48,939

Winter Haven, FL Homes

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  • /37

    $290,000

    $25K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,770 Sq Ft

    1085 Brenton Manor Dr, Winter Haven, FL 33881

    Charming and inviting, this 3-bed, 2-bath home sits in a lovely Winter Haven community with a very low HOA. Built in 2015, it offers a modern design, a comfortable one-level layout, a 2-car garage, and all appliances included. Tucked into the vibrant Chain of Lakes region, you’re surrounded by peaceful views, leafy lakes, and plenty of outdoor fun from boat cruises to paddle boarding. And when

    Agent Photo

    Clarisa Moody

    MARZUCCO REAL ESTATE

    (863) 900-9378

    1085 Brenton Manor Dr, Winter Haven, FL 33881
  • /35

    $2,400 Per Month

    • 4 Beds
    • 2 Baths
    • 1,791 Sq Ft
    • House for Rent

    330 Royal Palm Way, Winter Haven, FL 33881

    Be one of the first to move into these recently built, energy-efficient homes, LOADED with the best finishes. If you have pets, not only do we allow them, but we have homes available that include a fenced-in yard! Landscape is included! All appliances are included! The interior finishes include wood look tile throughout, modern kitchens with quartz appliances and stainless steel appliances, 100%

    (863) 267-8759

    330 Royal Palm Way, Winter Haven, FL 33881
  • /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 $261,954

      Not Listed For Sale

      724 Avenue R NE, Winter Haven, FL 33881

      • 3 Beds
      • 2 Baths
      • 1,332 Sq Ft
      • Built 2024
      724 Avenue R NE, Winter Haven, FL 33881

      Last Sold Summary

      • 205 Days On Market

  • /25

    $265,000

    Pending
    • 3 Beds
    • 2 Baths
    • 1,379 Sq Ft

    8 Saint Kitts Cir, Winter Haven, FL 33884

    Welcome to 8 St. Kitts Circle in Winter Haven—a move-in ready home that checks all the right boxes. Freshly painted and well-maintained, this property offers comfort and peace of mind with a metal roof (2023) and a newer A/C unit (2020). Even better, a brand-new water heater will be installed prior to closing, making this home truly ready for its next owner. Step outside to enjoy the vinyl-fenced

    Agent Photo

    Michelle Smith

    KELLER WILLIAMS REALTY SMART 1

    (863) 344-3920

    8 Saint Kitts Cir, Winter Haven, FL 33884
  • /14

    Starting at $1,000 Per Month

    • Studio - 2 Beds

    130 Avenue C SE, Winter Haven, FL 33880

    Central Haven Apartments

    (863) 837-4828

    130 Avenue C SE, Winter Haven, FL 33880
  • /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 $292,140

    Last Listing Agent Mike Nolen COLDWELL BANKER REALTY

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

      Est $237,671

      Not Listed For Sale

      275 Cherry Laurel Ln, Winter Haven, FL 33880

      • 3 Beds
      • 2 Baths
      • 1,232 Sq Ft
      • Built 1980
      275 Cherry Laurel Ln, Winter Haven, FL 33880

      Last Sold Summary

      • 5 Days On Market

  • /45

    $459,000

    Open Tue 4PM - 6PM $6K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,663 Sq Ft

    148 Lake Otis Rd, Winter Haven, FL 33884

    Spacious 4-Bedroom, 3-Bath Pool Home in the admired Lakewood Community. Nestled on an oversized lot with mature trees, this remodeled tri-level home offers a perfect blend of modern luxury and comfort. With a spacious layout, a private pool, and an abundance of natural light, this home is designed for both relaxation and entertaining. As you enter, you’ll immediately notice the bright and airy

    Agent Photo

    Michelle Armbruster

    LOCKHART & ASSOCIATES INC

    (863) 599-6261

    148 Lake Otis Rd, Winter Haven, FL 33884
  • /31

    $1,800

    Total Monthly Price

    • 4 Beds
    • 2 Baths
    • 1,368 Sq Ft
    • House for Rent

    3960 Avenue U NW, Winter Haven, FL 33881

    Don't miss out on this 4 bedroom home, at an amazing price. This home has been freshly painted and has ceramic tile throughout. The French doors lead to a paver patio that provides access to a huge backyard. The uncovered gazebo/patio area is perfect for those fire pit evenings. Your front covered patio gives you a Waterview of Lake Blue.

