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

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  $469,990 Open Sat 12:30PM - 3:30PM

  • 4 Beds
  • 3 Baths
  • 2,697 Sq Ft

  2512 Sherwood St, Winter Haven, FL 33881

  A beautiful family home is now available in the desirable gated community of Crossroads at Lake Region. This 4-bedroom, 3-bath property feels like new. The welcoming covered entry features 8-foot glass doors with sidelights that fill the space with natural light and open into the foyer, great room, and kitchen area with impressive 13' ceilings. The well-designed 3-way split floor plan offers

  Brian Cox KELLER WILLIAMS REALTY SMART 1

  2512 Sherwood St, Winter Haven, FL 33881
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  $500,000

  • 5 Beds
  • 2 Baths
  • 2,006 Sq Ft

  1818 6th St SE, Winter Haven, FL 33880

  ***FULLY RENOVATED***Discover the perfect blend of modern upgrades and timeless charm in this beautifully updated 3-bedroom, 2-bathroom home.This beautiful property fully renovated with the total 5 bedrooms, new kitchen, new living room, new floor, new bathrooms and the best new backyard in the city. Nestled between Orlando and Tampa with no HOA or CDD, this property offers unmatched freedom and

  Erika Pinto GARCIA REALTY GROUP

  1818 6th St SE, Winter Haven, FL 33880
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  $489,900

  • 3 Beds
  • 2 Baths
  • 2,023 Sq Ft

  3971 Island Lakes Dr, Winter Haven, FL 33881

  2023 Roof, 2022 POOL! Welcome to this pristine, beautifully maintained home in the quiet and highly desirable Island Lakes community—where there’s no through traffic and peaceful living comes naturally. This property features a newer roof put on in 2023, a newer in-ground pool put in 2022, and a large backyard shed, offering the perfect blend of comfort, storage, and outdoor enjoyment. Step

  Keith St. Onge LA ROSA REALTY PRESTIGE

  3971 Island Lakes Dr, Winter Haven, FL 33881
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  $475,990 New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,787 Sq Ft

  1745 Hummingbird Rd, Winter Haven, FL 33884

  The property is located at 1745 Hummingbird Road WINTER HAVEN FL 33884 priced at 475990, the square foot and stories are 2787, 1.The number of bath is 3, halfbath is 1 there are 4 bedrooms and 3 garages. For more details please, call or email.

  D.R. Horton Builder

  1745 Hummingbird Rd, Winter Haven, FL 33884
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  $400,000

  • 4 Beds
  • 2 Baths
  • 2,142 Sq Ft

  126 Lake Region Cir, Winter Haven, FL 33881

  ALMOST PARADISE! Enjoy the peaceful surroundings and relaxing environment from this 2142 SF executive style home located in The Gates of Lake Region, a well maintained and GATED community close to the Winter Haven Country Club! NEED SPACE? This customized 4BR/2BA home was designed with an open floor plan with split bedrooms, formal dining room and living room ( which could be easily used as a

  Carol Sheil JUDY B CLEAVES PROPERTIES INC

  126 Lake Region Cir, Winter Haven, FL 33881
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  $500,000

  • 4 Beds
  • 2 Baths
  • 1,842 Sq Ft

  1400 Axel Cir, Winter Haven, FL 33880

  Beautiful 4 bedrooms, 2 bathrooms home built in 2022, offered fully furnished and move-in ready — just bring your toothbrush. Located in Winter Haven, FL, only a few miles from LEGOLAND. Modern open floor plan, spacious kitchen, and comfortable living areas, perfect as a primary residence, vacation home, or short-term rental investment. Enjoy a great location near attractions, shopping, dining,

  Domingo Hernandez Ugarit Realty

  1400 Axel Cir, Winter Haven, FL 33880
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  $464,900

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

  6308 Pinehurst Loop, Winter Haven, FL 33884

  Welcome to this beautifully upgraded 3-bedroom, 2-bath home offering 2,045 square feet of refined living space in the highly desirable Lake Ashton 55+ golf community—where luxury meets an active, resort-style lifestyle. This thoughtfully designed home features top-notch upgrades throughout, including an additional sliding glass door leading to the back patio, flooding the living space with

