48,527

Winter Haven, FL Homes

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  • /46

    $30,000

    • 2 Beds
    • 1 Bath

    574 Century Dr, Winter Haven, FL 33881

    Welcome to your slice of paradise! This charming 2-bedroom, 1-bath home is nestled in a beautiful Florida resort-style park, offering the perfect blend of comfort and relaxation. Enjoy a bright, open living space, a functional kitchen, and cozy bedrooms ideal for full-time living or a seasonal getaway. This home comes partially furnished, making your move-in even easier. Conveniently located

    Agent Photo

    Glenn Fogg

    FOGG MOBILE HOME SALES LLC

    (863) 343-1757

    574 Century Dr, Winter Haven, FL 33881
  • /27

    $1,400 per month

    • 2 Beds
    • 2 Baths
    • 1,017 Sq Ft
    • Condo for Rent

    1101 Eagle Pond Dr, Winter Haven, FL 33884

    Affordability meets Comfort. First Floor unit for easy access in a highly desirable gated community of Cypresswood Golf & Country Club. This rental will include access to community pool, 24-hour security, exterior maintenance, common area taxes, trash service, pest control, and private road upkeep. Residents can also enjoy an 18-hole golf course, on-site restaurant, tennis courts, and a fitness

    Lienyvette Grimaldo MAZELG REALTY

    1101 Eagle Pond Dr, Winter Haven, FL 33884
  • /2

    $360,990 Sold May 27, 2025

    2567 Sage Valley Way, Winter Haven, FL 33884

    • 5 Beds
    • 3 Baths
    • 2,447 Sq Ft
    • Built 2024

    Last Sold Summary

    • 9% Below List Price
    • $148/SF
    • 195 Days On Market

    Current Estimated Value $371,788

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

    2567 Sage Valley Way, Winter Haven, FL 33884
    • /2

      Est $211,337 Not Listed For Sale

      304 Olmo Ct, Winter Haven, FL 33880

      • 3 Beds
      • 2 Baths
      • 1,245 Sq Ft
      • Built 1993
      304 Olmo Ct, Winter Haven, FL 33880

      Last Sold Summary

      • 1% Below List Price
      • $172/SF
      • 8 Days On Market

      Last Sold Price $214,000

      Last Listing Agent Viktoria Strudwick LIVE FLORIDA REALTY

  • /57

    $72,900

    • 2 Beds
    • 2 Baths
    • 1,152 Sq Ft

    8 Captain Kidd Ln SW, Winter Haven, FL 33880

    This beautifully remodeled 2-bedroom, 2-bath home offers 1,254 square feet of comfortable living space in a friendly and active community. The home features a carport and storage shed, providing convenient parking and extra storage. Inside, the home has been completely updated, including all new plumbing, a new electrical main, and newer appliances. Energy-efficient insulated windows and a heat

    Agent Photo

    Glenn Fogg

    FOGG MOBILE HOME SALES LLC

    (863) 485-6496

    8 Captain Kidd Ln SW, Winter Haven, FL 33880
  • /15

    $1,730 per month

    • 4 Beds
    • 2 Baths
    • 1,989 Sq Ft
    • House for Rent

    948 Gotthard Pass Dr, Winter Haven, FL 33881

    We make Pre-Leasing easy! Apply now and, once you’re approved, take this home off the market by paying a Pre-Lease Hold Fee; ask your Leasing Professional for more information. Once the home is made ready, we'll notify you that it's available for touring and for you to accept or decline. If you decline the home, we'll be happy to help you find a different home or refund your Hold Fee. This home

    948 Gotthard Pass Dr, Winter Haven, FL 33881
  • /2

    $380,000 Sold Jan 09, 2026

    204 S Lake Mariam Dr, Winter Haven, FL 33884

    • 3 Beds
    • 2 Baths
    • 1,826 Sq Ft
    • Built 1981

    Last Sold Summary

    • 3% Below List Price
    • $208/SF
    • 63 Days On Market

    Current Estimated Value $375,572

    Last Listing Agent Michael Brenner CENTURY 21 MYERS REALTY

    204 S Lake Mariam Dr, Winter Haven, FL 33884
    • /2

      Est $122,771 Not Listed For Sale

      689 Lake Howard Dr NW Unit 214, Winter Haven, FL 33880

      • 2 Beds
      • 2 Baths
      • 1,072 Sq Ft
      • Built 1976
      689 Lake Howard Dr NW Unit 214, Winter Haven, FL 33880

      Last Sold Summary

      • 2% Below List Price
      • $117/SF
      • 4 Days On Market

      Last Sold Price $124,900

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

  • /18

    $119,000

    • 2 Beds
    • 1 Bath
    • 672 Sq Ft

    220 King Rd, Winter Haven, FL 33880

    ***Invvestor Special*** Welcome to this 2 bedroom 1 bath home. It is in need of some work but not out of range for the right do it your self investor. It is situated on .6 acres of land with room on the back of the lot for a garden, chickens or storage building. This property is located in Winter Haven and is close to everything you need.

