49,148

Winter Haven, FL Homes

Section Image Section Image Section Image
  • /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
  • /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

    $280,000

    Sold May 15, 2026

    207 24th Ct SW, Winter Haven, FL 33880

    • 3 Beds
    • 2 Baths
    • 1,296 Sq Ft
    • Built 1976

    Last Sold Summary

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

    Current Estimated Value $282,767

    Last Listing Agent Melissa Mottern KELLER WILLIAMS REALTY

    207 24th Ct SW, Winter Haven, FL 33880
    • /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

  • /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
  • /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
  • /6

    $244,990

    Sold Dec 30, 2025

    235 Turtle Bay Ave, Winter Haven, FL 33881

    • 3 Beds
    • 2 Baths
    • 1,604 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • $153/SF
    • 20 Days On Market

    Current Estimated Value $244,901

    Highland Homes Harbor at Lake Henry - Townhomes

    235 Turtle Bay Ave, Winter Haven, FL 33881
    • /2

      Not Listed For Sale

      4065 Rolling Oaks Dr, Winter Haven, FL 33880

      • 2 Beds
      • 2 Baths
      • 864 Sq Ft
      • Built 1983
      4065 Rolling Oaks Dr, Winter Haven, FL 33880

      Last Sold Summary

      • 82 Days On Market

      Last Listing Agent Ann Heaton CHARLES RUTENBERG REALTY ORLANDO

  • /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
  • /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
  • /2

    $238,000

    Sold Apr 01, 2026

    1002 Spirit Lake Rd, Winter Haven, FL 33880

    • 3 Beds
    • 1.5 Baths
    • 1,111 Sq Ft
    • Built 1962

    Last Sold Summary

    • 2% Above List Price
    • $214/SF
    • 6 Days On Market

    Current Estimated Value $233,113

    Last Listing Agent Matthew Hughes CHARLES RUTENBERG REALTY ORLANDO

    1002 Spirit Lake Rd, Winter Haven, FL 33880
    • /24

      Not Listed For Sale

      6328 Grove Pointe Dr SE, Winter Haven, FL 33884

      • 2 Beds
      • 2 Baths
      • 1,485 Sq Ft
      • Built 2002
      6328 Grove Pointe Dr SE, Winter Haven, FL 33884

      Last Sold Summary

      • 64 Days On Market

      Last Listing Agent Nicole Ash BHHS FLORIDA PROPERTIES GROUP

  • /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
  • /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
  • /2

    $110,000

    Sold Aug 31, 2026

    6644 Princeton Dr NE, Winter Haven, FL 33881

    • 2 Beds
    • 2 Baths
    • 1,296 Sq Ft
    • Built 1986

    Last Sold Summary

    • 15% Below List Price
    • $85/SF
    • 193 Days On Market

    Last Listing Agent Jason Troyan LIVE FLORIDA REALTY

    6644 Princeton Dr NE, Winter Haven, FL 33881
    • /2

      Not Listed For Sale

      12 Robin Ln, Winter Haven, FL 33880

      • 2 Beds
      • 2 Baths
      • 1,056 Sq Ft
      • Built 1976
      12 Robin Ln, Winter Haven, FL 33880

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Dee Newell S & D REAL ESTATE SERVICE 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
  • /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

    $105,000

    Sold Jun 30, 2026

    2040 San Marcos Dr SE Unit 202, Winter Haven, FL 33880

    • 1 Bed
    • 1 Bath
    • 666 Sq Ft
    • Built 1985

    Last Sold Summary

    • 4% Below List Price
    • $158/SF
    • 30 Days On Market

    Last Listing Agent Robert W. Lamond LAMOND REALTY INC.

