48,515

Winter Haven, FL Homes

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  • /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
  • /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

    $340,000 Sold May 30, 2025

    5043 Abigail Dr, Winter Haven, FL 33859

    • 4 Beds
    • 2 Baths
    • 1,598 Sq Ft
    • Built 2025

    Last Sold Summary

    • 4% Below List Price
    • $213/SF
    • 3 Days On Market

    Last Listing Agent Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

    5043 Abigail Dr, Winter Haven, FL 33859
    • /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

  • /61

    $430,000

    • 3 Beds
    • 3.5 Baths
    • 2,576 Sq Ft

    236 W Lake Ina Dr, Winter Haven, FL 33884

    Live the lake life you've been dreaming of in this beautifully maintained 3-bedroom, 2-bath home in Winter Haven! Perfectly positioned for those who love being on the water, this property offers lake access with use of two community docks ideal for boating, fishing, or catching stunning Florida sunsets. Step inside to find a bright, comfortable layout enhanced by new windows that fill the home

    Agent Photo

    Scott Loveridge

    RELENTLESS REAL ESTATE CO.

    (863) 343-1589

    236 W Lake Ina Dr, Winter Haven, FL 33884
  • /16

    $1,740 per month

    • 3 Beds
    • 2 Baths
    • 1,252 Sq Ft
    • House for Rent

    3728 Imperial Dr, Winter Haven, FL 33880

    Beautiful, pet-friendly home coming soon! Apply now, Move-In is available on or after the listed date. Upon approval, $500 reservation deposit to reserve (applied to security deposit and/or refundable). Application fee: $50 per adult. Security Deposit: one month?s rent. Pet fees: $250 + $40/mo per pet. Some homes may include pool ($150/mo), septic ($15/mo), and/or HOA fees; other fees may apply.

    3728 Imperial Dr, Winter Haven, FL 33880
  • /2

    $299,999 Sold Apr 24, 2025

    1536 Hummingbird Rd, Winter Haven, FL 33884

    • 4 Beds
    • 2.5 Baths
    • 1,794 Sq Ft
    • Built 2024

    Last Sold Summary

    • 9% Below List Price
    • $167/SF
    • 255 Days On Market

    Current Estimated Value $308,600

    Last Listing Agent Dale Human CASA FRESCA REALTY

    1536 Hummingbird Rd, Winter Haven, FL 33884
    • /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

  • /2

    $434,900

    • Land
    • 1.57 Acres
    • $277,006 per Acre

    1530 11th St NE, Winter Haven, FL 33881

    Entitled land! 14 Unit townhome development approved and ready for construction immediately! 1.57 acres consisting of 103 feet of lake frontage on Lake Buckeye in Winter Haven. Documents will be provided upon requests.

    Chandler Williams

    EXIT REALTY PREMIER LEGACY

    (863) 563-2453

    1530 11th St NE, Winter Haven, FL 33881
  • /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

    $1,150,000 Sold May 14, 2025

    108 Campbell Dr, Winter Haven, FL 33884

    • 4 Beds
    • 4.5 Baths
    • 5,861 Sq Ft
    • Built 1998

    Last Sold Summary

    • 23% Below List Price
    • $196/SF
    • 230 Days On Market

    Current Estimated Value $1,188,772

    Last Listing Agent Michael Stone THE STONES REAL ESTATE FIRM

    108 Campbell Dr, 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

  • /21

    $59,900

    • 2 Beds
    • 1 Bath
    • 248 Sq Ft

    7041 Fairview Village Cir, Winter Haven, FL 33881

    Welcome to Fairview Village, an active 55+ gated waterfront community in Winter Haven. This charming 2-bedroom home offers peaceful canal and lake views, with private access to the water between Lake Hamilton and Lake Henry—perfect for boating and fishing. The community features a 99-year land lease and a low HOA fee of just $90 per month, which includes water and sewer. Residents enjoy a heated

    Agent Photo

    Sandra Perry

    WATSON REALTY CORP.

