Winter Haven, FL Homes

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  $47,990

  • 2 Beds
  • 2 Baths

  293 Alpine Dr, Winter Haven, FL 33881

  Discover your retreat in the heart of Central Florida! This **2-bedroom, 2-bathroom** furnished manufactured home is nestled within **Swiss Village**, an active **55+ retirement community** on beautiful **Lake Henry**. Move in with ease - this home comes furnished minus just a few personal items, so you can start enjoying the Florida lifestyle right away. Recent upgrades bring peace of mind,

  

  Chrissy Walter

  Sunset Home Sales

  293 Alpine Dr, Winter Haven, FL 33881
• Explore Winter Haven

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  /26

  Starting at $1,499 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

  $379,000

  Sold Jul 22, 2026

  3060 Royal St, Winter Haven, FL 33884

  • 4 Beds
  • 2 Baths
  • 1,829 Sq Ft
  • Built 2023

  Last Sold Summary

  • $207/SF
  • 7 Days On Market

  Current Estimated Value $376,565

  Last Listing Agent Mabel Vassallo CENTURY 21 MYERS REALTY

  3060 Royal St, Winter Haven, FL 33884
• 

  

  /2

  Est $238,017

  Not Listed For Sale

  1825 Wallace Manor Ln, Winter Haven, FL 33880

  • 3 Beds
  • 2 Baths
  • 1,184 Sq Ft
  • Built 2018

  1825 Wallace Manor Ln, Winter Haven, FL 33880

  Last Sold Summary

  • 42 Days On Market
• 

  

  

  /33

  $214,900

  $20K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,131 Sq Ft

  2026 Kings Crossing SW, Winter Haven, FL 33880

  WELCOME HOME TO STONEBRIDGE! Step through your private, custom-gated Courtyard into a beautifully updated Stonebridge Patio Home that is truly MOVE-IN-READY! NEWER ROOF (2024), NEWER ELECTRIC PANEL (2024), NEWER WINDOWS AND SLIDERS (2022), NEW GUTTERS & DOWNSPOUTS (2026). This fabulous property is located in FEMA Zone X, a low-risk flood zone. From the moment you enter, you'll be impressed by the

  

  Kitty Mark

  COLDWELL BANKER REALTY

  2026 Kings Crossing SW, Winter Haven, FL 33880
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  $2,000 Per Month

  • 3 Beds
  • 2 Baths
  • 1,690 Sq Ft
  • House for Rent

  624 Honey Bell Rd, Winter Haven, FL 33880

  Welcome to 624 Honey Bell Road in the desirable Squires Grove community of Winter Haven! Built in 2022, this move-in ready 3-bedroom, 2-bath home offers the perfect blend of modern design, open living spaces, and everyday comfort. Step inside to discover a bright and inviting open-concept floor plan featuring tile flooring in the main living areas, abundant natural light, and a spacious living

  

  David Hartigan

  JASON MITCHELL REAL ESTATE FLO

  624 Honey Bell Rd, Winter Haven, FL 33880
• 

  /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 $263,046

  Last Listing Agent Ashley Lopez KELLER WILLIAMS REALTY SMART 1

  409 Lake Ned Rd, Winter Haven, FL 33884
• 

  /2

  Not Listed For Sale

  6508 Oak Hammock Ln, Winter Haven, FL 33884

  • 3 Beds
  • 2 Baths
  • 1,863 Sq Ft
  • Built 1998

  6508 Oak Hammock Ln, Winter Haven, FL 33884

  Last Sold Summary

  • 143 Days On Market
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  /52

  $54,990

  $5K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,560 Sq Ft

  158 Sago Palm Way, Winter Haven, FL 33880

  Discover retirement retreat in this charming 2-bedroom, 2-bathroom double-wide manufactured home, nestled within the sought-after Winter Haven Oaks - a gated 55+ active adult community brimming with small-town charm and Florida sunshine. Situated on a corner lot, this home features a spacious double carport, a relaxing lanai, and a bonus enclosed room with glass windows - ideal for morning coffee

