49,346

Winter Haven, FL Homes

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  • /33

    $214,900

    $20K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,131 Sq Ft

    2026 Kings Crossing SW, Winter Haven, FL 33880

    WELCOME HOME TO STONEBRIDGE! Step through your private, custom-gated Courtyard into a beautifully updated Stonebridge Patio Home that is truly MOVE-IN-READY! NEWER ROOF (2024), NEWER ELECTRIC PANEL (2024), NEWER WINDOWS AND SLIDERS (2022), NEW GUTTERS & DOWNSPOUTS (2026). This fabulous property is located in FEMA Zone X, a low-risk flood zone. From the moment you enter, you'll be impressed by the

    Agent Photo

    Kitty Mark

    COLDWELL BANKER REALTY

    2026 Kings Crossing SW, Winter Haven, FL 33880
  • /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
  • /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 $230,692

    Last Listing Agent Chrissi Jasso ASSOCIATE REALTY

    144 Brad Cir, Winter Haven, FL 33880
    • /2

      Est $394,926

      Not Listed For Sale

      1010 Biltmore Dr NW, Winter Haven, FL 33881

      • 3 Beds
      • 2 Baths
      • 1,672 Sq Ft
      • Built 1956
      1010 Biltmore Dr NW, Winter Haven, FL 33881

      Last Sold Summary

      • 39 Days On Market

  • /52

    $54,990

    $5K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,560 Sq Ft

    158 Sago Palm Way, Winter Haven, FL 33880

    Discover retirement retreat in this charming 2-bedroom, 2-bathroom double-wide manufactured home, nestled within the sought-after Winter Haven Oaks - a gated 55+ active adult community brimming with small-town charm and Florida sunshine. Situated on a corner lot, this home features a spacious double carport, a relaxing lanai, and a bonus enclosed room with glass windows - ideal for morning coffee

    Agent Photo

    Chrissy Walter

    Sunset Home Sales

    158 Sago Palm Way, Winter Haven, FL 33880
  • /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
  • /39

    $389,557

    Sold Nov 14, 2025

    276 Meredith Blvd, Winter Haven, FL 33881

    • 4 Beds
    • 3 Baths
    • 2,110 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • $185/SF
    • 20 Days On Market

    Dream Finders Homes Willowbrook North

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

      Est $414,400

      Not Listed For Sale

      109 Lake Mariam Way, Winter Haven, FL 33884

      • 4 Beds
      • 2 Baths
      • 2,087 Sq Ft
      • Built 1995
      109 Lake Mariam Way, Winter Haven, FL 33884

      Last Sold Summary

      • 43 Days On Market

  • /38

    $265,000

    • 3 Beds
    • 2 Baths
    • 1,678 Sq Ft

    1406 Meadow Dr NE, Winter Haven, FL 33881

    Spacious Single-Story Block Home with Endless Potential! Nestled in a quiet, established neighborhood close to Polk State College with no HOA, this solid single-story block home immediately catches the eye with its charming blend of stucco and natural multi-colored stone accents. Boasting 1,678 square feet of comfortable living space (2,527 square feet total), the interior features a generously

    Agent Photo

    Twanna Dewdney

    LA ROSA REALTY PRESTIGE

    1406 Meadow Dr NE, Winter Haven, FL 33881
  • /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

    $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 $255,846

    Last Listing Agent Glen Barron C BUDDY JOHNSON REALTY, LLC

    2021 Oliver Place, Winter Haven, FL 33881
    • /2

      Est $366,480

      Not Listed For Sale

      7016 Summit Cir, Winter Haven, FL 33884

      • 3 Beds
      • 2 Baths
      • 1,888 Sq Ft
      • Built 2005
      7016 Summit Cir, Winter Haven, FL 33884

      Last Sold Summary

      • 29 Days On Market

  • /65

    $494,999

    $5K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,333 Sq Ft

    408 Talamone Dr, Winter Haven, FL 33884

    This well-maintained 4-bedroom, 3-bathroom pool home is located in the sought-after gated community of Tuscany at Winterset, offering both comfort and style in a prime setting. Inside, you’ll find an inviting layout highlighted by solid surface countertops, elegant tray ceilings, and detailed crown molding that adds a refined touch throughout the living spaces. Major updates provide peace of

    Agent Photo

    Tony Insua Jr.

