49,154

Winter Haven, FL Homes

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  • /12

    $295,000

    • 3 Beds
    • 2 Baths
    • 1,925 Sq Ft

    706 Avenue I NE, Winter Haven, FL 33881

    Own a private oasis in the heart of Winter Haven! This beautiful 3-bedroom, 2-bathroom home features 1,941 square feet of comfortable living space. It rests on an extra-large .41-acre lot. That gives you plenty of space to relax and enjoy outdoor living and gardening. The property features a large open pool for beating the Florida heat, with a pool room and screened patio. The home also features

    Agent Photo

    Steve Lockhart

    LOCKHART & ASSOCIATES INC

    706 Avenue I NE, 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

    $31,000

    Sold Apr 13, 2026

    125 5th St NE, Winter Haven, FL 33881

    • Land
    • 6,534 Sq Ft
    • $206,667 per Acre

    Last Sold Summary

    • 44% Below List Price
    • 7 Days On Market

    Last Listing Agent Milton De La Cruz LAKELAND HOMES AND REALTY, LLC

    125 5th St NE, Winter Haven, FL 33881
    • /2

      Not Listed For Sale

      6762 Brentwood Dr NE, Winter Haven, FL 33881

      • 2 Beds
      • 2 Baths
      • 1,152 Sq Ft
      • Built 1994
      6762 Brentwood Dr NE, Winter Haven, FL 33881

      Last Sold Summary

      • 231 Days On Market

      Last Listing Agent Patricia de Graaff RE/MAX HERITAGE PROFESSIONALS

  • /46

    $299,500

    $25K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,012 Sq Ft

    5638 Royal Hills St, Winter Haven, FL 33881

    WELCOME TO THIS WELL-KEPT PROPERTY WITH LOW HOA FEE. THIS IS A SPLIT PLAN FOUR BEDROOM/TWO BATH HOME. THE PROPERTY HAS A LIVING, DINING AND FAMILY ROOM. THE EAT-IN KITCHEN IS LIGHT AND BRIGHT. THERE IS AN INSIDE LAUNDRY ROOM. THE BEDROOMS ARE NICELY SIZED. VAULTED AND CATHEDRAL CEILINGS ALONG WITH NUMEROUS PLANT SHELVES ADD CHARACTER TO THIS HOME. THERE IS A SCREENED PORCH OFF THE FAMILY ROOM

    Agent Photo

    Brenda J. Quinn

    QUINN & COMPANY REALTORS, LLC

    5638 Royal Hills St, 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

    $191,000

    Sold Jul 21, 2026

    2348 Isle Royale Ct SE, Winter Haven, FL 33880

    • 2 Beds
    • 2.5 Baths
    • 1,281 Sq Ft
    • Built 1997

    Last Sold Summary

    • 15% Below List Price
    • $149/SF
    • 503 Days On Market

    Current Estimated Value $192,914

    Last Listing Agent Fatma Higdon HIGDON HOMES REALTY LLC

    2348 Isle Royale Ct SE, Winter Haven, FL 33880
    • /2

      Est $143,648

      Not Listed For Sale

      2500 21st St NW Unit 77, Winter Haven, FL 33881

      • 2 Beds
      • 2.5 Baths
      • 1,184 Sq Ft
      • Built 1976
      2500 21st St NW Unit 77, Winter Haven, FL 33881

      Last Sold Summary

      • 34 Days On Market

      Last Listing Agent Michele Elchin DALTON WADE INC

  • /37

    $435,000

    • 3 Beds
    • 2 Baths
    • 1,572 Sq Ft

    795 Crosstower Dr, Winter Haven, FL 33880

    Built in 2023 and situated on 1.59 acres, this 3 bedroom, 2 bath home offers something increasingly hard to find in Winter Haven: a newer home with land, flexibility and NO HOA. Nearly 200 feet of street visibility along Hwy 540 creates a unique opportunity for a small business owner who understands the value of exposure. Imagine the visibility your brand could capture simply by parking your

    Agent Photo

    Veronica Bard

    LA ROSA REALTY PRESTIGE

    795 Crosstower Dr, Winter Haven, FL 33880
  • /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

    $360,000

    Sold May 07, 2026

    232 College Grove Cir NE, Winter Haven, FL 33881

    • 3 Beds
    • 2 Baths
    • 2,087 Sq Ft
    • Built 1985

    Last Sold Summary

    • 3% Above List Price
    • $172/SF
    • 2 Days On Market

    Current Estimated Value $357,393

    Last Listing Agent Amy Reynolds LOCKHART & ASSOCIATES INC

    232 College Grove Cir NE, Winter Haven, FL 33881
    • /27

      Not Listed For Sale

      6339 Grove Pointe Dr SE, Winter Haven, FL 33884

      • 3 Beds
      • 2 Baths
      • 1,485 Sq Ft
      • Built 2004
      6339 Grove Pointe Dr SE, Winter Haven, FL 33884

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Malak Benbachir KELLER WILLIAMS REALTY SMART 1

