49,151

Winter Haven, FL Homes

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  • /12

    $295,000

    • 3 Beds
    • 2 Baths
    • 1,925 Sq Ft

    706 Avenue I NE, Winter Haven, FL 33881

    Own a private oasis in the heart of Winter Haven! This beautiful 3-bedroom, 2-bathroom home features 1,941 square feet of comfortable living space. It rests on an extra-large .41-acre lot. That gives you plenty of space to relax and enjoy outdoor living and gardening. The property features a large open pool for beating the Florida heat, with a pool room and screened patio. The home also features

    Agent Photo

    Steve Lockhart

    LOCKHART & ASSOCIATES INC

    706 Avenue I NE, Winter Haven, FL 33881
  • /15

    $2,000 Per Month

    • 3 Beds
    • 2 Baths
    • 1,567 Sq Ft
    • House for Rent

    4736 Mandolin Loop, Winter Haven, FL 33884

    Apply now or schedule your self-tour today and take the first step toward getting more than just a place to live. Rent with FirstKey Homes for a home that's right for you, plus professional service and maintenance, innovative resident programs, and more; that's the power of purple!This 3-bedroom, 2-bathroom rental home in Winter Haven, FL, might be the perfect fit for your lifestyle. See

    4736 Mandolin Loop, Winter Haven, FL 33884
  • /2

    $370,000

    Sold Jan 02, 2026

    905 Hillside Ct S, Winter Haven, FL 33881

    • 3 Beds
    • 2 Baths
    • 2,077 Sq Ft
    • Built 1986

    Last Sold Summary

    • 4% Below List Price
    • $178/SF
    • 27 Days On Market

    Current Estimated Value $379,579

    Last Listing Agent Tisha Talbot CENTURY 21 MYERS REALTY

    905 Hillside Ct S, Winter Haven, FL 33881
    • /2

      Est $317,347

      Not Listed For Sale

      4058 Island Lakes Dr, Winter Haven, FL 33881

      • 4 Beds
      • 2 Baths
      • 2,086 Sq Ft
      • Built 2015
      4058 Island Lakes Dr, Winter Haven, FL 33881

      Last Sold Summary

      • 36 Days On Market

      Last Listing Agent Niki Thomas-Schnyder UNITED COUNTRY SMITH & ASSOCIATES - NEWBERRY

  • /46

    $299,500

    $25K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,012 Sq Ft

    5638 Royal Hills St, Winter Haven, FL 33881

    WELCOME TO THIS WELL-KEPT PROPERTY WITH LOW HOA FEE. THIS IS A SPLIT PLAN FOUR BEDROOM/TWO BATH HOME. THE PROPERTY HAS A LIVING, DINING AND FAMILY ROOM. THE EAT-IN KITCHEN IS LIGHT AND BRIGHT. THERE IS AN INSIDE LAUNDRY ROOM. THE BEDROOMS ARE NICELY SIZED. VAULTED AND CATHEDRAL CEILINGS ALONG WITH NUMEROUS PLANT SHELVES ADD CHARACTER TO THIS HOME. THERE IS A SCREENED PORCH OFF THE FAMILY ROOM

    Agent Photo

    Brenda J. Quinn

    QUINN & COMPANY REALTORS, LLC

    5638 Royal Hills St, Winter Haven, FL 33881
  • /16

    $1,769 Per Month

    • 3 Beds
    • 2 Baths
    • 1,340 Sq Ft
    • House for Rent

    3111 Buckeye Point Dr, Winter Haven, FL 33881

    This home is professionally managed by Tricon, dedicated to creating exceptional rental experiences. Featuring 3 bedrooms, 2.0 bathrooms, and approximately 1,340 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 rental

    3111 Buckeye Point Dr, Winter Haven, FL 33881
  • /2

    $301,805

    Sold Feb 25, 2026

    3861 Giorgio Dr, Winter Haven, FL 33884

    • 4 Beds
    • 2 Baths
    • 1,840 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • $164/SF
    • 208 Days On Market

    Current Estimated Value $304,713

    Meritage Homes VillaMar - Signature Series

    3861 Giorgio Dr, Winter Haven, FL 33884
    • /2

      Not Listed For Sale

      6031 Grand Oaks Dr SE, Winter Haven, FL 33884

      • 2 Beds
      • 2 Baths
      • 1,272 Sq Ft
      • Built 1984
      6031 Grand Oaks Dr SE, Winter Haven, FL 33884