    Agent Photo

    Tony Insua Jr.

    CRAIG BURKE REAL ESTATE GROUP, LLC

    (863) 296-3557

    220 King Rd, Winter Haven, FL 33880
  • /24

    $2,000 per month

    • 4 Beds
    • 2 Baths
    • 1,935 Sq Ft
    • House for Rent

    1498 Austin St, Winter Haven, FL 33884

    One or more photo(s) has been virtually staged. Step into this inviting 4 bedroom, 2 bathroom home in the Peace Creek Reserve community, where comfort meets modern style. The split floor plan gives everyone their own space, while the open living, dining, and kitchen area keeps the heart of the home bright, connected, and perfect for everyday life. You’ll love the modern appliances, clean

    Christin Davis PROPERTY MANAGEMENT OF POLK

    1498 Austin St, Winter Haven, FL 33884
  • /2

    $125,000 Sold Aug 06, 2025

    4918 Rosewood St, Winter Haven, FL 33880

    • 2 Beds
    • 2 Baths
    • 1,008 Sq Ft
    • Built 1980

    Last Sold Summary

    • 6% Below List Price
    • $124/SF
    • 96 Days On Market

    Last Listing Agent Kathy Devor COLDWELL BANKER REALTY

    4918 Rosewood St, Winter Haven, FL 33880
    • /2

      Est $960,398 Not Listed For Sale

      2841 Country Club Rd N, Winter Haven, FL 33881

      • 5 Beds
      • 5 Baths
      • 4,664 Sq Ft
      • Built 1995
      2841 Country Club Rd N, Winter Haven, FL 33881

      Last Sold Summary

      • 4% Above List Price
      • $197/SF
      • 25 Days On Market

      Last Sold Price $920,000

      Last Listing Agent Michael Stone THE STONES REAL ESTATE FIRM

  • /48

    $319,900 Pre-Foreclosure

    • 4 Beds
    • 2 Baths
    • 1,944 Sq Ft

    108 Black Skimmer Ln, Winter Haven, FL 33880

    Welcome to your dream home with low HOA fees and no CDD! This 4-bedroom, 2-bathroom home is nestled in the sought-after gated community of Lake Deer. With 1,946 square feet of heated and cooled living space, it's ideal for a growing family! The thoughtful split floor plan ensures privacy and comfort for everyone. The kitchen opens up to a spacious great room with sliding glass doors leading to a

    Agent Photo

    Geraldine Anarumo

    FLORIDA REALTY MARKETPLACE

    (863) 313-1502

    108 Black Skimmer Ln, Winter Haven, FL 33880
  • /34

    $5,339 per month

    • 4 Beds
    • 3 Baths
    • 1,732 Sq Ft
    • Condo for Rent

    904 15th St NE Unit SI FL1-ID1520445P, Winter Haven, FL 33881

    The advertised rate of $5,340/month is the lowest available price, based on a 30 day(s) stay with a move-in date of May 2, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    904 15th St NE Unit SI FL1-ID1520445P, Winter Haven, FL 33881
  • /2

    $389,000 Sold Mar 23, 2026

    1507 Riviera Ct, Winter Haven, FL 33884

    • 3 Beds
    • 2 Baths
    • 1,983 Sq Ft
    • Built 2019

    Last Sold Summary

    • 2% Below List Price
    • $196/SF
    • 21 Days On Market

    Current Estimated Value $397,594

    Last Listing Agent Lori Raath LAKE ASHTON REALTY INC.

