49,148

Winter Haven, FL Homes

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  • /100

    $1,799,900

    $150K PRICE DROP
    • 4 Beds
    • 4 Baths
    • 4,708 Sq Ft

    13 Bogey Dr, Winter Haven, FL 33881

    Opportunities like this are nearly extinct. Just minutes from Winter Haven Country Club, this remarkable estate offers 10.98 acres of privacy, natural beauty, and flexibility in one of Winter Haven’s most coveted and tightly held locations—where land, space, and convenience rarely coexist.The 3,800 sq ft main residence has been completely remodeled with a refined, modern vision that blends

    Agent Photo

    Brock Jennings

    THE MARKET REALTY COMPANY

    13 Bogey Dr, Winter Haven, FL 33881
  • /35

    $2,000 Per Month

    • 4 Beds
    • 2 Baths
    • 1,851 Sq Ft
    • House for Rent

    397 Corso Loop, Winter Haven, FL 33884

    Elegant Villamar Residence | 4 Bedrooms | 2 Baths | No Carpet | $2,100/Month. Welcome to this beautifully maintained four-bedroom, two-bath residence in Villamar. Built in 2021, this inviting home features an open-concept design with NO CARPET throughout, creating a clean, sophisticated feel and effortless maintenance. The spacious living and dining areas flow seamlessly into a well-appointed

    397 Corso Loop, Winter Haven, FL 33884
  • /2

    $260,000

    Sold Jul 29, 2026

    1150 High Seas St, Winter Haven, FL 33880

    • 3 Beds
    • 2 Baths
    • 1,702 Sq Ft
    • Built 2013

    Last Sold Summary

    • 13% Below List Price
    • $153/SF
    • 209 Days On Market

    Current Estimated Value $276,354

    Last Listing Agent Blake Keathley EVERYSTATE INC.

    1150 High Seas St, Winter Haven, FL 33880
    • /42

      Est $220,097

      Not Listed For Sale

      1572 Vienna Square Dr, Winter Haven, FL 33884

      • 2 Beds
      • 2 Baths
      • 1,391 Sq Ft
      • Built 2013
      1572 Vienna Square Dr, Winter Haven, FL 33884

      Last Sold Summary

      • 18 Days On Market

      Last Listing Agent Marti Sutton CENTURY 21 WATSON & MYERS REALTY

  • /43

    $455,000

    • 6 Beds
    • 2 Baths
    • 1,944 Sq Ft

    1830 2nd St NW Unit A, Winter Haven, FL 33881

    Calling all investors and house-hackers! Welcome to 1830 2nd St NW, a fantastic multi-family investment opportunity located right in the heart of Winter Haven. This well-maintained duplex features two spacious, mirror-image units, each offering a highly desirable 3-bedroom, 1-bathroom layout perfect for maximizing rental income and attracting long-term tenants! Both units boast bright,

    Agent Photo

    John Gomez

    EXP REALTY LLC

    1830 2nd St NW Unit A, Winter Haven, FL 33881
  • /42

    $1,450 Per Month

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

    704 Eagle Pond Dr Unit 7D, Winter Haven, FL 33884

    Lovely GROUND FLOOR Eagle Pond condominium in the highly sought-after gated community of Cypresswood Golf and Country Club. 10-foot high ceilings, complimenting the open concept living area complete with expansive living and dining areas, including a kitchen breakfast bar. All NEW luxury vinyl flooring, NEW windows and sliding glass patio door, NEW kitchen countertops, and fresh interior paint.

    Kayly Malinas JOHN WOOD REALTY, INC.

    704 Eagle Pond Dr Unit 7D, Winter Haven, FL 33884
  • /2

    $255,000

    Sold Jan 08, 2026

    6191 Grey Heron Dr, Winter Haven, FL 33881

    • 3 Beds
    • 2 Baths
    • 1,711 Sq Ft
    • Built 2017

    Last Sold Summary

    • 4% Below List Price
    • $149/SF
    • 16 Days On Market

    Current Estimated Value $263,420

    Last Listing Agent Lesley Guarino CITRAVEST MANAGEMENT LLC

    6191 Grey Heron Dr, Winter Haven, FL 33881
    • /2

      Est $278,904

      Not Listed For Sale

      5801 Forest Ridge Dr, Winter Haven, FL 33881

      • 4 Beds
      • 2 Baths
      • 1,788 Sq Ft
      • Built 2017
      5801 Forest Ridge Dr, Winter Haven, FL 33881

