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

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  $399,990 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,507 Sq Ft

  Maui Plan at Willowbrook North, Winter Haven, FL 33881

  MAUI: Beautiful 2 Level, 2 Car Garage Home with Open Concept Living and 3 Bedrooms! The Maui plan is available in Coastal, Farmhouse or Traditional exterior designs.

  DRB Homes Builder

  0 Fl-544 St Unit 36849122, Winter Haven, FL 33881
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  /45

  $305,000

  • 4 Beds
  • 2 Baths
  • 1,828 Sq Ft

  4094 Great Egret Dr, Winter Haven, FL 33881

  Step into a home where every space invites you to stay and every corner is designed to create beautiful memories. This stunning, well-cared-for 4-bedroom, 2-bath single-family home is located in a quiet and peaceful area of Winter Haven, Florida, offering the perfect balance of comfort, warmth, and everyday tranquility. From the very first moment, this home welcomes you with an open, light-filled

  Gil Medina PRESTIGE LEGACY REALTY

  4094 Great Egret Dr, Winter Haven, FL 33881
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  /21

  $303,990 New Construction

  • 4 Beds
  • 2 Baths
  • 1,607 Sq Ft

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

  An open floorplan that makes entertaining easy in the open kitchen, dining, and great room that flow to the patio. The primary suite is tucked in the rear of the home offering plenty of privacy and features a spacious walk—in closet and shower.

  Meritage Homes Builder

  3745 Giorgio Dr Unit 37076778, Winter Haven, FL 33884
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  /2

  $317,740 New Construction

  • 5 Beds
  • 2 Baths
  • 1,708 Sq Ft

  2783 Adeline Ave, Winter Haven, FL 33881

  The property is located at 2783 Adeline Ave WINTER HAVEN FL 33881 priced at 317740, the square foot and stories are 1708, 1.The number of bath is 2, halfbath is 0 there are 5 bedrooms and 2 garages. For more details please, call or email.

  D.R. Horton Builder

  2783 Adeline Ave, Winter Haven, FL 33881
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  /2

  $314,990 New Construction

  • 3 Beds
  • 2 Baths
  • 1,536 Sq Ft

  3323 Twilight Rd, Winter Haven, FL 33881

  Under Construction. Welcome to this 3BR/2BA home featuring an open layout with updated cabinets, granite countertops & brand-new stainless-steel appliances. The kitchen flows into the dining & family room, perfect for entertaining. The private primary suite includes a spacious bath & walk-in closet, while two additional bedrooms share a full bath with a nearby linen storage. Enjoy outdoor living

  Reed Williams ASHTON WOODS FLORIDA REALTY LLC

  3323 Twilight Rd, Winter Haven, FL 33881
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  /43

  $399,999

  • 3 Beds
  • 3 Baths
  • 2,149 Sq Ft

  35 S Lake Fox Rd, Winter Haven, FL 33884

  Lakefront living on nearly 2 acres! This 3 bedroom, 3 bath home sits on 1.74 acres along the private shores of Lake Fox. Offering over 2,100 sq ft of living space, the property features spacious common areas, vaulted ceilings, and large windows with serene lake views. The split floor plan includes a generous primary suite, two additional bedrooms, and multiple living and dining spaces. The

  Michele Rueff EXP REALTY LLC

  35 S Lake Fox Rd, Winter Haven, FL 33884
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  $314,000 Open Sat 10:30AM - 12:30PM

  • 3 Beds
  • 2 Baths
  • 1,675 Sq Ft

  2519 Avenue East SW, Winter Haven, FL 33880

  OPEN SATURDAY from 10:30AM-12:30PM. BRAND NEW 2025 CONSTRUCTION – NO HOA – MOVE-IN READY! This 3 bedroom, 2 bathroom home offers 1,675 sq ft of open, modern living space with a 2-car garage and no HOA restrictions. Built in 2025, everything is new — roof, HVAC, plumbing, electrical, appliances — giving you peace of mind and low maintenance for years to come.The open-concept layout features

