Winter Haven, FL Homes

• 

  

  

  /23

  $225,000

  • 2 Beds
  • 2 Baths
  • 1,419 Sq Ft

  2646 Rutledge Ct, Winter Haven, FL 33884

  Welcome to this beautifully maintained two-bedroom, two-bathroom townhome with a versatile flex space, perfectly situated in one of Winter Haven's most desirable communities. As you step inside, you’ll be greeted by soaring 16-foot ceilings, an open floor plan filled with natural light, and tasteful finishes that create an inviting atmosphere. Just off the entry, a spacious guest bedroom with an

  Nancy Lezotte KELLER WILLIAMS CLASSIC

  2646 Rutledge Ct, Winter Haven, FL 33884
• 

  

  

  /21

  $2,100 per month

  • 4 Beds
  • 2 Baths
  • 1,848 Sq Ft
  • House for Rent

  724 Grove St, Winter Haven, FL 33884

  Live in this beautiful brand-new single-family home located in the peaceful and growing community of Inman Grove in Winter Haven! 4 spacious bedrooms and 2 full bathrooms, 2-car garage. Modern open-concept kitchen and living area perfect for entertaining. Great backyard. SS appliances included (fridge, stove, microwave, dishwasher). Window blinds. Enjoy the comfort and convenience of living in a

  Jose Virguez Keller Williams Realty International Lifestyles

  724 Grove St, Winter Haven, FL 33884
• 

  

  /2

  $400,000 Sold Aug 26, 2025

  • 2,095 Sq Ft
  • $191/SF
  • 150 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2018

  4033 Phoenician Way, Winter Haven, FL 33884

  Experience luxury 55+ living in this beautifully upgraded 3-bedroom, 2-bath home with a private heated saltwater pool and spa, located in the highly sought-after Lake Ashton community. Designed for comfort and entertainment, this home boasts an open-concept floor plan with luxury vinyl plank flooring, a spacious primary suite with a walk-in closet and glass-enclosed shower, and a gourmet kitchen

  Brad Kirwan GLOBAL LIFESTYLE LLC

  4033 Phoenician Way, Winter Haven, FL 33884
• 

  

  

  /61

  Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 2,133 Sq Ft

  304 Thornhill Estates Ct, Winter Haven, FL 33880

  304 Thornhill Estates Ct, Winter Haven, FL 33880
• 

  

  

  /45

  $320,000

  • 4 Beds
  • 2 Baths
  • 1,828 Sq Ft

  4094 Great Egret Dr, Winter Haven, FL 33881

  Welcome to this beautiful and well-maintained 4-bedroom, 2-bathroom single-family home located in a quiet area of Winter Haven, Florida. The property offers an open layout that seamlessly connects the living and dining rooms, creating a perfect setting for family gatherings or entertaining. The modern kitchen is the heart of the home, equipped with a large center island with a drop-in sink, ideal

  Gil Medina REALTY ONE GROUP MAGIC CITY

  4094 Great Egret Dr, Winter Haven, FL 33881
• 

  

  /22

  $1,669 per month

  • 4 Beds
  • 2 Baths
  • 1,728 Sq Ft
  • House for Rent

  2936 Whispering Trails Dr, Winter Haven, FL 33884

  This home is professionally managed by Tricon Residential, dedicated to creating exceptional rental experiences. Featuring 4 bedrooms, 2 bathrooms, and approximately 1,728 square feet, this well-maintained home offers a high standard of rental living, supported by a team that puts residents first. As a Tricon resident, you'll enjoy access to Tricon Vantage — a program designed to support your

  2936 Whispering Trails Dr, Winter Haven, FL 33884
• 

  /2

  $270,000 Sold Aug 25, 2025

  • 1,794 Sq Ft
  • $151/SF
  • 4 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1966

  1900 Manor Cir SE, Winter Haven, FL 33880

  Timeless curb appeal, a walkable neighborhood and solid construction—this is the kind of home that stands the test of time. Perfectly situated on an oversized 0.38-acre corner lot, 1900 Manor Circle S.E. in Winter Haven, Florida, offers 3 bedrooms, 2 baths, and a spacious ranch-style layout that works beautifully whether you’re just starting out, growing a family or enjoying

  Michael Stone THE STONES REAL ESTATE FIRM

  1900 Manor Cir SE, Winter Haven, FL 33880
• 

  