    LOCKHART & ASSOCIATES INC

    408 Talamone Dr, Winter Haven, FL 33884
  • /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
  • /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
    • /2

      Est $337,929

      Not Listed For Sale

      6750 Winterset Gardens Rd, Winter Haven, FL 33884

      • 3 Beds
      • 2 Baths
      • 1,874 Sq Ft
      • Built 1972
      6750 Winterset Gardens Rd, Winter Haven, FL 33884

      Last Sold Summary

      • 291 Days On Market

  • /26

    $250,000

    $20K PRICE DROP
    • 2 Beds
    • 1.5 Baths
    • 1,527 Sq Ft

    940 Oleander Dr SE, Winter Haven, FL 33880

    Auction Property. Ranch-style home offering 2 bedrooms and 1.5 bathrooms with a spacious living room and a good-sized yard. Features include a durable metal roof, RV electrical hookups, and a chicken coop. Some updates in the kitchen. Short Sale subject to lender approval.

    Agent Photo

    David Hartigan

    JASON MITCHELL REAL ESTATE FLO

    940 Oleander Dr SE, 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

    $255,990

    Sold Jan 27, 2026

    2134 Chris Dr, Winter Haven, FL 33884

    • 5 Beds
    • 2.5 Baths
    • 2,112 Sq Ft
    • Built 2025

    Last Sold Summary

    • 18% Below List Price
    • $121/SF
    • 49 Days On Market

    Current Estimated Value $261,512

    Last Listing Agent Ben Goldstein LENNAR REALTY

    2134 Chris Dr, Winter Haven, FL 33884
    • /2

      Est $401,987

      Not Listed For Sale

      4570 Chambliss Rd, Winter Haven, FL 33884

      • 3 Beds
      • 2.5 Baths
      • 1,685 Sq Ft
      • Built 1978
      4570 Chambliss Rd, Winter Haven, FL 33884

      Last Sold Summary

      • 91 Days On Market

  • /43

    $49,990

    $5K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 960 Sq Ft

    5236 Grand Cypress Ct, Winter Haven, FL 33880

    Discover this 2-bedroom, 2-bathroom manufactured home nestled in the heart of Winter Haven Oaks, a 55+ gated community in Winter Haven, FL. This estate sale offers an incredible opportunity for a quick close - and everything in the home stays, including a golf cart ready for your next neighborhood adventure! Stay active and social with an impressive lineup of amenities, including two clubhouses,

    Agent Photo

    Chrissy Walter

    Sunset Home Sales

    5236 Grand Cypress Ct, Winter Haven, FL 33880
  • /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
  • /2

    $313,162

    Sold Oct 19, 2025

    1558 Jessica Blvd, Winter Haven, FL 33884

    • 5 Beds
    • 2.5 Baths
    • 2,326 Sq Ft
    • Built 2025

    Last Sold Summary

    • 6% Below List Price
    • $135/SF
    • 28 Days On Market

    Current Estimated Value $311,778

    Last Listing Agent Ben Goldstein LENNAR REALTY

    1558 Jessica Blvd, Winter Haven, FL 33884
    • /2

      Est $335,996

      Not Listed For Sale

      768 Canberra Rd, Winter Haven, FL 33884

      • 3 Beds
      • 2 Baths
      • 1,888 Sq Ft
      • Built 1986
      768 Canberra Rd, Winter Haven, FL 33884

      Last Sold Summary

      • 101 Days On Market

  • /15

    $240,000

    $59K PRICE DROP Under Contract
    • 3 Beds
    • 2 Baths
    • 1,732 Sq Ft

    3180 Country Club Cir, Winter Haven, FL 33881

    Under contract-accepting backup offers. Short Sale. APPROVED SHORT SALE AT PRICE! CHAPTER 7 BANKRUPTCY - Located In The Country Walk Community, This 2019 Built Home At 3180 Country Club Cir, Winter Haven, FL 33881 Features The Popular DR Horton Aria Floor Plan Offering 3 Bedrooms, 2 Bathrooms, & 1,672 Sq Ft Of Living Space. This Home Offers an Open Concept Layout With A Spacious Living Area,

    Agent Photo

    Jon McCall PA

    DALTON WADE INC

    3180 Country Club Cir, 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

    $285,000

    Sold Mar 16, 2026

    5316 Hogan Ln, Winter Haven, FL 33884

    • 2 Beds
    • 2 Baths
    • 1,339 Sq Ft
    • Built 2013

    Last Sold Summary

    • 1% Below List Price
    • $213/SF
    • 13 Days On Market

    Current Estimated Value $285,012

    Last Listing Agent Lori Raath LAKE ASHTON REALTY INC.