      Last Sold Summary

      • 80 Days On Market

      Last Listing Agent Leslee Davis DALTON WADE INC

  • /60

    $35,000

    $20K PRICE DROP
    • 3 Beds
    • 2 Baths

    269 Hummingbird Ln, Winter Haven, FL 33884

    Enjoy the best of Florida living in this spacious and beautifully maintained 2-bedroom, 2-bath home located in a private community with exclusive lake access. This inviting property offers comfort, convenience, and an unbeatable location perfect for full-time residents, vacationers, or seasonal living. Ideally situated near shopping, restaurants, entertainment, and everyday conveniences, you'll

    Agent Photo

    Glenn Fogg

    FOGG MOBILE HOME SALES LLC

    269 Hummingbird Ln, Winter Haven, FL 33884
  • /21

    $1,550 Per Month

    • 2 Beds
    • 2 Baths
    • 1,074 Sq Ft
    • House for Rent

    204 Chaucer Ln, Winter Haven, FL 33884

    Centrally located 2 bedroom 2 bath. This home has been updated with new flooring and paint throughout. 2 car garage, screen lanai, fenced yard.**This home comes with high speed internet up to 1 Gig at an exclusive group rate of $60/month (In addition to advertised rent), and includes 24/7 premium support and setup to help get you connected at move-in**Administration Fee:Upon

    204 Chaucer Ln, Winter Haven, FL 33884
  • /2

    $312,900

    Sold Dec 24, 2025

    737 Bayside Blvd, Winter Haven, FL 33881

    • 4 Beds
    • 2 Baths
    • 1,819 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • $172/SF
    • 14 Days On Market

    Current Estimated Value $318,964

    Highland Homes Harbor at Lake Henry - Single-Family Homes

    737 Bayside Blvd, Winter Haven, FL 33881
    • /2

      Est $298,634

      Not Listed For Sale

      2487 Salzburg Loop, Winter Haven, FL 33884

      • 3 Beds
      • 2 Baths
      • 1,914 Sq Ft
      • Built 2016
      2487 Salzburg Loop, Winter Haven, FL 33884

      Last Sold Summary

      • 8 Days On Market

      Last Listing Agent Wanda Dicks COLDWELL BANKER REALTY

  • /12

    $209,900

    • Land
    • 32,670 Sq Ft
    • $279,867 per Acre

    0 Eloise Loop Rd Unit MFRP4939471, Winter Haven, FL 33884

    OSPREY ESTATES IS A SMALL, GATED COMMUNITY LOCATED IN BEAUTIFUL SE WINTER HAVEN, FLORIDA. THE COMMUNITY HAS A TOTAL OF FOUR LOTS--THREE HAVE UPSCALE RESIDENCES AND THIS IS THE LAST ONE AVAILABLE. THE LOT IS .75 ACRE. THIS LOCATION IS CLOSE TO SHOPPING, MULTIPLE RESTAURANTS, LEGOLAND AND BOTH TAMPA AND ORLANDO. HOA REQUIRES A MINIMUM 3,500 SQ FEET OF LIVING AND A MAXIMUM 5,500 SQ FEET OF

    Agent Photo

    Brenda J. Quinn

    QUINN & COMPANY REALTORS, LLC

    0 Eloise Loop Rd Unit MFRP4939471, Winter Haven, FL 33884
  • /35

    $1,450 Per Month

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

    1105 Eagle Pond Dr Unit 11E, Winter Haven, FL 33884

    Second floor Eagle Pond condominium in the highly desirable 24-hour guard-gated community of Cypresswood Golf and Country Club. High ceilings, breakfast bar, and open-concept living area are just a few features this property offers. The spacious primary bedroom features an en suite bathroom while both bedrooms offer walk-in closets. Additional linen storage exists in the main bedroom and hallway,

    Kayly Malinas JOHN WOOD REALTY, INC.

