49,151

Winter Haven, FL Homes

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  • /32

    $379,900

    • 5 Beds
    • 3 Baths
    • 2,696 Sq Ft

    204 Inman Blvd, Winter Haven, FL 33881

    Welcome home to this beautifully maintained 5-bedroom, 3-bath residence offering nearly 2,700 square feet of flexible living space in one of Winter Haven's fastest-growing areas. Priced at just $379,900, this spacious home delivers exceptional value with room for everyone.Designed with today's lifestyles in mind, the thoughtfully crafted floor plan includes five true bedrooms, three full

    Agent Photo

    Veronica Bard

    LA ROSA REALTY PRESTIGE

    204 Inman Blvd, Winter Haven, FL 33881
  • /35

    Starting at $1,258 Per Month

    • 1 - 3 Beds

    2850 W Lake Hamilton Dr, Winter Haven, FL 33881

    Brand-New Apartment Homes, Newly Repriced.1 Bed - As low as $11992 Bed - As low as $14993 Bed - As low as $1650PLUS 1 month FREE on 19-24 month lease terms. Schedule your tour TODAY!

    Magnolia at Lake Hamilton

    2850 W Lake Hamilton Dr, 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 $286,846

    Last Listing Agent Mike Nolen COLDWELL BANKER REALTY

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

      Est $309,916

      Not Listed For Sale

      257 Oleander St, Winter Haven, FL 33881

      • 4 Beds
      • 2.5 Baths
      • 2,195 Sq Ft
      • Built 2018
      257 Oleander St, Winter Haven, FL 33881

      Last Sold Summary

      • 78 Days On Market

      Last Listing Agent Vilmari Caraballo RE/MAX ASSURED

  • /38

    $49,990

    $5K PRICE DROP
    • 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
  • /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

    $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 $321,682

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

    4125 Giorgio Dr, Winter Haven, FL 33884
    • /16

      Not Listed For Sale

      6482 Peppertree Path NE, Winter Haven, FL 33881

      • 2 Beds
      • 2 Baths
      • 1,300 Sq Ft
      • Built 1986
      6482 Peppertree Path NE, Winter Haven, FL 33881

      Last Sold Summary

      • 52 Days On Market

      Last Listing Agent Jean Murphy CENTURY 21 MYERS REALTY

  • /43

    $164,800

    • 2 Beds
    • 2 Baths
    • 1,325 Sq Ft

    628 Lakeside Ranch Ln, Winter Haven, FL 33881

    Meticulously Maintained, beautiful 2/2, move-in ready home in a quiet lake-front community. Pride of Ownership shows throughout! List of Updates attached and include finished walls, Plumbing, downspouts, Heat Pump with UV Light, Newer Appliance, Washer and Dryer (inside laundry), flooring, kitchen cabinets with soft-close, built-in pantry/storage in the Dining Room to name a few. Thoughtfully

    Agent Photo

    Sanda Andrews

    GOOD COMPANY REALTY INC.

    628 Lakeside Ranch Ln, Winter Haven, FL 33881
  • /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
    • /34

      Est $111,076

      Not Listed For Sale

      2040 San Marcos Dr SE Unit 108, Winter Haven, FL 33880

      • 1 Bed
      • 1 Bath
      • 666 Sq Ft
      • Built 1985
      2040 San Marcos Dr SE Unit 108, Winter Haven, FL 33880

      Last Sold Summary

      • 28 Days On Market

      Last Listing Agent Spyro Lefkimiotis RE/MAX ACTION FIRST OF FLORIDA

  • /36

    $249,000

    $36K 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

    $210,000

    Sold May 20, 2026

    144 Brad Cir, Winter Haven, FL 33880

    • 3 Beds
    • 2 Baths
    • 1,317 Sq Ft
    • Built 1996

    Last Sold Summary

    • 14% Below List Price
    • $159/SF
    • 103 Days On Market

    Current Estimated Value $222,107

    Last Listing Agent Chrissi Jasso ASSOCIATE REALTY

    144 Brad Cir, Winter Haven, FL 33880
    • /12

      Not Listed For Sale

      713 Byni Ridge, Winter Haven, FL 33880

      • 3 Beds
      • 2 Baths
      • 924 Sq Ft
      • Built 1990
      713 Byni Ridge, Winter Haven, FL 33880

      Last Sold Summary

      • 14 Days On Market

      Last Listing Agent Ron Denney LAND SOUTH REALTY, LLC

  • /28

    $355,000

    $24K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,054 Sq Ft

    41 Greenfield Ct, Winter Haven, FL 33884

    Premier Location overlooking the pond and the golf course.This traditional 3 bedroom 2 bath estate home offers split bedrooms, formal living and dining areas, large family room, master suite with dual vanities and dual closets, oversized garage with a shower and a screen enclosed pool.From the pool deck, enjoy watching the varied species of birds that pass by or land for a stroll/swim in