  • /100

    $1,799,900

    $150K PRICE DROP
    • 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

    13 Bogey Dr, 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
  • /2

    $283,990

    Sold Apr 02, 2026

    1112 Tyler Loop, Winter Haven, FL 33884

    • 4 Beds
    • 2.5 Baths
    • 1,880 Sq Ft
    • Built 2025

    Last Sold Summary

    • $151/SF
    • 8 Days On Market

    Current Estimated Value $284,748

    Last Listing Agent Ben Goldstein LENNAR REALTY

    1112 Tyler Loop, Winter Haven, FL 33884
    • /48

      Not Listed For Sale

      4537 Redwood St, Winter Haven, FL 33880

      • 2 Beds
      • 2 Baths
      • 1,446 Sq Ft
      • Built 1984
      4537 Redwood St, Winter Haven, FL 33880

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Leslie Yokshas KELLER WILLIAMS REALTY SMART 1

  • /43

    $455,000

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

    1830 2nd St NW Unit A, Winter Haven, FL 33881

    Calling all investors and house-hackers! Welcome to 1830 2nd St NW, a fantastic multi-family investment opportunity located right in the heart of Winter Haven. This well-maintained duplex features two spacious, mirror-image units, each offering a highly desirable 3-bedroom, 1-bathroom layout perfect for maximizing rental income and attracting long-term tenants! Both units boast bright,

    Agent Photo

    John Gomez

    EXP REALTY LLC

    1830 2nd St NW Unit A, 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

    $349,000

    Sold Apr 24, 2026

    5392 Chandler Dr, Winter Haven, FL 33884

    • 4 Beds
    • 3 Baths
    • 3,034 Sq Ft
    • Built 2006

    Last Sold Summary

    • 18% Below List Price
    • $115/SF
    • 211 Days On Market

    Current Estimated Value $354,777

    Last Listing Agent Jenni Thompson KELLER WILLIAMS REALTY

    5392 Chandler Dr, Winter Haven, FL 33884
    • /42

      Not Listed For Sale

      120 Pangola Dr, Winter Haven, FL 33880

      • 3 Beds
      • 2.5 Baths
      • 1,950 Sq Ft
      • Built 1985
      120 Pangola Dr, Winter Haven, FL 33880

      Last Sold Summary

      • 12 Days On Market

      Last Listing Agent Scott Kline KLINE REAL ESTATE SERVICES

  • /60

    $35,000

    $20K PRICE DROP
    • 3 Beds
    • 2 Baths

    269 Hummingbird Ln, Winter Haven, FL 33884

    Enjoy the best of Florida living in this spacious and beautifully maintained 2-bedroom, 2-bath home located in a private community with exclusive lake access. This inviting property offers comfort, convenience, and an unbeatable location perfect for full-time residents, vacationers, or seasonal living. Ideally situated near shopping, restaurants, entertainment, and everyday conveniences, you'll

    Agent Photo

    Glenn Fogg

    FOGG MOBILE HOME SALES LLC

    269 Hummingbird Ln, Winter Haven, FL 33884
  • /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

    $245,000

    Sold Dec 08, 2025

    512 Mckenna Dr, Winter Haven, FL 33881

    • 3 Beds
    • 2 Baths
    • 1,506 Sq Ft
    • Built 2021

    Last Sold Summary

    • 6% Below List Price
    • $163/SF
    • 116 Days On Market

    Current Estimated Value $252,607

    Last Listing Agent EJ Jimenez KELLER WILLIAMS ADVANTAGE III

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

      Not Listed For Sale

      6210 Knotty Pine Dr SE, Winter Haven, FL 33884

      • 3 Beds
      • 2 Baths
      • 1,604 Sq Ft
      • Built 1995
      6210 Knotty Pine Dr SE, Winter Haven, FL 33884

      Last Sold Summary

      • 18 Days On Market

      Last Listing Agent Brenda J. Quinn QUINN & COMPANY REALTORS, LLC

  • /12

    $209,900

    • Land
    • 32,670 Sq Ft
    • $279,867 per Acre

    0 Eloise Loop Rd Unit MFRP4939471, Winter Haven, FL 33884

    OSPREY ESTATES IS A SMALL, GATED COMMUNITY LOCATED IN BEAUTIFUL SE WINTER HAVEN, FLORIDA. THE COMMUNITY HAS A TOTAL OF FOUR LOTS--THREE HAVE UPSCALE RESIDENCES AND THIS IS THE LAST ONE AVAILABLE. THE LOT IS .75 ACRE. THIS LOCATION IS CLOSE TO SHOPPING, MULTIPLE RESTAURANTS, LEGOLAND AND BOTH TAMPA AND ORLANDO. HOA REQUIRES A MINIMUM 3,500 SQ FEET OF LIVING AND A MAXIMUM 5,500 SQ FEET OF