    2040 San Marcos Dr SE Unit 202, Winter Haven, FL 33880
    • /33

      Not Listed For Sale

      6132 Grand Oaks Dr SE, Winter Haven, FL 33884

      • 2 Beds
      • 2 Baths
      • 1,456 Sq Ft
      • Built 1994
      6132 Grand Oaks Dr SE, Winter Haven, FL 33884

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Michelle Armbruster LOCKHART & ASSOCIATES INC

  • /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
  • /17

    $850

    Total Monthly Price

    • 1 Bed
    • 1 Bath
    • 500 Sq Ft
    • Condo for Rent

    1131 5th St SW Unit 5 Upstairs, Winter Haven, FL 33880

    Centrally located to restaurants, Aldis, Lowe's and other shopping within walking distance. Small quiet apartments - property has security lights for safety.

    1131 5th St SW Unit 5 Upstairs, Winter Haven, FL 33880
  • /2

    $96,000

    Sold May 08, 2026

    2065 Isle Royale Ct SE Unit 141, Winter Haven, FL 33880

    • 1 Bed
    • 1 Bath
    • 648 Sq Ft
    • Built 1987

    Last Sold Summary

    • 4% Below List Price
    • $148/SF
    • 87 Days On Market

    Current Estimated Value $96,359

    Last Listing Agent Andrew Fearn BHHS FLORIDA PROPERTIES GROUP

    2065 Isle Royale Ct SE Unit 141, Winter Haven, FL 33880
    • /15

      Not Listed For Sale

      712 Byni Ridge, Winter Haven, FL 33880

      • 4 Beds
      • 2 Baths
      • 1,536 Sq Ft
      • Built 1979
      712 Byni Ridge, Winter Haven, FL 33880

      Last Sold Summary

      • 67 Days On Market

      Last Listing Agent Duy Nguyen EXP REALTY 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
  • /15

    $1,895 Per Month

    • 3 Beds
    • 2 Baths
    • 1,720 Sq Ft
    • House for Rent

    188 Black Skimmer Ln, Wahneta, FL 33880

    This modern 3-bedroom, 2-bath home offers 1,720 square feet of comfortable living in Wahneta’s serene suburban setting. Thoughtfully maintained, it features a fresh, neutral palette and clean finishes that complement wood-look laminate flooring throughout the main areas. Ceiling fans with integrated lighting enhance the open living space’s inviting ambiance. The bedrooms balance carpet and

    188 Black Skimmer Ln, Wahneta, FL 33880
  • /2

    $265,000

    Sold Oct 24, 2025

    1568 S Lake Shipp Dr, Winter Haven, FL 33880

    • 5 Beds
    • 3 Baths
    • 1,824 Sq Ft
    • Built 1955

    Last Sold Summary

    • 24% Below List Price
    • $145/SF
    • 174 Days On Market

    Current Estimated Value $245,904

    Last Listing Agent Jordan Prais 54 REALTY LLC

    1568 S Lake Shipp Dr, Winter Haven, FL 33880
    • /2

      Est $234,760

      Not Listed For Sale

      2423 3rd St NE, Winter Haven, FL 33881

      • 3 Beds
      • 2 Baths
      • 1,173 Sq Ft
      • Built 2024
      2423 3rd St NE, Winter Haven, FL 33881

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Melissa Witter KELLER WILLIAMS REALTY SMART 1

  • /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
  • /20

    $1,995 Per Month

    • 3 Beds
    • 2 Baths
    • 1,841 Sq Ft
    • House for Rent

    914 Summer Glen Dr, Winter Haven, FL 33880

    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 $2179.90. That covers your base rent, $1995.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    914 Summer Glen Dr, Winter Haven, FL 33880
  • /2

    $315,000

    Sold Jun 01, 2026

    689 Vittorio Dr, Winter Haven, FL 33884

    • 3 Beds
    • 2 Baths
    • 2,053 Sq Ft
    • Built 2021

    Last Sold Summary

    • 2% Below List Price
    • $153/SF
    • 83 Days On Market

    Current Estimated Value $313,340

    Last Listing Agent Kelly Martinez CORCORAN CONNECT LLC

    689 Vittorio Dr, Winter Haven, FL 33884
    • /2

      Est $252,418

      Not Listed For Sale

      127 Florida Dr, Winter Haven, FL 33881

      • 3 Beds
      • 2 Baths
      • 1,216 Sq Ft
      • Built 2024
      127 Florida Dr, Winter Haven, FL 33881

