Winter Haven, FL Homes for Sale under $400,000

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  $249,000

  $10K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,526 Sq Ft

  4454 Glenns Landing, Winter Haven, FL 33884

  One or more photo(s) has been virtually staged. PRICE IMPROVEMENT with a $10,000 drop! Get your appointment to see this beautifully maintained 2-bedroom, 2-bath home with a 2-car garage offers the perfect blend of comfort, smart updates, and lifestyle perks. There’s something about 4454 Glenns Landing that feels like home before you even step inside. Maybe it’s the quiet charm of the neighborhood

  Tisha Talbot CENTURY 21 MYERS REALTY

  4454 Glenns Landing, Winter Haven, FL 33884
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  $125,000

  $30K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,680 Sq Ft

  115 Pineapple Dr, Winter Haven, FL 33884

  SELLERS OFFERING $5,000 TOWARD FIRST YEAR'S LOT RENT OR TO HELP WITH CLOSING COSTS. Welcome home to your new waterfront 2 Bedroom, 2 bath, separate den/bonus room home. Located in the active 55+ Orange Manor East Community. Spend quality time with friends and family in your new living room/kitchen open floor plan. Kitchen offers all modern appliances and you can enjoy a view of the beautiful lake

  Darlene Bice

  115 Pineapple Dr, Winter Haven, FL 33884
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  /16

  $314,900

  • 4 Beds
  • 2 Baths
  • 1,851 Sq Ft

  996 Summer Glen Dr, Winter Haven, FL 33880

  Come and see this move-in ready four-bedroom, two-bathroom home in the lovely Coventry Cove neighborhood. This home features a spacious open floor plan that seamlessly connects the living spaces for a highly functional and airy feel. The updated kitchen boasts beautiful granite countertops and stainless steel appliances, keeping the chef of the family engaged with the rest of the home. A

  Robert Salmons ENTERA REALTY LLC

  996 Summer Glen Dr, Winter Haven, FL 33880
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  $292,000

  $2K PRICE INCREASE

  • 3 Beds
  • 2 Baths
  • 1,919 Sq Ft

  123 Ruby Lake Dr, Winter Haven, FL 33884

  APPROVED SHORT SALE. THIS BEAUTIFUL HOME IS A 3 BEDROOM TWO BATH HOME WITH AN OFFICE. CAN BE USED AS A 4TH BEDROOM. LARGE OVERSIZED LOT IN A GATED COMMUNITY.

  Lisa Gonzalez Signature Realty Group

  123 Ruby Lake Dr, Winter Haven, FL 33884
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  $349,900

  Open Sat 2PM - 4PM

  • 3 Beds
  • 3 Baths
  • 1,892 Sq Ft

  6 Golfview Cir NE, Winter Haven, FL 33881

  Location is Key! NO HOA! New Roof, New AC, 3 New Bathrooms, New Front Door, New Floors etc. Next to Polk State College, Lake Elbert Walking Path, Boat Launch and only 2 miles from Downtown Winter Haven. Fresh paint inside and out. The West side of the house has its own access if you want to use the 3rd bedroom as a mother-in-law suite or rent it out privately. The house access is through the

  Keith St. Onge LA ROSA REALTY PRESTIGE

  6 Golfview Cir NE, Winter Haven, FL 33881
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  $118,000

  • 2 Beds
  • 2 Baths
  • 1,030 Sq Ft

  333 Lake Howard Dr NW Unit 203C, Winter Haven, FL 33880

  Enjoy a relaxed, maintenance-free lifestyle in this well-loved 55+ condo overlooking the beautifully maintained grounds of Imperial Harbours and the shores of Lake Howard. From both the bedroom and enclosed Florida room, take in peaceful views of the community pool and landscaped courtyard—an ideal backdrop for quiet mornings or unwinding at the end of the day. Located in Building Two, this

  Debbie Grogan COLDWELL BANKER REALTY

  333 Lake Howard Dr NW Unit 203C, Winter Haven, FL 33880
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  $374,900

  • 5 Beds
  • 3.5 Baths
  • 3,200 Sq Ft

  1015 Corso Dr, Winter Haven, FL 33884

  Like new 5-bedroom, 3.5-bath home with a functional open layout and abundant natural light. The kitchen overlooks the main living area, making it perfect for entertaining. Upstairs, a versatile loft adds valuable extra living space. With generously sized secondary bedrooms, modern finishes, and a 2-car garage, this home is ready for its next owner. Easy to show!