  Fanta Traore SIVEN PREMIER REAL ESTATE

  2519 Avenue East SW, Winter Haven, FL 33880
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  /22

  $315,000

  • 3 Beds
  • 2 Baths
  • 1,831 Sq Ft

  1019 Robin Ln, Winter Haven, FL 33884

  Charming residence in Winter Haven featuring 3 bedrooms and 2 bathrooms. This home has a spacious living area with abundant natural light, a modern kitchen with ample storage, and a serene backyard appropriate for relaxation. Located in a peaceful neighborhood with convenient access to local amenities, this property provides a welcoming atmosphere and comfortable living. Don't miss this

  Steven Koleno BEYCOME OF FLORIDA LLC

  1019 Robin Ln, Winter Haven, FL 33884
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  /27

  $300,990 New Construction

  • 4 Beds
  • 2.5 Baths
  • 1,880 Sq Ft

  6405 Domizio Dr, Winter Haven, FL 33884

  One or more photo(s) has been virtually staged. This expansive two-story Columbus has a well-designed layout, featuring a first floor dedicated to shared living and entertaining. The open concept design seamlessly connects the kitchen, dining room and family room, with a patio extending the interior space outdoors. Upstairs, a spacious loft separates the three secondary bedrooms from the serene

  Ben Goldstein LENNAR REALTY

  6405 Domizio Dr, Winter Haven, FL 33884
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  /4

  $318,967 New Construction

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

  2323 Brassie Ct, Winter Haven, FL 33884

  Under Construction. This two-story home features 4 bedrooms and 2 and a half baths. This Home begins with a two-story foyer opening up to the spacious first floor living spaces. The kitchen shines with abundant counter space and an island perfect for entertaining, Upstairs, you will find all four bedrooms and the large loft area. CUSTOM EXTERIOR includes 30-year mildew resistant dimensional

  Claudia Gutierrez ADAMS HOMES REALTY

  2323 Brassie Ct, Winter Haven, FL 33884
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  /14

  $365,900 New Construction

  • 4 - 5 Beds
  • 3.5 Baths
  • 2,819 Sq Ft

  Westbrooke II Plan at Harbor at Lake Henry - Single-Family Homes, Winter Haven, FL 33881

  Welcome home to the Westbrooke II by Highland Homes, a spacious two-story Florida home featuring an open living area on the first story and a flexible second-story layout! Downstairs, you will find a fully open living area including: A spacious gathering room. An open kitchen with a counter-height island, a large walk-in pantry, and a sunny dining cafe. A convenient powder room. The option to add

  Highland Homes Builder

  612 Ituna Cir Unit 37319444, Winter Haven, FL 33881
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  /26

  $339,990

  • 4 Beds
  • 2 Baths
  • 2,004 Sq Ft

  3030 Laurel Oak Ln, Winter Haven, FL 33884

  Welcome to your dream home in the heart of Villamar, where modern living meets serene surroundings. This stunning four-bedroom, two-bathroom residence is perfectly situated on a desirable corner lot, offering privacy and tranquility with no backyard neighbors, as it backs up to a lush conservation area and a picturesque pond. Step inside to discover a bright and airy open-concept design,

  David Small KELLER WILLIAMS REALTY SMART 1

  3030 Laurel Oak Ln, Winter Haven, FL 33884
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  /45

  $349,000

  • 3 Beds
  • 2 Baths
  • 2,020 Sq Ft

  312 Towhee Rd, Winter Haven, FL 33881

  Listing price is now below appraised value! Move-In Ready 4 Bedroom / 2 Bath Home on Nearly Half an Acre! Step into this beautifully updated 4-bedroom, 2-bath home featuring an open, split-bedroom floor plan perfect for comfortable living and entertaining. Built in 2005 and thoughtfully improved throughout, this home offers peace of mind with major updates already completed. Key Features &

  Judy Morgan FREEDOM REALTY

  312 Towhee Rd, Winter Haven, FL 33881
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  $340,000

  • 4 Beds
  • 2 Baths
  • 1,823 Sq Ft

  162 Andreas St, Winter Haven, FL 33881

  Back on the market! 1 year paid HOA!! Beautiful like new, energy efficient home for sale in the beautiful Winter Haven, FL. 42 Inch Upper Cabinets with Crown Molding, 15x15 Ceramic Tile Flooring, Extended Flooring throughout common and wet areas, Granite Countertops Kitchen and Bathrooms, fenced backyard, and Whirpool Stainless Steel Kitchen Appliances Included. Lucerne Park Reserve is located in

