Winter Haven, FL Homes

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  /55

  $178,000

  • 3 Beds
  • 2 Baths

  166 Oak Tree Blvd, Winter Haven, FL 33880

  Beautiful, Fully Furnished, 3BR/2BA Home in a Spectacular Gated Community for folks age 55+. Low Lot Rent. The home is only 4 years old, offering comfortable living in an amenity-rich park with plenty of space, convenience, and recreation right outside your door. The home features a connected storage building, washer and dryer included, and a wonderful screened-in lanai with patio furniture-the

  

  Glenn Fogg

  FOGG MOBILE HOME SALES LLC

  166 Oak Tree Blvd, Winter Haven, FL 33880
• Explore Winter Haven

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  /26

  Starting at $1,269 Per Month

  • 1 - 3 Beds

  1015 Lake Forest Blvd, Winter Haven, FL 33884

  Experience stylish, comfortable living at The Waverly at Winter Haven. Located in the sought-after Cypress Gardens area, our pet-friendly community offers a peaceful lifestyle with convenient access to everything Central Florida has to offer.At The Waverly at Winter Haven, you'll enjoy a host of resort-inspired amenities designed to enhance your lifestyle, from a sparkling pool and

  The Waverly at Winter Haven

  

  1015 Lake Forest Blvd, Winter Haven, FL 33884
• 

  

  /2

  $257,000

  Sold Dec 02, 2025

  409 Lake Ned Rd, Winter Haven, FL 33884

  • 4 Beds
  • 3 Baths
  • 2,210 Sq Ft
  • Built 1969

  Last Sold Summary

  • 4% Below List Price
  • $116/SF
  • 22 Days On Market

  Current Estimated Value $270,504

  Last Listing Agent Ashley Lopez KELLER WILLIAMS REALTY SMART 1

  409 Lake Ned Rd, Winter Haven, FL 33884
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  /2

  Not Listed For Sale

  451 Village Cir SW, Winter Haven, FL 33880

  • 2 Beds
  • 2 Baths
  • 1,456 Sq Ft
  • Built 1989

  451 Village Cir SW, Winter Haven, FL 33880

  Last Sold Summary

  • 43 Days On Market

  Last Listing Agent Carolyn Christian DALTON WADE INC
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  /14

  $49,900

  $10K PRICE DROP

  • 2 Beds
  • 2 Baths

  1082 Eagle Dr, Winter Haven, FL 33881

  Welcome home to this well maintained 2-bedroom, 2-bath residence offering 1,352 sq ft of comfortable and inviting living space, perfectly situated on a desirable corner lot. From the moment you arrive, you'll appreciate the pride of ownership and care that shines throughout the home. A new roof and new A/C have already been completed in 2025 for added peace of mind. Inside, you'll find a spacious

  

  Cindy Minnick

  Sun Resales, Inc.

  1082 Eagle Dr, Winter Haven, FL 33881
• 

  

  /20

  $1,700 Per Month

  • 2 Beds
  • 1 Bath
  • 1,032 Sq Ft
  • House for Rent

  1313 4th St NE, Winter Haven, FL 33881

  Welcome home to this charming 2-bedroom, 1-bathroom rental located in the desirable Chain of Lakes area of Winter Haven! This beautifully renovated home offers a comfortable and inviting space with plenty of room to make it your own. Featuring a newer roof installed in Fall 2023, the home also includes a versatile bonus room that can be used as a home office, guest space, playroom, or additional

  

  Rafael Narvaez

  EXP REALTY LLC

  1313 4th St NE, Winter Haven, FL 33881
• 

  /2

  $260,000

  Sold Mar 23, 2026

  565 Terranova Cir, Winter Haven, FL 33884

  • 3 Beds
  • 2 Baths
  • 1,448 Sq Ft
  • Built 2003

  Last Sold Summary

  • 7% Below List Price
  • $180/SF
  • 113 Days On Market

  Current Estimated Value $260,237

  Last Listing Agent Robert Jones OFFERPAD BROKERAGE FL, LLC

  565 Terranova Cir, Winter Haven, FL 33884
• 

  /2

  Est $337,984

  Not Listed For Sale

  3507 Costello Cir, Winter Haven, FL 33884

  • 5 Beds
  • 3 Baths
  • 2,447 Sq Ft
  • Built 2025

  3507 Costello Cir, Winter Haven, FL 33884

  Last Sold Summary

  • 17 Days On Market

  Last Listing Agent Paul King DR HORTON REALTY OF CENTRAL FLORIDA LLC
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  /45