  William Figueroa SOVEREIGN REAL ESTATE GROUP

  1015 Corso Dr, Winter Haven, FL 33884
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  $275,000

  $5K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,375 Sq Ft

  94 Lake Daisy Blvd, Winter Haven, FL 33884

  Welcome to this charming three-bedroom, two-bath home nestled in the desirable Lake Daisy Wood neighborhood. Featuring a practical open concept floor plan with tile throughout, this residence is designed for comfortable living. The inviting living room seamlessly connects to a screened porch lanai through sliding glass doors, providing a perfect view of the spacious, fenced backyard—ideal for

  David Small KELLER WILLIAMS REALTY SMART 1

  94 Lake Daisy Blvd, Winter Haven, FL 33884
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  /13

  $390,000

  $12K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,242 Sq Ft

  Unlisted Address

  Short Sale. Over a half-acre fenced in lot with a 4 bedroom 2 1/2 bath home with an office or den. Large family room with a separate formal dining room. Eat in kitchen with 2 pantry's. New roof in 2017-2018 and a new air conditioner in 2019. Great location minutesfrom State Road 60 and close to all the dining and theme parks and spring baseball field in Winter Haven.

  Erica W Ranson BROOKS REALTY GROUP LLC

  Unlisted Address
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  $285,000

  • 2 Beds
  • 2.5 Baths
  • 2,045 Sq Ft

  21 Casarena Ct, Winter Haven, FL 33881

  Move in ready and located on the Winter Haven Chain of Lakes! Welcome to the gated community of Casarena on the Lakes. This well-designed and meticulously maintained home is set up just right for indoor and outdoor living. The first floor is an open design with the fireplace separating the living and dining area. Enjoy granite countertops and updated appliances in the spacious kitchen that

  Kami Rickert HOMETRUST REAL ESTATE & PTY MGT

  21 Casarena Ct, Winter Haven, FL 33881
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  $169,500

  • 2 Beds
  • 2 Baths
  • 1,080 Sq Ft

  6081 Southern Oaks Dr SE, Winter Haven, FL 33884

  Welcome to 6081 Southern Oaks Drive SE, a beautifully maintained manufactured home in the highly sought after 55+ community of Garden Grove Oaks where you OWN your Land and enjoy low HOA fees in a peaceful, well-maintained neighborhood. This home features two generously sized bedrooms and two full bathrooms. The primary suite boasts an extra-large walk in closet and private en-suite bath. Step

  Anita Lowe LOCKHART & ASSOCIATES INC

  6081 Southern Oaks Dr SE, Winter Haven, FL 33884
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  /2

  $150,000

  • Land
  • 13,939 Sq Ft
  • $468,750 per Acre

  1776 Lake Hill Dr, Winter Haven, FL 33884

  Large residential lot that will accommodate a variety of floor plans. Builder and building plans must be approved by Owner.

  John Wood, JR JOHN WOOD REALTY, INC.

  1776 Lake Hill Dr, Winter Haven, FL 33884
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  /16

  $214,900

  $5K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,220 Sq Ft

  1581 Oakview Cir SE, Winter Haven, FL 33880

  Welcome to a move-in ready villa in the desirable 55+ Oakview community of Winter Haven—now strategically repositioned to reflect today’s market and create immediate opportunity. This well-maintained 2-bedroom, 2-bath home offers 1,220 sq ft of comfortable living with a functional open layout, spacious bedrooms with walk-in closets, and a screened lanai designed for relaxed Florida mornings and

  Vanessa Aybar Badillo LPT REALTY, LLC

  1581 Oakview Cir SE, Winter Haven, FL 33880
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  /2

  $175,000

  • Land
  • 13,068 Sq Ft
  • $583,333 per Acre

  0 N Lake Shipp Dr, Winter Haven, FL 33880

  GREAT OPPORTUNITY FOR A LAKEFRONT LOT ON BEAUTIFUL LAKE SHIPP. THIS IS PART OF THE EXPANSIVE WINTER HAVEN CHAIN OF LAKES. BUILD YOUR DREAM HOME - THE POSSIBILITIES ARE ENDLESS. MOST OF THE LOT HAS ALREADY BEEN CLEARED! UTILITIES ARE NEARBY AND EASILY CONNECTED IN. THIS LOCATION IS IDEAL FOR EASY ACCESS TO THE POLK PARKWAY, THE NEW ORLANDO REGIONAL HOSPITAL, AND I-4.