    1105 Eagle Pond Dr Unit 11E, Winter Haven, FL 33884
  • /2

    $160,000

    Sold Dec 11, 2025

    505 Avenue G SE, Winter Haven, FL 33880

    • 3 Beds
    • 3 Baths
    • 1,786 Sq Ft
    • Built 1955

    Last Sold Summary

    • 18% Below List Price
    • $90/SF
    • 73 Days On Market

    Current Estimated Value $202,094

    Last Listing Agent Reggie Ward PREMIER REALTY OF TAMPA

    505 Avenue G SE, Winter Haven, FL 33880
    • /9

      Est $220,313

      Not Listed For Sale

      Unlisted Address

      • 3 Beds
      • 2 Baths
      • 1,322 Sq Ft
      • Built 2022
      Unlisted Address

      Last Sold Summary

      • 239 Days On Market

      Last Listing Agent Robin Pascale KELLER WILLIAMS REALTY

  • /100

    $599,900

    • 3 Beds
    • 2 Baths
    • 2,591 Sq Ft

    5365 Hogan Ln, Winter Haven, FL 33884

    Welcome to the next exciting chapter of your life in Lake Ashton, Central Florida’s premier 55+ active-adult community, where this immaculately maintained three-bedroom, two-bath home with a den offers exceptional comfort and elegance, including a beautiful primary suite with its own relaxing sitting room and a sparkling 71⁄2' x 36' bromine pool awaiting your enjoyment. From the striking stone

    Agent Photo

    Brad Kirwan

    GLOBAL LIFESTYLE LLC

    5365 Hogan Ln, Winter Haven, FL 33884
  • /9

    $1,350 Per Month

    • 2 Beds
    • 1.5 Baths
    • 1,000 Sq Ft
    • House for Rent

    638 W Central Ave, Winter Haven, FL 33880

    ABOUT THE HOMEUpdated downstairs apartment at 638 W Central Ave featuring vinyl flooring throughout, no carpet, an in-unit washer and dryer, and a convenient 2-bedroom/1.5-bath layout. Located within a fenced triplex property near Downtown Winter Haven with convenient access to dining, shopping, medical offices, parks, and everyday amenities.BEFORE SCHEDULINGPlease schedule a

    638 W Central Ave, Winter Haven, FL 33880
  • /2

    $340,000

    Sold Sep 04, 2026

    1819 Sandhill Ln, Winter Haven, FL 33884

    • 3 Beds
    • 2 Baths
    • 2,045 Sq Ft
    • Built 2002

    Last Sold Summary

    • 4% Below List Price
    • $166/SF
    • 43 Days On Market

    Last Listing Agent Lori Roberts GOLD HEART REALTY LLC

    1819 Sandhill Ln, Winter Haven, FL 33884
    • /52

      Est $289,888

      Not Listed For Sale

      1359 Buckeye Trace Blvd, Winter Haven, FL 33881

      • 4 Beds
      • 2 Baths
      • 1,668 Sq Ft
      • Built 2018
      1359 Buckeye Trace Blvd, Winter Haven, FL 33881

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Pedro Perez, Jr DALTON WADE INC

  • /2

    $328,999

    New Construction $1K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,226 Sq Ft

    5386 San Pietro Dr, Winter Haven, FL 33884

    5386 San Pietro Drive, Winter Haven, FL 33884

    Builder Photo

    Casa Fresca Homes

    Builder

    5386 San Pietro Dr, Winter Haven, FL 33884
  • /41

    $1,650 Per Month

    • 3 Beds
    • 1 Bath
    • 1,100 Sq Ft
    • House for Rent

    204 6th Jpv St, Winter Haven, FL 33880

    Three bedroom, one bathroom home located in Winter Haven. This property features a roof installed in 2025 and an AC system installed in 2025 for energy efficiency and year round comfort. The interior floor plan includes a remodeled kitchen, a remodeled bathroom, and low maintenance ceramic tile flooring throughout with no carpet. Enjoy a functional layout with bright living spaces and a spacious

    Juan Corrales DALTON WADE INC

    204 6th Jpv St, Winter Haven, FL 33880
  • /2

    $110,000

    Sold Oct 13, 2025

    6501 Raintree Ln NE, Winter Haven, FL 33881

    • 2 Beds
    • 2 Baths
    • 1,012 Sq Ft
    • Built 1985

    Last Sold Summary

    • $109/SF
    • 19 Days On Market

    Last Listing Agent Corinna Weaver CROSBY & ASSOCIATES, INC.