  $269,900

  $33K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,583 Sq Ft

  780 Overlook Grove Dr, Winter Haven, FL 33884

  HOME WARRANTY INCLUDED! Need 4 bedrooms, but don't need to break the budget? This is what you've been searching for here in the heart of Winter Haven! Situated perfectly W of Hwy 27 and out of the hustle and bustle of the city, this 4/2/2 home is ready for you! Close to houses of worship, schools, shopping, golf, and SO much more! Upon arrival, you note the quaint neighborhood, which quickly says

  

  Cyleste Goodson

  FLORIDA REAL ESTATE COMPANY

  780 Overlook Grove Dr, Winter Haven, FL 33884
• 

  

  /54

  Starting at $1,455 Per Month

  • 1 - 3 Beds

  1015 Mahaffey Rd, Winter Haven, FL 33884

  A luxury rental lakefront apartment community in Winter Haven, Florida. Accepting leases now.

  The Carlton at Lake Dexter

  

  1015 Mahaffey Rd, Winter Haven, FL 33884
• 

  /2

  $255,999

  Sold Aug 17, 2026

  5041 Kaia Ave, Winter Haven, FL 33884

  • 3 Beds
  • 2 Baths
  • 1,269 Sq Ft
  • Built 2026

  Last Sold Summary

  • 13% Below List Price
  • $202/SF
  • 63 Days On Market

  Current Estimated Value $245,804

  Last Listing Agent Bryan Sumner MERITAGE HOMES OF FL REALTY

  5041 Kaia Ave, Winter Haven, FL 33884
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  /17

  Not Listed For Sale

  5006 Abigail Dr, Winter Haven, FL 33859

  • 4 Beds
  • 2 Baths
  • 1,938 Sq Ft
  • Built 2025

  5006 Abigail Dr, Winter Haven, FL 33859

  Last Sold Summary

  • 30 Days On Market
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  /42

  $336,000

  $33K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,476 Sq Ft

  1063 Brimstone Cir, Winter Haven, FL 33884

  HUGE PRICE REDUCTION! WHY BUY NEW? THIS ONE IS IN AN ESTABLISHED, BUILT OUT ENCLAVE AND LIKE NEW FOR $136 A SQ FT. Welcome to this stunning 2024-built Ensley model located in the highly sought-after Harmony at Lake Eloise community in Winter Haven, Florida. Offering, 2,476 square feet of beautifully designed living space and over 2,900 total square feet under roof and all exterior block

  

  Brad Martin

  BETTER HOMES AND GARDENS REAL ESTATE LIFESTYLES REALTY

  1063 Brimstone Cir, Winter Haven, FL 33884
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  /6

  $1,300 Per Month

  • 1 Bed
  • 1 Bath
  • 2,109 Sq Ft
  • House for Rent

  1453 Austin St Unit B, Winter Haven, FL 33884

  Charming PRIVATE ENTRANCE 1 - NEW bedroom apartment available for rent! Welcome to your new home! This beautiful apartment with living room, kitchen, 1 bathroom and 1 bedroom. Located in a quiet and friendly neighborhood in Eagle Lake, this space offers all the comfort and convenience you need. As for the location, it is close to shopping centers, restaurants, parks and public transportation.

  

  Isabel Melin Mora

  MELIN REALTY LLC

  1453 Austin St Unit B, Winter Haven, FL 33884
• 

  /2

  $294,900

  Sold Jun 11, 2026

  4507 Rapallo Ave, Winter Haven, FL 33884

  • 4 Beds
  • 2 Baths
  • 1,754 Sq Ft
  • Built 2025

  Last Sold Summary

  • 10% Below List Price
  • $168/SF
  • 84 Days On Market

  Current Estimated Value $295,674

  Last Listing Agent George Lindsey, III CAMBRIDGE REALTY OF CENTRAL FL

  4507 Rapallo Ave, Winter Haven, FL 33884
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  /2

  Not Listed For Sale

  6515 Raintree Ln, Winter Haven, FL 33881

  • 2 Beds
  • 2 Baths
  • 1,620 Sq Ft
  • Built 1987

  6515 Raintree Ln, Winter Haven, FL 33881

  Last Sold Summary

  • 125 Days On Market

  Last Listing Agent Jean Murphy CENTURY 21 MYERS REALTY
• 

  