  

  Chrissy Walter

  Sunset Home Sales

  158 Sago Palm Way, 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

  $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 $257,772

  Last Listing Agent Robert Jones OFFERPAD BROKERAGE FL, LLC

  565 Terranova Cir, Winter Haven, FL 33884
• 

  /2

  Est $143,948

  Not Listed For Sale

  1740 Inman Dr NW, Winter Haven, FL 33881

  • 3 Beds
  • 1 Bath
  • 805 Sq Ft
  • Built 1961

  1740 Inman Dr NW, Winter Haven, FL 33881

  Last Sold Summary

  • 6 Days On Market
• 

  

  /38

  $265,000

  • 3 Beds
  • 2 Baths
  • 1,678 Sq Ft

  1406 Meadow Dr NE, Winter Haven, FL 33881

  Spacious Single-Story Block Home with Endless Potential! Nestled in a quiet, established neighborhood close to Polk State College with no HOA, this solid single-story block home immediately catches the eye with its charming blend of stucco and natural multi-colored stone accents. Boasting 1,678 square feet of comfortable living space (2,527 square feet total), the interior features a generously

  

  Twanna Dewdney

  LA ROSA REALTY PRESTIGE

  1406 Meadow Dr NE, Winter Haven, FL 33881
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  /30

  $1,300 Per Month

  • 2 Beds
  • 1 Bath
  • 775 Sq Ft
  • Townhouse for Rent

  5667 Struthers Ct, Winter Haven, FL 33884

  Clean and cozy 2-bedroom, 1-bathroom duplex in southeast Winter Haven. Featuring wood laminate flooring in living areas and bedrooms, with ceramic tile flooring in the kitchen and bathroom. Kitchen equipped with newerKitchen cabinets and comes with range/oven, refrigerator, and washer/dryer hookups in utility closet. Both bedrooms of ample size with ceiling fans. Recently remodeled bathroom with

  

  CarLee Marchetti

  STAR REALTY OF WINTER HAVEN

  5667 Struthers Ct, 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 $305,992

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

  4507 Rapallo Ave, Winter Haven, FL 33884
• 

  /2

  Est $323,185

  Not Listed For Sale

  491 Majestic Gardens Blvd, Winter Haven, FL 33880

  • 5 Beds
  • 2 Baths
  • 2,018 Sq Ft
  • Built 2012

  491 Majestic Gardens Blvd, Winter Haven, FL 33880

  Last Sold Summary

  • 22 Days On Market
• 

  

  /65

  $494,999

  $5K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,333 Sq Ft

  408 Talamone Dr, Winter Haven, FL 33884

  This well-maintained 4-bedroom, 3-bathroom pool home is located in the sought-after gated community of Tuscany at Winterset, offering both comfort and style in a prime setting. Inside, you’ll find an inviting layout highlighted by solid surface countertops, elegant tray ceilings, and detailed crown molding that adds a refined touch throughout the living spaces. Major updates provide peace of

  

  Tony Insua Jr.

  LOCKHART & ASSOCIATES INC

  408 Talamone Dr, Winter Haven, FL 33884
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  /39

  Starting at $1,295 Per Month

  • 1 - 2 Beds

  200 Avenue C SW, Winter Haven, FL 33880

  Discover a living experience that moves with you. At Raindance, we have reimagined the modern residence as a sanctuary of light and fluid design. Each floor plan is a masterclass in spatial harmony, meticulously curated to balance expansive windows with intimate, designer-led interiors. Our commitment to excellence is woven into the very bones of the building, exceeding the highest energy

  Raindance

  

  200 Avenue C SW, 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 $323,929

  Last Listing Agent Pedro Fernandez Salvador CONTEMPORARY REALTY GROUP

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

  /2

  Est $344,872

  Not Listed For Sale

  1497 Leamington Ln, Winter Haven, FL 33884

  • 4 Beds
  • 2.5 Baths
  • 2,405 Sq Ft
  • Built 2024

  1497 Leamington Ln, Winter Haven, FL 33884

  Last Sold Summary

  • 10 Days On Market
• 

  

  /26

  $250,000

  $20K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 1,527 Sq Ft

  940 Oleander Dr SE, Winter Haven, FL 33880

  Auction Property. Ranch-style home offering 2 bedrooms and 1.5 bathrooms with a spacious living room and a good-sized yard. Features include a durable metal roof, RV electrical hookups, and a chicken coop. Some updates in the kitchen. Short Sale subject to lender approval.