  Jessica Salvant Worthy Realty LLC

  162 Andreas St, Winter Haven, FL 33881
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  /20

  $335,000

  • 4 Beds
  • 2 Baths
  • 1,867 Sq Ft

  341 Alexzander Way, Winter Haven, FL 33881

  Thoughtfully designed for easy, low-maintenance living, this 4-bedroom, 2-bath 2021 home features a comfortable single-story layout, open-concept living area, and a generous primary suite ideal for everyday comfort and convenience. Filled with premium upgrades rarely found at this price point this home has been meticulously enhanced with over $25,000 in smart and luxury features, making it one of

  Dori Estrada LPT REALTY, LLC

  341 Alexzander Way, Winter Haven, FL 33881
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  /24

  $395,000

  • 3 Beds
  • 2 Baths
  • 1,716 Sq Ft

  4612 Reynosa Dr SW, Winter Haven, FL 33880

  Welcome home! Don’t miss the opportunity to own this one-of-a-kind, 3-bedroom, 2-bathroom, 2-car garage custom home. Upon arriving at the property, you are greeted by an oversized lot and mature trees in a quiet, well-established neighborhood. Inside, the home offers an open and split floor plan, cathedral ceilings, and an indoor/outdoor pool that flows from the back patio into the living room,

  Trent Shackelford LPT REALTY LLC

  4612 Reynosa Dr SW, Winter Haven, FL 33880
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  $363,990 New Construction

  • 4 - 5 Beds
  • 3 Baths
  • 2,531 Sq Ft

  Winston Plan at Annabelle Estates, Winter Haven, FL 33859

  The Winston floorplan offers a spacious two-story layout with four bedrooms and three full bathrooms. This well-designed home includes a two-car garage and features a functional flex room on the main level, ideal for a home office or extra living space. The first floor includes a cozy great room adjacent to the cafe and covered patio, creating an inviting space for relaxation and entertaining.

  Dream Finders Homes Builder

  5043 Abigail Dr Unit 36493016, Winter Haven, FL 33859
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  $374,990 New Construction

  • 5 Beds
  • 3 Baths
  • 2,531 Sq Ft

  256 Meredith Blvd, Winter Haven, FL 33881

  The Winston floorplan offers a spacious two-story layout with four bedrooms and three full bathrooms. This well-designed home includes a two-car garage and features a functional flex room on the main level, ideal for a home office or extra living space. The first floor includes a cozy great room adjacent to the cafe and covered patio, creating an inviting space for relaxation and entertaining.

  Dream Finders Homes Builder

  256 Meredith Blvd, Winter Haven, FL 33881
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  $319,990 New Construction

  • 3 Beds
  • 2 Baths
  • 1,624 Sq Ft

  329 Meredith Blvd, Winter Haven, FL 33881

  Beautiful Single Level, 2 Car Garage Home with Open Concept Living and 3 Bedrooms! Welcome to the Flagler floor plan, where timeless charm meets modern luxury. The home’s traditional elevation with a welcoming front porch sets the tone for elegance and comfort. Inside, a versatile flex space off the entry offers the perfect spot for a home office or cozy reading nook. The heart of the home

  DRB Homes Builder

  329 Meredith Blvd, Winter Haven, FL 33881
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  $369,900

  • 4 Beds
  • 3 Baths
  • 2,404 Sq Ft

  3686 Plymouth Dr, Winter Haven, FL 33884

  One or more photo(s) has been virtually staged. This spacious 4-bedroom, 3-bath home is located in the desirable 55+ gated community of Traditions at Ruby Lake. Upon entering, you’re greeted by a charming screened-in front porch. The open-concept floor plan features both a formal living room and a great room, with low-maintenance solid surface flooring throughout the main living areas. The great

  Eileen Belanger CENTURY 21 MYERS REALTY LAKE WALES

  3686 Plymouth Dr, Winter Haven, FL 33884
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  /30

  $319,740 New Construction

  • 5 Beds
  • 2 Baths
  • 1,708 Sq Ft

  2795 Adeline Ave, Winter Haven, FL 33881

  The property is located at 2795 Adeline Ave WINTER HAVEN FL 33881 priced at 319740, the square foot and stories are 1708, 1.The number of bath is 2, halfbath is 0 there are 5 bedrooms and 2 garages. For more details please, call or email.