    (863) 622-8934

    7041 Fairview Village Cir, Winter Haven, FL 33881
  • /11

    $2,299 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 $2443.90. That covers your base rent, $2299.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

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

    $525,000 Sold Sep 04, 2025

    6112 Pebble Beach Blvd, Winter Haven, FL 33884

    • 3 Beds
    • 2 Baths
    • 2,535 Sq Ft
    • Built 2019

    Last Sold Summary

    • 3% Below List Price
    • $207/SF
    • 9 Days On Market

    Current Estimated Value $512,845

    Last Listing Agent Lori Raath LAKE ASHTON REALTY INC.

    6112 Pebble Beach 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

  • /23

    $224,000

    • 3 Beds
    • 2 Baths
    • 1,444 Sq Ft

    713 Crestwood Dr, Winter Haven, FL 33881

    Solar-powered 3-bedroom home with NO HOA offers flexibility, efficiency, and a layout designed to fit today’s lifestyle. The front living room welcomes you with abundant natural light, creating a bright and inviting space for everyday living or entertaining. The home features both a living room and a separate family room, along with an eat-in kitchen that provides a comfortable space for casual

    Agent Photo

    Tony Baroni

    KELLER WILLIAMS SUBURBAN TAMPA

    (863) 356-0119

    713 Crestwood Dr, Winter Haven, FL 33881
  • /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

    $341,967 Sold May 28, 2025

    1405 Leamington Ln, Winter Haven, FL 33884

    • 4 Beds
    • 2.5 Baths
    • 2,405 Sq Ft
    • Built 2024

    Last Sold Summary

    • 7% Below List Price
    • $142/SF
    • 309 Days On Market

    Current Estimated Value $347,652

    Last Listing Agent Delana Bender TRUE FLORIDA REALTY LLC

    1405 Leamington Ln, 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

  • /22

    $399,900

    • 3 Beds
    • 2 Baths
    • 2,118 Sq Ft

    543 Terranova Cir, Winter Haven, FL 33884

    POOL Home on Pond in TERRANOVA! Located in desirable southeast Winter Haven, this home has it all! Large areas overlooking screened pool and pond frontage and views! Enjoy the security of a gated community close to schools, shopping, churches and LEGOLAND! Call for your private showing today!

    Agent Photo

    Steve Lockhart

    LOCKHART & ASSOCIATES INC

    (863) 356-0796

    543 Terranova Cir, Winter Haven, FL 33884
  • /15

    $2,090 per month

    • 3 Beds
    • 2 Baths
    • 1,444 Sq Ft
    • House for Rent

    437 Kensington View Dr, 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

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

    $365,000 Sold Oct 17, 2025

    236 Golf Aire Blvd, Winter Haven, FL 33884

    • 3 Beds
    • 2.5 Baths
    • 2,523 Sq Ft
    • Built 2000

    Last Sold Summary

    • 15% Below List Price
    • $145/SF
    • 27 Days On Market

    Current Estimated Value $373,680

    Last Listing Agent Amanda Harrison HARRISON REAL PROPERTY GROUP

    236 Golf Aire Blvd, 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

    $364,999 New Construction

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

    5457 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

    5457 San Pietro Dr, Winter Haven, FL 33884
  • /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

    $205,000 Sold May 28, 2025

    3421 Grenville Dr, Winter Haven, FL 33884

    • 2 Beds
    • 2 Baths
    • 1,275 Sq Ft
    • Built 2006

    Last Sold Summary

    • 14% Below List Price
    • $161/SF
    • 124 Days On Market

    Current Estimated Value $213,922

    Last Listing Agent Eileen Belanger CENTURY 21 MYERS REALTY LAKE WALES

    3421 Grenville Dr, Winter Haven, FL 33884
    • /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

  • /39

    $350,000

    • 3 Beds
    • 2 Baths
    • 1,595 Sq Ft

    122 22nd St NW, Winter Haven, FL 33880

    Welcome to your dream oasis—a stunning craftsman-style 3-bedroom, 2-bath saltwater pool home nestled on just over a quarter acre. This charming property features a large front porch, perfect for relaxing with your morning coffee or enjoying beautiful sunsets. Step inside to find a warm and inviting interior with classic crown molding throughout. The formal dining room offers an elegant space for

