48,350

Winter Haven, FL Homes

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  • /59

    $387,500

    • 4 Beds
    • 2 Baths
    • 2,078 Sq Ft

    5828 Marsh Landing Dr, Winter Haven, FL 33881

    Welcome to refined Florida living in the serene, gated, 55+ community of Preserve at Lakeside Landings. This community designed with enjoying your Florida lifestyle, is home to 44 residences, 2 pools, a playground, and sidewalks to keep you active. HOA includes lawn maintenance which allows you to relax in your stunning new home! Thoughtfully designed with a triple-split floorplan, this residence

    Agent Photo

    Cyleste Goodson

    FLORIDA REAL ESTATE COMPANY

    (863) 312-0317

    5828 Marsh Landing Dr, Winter Haven, FL 33881
  • /20

    $2,099 per month

    • 3 Beds
    • 2 Baths
    • 1,888 Sq Ft
    • House for Rent

    Unlisted Address

    Take a look at this beautiful home, Clean and Move-In Ready, featuring 3 bedrooms,2 bathrooms, 2 car garage and approximately 1,888 heated square feet. Enjoy the freedom of a virtually maintenance free lifestyle while residing in a great community. Smart Home Tech - $21.95/mo; Washer/Dryer - $35/mo; High Speed Cable/Internet (if applicable by 3rd Party user) $55/mo; Renters insurance reqrd, Pool

    Cathy Behe TAH FLORIDA LLC

    Unlisted Address
  • /2

    $55,000 Sold Jul 11, 2025

    4151 Sprucewood St, Winter Haven, FL 33880

    • 2 Beds
    • 2 Baths
    • 864 Sq Ft
    • Built 1982

    Last Sold Summary

    • 42% Below List Price
    • $64/SF
    • 107 Days On Market

    Last Listing Agent Brandy Duncan COLDWELL BANKER REALTY

    4151 Sprucewood St, Winter Haven, FL 33880
    • /2

      Est $487,237 Not Listed For Sale

      1086 Brimstone Cir, Winter Haven, FL 33884

      • 5 Beds
      • 3 Baths
      • 3,297 Sq Ft
      • Built 2024
      1086 Brimstone Cir, Winter Haven, FL 33884

      Last Sold Summary

      • 1% Below List Price
      • $149/SF
      • 58 Days On Market

      Last Sold Price $489,995

      Last Listing Agent Dale Human CASA FRESCA REALTY

  • /39

    $186,000

    • 2 Beds
    • 2 Baths
    • 1,017 Sq Ft

    307 Eagle Pond Dr, Winter Haven, FL 33884

    PRICE ADJUSTMENT ALERT—the opportunity you've been waiting for! Welcome to easy, low-maintenance living in the 24/7 guard-gated Cypresswood Golf & Country Club. This charming condo offers peaceful POND VIEWS from the living room and both bedrooms, creating the perfect backdrop for relaxing mornings and quiet evenings.Inside, you'll love the bright, open layout with 10' ceilings, rich wood

    Agent Photo

    Mabel Vassallo

    CENTURY 21 MYERS REALTY

    (863) 431-4399

    307 Eagle Pond Dr, Winter Haven, FL 33884
  • /15

    $1,032 - $1,495 per month

    Briarcrest at Winter Haven

    1 - 3 Beds

    200 Avenue K SE, Winter Haven, FL 33880

    Welcome to Briarcrest at Winter Haven Apartments, ideally located near downtown Winter Haven, FL where convenience meets comfort in a picturesque setting. Choose from our spacious and versatile one, two, and three-bedroom floor plans, each thoughtfully designed to suit diverse lifestyles. Our community boasts not just one, but two sparking pools for residents to unwind and enjoy Florida's

    200 Avenue K SE, Winter Haven, FL 33880
  • /2

    $95,000 Sold Jul 01, 2025

    256 Lakeside Ranch Cir, Winter Haven, FL 33881

    • 2 Beds
    • 2 Baths
    • 1,104 Sq Ft
    • Built 1978

    Last Sold Summary

    • 21% Below List Price
    • $86/SF
    • 92 Days On Market

    Last Listing Agent Lynne Halleran COLDWELL BANKER REALTY

    256 Lakeside Ranch Cir, Winter Haven, FL 33881
    • /2

      Est $978,188 Not Listed For Sale

      856 Twin Oaks Ln, Winter Haven, FL 33880

      • 4 Beds
      • 3 Baths
      • 3,237 Sq Ft
      • Built 2018
      856 Twin Oaks Ln, Winter Haven, FL 33880

