48,064

Winter Haven, FL Homes

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  • /16

    $460,675 Pending

    • 4 Beds
    • 3 Baths
    • 2,551 Sq Ft

    1731 Upland Ln, Winter Haven, FL 33884

    Welcome to Ashton Covey in Winter Haven! Discover the ultimate Florida lifestyle in this stunning community. Perfectly situated just off US Highway 27, your new home offers seamless access to work, outdoor recreation, shopping, dining, and more. Imagine being less than 15 minutes from Downtown Winter Haven, where charming local shops and restaurants await your exploration. Plus, you're just 5

    Agent Photo

    William Maltbie

    MALTBIE REALTY GROUP

    (863) 656-0535

    1731 Upland Ln, Winter Haven, FL 33884
  • /23

    $1,750 per month

    • 3 Beds
    • 2 Baths
    • 1,672 Sq Ft
    • House for Rent

    432 Honey Bell Rd, Winter Haven, FL 33880

    Welcome to this spacious and modern 3-bedroom, 2-bathroom home offering 1,690 sq. ft. of heated living space, built in 2019. Located in a peaceful and convenient Winter Haven community, this property features a bright open layout, newer construction finishes, and plenty of room to enjoy comfortable everyday living. Pets Allowed!!To apply for this property or to schedule your showing today,

    432 Honey Bell Rd, Winter Haven, FL 33880
  • /2

    $340,000 Sold May 30, 2025

    5043 Abigail Dr, Winter Haven, FL 33859

    • 4 Beds
    • 2 Baths
    • 1,598 Sq Ft
    • Built 2025

    Last Sold Summary

    • 4% Below List Price
    • $213/SF
    • 3 Days On Market

    Last Listing Agent Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

    5043 Abigail Dr, Winter Haven, FL 33859
    • /25

      Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,512 Sq Ft

      3000 Thornhill Rd, Winter Haven, FL 33880

      3000 Thornhill Rd, Winter Haven, FL 33880
  • /17

    $385,890 Pending

    • 4 Beds
    • 2 Baths
    • 2,551 Sq Ft

    1529 Ashton Covey Blvd, Winter Haven, FL 33884

    Under Construction. Pre-permitted lot. Welcome to Ashton Covey in Winter Haven! Discover the ultimate Florida lifestyle in this stunning community. Perfectly situated just off US Highway 27, your new home offers seamless access to work, outdoor recreation, shopping, dining, and more. Imagine being less than 15 minutes from Downtown Winter Haven, where charming local shops and restaurants await

    Agent Photo

    William Maltbie

    MALTBIE REALTY GROUP

    (863) 219-0522

    1529 Ashton Covey Blvd, Winter Haven, FL 33884
  • /9

    $1,750 per month

    • 3 Beds
    • 2 Baths
    • 1,161 Sq Ft
    • House for Rent

    1829 Nicaragua Way, Winter Haven, FL 33881

    FOR LEASE Available January 1st 2026. Located in a 55 and older community offering housing for older adults in Winter Haven Florida. This fully furnished three bedroom two bathroom home is set in a quiet and established neighborhood and provides 1,161 square feet of comfortable living space. The split floor plan enhances privacy for residents and guests while the bright bonus Florida room offers

    Jason Prieto LPT REALTY, LLC

    1829 Nicaragua Way, Winter Haven, FL 33881
  • /2

    $299,999 Sold Apr 24, 2025

    1536 Hummingbird Rd, Winter Haven, FL 33884

    • 4 Beds
    • 2.5 Baths
    • 1,794 Sq Ft
    • Built 2024

    Last Sold Summary

    • 9% Below List Price
    • $167/SF
    • 255 Days On Market

    Current Estimated Value $304,200

    Last Listing Agent Dale Human CASA FRESCA REALTY

    1536 Hummingbird Rd, Winter Haven, FL 33884
    • /44

      Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,782 Sq Ft

      318 Thornhill Estates Ct, Winter Haven, FL 33880

      318 Thornhill Estates Ct, Winter Haven, FL 33880
  • /22

    $384,990 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,797 Sq Ft

    1905 Quail Fields Cir, Winter Haven, FL 33884

    Pre-Construction. To be built. Welcome to Ashton Covey in Winter Haven! Discover the ultimate Florida lifestyle in this stunning community. Perfectly situated just off US Highway 27, your new home offers seamless access to work, outdoor recreation, shopping, dining, and more. Imagine being less than 15 minutes from Downtown Winter Haven, where charming local shops and restaurants await your