    5316 Hogan Ln, Winter Haven, FL 33884
    • /2

      Est $447,946

      Not Listed For Sale

      128 Lake Region Cir, Winter Haven, FL 33881

      • 3 Beds
      • 2 Baths
      • 2,188 Sq Ft
      • Built 2003
      128 Lake Region Cir, Winter Haven, FL 33881

      Last Sold Summary

      • 3 Days On Market

  • /22

    $35,000

    $13K PRICE DROP
    • 2 Beds
    • 2 Baths

    625 Century Dr, Winter Haven, FL 33881

    This 940 sq ft home offers an open floor plan and a bright Florida room at the front of the house-perfect for relaxing or morning coffee. Recent improvements include new plumbing throughout (10/2023), a newer roof (2023), and an AC system installed around 2020. The home features convenient stackable inside laundry and a large shed for extra storage. A wonderful opportunity to make this home your

    Agent Photo

    Cindy Minnick

    Sun Resales, Inc.

    625 Century Dr, Winter Haven, FL 33881
  • /15

    $1,990 Per Month

    • 3 Beds
    • 2 Baths
    • 1,645 Sq Ft
    • House for Rent

    505 Reddicks Cir, Winter Haven, FL 33884

    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

    505 Reddicks Cir, 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 $151,247

    Last Listing Agent Renee Butler BROKERS REALTY OF CENTRAL FLOR

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

      Est $259,847

      Not Listed For Sale

      42 Enclave Dr, Winter Haven, FL 33884

      • 3 Beds
      • 3 Baths
      • 2,370 Sq Ft
      • Built 1999
      42 Enclave Dr, Winter Haven, FL 33884

      Last Sold Summary

      • 133 Days On Market

  • /60

    $349,999

    $50K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,524 Sq Ft

    1522 Eckart Dr, Winter Haven, FL 33881

    This updated 3-bedroom, 2-bath home offers comfort, functionality, and plenty of outdoor space to enjoy Florida living. Inside, you’ll love the spacious open floor plan featuring a Great Room, dining area, and family room combination with cathedral ceilings, wood burning fireplace, laminate wood flooring, and abundant recessed lighting. French doors from the dining room lead to an open patio and

    Agent Photo

    Russ Rhoads

    EXP REALTY LLC

    1522 Eckart Dr, Winter Haven, FL 33881
  • /20

    $2,115

    Total Monthly Price

    • 4 Beds
    • 2 Baths
    • 1,981 Sq Ft
    • House for Rent

    4766 Osprey Way, Winter Haven, FL 33881

    Now offering 20-month leases. Sign today and lock in today’s low rate for the next 20 months! Offer valid for new applicants who sign a 20-month lease by July 31st, 2026. Base rent will remain at the 12-month lease rate for the duration of the 20-month term. Offer is contingent on application approval and execution of a lease agreement. Other terms and conditions may apply. This home, constructed

    4766 Osprey Way, Winter Haven, FL 33881
  • /61

    $65,000

    Sold Aug 22, 2025

    214 Oak Tree Blvd, Winter Haven, FL 33880

    • 2 Beds
    • 2 Baths
    • 1,128 Sq Ft
    • Built 1991

    Last Sold Summary

    • 7% Below List Price
    • $58/SF
    • 62 Days On Market

    Last Listing Agent Chrissy Walter Sunset Home Sales

    214 Oak Tree Blvd, Winter Haven, FL 33880
    • /2

      Est $297,311

      Not Listed For Sale

      633 Heather Glen Loop, Winter Haven, FL 33884

      • 3 Beds
      • 2 Baths
      • 1,731 Sq Ft
      • Built 2002
      633 Heather Glen Loop, Winter Haven, FL 33884

      Last Sold Summary

      • 17 Days On Market

  • /27

    $77,000

    • 2 Beds
    • 2 Baths

    1010 Eagle Dr, Winter Haven, FL 33881

    This well-maintained home features a membrane roof over the home, Florida room, and shed for added durability and peace of mind. Inside, you'll find newer windows and attractive vinyl flooring throughout, with tile flooring in the Florida room for easy maintenance and added charm. The renovated kitchen offers updated cabinetry, stainless steel appliances, and a reverse osmosis filtration system,

    Agent Photo

    Cindy Minnick

    Sun Resales, Inc.

    1010 Eagle Dr, Winter Haven, FL 33881
  • /16

    $2,100 Per Month

    • 4 Beds
    • 2 Baths
    • 2,088 Sq Ft
    • House for Rent

    436 Fish Hawk Dr, Winter Haven, FL 33884

    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

    436 Fish Hawk Dr, Winter Haven, FL 33884
  • /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 $281,181

    Lennar Peace Creek Reserve - Estate Key Collection

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

      Est $288,907

      Not Listed For Sale

      215 Rydalmont Rd, Winter Haven, FL 33884

      • 4 Beds
      • 2 Baths
      • 2,184 Sq Ft
      • Built 1972
      215 Rydalmont Rd, Winter Haven, FL 33884

      Last Sold Summary

      • 8 Days On Market

Showing Results 161 - 200, Page 5 of 18

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