49,346

Winter Haven, FL Homes

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  • /37

    $289,000

    $26K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,770 Sq Ft

    1085 Brenton Manor Dr, Winter Haven, FL 33881

    Charming and inviting, this 3-bed, 2-bath home sits in a lovely Winter Haven community with a very low HOA. Built in 2015, it offers a modern design, a comfortable one-level layout, a 2-car garage, and all appliances included. Tucked into the vibrant Chain of Lakes region, you’re surrounded by peaceful views, leafy lakes, and plenty of outdoor fun from boat cruises to paddle boarding. And when

    Agent Photo

    Clarisa Moody

    MARZUCCO REAL ESTATE

    1085 Brenton Manor Dr, Winter Haven, FL 33881
  • /35

    $2,400 Per Month

    • 4 Beds
    • 2 Baths
    • 1,791 Sq Ft
    • House for Rent

    330 Royal Palm Way, Winter Haven, FL 33881

    **THIS ADDRESS WAS FORMALLY KNOWN AS 326 OXFORD DRIVE. STREET NAME WAS CHANGED TO ROYAL PALM WAY. THE NEW ADDRESS WILL NOT PULL UP ON THE MAP**Private community, energy efficient homes, LOADED with the best finishes. With three different elevations to choose from, you will notice a completely different look and feel. If you have pets, not only do we allow them. Home available that

    330 Royal Palm Way, Winter Haven, FL 33881
  • /5

    $244,990

    Sold Aug 29, 2025

    230 Turtle Bay Ave, Winter Haven, FL 33881

    • 3 Beds
    • 2 Baths
    • 1,604 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • $153/SF
    • 11 Days On Market

    Highland Homes Harbor at Lake Henry - Townhomes

    230 Turtle Bay Ave, Winter Haven, FL 33881
    • /2

      Est $373,593

      Not Listed For Sale

      4264 Stafford Dr, Winter Haven, FL 33880

      • 3 Beds
      • 3 Baths
      • 2,778 Sq Ft
      • Built 1983
      4264 Stafford Dr, Winter Haven, FL 33880

      Last Sold Summary

      • 218 Days On Market

  • /40

    $365,000

    • 3 Beds
    • 3 Baths
    • 2,042 Sq Ft

    340 Vail Dr, Winter Haven, FL 33884

    Beautifully updated home tucked away on a quiet cul-de-sac in the well-established Cedar Cove community, just moments from the scenic shores of Lake Eloise. Set on over a quarter-acre lot, this property offers more than 2,000 sq ft of thoughtfully designed living space, featuring 3 bedrooms, 3 full bathrooms, and an enclosed bonus room that can easily function as a 4th bedroom. Inside, bright

    Agent Photo

    Carlos DeJesus

    EXIT REALTY 4CORNERS

    340 Vail Dr, Winter Haven, FL 33884
  • /14

    Starting at $1,000 Per Month

    • Studio - 2 Beds

    130 Avenue C SE, Winter Haven, FL 33880

    Central Haven Apartments

    130 Avenue C SE, Winter Haven, FL 33880
  • /2

    $369,999

    Sold Oct 20, 2025

    5465 San Pietro Dr, Winter Haven, FL 33884

    • 4 Beds
    • 3 Baths
    • 2,292 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • $161/SF
    • 10 Days On Market

    Current Estimated Value $352,902

    Casa Fresca Homes Villa Mar

    5465 San Pietro Dr, Winter Haven, FL 33884
    • /2

      Est $520,675

      Not Listed For Sale

      1396 Lucerne Loop Rd NE, Winter Haven, FL 33881

      • 4 Beds
      • 3 Baths
      • 2,371 Sq Ft
      • Built 2005
      1396 Lucerne Loop Rd NE, Winter Haven, FL 33881

      Last Sold Summary

      • 408 Days On Market

  • /45

    $451,000

    $14K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,663 Sq Ft

    148 Lake Otis Rd, Winter Haven, FL 33884

    SELLER VERY MOTIVATED! Spacious 4-Bedroom, 3-Bath Pool Home in the admired Lakewood Community. Nestled on an oversized lot with mature trees, this remodeled tri-level home offers a perfect blend of modern luxury and comfort. With a spacious layout, a private pool, and an abundance of natural light, this home is designed for both relaxation and entertaining. As you enter, you’ll immediately notice

    Agent Photo

    Michelle Armbruster

    LOCKHART & ASSOCIATES INC

    148 Lake Otis Rd, Winter Haven, FL 33884
  • /31

    $1,800

    Total Monthly Price

    • 4 Beds
    • 2 Baths
    • 1,368 Sq Ft
    • House for Rent

    3960 Avenue U NW, Winter Haven, FL 33881

    Don't miss out on this 4 bedroom home, at an amazing price. This home has been freshly painted and has ceramic tile throughout. The French doors lead to a paver patio that provides access to a huge backyard. The uncovered gazebo/patio area is perfect for those fire pit evenings. Your front covered patio gives you a Waterview of Lake Blue.