    Agent Photo

    Michelle Howard

    KELLER WILLIAMS REALTY SMART 1

    (863) 270-4468

    122 22nd St NW, Winter Haven, FL 33880
  • /15

    $1,765 per month

    • 4 Beds
    • 2 Baths
    • 1,786 Sq Ft
    • House for Rent

    107 Fall Glo Rd, Winter Haven, FL 33880

    Please note that the advertised price may exclude additional fees. These include a $55 application fee per applicant; a one-time $75 admin fee; a $11 monthly utility management fee; other mandatory fees, if applicable, for pool maintenance, pet fees/rent, smart home, internet service, and propane refilling; and optional fees for services like self-guided tours with third-party provider Rently

    107 Fall Glo Rd, Winter Haven, FL 33880
  • /2

    $152,250 Sold Apr 08, 2026

    350 Winter Ridge Blvd, Winter Haven, FL 33881

    • 2 Beds
    • 2 Baths
    • 1,073 Sq Ft
    • Built 2000

    Last Sold Summary

    • 2% Below List Price
    • $142/SF
    • 8 Days On Market

    Current Estimated Value $146,236

    Last Listing Agent Nomar Rosa LPT REALTY, LLC

    350 Winter Ridge Blvd, 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

  • /100

    $1,895,000

    • 4 Beds
    • 4 Baths
    • 4,708 Sq Ft

    13 Bogey Dr, Winter Haven, FL 33881

    Opportunities like this are nearly extinct. Just minutes from Winter Haven Country Club, this remarkable estate offers 10.98 acres of privacy, natural beauty, and flexibility in one of Winter Haven’s most coveted and tightly held locations—where land, space, and convenience rarely coexist.The 3,800 sq ft main residence has been completely remodeled with a refined, modern vision that blends

    Agent Photo

    Brock Jennings

    THE MARKET REALTY COMPANY

    (863) 774-3952

    13 Bogey Dr, Winter Haven, FL 33881
  • /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

    $160,000 Sold Feb 20, 2026

    398 Winter Ridge Blvd Unit 398, Winter Haven, FL 33881

    • 2 Beds
    • 2 Baths
    • 1,241 Sq Ft
    • Built 1996

    Last Sold Summary

    • 3% Above List Price
    • $129/SF
    • 106 Days On Market

    Last Listing Agent CarLee Marchetti STAR REALTY OF WINTER HAVEN

    398 Winter Ridge Blvd Unit 398, 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

  • /44

    $138,900

    • 2 Beds
    • 2 Baths
    • 1,040 Sq Ft

    409 Village Cir SW, Winter Haven, FL 33880

    Charming and well maintained! 2-Bedroom 2- Bath Home in Desirable 55+ Community – You Own the Land with low HOA fees!This inviting home features fresh interior and exterior paint and a newly screened-in front porch, perfect for enjoying your morning coffee, afternoon tea or just relaxing in the Florida breeze. The property also offers a fenced-in backyard, ideal for pets to play or

    Agent Photo

    Michelle Armbruster

    LOCKHART & ASSOCIATES INC

    (863) 340-7516

    409 Village Cir 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

    $250,000 Sold Feb 24, 2026

    509 Mckenna Dr, Winter Haven, FL 33881

    • 3 Beds
    • 2 Baths
    • 1,506 Sq Ft
    • Built 2020

    Last Sold Summary

    • 3% Below List Price
    • $166/SF
    • 191 Days On Market

    Current Estimated Value $255,100

    Last Listing Agent EJ Jimenez KELLER WILLIAMS ADVANTAGE III

    509 Mckenna Dr, Winter Haven, FL 33881
    • /2

      Est $156,507 Not Listed For Sale

      2420 Edwin St NE, Winter Haven, FL 33881

      • 4 Beds
      • 2 Baths
      • 1,194 Sq Ft
      • Built 1950
      2420 Edwin St NE, Winter Haven, FL 33881

      Last Sold Summary

      • 4% Above List Price
      • $126/SF
      • 14 Days On Market

      Last Sold Price $150,000

      Last Listing Agent Raymond Reyes LPT REALTY, LLC

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