    Agent Photo

    Steven Smith, PA

    LOCKHART & ASSOCIATES INC

    41 Greenfield Ct, Winter Haven, FL 33884
  • /15

    $1,895 Per Month

    • 3 Beds
    • 2 Baths
    • 1,720 Sq Ft
    • House for Rent

    188 Black Skimmer Ln, Wahneta, FL 33880

    This modern 3-bedroom, 2-bath home offers 1,720 square feet of comfortable living in Wahneta’s serene suburban setting. Thoughtfully maintained, it features a fresh, neutral palette and clean finishes that complement wood-look laminate flooring throughout the main areas. Ceiling fans with integrated lighting enhance the open living space’s inviting ambiance. The bedrooms balance carpet and

    188 Black Skimmer Ln, Wahneta, FL 33880
  • /39

    $389,557

    Sold Nov 14, 2025

    276 Meredith Blvd, Winter Haven, FL 33881

    • 4 Beds
    • 3 Baths
    • 2,110 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • $185/SF
    • 20 Days On Market

    Dream Finders Homes Willowbrook North

    276 Meredith Blvd, Winter Haven, FL 33881
    • /28

      Est $127,607

      Not Listed For Sale

      689 Lake Howard Dr NW Unit 103, Winter Haven, FL 33880

      • 3 Beds
      • 2 Baths
      • 1,232 Sq Ft
      • Built 1975
      689 Lake Howard Dr NW Unit 103, Winter Haven, FL 33880

      Last Sold Summary

      • 23 Days On Market

      Last Listing Agent Catherine Kluytenaar THE K TEAM REAL ESTATE SERVICES LLC

  • /31

    $219,900

    Open Thu 4PM - 6PM $60K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,368 Sq Ft

    14 Enclave Dr, Winter Haven, FL 33884

    This meticulously maintained and professionally updated 2 bedroom 2 bath villa is located in the sought after "Enclave" neighborhood in Cypresswood, a gated golf community in SE Winter Haven.The open floor plan features an expansive kitchen with breakfast nook, spacious living/dining room combo, split bedrooms with ample closets, inside laundry area equipped with a washer and dryer, screened

    Agent Photo

    Steven Smith, PA

    LOCKHART & ASSOCIATES INC

    14 Enclave Dr, Winter Haven, FL 33884
  • /20

    $1,995 Per Month

    • 3 Beds
    • 2 Baths
    • 1,841 Sq Ft
    • House for Rent

    914 Summer Glen Dr, Winter Haven, FL 33880

    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 $2179.90. That covers your base rent, $1995.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    914 Summer Glen Dr, Winter Haven, FL 33880
  • /16

    $242,490

    Sold May 28, 2026

    3060 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

    3060 Captain Jax Way, Winter Haven, FL 33884
    • /2

      Est $296,662

      Not Listed For Sale

      5069 Brenton Manor Ave, Winter Haven, FL 33881

      • 3 Beds
      • 2 Baths
      • 1,895 Sq Ft
      • Built 2013
      5069 Brenton Manor Ave, Winter Haven, FL 33881

      Last Sold Summary

      • 154 Days On Market

      Last Listing Agent Christine Hubbert BHHS FLORIDA PROPERTIES GROUP

  • /16

    $112,000

    $8K 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
  • /4

    $2,150 Per Month

    • 4 Beds
    • 2 Baths
    • 2,014 Sq Ft
    • House for Rent

    737 Lake Martha Dr NE, Winter Haven, FL 33881

    Property Id: 945068 Large Lake House 4 bedroom 2 bath home at waters edge has a lot of charm. There is a laundry room off the large kitchen. A large screened porch faces the lake. Spend the day relaxing under the large porch with two fans. Barbecue on and enjoy lakefront as if you are on vacation. You might spot a bald eagle flying above while fishing on the lake. •

    737 Lake Martha Dr NE, Winter Haven, FL 33881
  • /30

    $259,990

    Sold Jun 02, 2026

    4102 Penelope Ave, Winter Haven, FL 33859

    • 3 Beds
    • 2 Baths
    • 1,407 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • $185/SF
    • 30 Days On Market

    Dream Finders Homes Annabelle Estates

    4102 Penelope Ave, Winter Haven, FL 33859
    • /2

      Est $307,224

      Not Listed For Sale

      118 Lake Sears Dr, Winter Haven, FL 33880

      • 2 Beds
      • 3 Baths
      • 1,422 Sq Ft
      • Built 1957
      118 Lake Sears Dr, Winter Haven, FL 33880

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Melissa Connell PALM & PINE REALTY GROUP LLC

  • /32

    $235,000

    $40K 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
  • /11

    $1,250 Per Month

    • 2 Beds
    • 1 Bath
    • 500 Sq Ft
    • Condo for Rent

    708 Vittorio Dr, Winter Haven, FL 33884

    Welcome to your new home in Winter Haven, Florida! Beautifully furnished and move-in ready 2-bedroom, 1-bathroom apartment offering comfortable and convenient living in Winter Haven. This cozy unit features a private entrance, comfortable living room, and kitchenette, making it an ideal option for those seeking a hassle-free rental. The apartment is fully furnished and includes all utilities in

