Winter Haven, FL Homes for Sale under $500,000

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  /36

  $315,000

  • 3 Beds
  • 2 Baths
  • 1,560 Sq Ft

  287 Inman Blvd, Winter Haven, FL 33881

  Welcome to 287 Inman Blvd—where modern comfort meets effortless Florida living in the heart of Winter Haven. This beautifully maintained home truly feels like new, offering the peace of mind of recent construction with thoughtful upgrades already in place. In addition to the home’s like-new condition and thoughtful upgrades, qualified buyers may also have the rare opportunity to assume the

  Chris Loschiavo RE/MAX HERITAGE PROFESSIONALS

  287 Inman Blvd, Winter Haven, FL 33881
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  $299,000

  • 4 Beds
  • 2 Baths
  • 1,694 Sq Ft

  445 Mckenna Dr, Winter Haven, FL 33881

  One or more photo(s) has been virtually staged. Welcome to this thoughtfully designed single-story home in a growing Winter Haven community, wheremodern comfort meets everyday convenience. Positioned on a corner lot with clean curb appeal and a fullyfenced backyard, this property offers both functionality and a polished presentation from the moment youarrive. Inside, the home opens to

  Angel Pabon NEXTHOME MY WAY

  445 Mckenna Dr, Winter Haven, FL 33881
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  /59

  $299,999

  • 4 Beds
  • 2 Baths
  • 1,793 Sq Ft

  255 Haines Blvd, Winter Haven, FL 33881

  Welcome to 255 Haines Boulevard, Winter Haven, Florida! This beautifully maintained home offers the perfect blend of comfort, convenience, and Florida living. Featuring a spacious floor plan with plenty of natural light, this property is ideal for families, first-time homebuyers, or investors alike. The kitchen provides ample cabinet and counter space and flows seamlessly into the living and

  Sean Denney LAND SOUTH REALTY, LLC

  255 Haines Blvd, Winter Haven, FL 33881
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  /10

  $400,000

  $100K PRICE DROP

  • Land
  • 16,988 Sq Ft
  • $1,025,641 per Acre

  152 & 148 Avenue D SW, Winter Haven, FL 33880

  Two previously residential lots combined to make .39 Acres of land in heart of Downtown Winter Haven. The lots are leveled and ready to build. The current zoning on the property is MX within the Primary Urban Core which allows for multi-family, various commercial and mixed-use opportunities. Combined frontage on Ave D and 2nd Street with an alley off the south end of the property allowing

  Erik Polumbo POLK REALTY ADVISORS LLC

  152 & 148 Avenue D SW, Winter Haven, FL 33880
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  /56

  $469,900

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,247 Sq Ft

  247 S Lake Pansy Dr, Winter Haven, FL 33881

  OWNER FINANCING AVAILABLE ~ LAKEFRONT 3 BEDROOM / 2 BATH HOME WITH PICTURESQUE OPEN WATER VIEWS AND PRIVATE 30 FT DOCK! Located directly on Lake Pansy in the gated subdivision of Hartridge Hills, a quaint lakefront community of approximately 60 homes. NEWER ROOF 2022 and NEWER GENERAC GENERATOR 2020. Lot size is 150 X 83 ft directly on Lake Pansy. Additional lot size in records of 2.44 acres

  Kay Szinegh EXP REALTY LLC

  247 S Lake Pansy Dr, Winter Haven, FL 33881
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  /31

  $234,900

  $25K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,140 Sq Ft

  241 Grove Branch Rd, Winter Haven, FL 33880

  Charming 3-Bedroom, 2-Bathroom Home in Squires Grove – Move-In Ready! Welcome to this beautifully maintained 3-bedroom, 2-bathroom home located in the desirable Squires Grove subdivision. This move-in ready property offers modern updates and thoughtful features that make it the perfect place to call home. Step inside to find brand new commercial-grade waterproof laminate flooring throughout,