    3960 Avenue U NW, Winter Haven, FL 33881
  • /2

    $335,000

    Sold Jul 24, 2026

    3600 Julius Estates Blvd, Winter Haven, FL 33881

    • 4 Beds
    • 2.5 Baths
    • 2,526 Sq Ft
    • Built 2014

    Last Sold Summary

    • 4% Below List Price
    • $133/SF
    • 299 Days On Market

    Current Estimated Value $338,683

    Last Listing Agent Gladys Falcon LUXURY REAL ESTATE GROUP LLC

    3600 Julius Estates Blvd, Winter Haven, FL 33881
    • /2

      Est $234,888

      Not Listed For Sale

      4428 Glenns Landing, Winter Haven, FL 33884

      • 2 Beds
      • 2 Baths
      • 1,359 Sq Ft
      • Built 1990
      4428 Glenns Landing, Winter Haven, FL 33884

      Last Sold Summary

      • 58 Days On Market

  • /42

    $254,900

    $15K PRICE DROP Under Contract
    • 3 Beds
    • 2 Baths
    • 1,706 Sq Ft

    4622 Cypress Gardens Rd, Winter Haven, FL 33884

    Under contract-accepting backup offers. Move-In Ready with Major Updates! Welcome home to this beautifully refreshed 3-bedroom, 2-bath, 2-car garage residence offering over 1,700 square feet of comfortable living space in the heart of Winter Haven. Featuring a NEW ROOF, a NEW HVAC SYSTEM, and stylish interior finishes throughout, this home is ready for its next owner to move right in! Inside,

    Agent Photo

    Sam Daniels

    KELLER WILLIAMS REALTY SMART 1

    4622 Cypress Gardens Rd, Winter Haven, FL 33884
  • /35

    $2,425 Per Month

    • 4 Beds
    • 2 Baths
    • 1,791 Sq Ft
    • House for Rent

    326 Royal Palm Way, Winter Haven, FL 33881

    **THIS ADDRESS WAS FORMALLY KNOWN AS 326 OXFORD DRIVE. STREET NAME WAS CHANGED TO ROYAL PALM WAY. THE NEW ADDRESS WILL NOT PULL UP ON THE MAP** Private community, energy efficient homes, LOADED with the best finishes. With three different elevations to choose from, you will notice a completely different look and feel. If you have pets, not only do we allow them. Home available that

    326 Royal Palm Way, Winter Haven, FL 33881
  • /2

    $124,500

    Sold Apr 08, 2026

    4204 Cedarwood Dr, Winter Haven, FL 33880

    • 2 Beds
    • 2 Baths
    • 1,496 Sq Ft
    • Built 1983

    Last Sold Summary

    • 3% Below List Price
    • $83/SF
    • 9 Days On Market

    Last Listing Agent Kathy Devor COLDWELL BANKER REALTY

    4204 Cedarwood Dr, Winter Haven, FL 33880
    • /2

      Est $243,384

      Not Listed For Sale

      2005 9th Ct NE, Winter Haven, FL 33881

      • 4 Beds
      • 2 Baths
      • 1,392 Sq Ft
      • Built 1970
      2005 9th Ct NE, Winter Haven, FL 33881

      Last Sold Summary

      • 66 Days On Market

  • /39

    $54,990

    • 2 Beds
    • 2 Baths

    75 Bern Dr, Winter Haven, FL 33881

    **Your Central Florida retreat awaits.** This 2-bedroom, 2-bathroom manufactured home in Swiss Village - a 55+ active adult community - delivers comfort, convenience, and a lifestyle most only dream about. Inside, you'll find a freshly painted interior that feels bright and inviting from the moment you walk through the door. A powerful 3-ton A/C unit installed in 2023 keeps every room cool during

    Agent Photo

    Chrissy Walter

    Sunset Home Sales

    75 Bern Dr, Winter Haven, FL 33881
  • /16

    $1,849 Per Month

    • 4 Beds
    • 2 Baths
    • 2,138 Sq Ft
    • House for Rent

    608 Terranova Dr, Winter Haven, FL 33884

    Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $1993.90. That covers your base rent, $1849.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    608 Terranova Dr, Winter Haven, FL 33884
  • /2

    $352,690

    Sold Sep 10, 2025

    2803 San Marco Way, Winter Haven, FL 33884

    • 3 Beds
    • 2.5 Baths
    • 2,298 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • $153/SF

    Current Estimated Value $352,141

    Maronda Homes Villamar

    2803 San Marco Way, Winter Haven, FL 33884
    • /2

      Est $307,697

      Not Listed For Sale

      59 Jimmy Lee Rd, Winter Haven, FL 33880

      • 3 Beds
      • 2 Baths
      • 2,244 Sq Ft
      • Built 1974
      59 Jimmy Lee Rd, Winter Haven, FL 33880

