Sold Summary

  • 1% Below List Price
  • $165/SF
  • 21 Days On Market

  Current Estimated Value $266,158

  Last Listing Agent Glen Barron C BUDDY JOHNSON REALTY, LLC

  2021 Oliver Place, Winter Haven, FL 33881
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  /32

  Est $280,172 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,993 Sq Ft

  1920 Bretton Ridge Dr, Winter Haven, FL 33884

  1920 Bretton Ridge Dr, Winter Haven, FL 33884
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  /19

  $468,000

  • 3 Beds
  • 2 Baths
  • 1,680 Sq Ft

  10 Jimmy Lee Rd, Winter Haven, FL 33880

  Experience the best of both worlds — peaceful country living just minutes from town! Tucked away on a quiet street, this beautifully updated home sits on over 2.3 fully fenced, irrigated acres, offering the perfect blend of space, privacy, and convenience. Whether you’re dreaming of a small hobby farm, a garden paradise, or simply room to roam, this property delivers.Step inside to a warm and

  

  Michelle Howard

  KELLER WILLIAMS REALTY SMART 1

  (863) 450-1738

  10 Jimmy Lee Rd, Winter Haven, FL 33880
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  /14

  $1,300 - $1,825 per month

  The Arbours at Garden Grove

  1 - 3 Beds

  4900 Cypress Gardens Rd, Winter Haven, FL 33884

  A variety of spacious and inviting floor plans await you at Arbours at Garden Grove. Choose from one of our three floor plans offering one, two and three bedrooms, designed with your comfort in mind. Enjoy an assortment of amenities such as vaulted ceilings, a wet bar, air conditioning and double vanities to name a few! The Arbours at Garden Grove amenities extend far beyond your doorstep. Take a

  4900 Cypress Gardens Rd, Winter Haven, FL 33884
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  /2

  $120,000 Sold Mar 31, 2025

  504 Sears Ave NE, Winter Haven, FL 33881

  • 2 Beds
  • 1 Bath
  • 955 Sq Ft
  • Built 1955

  Last Sold Summary

  • 4% Below List Price
  • $126/SF
  • 4 Days On Market

  Current Estimated Value $120,195

  Last Listing Agent Matt Helmling BAY VISION REALTY INC

  504 Sears Ave NE, Winter Haven, FL 33881
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  /45

  Est $336,893 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,873 Sq Ft

  3655 Plymouth Dr, Winter Haven, FL 33884

  3655 Plymouth Dr, Winter Haven, FL 33884
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  /16

  $120,000

  • 2 Beds
  • 1.5 Baths
  • 851 Sq Ft

  831 Orchid Springs Dr Unit 831, Winter Haven, FL 33884

  Whether you are looking for your first home or first rental property, this condominium is a must see! Ideally located off of Overlook Drive in Winter Haven, minutes form Legoland, downtown Winter Haven, and the Chain of Lakes. This unit features an updated kitchen with an upgraded stainless steel gas stove, stainless steel dish washer, and a one-year-old refrigerator. Additionally, there are

  

  Steven Perkins

  CLARK REALTY LLC

  (863) 312-1266

  831 Orchid Springs Dr Unit 831, Winter Haven, FL 33884
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  /28

  $1,400 per month

  • 2 Beds
  • 2 Baths
  • 1,017 Sq Ft
  • Condo for Rent

  1401 Eagle Pond Dr Unit 14A, Winter Haven, FL 33884

  This 2 Bedroom / 2 Bathroom condominium in Cypresswood is now available! First floor unit provides easy access! Cypresswood is a gated golf course community with a guarded gate at the entrance of the community. Access to the community pool and tennis courts is included! Schedule a showing today!