      Last Sold Summary

      • $303/SF
      • 141 Days On Market

      Last Sold Price $980,000

      Last Listing Agent Michael Stone THE STONES REAL ESTATE FIRM

  • /31

    $69,000

    • 3 Beds
    • 2 Baths
    • 1,512 Sq Ft

    1006 Eagle Dr, Winter Haven, FL 33881

    Step into this stunning furnished 3-bedroom, 2-bath home with a den, offering over 1,500 sq. ft. of beautifully designed living space PLUS a huge enclosed Florida room with heat and AC-perfect for year-round enjoyment! You'll love the bright open living and dining area and the spacious kitchen featuring tons of counter and cabinet space along with a built-in desk for convenience. An interior

    Agent Photo

    Cindy Minnick

    Sun Resales, Inc.

    (863) 223-4692

    1006 Eagle Dr, Winter Haven, FL 33881
  • /8

    $1,800 per month

    • 4 Beds
    • 2 Baths
    • 1,822 Sq Ft
    • House for Rent

    2363 Twin Lake View Rd, Winter Haven, FL 33881

    MOVE-IN READY in Winter Haven!? Looking for a remodeled home with space, style, and a fenced yard? This 4BR/2BA beauty in Eagle Crest checks every box! Fresh + Updated Vaulted ceilings & wood-look floors Bright kitchen w/ stainless steel appliances Open living & dining leading to a covered lanai Spacious primary suite w/ dual vanities + soaking tub Interior laundry 2-car garage. Fully fenced

    Maria Villacis AVANTI WAY REALTY LLC

    2363 Twin Lake View Rd, Winter Haven, FL 33881
  • /2

    $250,000 Sold Jun 30, 2025

    216 Kingshill Ct SE, Winter Haven, FL 33884

    • 3 Beds
    • 2 Baths
    • 1,462 Sq Ft
    • Built 1990

    Last Sold Summary

    • $171/SF
    • 3 Days On Market

    Current Estimated Value $254,238

    Last Listing Agent Ce Ce Devereaux DALTON WADE INC

    216 Kingshill Ct SE, Winter Haven, FL 33884
    • /2

      Est $339,735 Not Listed For Sale

      5771 Marsh Landing Dr, Winter Haven, FL 33881

      • 4 Beds
      • 2 Baths
      • 2,368 Sq Ft
      • Built 2017
      5771 Marsh Landing Dr, Winter Haven, FL 33881

      Last Sold Summary

      • 7% Above List Price
      • $135/SF
      • 27 Days On Market

      Last Sold Price $318,500

      Last Listing Agent Justen Davila Rivas EXP REALTY LLC

  • /71

    $445,000

    • 3 Beds
    • 2 Baths
    • 2,363 Sq Ft

    5357 Hogan Ln, Winter Haven, FL 33884

    One or more photo(s) has been virtually staged. WATERFRONT CUSTOM St. John floor plan with CDD bond debt PAID IN FULL! A true gem in Lake Ashton. Recent Upgrades: Kinetico whole-house water softener, refrigerator (2025), New roof (2024), AC, dishwasher, stove, additional screened room with pavers, and upgraded landscaping (2022). Experience Florida living at its finest in this beautifully

    Agent Photo

    Emily Muscarella

    A+ REALTY LLC

    (863) 431-8559

    5357 Hogan Ln, Winter Haven, FL 33884
  • /12

    $1,205 - $1,598 per month

    Barrington Place At Winter Haven

    1 - 2 Beds

    1101 Cambridge Square, Winter Haven, FL 33880

    Barrington Place at Winter Haven is an intimate and charming community located in Winter Haven, FL. Our exclusive residences offer a serene retreat for residents seeking comfort and convenience. Discover the perfect balance of tranquility and accessibility, with proximity to Cypress Gardens Blvd., top-rated schools, healthcare facilities, and shopping destinations just moments away. Choose from

    1101 Cambridge Square, Winter Haven, FL 33880
  • /2

    $300,000 Sold Apr 15, 2025

    5341 Nicklaus Dr, Winter Haven, FL 33884

    • 2 Beds
    • 2 Baths
    • 1,530 Sq Ft
    • Built 2006

    Last Sold Summary

    • 12% Below List Price
    • $196/SF
    • 41 Days On Market

    Current Estimated Value $302,368

    Last Listing Agent Lori Raath LAKE ASHTON REALTY INC.