    (863) 281-6376

    3960 Avenue U 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 $310,000

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

    4125 Giorgio Dr, Winter Haven, FL 33884
    • /2

      Est $171,198

      Not Listed For Sale

      841 4th St, Winter Haven, FL 33881

      • 3 Beds
      • 2 Baths
      • 912 Sq Ft
      • Built 1901
      841 4th St, Winter Haven, FL 33881

      Last Sold Summary

      • 103 Days On Market

  • /49

    $290,000

    Open Tue 12AM - 11:59PM
    • 3 Beds
    • 2 Baths

    542 Eagle Landing Blvd, Winter Haven, FL 33880

    Welcome to the Eagle Landing community in Winter Haven, FL. This well-maintained single-family home is move-in ready and waiting for its new owner(s). The open-floor concept creates a comfortable flow throughout the main living areas, while the split floor plan provides added privacy for the primary bedroom and bath with spacious walk-in closet.The kitchen features stainless steel appliances

    Agent Photo

    Carla Miro

    CENTURY 21 WATSON & MYERS REAL

    (863) 312-0574

    542 Eagle Landing Blvd, Winter Haven, FL 33880
  • /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

    (863) 877-4288

    745 Avenue A SW, Winter Haven, FL 33880
  • /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 $255,381

    Last Listing Agent Ce Ce Devereaux DALTON WADE INC

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

      Est $494,401

      Not Listed For Sale

      1055 Lena Run Ct, Winter Haven, FL 33880

      • 4 Beds
      • 3 Baths
      • 2,636 Sq Ft
      • Built 2014
      1055 Lena Run Ct, Winter Haven, FL 33880

      Last Sold Summary

      • 61 Days On Market

  • /43

    $364,999

    $95K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,907 Sq Ft

    6003 Live Oak Dr, Winter Haven, FL 33880

    Honey, stop the car! This is the one you’ve been waiting for.This beautifully maintained 4-bedroom, 2-bathroom home sits on a spacious 0.45-acre fenced lot, offering the space, privacy, and outdoor lifestyle today’s buyers are searching for. Enjoy the soon-to-be easy access to Avalon and Disney via Sawgrass Rd extension.Step inside and you’re welcomed by a spacious foyer that flows into a

    Agent Photo

    Paul Shearn

    FUTURE HOME REALTY INC

    (863) 204-4704

    6003 Live Oak Dr, Winter Haven, FL 33880
  • /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

    (855) 606-5243

    101-123 Oak Crest Dr NW, Winter Haven, FL 33881
  • /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
    • /2

      Not Listed For Sale

      4076 Rolling Oaks Dr, Winter Haven, FL 33880

      • 2 Beds
      • 2 Baths
      • 1,200 Sq Ft
      • Built 1983
      4076 Rolling Oaks Dr, Winter Haven, FL 33880

      Last Sold Summary

      • 3 Days On Market

  • /16

    $114,000

    $6K 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

    (863) 434-8323

    831 Orchid Springs Dr Unit 831, Winter Haven, FL 33884
  • /18

    Starting at $899 Per Month

    • 1 - 2 Beds

    102 Landings Way, Winter Haven, FL 33880

    Welcome to The Landings, a tranquil pet friendly retreat nestled among towering trees and lush greenery in the heart of Winter Haven, Florida. As one of our three Winter Haven locations, The Landings offers upgraded 1 and 2 bedroom apartments designed with spacious layouts that maximize comfort and livability. Each home features modern white cabinets that brighten the space, durable vinyl

    The Landings Apartment Homes

    (863) 251-5637

    102 Landings Way, Winter Haven, FL 33880
  • /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 $319,547

    Starlight Homes Sunset Hills

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

      Est $158,448

      Not Listed For Sale

      262 Ware Ave NE, Winter Haven, FL 33881

      • 2 Beds
      • 1 Bath
      • 816 Sq Ft
      • Built 1963
      262 Ware Ave NE, Winter Haven, FL 33881

      Last Sold Summary

      • 229 Days On Market

  • /33

    $18,000

    $232K PRICE DROP Pending
    • 3 Beds
    • 2 Baths
    • 1,410 Sq Ft

    936 Avenue T SE, Winter Haven, FL 33880

    Short Sale. Welcome to this beautiful 3-bedroom, 2-bathroom block home perfectly positioned at the end of a quiet cul-de-sac in Winter Haven's sought-after Cypress Gardens neighborhood. With 1,400 square feet of interior living space and a layout designed for both comfort and connection, this home checks every box. Step inside and you're immediately greeted by a bright, open floor plan where the

    Agent Photo

    Daniel Rodriguez

    NEW HEIGHTS REALTY GROUP

    (863) 285-3066

    936 Avenue T SE, Winter Haven, FL 33880
  • /18

    $1,990 Per Month

    • 3 Beds
    • 2 Baths
    • 1,930 Sq Ft
    • House for Rent

    2112 Jonathan Ln, 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 $2134.90. That covers your base rent, $1990.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    (863) 509-1961

