49,349

Winter Haven, FL Homes

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  • /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
  • /18

    $1,720 Per Month

    • 3 Beds
    • 2 Baths
    • 1,407 Sq Ft
    • House for Rent

    163 Southern Breeze Lp, Winter Haven, FL 33880

    From Hwy 17 S - Turn right onto Spirit Lake Rd and continue for 1.6 miles. Turn left onto Grady Polk Rd and destination will be on the right. From Hwy 17 N - Turn left onto Spirit Lake Rd and continue for 1.6 miles. Turn left onto Grady Polk Rd and destination will be on the right. Welcome to South Haven, Winter Haven's newest build-to-rent community where luxury and convenience come together

    163 Southern Breeze Lp, Winter Haven, FL 33880
  • /17

    $305,900

    Sold Jul 07, 2026

    2527 Sage Valley Way, Winter Haven, FL 33884

    • 3 Beds
    • 2 Baths
    • 1,672 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • 5% Below List Price
    • $183/SF
    • 19 Days On Market

    Current Estimated Value $276,667

    D.R. Horton Harmony at Lake Eloise

    2527 Sage Valley Way, Winter Haven, FL 33884
    • /2

      Est $263,456

      Not Listed For Sale

      5732 Lakeside Landings Blvd, Winter Haven, FL 33881

      • 4 Beds
      • 2 Baths
      • 1,748 Sq Ft
      • Built 2018
      5732 Lakeside Landings Blvd, Winter Haven, FL 33881

      Last Sold Summary

      • 55 Days On Market

  • /52

    $325,000

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,730 Sq Ft

    1209 Lake Loop, Winter Haven, FL 33880

    Under contract-accepting backup offers. Welcome to this beautifully remodeled 3-bedroom, 2-bathroom residence situated on a generous lot of nearly one-third of an acre. Offering an abundance of flexible living space, the interior features fresh neutral paint, brand-new porcelain tile flooring, and fully upgraded finishes throughout. The updated kitchen is equipped with granite countertops,

    Agent Photo

    Daniel Robinson

    HOUWZER INC

    1209 Lake Loop, Winter Haven, FL 33880
  • /16

    $2,430 Per Month

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

    557 Reddicks Cir, Winter Haven, FL 33884

    EXCITING NEWS: WE ARE CURRENTLY RENOVATING THIS HOME! NOTE THAT THE PHOTOS SHOWN REPRESENT THE HOME BEFORE RENOVATION AND DO NOT REFLECT ANY UPDATES. PLANNED 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

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

    $290,000

    Sold Mar 19, 2026

    2005 Spirit Lake Rd, Winter Haven, FL 33880

    • 3 Beds
    • 2 Baths
    • 1,710 Sq Ft
    • Built 1987

    Last Sold Summary

    • 6% Below List Price
    • $170/SF
    • 25 Days On Market

    Current Estimated Value $290,913

    Last Listing Agent Becky Sigler VINTAGE REAL ESTATE SERVICES

    2005 Spirit Lake Rd, Winter Haven, FL 33880
    • /34

      Est $279,363

      Not Listed For Sale

      3034 Royal Tern Dr, Winter Haven, FL 33881

      • 4 Beds
      • 2 Baths
      • 1,851 Sq Ft
      • Built 2018
      3034 Royal Tern Dr, Winter Haven, FL 33881

      Last Sold Summary

      • 6 Days On Market

  • /46

    $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
  • /15

    $2,390 Per Month

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

    3637 Queens Cove Blvd, Winter Haven, FL 33880

    EXCITING NEWS: WE ARE CURRENTLY RENOVATING THIS HOME! NOTE THAT THE PHOTOS SHOWN REPRESENT THE HOME BEFORE RENOVATION AND DO NOT REFLECT ANY UPDATES. PLANNED IMPROVEMENTS INCLUDE: NEW STAINLESS-STEEL APPLIANCES. 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

