49,155

Winter Haven, FL Homes

Section Image Section Image Section Image
  • /39

    $44,000

    $21K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,056 Sq Ft

    369 Putter Cir, Winter Haven, FL 33881

    This 2-bedroom, 2-bathroom home offers a perfect place for relaxation plus lots of room for activities. Enjoy the convenience of an inside laundry and unwind in your private screened room at the back of the home. The central A/C was upgraded to "mini splits" in 2028 & 2019 in the living room, the Florida room and both of the bedrooms. The windows were replaced in 2018. There is a

    Agent Photo

    Cindy Minnick

    Sun Resales, Inc.

    369 Putter Cir, Winter Haven, FL 33881
  • /16

    $1,735 Per Month

    • 4 Beds
    • 2 Baths
    • 1,304 Sq Ft
    • House for Rent

    1916 Wallace Manor Dr, Winter Haven, FL 33880

    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. Rent this home by September 30, 2026 and receive $500 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

    1916 Wallace Manor Dr, Winter Haven, FL 33880
  • /2

    $125,000

    Sold Jul 29, 2026

    5850 Cypress Gardens Blvd Unit 302, Winter Haven, FL 33884

    • 2 Beds
    • 1.5 Baths
    • 1,332 Sq Ft
    • Built 1975

    Last Sold Summary

    • 16% Below List Price
    • $94/SF
    • 94 Days On Market

    Current Estimated Value $133,211

    Last Listing Agent Vince Reina HAVEN REALTY & INVESTMENTS

    5850 Cypress Gardens Blvd Unit 302, Winter Haven, FL 33884
    • /56

      Est $265,237

      Not Listed For Sale

      6130 Grey Heron Dr, Winter Haven, FL 33881

      • 3 Beds
      • 2 Baths
      • 1,698 Sq Ft
      • Built 2017
      6130 Grey Heron Dr, Winter Haven, FL 33881

      Last Sold Summary

      • 75 Days On Market

      Last Listing Agent Jamar Brown SELL & BUY HOMES REALTY INC

  • /22

    $69,000

    • 2 Beds
    • 2 Baths
    • 938 Sq Ft

    508 Century Dr, Winter Haven, FL 33881

    Rare gem, gorgeous 2 bedroom 2 bath, 1989 Homes of Merit, on beautiful golf course with a pond view. Renovated home with over 1400 sf, laminate flooring (2022) throughout, both bathrooms (2020), updated kitchen including granite counter tops (2018), screened patio (2021), windows surround the enclosed Fl room with mini split system to enjoy the golf course view and some of Florida's wildlife

    Agent Photo

    Cindy Minnick

    Sun Resales, Inc.

    508 Century Dr, Winter Haven, FL 33881
  • /13

    $2,450 Per Month

    • 5 Beds
    • 2.5 Baths
    • 2,215 Sq Ft
    • House for Rent

    950 Cattleman St, Winter Haven, FL 33881

    Property Id: 2850871 Stunning 5-Bedroom, 2.5-Bath Corner Lot Home - FULLY FENCED YARD, WOOD DECK & PERGOLA! Welcome to 950 Cattleman Street, a beautiful two-story home located on a premium corner lot in the desirable Inman Groves community in Winter Haven, FL. Built in 2023, this spacious 2,215 sq ft property offers modern interior living combined with an incredible outdoor setup!

    950 Cattleman St, Winter Haven, FL 33881
  • /2

    $395,000

    Sold Aug 14, 2026

    419 Pinellas Rd, Winter Haven, FL 33884

    • 4 Beds
    • 2.5 Baths
    • 2,248 Sq Ft
    • Built 1974

    Last Sold Summary

    • 1% Below List Price
    • $176/SF
    • 25 Days On Market

    Current Estimated Value $391,510

    Last Listing Agent Mika Rotunda HEART OF FLORIDA REALTY LLC

    419 Pinellas Rd, Winter Haven, FL 33884
    • /16

      Est $217,174

      Not Listed For Sale

      108 4th St NE, Winter Haven, FL 33881

      • 3 Beds
      • 2 Baths
      • 1,344 Sq Ft
      • Built 2023
      108 4th St NE, Winter Haven, FL 33881