  D.R. Horton Builder

  2795 Adeline Ave, Winter Haven, FL 33881
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  /35

  $327,000

  • 3 Beds
  • 2 Baths
  • 1,547 Sq Ft

  1211 Lake Loop, Winter Haven, FL 33880

  Welcome to this beautifully maintained 3-bed, 2-bath home on a spacious fenced corner lot. Pride of ownership shows throughout with a split floor plan, tile flooring in the main areas, and a bright dining space overlooking the landscaped front yard. The primary suite features a walk-in closet, upgraded tile, jacuzzi tub, and separate shower. French doors lead from the living room to a private

  Vanessa Armas TRUE FLORIDA REALTY LLC

  1211 Lake Loop, Winter Haven, FL 33880
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  /41

  $349,000 Open Sat 10AM - 12PM

  • 3 Beds
  • 2 Baths
  • 1,847 Sq Ft

  5329 Hogan Ln, Winter Haven, FL 33884

  Welcome to 5329 Hogan Lane in the beautiful gated community of Lake Ashton in Winter Haven, FL. This immaculate 3-bedroom, 2-bath home with over 1,800 square feet is ideally situated on a premium pond lot with peaceful water views and no rear neighbors.From the moment you arrive, the home’s curb appeal stands out with a new paver driveway and walkway leading to a charming screened front

  Susan Mayrant COLDWELL BANKER REALTY

  5329 Hogan Ln, Winter Haven, FL 33884
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  /23

  $325,000

  • 3 Beds
  • 2 Baths
  • 1,604 Sq Ft

  29 Golfview Cir NE, Winter Haven, FL 33881

  Short Sale. We are in the process of getting a short sale approved. So expect delays.Welcome to 29 Golfview Circle NE, a beautifully modernized Winter Haven property offering a rare combination of charm, flexibility, and income-producing potential. The main residence features 3 bedrooms and 2 baths with an open, inviting layout that includes spacious living and dining areas, stainless steel

  Chris Sakamoto MARK SPAIN REAL ESTATE

  29 Golfview Cir NE, Winter Haven, FL 33881
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  /22

  $359,000

  • 4 Beds
  • 2.5 Baths
  • 2,696 Sq Ft

  326 Meadowbrook Blvd, Winter Haven, FL 33881

  One or more photo(s) has been virtually staged. Welcome to this stunning two-story home located in the heart of Winter Haven! Built in 2021, this spacious 4-bedroom, 2.5-bath residence offers 2,696 sq. ft. of living space designed for modern comfort and style. The open floor plan features a bright and inviting living area, perfect for gatherings and entertaining. The kitchen boasts ample

  David Gonzalez Martell LPT REALTY, LLC

  326 Meadowbrook Blvd, Winter Haven, FL 33881
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  /29

  $334,000

  • 3 Beds
  • 2 Baths
  • 1,894 Sq Ft

  6518 Crescent Loop, Winter Haven, FL 33884

  Charming, move-in ready 3-bed, 2-bath home in a peaceful Winter Haven community. Features an open living/dining layout, updated kitchen with modern finishes, and spacious bedrooms. Enjoy plenty of natural light, a private backyard perfect for gatherings and outdoor living, and an attached 2-car garage. Well-maintained and thoughtfully updated, this home offers both comfort and convenience.

  Mona Cherkaoui WORLD PROPERTIES GROUP

  6518 Crescent Loop, Winter Haven, FL 33884
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  $326,900 New Construction

  • 3 Beds
  • 2 Baths
  • 2,005 Sq Ft

  4494 Rapallo Ave, Winter Haven, FL 33884

  Move-in ready home for sale in Winter Haven, FL, with 3 bedrooms and a den! Designed for your lifestyle, the Serendipity features an open living area with luxury vinyl plank flooring under volume ceilings. Relax in your luxurious owner's suite with an elegant tray ceiling, and a spacious en-suite bath with dual vanities, a decorative tiled shower with glass enclosure, and two walk-in wardrobes.