    1507 Riviera Ct, Winter Haven, FL 33884
    • /2

      Est $218,197 Not Listed For Sale

      201 6th Jpv St, Winter Haven, FL 33880

      • 3 Beds
      • 1 Bath
      • 1,096 Sq Ft
      • Built 1957
      201 6th Jpv St, Winter Haven, FL 33880

      Last Sold Summary

      • 3% Below List Price
      • $206/SF
      • 209 Days On Market

      Last Sold Price $226,000

      Last Listing Agent Matt Buttner LIST NOW REALTY, LLC

  • /25

    $289,900 Pending

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

    307 Ruby Lake Loop, Winter Haven, FL 33884

    Under contract-accepting backup offers. Discover this charming 4-bedroom, 2-bath home with 1,840 sqft of comfortable living space in the highly desirable Ruby Lake neighborhood in Southeast Winter Haven. Located near LEGOLAND®, this home offers both convenience and a great sense of community. Enjoy the generous bedrooms, including a comfortable primary suite, plus a backyard ready for play or

    Agent Photo

    Steve Lockhart

    LOCKHART & ASSOCIATES INC

    (863) 445-9098

    307 Ruby Lake Loop, Winter Haven, FL 33884
  • /34

    $1,900 per month

    • 3 Beds
    • 2 Baths
    • 1,268 Sq Ft
    • House for Rent

    2893 Whispering Trails Dr, Winter Haven, FL 33884

    This cozy and well-maintained home offers a warm and inviting layout, ideal for comfortable and easy living. The property features a functional floor plan with a modern kitchen, bright and spacious bedrooms, and low-maintenance living areas designed for convenience. Centrally located with quick access to US-27, US-17, SR-540, and I-4, this home provides easy commutes to Orlando and Tampa, as well

    Jenny Caso LIFESTYLE INTERNATIONAL REALTY

    2893 Whispering Trails Dr, Winter Haven, FL 33884
  • /2

    $235,000 Sold Dec 12, 2025

    620 Crystals Blvd, Winter Haven, FL 33884

    • 2 Beds
    • 2 Baths
    • 1,606 Sq Ft
    • Built 1993

    Last Sold Summary

    • 6% Below List Price
    • $146/SF
    • 44 Days On Market

    Current Estimated Value $237,234

    Last Listing Agent Kim Reaves HELLO FLORIDA REAL ESTATE LLC

    620 Crystals Blvd, Winter Haven, FL 33884
    • /2

      Est $146,137 Not Listed For Sale

      40 Kimberly Ct, Winter Haven, FL 33880

      • 2 Beds
      • 2 Baths
      • 1,044 Sq Ft
      • Built 1985
      40 Kimberly Ct, Winter Haven, FL 33880

      Last Sold Summary

      • 12% Above List Price
      • $125/SF
      • 4 Days On Market

      Last Sold Price $130,000

      Last Listing Agent Lamanda Jones CENTURY 21 WATSON & MYERS REALTY

  • /69

    $249,900 Pending

    • 3 Beds
    • 2 Baths
    • 1,681 Sq Ft

    263 Mariposa, Winter Haven, FL 33884

    Under contract-accepting backup offers. VERY SPACIOUS AND A BEAUTIFUL HOME! 2 BONUS ROOMS, HAVE UPDATED JUST ABOUT ALL SYSTEMS INCLUDING: ROOF, DRYWALL, FLOORING, KITCHEN, BATHROOMS, BEDROOMS, A/C, TANKLESS WATER HEATER, ELECTRICAL SYSTEM, PLUMBING, CEILING, INSULATION, AND MORE. LOTS OF SPACIOUS, A LOT OF NATURAL LIGHT. DESIGNER DOORS. OWNER artistically INSPIRED, GIVING THE HOME A UNIQUE FLAIR.

    Agent Photo

    Tina Marie

    TINA MARIE LLC

    (863) 336-6205

    263 Mariposa, Winter Haven, FL 33884
  • /20

    $2,025 per month

    • 4 Beds
    • 2 Baths
    • 2,004 Sq Ft
    • House for Rent

    613 Sarner Pass Way, Winter Haven, FL 33881

    This property is available. Please inquire on this site to schedule a showing. Limited-Time Offer! Sign a lease by April 15th and enjoy $100 off your first month’s rent a great opportunity to save on your new home! Welcome to 613 Sarner Pass Way, located in the serene and charming community of Winter Haven, FL. This delightful single-story home boasts a modern and inviting open

    613 Sarner Pass Way, Winter Haven, FL 33881
  • /2

    $415,000 Sold Dec 15, 2025

    2997 Plantation Rd, Winter Haven, FL 33884

    • 3 Beds
    • 2 Baths
    • 2,603 Sq Ft
    • Built 1986

    Last Sold Summary

    • 5% Below List Price
    • $159/SF
    • 88 Days On Market

    Current Estimated Value $424,850

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

    2997 Plantation Rd, Winter Haven, FL 33884
    • /2

      Not Listed For Sale

      4710 Dogwood St, Winter Haven, FL 33880

      • 2 Beds
      • 2 Baths
      • 1,440 Sq Ft
      • Built 1977
      4710 Dogwood St, Winter Haven, FL 33880