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

    $294,490

    Sold Jul 22, 2026

    6245 Botticella Blvd, Winter Haven, FL 33884

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

    Move in Ready Sold Summary

    • $139/SF
    • 4 Days On Market

    Lennar Villa Mar

    6245 Botticella Blvd, Winter Haven, FL 33884
    • /17

      Est $216,786

      Not Listed For Sale

      3004 Caneel St, Winter Haven, FL 33884

      • 2 Beds
      • 2 Baths
      • 1,521 Sq Ft
      • Built 2018
      3004 Caneel St, Winter Haven, FL 33884

      Last Sold Summary

      • 47 Days On Market

  • /60

    $40,000

    $15K 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
  • /16

    $1,870 Per Month

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft
    • House for Rent

    110 7th Jpv St, Winter Haven, FL 33880

    Please note, our homes are available on a first-come, first-serve basis and are not reserved until the holding fee agreement is signed and the holding fee is paid by the primary applicant.Coming soon! This home is currently being enjoyed by another resident but will be available soon. Please respect their privacy and do not disturb. You can complete the application process and reserve

    110 7th Jpv St, Winter Haven, FL 33880
  • /14

    $317,000

    Sold Sep 23, 2025

    3845 Giorgio Dr, Winter Haven, FL 33884

    • 4 Beds
    • 2.5 Baths
    • 2,168 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • $146/SF
    • 265 Days On Market

    Current Estimated Value $328,443

    Meritage Homes VillaMar - Classic Series

    3845 Giorgio Dr, Winter Haven, FL 33884
    • /17

      Est $438,752

      Not Listed For Sale

      5764 E County Road 542, Winter Haven, FL 33880

      • 6 Beds
      • 3 Baths
      • 2,592 Sq Ft
      • Built 1980
      5764 E County Road 542, Winter Haven, FL 33880

      Last Sold Summary

      • 41 Days On Market

  • /51

    $49,990

    Pending
    • 2 Beds
    • 2 Baths
    • 1,248 Sq Ft

    145 Zermatt Dr, Winter Haven, FL 33881

    Tucked away on Zermatt Drive, this 2-bedroom, 2-bathroom manufactured home offers 1,248 square feet of living in the heart of Swiss Village. Mostly furnished and ready for its next chapter, it pairs thoughtful updates with everyday ease-simply ask the listing agent which pieces stay and which the seller will take. Major systems have been carefully tended to. The roof dates to 2023, the HVAC to

    Agent Photo

    Chrissy Walter

    Sunset Home Sales

    145 Zermatt Dr, Winter Haven, FL 33881
  • /15

    $1,949 Per Month

    • 3 Beds
    • 2 Baths
    • 1,432 Sq Ft
    • House for Rent

    2065 Whispering Trails Blvd, Winter Haven, FL 33884

    Welcome to your future home in beautiful Winter Haven, Florida! This charming property is conveniently located near an array of delightful restaurants and department stores, making it an ideal spot for both leisure and shopping.Key property features include a spacious layout thoughtfully designed for comfort. Enjoy the benefits of central heating and cooling, alongside air conditioning

    2065 Whispering Trails Blvd, Winter Haven, FL 33884
  • /30

    $279,519

    Sold Apr 22, 2026

    272 Meredith Blvd, Winter Haven, FL 33881

    • 4 Beds
    • 2 Baths
    • 1,625 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • $172/SF
    • 9 Days On Market

    Current Estimated Value $272,276

    Dream Finders Homes Willowbrook North

    272 Meredith Blvd, Winter Haven, FL 33881
    • /2

      Est $318,617

      Not Listed For Sale

      543 Squires Grove Dr, Winter Haven, FL 33880

      • 4 Beds
      • 3 Baths
      • 2,526 Sq Ft
      • Built 2018
      543 Squires Grove Dr, Winter Haven, FL 33880

      Last Sold Summary

      • 135 Days On Market

  • /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
  • /17

    $2,466

    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 $2,466/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 1, 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

    1630 17th St NW Unit SI ID1545923P, Winter Haven, FL 33881
  • /2

    $299,999

    Sold Apr 03, 2026

    5528 Taverna Way, Winter Haven, FL 33884

    • 4 Beds
    • 2.5 Baths
    • 2,039 Sq Ft
    • Built 2025

    Last Sold Summary

    • 12% Below List Price
    • $147/SF
    • 173 Days On Market

    Current Estimated Value $300,400

    Last Listing Agent Dale Human CASA FRESCA REALTY

    5528 Taverna Way, Winter Haven, FL 33884
    • /2

      Est $285,575

      Not Listed For Sale

      548 Lucerne Blvd, Winter Haven, FL 33881

      • 4 Beds
      • 2.5 Baths
      • 1,956 Sq Ft
      • Built 2018
      548 Lucerne Blvd, Winter Haven, FL 33881