      Last Sold Summary

      • 287 Days On Market

      Last Listing Agent Kimberly Gay COLDWELL BANKER REALTY

  • /37

    $435,000

    • 3 Beds
    • 2 Baths
    • 1,572 Sq Ft

    795 Crosstower Dr, Winter Haven, FL 33880

    Built in 2023 and situated on 1.59 acres, this 3 bedroom, 2 bath home offers something increasingly hard to find in Winter Haven: a newer home with land, flexibility and NO HOA. Nearly 200 feet of street visibility along Hwy 540 creates a unique opportunity for a small business owner who understands the value of exposure. Imagine the visibility your brand could capture simply by parking your

    Agent Photo

    Veronica Bard

    LA ROSA REALTY PRESTIGE

    795 Crosstower Dr, Winter Haven, FL 33880
  • /16

    $1,900 Per Month

    • 4 Beds
    • 2 Baths
    • 2,284 Sq Ft
    • House for Rent

    557 Reddicks Cir, Winter Haven, FL 33884

    EXCITING NEWS: WE RECENTLY RENOVATED THIS HOME! IMPROVEMENTS INCLUDE: NEW HARD SURFACE COUNTERTOPS. APPLY TODAY OR ASK YOUR LEASING SPECIALIST FOR MORE DETAILS! Apply now or schedule your self-tour today and take the first step toward getting more than just a place to live. Rent with FirstKey Homes for a home that's right for you, plus professional service and

    557 Reddicks Cir, Winter Haven, FL 33884
  • /2

    $260,000

    Sold Dec 11, 2025

    1032 Cambridge Dr, Winter Haven, FL 33881

    • 4 Beds
    • 2 Baths
    • 1,500 Sq Ft
    • Built 2021

    Last Sold Summary

    • 863% Above List Price
    • $173/SF
    • 57 Days On Market

    Current Estimated Value $260,667

    Last Listing Agent Fredy Plazas FLORIDA REALTY INVESTMENTS

    1032 Cambridge Dr, Winter Haven, FL 33881
    • /2

      Not Listed For Sale

      6750 Kensington Dr NE, Winter Haven, FL 33881

      • 2 Beds
      • 2 Baths
      • 989 Sq Ft
      • Built 1983
      6750 Kensington Dr NE, Winter Haven, FL 33881

      Last Sold Summary

      • 71 Days On Market

      Last Listing Agent Laura Villardi COLDWELL BANKER REALTY

  • /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
  • /18

    $1,740 Per Month

    • 4 Beds
    • 3 Baths
    • 2,576 Sq Ft
    • House for Rent

    3637 Queens Cove Blvd, Winter Haven, FL 33880

    EXCITING NEWS: WE RECENTLY RENOVATED THIS HOME! IMPROVEMENTS INCLUDE: NEW STAINLESS STEEL APPLIANCES. Apply now or schedule your self-tour today and take the first step toward getting more than just a place to live. Rent with FirstKey Homes for a home that's right for you, plus professional service and maintenance, innovative resident programs, and more; that's the power of

    3637 Queens Cove Blvd, Winter Haven, FL 33880
  • /2

    $269,000

    Sold Sep 30, 2025

    122 Majestic Gardens Ct, Winter Haven, FL 33880

    • 4 Beds
    • 2 Baths
    • 1,688 Sq Ft
    • Built 2012

    Last Sold Summary

    • $159/SF
    • 6 Days On Market

    Current Estimated Value $277,101

    Last Listing Agent Corinna Weaver CROSBY & ASSOCIATES, INC.