      Last Sold Summary

      • $56/SF
      • 126 Days On Market

      Last Sold Price $81,000

      Last Listing Agent Kathy Devor COLDWELL BANKER REALTY

  • /24

    $189,900

    • 3 Beds
    • 2 Baths
    • 1,784 Sq Ft

    305 Avenue B NE, Winter Haven, FL 33881

    INVESTORS! Take a look at this 1914 Crafstman Bungalow style home! This opportunity is located in the heart of the Winter Haven Heights Historic Residential District that was added to the National Register of Historic Places in 2000! Just 200 feet to the Kiwanis Park on the shores of Lake Martha! Spacious rooms with high ceilings waiting for your imagination are renovation! New Roof 2024! Call

    Agent Photo

    Steve Lockhart

    LOCKHART & ASSOCIATES INC

    (863) 264-6177

    305 Avenue B NE, Winter Haven, FL 33881
  • /15

    $1,895 per month

    • 4 Beds
    • 2 Baths
    • 1,566 Sq Ft
    • House for Rent

    1341 Avenue S NW, Winter Haven, FL 33881

    4/2 home in Winter Haven available now! Features ceramic tile and laminate flooring, inside laundry room, nice yard, and 2 car carport. Approval subject to credit, income, and rental verification.

    Tracey Crews SUPERIOR PROPERTY MGMT & SALES

    1341 Avenue S NW, Winter Haven, FL 33881
  • /2

    $309,990 Sold May 30, 2025

    345 Kayden Cove, Winter Haven, FL 33884

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

    Last Sold Summary

    • $133/SF
    • 14 Days On Market

    Current Estimated Value $341,942

    Last Listing Agent Ben Goldstein LENNAR REALTY

    345 Kayden Cove, Winter Haven, FL 33884
    • /2

      Est $434,751 Not Listed For Sale

      5726 Crystal Beach Rd, Winter Haven, FL 33880

      • 4 Beds
      • 2 Baths
      • 1,964 Sq Ft
      • Built 1928
      5726 Crystal Beach Rd, Winter Haven, FL 33880

      Last Sold Summary

      • 2% Below List Price
      • $227/SF
      • 50 Days On Market

      Last Sold Price $445,000

      Last Listing Agent Ben Becton KELLER WILLIAMS REALTY SMART

  • /12

    $359,999 New Construction

    • 5 Beds
    • 3 Baths
    • 2,471 Sq Ft

    5452 San Pietro Dr, Winter Haven, FL 33884

    Check out the Indigo, a spacious two-story, 5-bedroom, 3-bathroom, 2-car garage home perfect for growing families or hosting guests. Enter the impressive foyer with soaring ceilings that creates an immediate sense of openness. From the foyer, the home effortlessly flows into the main living areas and kitchen. With quartz countertops throughout, stainless-steel appliances and a smart thermostat

    Builder Photo

    Casa Fresca Homes

    Builder

    5452 San Pietro Dr, Winter Haven, FL 33884
  • /15

    $1,560 per month

    • 2 Beds
    • 2 Baths
    • 1,143 Sq Ft
    • House for Rent

    1095 Sunshine Way SW, Winter Haven, FL 33880

    We make Pre-Leasing easy! Apply now and, once you’re approved, take this home off the market by paying a Pre-Lease Hold Fee; ask your Leasing Professional for more information. Once the home is made ready, we'll notify you that it's available for touring and for you to accept or decline. If you decline the home, we'll be happy to help you find a different home or refund your Hold Fee. This home

    1095 Sunshine Way SW, Winter Haven, FL 33880
  • /2

    $422,000 Sold Sep 30, 2025

    235 Meredith Blvd, Winter Haven, FL 33881

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

    Last Sold Summary

    • 7% Below List Price
    • $200/SF
    • 17 Days On Market

    Last Listing Agent Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

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

      Est $291,947 Not Listed For Sale

      4607 Palmetto Dr, Winter Haven, FL 33881

      • 3 Beds
      • 2 Baths
      • 1,412 Sq Ft
      • Built 1996
      4607 Palmetto Dr, Winter Haven, FL 33881