  Anthony Fridovich REMAX EXPERTS

  241 Grove Branch Rd, Winter Haven, FL 33880
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  $435,990

  New Construction

  • 5 Beds
  • 3 Baths
  • 2,490 Sq Ft

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

  Find all the space you need in our popular one-story Covington floorplan in Harmony at Lake Eloise, one of our communities in Winter Haven, Florida. This unique 5 bedroom, 3 bathroom and 3 car garage floorplan is available in 3 different modern exteriors. As you enter the foyer you are greeted with bedrooms 2 and 3 that are separated by a full bathroom complete with quartz countertops. As you

  D.R. Horton Builder

  1651 Hummingbird Rd Unit 36202782, Winter Haven, FL 33880
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  /2

  $274,900

  New Construction $3K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,302 Sq Ft

  3111 Firebrush Ln, Winter Haven, FL 33884

  Under Construction. Find everything you need in Harmony on Lake Eloise! Located just minutes from world class theme parks and attractions, Harmony on Lake Eloise is the perfect community to call home with its beautiful Florida lifestyle and amenities. This community boasts stunning home sites. You'll enjoy the sparkling local lakes practically in your backyard and the best local restaurants and

  Paul King DR HORTON REALTY OF CENTRAL FLORIDA LLC

  3111 Firebrush Ln, Winter Haven, FL 33884
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  /12

  $307,300

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,483 Sq Ft

  Everglade Plan at VillaMar - Classic Series, Winter Haven, FL 33884

  Open floor plan with a lot of flexibility. Retreat to your primary suite that is conveniently situated in the back of the home for plenty of privacy and offers a huge walk-in closet and bathroom with dual sink vanity and standalone shower.

  Meritage Homes Builder

  3745 Giorgio Dr Unit 37076781, Winter Haven, FL 33884
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  $287,950

  $8K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,725 Sq Ft

  257 Meadowbrook Blvd, Winter Haven, FL 33881

  PRICE IMPROVEMENT! Welcome to this super spacious 3-bedroom, 2-bath home located in Lucerne Park Reserve in Winter Haven. Built in 2020, this home offers a modern split floorplan that provides privacy and functionality, perfect for everyday living or entertaining. The open layout creates a bright and airy feel throughout, with generous room sizes and excellent flow. Furniture is negotiable,

  Katherine Montana - De Jesus KELLER WILLIAMS REALTY SMART 1

  257 Meadowbrook Blvd, Winter Haven, FL 33881
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  /9

  $307,300

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,483 Sq Ft

  3936 Giorgio Dr, Winter Haven, FL 33884

  Retreat to your primary suite located in the back of the home for plenty of privacy and offers a huge walk-in closet.

  Meritage Homes Builder

  3936 Giorgio Dr, Winter Haven, FL 33884
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  /18

  $217,000

  Open Sat 9AM - 7PM

  • 3 Beds
  • 2 Baths
  • 1,019 Sq Ft

  1100 Carefree Cove Dr, Winter Haven, FL 33881

  Come see 1100 Carefree Cove Dr, recently improved with a new roof, fresh exterior paint, and fresh interior paint, presenting a comprehensively refreshed presentation. Partial flooring replacement further updates the interior living spaces, while a fenced in backyard provides practical outdoor areas. This property embodies a fresh approach to comfortable living. Included 100-Day Home Warranty

  Karen Albright OPENDOOR BROKERAGE LLC

  1100 Carefree Cove Dr, Winter Haven, FL 33881
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  $275,000

  $24K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,843 Sq Ft

  441 San Jose Dr, Winter Haven, FL 33884

  Welcome to this exceptional 2-bedroom, 2-bathroom patio home nestled within the highly sought after Orchid Springs community. Positioned on an expansive double lot, this residence offers a serene & secluded wooded vista visible from the open kitchen and the generously proportioned screened patio. Noteworthy exteri9or features; Paved drive and walkways, attractive canopies and covered front porch