  Highland Homes Builder

  4494 Rapallo Ave, Winter Haven, FL 33884
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  /21

  $329,000

  • 3 Beds
  • 2 Baths
  • 1,716 Sq Ft

  1144 High Seas St, Winter Haven, FL 33880

  Step inside this well-designed single-family home offering comfort, functionality, and a layout that truly makes sense. You’re welcomed by a screened front porch and a beautifully landscaped front yard, setting the tone before you even walk through the door. Inside, you’ll find engineered wood flooring throughout the main living areas with ceramic tile in both bathrooms. The living and dining

  Julie Sutphin CRAIG BURKE REAL ESTATE GROUP, LLC

  1144 High Seas St, Winter Haven, FL 33880
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  /27

  $339,999

  • 4 Beds
  • 2.5 Baths
  • 2,364 Sq Ft

  905 Cambridge Dr, Winter Haven, FL 33881

  Discover comfort, style, and community living at its best in Lucerne Reserve Park — a highly desirable neighborhood in Winter Haven!This 4-bedroom, 2.5-bath home offers 2,300+ of bright, open living space designed for both gatherings and everyday comfort. The inviting floor plan is filled with natural light, while the kitchen flows seamlessly into dining and family areas. Upstairs, retreat to

  Sherraine Felder COLDWELL BANKER REALTY

  905 Cambridge Dr, Winter Haven, FL 33881
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  /44

  $325,000

  • 3 Beds
  • 3 Baths
  • 2,377 Sq Ft

  2 Casarena Ct, Winter Haven, FL 33881

  **RECENTLY REDUCED AND PRICED TO SELL** Welcome to this spacious 3 bedroom, 3 bath townhouse located in the private, gated, lakefront community of Casarena on the Lakes. Situated on the Winter Haven Chain of Lakes with a desirable south-facing view of Lake Cannon, this home offers the rare opportunity to enjoy both sunrise and sunset views right from your own space. Three-bedroom properties in

  Kylie Berry BERRY REALTY & APPRAISAL SERVICES PA

  2 Casarena Ct, Winter Haven, FL 33881
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  $325,000

  • 4 Beds
  • 2 Baths
  • 2,280 Sq Ft

  321 Fish Hawk Dr, Winter Haven, FL 33884

  Welcome to this beautifully maintained home located in the highly desirable Winter Haven area, offering comfort, convenience, and the best of Florida living. Nestled in a peaceful neighborhood, this residence features an inviting layout perfect for both everyday living and entertaining. Step inside to discover a bright, open floor plan with ample natural light and spacious living areas. The

  Cliff Glansen FLATFEE.COM

  321 Fish Hawk Dr, Winter Haven, FL 33884
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  /29

  $365,000

  • 4 Beds
  • 2 Baths
  • 1,823 Sq Ft

  2756 San Marco Way, Winter Haven, FL 33884

  Immaculate, move in ready, 4 bedroom/2 bath home. Large covered Screen Enclosure in the backyard. All bedrooms have been upgraded to Laminate flooring. All appliances included with home. All window treatments stay with home. Open Floorplan great for Family get togethers. Neighborhood has 2 community pools, Clubhouse and playgrounds for your family ready to use. Winter Haven is known for its

  Alfredo Lopez FIERCE REALTY

  2756 San Marco Way, Winter Haven, FL 33884
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  /22

  $326,900 New Construction

  • 3 - 4 Beds
  • 2 Baths
  • 2,005 Sq Ft

  Serendipity Plan at VillaMar, Winter Haven, FL 33884

  Welcome home to the Serendipity by Highland Homes! This sunny, spacious, open-layout home features large bedrooms, flexible plan options, and desirable outdoor living space! The Serendipity features: A bright and open kitchen with a large counter-height island, walk-in pantry, and adjacent dining cafe. A flex-use den or optional 4th bedroom. A spacious owner's suite with an elegant tray ceiling,