    122 Majestic Gardens Ct, Winter Haven, FL 33880
    • /65

      Not Listed For Sale

      4326 Cherrywood St, Winter Haven, FL 33880

      • 2 Beds
      • 2 Baths
      • 1,320 Sq Ft
      • Built 1983
      4326 Cherrywood St, Winter Haven, FL 33880

      Last Sold Summary

      • 14 Days On Market

      Last Listing Agent Kathy Devor COLDWELL BANKER 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
  • /15

    $1,855 Per Month

    • 4 Beds
    • 2 Baths
    • 1,938 Sq Ft
    • House for Rent

    178 Andreas St, Winter Haven, FL 33881

    Apply now or schedule your self-tour today and take the first step toward getting more than just a place to live. Rent with FirstKey Homes for a home that's right for you, plus professional service and maintenance, innovative resident programs, and more; that's the power of purple!This 4-bedroom, 2-bathroom rental home in Winter Haven, FL, has a lot to offer; does it check all your boxes?

    178 Andreas St, Winter Haven, FL 33881
  • /2

    $65,000

    Sold Mar 20, 2026

    200 El Camino Dr Unit 203, Winter Haven, FL 33884

    • 2 Beds
    • 2 Baths
    • 1,378 Sq Ft
    • Built 1971

    Last Sold Summary

    • 34% Below List Price
    • $47/SF
    • 20 Days On Market

    Current Estimated Value $90,355

    Last Listing Agent Christina Ashley DALTON WADE INC

    200 El Camino Dr Unit 203, Winter Haven, FL 33884
    • /2

      Not Listed For Sale

      6792 Brentwood Dr NE, Winter Haven, FL 33881

      • 2 Beds
      • 2 Baths
      • 1,000 Sq Ft
      • Built 1984
      6792 Brentwood Dr NE, Winter Haven, FL 33881

      Last Sold Summary

      • 26 Days On Market

      Last Listing Agent Laura Villardi COLDWELL BANKER REALTY

  • /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
  • /19

    $1,759 Per Month

    • 3 Beds
    • 2 Baths
    • 1,630 Sq Ft
    • House for Rent

    495 Majestic Gardens Blvd, Winter Haven, FL 33880

    This home is professionally managed by Tricon, dedicated to creating exceptional rental experiences. Featuring 3 bedrooms, 2.0 bathrooms, and approximately 1,630 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 rental

    495 Majestic Gardens Blvd, Winter Haven, FL 33880
  • /2

    $275,000

    Sold Aug 06, 2026

    3875 Osprey Pointe Cir, Winter Haven, FL 33884

    • 3 Beds
    • 2 Baths
    • 1,729 Sq Ft
    • Built 2006

    Last Sold Summary

    • 4% Below List Price
    • $159/SF
    • 21 Days On Market

    Current Estimated Value $284,687

    Last Listing Agent Jared Lippelgoos COLDWELL BANKER REALTY

    3875 Osprey Pointe Cir, Winter Haven, FL 33884
    • /2

      Not Listed For Sale

      122 Avenue C NE, Winter Haven, FL 33881

      • 7 Beds
      • 4 Baths
      • 2,352 Sq Ft
      • Built 1927
      122 Avenue C NE, Winter Haven, FL 33881

      Last Sold Summary

      • 74 Days On Market

      Last Listing Agent Steven Koleno BEYCOME OF FLORIDA LLC

  • /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
  • /17

    $850

    Total Monthly Price

    • 1 Bed
    • 1 Bath
    • 500 Sq Ft
    • Condo for Rent

    1131 5th St SW Unit 5 Upstairs, Winter Haven, FL 33880

    Centrally located to restaurants, Aldis, Lowe's and other shopping within walking distance. Small quiet apartments - property has security lights for safety.

    1131 5th St SW Unit 5 Upstairs, Winter Haven, FL 33880
  • /15

    $295,990

    Sold Jun 24, 2026

    6337 Botticella Blvd, Winter Haven, FL 33884

    • 4 Beds
    • 2 Baths
    • 2,370 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • 11% Below List Price
    • $125/SF
    • 36 Days On Market

    Current Estimated Value $294,271

    6337 Botticella Blvd, Winter Haven, FL 33884
    • /2

      Est $394,533

      Not Listed For Sale

      5005 Pebble Beach Blvd, Winter Haven, FL 33884

      • 3 Beds
      • 2 Baths
      • 1,892 Sq Ft
      • Built 2007
      5005 Pebble Beach Blvd, Winter Haven, FL 33884

      Last Sold Summary

      • 40 Days On Market

      Last Listing Agent Emily Muscarella A+ REALTY LLC

  • /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
  • /11

    $1,725

    Total Monthly Price

    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft
    • House for Rent

    711 Avenue B NE, Winter Haven, FL 33881

    This is a 3/2 home in Winter Haven Fl. This home is move in ready and had been freshly updated. Call for your showing today. Close to downtown and convenient to all winter haven has to offer.Washer Dryer hook upsCentral heat and airScreened porchLong term or short term approved.