    708 Vittorio Dr, Winter Haven, FL 33884
  • /2

    $255,990

    Sold Jan 27, 2026

    2134 Chris Dr, Winter Haven, FL 33884

    • 5 Beds
    • 2.5 Baths
    • 2,112 Sq Ft
    • Built 2025

    Last Sold Summary

    • 18% Below List Price
    • $121/SF
    • 49 Days On Market

    Current Estimated Value $270,761

    Last Listing Agent Ben Goldstein LENNAR REALTY

    2134 Chris Dr, Winter Haven, FL 33884
    • /2

      Est $311,244

      Not Listed For Sale

      3810 Fieldstone Cir, Winter Haven, FL 33881

      • 3 Beds
      • 2 Baths
      • 2,000 Sq Ft
      • Built 2016
      3810 Fieldstone Cir, Winter Haven, FL 33881

      Last Sold Summary

      • 206 Days On Market

      Last Listing Agent ALLISON JOHNSTON THE SIMON SIMAAN GROUP

  • /21

    $81,500

    • 2 Beds
    • 2 Baths
    • 1,248 Sq Ft

    215 Fairway Cir, Winter Haven, FL 33881

    Welcome to this beautifully updated 2-bedroom, 2-bath home in the desirable 55+ Swiss Golf & Tennis community of Winter Haven. Offering approximately 1,248 square feet of living space plus an additional 185-sf Florida Room, this home provides plenty of room to relax, entertain, and enjoy the Florida lifestyle. The home has been thoughtfully renovated within the past four years and features a

    Agent Photo

    Cindy Minnick

    Sun Resales, Inc.

    215 Fairway Cir, Winter Haven, FL 33881
  • /16

    $2,049 Per Month

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

    313 Kensington View Dr, Winter Haven, FL 33880

    Welcome to 313 Kensington View Drive, located in the desirable Kensington View community and offering 4 bedrooms, 2 bathrooms, and 1,851 square feet of living space. Inside, you will find a kitchen equipped with stainless steel appliances, and dedicated washer and dryer hookups included for added convenience. The primary bedroom features an attached bathroom with dual sinks. The home also

    313 Kensington View Dr, Winter Haven, FL 33880
  • /2

    $313,162

    Sold Oct 19, 2025

    1558 Jessica Blvd, Winter Haven, FL 33884

    • 5 Beds
    • 2.5 Baths
    • 2,326 Sq Ft
    • Built 2025

    Last Sold Summary

    • 6% Below List Price
    • $135/SF
    • 28 Days On Market

    Current Estimated Value $311,894

    Last Listing Agent Ben Goldstein LENNAR REALTY

    1558 Jessica Blvd, Winter Haven, FL 33884
    • /2

      Not Listed For Sale

      225 Sweet Cir, Winter Haven, FL 33884

      • 2 Beds
      • 2 Baths
      • 1,144 Sq Ft
      • Built 1986
      225 Sweet Cir, Winter Haven, FL 33884

      Last Sold Summary

      • 64 Days On Market

      Last Listing Agent Hank Petty KELLER WILLIAMS REALTY SMART 1

  • /71

    $469,000

    $20K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,153 Sq Ft

    315 Lanceolate Dr, Winter Haven, FL 33880

    Homes in The Village at Spirit Lake don’t come up for sale very often, and this one has a lot to offer.315 Lanceolate Drive is a 3-bedroom, 2-bath pool home with two additional air-conditioned rooms in the converted garage, giving you plenty of flexibility for additional bedrooms, home offices, a gym, playroom, or extra storage.Inside, the home has been thoughtfully updated with a

    Agent Photo

    Veronica Bard

    LA ROSA REALTY PRESTIGE

    315 Lanceolate Dr, Winter Haven, FL 33880
  • /15

    $1,990 Per Month

    • 3 Beds
    • 2 Baths
    • 1,645 Sq Ft
    • House for Rent

    505 Reddicks Cir, Winter Haven, FL 33884

    Please note, our homes are available on a first-come, first-serve basis and are not reserved until the holding fee agreement is signed and the holding fee is paid by the primary applicant. This home is priced to rent and won't be around for long. Apply now, while we make this home ready for you, or call to arrange a meeting with your local Progress Residential leasing specialist today.

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

    $285,000

    Sold Mar 16, 2026

    5316 Hogan Ln, Winter Haven, FL 33884

    • 2 Beds
    • 2 Baths
    • 1,339 Sq Ft
    • Built 2013

    Last Sold Summary

    • 1% Below List Price
    • $213/SF
    • 13 Days On Market

    Current Estimated Value $284,149

    Last Listing Agent Lori Raath LAKE ASHTON REALTY INC.

    5316 Hogan Ln, Winter Haven, FL 33884
    • /42

      Not Listed For Sale

      5947 Silver Fox Dr, Winter Haven, FL 33884

      • 3 Beds
      • 2 Baths
      • 1,620 Sq Ft
      • Built 1981
      5947 Silver Fox Dr, Winter Haven, FL 33884

      Last Sold Summary

      • 41 Days On Market

      Last Listing Agent Dawn Flagg KLINE REAL ESTATE SERVICES

Showing Results 161 - 200, Page 5 of 18

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