      Last Sold Summary

      • 17 Days On Market

      Last Listing Agent Melissa Witter KELLER WILLIAMS REALTY SMART 1

  • /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
  • /4

    $2,150 Per Month

    • 4 Beds
    • 2 Baths
    • 2,014 Sq Ft
    • House for Rent

    737 Lake Martha Dr NE, Winter Haven, FL 33881

    Property Id: 945068 Large Lake House 4 bedroom 2 bath home at waters edge has a lot of charm. There is a laundry room off the large kitchen. A large screened porch faces the lake. Spend the day relaxing under the large porch with two fans. Barbecue on and enjoy lakefront as if you are on vacation. You might spot a bald eagle flying above while fishing on the lake. •

    737 Lake Martha Dr NE, Winter Haven, FL 33881
  • /2

    $235,000

    Sold Jul 20, 2026

    1645 Avenue C NE, Winter Haven, FL 33881

    • 3 Beds
    • 2 Baths
    • 1,204 Sq Ft
    • Built 1959

    Last Sold Summary

    • 2% Above List Price
    • $195/SF
    • 102 Days On Market

    Current Estimated Value $230,611

    Last Listing Agent Cliff Glansen FLATFEE.COM

    1645 Avenue C NE, Winter Haven, FL 33881
    • /2

      Est $280,714

      Not Listed For Sale

      256 Ruby Lake Ln, Winter Haven, FL 33884

      256 Ruby Lake Ln, Winter Haven, FL 33884

      Last Sold Summary

      • 15 Days On Market

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

  • /43

    $164,800

    • 2 Beds
    • 2 Baths
    • 1,325 Sq Ft

    628 Lakeside Ranch Ln, Winter Haven, FL 33881

    Meticulously Maintained, beautiful 2/2, move-in ready home in a quiet lake-front community. Pride of Ownership shows throughout! List of Updates attached and include finished walls, Plumbing, downspouts, Heat Pump with UV Light, Newer Appliance, Washer and Dryer (inside laundry), flooring, kitchen cabinets with soft-close, built-in pantry/storage in the Dining Room to name a few. Thoughtfully

    Agent Photo

    Sanda Andrews

    GOOD COMPANY REALTY INC.

    628 Lakeside Ranch Ln, Winter Haven, FL 33881
  • /11

    $1,250 Per Month

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

    708 Vittorio Dr, Winter Haven, FL 33884

    Welcome to your new home in Winter Haven, Florida! Beautifully furnished and move-in ready 2-bedroom, 1-bathroom apartment offering comfortable and convenient living in Winter Haven. This cozy unit features a private entrance, comfortable living room, and kitchenette, making it an ideal option for those seeking a hassle-free rental. The apartment is fully furnished and includes all utilities in

    708 Vittorio Dr, Winter Haven, FL 33884
  • /2

    $179,000

    Sold Jun 26, 2026

    3015 Avenue I NW, Winter Haven, FL 33881

    • 3 Beds
    • 1 Bath
    • 1,050 Sq Ft
    • Built 1959

    Last Sold Summary

    • 10% Below List Price
    • $170/SF
    • 392 Days On Market

    Current Estimated Value $177,160

    Last Listing Agent Maritza Cruz MIRANDA LANDA REALTY GROUP LLC

    3015 Avenue I NW, Winter Haven, FL 33881
    • /32

      Est $141,889

      Not Listed For Sale

      2600 Lucerne Park Rd Unit 508, Winter Haven, FL 33881

      • 2 Beds
      • 2 Baths
      • 845 Sq Ft
      • Built 1987
      2600 Lucerne Park Rd Unit 508, Winter Haven, FL 33881

      Last Sold Summary

      • 159 Days On Market

      Last Listing Agent Eduardo Mualim IRG CORPORATION

Showing Results 241 - 280, Page 7 of 18

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