49,155

Winter Haven, FL Homes

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  • /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

    $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
  • /22

    $289,000

    Sold Apr 17, 2026

    820 Sun Ridge Village Dr, Winter Haven, FL 33880

    • 4 Beds
    • 2 Baths
    • 2,280 Sq Ft
    • Built 2006

    Last Sold Summary

    • 22% Below List Price
    • $127/SF
    • 215 Days On Market

    Current Estimated Value $292,111

    Last Listing Agent Renee Evans CENTURY 21 MYERS REALTY

    820 Sun Ridge Village Dr, Winter Haven, FL 33880
    • /2

      Est $291,501

      Not Listed For Sale

      1512 Grey Eagle Ln, Winter Haven, FL 33881

      • 4 Beds
      • 2 Baths
      • 1,820 Sq Ft
      • Built 2018
      1512 Grey Eagle Ln, Winter Haven, FL 33881

      Last Sold Summary

      • 45 Days On Market

      Last Listing Agent Vivian Ortiz OAK AVENUE REAL ESTATE 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
  • /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
  • /2

    $355,000

    Sold Apr 17, 2026

    1929 Gerber Dairy Rd, Winter Haven, FL 33880

    • 3 Beds
    • 2 Baths
    • 1,513 Sq Ft
    • Built 2023

    Last Sold Summary

    • 1% Below List Price
    • $235/SF
    • 92 Days On Market

    Current Estimated Value $355,983

    Last Listing Agent Marissa Hipp COLDWELL BANKER REALTY

    1929 Gerber Dairy Rd, Winter Haven, FL 33880
    • /2

      Est $267,661

      Not Listed For Sale

      2168 Bretton Ridge Loop, Winter Haven, FL 33884

      • 4 Beds
      • 2 Baths
      • 1,540 Sq Ft
      • Built 2017
      2168 Bretton Ridge Loop, Winter Haven, FL 33884

      Last Sold Summary

      • 96 Days On Market

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

  • /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
  • /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
  • /17

    $305,900

    Sold Jul 07, 2026

    2527 Sage Valley Way, Winter Haven, FL 33884

    • 3 Beds
    • 2 Baths
    • 1,672 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • 5% Below List Price
    • $183/SF
    • 19 Days On Market

    Current Estimated Value $314,333

    D.R. Horton Harmony at Lake Eloise

    2527 Sage Valley Way, Winter Haven, FL 33884
    • /16

      Est $278,917

      Not Listed For Sale

      4174 Roberta Dr, Winter Haven, FL 33881

      • 3 Beds
      • 2 Baths
      • 1,721 Sq Ft
      • Built 2017
      4174 Roberta Dr, Winter Haven, FL 33881

      Last Sold Summary

      • 138 Days On Market

      Last Listing Agent Vivian Ortiz OAK AVENUE REAL ESTATE LLC

  • /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
  • /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

    $264,000

    Sold Aug 05, 2026

    1034 Summer Glen Dr, Winter Haven, FL 33880

    • 3 Beds
    • 2 Baths
    • 1,847 Sq Ft
    • Built 2006

    Last Sold Summary

    • 5% Below List Price
    • $143/SF
    • 89 Days On Market

    Current Estimated Value $268,437

    Last Listing Agent Jeff Jones MARK SPAIN REAL ESTATE

    1034 Summer Glen Dr, Winter Haven, FL 33880
    • /2

      Est $222,473

      Not Listed For Sale

      2327 Whispering Trails Place, Winter Haven, FL 33884

      • 3 Beds
      • 2 Baths
      • 1,148 Sq Ft
      • Built 2006
      2327 Whispering Trails Place, Winter Haven, FL 33884

      Last Sold Summary

      • 21 Days On Market

      Last Listing Agent Jeff Inman FHG REALTY, 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
  • /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

    $290,000

    Sold Mar 19, 2026

    2005 Spirit Lake Rd, Winter Haven, FL 33880

    • 3 Beds
    • 2 Baths
    • 1,710 Sq Ft
    • Built 1987

    Last Sold Summary

    • 6% Below List Price
    • $170/SF
    • 25 Days On Market

    Current Estimated Value $297,440

    Last Listing Agent Becky Sigler VINTAGE REAL ESTATE SERVICES

    2005 Spirit Lake Rd, Winter Haven, FL 33880
    • /2

      Est $335,422

      Not Listed For Sale

      3484 Julius Estates Blvd, Winter Haven, FL 33881

      • 4 Beds
      • 2.5 Baths
      • 2,900 Sq Ft
      • Built 2013
      3484 Julius Estates Blvd, Winter Haven, FL 33881