  /23

  $234,900

  $15K PRICE DROP Under Contract

  • 3 Beds
  • 2 Baths
  • 1,708 Sq Ft

  695 22nd St NW, Winter Haven, FL 33880

  Under contract-accepting backup offers. A 3 bedroom, 2 bathroom home featuring a separate BONUS ROOM and MUD ROOM is hard to find....Especially under 250K!The spacious kitchen features beautiful newer wood cabinetry and a cozy breakfast nook, creating a warm and inviting space for everyday meals. The generously sized living room flows into a separate dining room, which conveniently leads

  

  Melissa Frederick

  DREAM REALTY GROUP

  695 22nd St NW, Winter Haven, FL 33880
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  /36

  Starting at $1,329 Per Month

  • 1 - 2 Beds

  5004 Dream Dr, Winter Haven, FL 33880

  Dream Winter Haven offers comfortable, brand-new one-, two-, and three-bedroom apartment homes in Winter Haven, Florida, thoughtfully designed to provide modern convenience, connection, and a welcoming place to call home. Ideally located in Central Florida, our pet-friendly community provides easy access to shopping, dining, entertainment, outdoor recreation, and LEGOLAND Florida. Residents enjoy

  Dream Winter Haven

  

  5004 Dream Dr, Winter Haven, FL 33880
• 

  /2

  $325,000

  Sold Dec 26, 2025

  2438 5th St NE, Winter Haven, FL 33881

  • 6 Beds
  • 3 Baths
  • 1,950 Sq Ft
  • Built 1969

  Last Sold Summary

  • $167/SF
  • 6 Days On Market

  Current Estimated Value $340,284

  Last Listing Agent Pedro Fernandez Salvador CONTEMPORARY REALTY GROUP

  2438 5th St NE, Winter Haven, FL 33881
• 

  /2

  Est $151,887

  Not Listed For Sale

  299 Winter Ridge Blvd Unit 283, Winter Haven, FL 33881

  • 3 Beds
  • 2 Baths
  • 1,073 Sq Ft
  • Built 1994

  299 Winter Ridge Blvd Unit 283, Winter Haven, FL 33881

  Last Sold Summary

  • 82 Days On Market

  Last Listing Agent Andrea Friedmann KELLER WILLIAMS REALTY SMART 1
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  /86

  $720,000

  • 4 Beds
  • 4 Baths
  • 2,961 Sq Ft

  237 Mclean Point, Winter Haven, FL 33884

  MUST SEE! Beautiful Custom-Built Home in the Renaissance Subdivision! Welcome to your dream home nestled in the serene community of Renaissance in lovely Winter Haven, Florida. This stunning 4-bedroom, 4-bathroom model home offers the perfect blend of privacy, convenience, and resort-style living, complete with a spectacular pool area. Key Features: • Prime Location: Enjoy boat access to Lake

  

  Luis Perez Garcia

  EXP Realty LLC

  237 Mclean Point, Winter Haven, FL 33884
• 

  

  /25

  $1,500 Per Month

  • 2 Beds
  • 1 Bath
  • 868 Sq Ft
  • House for Rent

  248 Avenue L NE, Winter Haven, FL 33881

  Adorable move-in ready 2-bedroom, 1-bath home! This delightful property features vinyl plank flooring throughout, with ceramic tile in the bathroom for easy maintenance. The open great room is filled with natural light, creating a warm, welcoming atmosphere. The kitchen boasts sleek stainless steel appliances, ample counter space, and a convenient breakfast bar with additional cabinets on the

  

  CarLee Marchetti

  STAR REALTY OF WINTER HAVEN

  248 Avenue L NE, Winter Haven, FL 33881
• 

  

  /18

  $242,490

  Sold May 28, 2026

  3040 Captain Jax Way, Winter Haven, FL 33884

  • 3 Beds
  • 2.5 Baths
  • 1,423 Sq Ft
  • Built 2026

  Move in Ready Sold Summary

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

  Current Estimated Value $253,000

  Lennar Peace Creek Reserve - Serenity

  3040 Captain Jax Way, Winter Haven, FL 33884
• 

  /2

  Est $236,849

  Not Listed For Sale

  1013 Carefree Cove Dr, Winter Haven, FL 33881

  • 3 Beds
  • 1.5 Baths
  • 1,025 Sq Ft
  • Built 1972

  1013 Carefree Cove Dr, Winter Haven, FL 33881

  Last Sold Summary

  • 27 Days On Market

  Last Listing Agent Jessica Falvey ELITE REAL ESTATE AND PROPERTY MANAGEMENT
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  /39