    2112 Jonathan Ln, Winter Haven, FL 33884
  • /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 $236,302

    Last Listing Agent Chrissi Jasso ASSOCIATE REALTY

    144 Brad Cir, Winter Haven, FL 33880
    • /44

      Est $308,011

      Not Listed For Sale

      7146 Summit Dr, Winter Haven, FL 33884

      • 3 Beds
      • 2 Baths
      • 1,842 Sq Ft
      • Built 2004
      7146 Summit Dr, Winter Haven, FL 33884

      Last Sold Summary

      • 38 Days On Market

  • /31

    $55,500

    $14K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,920 Sq Ft

    488 Putter Cir, Winter Haven, FL 33881

    Welcome to this delightful 2-bedroom, 2-bath home where comfort meets convenience. Recent updates include a new AC (2025) and roof (2024), giving you peace of mind for years to come. A circular driveway and golf cart make life easy, while a large shed offers plenty of storage. Inside, you'll love the bonus room with a wet bar, perfect for entertaining, along with the convenience of indoor laundry

    Agent Photo

    Cindy Minnick

    Sun Resales, Inc.

    (863) 509-1380

    488 Putter Cir, Winter Haven, FL 33881
  • /18

    $2,119 Per Month

    • 3 Beds
    • 2 Baths
    • 2,136 Sq Ft
    • House for Rent

    443 Sandestin Dr SE, Winter Haven, FL 33884

    This home is professionally managed by Tricon, dedicated to creating exceptional rental experiences. Featuring 3 bedrooms, 2.0 bathrooms, and approximately 2,136 square feet, this well-maintained home offers a high standard of rental living, supported by a team that puts residents first. As a Tricon resident, you'll enjoy access to Tricon Vantage — a program designed to support your rental

    (863) 341-0086

    443 Sandestin Dr SE, Winter Haven, FL 33884
  • /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 $307,000

    Lennar Peace Creek Reserve - Serenity

    3060 Captain Jax Way, Winter Haven, FL 33884
    • /24

      Est $281,099

      Not Listed For Sale

      184 Fall Glo Rd, Winter Haven, FL 33880

      • 4 Beds
      • 2 Baths
      • 1,867 Sq Ft
      • Built 2018
      184 Fall Glo Rd, Winter Haven, FL 33880

      Last Sold Summary

      • 206 Days On Market

  • /41

    $350,000

    $45K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,336 Sq Ft

    262 Santa Rosa Dr, Winter Haven, FL 33884

    Spacious 2,336 SF pool home in the gated, tranquil Overlook Estates. This 4BR/2BA floorplan features a split-bedroom layout and generous living space including an eat-in kitchen, 17x18 vaulted family room, 10x16 dining room with bay window, and a large foyer. The master suite includes a dressing alcove and walk-in closet; an adjacent bedroom makes an ideal office or nursery. High-traffic areas

    Agent Photo

    Amy Reynolds

    LOCKHART & ASSOCIATES INC

    (863) 328-6637

    262 Santa Rosa Dr, Winter Haven, FL 33884
  • /16

    $1,250 Per Month

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

    1059 Spirit Lake Rd, Winter Haven, FL 33880

    This 900 SqFt unit offers comfort and convenience in a desirable location.- Electric range, microwave, and refrigerator included - Forced air heating and central cooling for year-round comfort - Tile flooring and ceiling fan(s)- Dryer included for ease of laundry - Fenced yard and patio for outdoor enjoyment - On-street parking available Perfectly situated

    (659) 207-5228

    1059 Spirit Lake Rd, Winter Haven, FL 33880
  • /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 $258,031

    Last Listing Agent Glen Barron C BUDDY JOHNSON REALTY, LLC

    2021 Oliver Place, Winter Haven, FL 33881
    • /24

      Est $318,047

      Not Listed For Sale

      2899 Eagle Nest View Dr, Winter Haven, FL 33881

      • 4 Beds
      • 2 Baths
      • 2,090 Sq Ft
      • Built 2011
      2899 Eagle Nest View Dr, Winter Haven, FL 33881

      Last Sold Summary

      • 2 Days On Market

  • /45

    $159,000

    $21K PRICE DROP
    • 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) 766-2276

    194 Fairway Cir, Winter Haven, FL 33881
  • /17

    $2,091

    Total Monthly Price

    • 2 Beds
    • 2 Baths
    • 1,636 Sq Ft
    • Condo for Rent

    1630 17th St NW Unit SI ID1545923P, Winter Haven, FL 33881

    The advertised rate of $2,091/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 7, 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

    (863) 328-4815

    1630 17th St NW Unit SI ID1545923P, 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
    • /52

      Est $319,527

      Not Listed For Sale

      208 Fall Glo Rd, Winter Haven, FL 33880

      • 4 Beds
      • 3 Baths
      • 2,526 Sq Ft
      • Built 2018
      208 Fall Glo Rd, Winter Haven, FL 33880

      Last Sold Summary

      • 68 Days On Market

Showing Results 121 - 160, Page 4 of 18

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