    Agent Photo

    William Maltbie

    MALTBIE REALTY GROUP

    (863) 349-3986

    1905 Quail Fields Cir, Winter Haven, FL 33884
  • /16

    $1,829 per month

    • 3 Beds
    • 2 Baths
    • 1,690 Sq Ft
    • House for Rent

    4262 Roberta Dr, Winter Haven, FL 33881

    Coming soon - this home is currently being enjoyed by another resident but will be available soon. Pre-lease this home now with Tricon Pre-Lease Guarantee. This home is professionally managed by Tricon, dedicated to creating exceptional rental experiences. Featuring 3 bedrooms, 2.0 bathrooms, and approximately 1,690 square feet, this well-maintained home offers a high standard of rental living,

    4262 Roberta Dr, Winter Haven, FL 33881
  • /2

    $1,150,000 Sold May 14, 2025

    108 Campbell Dr, Winter Haven, FL 33884

    • 4 Beds
    • 4.5 Baths
    • 5,861 Sq Ft
    • Built 1998

    Last Sold Summary

    • 23% Below List Price
    • $196/SF
    • 230 Days On Market

    Current Estimated Value $1,198,032

    Last Listing Agent Michael Stone THE STONES REAL ESTATE FIRM

    108 Campbell Dr, Winter Haven, FL 33884
    • /37

      Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,314 Sq Ft

      503 Village Cir SW, Winter Haven, FL 33880

      503 Village Cir SW, Winter Haven, FL 33880
  • /48

    $279,466 Open Sat 1PM - 5PM

    • 4 Beds
    • 2 Baths
    • 1,598 Sq Ft

    5002 Abigail Dr, Winter Haven, FL 33859

    One or more photo(s) has been virtually staged. Under Construction. Welcome home to the Bradley, one of Dream Finders Homes’ most popular floor plans, offering 4 bedrooms, 2 baths, and 1,625 square feet of thoughtful design. Set on a beautiful homesite with no rear neighbors and a serene conservation view, this brand-new home combines privacy with comfort. The open layout showcases a spacious

    Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

    5002 Abigail Dr, Winter Haven, FL 33859
  • /35

    $1,850 per month

    • 4 Beds
    • 2 Baths
    • 1,851 Sq Ft
    • House for Rent

    2164 Rose Blvd, Winter Haven, FL 33881

    Welcome Home! Glide into your beautifully maintained 4-bedroom, 2-bathroom home in the peaceful Buckeye Ridge community of Winter Haven, Florida. Built in 2018, this 1,851-square-foot home offers a spacious open-concept layout with a stylish kitchen featuring dark brown cabinetry, a central island with an integrated sink, and seamless flow into the living and dining areas. Add your favorite

    Jason Hamilton THE REALTY MEDICS

    2164 Rose Blvd, Winter Haven, FL 33881
  • /2

    $525,000 Sold Sep 04, 2025

    6112 Pebble Beach Blvd, Winter Haven, FL 33884

    • 3 Beds
    • 2 Baths
    • 2,535 Sq Ft
    • Built 2019

    Last Sold Summary

    • 3% Below List Price
    • $207/SF
    • 9 Days On Market

    Current Estimated Value $522,260

    Last Listing Agent Lori Raath LAKE ASHTON REALTY INC.