  $295,000

  $23K PRICE DROP

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

  1799 Carnostie Rd, Winter Haven, FL 33884

  PRICE LOWERED JUST FOR YOU! Move right into this pristine, turnkey oasis. Built in 2022, this beautifully maintained home in the peaceful Villa Mar community features a bright, open floor plan and four spacious bedrooms. The modern kitchen flows effortlessly into the main living areas, which boast durable ceramic tile flooring for a sleek, low-maintenance finish. Relax on your private,

  

  Twanna Dewdney

  LA ROSA REALTY PRESTIGE

  1799 Carnostie Rd, Winter Haven, FL 33884
• 

  

  /53

  Starting at $1,250 Per Month

  • Studio - 2 Beds

  265 Ave E SW, Winter Haven, FL 33880

  Discover the essence of upscale living at The Breeze, where the vibrant spirit of Winter Haven meets the serenity of a private retreat. Our community was designed for those who demand more from their surroundings. Each residence serves as a masterclass in architectural efficiency, blending high-performance energy standards with "luxury-first" essentials. From gourmet-inspired kitchens to living

  The Breeze

  

  265 Ave E SW, Winter Haven, FL 33880
• 

  /2

  $280,000

  Sold Mar 05, 2026

  6654 Crescent Loop, Winter Haven, FL 33884

  • 4 Beds
  • 2 Baths
  • 1,820 Sq Ft
  • Built 2014

  Last Sold Summary

  • 7% Below List Price
  • $154/SF
  • 138 Days On Market

  Current Estimated Value $287,322

  Last Listing Agent Cindy Thornton AGILE GROUP REALTY

  6654 Crescent Loop, Winter Haven, FL 33884
• 

  /2

  Est $124,272

  Not Listed For Sale

  1550 11th St NE Unit E7, Winter Haven, FL 33881

  • 2 Beds
  • 2 Baths
  • 1,148 Sq Ft
  • Built 1974

  1550 11th St NE Unit E7, Winter Haven, FL 33881

  Last Sold Summary

  • 119 Days On Market

  Last Listing Agent Renee Butler BROKERS REALTY OF CENTRAL FLOR
• 

  

  /31

  $90,000

  $39K PRICE DROP

  • 2 Beds
  • 2 Baths

  355 Putter Cir, Winter Haven, FL 33881

  Welcome home to this beautifully maintained 2 bedroom, 2 bath residence offering approximately 1,300 sq ft of comfortable living space and sold fully furnished with an updated kitchen, a bonus room perfect for an office, craft space, or hobbies, and French doors that open into a roomy, front-facing Florida room, ideal for morning coffee or relaxing evenings. Thoughtful details include raised

  

  Cindy Minnick

  Sun Resales, Inc.

  355 Putter Cir, Winter Haven, FL 33881
• 

  

  /37

  $1,850 Per Month

  • 2 Beds
  • 2.5 Baths
  • 1,407 Sq Ft
  • Townhouse for Rent

  504 Orange Blossom Dr, Winter Haven, FL 33880

  Welcome to unit 504 – this stunning 2-bedroom 2.5 bath Chain-of-Lakes LAKEFRONT townhome is nestled in a serene community of Waters Edge. Downstairs features; spacious great room with a decorative fireplace, 2 access sliding glass doors leading to the screened-in lanai, with convenient storage closet. A wrap-around kitchen with ample counter space and all stainless-steel appliances. Off the

  

  CarLee Marchetti

  STAR REALTY OF WINTER HAVEN

  504 Orange Blossom Dr, Winter Haven, FL 33880
• 

  /2

  $324,625

  Sold Jul 31, 2026

  512 Ituna Cir, Winter Haven, FL 33881

  • 3 Beds
  • 2 Baths
  • 1,545 Sq Ft
  • Built 2026

  Move in Ready Sold Summary

  • $210/SF
  • 10 Days On Market

  Current Estimated Value $274,667

  Highland Homes Harbor at Lake Henry - Single-Family Homes

  512 Ituna Cir, Winter Haven, FL 33881
• 

  /2

  Est $280,210

  Not Listed For Sale

  5609 Forest Ridge Dr, Winter Haven, FL 33881

  • 3 Beds
  • 2 Baths
  • 1,534 Sq Ft
  • Built 2007

  5609 Forest Ridge Dr, Winter Haven, FL 33881

  Last Sold Summary

  • 63 Days On Market

  Last Listing Agent Rhansel Acevedo Rodriguez EXP REALTY LLC
• 

  