      Last Sold Summary

      • 154 Days On Market

  • /38

    $80,000

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

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

    Under contract-accepting backup offers. 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

    Agent Photo

    Amy Reynolds

    LOCKHART & ASSOCIATES INC

    333 Lake Howard Dr NW Unit 304B, Winter Haven, FL 33880
  • /12

    $1,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,366 Sq Ft
    • Condo for Rent

    400 El Camino Dr Unit 203, Winter Haven, FL 33884

    Property Id: 2712857 ***55+ Senior Community*** Amazing 2 bedroom, 2 bathroom apartment in Winter Haven. Amenities included: balcony, central air, central heat, and dishwasher. No Utilities included. Is pet friendly. Date Available: Jun 27th 2026. $1,500/month rent. $1,500 security deposit required. Please submit the form on this page or contact Oscar at to learn more. This property is

    400 El Camino Dr Unit 203, Winter Haven, FL 33884
  • /21

    $299,990

    Sold Aug 04, 2025

    3335 Twilight Rd, Winter Haven, FL 33881

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

    Move in Ready Sold Summary

    • $210/SF
    • 9 Days On Market

    Current Estimated Value $314,667

    Starlight Homes Sunset Hills

    3335 Twilight Rd, Winter Haven, FL 33881
    • /2

      Est $334,094

      Not Listed For Sale

      3021 Royal Tern Dr, Winter Haven, FL 33881

      • 5 Beds
      • 3 Baths
      • 2,616 Sq Ft
      • Built 2018
      3021 Royal Tern Dr, Winter Haven, FL 33881

      Last Sold Summary

      • 192 Days On Market

  • /23

    $259,000

    Under Contract
    • 4 Beds
    • 2 Baths
    • 1,750 Sq Ft

    3977 Warbler Dr, Winter Haven, FL 33880

    Under contract-accepting backup offers. Virtually Staged. Welcome to this updated 4-bedroom, 2-bath home offering 1,750 square feet of bright, open living space in the desirable Queens Cove community of Winter Haven. Step inside to discover vaulted ceilings, abundant natural light, and an open-concept floor plan designed for comfortable everyday living and effortless entertaining. Luxury vinyl

    Agent Photo

    Cindy Greco

    EXP REALTY LLC

    3977 Warbler Dr, Winter Haven, FL 33880
  • /20

    $3,048

    Total Monthly Price

    • 3 Beds
    • 2 Baths
    • 1,722 Sq Ft
    • Condo for Rent

    919 Ave S SE Unit SI FL1-ID1325030P, Winter Haven, FL 33880

    The advertised rate of $3,048/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 1, 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 be

    919 Ave S SE Unit SI FL1-ID1325030P, Winter Haven, FL 33880
  • /2

    $750,000

    Sold Sep 26, 2025

    328 Hamilton Shores Dr NE, Winter Haven, FL 33881

    • 5 Beds
    • 3.5 Baths
    • 3,812 Sq Ft
    • Built 2001

    Last Sold Summary

    • 2% Below List Price
    • $197/SF
    • 56 Days On Market

    Current Estimated Value $733,768

    Last Listing Agent Michael Stone THE STONES REAL ESTATE FIRM

    328 Hamilton Shores Dr NE, Winter Haven, FL 33881
    • /41

      Est $285,211

      Not Listed For Sale

      2185 Rose Blvd, Winter Haven, FL 33881

      • 4 Beds
      • 2 Baths
      • 1,851 Sq Ft
      • Built 2018
      2185 Rose Blvd, Winter Haven, FL 33881