  Bobby DeSanto LOCKHART & ASSOCIATES INC

  1401 Eagle Pond Dr Unit 14A, Winter Haven, FL 33884
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  /2

  $395,000 Sold May 14, 2025

  410 Majestic Gardens Blvd, Winter Haven, FL 33880

  • 3 Beds
  • 2.5 Baths
  • 2,094 Sq Ft
  • Built 2006

  Last Sold Summary

  • $189/SF
  • 26 Days On Market

  Current Estimated Value $379,706

  Last Listing Agent Geraldine Anarumo FLORIDA REALTY MARKETPLACE

  410 Majestic Gardens Blvd, Winter Haven, FL 33880
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  /12

  Est $295,804 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,748 Sq Ft

  2189 Rose Blvd, Winter Haven, FL 33881

  2189 Rose Blvd, Winter Haven, FL 33881
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  /19

  $149,000

  • 3 Beds
  • 1 Bath
  • 1,339 Sq Ft

  3462 Avenue T NW, Winter Haven, FL 33881

  PRICE REDUCED!! Charming three-bedroom, one-bath home located in NW Winter Haven. This property features wood laminate flooring throughout, with carpet in two of the bedrooms. Recent updates include a new water heater (2023), replumbing (2024), and a brand-new septic system (2025). Living room with fireplace and separate formal dining room. The A/C unit is just five years old, providing peace of

  

  Amy Reynolds

  LOCKHART & ASSOCIATES INC

  (863) 343-2894

  3462 Avenue T NW, Winter Haven, FL 33881
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  /14

  $1,000 - $1,275 per month

  Central Haven Apartments

  Studio - 2 Beds

  130 Avenue C SE, Winter Haven, FL 33880

  130 Avenue C SE, Winter Haven, FL 33880
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  /16

  $279,304 Sold Oct 08, 2025

  • 1,487 Sq Ft
  • $188/SF

  • 3 Beds
  • 2 Baths
  • Built 2025

  2126 Chris Dr, Winter Haven, FL 33884

  This new single-story home maximizes space and emphasizes convenience. The open-concept layout integrates the family room, dining room and kitchen with a central island, facilitating effortless transitions between rooms for easy entertaining during gatherings. On the opposite side of the home are all three bedrooms, including the peaceful owner’s suite with an attached bathroom and walk-in closet.

  Lennar

  2126 Chris Dr, Winter Haven, FL 33884
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  /24

  Est $291,279 Not Listed For Sale

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

  184 Fall Glo Rd, Winter Haven, FL 33880

  184 Fall Glo Rd, Winter Haven, FL 33880
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  /10

  $199,900

  • 3 Beds
  • 1 Bath
  • 1,210 Sq Ft

  118 Orange Ave, Winter Haven, FL 33880

  BACK ON THE MARKET! INVESTORS SPECIAL! HANDYMAN SPECIAL! This cozy home is located just minutes from downtown Winter Haven. This cute home boast a 3 bedroom, 1 bath in the main house with screened in patio in the rear and two carports for parking currently rented under market rate. An additional highlight of this home is the de-attached 1br/1ba or mother-in-law suite, which includes a separate

  

  Sam Pergerson

  COLDWELL BANKER REALTY

  (863) 900-8957

  118 Orange Ave, Winter Haven, FL 33880
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  /9

  $950 per month

  • 1 Bed
  • 1 Bath
  • 600 Sq Ft
  • Apartment for Rent

  2924 Whispering Trails Dr, Winter Haven, FL 33884

  Some pictures are virtual furniture. IMPORTANT IS STUDIO NO THE ALL-HOUSE Modern Studio 1-Bedroom, 1 bath rental, – All Utilities Included! This Next Gen-style unit features a private entrance, walking closet, private screen porch, small kitchen, laundry, and private parking. Enjoy A/C, high-speed internet, electricity, water, trash, channel and yard care—all included in rent. Located in a quiet