    6112 Pebble Beach Blvd, Winter Haven, FL 33884
    • /4

      Est $44,301 Not Listed For Sale

      231 Avenue U NW, Winter Haven, FL 33881

      231 Avenue U NW, Winter Haven, FL 33881
  • /33

    $382,990 New Construction

    • 5 Beds
    • 3 Baths
    • 2,077 Sq Ft

    LAKESIDE Plan at Harmony at Lake Eloise, Winter Haven, FL 33880

    Welcome to the Lakeside, one of our one-story floorplans featured in our Harmony at Lake Eloise community in Winter Haven, Florida. Take your pick between two artfully designed exteriors. Inside this beautiful 5 bedroom, 3 bathroom home, you'll find 2,077 square feet of comfortable living. The living area is an open concept, where your kitchen, living, and dining areas blend seamlessly into a

    D.R. Horton Builder
    1651 Hummingbird Rd Unit 36202793, Winter Haven, FL 33880
  • /16

    $1,805 per month

    • 3 Beds
    • 2 Baths
    • 1,303 Sq Ft
    • House for Rent

    2768 Whispering Trails Dr, Winter Haven, FL 33884

    Special offer: Pay just $500 of your base rent (taxes and fees not included) as your security deposit, valid for new applicants who sign a 12-month lease by December 31, 2025. Offer is contingent on application approval and execution of a lease agreement. Other terms and conditions may apply. This property is professionally managed by AMH, a leading single-family rental company. We work to

    2768 Whispering Trails Dr, Winter Haven, FL 33884
  • /2

    $341,967 Sold May 28, 2025

    1405 Leamington Ln, Winter Haven, FL 33884

    • 4 Beds
    • 2.5 Baths
    • 2,405 Sq Ft
    • Built 2024

    Last Sold Summary

    • 7% Below List Price
    • $142/SF
    • 309 Days On Market

    Current Estimated Value $325,893

    Last Listing Agent Delana Bender LPT REALTY, LLC

    1405 Leamington Ln, Winter Haven, FL 33884
    • /2

      Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,012 Sq Ft

      6459 Hollyberry Ln NE, Winter Haven, FL 33881

      6459 Hollyberry Ln NE, Winter Haven, FL 33881
  • /21

    $299,999 Pending

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

    5528 Taverna Way, Winter Haven, FL 33884

    One or more photo(s) has been virtually staged. Under Construction. BELOW MARKET INTEREST RATES with use of Seller's Preferred Lender. The Turquesa is the ultimate family haven, a two-story home featuring 4 bedrooms, 2.5 bathrooms and a private 2-car garage. This home offers an open concept living space designed for both relaxation and entertainment. The half bathroom off the foyer ensures every

    Dale Human CASA FRESCA REALTY

    5528 Taverna Way, Winter Haven, FL 33884
  • /22

    $1,950 per month

    • 4 Beds
    • 2 Baths
    • 1,828 Sq Ft
    • House for Rent

    2016 Carnostie Rd, Winter Haven, FL 33884

    Beautiful 2022 built home with 4 bedroom, 2 bathroom home for rent in Winter Haven. Villa Mar Community features a community pool, and playground. Property features a large open floor plan with Island kitchen, microwave, range, dishwasher, and refrigerator. Inside laundry room with washer and dryer hook-ups. 2 car garage and Covered patio. Property is 2 miles from Lego Land and in close proximity

    Debbie Browning FLORIDA REALTY RESULTS LLC

    2016 Carnostie Rd, Winter Haven, FL 33884
  • /2

    $365,000 Sold Oct 17, 2025

    236 Golf Aire Blvd, Winter Haven, FL 33884

    • 3 Beds
    • 2.5 Baths
    • 2,523 Sq Ft
    • Built 2000

    Last Sold Summary

    • 15% Below List Price
    • $145/SF
    • 27 Days On Market

    Last Listing Agent Amanda Harrison HARRISON REAL PROPERTY GROUP

    236 Golf Aire Blvd, Winter Haven, FL 33884
    • /34

      Est $320,552 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,190 Sq Ft

      868 Buccaneer Blvd, Winter Haven, FL 33880

      868 Buccaneer Blvd, Winter Haven, FL 33880
  • /23

    $304,990 New Construction

    • 3 Beds
    • 2 Baths
    • 1,615 Sq Ft

    Magenta Plan at VillaMar, Winter Haven, FL 33884

    Feel at home with the Magenta, a single-story home with 3 bedrooms, 2 bathrooms, and a 2-car garage. This layout is a true gem, seamlessly blending modern comfort with Florida charm. Open concept living dazzles with luxury vinyl plank flooring throughout the main living areas. The kitchen, featuring quartz countertops, new stainless-steel appliances and ample storage overlooks the dining and