  Dee Norris NEXTHOME NORRIS & COMPANY REAL

  441 San Jose Dr, Winter Haven, FL 33884
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  /26

  $339,000

  $20K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,278 Sq Ft

  5764 Royal Hills Cir, Winter Haven, FL 33881

  One or more photo(s) has been virtually staged. Motivated Seller!! *Welcome to this spacious Move-in-ready 4 bedroom, 2.5 bathroom home tucked away in the heart of Royal Hills, Winter Haven. The Home has recent upgrades including freshly painted Exterior in 2025, Roof 2024. The entire upper level has been revitalized with well-maintained carpeting while the ground floor showcases ceramic tile

  Phabie Terzi Terzier MILLENNIUM REALTY CENTER LLC

  5764 Royal Hills Cir, Winter Haven, FL 33881
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  /20

  $215,000

  $15K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,134 Sq Ft

  106 Lantern Ln, Winter Haven, FL 33884

  Back on the market due to buyer financing, property previously appraised at value. Welcome to 106 Lantern Ln in Winter Haven, a comfortable and move in ready 2 bedroom 2 bathroom home with 1,134 square feet of living space. When you step inside, you are welcomed into the living room that opens nicely to the dining area and adjoining kitchen, creating a functional and inviting layout for everyday

  Quoc Huynh JADE KEY REALTY LLC

  106 Lantern Ln, Winter Haven, FL 33884
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  /21

  $300,000

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,560 Sq Ft

  715 Grove St, Winter Haven, FL 33884

  ***This home can be yours for 4.75% Interest rate on a assumable loan*** Located in the desirable Inman Grove solar community in Winter Haven, this 3 bedroom, 2 bathroom home with a fully fenced backyard offers the perfect combination of energy efficiency, modern design, and convenient Central Florida living. Built in 2023, NO CDD, LOW HOA of less than $45.00 a month, LOW ELECTRIC BILL

  Jannese Garcia NORKIS & CO REALTY

  715 Grove St, Winter Haven, FL 33884
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  /24

  $379,999

  New Construction $10K PRICE DROP

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

  5429 San Pietro Dr, 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

  5429 San Pietro Dr, Winter Haven, FL 33884
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  /36

  $379,998

  • 4 Beds
  • 3 Baths
  • 1,680 Sq Ft

  215 Kilmer Ln, Winter Haven, FL 33884

  Fully Occupied Income Property | 3 Units | $4,300/mo Gross Rent | No Vacancy | Winter HavenRare turnkey income property generating $4,300/month in gross rent — fully occupied with zero vacancy. This versatile multi-income single-family property features two interior apartments plus a separate rear cabin, each independently rented with established tenants in place.Landlord expenses are

  Elizabeth Rodriguez CAISSA REALTY INVESTMENT INC

  215 Kilmer Ln, Winter Haven, FL 33884
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  /2

  $267,900

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,544 Sq Ft

  113 Nemo Ln, Winter Haven, FL 33881

  Move-in ready, 3-bedroom, 2-story townhome with a garage for sale in Winter Haven, FL! Downstairs, enjoy an open living area with a spacious gathering room, plus a convenient powder room, a flex space, and a private covered lanai. Upstairs, relax in your private owner's suite with a walk-in wardrobe and a private en-suite bathroom including dual vanities, a decorative tiled shower, closeted

  Highland Homes Builder

  113 Nemo Ln, Winter Haven, FL 33881
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  /9

  $255,900

  $2K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,264 Sq Ft

  3723 Imperial Dr, Winter Haven, FL 33880

  Stop looking now!This well kept home is waiting just for you. A nice 3/2 with tile and laminate thorough. This home offers a beautiful back yard with a deck for a peaceful retreat for enjoyment of the lake. Schedule your showing now.

  Louis Vincent PROPERTY WAREHOUSES OF AMERICA

  3723 Imperial Dr, Winter Haven, FL 33880

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