  /25

  Est $275,493 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,320 Sq Ft

  842 Terranova Rd, Winter Haven, FL 33884

  842 Terranova Rd, Winter Haven, FL 33884
• 

  

  /30

  $315,000

  • 4 Beds
  • 2 Baths
  • 1,696 Sq Ft

  1228 Denali Dr, Winter Haven, FL 33881

  Better Than New 4 Bedroom Home, Handicap Accessible, No CDD, & Move-In Ready! This 4 bedroom, 2 bath home is truly better than new and designed with comfort and accessibility in mind. With 36” doorways, an automatic door opener, and a roll-in shower, it’s thoughtfully built to be handicap accessible while maintaining a modern and stylish feel. Inside, you’ll find ceramic tile throughout, creating

  Jackie Mazurowski KELLER WILLIAMS REALTY SMART 1

  1228 Denali Dr, Winter Haven, FL 33881
• 

  

  /12

  $1,200 per month

  • 2 Beds
  • 1.5 Baths
  • 1,680 Sq Ft
  • Condo for Rent

  67 Deena Way, Winter Haven, FL 33880

  Beautiful 2 bedroom and 1.5 bath condo. Near Schools and retail shops. Schedule a viewing today before its gone.

  maria vega THE EXPERTS TEAM REALTY INC

  67 Deena Way, Winter Haven, FL 33880
• 

  /2

  $719,990 Sold Aug 25, 2025

  • 3,178 Sq Ft
  • $227/SF
  • 8 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2005

  9516 Waterford Oaks Blvd, Winter Haven, FL 33884

  Welcome to this absolutely amazing 4 bedroom, 3 bathroom home that shows like a luxurious model home. Designed by Authur Rutenberg and build by Henderson Homes in 2005, it offers a spacious and open floor plan with countless high-end upgrades that make it extremely attractive. The interior has beautiful tile that flows throughout the The bright, open floor plan and main living areas have tile and

  Thomas Popadak LA ROSA REALTY PRESTIGE

  9516 Waterford Oaks Blvd, Winter Haven, FL 33884
• 

  

  /32

  Est $331,299 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,630 Sq Ft

  478 Majestic Gardens Blvd, Winter Haven, FL 33880

  478 Majestic Gardens Blvd, Winter Haven, FL 33880
• 

  

  /46

  $335,000

  • 3 Beds
  • 2 Baths
  • 1,871 Sq Ft

  4009 Bedford Ave, Winter Haven, FL 33884

  This fabulous Eco-Smart home is nestled in the highly desirable, maintenance-free, gated community of Traditions at Lake Ruby. Upon arrival, you’ll be welcomed by a charming front patio adorned with pavers, setting the stage for this beautifully maintained residence. Inside, the spacious great room boasts diagonally set tile flooring, crown molding, and oversized glass sliding doors that open to

  Eileen Belanger CENTURY 21 MYERS REALTY LAKE WALES

  4009 Bedford Ave, Winter Haven, FL 33884
• 

  

  /17

  $2,049 per month

  • 4 Beds
  • 2 Baths
  • 1,867 Sq Ft
  • House for Rent

  242 Meadowbrook Blvd, Winter Haven, FL 33881

  This home is professionally managed by Tricon Residential, dedicated to creating exceptional rental experiences. Featuring 4 bedrooms, 2 bathrooms, and approximately 1,867 square feet, this well-maintained home offers a high standard of rental living, supported by a team that puts residents first. As a Tricon resident, you'll enjoy access to Tricon Vantage — a program designed to support your

  242 Meadowbrook Blvd, Winter Haven, FL 33881
• 

  /2

  $318,520 Sold Aug 25, 2025

  • 1,715 Sq Ft
  • $186/SF
  • 0 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 2025

  476 Ituna Cir, Winter Haven, FL 33881

  Under Construction. New construction home with 1715 square feet on one-story including 4 bedrooms, 2 baths, and an open living area. Enjoy an open kitchen with Quartz countertops, Samsung stainless steel appliances, a walk-in pantry, and a spacious island, fully open to the dining cafe and gathering room. The living area, laundry room, and baths include luxury wood vinyl plank flooring, with

  George Lindsey, III CAMBRIDGE REALTY OF CENTRAL FL

  476 Ituna Cir, Winter Haven, FL 33881
• 

  

  /40

  Est $317,214 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,850 Sq Ft

  402 Bigstaff Ct, Winter Haven, FL 33884

  402 Bigstaff Ct, Winter Haven, FL 33884
• 

  