  maritza monzon INTERNATIONAL EXECUTIVE REALTY

  2924 Whispering Trails Dr, Winter Haven, FL 33884
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  /2

  $270,000 Sold Apr 25, 2025

  3272 Whispering Trails Ave, Winter Haven, FL 33884

  • 3 Beds
  • 2 Baths
  • 1,533 Sq Ft
  • Built 2016

  Last Sold Summary

  • 4% Below List Price
  • $176/SF
  • 35 Days On Market

  Current Estimated Value $268,124

  Last Listing Agent Troy Udit ENGEL & VOLKERS ORLANDO DR PHILLIPS

  3272 Whispering Trails Ave, Winter Haven, FL 33884
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  /24

  Est $322,599 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,090 Sq Ft

  2899 Eagle Nest View Dr, Winter Haven, FL 33881

  2899 Eagle Nest View Dr, Winter Haven, FL 33881
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  /45

  $257,000 Pending

  • 4 Beds
  • 2 Baths
  • 1,753 Sq Ft

  94 Saint Kitts Cir, Winter Haven, FL 33884

  Under contract-accepting backup offers. Welcome home to this spacious 4-bedroom, 2-bath residence located in Planters Walk. This home offers 1,753 sq. ft. of comfortable living in Southeast Winter Haven. Newer A/C, the Roof is only 4 years old! LVP flooring and the laundry room is located inside. The kitchen features a bright breakfast/dining area and opens to the main living space—perfect for

  

  Brad Martin

  BETTER HOMES AND GARDENS REAL ESTATE LIFESTYLES REALTY

  (863) 310-1728

  94 Saint Kitts Cir, Winter Haven, FL 33884
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  /29

  $876 - $1,019 per month

  Villas at Lake Smart Apartments

  2 - 3 Beds

  4225 Vista Del Lago Dr, Winter Haven, FL 33881

  You've found your slice of paradise at Villas at Lake Smart in sunny Winter Haven, FL! Our spacious and affordable two and three-bedroom apartment homes offer the perfect sanctuary for you to unwind after a long day. Ensuring you don't have to go far for fun and fitness, our community features a volleyball court, playground, fitness center, clubhouse, pool, and more! Looking for some

  4225 Vista Del Lago Dr, Winter Haven, FL 33881
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  /2

  $315,000 Sold Dec 26, 2024

  326 Niblick Cir, Winter Haven, FL 33881

  • 3 Beds
  • 2 Baths
  • 2,176 Sq Ft
  • Built 2004

  Last Sold Summary

  • 20% Below List Price
  • $145/SF
  • 200 Days On Market

  Current Estimated Value $324,738

  Last Listing Agent Chad Lindsey LOKATION

  326 Niblick Cir, Winter Haven, FL 33881
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  /52

  Est $326,221 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,526 Sq Ft

  208 Fall Glo Rd, Winter Haven, FL 33880

  208 Fall Glo Rd, Winter Haven, FL 33880
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  /29

  $299,900

  • 3 Beds
  • 2 Baths
  • 1,860 Sq Ft

  880 Oleander Dr SE, Winter Haven, FL 33880

  Welcome to this inviting 3 bedroom, 2 bath home with 1,860 sqft of living space in one of Southeast Winter Haven’s desirable neighborhoods. Enjoy a spacious family room surrounded by large glass windows on three sides, flooding the home with natural light and providing a perfect spot to relax or entertain. The cozy living room features a fireplace with built-in bookshelves, creating a warm and

  

  Steve Lockhart

  LOCKHART & ASSOCIATES INC

  (863) 591-6496

  880 Oleander Dr SE, Winter Haven, FL 33880
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  /8

  $850 per month

  • 2 Beds
  • 2 Baths
  • 1,100 Sq Ft
  • House for Rent

  100 4th St, Winter Haven, FL 33880

  Rent with confidence from a licensed Real Estate Brokerage. We have a quick and simple application process. WE PROUDLY WELCOME ALL PETS. Contact us through this Web site or call to set up a tour and apply today! Welcome to this cute 2 bed, 2 bath home! Our spacious layout is perfect for comfortable living. Enjoy the yard to unwind after a long day, enjoy the fresh air, and gather for fun-filled

  Erich Spivey ALABAMA LLC

  100 4th St, Winter Haven, FL 33880
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  /2