    5341 Nicklaus Dr, Winter Haven, FL 33884
    • /2

      Est $452,335 Not Listed For Sale

      4002 Bedford Ave, Winter Haven, FL 33884

      • 4 Beds
      • 3 Baths
      • 2,650 Sq Ft
      • Built 2017
      4002 Bedford Ave, Winter Haven, FL 33884

      Last Sold Summary

      • 2% Below List Price
      • $174/SF
      • 23 Days On Market

      Last Sold Price $460,000

      Last Listing Agent Steven Koleno BEYCOME OF FLORIDA LLC

  • /18

    $69,500

    • 2 Beds
    • 2 Baths
    • 792 Sq Ft

    471 Putter Cir, Winter Haven, FL 33881

    Welcome to your dream oasis! This stunning 2-bedroom, 2-bathroom home is a perfect blend of comfort and style. Step into a beautifully renovated kitchen that will inspire your inner chef! Enjoy the luxury of updated bathrooms, including a fabulous primary bath. The spacious enclosed Florida Room, equipped with HVAC, is perfect for year-round relaxation and adding an additional 160 sq ft. Plus,

    Agent Photo

    Cindy Minnick

    Sun Resales, Inc.

    (863) 622-7245

    471 Putter Cir, Winter Haven, FL 33881
  • /20

    $1,500 per month

    • 1 Bed
    • 1 Bath
    • 2,093 Sq Ft
    • House for Rent

    1313 Diego Terrace Unit In-Law Suite, Winter Haven, FL 33884

    One or more photo(s) has been virtually staged. For Rent: Charming In-Law Suite in Winter Haven, FL – $1,500/Month Looking for a cozy and private living space in a beautiful community? This in-law suite in Winter Haven, FL offers comfort, convenience, and access to great amenities. Key Features: Monthly Rent: $1,500 Lease Term: Minimum 12 months Security Deposit: $1,500 Requirements: First

    Andrea Jastemski DALTON WADE INC

    1313 Diego Terrace Unit In-Law Suite, Winter Haven, FL 33884
  • /2

    $314,990 Sold May 27, 2025

    1606 Teagan Ln, Winter Haven, FL 33884

    • 4 Beds
    • 3 Baths
    • 2,174 Sq Ft
    • Built 2025

    Last Sold Summary

    • 5% Below List Price
    • $145/SF
    • 37 Days On Market

    Current Estimated Value $319,829

    Last Listing Agent Ben Goldstein LENNAR REALTY

    1606 Teagan Ln, Winter Haven, FL 33884
    • /2

      Est $343,448 Not Listed For Sale

      3180 Lake Dr NW, Winter Haven, FL 33881

      • 3 Beds
      • 3 Baths
      • 1,821 Sq Ft
      • Built 2023
      3180 Lake Dr NW, Winter Haven, FL 33881

      Last Sold Summary

      • 3% Above List Price
      • $184/SF
      • 65 Days On Market

      Last Sold Price $335,000

      Last Listing Agent Jason Gregory DALTON WADE INC

  • /18

    $225,555

    • 3 Beds
    • 1.5 Baths
    • 1,204 Sq Ft

    112 Harbor Dr, Winter Haven, FL 33881

    Welcome to Your Dream Home! Discover this fully updated ranch-style home, featuring a brand new roof and a beautifully renovated kitchen and bathroom. Situated on a quiet street with no HOA fees, this property offers both peace and affordability. Enjoy close proximity to parks and highways, making it a convenient choice for your lifestyle. This home is perfect for first-time buyers or anyone

    Agent Photo

    Farzana Zalil

    CHARLES RUTENBERG REALTY ORLANDO

    (863) 231-0623

    112 Harbor Dr, Winter Haven, FL 33881
  • /50

    $1,283 - $1,608 per month

    Vista Lake Ned

    1 - 3 Beds

    4025 Lake Ned Village Cir, Winter Haven, FL 33884

    Flow through the good life at Vista Lake Ned Apartments. The park-like setting, eclectic amenities, and expansive interiors will make you fall in love with our apartments in Winter Haven. Even better, our Cypress Gardens location places you right off Highway 27 and close to Legoland! Add in the top-notch services that have earned us glowing reviews throughout the years, and you know you're in the