      Last Sold Summary

      • 80 Days On Market

      Last Listing Agent Melissa Witter KELLER WILLIAMS REALTY SMART 1

  • /32

    $1,200,000

    • 3 Beds
    • 2 Baths
    • 2,129 Sq Ft

    4401 Chambliss Rd, Winter Haven, FL 33884

    Welcome to your slice of heaven in Winter Haven! Situated on just over 6.5 acres you will find this charming 3/2/2 Cassidy custom pool home surrounded by green meadows and mature oak trees. 4401 Chambliss Rd. offers space, freedom, and a lifestyle you simply won’t find inside typical neighborhoods. This expansive homestead provides room for horses, chickens, gardens, equipment, and future

    Agent Photo

    Cyleste Goodson

    FLORIDA REAL ESTATE COMPANY

    4401 Chambliss Rd, Winter Haven, FL 33884
  • /15

    $2,000 Per Month

    • 3 Beds
    • 2 Baths
    • 1,567 Sq Ft
    • House for Rent

    4736 Mandolin Loop, Winter Haven, FL 33884

    Apply now or schedule your self-tour today and take the first step toward getting more than just a place to live. Rent with FirstKey Homes for a home that's right for you, plus professional service and maintenance, innovative resident programs, and more; that's the power of purple!This 3-bedroom, 2-bathroom rental home in Winter Haven, FL, might be the perfect fit for your lifestyle. See

    4736 Mandolin Loop, Winter Haven, FL 33884
  • /2

    $154,000

    Sold Feb 26, 2026

    205 Winter Ridge Blvd Unit 3, Winter Haven, FL 33881

    • 3 Beds
    • 2 Baths
    • 1,073 Sq Ft
    • Built 1992

    Last Sold Summary

    • 4% Below List Price
    • $144/SF
    • 6 Days On Market

    Current Estimated Value $152,587

    Last Listing Agent Renee Butler BROKERS REALTY OF CENTRAL FLOR

    205 Winter Ridge Blvd Unit 3, Winter Haven, FL 33881
    • /2

      Not Listed For Sale

      208 Maple St, Winter Haven, FL 33880

      208 Maple St, Winter Haven, FL 33880

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Mabel Vega Negron LA ROSA REALTY CW PROPERTIES L

  • /49

    $189,900

    $29K PRICE DROP Pending
    • 2 Beds
    • 2 Baths
    • 1,257 Sq Ft

    1502 Buckeye Rd NE Unit 4, Winter Haven, FL 33881

    Virtually Staged. A rare opportunity to own one of only six cluster homes positioned along the peaceful shoreline of Lake Buckeye! A charming open courtyard entry welcomes you to the front door, creating a private and inviting approach that sets this home apart. Inside, the living room immediately draws your eye outdoors, featuring double French doors that open to an enclosed lanai and extended

    Agent Photo

    CarLee Marchetti

    STAR REALTY OF WINTER HAVEN

    1502 Buckeye Rd NE Unit 4, Winter Haven, FL 33881
  • /16

    $1,769 Per Month

    • 3 Beds
    • 2 Baths
    • 1,340 Sq Ft
    • House for Rent

    3111 Buckeye Point Dr, Winter Haven, FL 33881

    This home is professionally managed by Tricon, dedicated to creating exceptional rental experiences. Featuring 3 bedrooms, 2.0 bathrooms, and approximately 1,340 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

    3111 Buckeye Point Dr, Winter Haven, FL 33881
  • /16

    $279,304

    Sold Oct 08, 2025

    2126 Chris Dr, Winter Haven, FL 33884

    • 3 Beds
    • 2 Baths
    • 1,487 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • $188/SF
    • 8 Days On Market

    Current Estimated Value $277,455

    Lennar Peace Creek Reserve - Estate Key Collection

    2126 Chris Dr, Winter Haven, FL 33884
    • /2

      Not Listed For Sale

      30 Flamingo Blvd, Winter Haven, FL 33880

      • 3 Beds
      • 2 Baths
      • 960 Sq Ft
      • Built 1976
      30 Flamingo Blvd, Winter Haven, FL 33880