      Last Sold Summary

      • 4 Days On Market

  • /36

    $269,000

    $16K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,122 Sq Ft

    820 26th St NW, Winter Haven, FL 33881

    Welcome to 820 NW 26th St, Winter Haven, Florida—a move-in ready 3-bedroom, 2-bath home featuring updates inside and out. This property has been thoughtfully refreshed with a focus on comfort, style, and modern living.Enjoy a beautifully updated interior along with exterior improvements that enhance the home’s appeal. The kitchen comes equipped with all-new appliances, making everyday living

    Agent Photo

    Sonya Duke

    241 REAL ESTATE LLC

    820 26th St NW, Winter Haven, FL 33881
  • /20

    Starting at $3,250 Per Month

    • 2 Beds

    154 2nd St SW, Winter Haven, FL 33880

    Raingarden Apartments is a 9-unit collection of spacious luxury townhouse apartments located in downtown Winter Haven. Perfect for those looking to embrace a walkable, urban lifestyle where environmentally conscious living meets uncompromising, modern sophistication. All units have an enclosed 2-car garage and courtyard patio.

    Raingarden Apartments

    154 2nd St SW, Winter Haven, FL 33880
  • /2

    $144,500

    Sold Jan 23, 2026

    1550 11th St NE Unit B6, Winter Haven, FL 33881

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

    Last Sold Summary

    • 4% Below List Price
    • $126/SF
    • 7 Days On Market

    Current Estimated Value $139,301

    Last Listing Agent Laura Barnes CHAIN OF LAKES REALTY INC

    1550 11th St NE Unit B6, Winter Haven, FL 33881
    • /2

      Est $288,097

      Not Listed For Sale

      1491 Avenue F NE, Winter Haven, FL 33881

      • 3 Beds
      • 2 Baths
      • 1,824 Sq Ft
      • Built 1962
      1491 Avenue F NE, Winter Haven, FL 33881

      Last Sold Summary

      • 3 Days On Market

  • /16

    $113,000

    $7K PRICE DROP
    • 2 Beds
    • 1.5 Baths
    • 851 Sq Ft

    831 Orchid Springs Dr Unit 831, Winter Haven, FL 33884

    Whether you are looking for your first home or first rental property, this condominium is a must see! Ideally located off of Overlook Drive in Winter Haven, minutes form Legoland, downtown Winter Haven, and the Chain of Lakes. This unit features an updated kitchen with an upgraded stainless steel gas stove, stainless steel dish washer, and a one-year-old refrigerator. Additionally, there are

    Agent Photo

    Steven Perkins

    CLARK REALTY LLC

    831 Orchid Springs Dr Unit 831, Winter Haven, FL 33884
  • /9

    Starting at $975 Per Month

    • 1 Bed

    101-123 Oak Crest Dr NW, Winter Haven, FL 33881

    Ideally located with convenient access to US Hwy 17-92, I-4, and the greater Winter Haven and Central Florida area, this community offers both accessibility and comfort.Our cozy one-bedroom apartments feature energy-efficient central A/C, tile flooring, washer/dryer hookups, and newly updated appliances designed for everyday convenience.Residents enjoy scenic surroundings,

    Oakcrest Apartments

    101-123 Oak Crest Dr NW, Winter Haven, FL 33881
  • /2

    $285,000

    Sold May 04, 2026

    141 Browning Cir, Winter Haven, FL 33884

    • 2 Beds
    • 2 Baths
    • 1,629 Sq Ft
    • Built 1969

    Last Sold Summary

    • 4% Below List Price
    • $175/SF
    • 22 Days On Market

    Current Estimated Value $286,396

    Last Listing Agent Mike Nolen COLDWELL BANKER REALTY

    141 Browning Cir, Winter Haven, FL 33884
    • /2

      Est $252,125

      Not Listed For Sale

      362 Lake Daisy Cir, Winter Haven, FL 33884

      • 3 Beds
      • 2 Baths
      • 1,239 Sq Ft
      • Built 2005
      362 Lake Daisy Cir, Winter Haven, FL 33884

      Last Sold Summary

      • 47 Days On Market

  • /33

    $220,900

    $29K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,410 Sq Ft

    936 Avenue T SE, Winter Haven, FL 33880

    Short Sale. **SHORT SALE** BANK APPROVED PRICE** CAN CLOSE QUICKLY*** Welcome to this beautiful 3-bedroom, 2-bathroom block home perfectly positioned at the end of a quiet cul-de-sac in Winter Haven's sought-after Cypress Gardens neighborhood. With 1,400 square feet of interior living space and a layout designed for both comfort and connection, this home checks every box. Step inside and you're