    4025 Lake Ned Village Cir, Winter Haven, FL 33884
  • /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 $286,667

    Starlight Homes Sunset Hills

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

      Est $348,105 Not Listed For Sale

      3726 Plymouth Dr, Winter Haven, FL 33884

      • 2 Beds
      • 2 Baths
      • 1,797 Sq Ft
      • Built 2017
      3726 Plymouth Dr, Winter Haven, FL 33884

      Last Sold Summary

      • 1% Below List Price
      • $195/SF
      • 153 Days On Market

      Last Sold Price $350,000

      Last Listing Agent Eileen Belanger CENTURY 21 MYERS REALTY LAKE WALES

  • /15

    $275,000

    • 3 Beds
    • 2 Baths
    • 1,732 Sq Ft

    3180 Country Club Cir, Winter Haven, FL 33881

    Short Sale. BANKRUPTCY SHORT SALE! Located In The Country Walk Community, This 2019 Built Home At 3180 Country Club Cir, Winter Haven, FL 33881 Features The Popular DR Horton Aria Floor Plan Offering 3 Bedrooms, 2 Bathrooms, & 1,672 Sq Ft Of Living Space. This Home Offers an Open Concept Layout With A Spacious Living Area, Split Bedroom Floor Plan, & a Functional Kitchen Overlooking The Main

    Agent Photo

    Jon McCall PA

    DALTON WADE INC

    (863) 250-1507

    3180 Country Club Cir, Winter Haven, FL 33881
  • /11

    $1,299 per month

    • 3 Beds
    • 2 Baths
    • 876 Sq Ft
    • House for Rent

    226 Avenue S NE, Winter Haven, FL 33881

    This 3-bedroom home features a beautifully redone interior with fresh updates throughout. Bedrooms include comfortable carpeting, while the rest of the home offers a clean, updated look that’s move-in ready. Located just steps from Lake Maude, providing easy access to walking paths, water views, and outdoor recreation.CALL TODAY TO VIEW

    Jordan Clark PALM LEAF PROPERTY MANAGEMENT

    226 Avenue S NE, Winter Haven, FL 33881
  • /33

    $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

    Current Estimated Value $369,000

    Dream Finders Homes Willowbrook North

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

      Est $342,495 Not Listed For Sale

      1013 Sawgrass Dr, Winter Haven, FL 33884

      • 2 Beds
      • 2 Baths
      • 1,824 Sq Ft
      • Built 2020
      1013 Sawgrass Dr, Winter Haven, FL 33884

      Last Sold Summary

      • 4% Above List Price
      • $181/SF
      • 146 Days On Market

      Last Sold Price $330,000

      Last Listing Agent Brad Kirwan GLOBAL LIFESTYLE LLC

  • /24

    $250,500

    • 3 Beds
    • 1 Bath
    • 985 Sq Ft

    2122 Lake Blvd, Winter Haven, FL 33881

    Enjoy relaxed Florida living with beautiful lake views right from the front of this inviting home. Filled with natural light, the comfortable layout offers an easy, functional flow that makes everyday living and entertaining feel effortless. The thoughtfully designed interior keeps maintenance simple while maximizing comfort and usability.One of the home’s standout features is the fully

    Agent Photo

    Catherine Torres

    IAD FLORIDA LLC

    (863) 264-0380

    2122 Lake Blvd, Winter Haven, FL 33881
  • /39

    $1,503 - $2,383 per month

    Raindance

    1 - 2 Beds

    200 Avenue C SW, Winter Haven, FL 33880

    Welcome Home to Raindance!

    200 Avenue C SW, Winter Haven, FL 33880
  • /2

    $345,000 Sold Mar 14, 2025

    3852 Giorgio Dr, Winter Haven, FL 33884

    • 4 Beds
    • 3 Baths
    • 2,387 Sq Ft
    • Built 2024

    Last Sold Summary

    • 2% Below List Price
    • $145/SF
    • 5 Days On Market

    Current Estimated Value $346,069

    Last Listing Agent Tatiana Souza FLORIDA CONNEXION PROPERTIES

    3852 Giorgio Dr, Winter Haven, FL 33884
    • /2

      Est $262,005 Not Listed For Sale

      4651 Ostero St, Winter Haven, FL 33884

      • 4 Beds
      • 2 Baths
      • 1,665 Sq Ft
      • Built 2024
      4651 Ostero St, Winter Haven, FL 33884