  /24

  $309,999

  • 4 Beds
  • 2 Baths
  • 1,820 Sq Ft

  1663 Tressel Ct, Winter Haven, FL 33881

  This spacious 4-bedroom, 2-bath home is located in a desirable gated community, offering both comfort and peace of mind.Enjoy the benefits of a well-kept neighborhood with a low HOA that maintains the community’s charm and curb appeal. With four bedrooms, there’s plenty of space for a growing family, a home office, or guest accommodations.Conveniently situated near shopping, dining,

  Karina Turcios LPT REALTY, LLC

  1663 Tressel Ct, Winter Haven, FL 33881
• 

  

  /22

  $2,600 per month

  • 3 Beds
  • 2 Baths
  • 1,391 Sq Ft
  • House for Rent

  112 Lagoon Rd, Winter Haven, FL 33884

  For Rent – Winter Haven, FLWelcome to this beautifully remodeled home located at 112 Lagoon Rd, Winter Haven, FL 33884. This property offers comfort, convenience, and a prime location.?? Property Features: • 3 spacious bedrooms • 2 updated bathrooms • Modern remodeled kitchen with quality finishes • Indoor laundry area for added

  Zulmy Serrano AGENT TRUST REALTY CORPORATION

  112 Lagoon Rd, Winter Haven, FL 33884
• 

  /2

  $500,000 Sold Aug 25, 2025

  • 2,880 Sq Ft
  • $174/SF
  • 4 Days On Market

  • 5 Beds
  • 4 Baths
  • Built 1975

  237 Manatee Rd, Winter Haven, FL 33884

  One or more photo(s) has been virtually staged. GORGEOUS LARGE FAMILY HOME!!! 5BR/4BA POOL HOME with 2 MASTER SUITES, MOTHER-IN-LAW OPTION & 3-CAR GARAGE in SE Winter Haven!(more pictures are on the way)This is the one you’ve been waiting for! Nestled in the heart of Southeast Winter Haven, this stunning two-story family pool home is packed with space, style, and flexibility—perfect

  Brooklyn Paul BETTER HOMES AND GARDENS REAL ESTATE LIFESTYLES REALTY

  237 Manatee Rd, Winter Haven, FL 33884
• 

  

  /44

  Est $388,852 Not Listed For Sale

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

  849 Terranova Rd, Winter Haven, FL 33884

  849 Terranova Rd, Winter Haven, FL 33884
• 

  

  /26

  $350,000

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

  3600 Julius Estates Blvd, Winter Haven, FL 33881

  AMAZING two-story home!!! Located in a BEAUTIFUL LAKEFRONT COMMUNITY! HUGE, fenced corner lot, very nice layout with a FLEX area/room that can be used as a formal Livingroom, office, or den, large master bedroom with a nice bathroom with dual sinks, walk in shower & walk-in closet, laundry room, 2 car garage & so much MORE**Seller may consider buyer's concessions **CALL YOUR AGENT FOR A PRIVATE

  Gladys Falcon LUXURY REAL ESTATE GROUP LLC

  3600 Julius Estates Blvd, Winter Haven, FL 33881
• 

  

  /19

  $2,039 per month

  • 4 Beds
  • 2 Baths
  • 1,814 Sq Ft
  • House for Rent

  113 Solis Dr, Winter Haven, FL 33880

  This home is professionally managed by Tricon Residential, dedicated to creating exceptional rental experiences. Featuring 4 bedrooms, 2.0 bathrooms, and approximately 1,814 square feet, this well-maintained home offers a high standard of rental living, supported by a team that puts residents first. As a Tricon resident, you'll enjoy access to Tricon Vantage — a program designed to support your

  113 Solis Dr, Winter Haven, FL 33880
• 

  /2

  $249,900 Sold Aug 25, 2025

  • 1,544 Sq Ft
  • $162/SF
  • 49 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1965

  2424 Bates Ave SW, Winter Haven, FL 33880

  Welcome to 2424 Bates Ave – a well-maintained 3-bedroom, 2-bathroom home featuring a versatile mother-in-law suite, perfect for extended family, guests, or rental income potential. Nestled in a peaceful neighborhood just minutes from Winter Haven’s famous Chain of Lakes, this property offers both comfort and convenience.Inside, you’ll find a spacious and functional layout, a bright

  David Fleming BHHS FLORIDA PROPERTIES GROUP

  2424 Bates Ave SW, Winter Haven, FL 33880
• 

  