      Last Sold Summary

      • 154 Days On Market

      Last Listing Agent Veronica Bard LA ROSA REALTY PRESTIGE

  • /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
  • /21

    $1,965

    Total Monthly Price

    • 4 Beds
    • 2 Baths
    • 1,981 Sq Ft
    • House for Rent

    4766 Osprey Way, Winter Haven, FL 33881

    Now offering 18-month leases. Sign today and lock in today’s low rate for the next 18 months! Offer valid for new applicants who sign an 18-month lease and move-in by September 18, 2026. Base rent will remain at the 12-month lease rate for the duration of the 18-month term. Offer is contingent on application approval and execution of a lease agreement. Other terms and conditions may apply. This

    4766 Osprey Way, Winter Haven, FL 33881
  • /16

    $294,490

    Sold Jul 22, 2026

    6245 Botticella Blvd, Winter Haven, FL 33884

    • 5 Beds
    • 2 Baths
    • 2,112 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • $139/SF
    • 4 Days On Market

    Lennar Villa Mar

    6245 Botticella Blvd, Winter Haven, FL 33884
    • /30

      Est $233,058

      Not Listed For Sale

      1621 Vienna Square Dr, Winter Haven, FL 33884

      • 2 Beds
      • 2 Baths
      • 1,497 Sq Ft
      • Built 2015
      1621 Vienna Square Dr, Winter Haven, FL 33884

      Last Sold Summary

      • 61 Days On Market

      Last Listing Agent Wanda Dicks COLDWELL BANKER REALTY

  • /36

    $165,000

    $35K PRICE DROP Under Contract
    • 3 Beds
    • 2 Baths
    • 1,306 Sq Ft

    124 Center St, Winter Haven, FL 33880

    Under contract-accepting backup offers. Virtually Staged. Short Sale. Investor Special! (short sale requiring 3rd party approval) Don't miss this opportunity to transform this 3-bedroom, 2-bath block home into something truly special. Featuring a newer roof and AC system, some of the major improvements have already been completed, providing a solid foundation for your renovation plans. Whether

    Agent Photo

    Stephen Novak

    LIVE FLORIDA REALTY

    124 Center St, Winter Haven, FL 33880
  • /16

    $2,049 Per Month

    • 3 Beds
    • 2 Baths
    • 2,056 Sq Ft
    • House for Rent

    878 Terranova Rd, 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 $2313.90. That covers your base rent, $2049.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    878 Terranova Rd, Winter Haven, FL 33884
  • /14

    $317,000

    Sold Sep 23, 2025

    3845 Giorgio Dr, Winter Haven, FL 33884

    • 4 Beds
    • 2.5 Baths
    • 2,168 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • $146/SF
    • 265 Days On Market

    Current Estimated Value $329,588

    Meritage Homes VillaMar - Classic Series

    3845 Giorgio Dr, Winter Haven, FL 33884
    • /22

      Not Listed For Sale

      6380 Lolly Bay Loop NE, Winter Haven, FL 33881

      • 2 Beds
      • 2 Baths
      • 1,431 Sq Ft
      • Built 1989
      6380 Lolly Bay Loop NE, Winter Haven, FL 33881

      Last Sold Summary

      • 204 Days On Market

      Last Listing Agent Joyce Frazier JOYCE FRAZIER REALTY

  • /67

    $750,000

    $225K PRICE DROP Under Contract
    • 4 Beds
    • 4 Baths
    • 3,555 Sq Ft

    200 Island Way, Winter Haven, FL 33884

    Under contract-accepting backup offers. MAJOR PRICE IMPROVEMENT! Welcome to your own slice of paradise on the private shores of Lake Lewis located in the highly sought-after gated community of Orchid Springs Estates! This stunning Mediterranean-style estate offers the perfect blend of luxury, comfort, and timeless elegance. Boasting 4 spacious bedrooms and 4 full baths, this custom-designed home

    Agent Photo

    Steve Lockhart

    LOCKHART & ASSOCIATES INC

    200 Island Way, Winter Haven, FL 33884
  • /16

    $1,920 Per Month

    • 4 Beds
    • 2 Baths
    • 2,088 Sq Ft
    • House for Rent

    436 Fish Hawk Dr, Winter Haven, FL 33884

    Please note, our homes are available on a first-come, first-serve basis and are not reserved until the lease is signed by all applicants and security deposits are collected. Interested in this home? You clearly have exceptional taste. This charming 4.0-bedroom, 2.0-bathroom home is not only pet-friendly, but also equipped with smart home features to make everyday life more convenient and