  

  David Hartigan

  JASON MITCHELL REAL ESTATE FLO

  940 Oleander Dr SE, Winter Haven, FL 33880
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  /44

  $1,400 Per Month

  • 2 Beds
  • 2 Baths
  • 930 Sq Ft
  • Condo for Rent

  8302 Waterview Way, Winter Haven, FL 33884

  Cute and clean downstairs end unit in Winterset, a gated community. Features wood laminate flooring in living area and bedrooms and ceramic tile in the wet areas. Open floor plan, kitchen with breakfast bar overlooking living room with mirror wall and dining area. Master bedroom has sliding glass doors to a private 6x7 screened in patio. Master suite includes walk-in closet, stackable washer &

  

  CarLee Marchetti

  STAR REALTY OF WINTER HAVEN

  8302 Waterview Way, Winter Haven, FL 33884
• 

  

  /16

  $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 $256,000

  Lennar Peace Creek Reserve - Serenity

  3040 Captain Jax Way, Winter Haven, FL 33884
• 

  /2

  Est $285,270

  Not Listed For Sale

  4482 Rapallo Ave, Winter Haven, FL 33884

  • 3 Beds
  • 2.5 Baths
  • 1,568 Sq Ft
  • Built 2025

  4482 Rapallo Ave, Winter Haven, FL 33884

  Last Sold Summary

  • 21 Days On Market
• 

  

  /43

  $49,990

  $5K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft

  5236 Grand Cypress Ct, Winter Haven, FL 33880

  Discover this 2-bedroom, 2-bathroom manufactured home nestled in the heart of Winter Haven Oaks, a 55+ gated community in Winter Haven, FL. This estate sale offers an incredible opportunity for a quick close - and everything in the home stays, including a golf cart ready for your next neighborhood adventure! Stay active and social with an impressive lineup of amenities, including two clubhouses,

  

  Chrissy Walter

  Sunset Home Sales

  5236 Grand Cypress Ct, Winter Haven, FL 33880
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  /54

  Starting at $1,460 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

  $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 $282,278

  Last Listing Agent Cindy Thornton AGILE GROUP REALTY

  6654 Crescent Loop, Winter Haven, FL 33884
• 

  /2

  Est $318,455

  Not Listed For Sale

  2155 Chris Dr, Winter Haven, FL 33884

  • 4 Beds
  • 3 Baths
  • 2,174 Sq Ft
  • Built 2025

  2155 Chris Dr, Winter Haven, FL 33884

  Last Sold Summary

  • 4 Days On Market
• 

  

  /15

  $240,000

  $59K PRICE DROP Under Contract

  • 3 Beds
  • 2 Baths
  • 1,732 Sq Ft

  3180 Country Club Cir, Winter Haven, FL 33881

  Under contract-accepting backup offers. Short Sale. APPROVED SHORT SALE AT PRICE! CHAPTER 7 BANKRUPTCY - Located In The Country Walk Community, This 2019 Built Home At 3180 Country Club Cir, Winter Haven, FL 33881 Features The Popular DR Horton Aria Floor Plan Offering 3 Bedrooms, 2 Bathrooms, & 1,672 Sq Ft Of Living Space. This Home Offers an Open Concept Layout With A Spacious Living Area,

  

  Jon McCall PA

  DALTON WADE INC

  3180 Country Club Cir, Winter Haven, FL 33881
• 

  