    6501 Raintree Ln NE, Winter Haven, FL 33881
    • /17

      Est $276,790

      Not Listed For Sale

      4729 Osprey Way, Winter Haven, FL 33881

      • 3 Beds
      • 2 Baths
      • 1,576 Sq Ft
      • Built 2017
      4729 Osprey Way, Winter Haven, FL 33881

      Last Sold Summary

      • 32 Days On Market

      Last Listing Agent Jay Scharff KELLER WILLIAMS REALTY SMART 1

  • /38

    $80,000

    • 3 Beds
    • 2 Baths
    • 1,330 Sq Ft

    333 Lake Howard Dr NW Unit 304B, Winter Haven, FL 33880

    Top-floor condo with INCREDIBLE lake views in the desirable 55+ community of Imperial Harbours on Lake Howard! This three-bedroom, two-bath condo offers tons of potential and is ready for your personal touches and a little TLC. The kitchen features a convenient pass-through window overlooking the dining and living areas, creating an open and functional layout. The spacious primary suite includes

    Agent Photo

    Amy Reynolds

    LOCKHART & ASSOCIATES INC

    333 Lake Howard Dr NW Unit 304B, Winter Haven, FL 33880
  • /20

    $2,950 Per Month

    • 5 Beds
    • 3 Baths
    • 2,670 Sq Ft
    • House for Rent

    2545 Partridge Dr, Winter Haven, FL 33884

    ABOUT THE HOMEWelcome to this spacious 5-bedroom, 3-bath executive pool home in the prestigious gated community of Eloise Pointe Estates. Offering 2,670 square feet on a large 0.67-acre lot, the home features fresh paint, newly renovated cabinetry, tile and luxury vinyl plank flooring throughout—no carpet—oversized closets, and a three-car side-entry garage. Enjoy the screened-in pool,

    2545 Partridge Dr, Winter Haven, FL 33884
  • /2

    $78,000

    Sold Apr 13, 2026

    211 Sweet Cir, Winter Haven, FL 33884

    • 2 Beds
    • 2 Baths
    • 1,274 Sq Ft
    • Built 1986

    Last Sold Summary

    • 29% Below List Price
    • $61/SF
    • 332 Days On Market

    Last Listing Agent Brian Cox KELLER WILLIAMS REALTY SMART 1

    211 Sweet Cir, Winter Haven, FL 33884
    • /2

      Est $1,017,769

      Not Listed For Sale

      4717 Emerald Palms Ct, Winter Haven, FL 33884

      • 5 Beds
      • 4.5 Baths
      • 4,579 Sq Ft
      • Built 2016
      4717 Emerald Palms Ct, Winter Haven, FL 33884

      Last Sold Summary

      • 34 Days On Market

      Last Listing Agent Michael Stone THE STONES REAL ESTATE FIRM

  • /20

    $54,000

    • 2 Beds
    • 2 Baths
    • 940 Sq Ft

    757 Century Ln, Winter Haven, FL 33881

    Welcome home to this charming and well-maintained 2-bedroom, 2-bath home located in a welcoming 55+ community. Offering comfortable living spaces, plenty of natural light, and several important updates, this home is ready for its next owner to enjoy. The spacious living room provides plenty of room for relaxing and entertaining, while the adjacent dining area flows naturally into the

    Agent Photo

    Cindy Minnick

    Sun Resales, Inc.

    757 Century Ln, Winter Haven, FL 33881
  • /25

    $1,650 Per Month

    • 2 Beds
    • 2 Baths
    • 1,213 Sq Ft
    • House for Rent

    253 W Lake Ina Dr, Winter Haven, FL 33884

    Limited-time offer: Receive half off the second month’s rent! No HOA! Pet Friendly!Welcome to this beautifully updated 2-bedroom, 2-bathroom single-family home featuring a spacious driveway, an open floor plan, and an oversized Florida room that's perfect for relaxing or entertaining year-round.This home boasts luxury vinyl flooring throughout and tastefully upgraded bathrooms. The bright

    Katrina Anarumo RENT A FLORIDA HOME

    253 W Lake Ina Dr, Winter Haven, FL 33884
  • /2

    $259,990

    Sold Apr 24, 2026

    2735 Gladiola Rd, Winter Haven, FL 33884

    • 3 Beds
    • 2.5 Baths
    • 1,758 Sq Ft
    • Built 2025

    Last Sold Summary

    • 2% Below List Price
    • $148/SF
    • 76 Days On Market

    Current Estimated Value $258,974

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

    2735 Gladiola Rd, Winter Haven, FL 33884
    • /2

      Est $295,417

      Not Listed For Sale

      1069 Brenton Manor Dr, Winter Haven, FL 33881

      • 4 Beds
      • 2 Baths
      • 1,841 Sq Ft
      • Built 2015
      1069 Brenton Manor Dr, Winter Haven, FL 33881