      Last Sold Summary

      • 28 Days On Market

      Last Listing Agent Ashley Parkinson KELLER WILLIAMS REALTY SMART 1

  • /32

    $399,999

    $20K PRICE DROP
    • 5 Beds
    • 4 Baths
    • 3,040 Sq Ft

    205 Tifton St, Winter Haven, FL 33880

    Honey, stop the car! This home truly has it all. Featuring 5 bedrooms, 4 full baths, a spacious loft, and a 3-car garage, this property offers room for everyone.Your 68,132 sq. ft. homesite (1.56 acres) is a little piece of heaven—flat, open space with no rear neighbor, perfect for privacy and endless possibilities.Inside, you’ll find an entertainer’s paradise: a double oven, a kitchen

    Agent Photo

    Paul Shearn

    FUTURE HOME REALTY INC

    205 Tifton St, Winter Haven, FL 33880
  • /14

    $1,149 Per Month

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

    3072 St Paul Dr, Winter Haven, FL 33880

    Property Id: 1107 This pleasant 2 bed, 1 bath apartment with a convenient location has 3 great neighbors in a 4 plex. There is parking for two cars in front of apartment. Apartment has a refrigerator and stove, with laundry hook ups for washer and dryer. Come see 3072 St. Paul Drive Winter Haven, 33880. Walking distance to CVS Pharmacy, Mid Florida Credit Union Bank, RedBox, Subway,

    3072 St Paul Dr, Winter Haven, FL 33880
  • /2

    $369,900

    Sold Feb 11, 2026

    7044 Summit Cir, Winter Haven, FL 33884

    • 4 Beds
    • 2 Baths
    • 2,113 Sq Ft
    • Built 2005

    Last Sold Summary

    • $175/SF
    • 6 Days On Market

    Current Estimated Value $372,315

    Last Listing Agent Arturo Matamoros EXP REALTY LLC

    7044 Summit Cir, Winter Haven, FL 33884
    • /43

      Not Listed For Sale

      235 6th St NW Unit 207, Winter Haven, FL 33881

      • 2 Beds
      • 2 Baths
      • 857 Sq Ft
      • Built 1982
      235 6th St NW Unit 207, Winter Haven, FL 33881

      Last Sold Summary

      • 97 Days On Market

      Last Listing Agent April Spaulding LPT REALTY, LLC

  • /63

    $54,990

    $3K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,380 Sq Ft

    104 Rigi Slope Dr, Winter Haven, FL 33881

    Discover retirement retreat in Swiss Village, a 55+ community nestled on Lake Henry. This maintained Palm Harbor manufactured home offers comfortable living with 2 bedrooms and 2 bathrooms, plus bonus spaces that make it truly special. Step inside to find updated polywood flooring throughout, replacing carpet in 2022 when subfloors were also reinforced with 3/4" plywood. Enjoy an enclosed front

    Agent Photo

    Chrissy Walter

    Sunset Home Sales

    104 Rigi Slope Dr, Winter Haven, FL 33881
  • /16

    $1,900 Per Month

    • 4 Beds
    • 2 Baths
    • 2,284 Sq Ft
    • House for Rent

    557 Reddicks Cir, Winter Haven, FL 33884

    EXCITING NEWS: WE RECENTLY RENOVATED THIS HOME! IMPROVEMENTS INCLUDE: NEW HARD SURFACE COUNTERTOPS. APPLY TODAY OR ASK YOUR LEASING SPECIALIST FOR MORE DETAILS! Apply now or schedule your self-tour today and take the first step toward getting more than just a place to live. Rent with FirstKey Homes for a home that's right for you, plus professional service and

    557 Reddicks Cir, Winter Haven, FL 33884
  • /2

    $300,000

    Sold Apr 13, 2026

    561 Cody Caleb Dr, Winter Haven, FL 33884

    • 4 Beds
    • 2.5 Baths
    • 2,773 Sq Ft
    • Built 2006

    Last Sold Summary

    • 3% Below List Price
    • $108/SF
    • 61 Days On Market

    Current Estimated Value $306,008

    Last Listing Agent Lesley Guarino CITRAVEST MANAGEMENT LLC

    561 Cody Caleb Dr, Winter Haven, FL 33884
    • /2

      Est $280,065

      Not Listed For Sale

      441 Squires Grove Dr, Winter Haven, FL 33880

      • 4 Beds
      • 2 Baths
      • 1,846 Sq Ft
      • Built 2018
      441 Squires Grove Dr, Winter Haven, FL 33880