  /30

  Est $323,764 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,906 Sq Ft

  1737 Muirfield Village St, Winter Haven, FL 33881

  1737 Muirfield Village St, Winter Haven, FL 33881
• 

  

  /54

  $325,000

  • 2 Beds
  • 2 Baths
  • 1,622 Sq Ft

  560 Saint Andrews Rd, Winter Haven, FL 33884

  Welcome to 560 St Andrews Rd in Cypresswood Golf & Country Club!This beautiful patio home is truly move-in ready, offering 2 bedrooms, 2 bathrooms, and plenty of stylish updates.From the moment you arrive, you’ll be impressed by the brick-paver driveway, lush landscaping, and inviting curb appeal. Inside, the spacious living, dining, and kitchen areas feature wood-look ceramic tile floors, adding

  Corinna Weaver CROSBY & ASSOCIATES, INC.

  560 Saint Andrews Rd, Winter Haven, FL 33884
• 

  

  /3

  $2,150 per month

  • 2 Beds
  • 2 Baths
  • 1,077 Sq Ft
  • Condo for Rent

  689 Lake Howard Dr NW Unit 3B, Winter Haven, FL 33880

  Discover the idyllic lake life of this charming and peaceful condo in the desirable 55+ community of Winter Haven, Florida. This unit offers a beautiful quaint view of Lake Howard and the private covered dock, giving you a serene Lakeside experience. Featuring two bedrooms and two bath FULLY FURNISHED for an effortless move-in. The living room includes a comfortable couch, two recliners and a TV,

  Januarie Scorsese KELLER WILLIAMS RLTY NEW TAMPA

  689 Lake Howard Dr NW Unit 3B, Winter Haven, FL 33880
• 

  /2

  $284,990 Sold Aug 25, 2025

  • 1,665 Sq Ft
  • $171/SF
  • 43 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 2025

  4920 Kaia Ave, Winter Haven, FL 33884

  Under Construction. Introducing the Harper floorplan at Villamar, where every square foot is put to use with sophistication and comfort.Inside this 4 bedroom, 2 bathroom home, you’ll find 1,665 square feet of comfortable living. This meticulously designed residence combines modern convenience with timeless elegance, showcasing quartz and tile floors throughout. As you step inside, you are

  Paul King DR HORTON REALTY OF CENTRAL FLORIDA LLC

  4920 Kaia Ave, Winter Haven, FL 33884
• 

  

  /21

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,512 Sq Ft

  5722 E Lake Fox Dr, Winter Haven, FL 33884

  5722 E Lake Fox Dr, Winter Haven, FL 33884
• 

  

  /66

  $429,900

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

  144 Beverly Dr, Winter Haven, FL 33884

  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 updates include: whole house replumbed 2019, new roof 2019, new AC handler 2019, master bath

  Christina Loesch AGILE GROUP REALTY

  144 Beverly Dr, Winter Haven, FL 33884
• 

  

  /14

  $1,649 per month

  • 3 Beds
  • 2 Baths
  • 1,443 Sq Ft
  • House for Rent

  1208 Salisbury Dr, Winter Haven, FL 33881

  This home is professionally managed by Tricon Residential, dedicated to creating exceptional rental experiences. Featuring 3 bedrooms, 2 bathrooms, and approximately 1,443 square feet, this well-maintained home offers a high standard of rental living, supported by a team that puts residents first. As a Tricon resident, you'll enjoy access to Tricon Vantage — a program designed to support your

  1208 Salisbury Dr, Winter Haven, FL 33881
• 

  /2

  $234,900 Sold Aug 25, 2025

  • 1,013 Sq Ft
  • $232/SF
  • 68 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2025

  3438 Avenue East NW, Winter Haven, FL 33880

  REDUCED!!!! Brand New 2024 Home in NW Winter Haven!Welcome to this beautiful 3-bedroom, 2-bathroom new construction home located in desirable Northwest Winter Haven! Close to schools, shopping, and churches, with easy access to the Parkway—perfect for commuting to Lakeland, Tampa, or Orlando. Whether you're a first-time homebuyer, looking to downsize, or just starting fresh, this home is a

  Marissa Hipp COLDWELL BANKER REALTY

  3438 Avenue East NW, Winter Haven, FL 33880
• 

  

  /20

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 840 Sq Ft

  5978 Foxhollow Dr, Winter Haven, FL 33884

  5978 Foxhollow Dr, Winter Haven, FL 33884
• 

  