    Casa Fresca Homes Builder
    6614 Crescent Loop Unit 36787202, Winter Haven, FL 33884
  • /20

    $2,515 per month

    • 5 Beds
    • 3 Baths
    • 2,387 Sq Ft
    • House for Rent

    4878 St James Ln, Winter Haven, FL 33881

    Special offer: Pay just $500 of your base rent (taxes and fees not included) as your security deposit, valid for new applicants who sign a 12-month lease by December 31, 2025. Offer is contingent on application approval and execution of a lease agreement. Other terms and conditions may apply. This home, constructed in 2017, is located in the St James Crossing community. This property is

    4878 St James Ln, Winter Haven, FL 33881
  • /2

    $205,000 Sold May 28, 2025

    3421 Grenville Dr, Winter Haven, FL 33884

    • 2 Beds
    • 2 Baths
    • 1,275 Sq Ft
    • Built 2006

    Last Sold Summary

    • 14% Below List Price
    • $161/SF
    • 124 Days On Market

    Current Estimated Value $215,387

    Last Listing Agent Eileen Belanger CENTURY 21 MYERS REALTY LAKE WALES

    3421 Grenville Dr, Winter Haven, FL 33884
    • /28

      Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,075 Sq Ft

      Unlisted Address

      Unlisted Address
  • /26

    $399,990 New Construction

    • 5 Beds
    • 3 Baths
    • 2,892 Sq Ft

    Catalina Plan at VillaMar, Winter Haven, FL 33884

    Never run out of space with the Catalina, a spacious two-story home designed for ultimate comfort and flexibility! This home boasts 5 bedrooms, 3 bathrooms, a versatile den, a generous upstairs recreation space and a private 2-car garage. The open concept floorplan, perfect for entertaining or just hanging out, is complemented by stylish luxury vinyl plank flooring. The kitchen and throughout the

    Casa Fresca Homes Builder
    6614 Crescent Loop Unit 36787352, Winter Haven, FL 33884
  • /16

    $2,400 per month

    • 4 Beds
    • 2 Baths
    • 1,867 Sq Ft
    • House for Rent

    3029 Country Club Cir, Winter Haven, FL 33881

    Welcome to this beautifully maintained 4-bedroom, 2-bathroom home, perfectly situated in the heart of Winter Haven. Enjoy unbeatable convenience—just 5 minutes from Hwy 27, as well as nearby schools, shopping, and local conveniences.This property offers an open and comfortable layout with generous living spaces, ideal for families or anyone seeking extra room. The home sits on a fully fenced,

    Yamil Castro Hernandez LA ROSA REALTY ORLANDO LLC

    3029 Country Club Cir, Winter Haven, FL 33881
  • /2

    $360,990 Sold May 27, 2025

    2567 Sage Valley Way, Winter Haven, FL 33884

    • 5 Beds
    • 3 Baths
    • 2,447 Sq Ft
    • Built 2024

    Last Sold Summary

    • 9% Below List Price
    • $148/SF
    • 195 Days On Market

    Current Estimated Value $361,728

    Last Listing Agent Paul King DR HORTON REALTY OF CENTRAL FLORIDA LLC

    2567 Sage Valley Way, Winter Haven, FL 33884
    • /24

      Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,485 Sq Ft

      6328 Grove Pointe Dr SE, Winter Haven, FL 33884

      6328 Grove Pointe Dr SE, Winter Haven, FL 33884
  • 1651 Hummingbird Rd Unit 36202788, Winter Haven, FL 33880

    $287,990 New Construction

    • 4 Beds
    • 2 Baths
    • 1,720 Sq Ft

    BALDWIN Plan at Harmony at Lake Eloise, Winter Haven, FL 33880

    Welcome to the Baldwin, a stunning four-bedroom, two-bathroom home located in the heart of Winter Haven, Florida at our Harmony at Lake Eloise community. As you enter the foyer to this beautiful designed home, you are greeted by with an open concept living space featuring luxury vinyl flooring throughout. The kitchen overlooks the dining and living room, while having a view to the oversized