  Highland Homes Builder

  521 Vittorio Dr Unit 37316008, Winter Haven, FL 33884
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  $355,000

  • 4 Beds
  • 2 Baths
  • 1,903 Sq Ft

  4495 Mandolin Blvd, Winter Haven, FL 33884

  Price Improvement! Motivated seller brings added opportunity on this inviting four-bedroom, two-bathroom single family home in Winter Haven. Featuring a desirable split floor plan, this home offers privacy comfort, space, and functionality for the primary suite while maintaining an easy, natural flow throughout the main living areas perfect for everyday living and entertaining.The spacious

  Audith Poleon AUDITH POLEON REALTY

  4495 Mandolin Blvd, Winter Haven, FL 33884
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  $365,900 New Construction

  • 4 - 5 Beds
  • 3.5 Baths
  • 2,587 Sq Ft

  Wesley II Plan at Harbor at Lake Henry - Single-Family Homes, Winter Haven, FL 33881

  Welcome home to the Wesley II by Highland Homes, a two-story Florida home that lives large with an open living area on the first story and a flexible second-story layout! Downstairs, enjoy a fully open living area with: A large gathering room. An open kitchen with a counter-height buttery island or optional galley island, a walk-in pantry, and a sunny dining cafe. A convenient powder room. An

  Highland Homes Builder

  612 Ituna Cir Unit 37319434, Winter Haven, FL 33881
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  $301,366 New Construction

  • 4 Beds
  • 3 Baths
  • 2,200 Sq Ft

  2123 Cartgate Ln, Winter Haven, FL 33884

  This 2200 square foot Home is a stunning home design that offers a perfect balance of style and functionality. With 4 bedrooms and 3 baths, this home provides ample space for comfortable living. The open-concept layout seamlessly connects the kitchen, dining area, and living room, creating a spacious and inviting atmosphere. The modern kitchen is equipped with high-quality appliances, a large

  Claudia Gutierrez ADAMS HOMES REALTY

  2123 Cartgate Ln, Winter Haven, FL 33884
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  /34

  $314,990 New Construction

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

  1730 Hummingbird Rd, Winter Haven, FL 33884

  Under Construction. 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

  Paul King DR HORTON REALTY OF CENTRAL FLORIDA LLC

  1730 Hummingbird Rd, Winter Haven, FL 33884
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  /21

  $348,950 New Construction

  • 4 Beds
  • 3 Baths
  • 2,670 Sq Ft

  5331 Mickey Ave, Winter Haven, FL 33883

  Discover this must-see Tourmaline home. Included features: an inviting covered entry; an expansive great room; a well-appointed kitchen offering 42" cabinets, quartz countertops, a roomy pantry, a center island and an adjacent dining area; a beautiful primary suite showcasing an immense walk-in closet and a private bath; a convenient laundry; an airy loft; a storage area and a covered patio. This

  Stephanie Morales AXEN REALTY, LLC

  5331 Mickey Ave, Winter Haven, FL 33883
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  /15

  $305,000

  • 4 Beds
  • 2 Baths
  • 1,857 Sq Ft

  621 Vittorio Dr, Winter Haven, FL 33884

  Beautiful, spacious, and cozy house, practically new, with an open feel that gives it a pleasant and welcoming feeling of family togetherness. All appliances included. Beautiful laminate flooring throughout the house's social areas. The house has a screen in the front and back. Solar panels. Pleasant and spacious backyard. The community has a pool, playground, dog park, and walkways.Location:

  Jesus Nessy MY REALTY GROUP, LLC.

  621 Vittorio Dr, Winter Haven, FL 33884
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  /46

  $305,000 Open Sun 11:30AM - 4PM

  • 3 Beds
  • 2 Baths
  • 1,040 Sq Ft

  509 Clayton Cir, Winter Haven, FL 33880

  One or more photo(s) has been virtually staged. SELLER IS MOTIVATED!!! 20 MINUTES AWAY FROM LEGOLAND!!! NEW FLOORING INSTALLED IN FEBRUARY 2026!!!! NEW ROOF INSTALLED IN 2022!!! This 3-bedroom, 2-bathroom home offers the perfect combination of comfort, functionality, and location. The property features a screened-in back porch overlooking a private, fully fenced backyard — ideal for relaxing or

  Julia Ferreira LPT REALTY, LLC

  509 Clayton Cir, Winter Haven, FL 33880

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