    711 Avenue B NE, Winter Haven, FL 33881
  • /2

    $365,000

    Sold Oct 17, 2025

    236 Golf Aire Blvd, Winter Haven, FL 33884

    • 3 Beds
    • 2.5 Baths
    • 2,523 Sq Ft
    • Built 2000

    Last Sold Summary

    • 15% Below List Price
    • $145/SF
    • 27 Days On Market

    Current Estimated Value $384,459

    Last Listing Agent Amanda Harrison HARRISON REAL PROPERTY GROUP

    236 Golf Aire Blvd, Winter Haven, FL 33884
    • /65

      Est $515,159

      Not Listed For Sale

      3100 Gerber Dairy Rd, Winter Haven, FL 33880

      • 5 Beds
      • 3 Baths
      • 2,318 Sq Ft
      • Built 2003
      3100 Gerber Dairy Rd, Winter Haven, FL 33880

      Last Sold Summary

      • 345 Days On Market

      Last Listing Agent Barbara Taylor COLDWELL BANKER REALTY

  • /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
  • /2

    $2,500

    Total Monthly Price

    • 4 Beds
    • 2 Baths
    • 8,624 Sq Ft
    • House for Rent

    558 Reddicks Cir, Winter Haven, FL 33884

    This is a single family property located in a quiet neighborhood but not too far from all necessesities and parks. LegoLand is about 10 minutes away, all shopping but not limited to Walmart and Publix is 5 minutes away. We have great schools in our neighborhood and the house has a lot of space. All new kitchen appliance were installed for our new tenants.

    558 Reddicks Cir, Winter Haven, FL 33884
  • /2

    $253,000

    Sold Sep 04, 2026

    1516 Avenue D NE, Winter Haven, FL 33881

    • 3 Beds
    • 2 Baths
    • 1,089 Sq Ft
    • Built 1970

    Last Sold Summary

    • 13% Below List Price
    • $232/SF
    • 236 Days On Market

    Current Estimated Value $247,992

    Last Listing Agent Karina Turcios LPT REALTY, LLC

    1516 Avenue D NE, Winter Haven, FL 33881
    • /20

      Not Listed For Sale

      5887 Fox Haven Dr, Winter Haven, FL 33884

      • 2 Beds
      • 2 Baths
      • 720 Sq Ft
      • Built 1982
      5887 Fox Haven Dr, Winter Haven, FL 33884

      Last Sold Summary

      • 99 Days On Market

      Last Listing Agent Theresa Mace CROSBY & ASSOCIATES, INC.

  • /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
  • /27

    $1,600

    Total Monthly Price

    • 3 Beds
    • 2 Baths
    • 1,411 Sq Ft
    • Condo for Rent

    690 Avenue C SE Unit 690, Winter Haven, FL 33880

    690 Avenue C SE Unit 690, Winter Haven, FL 33880
  • /2

    $160,000

    Sold Feb 20, 2026

    398 Winter Ridge Blvd Unit 398, Winter Haven, FL 33881

    • 2 Beds
    • 2 Baths
    • 1,241 Sq Ft
    • Built 1996

    Last Sold Summary

    • 3% Above List Price
    • $129/SF
    • 106 Days On Market

    Last Listing Agent CarLee Marchetti STAR REALTY OF WINTER HAVEN

    398 Winter Ridge Blvd Unit 398, Winter Haven, FL 33881
    • /2

      Not Listed For Sale

      323 Thornhill Estates Ct, Winter Haven, FL 33880

      • 3 Beds
      • 2 Baths
      • 1,904 Sq Ft
      • Built 1997
      323 Thornhill Estates Ct, Winter Haven, FL 33880

      Last Sold Summary

      • 9 Days On Market

      Last Listing Agent Stephen Willis KELLER WILLIAMS TAMPA CENTRAL

Showing Results 401 - 440, Page 11 of 18

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