      Last Sold Summary

      • 50 Days On Market

      Last Listing Agent Blanca Pagan CHARLES RUTENBERG REALTY ORLANDO

  • /56

    $44,990

    • 2 Beds
    • 2 Baths

    293 Alpine Dr, Winter Haven, FL 33881

    Discover your retreat in the heart of Central Florida! This **2-bedroom, 2-bathroom** furnished manufactured home is nestled within **Swiss Village**, an active **55+ retirement community** on beautiful **Lake Henry**. Move in with ease - this home comes furnished minus just a few personal items, so you can start enjoying the Florida lifestyle right away. Recent upgrades bring peace of mind,

    Agent Photo

    Chrissy Walter

    Sunset Home Sales

    293 Alpine Dr, Winter Haven, FL 33881
  • /2

    $1,595 Per Month

    • 3 Beds
    • 1 Bath
    • 1,296 Sq Ft
    • House for Rent

    876 Crestwood Dr, Winter Haven, FL 33881

    This home located in a quiet and desirable area of Winter Haven. This well-maintained property offers a comfortable layout with plenty of natural light, creating a warm and inviting living space. The home features spacious bedrooms, a cozy living area, and a functional kitchen with ample cabinet space, perfect for everyday living. The property also includes a nice outdoor area, ideal for

    876 Crestwood Dr, Winter Haven, FL 33881
  • /2

    $290,000

    Sold Nov 26, 2025

    1480 Leamington Ln, Winter Haven, FL 33884

    • 4 Beds
    • 2.5 Baths
    • 2,202 Sq Ft
    • Built 2024

    Last Sold Summary

    • 17% Below List Price
    • $132/SF
    • 402 Days On Market

    Current Estimated Value $302,267

    Last Listing Agent Claudia Gutierrez ADAMS HOMES REALTY

    1480 Leamington Ln, Winter Haven, FL 33884
    • /20

      Not Listed For Sale

      3000 Thornhill Rd, Winter Haven, FL 33880

      • 3 Beds
      • 2 Baths
      • 1,512 Sq Ft
      • Built 1999
      3000 Thornhill Rd, Winter Haven, FL 33880

      Last Sold Summary

      • 78 Days On Market

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

  • /45

    $425,000

    $40K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,663 Sq Ft

    148 Lake Otis Rd, Winter Haven, FL 33884

    HUGE PRICE REDUCTION! SELLER VERY MOTIVATED! 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,

    Agent Photo

    Michelle Armbruster

    LOCKHART & ASSOCIATES INC

    148 Lake Otis Rd, Winter Haven, FL 33884
  • /18

    $1,740 Per Month

    • 4 Beds
    • 3 Baths
    • 2,576 Sq Ft
    • House for Rent

    3637 Queens Cove Blvd, Winter Haven, FL 33880

    EXCITING NEWS: WE RECENTLY RENOVATED THIS HOME! IMPROVEMENTS INCLUDE: NEW STAINLESS STEEL APPLIANCES. Apply now or schedule your self-tour today and take the first step toward getting more than just a place to live. Rent with FirstKey Homes for a home that's right for you, plus professional service and maintenance, innovative resident programs, and more; that's the power of

    3637 Queens Cove Blvd, Winter Haven, FL 33880
  • /16

    $289,490

    Sold Jul 14, 2026

    6212 Botticella Blvd, Winter Haven, FL 33884

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

    Move in Ready Sold Summary

    • $137/SF
    • 74 Days On Market

    Current Estimated Value $289,455

    Lennar Villa Mar

    6212 Botticella Blvd, Winter Haven, FL 33884
    • /2

      Not Listed For Sale

      6459 Hollyberry Ln NE, Winter Haven, FL 33881

      • 2 Beds
      • 2 Baths
      • 1,012 Sq Ft
      • Built 1987
      6459 Hollyberry Ln NE, Winter Haven, FL 33881