      Last Sold Summary

      • 2% Below List Price
      • $212/SF
      • 7 Days On Market

      Last Sold Price $299,000

      Last Listing Agent Julia Given KELLER WILLIAMS REALTY SMART

  • /62

    $375,000

    • 3 Beds
    • 2 Baths
    • 1,914 Sq Ft

    131 Ruby Lake Dr, Winter Haven, FL 33884

    One or more photo(s) has been virtually staged. Fully refreshed and move-in ready, this Ruby Lake home delivers space, thoughtful upgrades, and a layout that stands out from the rest.Offering high ceilings and a well-designed flow from the L-shaped formal living room that transitions into the formal dining area, creating a defined yet open feel. The kitchen sits at the center with a dinette

    Agent Photo

    CarLee Marchetti

    STAR REALTY OF WINTER HAVEN

    (863) 340-7831

    131 Ruby Lake Dr, Winter Haven, FL 33884
  • /24

    $2,600 per month

    • 4 Beds
    • 3 Baths
    • 2,093 Sq Ft
    • House for Rent

    521 Reggie Rd, Winter Haven, FL 33884

    4 bedroom 3 bathroom Lennar Next Gen home available for lease in Peace Creek Reserve in Winter Haven. This layout features a private mother in law suite with its own entrance, living area, kitchenette, bedroom, and full bath, ideal for multigenerational living or added privacy. Main home offers an open concept floor plan with a large living area, modern kitchen with island, and separate dining

    Michael Hochadel BHHS FLORIDA PROPERTIES GROUP

    521 Reggie Rd, Winter Haven, FL 33884
  • /2

    $255,000 Sold Jan 08, 2026

    6191 Grey Heron Dr, Winter Haven, FL 33881

    • 3 Beds
    • 2 Baths
    • 1,711 Sq Ft
    • Built 2017

    Last Sold Summary

    • 4% Below List Price
    • $149/SF
    • 16 Days On Market

    Current Estimated Value $258,177

    Last Listing Agent Lesley Guarino CITRAVEST MANAGEMENT LLC

    6191 Grey Heron Dr, Winter Haven, FL 33881
    • /2

      Est $217,277 Not Listed For Sale

      260 Avenue V NE, Winter Haven, FL 33881

      • 4 Beds
      • 2 Baths
      • 1,612 Sq Ft
      • Built 1960
      260 Avenue V NE, Winter Haven, FL 33881

      Last Sold Summary

      • 3% Below List Price
      • $140/SF
      • 60 Days On Market

      Last Sold Price $225,000

      Last Listing Agent Laura Auten ELEVATE REALTY LLC

  • /21

    $304,999 New Construction

    • 3 Beds
    • 2 Baths
    • 1,615 Sq Ft

    6006 Navona Way, Winter Haven, FL 33884

    Feel at home with the Magenta, a single-story home with 3 bedrooms, 2 bathrooms, and a 2-car garage. This layout is a true gem, seamlessly blending modern comfort with Florida charm. Open concept living dazzles with luxury vinyl plank flooring throughout the main living areas. The kitchen, featuring quartz countertops, new stainless-steel appliances and ample storage overlooks the dining and

    Builder Photo

    Casa Fresca Homes

    Builder

    6006 Navona Way, Winter Haven, FL 33884
  • /17

    $1,800 per month

    • 3 Beds
    • 2 Baths
    • 1,950 Sq Ft
    • House for Rent

    3236 Timberline Rd, Winter Haven, FL 33880

    Welcome to your dream home! Step inside this pet-friendly home featuring modern finishings and a layout designed with functionality in mind. Enjoy the storage space found in the kitchen and closets as well as the spacious living areas and natural light throughout. Enjoy outdoor living in your yard, perfect for gathering, relaxing, or gardening!Take advantage of the incredible location,

    3236 Timberline Rd, Winter Haven, FL 33880
  • 737 Bayside Blvd, Winter Haven, FL 33881

    $312,900 Sold Dec 24, 2025

    737 Bayside Blvd, Winter Haven, FL 33881

    • 4 Beds
    • 2 Baths
    • 1,819 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • $172/SF
    • 14 Days On Market

    Current Estimated Value $293,980

    Highland Homes Harbor at Lake Henry - Single-Family Homes

    737 Bayside Blvd, Winter Haven, FL 33881
    • /2

      Est $198,747 Not Listed For Sale

      2205 9th Ct NE, Winter Haven, FL 33881

      • 2 Beds
      • 1 Bath
      • 928 Sq Ft
      • Built 1969
      2205 9th Ct NE, Winter Haven, FL 33881

      Last Sold Summary

      • 12% Below List Price
      • $242/SF
      • 186 Days On Market

      Last Sold Price $224,900

      Last Listing Agent Nilka Castro LPT REALTY, LLC

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