  Rob Dee, PA CHARLES RUTENBERG REALTY INC

  0 N Lake Shipp Dr, Winter Haven, FL 33880
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  $278,900

  $26K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,325 Sq Ft

  2285 Avenue C SW, Winter Haven, FL 33880

  Super Motivated Seller!! Discover this charming 4 bedroom, 2 bathroom single family home located in the heart of Winter Haven, just minutes from the serene shores of Lake Howard. With its spacious layout and versatile design, this property is perfect for families and savvy investors alike. It has a separate mother in law suite, offering privacy or the potential for rental income. A recently

  Miluska Parot LPT REALTY, LLC

  2285 Avenue C SW, Winter Haven, FL 33880
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  $247,900

  • 2 Beds
  • 2 Baths
  • 1,385 Sq Ft

  2865 Attwater Loop, Winter Haven, FL 33884

  Traditions at Lake Ruby is a resort-style 55+community with a lovely clubhouse, lake access, gated, and loads of activitiesThis stunning , freshly painted inside-unit villa has everything that you have been waiting for! The St Lucia is a popular open floorplan featuring 2 bedrooms, 2 bathrooms and a den/office Highly upgraded wood plank porcelain tile floors can be found throughout the living

  Madri Spoelstra DREAM REALTY GROUP

  2865 Attwater Loop, Winter Haven, FL 33884
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  $269,999

  $5K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,719 Sq Ft

  4019 Carteret Dr, Winter Haven, FL 33884

  One or more photo(s) has been virtually staged. Welcome to this beautifully maintained residence located in the lakefront community of Traditions, one of Winter Haven’s premier 55+ gated communities known for its vibrant lifestyle & exceptional amenities. Fully upgraded with a brand new HVAC system and water heater installed (both in March 2026), an updated roof (November 2023), updated kitchen

  Patricia de Graaff RE/MAX HERITAGE PROFESSIONALS

  4019 Carteret Dr, Winter Haven, FL 33884
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  $337,000

  $17K PRICE INCREASE

  • 3 Beds
  • 2 Baths
  • 1,586 Sq Ft

  688 Augusta Rd, Winter Haven, FL 33884

  Welcome to this meticulously maintained 3-bedroom, 2-bath pool home located in the highly sought-after 24-hour guard-gated Cypresswood Golf and Country Club community of Winter Haven. Thoughtfully designed with a desirable split-bedroom floorplan, this residence offers both privacy and functionality for everyday living and entertaining. Plus, seller is currently in the process of installing a NEW

  Kayly Malinas JOHN WOOD REALTY, INC.

  688 Augusta Rd, Winter Haven, FL 33884
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  /2

  $135,000

  • 3 Beds
  • 1 Bath
  • 1,016 Sq Ft

  1513 32nd St NW, Winter Haven, FL 33881

  Great investment.

  Renee Butler BROKERS REALTY OF CENTRAL FLOR

  1513 32nd St NW, Winter Haven, FL 33881
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  $315,000

  Open Sun 1PM - 4PM $15K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,856 Sq Ft

  961 Drexel Ave NE, Winter Haven, FL 33881

  ***PRICE DECREASE +++ SELLER IS OFFERING $5000 in seller concessions!!! This unique 2-story home in Winter Haven is full of character and charm, located just three houses down from scenic Lake Elbert. Thoughtfully updated while preserving its warm, rustic appeal, this property offers a welcoming atmosphere from the moment you arrive. Outdoor enthusiasts will love the 2.4-mile paved loop trail

  Lisa Ford KELLER WILLIAMS REALTY SMART

  961 Drexel Ave NE, Winter Haven, FL 33881

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