      Last Sold Summary

      • 2% Below List Price
      • $161/SF
      • 190 Days On Market

      Last Sold Price $268,080

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

  • /45

    $179,900

    • 2 Beds
    • 2 Baths
    • 2,208 Sq Ft

    194 Fairway Cir, Winter Haven, FL 33881

    This beautifully updated 2-bedroom, 2-bathroom unfurnished home offers modern comfort and timeless charm, nestled on a spacious private lot along the 14th hole of the golf course. Step inside to discover a fully renovated interior featuring luxury finishes throughout. A chef's dream kitchen, boasting a 5' double-door pantry, additional storage closet with shelving, tile backsplash, deep

    Agent Photo

    Cindy Minnick

    Sun Resales, Inc.

    (863) 336-6201

    194 Fairway Cir, Winter Haven, FL 33881
  • /11

    $1,975 per month

    • 4 Beds
    • 2 Baths
    • 2,150 Sq Ft
    • House for Rent

    2702 Rochelle Dr, Winter Haven, FL 33881

    HOME IS REALTY BEAUTIFUL WIDE OPEN FLOOR PLAN. VAULTED CEILING IN PART OF HOME. A MUST TO SEE.

    William Beasley STAR REALTY OF WINTER HAVEN

    2702 Rochelle Dr, Winter Haven, FL 33881
  • /2

    $282,990 Sold Apr 24, 2025

    3440 Costello Cir, Winter Haven, FL 33884

    • 4 Beds
    • 2 Baths
    • 1,665 Sq Ft
    • Built 2025

    Last Sold Summary

    • 4% Below List Price
    • $170/SF
    • 52 Days On Market

    Current Estimated Value $272,031

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

    3440 Costello Cir, Winter Haven, FL 33884
    • /2

      Est $307,657 Not Listed For Sale

      4905 Kaia Ave, Winter Haven, FL 33884

      • 4 Beds
      • 2 Baths
      • 1,840 Sq Ft
      • Built 2024
      4905 Kaia Ave, Winter Haven, FL 33884

      Last Sold Summary

      • 2% Above List Price
      • $165/SF
      • 213 Days On Market

      Last Sold Price $303,000

      Last Listing Agent Tatiana Souza FLORIDA CONNEXION PROPERTIES

  • /22

    $48,000

    • 2 Beds
    • 2 Baths

    625 Century Dr, Winter Haven, FL 33881

    This 940 sq ft home offers an open floor plan and a bright Florida room at the front of the house-perfect for relaxing or morning coffee. Recent improvements include new plumbing throughout (10/2023), a newer roof (2023), and an AC system installed around 2020. The home features convenient stackable inside laundry and a large shed for extra storage. A wonderful opportunity to make this home your

    Agent Photo

    Cindy Minnick

    Sun Resales, Inc.

    (863) 270-3168

    625 Century Dr, Winter Haven, FL 33881
  • /26

    $1,160 - $1,575 per month

    Della Vita Apartments

    1 - 3 Beds

    4200 Mahogany Run, Winter Haven, FL 33884

    Della Vita Apartments offers the best in brand new interior finishes, abundant community amenity offerings and quick and easy access to some of the best shopping, entertainment and dining Winter Haven has to offer. We’ve recently started a multi-million dollar renovation that will enhance your everyday lifestyle. Our 1, 2 & 3 bedroom apartment homes include large bedrooms with walk-in closets,

    4200 Mahogany Run, Winter Haven, FL 33884
  • /2

    $267,900 Sold Aug 17, 2025

    2021 Oliver Place, Winter Haven, FL 33881

    • 3 Beds
    • 2 Baths
    • 1,627 Sq Ft
    • Built 1967

    Last Sold Summary

    • 1% Below List Price
    • $165/SF
    • 21 Days On Market

    Current Estimated Value $264,246

    Last Listing Agent Glen Barron C BUDDY JOHNSON REALTY, LLC

    2021 Oliver Place, Winter Haven, FL 33881
    • /2

      Est $305,211 Not Listed For Sale

      3852 Eloise Estates Ct, Winter Haven, FL 33881

      • 4 Beds
      • 2 Baths
      • 1,867 Sq Ft
      • Built 2014
      3852 Eloise Estates Ct, Winter Haven, FL 33881

      Last Sold Summary

      • 3% Below List Price
      • $169/SF
      • 216 Days On Market

      Last Sold Price $316,000

      Last Listing Agent Adrianna Darr KELLER WILLIAMS REALTY SMART

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