  /56

  $2,300 Per Month

  • 4 Beds
  • 2.5 Baths
  • 1,942 Sq Ft
  • House for Rent

  1504 Hummingbird Rd, Winter Haven, FL 33884

  Welcome to your slice of Florida paradise! This almost-new, fully furnished 4-bedroom, 2.5-bath home sits beautifully on a spacious corner lot with a lush yard—perfect for relaxing or entertaining. Designed with modern finishes throughout, every room feels fresh and inviting. The home boasts a large 2-car garage equipped with a Tesla charger, making it ideal for eco-conscious residents. Enjoy the

  

  Matthew Stanley

  The Keyes Company

  1504 Hummingbird Rd, 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 $308,018

  Last Listing Agent Angie Poole REMAX EXPERTS

  435 Lanham Dr, Winter Haven, FL 33881
• 

  /2

  Est $324,332

  Not Listed For Sale

  2203 Chris Dr, Winter Haven, FL 33884

  • 5 Beds
  • 3 Baths
  • 2,451 Sq Ft
  • Built 2025

  2203 Chris Dr, Winter Haven, FL 33884

  Last Sold Summary

  • 14 Days On Market
• 

  

  /22

  $35,000

  $13K PRICE DROP

  • 2 Beds
  • 2 Baths

  625 Century Dr, Winter Haven, FL 33881

  This 940 sq ft home offers an open floor plan and a bright Florida room at the front of the house-perfect for relaxing or morning coffee. Recent improvements include new plumbing throughout (10/2023), a newer roof (2023), and an AC system installed around 2020. The home features convenient stackable inside laundry and a large shed for extra storage. A wonderful opportunity to make this home your

  

  Cindy Minnick

  Sun Resales, Inc.

  625 Century Dr, Winter Haven, FL 33881
• 

  

  /36

  Starting at $1,319 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

  $138,000

  Sold Jul 29, 2025

  109 2nd Jpv St, Winter Haven, FL 33880

  • 2 Beds
  • 1 Bath
  • 1,160 Sq Ft
  • Built 1958

  Last Sold Summary

  • 8% Below List Price
  • $119/SF
  • 7 Days On Market

  Current Estimated Value $164,214

  Last Listing Agent Nick Whitehouse RE/MAX PRIME PROPERTIES

  109 2nd Jpv St, Winter Haven, FL 33880
• 

  /2

  Not Listed For Sale

  103 Hamlin St, Winter Haven, FL 33880

  • 5 Beds
  • 2 Baths
  • 1,620 Sq Ft
  • Built 2016

  103 Hamlin St, Winter Haven, FL 33880

  Last Sold Summary

  • 96 Days On Market
• 

  

  /60

  $349,999

  $50K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,524 Sq Ft

  1522 Eckart Dr, Winter Haven, FL 33881

  This updated 3-bedroom, 2-bath home offers comfort, functionality, and plenty of outdoor space to enjoy Florida living. Inside, you’ll love the spacious open floor plan featuring a Great Room, dining area, and family room combination with cathedral ceilings, wood burning fireplace, laminate wood flooring, and abundant recessed lighting. French doors from the dining room lead to an open patio and

  

  Russ Rhoads

  EXP REALTY LLC

  1522 Eckart Dr, Winter Haven, FL 33881
• 

  

  /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

  $325,000

  Sold Nov 04, 2025

  3828 Eloise Estates Ct, Winter Haven, FL 33881

  • 4 Beds
  • 2 Baths
  • 1,867 Sq Ft
  • Built 2014

  Last Sold Summary

  • 2% Below List Price
  • $174/SF
  • 132 Days On Market

  Current Estimated Value $313,526

  Last Listing Agent Lamanda Jones CENTURY 21 WATSON & MYERS REALTY

  3828 Eloise Estates Ct, Winter Haven, FL 33881
• 

  /2

  Not Listed For Sale

  0 Hwy 542 W, Winter Haven, FL 33880

  0 Hwy 542 W, Winter Haven, FL 33880

  Last Sold Summary

  • 7 Days On Market

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