      Last Sold Summary

      • 44 Days On Market

      Last Listing Agent Rey Andrade THE PROPERTY PROS REAL ESTATE, INC

  • /13

    $323,965

    New Construction
    • 3 Beds
    • 2 Baths
    • 1,549 Sq Ft

    2240 Labrador Loop, Winter Haven, FL 33884

    Pre-Construction. To be built. Welcome to Ashton Covey in Winter Haven! The Adeline single-family home is the next level of great living. Enter through the inviting front porch or attached 2-car garage into the large foyer. Inside, laughter comes from the spacious great room, the heart of your home. The adjoining gourmet kitchen, with large center island and connected dining space, can flow

    Agent Photo

    William Maltbie

    MALTBIE REALTY GROUP

    2240 Labrador Loop, Winter Haven, FL 33884
  • /22

    $1,399 Per Month

    • 3 Beds
    • 1 Bath
    • 1,420 Sq Ft
    • House for Rent

    120 3rd Jpv St, Winter Haven, FL 33880

    Enjoy the comfort and ease of living with ALL TILE flooring throughout the home. Need a little extra space for relaxation or entertainment? This property boasts a generously sized family bonus room, perfect for unwinding after a long day or hosting gatherings with friends and family.Beyond the kitchen appliances, this home also offers washer/dryer hookups in the laundry area, providing

    120 3rd Jpv St, Winter Haven, FL 33880
  • /5

    $244,990

    Sold Jan 09, 2026

    207 Turtle Bay Ave, Winter Haven, FL 33881

    • 3 Beds
    • 2 Baths
    • 1,604 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • $153/SF
    • 30 Days On Market

    Current Estimated Value $243,553

    Highland Homes Harbor at Lake Henry - Townhomes

    207 Turtle Bay Ave, Winter Haven, FL 33881
    • /32

      Est $304,193

      Not Listed For Sale

      1591 Normandy Heights Blvd, Winter Haven, FL 33880

      • 4 Beds
      • 2 Baths
      • 1,788 Sq Ft
      • Built 2014
      1591 Normandy Heights Blvd, Winter Haven, FL 33880

      Last Sold Summary

      • 9 Days On Market

      Last Listing Agent Deanna Stone THE STONES REAL ESTATE FIRM

  • /21

    $350,165

    New Construction
    • 4 Beds
    • 2 Baths
    • 2,021 Sq Ft

    2236 Labrador Loop, Winter Haven, FL 33884

    Pre-Construction. To be built. Welcome to Ashton Covey in Winter Haven! The Panama single-family home is what you always pictured for yourself. Step in from the 2-car garage or front porch and pass the first of 3 spacious bedrooms and a full bath with double vanity. A versatile flex space can be used as an office, a study, or a 4th bedroom. In the dining area, prepare to be wowed. This space is

    Agent Photo

    William Maltbie

    MALTBIE REALTY GROUP

    2236 Labrador Loop, Winter Haven, FL 33884
  • /16

    $1,899 Per Month

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

    4214 Roberta Dr, Winter Haven, FL 33881

    Move-in ready 3 bedroom, 2 bath home in the Buckeye Ridge community of Winter Haven with electricity included in the rent thanks to solar panels. Built in 2018 with 1,690 square feet on a single level, the home has an open layout connecting the living and dining areas to a kitchen with generous cabinet space. The primary bedroom offers a private bath and walk-in closet, and both additional

    Jose Arroyo Diaz EXP REALTY LLC

    4214 Roberta Dr, Winter Haven, FL 33881
  • /2

    $272,000

    Sold Mar 30, 2026

    5750 Harbor Isle Blvd, Winter Haven, FL 33884

    • 3 Beds
    • 2 Baths
    • 1,238 Sq Ft
    • Built 2002

    Last Sold Summary

    • 10% Above List Price
    • $220/SF
    • 7 Days On Market

    Current Estimated Value $255,592

    Last Listing Agent Ryan Odenweller RE/MAX HERITAGE PROFESSIONALS

    5750 Harbor Isle Blvd, Winter Haven, FL 33884
    • /3

      Est $284,887

      Not Listed For Sale

      4749 Osprey Way, Winter Haven, FL 33881

      • 4 Beds
      • 2 Baths
      • 1,825 Sq Ft
      • Built 2017
      4749 Osprey Way, Winter Haven, FL 33881

      Last Sold Summary

      • 169 Days On Market

      Last Listing Agent Brian Stephens EXP REALTY LLC

Showing Results 481 - 520, Page 13 of 18

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