    Agent Photo

    Brenda J. Quinn

    QUINN & COMPANY REALTORS, LLC

    0 Eloise Loop Rd Unit MFRP4939471, 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

    $299,990

    Sold Nov 24, 2025

    3239 Nightfall Rd, Winter Haven, FL 33881

    • 3 Beds
    • 3 Baths
    • 1,426 Sq Ft
    • Built 2025

    Last Sold Summary

    • $210/SF

    Current Estimated Value $300,464

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

    3239 Nightfall Rd, Winter Haven, FL 33881
    • /17

      Not Listed For Sale

      6453 Hollyberry Ln NE, Winter Haven, FL 33881

      • 2 Beds
      • 2 Baths
      • 1,144 Sq Ft
      • Built 1985
      6453 Hollyberry Ln NE, Winter Haven, FL 33881

      Last Sold Summary

      • 37 Days On Market

      Last Listing Agent Jean Murphy CENTURY 21 MYERS REALTY

  • /100

    $599,900

    • 3 Beds
    • 2 Baths
    • 2,591 Sq Ft

    5365 Hogan Ln, Winter Haven, FL 33884

    Welcome to the next exciting chapter of your life in Lake Ashton, Central Florida’s premier 55+ active-adult community, where this immaculately maintained three-bedroom, two-bath home with a den offers exceptional comfort and elegance, including a beautiful primary suite with its own relaxing sitting room and a sparkling 71⁄2' x 36' bromine pool awaiting your enjoyment. From the striking stone

    Agent Photo

    Brad Kirwan

    GLOBAL LIFESTYLE LLC

    5365 Hogan Ln, Winter Haven, FL 33884
  • /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

    $290,640

    Sold Aug 11, 2026

    533 Ituna Cir, Winter Haven, FL 33881

    • 3 Beds
    • 2 Baths
    • 1,486 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • $196/SF
    • 49 Days On Market

    Current Estimated Value $281,000

    Highland Homes Harbor at Lake Henry - Single-Family Homes

    533 Ituna Cir, Winter Haven, FL 33881
    • /8

      Not Listed For Sale

      311 Donald Ln, Winter Haven, FL 33880

      • 3 Beds
      • 2 Baths
      • 1,056 Sq Ft
      • Built 1991
      311 Donald Ln, Winter Haven, FL 33880

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Ron Denney LAND SOUTH REALTY, LLC

  • /2

    $328,999

    New Construction $1K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,226 Sq Ft

    5386 San Pietro Dr, Winter Haven, FL 33884

    5386 San Pietro Drive, Winter Haven, FL 33884

    Builder Photo

    Casa Fresca Homes

    Builder

    5386 San Pietro Dr, Winter Haven, FL 33884
  • /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
  • /12

    $354,999

    Sold Jun 02, 2026

    5389 San Pietro Dr, Winter Haven, FL 33884

    • 5 Beds
    • 3 Baths
    • 2,471 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • $144/SF
    • 32 Days On Market

    Current Estimated Value $352,199

    Casa Fresca Homes Villa Mar

    5389 San Pietro Dr, Winter Haven, FL 33884
    • /2

      Not Listed For Sale

      316 Donald Ln, Winter Haven, FL 33880

      • 3 Beds
      • 2 Baths
      • 1,248 Sq Ft
      • Built 1995
      316 Donald Ln, Winter Haven, FL 33880

      Last Sold Summary

      • 17 Days On Market

      Last Listing Agent Ron Denney LAND SOUTH REALTY, LLC

  • /38

    $80,000

    • 3 Beds
    • 2 Baths
    • 1,330 Sq Ft

    333 Lake Howard Dr NW Unit 304B, Winter Haven, FL 33880

    Top-floor condo with INCREDIBLE lake views in the desirable 55+ community of Imperial Harbours on Lake Howard! This three-bedroom, two-bath condo offers tons of potential and is ready for your personal touches and a little TLC. The kitchen features a convenient pass-through window overlooking the dining and living areas, creating an open and functional layout. The spacious primary suite includes

    Agent Photo

    Amy Reynolds

    LOCKHART & ASSOCIATES INC

    333 Lake Howard Dr NW Unit 304B, Winter Haven, FL 33880
  • /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

    $28,000

    Sold Jun 30, 2026

    839 Sears Ave NE, Winter Haven, FL 33881

    • Land
    • 4,791 Sq Ft
    • $254,545 per Acre

    Last Sold Summary

    • 38% Below List Price
    • 18 Days On Market

    Current Estimated Value $38,500

    Last Listing Agent Kalanda Scarvers SPANN & ASSOCIATES REAL ESTATE

    839 Sears Ave NE, Winter Haven, FL 33881
    • /16

      Est $138,502

      Not Listed For Sale

      2600 Lucerne Park Rd Unit 505, Winter Haven, FL 33881

      • 2 Beds
      • 2 Baths
      • 845 Sq Ft
      • Built 1985
      2600 Lucerne Park Rd Unit 505, Winter Haven, FL 33881

      Last Sold Summary

      • 215 Days On Market

      Last Listing Agent Eduardo Mualim IRG CORPORATION

Showing Results 361 - 400, Page 10 of 18

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