  /51

  $309,000

  • 4 Beds
  • 2 Baths
  • 1,898 Sq Ft

  1073 Brenton Manor Dr, Winter Haven, FL 33881

  Beautiful 4-bedroom, 2-bath home located in the desirable Brenton Manor community. This property features an open floor plan with plenty of natural light, a spacious kitchen with modern cabinetry, and a comfortable primary suite with walk-in closet and private bath. Enjoy a private backyard, two-car garage, and convenient access to schools, shopping, dining, and major highways. Don’t miss this

  Karia Ortiz FORTEZA REALTY LLC

  1073 Brenton Manor Dr, Winter Haven, FL 33881
• 

  

  /15

  $2,250 per month

  • 4 Beds
  • 2 Baths
  • 1,665 Sq Ft
  • House for Rent

  1349 Daisy Field Dr, Winter Haven, FL 33884

  A beautiful, spacious house with 4 bedrooms and 2 bathrooms is waiting for you, fully furnished. Just bring your suitcases and enjoy. It has a unique appeal: it's fully fenced and has solar panels, so you pay very little for electricity.The best thing is that it's just minutes from Legoland, so your weekends can be filled with fun, outings, and memories with the family. Nearby, you'll

  Karla Rangel LA ROSA REALTY LLC

  1349 Daisy Field Dr, Winter Haven, FL 33884
• 

  /2

  $435,000 Sold Aug 25, 2025

  • 3,920 Sq Ft
  • $111/SF
  • 86 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 2008

  393 Fish Hawk Dr, Winter Haven, FL 33884

  One or more photo(s) has been virtually staged. They don’t make them this big anymore! This spacious 5-bedroom, 4.5-bathroom home in Hart Lake Cove has been completely refreshed and is ready for its new owner! With nearly 4,000 sq. ft. of living space, a three-car garage, and two master suites (one on each floor), this home offers endless possibilities for comfortable living. A great room, formal

  Renee Anthony WATSON REALTY CORP.

  393 Fish Hawk Dr, Winter Haven, FL 33884
• 

  

  /26

  Est $339,225 Not Listed For Sale

  • 3 Beds

  1410 17th St NW, Winter Haven, FL 33881

  1410 17th St NW, Winter Haven, FL 33881
• 

  

  /20

  $310,000 Open Sat 11AM - 2PM

  • 3 Beds
  • 2 Baths
  • 1,543 Sq Ft

  111 Krenson Bay Loop, Winter Haven, FL 33881

  Don’t miss this nearly new 3 bedroom, 2 bath home located in a desirable community in Winter Haven! Built just 2 years ago, this move-in ready property offers modern finishes, and energy-efficient features throughout. The spacious kitchen includes stainless steel appliances, a large island, and ample cabinet space, perfect for entertaining. The split bedroom plan provides privacy, with a generous

  Neisha Crespo CROWN LEGACY REALTY LLC

  111 Krenson Bay Loop, Winter Haven, FL 33881
• 

  

  /19

  $2,075 per month

  • 4 Beds
  • 2 Baths
  • 1,981 Sq Ft
  • House for Rent

  4766 Osprey Way, Winter Haven, FL 33881

  Now offering 20-month leases. Sign today and lock in today’s low rate for the next 20 months! Disclaimer: Offer valid for new applicants who sign a 20-month lease, limited to the first 500 executed leases. Base rent will remain at the 12-month lease rate for the duration of the 20-month term. Offer is contingent on application approval and execution of a lease agreement. Other terms and

  4766 Osprey Way, Winter Haven, FL 33881
• 

  /2

  $297,900 Sold Aug 23, 2025

  • 1,715 Sq Ft
  • $174/SF
  • 177 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 2025

  721 Bayside Blvd, Winter Haven, FL 33881

  New construction home with 1715 square feet on one-story including 4 bedrooms, 2 baths, and an open living area. Enjoy an open kitchen with Quartz countertops, Samsung stainless steel appliances, a walk-in pantry, and a spacious island, fully open to the dining cafe and gathering room. The living area, laundry room, and baths include luxury wood vinyl plank flooring, with stain-resistant

  George Lindsey, III CAMBRIDGE REALTY OF CENTRAL FL

  721 Bayside Blvd, Winter Haven, FL 33881
• 

  /2

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,448 Sq Ft

  6032 Grand Oaks Dr SE, Winter Haven, FL 33884

  6032 Grand Oaks Dr SE, Winter Haven, FL 33884

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