    Agent Photo

    Daniel Rodriguez

    NEW HEIGHTS REALTY GROUP

    936 Avenue T SE, Winter Haven, FL 33880
  • /18

    Starting at $999 Per Month

    • 1 - 2 Beds

    102 Landings Way, Winter Haven, FL 33880

    Welcome to The Landings, a tranquil pet friendly retreat nestled among towering trees and lush greenery in the heart of Winter Haven, Florida. As one of our three Winter Haven locations, The Landings offers upgraded 1 and 2 bedroom apartments designed with spacious layouts that maximize comfort and livability. Each home features modern white cabinets that brighten the space, durable vinyl

    The Landings Apartment Homes

    102 Landings Way, Winter Haven, FL 33880
  • /2

    $319,990

    Sold May 13, 2026

    4125 Giorgio Dr, Winter Haven, FL 33884

    • 4 Beds
    • 2.5 Baths
    • 2,305 Sq Ft
    • Built 2026

    Last Sold Summary

    • $139/SF

    Current Estimated Value $301,568

    Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

    4125 Giorgio Dr, Winter Haven, FL 33884
    • /2

      Est $322,367

      Not Listed For Sale

      622 Avenue D SE, Winter Haven, FL 33880

      • 4 Beds
      • 3 Baths
      • 2,976 Sq Ft
      • Built 1957
      622 Avenue D SE, Winter Haven, FL 33880

      Last Sold Summary

      • 9 Days On Market

  • /32

    $250,000

    $25K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 1,957 Sq Ft

    1533 Majestic Ln, Winter Haven, FL 33880

    Short Sale. We are in the process of getting a short sale approved. So expect delays. Welcome to the community of Eagle Landing in beautiful SE Winter Haven, Florida. This newer home features 4 Bedrooms/2.5 Bathrooms with a spacious two-story layout that maximizes space and natural light perfect for any lifestyle with Low HOA and NO CDD. The modern kitchen design with Island and Breakfast Bar

    Agent Photo

    Cheryl Brewer

    COLDWELL BANKER REALTY

    1533 Majestic Ln, Winter Haven, FL 33880
  • /20

    Starting at $950 Per Month

    • 1 Bed

    745 Avenue A SW, Winter Haven, FL 33880

    Lakeview Tower offers newly remodeled studio and one bedroom apartment homes. It is an exceptional senior living, 62+ and disabled Community. Lakeview Tower sits right on Lake Howard, allowing breath taking views from your window.

    Lakeview Tower

    745 Avenue A SW, Winter Haven, FL 33880
  • /2

    $168,500

    Sold May 18, 2026

    5892 Fox Haven Dr, Winter Haven, FL 33884

    • 3 Beds
    • 2 Baths
    • 1,440 Sq Ft
    • Built 1991

    Last Sold Summary

    • $117/SF
    • 2 Days On Market

    Last Listing Agent Susan Rohlfing QUINN & COMPANY REALTORS, LLC

    5892 Fox Haven Dr, Winter Haven, FL 33884
    • /2

      Est $321,060

      Not Listed For Sale

      41 Lake Link Cir SE, Winter Haven, FL 33884

      • 3 Beds
      • 2 Baths
      • 1,704 Sq Ft
      • Built 2004
      41 Lake Link Cir SE, Winter Haven, FL 33884

      Last Sold Summary

      • 64 Days On Market

  • /56

    $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,

    Agent Photo

    Chrissy Walter

    Sunset Home Sales

    293 Alpine Dr, Winter Haven, FL 33881
  • /15

    $2,390 Per Month

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

    3637 Queens Cove Blvd, Winter Haven, FL 33880

    EXCITING NEWS: WE ARE CURRENTLY RENOVATING THIS HOME! NOTE THAT THE PHOTOS SHOWN REPRESENT THE HOME BEFORE RENOVATION AND DO NOT REFLECT ANY UPDATES. PLANNED IMPROVEMENTS INCLUDE: NEW STAINLESS-STEEL APPLIANCES. 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

    3637 Queens Cove Blvd, Winter Haven, FL 33880
  • /16

    $316,990

    Sold Sep 04, 2025

    3466 Evening Star Dr, Winter Haven, FL 33881

    • 3 Beds
    • 2 Baths
    • 1,536 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • $206/SF
    • 26 Days On Market

    Current Estimated Value $327,325

    Starlight Homes Sunset Hills

    3466 Evening Star Dr, Winter Haven, FL 33881
    • /2

      Est $297,497

      Not Listed For Sale

      76 Saint Kitts Cir, Winter Haven, FL 33884

      • 3 Beds
      • 2 Baths
      • 1,508 Sq Ft
      • Built 1993
      76 Saint Kitts Cir, Winter Haven, FL 33884

      Last Sold Summary

      • 3 Days On Market

Showing Results 121 - 160, Page 4 of 18

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