      Last Sold Summary

      • 49 Days On Market

  • /41

    $235,000

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,727 Sq Ft

    1040 Cambridge Dr, Winter Haven, FL 33881

    Under contract-accepting backup offers. Short Sale. A beautifully maintained 3 bedroom, 2 bath home built in 2021, with 1,727 square feet of thoughtfully designed living space. Located in the desirable Lucerne Park Reserve community, this home combines modern finishes, an open layout, and everyday convenience. Step inside to discover a bright, open-concept floor plan featuring tile and luxury

    Agent Photo

    Kate Wilson

    EXP REALTY LLC

    1040 Cambridge Dr, Winter Haven, FL 33881
  • /15

    $2,030 Per Month

    • 4 Beds
    • 2 Baths
    • 1,758 Sq Ft
    • House for Rent

    112 Southern Breeze Lp, Winter Haven, FL 33880

    From Hwy 17 S - Turn right onto Spirit Lake Rd and continue for 1.6 miles. Turn left onto Grady Polk Rd and destination will be on the right. From Hwy 17 N - Turn left onto Spirit Lake Rd and continue for 1.6 miles. Turn left onto Grady Polk Rd and destination will be on the right. Apply now or schedule your self-tour today and take the first step toward getting more than

    112 Southern Breeze Lp, Winter Haven, FL 33880
  • /12

    $334,499

    Sold Feb 10, 2026

    6044 Navona Way, Winter Haven, FL 33884

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

    Move in Ready Sold Summary

    • $135/SF
    • 40 Days On Market

    Current Estimated Value $334,161

    Casa Fresca Homes Villa Mar

    6044 Navona Way, Winter Haven, FL 33884
    • /2

      Est $405,537

      Not Listed For Sale

      2973 Dayton Dr, Winter Haven, FL 33884

      • 3 Beds
      • 3 Baths
      • 2,659 Sq Ft
      • Built 2018
      2973 Dayton Dr, Winter Haven, FL 33884

      Last Sold Summary

      • 99 Days On Market

  • /46

    $280,000

    $10K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,846 Sq Ft

    1646 Tressel Ct, Winter Haven, FL 33881

    PRICE DROP!! Nestled within a secure, gated community with impressively low HOA fees, this beautiful 4-bedroom, 2-bathroom home offers true peace of mind. The highly versatile layout easily adapts to your lifestyle, whether you need extra space for a growing family, a dedicated home office, or a welcoming guest suite. Beyond the front door, you're just minutes from top-rated schools, medical

    Agent Photo

    Twanna Dewdney

    LA ROSA REALTY PRESTIGE

    1646 Tressel Ct, Winter Haven, FL 33881
  • /15

    $1,575 Per Month

    • 2 Beds
    • 2 Baths
    • 898 Sq Ft
    • Condo for Rent

    311 Ave Y NE Unit 311 Avenue Y NE Unit B, Winter Haven, FL 33881

    Property Id: 1444878 For Rent: Cozy 2-Bedroom Rent: $1,575/month Deposit: $1,575 Lawn Service is included. Lease Term: 1 year minimum Utilities: Tenant responsible for all utilities. Small Pets Only - Pet Fee $50 a Month, per pet. 2 Pet Max No Smoking Background & Credit Check Every individual aged 18 or older residing at the property and/or any

    311 Ave Y NE Unit 311 Avenue Y NE Unit B, Winter Haven, FL 33881
  • /2

    $284,000

    Sold Dec 30, 2025

    232 Spirit Landing Cir, Winter Haven, FL 33880

    • 3 Beds
    • 2 Baths
    • 1,546 Sq Ft
    • Built 2024

    Last Sold Summary

    • 2% Below List Price
    • $184/SF
    • 21 Days On Market

    Current Estimated Value $280,362

    Last Listing Agent Samuel Eckerson KELLER WILLIAMS ADVANTAGE REALTY

    232 Spirit Landing Cir, Winter Haven, FL 33880
    • /40

      Est $268,839

      Not Listed For Sale

      1436 Wallace Manor Pass, Winter Haven, FL 33880

      • 3 Beds
      • 2 Baths
      • 1,531 Sq Ft
      • Built 2014
      1436 Wallace Manor Pass, Winter Haven, FL 33880

      Last Sold Summary

      • 0 Days On Market

Showing Results 281 - 320, Page 8 of 18

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