      Last Sold Summary

      • 120 Days On Market

      Last Listing Agent Larry Hilton REMAX EXPERTS

  • /32

    $379,900

    • 5 Beds
    • 3 Baths
    • 2,696 Sq Ft

    204 Inman Blvd, Winter Haven, FL 33881

    Welcome home to this beautifully maintained 5-bedroom, 3-bath residence offering nearly 2,700 square feet of flexible living space in one of Winter Haven's fastest-growing areas. Priced at just $379,900, this spacious home delivers exceptional value with room for everyone.Designed with today's lifestyles in mind, the thoughtfully crafted floor plan includes five true bedrooms, three full

    Agent Photo

    Veronica Bard

    LA ROSA REALTY PRESTIGE

    204 Inman Blvd, Winter Haven, FL 33881
  • /15

    $1,855 Per Month

    • 4 Beds
    • 2 Baths
    • 1,938 Sq Ft
    • House for Rent

    178 Andreas St, Winter Haven, FL 33881

    Apply now or schedule your self-tour today and take the first step toward getting more than just a place to live. Rent with FirstKey Homes for a home that's right for you, plus professional service and maintenance, innovative resident programs, and more; that's the power of purple!This 4-bedroom, 2-bathroom rental home in Winter Haven, FL, has a lot to offer; does it check all your boxes?

    178 Andreas St, Winter Haven, FL 33881
  • /16

    $269,990

    Sold Apr 02, 2026

    6448 Domizio Dr, Winter Haven, FL 33884

    • 4 Beds
    • 2 Baths
    • 1,874 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • 13% Below List Price
    • $144/SF
    • 60 Days On Market

    Lennar Villa Mar

    6448 Domizio Dr, Winter Haven, FL 33884
    • /2

      Not Listed For Sale

      6470 Peppertree Path NE, Winter Haven, FL 33881

      • 2 Beds
      • 2 Baths
      • 1,135 Sq Ft
      • Built 1984
      6470 Peppertree Path NE, Winter Haven, FL 33881

      Last Sold Summary

      • 39 Days On Market

      Last Listing Agent Don Cleveland COLDWELL BANKER REALTY

  • /38

    $49,990

    $5K PRICE DROP
    • 2 Beds
    • 2 Baths

    75 Bern Dr, Winter Haven, FL 33881

    **Your Central Florida retreat awaits.** This 2-bedroom, 2-bathroom manufactured home in Swiss Village - a 55+ active adult community - delivers comfort, convenience, and a lifestyle most only dream about. Inside, you'll find a freshly painted interior that feels bright and inviting from the moment you walk through the door. A powerful 3-ton A/C unit installed in 2023 keeps every room cool during

    Agent Photo

    Chrissy Walter

    Sunset Home Sales

    75 Bern Dr, Winter Haven, FL 33881
  • /19

    $1,759 Per Month

    • 3 Beds
    • 2 Baths
    • 1,630 Sq Ft
    • House for Rent

    495 Majestic Gardens Blvd, Winter Haven, FL 33880

    This home is professionally managed by Tricon, dedicated to creating exceptional rental experiences. Featuring 3 bedrooms, 2.0 bathrooms, and approximately 1,630 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

    495 Majestic Gardens Blvd, Winter Haven, FL 33880
  • /2

    $325,000

    Sold May 27, 2026

    569 Reggie Rd, Winter Haven, FL 33884

    • 4 Beds
    • 2.5 Baths
    • 1,933 Sq Ft
    • Built 2024

    Last Sold Summary

    • 2% Above List Price
    • $168/SF
    • 9 Days On Market

    Current Estimated Value $322,678

    Last Listing Agent John Hubbert, Jr BHHS FLORIDA PROPERTIES GROUP

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

      Est $309,693

      Not Listed For Sale

      2505 Salzburg Loop, Winter Haven, FL 33884

      • 2 Beds
      • 2 Baths
      • 2,062 Sq Ft
      • Built 2015
      2505 Salzburg Loop, Winter Haven, FL 33884

      Last Sold Summary

      • 335 Days On Market

      Last Listing Agent David Shippey XCELLENCE

Showing Results 201 - 240, Page 6 of 18

How to Buy a Home How to Finance a Home How to Sell a Home