    436 Fish Hawk Dr, Winter Haven, FL 33884
  • /30

    $279,519

    Sold Apr 22, 2026

    272 Meredith Blvd, Winter Haven, FL 33881

    • 4 Beds
    • 2 Baths
    • 1,625 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • $172/SF
    • 9 Days On Market

    Current Estimated Value $275,002

    Dream Finders Homes Willowbrook North

    272 Meredith Blvd, Winter Haven, FL 33881
    • /2

      Est $373,627

      Not Listed For Sale

      359 Mandolin Ln, Winter Haven, FL 33884

      • 4 Beds
      • 2 Baths
      • 2,356 Sq Ft
      • Built 2009
      359 Mandolin Ln, Winter Haven, FL 33884

      Last Sold Summary

      • 60 Days On Market

      Last Listing Agent Renee Butler BROKERS REALTY OF CENTRAL FLOR

  • /75

    $54,990

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

    369 Bern Dr, Winter Haven, FL 33881

    **Please note: the current resident is in the process of packing and preparing for their move. The photos shown were taken when the home was purchased, and the property has remained largely unchanged since then.*** Discover your retirement retreat in the heart of sunny Central Florida! This 2-bedroom, 2-bathroom manufactured home is nestled within Swiss Village, a 55+ active adult community where

    Agent Photo

    Chrissy Walter

    Sunset Home Sales

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

    $1,550 Per Month

    • 1 Bed
    • 1.5 Baths
    • 807 Sq Ft
    • Condo for Rent

    235 6th St NW Unit 608, Winter Haven, FL 33881

    Property Id: 2808642 Charming Downtown Winter Haven Condo with Lake Views Experience the perfect blend of historic charm and modern comfort in this beautiful newly renovated one-bedroom, one-and-a-half-bath condominium located in The Haven Condominiums, a landmark building dating back to 1924 in the heart of downtown Winter Haven. Situated on the 6th floor, this inviting residence

    235 6th St NW Unit 608, Winter Haven, FL 33881
  • /2

    $299,999

    Sold Apr 03, 2026

    5528 Taverna Way, Winter Haven, FL 33884

    • 4 Beds
    • 2.5 Baths
    • 2,039 Sq Ft
    • Built 2025

    Last Sold Summary

    • 12% Below List Price
    • $147/SF
    • 173 Days On Market

    Current Estimated Value $299,145

    Last Listing Agent Dale Human CASA FRESCA REALTY

    5528 Taverna Way, Winter Haven, FL 33884
    • /2

      Est $290,587

      Not Listed For Sale

      4723 Mandolin Loop, Winter Haven, FL 33884

      • 4 Beds
      • 2.5 Baths
      • 1,860 Sq Ft
      • Built 2011
      4723 Mandolin Loop, Winter Haven, FL 33884

      Last Sold Summary

      • 24 Days On Market

      Last Listing Agent Lesley Guarino CITRAVEST MANAGEMENT LLC

  • /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
  • /13

    $1,275 Per Month

    • 2 Beds
    • 1 Bath
    • 1,070 Sq Ft
    • House for Rent

    2750 Ave M NW, Winter Haven, FL 33881

    Property Id: 2849321 We are offering a 2-bedroom, 1-bath house that has very nice floors and new paint. The home also has a carport, 2 sinks in the bathroom, and a very large closet in the master bedroom. Additional features include a large backyard, a large living room and bedrooms, and newer central heat and air. Applicants must pass a background check, prove current income, and have no

    2750 Ave M NW, Winter Haven, FL 33881
  • /2

    $750,000

    Sold Sep 26, 2025

    328 Hamilton Shores Dr NE, Winter Haven, FL 33881

    • 5 Beds
    • 3.5 Baths
    • 3,812 Sq Ft
    • Built 2001

    Last Sold Summary

    • 2% Below List Price
    • $197/SF
    • 56 Days On Market

    Current Estimated Value $754,754

    Last Listing Agent Michael Stone THE STONES REAL ESTATE FIRM

    328 Hamilton Shores Dr NE, Winter Haven, FL 33881
    • /2

      Not Listed For Sale

      313 Thornhill Estates Ct, Winter Haven, FL 33880

      • 3 Beds
      • 2 Baths
      • 1,539 Sq Ft
      • Built 1997
      313 Thornhill Estates Ct, Winter Haven, FL 33880

      Last Sold Summary

      • 42 Days On Market

      Last Listing Agent Debbie Owen WHIPPET PROPERTIES OF FLORIDA LLC

Showing Results 281 - 320, Page 8 of 18

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