  $290,000 Sold Nov 26, 2025

  1480 Leamington Ln, Winter Haven, FL 33884

  • 4 Beds
  • 2.5 Baths
  • 2,202 Sq Ft
  • Built 2024

  Last Sold Summary

  • 17% Below List Price
  • $132/SF
  • 402 Days On Market

  Last Listing Agent Claudia Gutierrez ADAMS HOMES REALTY

  1480 Leamington Ln, Winter Haven, FL 33884
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  /18

  Est $329,291 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,505 Sq Ft

  4253 Roberta Dr, Winter Haven, FL 33881

  4253 Roberta Dr, Winter Haven, FL 33881
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  /20

  $249,000

  • 3 Beds
  • 2 Baths
  • 1,238 Sq Ft

  1109 5th St SW, Winter Haven, FL 33880

  Discover the exceptional potential of this 3-bedroom, 2-bathroom home ideally located in the heart of Winter Haven, offering unbeatable access and flexibility with no HOA restrictions. Positioned just minutes from major highways, shopping centers, dining, and local amenities, this property delivers convenience that’s hard to match. Inside, the home features a spacious living area, an updated

  

  Carlos DeJesus

  EXIT REALTY 4CORNERS

  (863) 267-9625

  1109 5th St SW, Winter Haven, FL 33880
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  /11

  $1,250 - $1,350 per month

  Lake Buckeye Apartments

  1 - 2 Beds

  101 Parker Ln NE, Winter Haven, FL 33881

  Call for availability! Our apartment complex is nestled back in a residential housing lakeside community, away from busy traffic. Quiet surroundings for families and single professionals to relax in their home. We provide high tech security cameras throughout the whole complex to assure your safety. Lake Buckeye owners want to provide a drug-free and safe environment for your family to call

  101 Parker Ln NE, Winter Haven, FL 33881
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  /2

  $299,800 Sold Aug 15, 2025

  2159 Greenway Dr, Winter Haven, FL 33881

  • 4 Beds
  • 3 Baths
  • 2,030 Sq Ft
  • Built 1971

  Last Sold Summary

  • 8% Below List Price
  • $148/SF
  • 15 Days On Market

  Current Estimated Value $296,711

  Last Listing Agent David Small KELLER WILLIAMS REALTY SMART 1

  2159 Greenway Dr, Winter Haven, FL 33881
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  /34

  Est $290,089 Not Listed For Sale

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

  3034 Royal Tern Dr, Winter Haven, FL 33881

  3034 Royal Tern Dr, Winter Haven, FL 33881
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  /24

  $375,000

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

  814 Turner Ln, Winter Haven, FL 33881

  Welcome to 814 Turner Lane, a beautifully upgraded Hayden model by D.R. Horton located in the heart of Winter Haven! ?? This spacious two-story home offers 5 bedrooms, 3 full bathrooms, and over 2,500 sq. ft. of living space, making it the perfect choice for families or anyone seeking extra room to spread out. Built with quality craftsmanship and thoughtful design, the Hayden model is known for

  

  Rafael Ortiz

  KELLER WILLIAMS LEGACY REALTY

  (863) 375-8538

  814 Turner Ln, Winter Haven, FL 33881
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  /10

  $1,100 per month

  • 1 Bed
  • 1 Bath
  • 680 Sq Ft
  • Apartment for Rent

  2824 Avenue G NW, Winter Haven, FL 33880

  1 bedroom 1 bath apartment. Beautifully updated apartment home with all ceramic tile, newer cabinets and appliances. Home overlooks Deer Lake. Large backyard with lawn care included. This unit is the right hand side of the home. Separate 3 bedroom home is on the left side.

  Kara Severit REMAX EXPERTS

  2824 Avenue G NW, Winter Haven, FL 33880
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  /2

  $282,990 Sold Jun 18, 2025

  3479 Costello Cir, Winter Haven, FL 33884

  • 4 Beds
  • 2 Baths
  • 1,665 Sq Ft
  • Built 2024

  Last Sold Summary

  • $170/SF
  • 4 Days On Market

  Current Estimated Value $281,646

  Last Listing Agent Paul King DR HORTON REALTY OF CENTRAL FLORIDA LLC

  3479 Costello Cir, Winter Haven, FL 33884
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  /17

  Est $218,759 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,521 Sq Ft

  3004 Caneel St, Winter Haven, FL 33884

  3004 Caneel St, Winter Haven, FL 33884

Showing Results 161 - 200, Page 5 of 18