    D.R. Horton Builder
    1651 Hummingbird Rd Unit 36202788, Winter Haven, FL 33880
  • /17

    $2,199 per month

    • 3 Beds
    • 2 Baths
    • 2,035 Sq Ft
    • House for Rent

    1599 Lemon Ave, Winter Haven, FL 33881

    Coming soon - this home is currently being enjoyed by another resident but will be available soon. Pre-lease this home now with Tricon Pre-Lease Guarantee. This home is professionally managed by Tricon, dedicated to creating exceptional rental experiences. Featuring 3 bedrooms, 2.0 bathrooms, and approximately 2,035 square feet, this well-maintained home offers a high standard of rental living,

    1599 Lemon Ave, Winter Haven, FL 33881
  • /2

    $125,000 Sold Aug 06, 2025

    4918 Rosewood St, Winter Haven, FL 33880

    • 2 Beds
    • 2 Baths
    • 1,008 Sq Ft
    • Built 1980

    Last Sold Summary

    • 6% Below List Price
    • $124/SF
    • 96 Days On Market

    Last Listing Agent Kathy Devor COLDWELL BANKER REALTY

    4918 Rosewood St, Winter Haven, FL 33880
    • /90

      Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,144 Sq Ft

      6319 Grove Pointe Dr SE, Winter Haven, FL 33884

      6319 Grove Pointe Dr SE, Winter Haven, FL 33884
  • /43

    $689,900 Pending

    • 4 Beds
    • 3 Baths
    • 2,481 Sq Ft

    7358 Bent Grass Dr, Winter Haven, FL 33884

    Under contract-accepting backup offers. LAKEFRONT POOL HOME WITH A DOCK IN A GATED COMMUNITY. NEW ROOF 2023-NEW LVP flooring 2023-NEW paint inside & out 2023- Pool resurfaced & painted 2023. Enjoy spectacular lake views right from the living room and primary bedroom. Designer kitchen with Samsung stainless appliances, gas range, granite countertops, tiled back splash, breakfast bar and Kraft-maid

    David Lambert REDFIN CORPORATION

    7358 Bent Grass Dr, Winter Haven, FL 33884
  • /15

    $2,000 per month

    • 3 Beds
    • 2 Baths
    • 1,875 Sq Ft
    • House for Rent

    417 Greenfield Rd, Winter Haven, FL 33884

    Beautiful home in gated Cyrpresswood neighborhood, close to Legoland, Hospitals, US 27 and I 4, golf community with multiple courses in the neighborhood. Fresh paint on the house. Great place to live with clubhouse, and restaurant in neighborhood, community pool, no need to leave the neighborhood. Nice and ample 3bed/2bath with Florida room Come see today before is gone!

    Roberto Rodriguez EXP REALTY LLC

    417 Greenfield Rd, Winter Haven, FL 33884
  • /13

    $215,000 Sold Mar 07, 2025

    64 Coleman Rd, Winter Haven, FL 33880

    • 3 Beds
    • 2 Baths
    • 1,074 Sq Ft
    • Built 1980

    Last Sold Summary

    • 14% Below List Price
    • $200/SF
    • 126 Days On Market

    Current Estimated Value $213,057

    Last Listing Agent Freddy Alvarado HOMETRUST REALTY GROUP

    64 Coleman Rd, Winter Haven, FL 33880
    • /33

      Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,456 Sq Ft

      6132 Grand Oaks Dr SE, Winter Haven, FL 33884

      6132 Grand Oaks Dr SE, Winter Haven, FL 33884

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