  /36

  $385,000

  Under Contract

  • 3 Beds
  • 2.5 Baths
  • 2,039 Sq Ft

  4519 Ashford Dr, Winter Haven, FL 33880

  Under contract-accepting backup offers. Beautifully maintained 3-bedroom, 2.5-bath home on a spacious 0.30-acre lot in the desirable Lake Thomas Woods community with NO HOA! This inviting two-story home features an open floor plan with soaring 17-foot ceilings in the living room, abundant natural light, and a cozy wood-burning fireplace. The remodeled kitchen is designed for both style and

  

  Amy Reynolds

  LOCKHART & ASSOCIATES INC

  4519 Ashford Dr, Winter Haven, FL 33880
• 

  

  /22

  Starting at $1,441

  Total Monthly Price

  • 1 - 2 Beds

  3110 Gowan Dr, Winter Haven, FL 33884

  Welcome home to Prose Cypress Pointe, a brand-new multifamily community located in Winter Haven, Florida. Our spacious one- and two-bedroom apartment homes feature modern stainless-steel appliances, walk-in closets, dining-sized kitchen islands, premium plank flooring throughout and full-sized washers and dryers in every apartment home. And with convenient, must-have amenities like a fitness

  Prose Cypress Pointe

  

  3110 Gowan Dr, Winter Haven, FL 33884
• 

  /2

  $280,900

  Sold Sep 11, 2026

  549 Ituna Cir, Winter Haven, FL 33881

  • 3 Beds
  • 2 Baths
  • 1,479 Sq Ft
  • Built 2026

  Last Sold Summary

  • $190/SF
  • 0 Days On Market

  Last Listing Agent George Lindsey, III CAMBRIDGE REALTY OF CENTRAL FL

  549 Ituna Cir, Winter Haven, FL 33881
• 

  /2

  Est $266,431

  Not Listed For Sale

  645 Avenue A NE, Winter Haven, FL 33881

  • 2 Beds
  • 1.5 Baths
  • 1,517 Sq Ft
  • Built 1939

  645 Avenue A NE, Winter Haven, FL 33881

  Last Sold Summary

  • 60 Days On Market

  Last Listing Agent Franco Poerio Skubna CENTURY 21 MYERS REALTY
• 

  

  /36

  $49,990

  • 2 Beds
  • 2 Baths
  • 1,232 Sq Ft

  5297 Laurel Oak Dr, Winter Haven, FL 33880

  Florida flavor starts in the backyard at 5297 Laurel Oak Drive, where fruit-bearing plantings add character to this newly listed two-bedroom, two-bathroom manufactured home in Winter Haven Oaks. A split-bedroom floor plan places the sleeping areas apart for added privacy, while the home's setting supports an easygoing indoor-outdoor lifestyle. Step outside to find a fig tree, orange tree,

  

  Chrissy Walter

  Sunset Home Sales

  5297 Laurel Oak Dr, Winter Haven, FL 33880
• 

  

  /26

  $2,175 Per Month

  • 4 Beds
  • 2.5 Baths
  • 1,880 Sq Ft
  • House for Rent

  6220 Botticella Blvd, Winter Haven, FL 33884

  Brand-new two-story home located in the sought-after Villamar community of Winter Haven. This residence offers 4 bedrooms, 2.5 bathrooms, a spacious loft, and a 2-car garage with approximately 1,880 square feet of living space.The open-concept floor plan seamlessly connects the living, dining, and kitchen areas, creating a functional layout for everyday living and entertaining. The kitchen

  

  Maritza Monzon

  INTERNATIONAL EXECUTIVE REALTY

  6220 Botticella Blvd, Winter Haven, FL 33884
• 

  /2

  $305,000

  Sold Dec 29, 2025

  435 Lanham Dr, Winter Haven, FL 33881

  • 4 Beds
  • 2 Baths
  • 1,847 Sq Ft
  • Built 2021

  Last Sold Summary

  • 12% Below List Price
  • $165/SF
  • 64 Days On Market

  Current Estimated Value $320,639

  Last Listing Agent Angie Poole REMAX EXPERTS

  435 Lanham Dr, Winter Haven, FL 33881
• 

  /2

  Est $154,396

  Not Listed For Sale

  705 Eagle Pond Dr, Winter Haven, FL 33884

  • 2 Beds
  • 2 Baths
  • 1,017 Sq Ft
  • Built 2000

  705 Eagle Pond Dr, Winter Haven, FL 33884

  Last Sold Summary

  • 6 Days On Market

  Last Listing Agent JP Gutierrez EXP REALTY LLC

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