  Cliff Glansen FLATFEE.COM

  6308 Pinehurst Loop, Winter Haven, FL 33884
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  $415,000

  • 5 Beds
  • 3 Baths
  • 2,944 Sq Ft

  592 Lake Smart Blvd, Winter Haven, FL 33881

  Solar Panels Will Be Paid Off at Closing!! - Offered at $415,000. An exceptional value for a fully upgraded residence on a spacious corner, lake-view lot within one of Winter Haven’s most desirable communities. Strategically priced to drive immediate interest, this home delivers a refined balance of comfort, scale, and modern efficiency. This beautifully updated 5-bedroom, 3-bath home features an

  Oscar Allende KELLER WILLIAMS LEGACY REALTY

  592 Lake Smart Blvd, Winter Haven, FL 33881
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  $448,900

  • 3 Beds
  • 2 Baths
  • 2,031 Sq Ft

  5225 Pebble Beach Blvd, Winter Haven, FL 33884

  This FULLY FURNISHED, turnkey Lake Ashton retreat offers a seamless blend of comfort, elegance, and resort-style living. From the moment you walk in, the open-concept Sebastian model welcomes you with soaring ceilings, crown molding, and tile flooring that flows effortlessly through the main living areas. The split floorplan ensures privacy and functionality, with each room thoughtfully equipped

  Candra Alston LAKE ASHTON REALTY INC.

  5225 Pebble Beach Blvd, Winter Haven, FL 33884
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  $404,500 Open Sat 11AM - 1PM

  • 3 Beds
  • 2 Baths
  • 2,378 Sq Ft

  716 Santa Maria Dr, Winter Haven, FL 33884

  IMPROVED PRICE!! LOCATION, LOCATION!! Gorgeous 3 bed, 2 bath POOL home with idyllic views across pretty pond with water frontage and private wooded island!! Located in the sought after gated, Overlook Estates on a spacious corner lot with mature landscaping. The open-concept living area creates an inviting atmosphere, ideal for both relaxed family gatherings and formal entertaining. Enter into

  Sue Webb WATSON REALTY CORP.

  716 Santa Maria Dr, Winter Haven, FL 33884
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  $469,000

  • 4 Beds
  • 3 Baths
  • 2,374 Sq Ft

  349 Ruby Lake Loop, Winter Haven, FL 33884

  Tucked away at the end of a quiet street in the gated, golf cart–friendly community of Ruby Lakes, this 4-bedroom, 3-bath beauty is all about relaxed Florida living. From the long driveway and two-car garage to the lush, well-kept landscaping, this home gives you that “welcome home” feeling from the very start. Step through the double front doors and into a bright, open layout that flows

  Jen Lysak EXP REALTY LLC

  349 Ruby Lake Loop, Winter Haven, FL 33884
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  $425,000

  • Land
  • 2.45 Acres
  • $173,469 per Acre

  0 Old Helena Rd, Winter Haven, FL 33884

  Discover the perfect canvas for your waterfront dreams with this stunning vacant lakefront lot. Nestled along the serene shores of Lake Eloise, this 2.45 acre parcel offers panoramic water views, direct lake access, and the peaceful privacy of nature all around. Whether you're envisioning a potential custom-built home, cozy cabin, or weekend getaway, this property provides the ideal foundation.

  John Rodgers STAR REALTY OF WINTER HAVEN

  0 Old Helena Rd, Winter Haven, FL 33884
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  $426,000

  • 4 Beds
  • 2 Baths
  • 2,249 Sq Ft

  3108 Buckeye Pointe Dr, Winter Haven, FL 33881

  Welcome to 3108 Buckeye Point Dr — where comfort meets convenience in the heart of Winter Haven. From the moment you arrive, this home invites you in with a layout designed for the way you truly live. With 4 bedrooms and 2 full bath the living spaces feel open yet connected, creating an easy flow for both everyday routines and weekend gatherings. Natural light enhances the home’s warmth, while

  JP Phillips KELLER WILLIAMS REALTY SMART

  3108 Buckeye Pointe Dr, Winter Haven, FL 33881
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  $477,555

  • 4 Beds
  • 2 Baths
  • 2,428 Sq Ft

  1051 Lena Run Ct, Winter Haven, FL 33880

  Welcome home to this well-priced, beautifully maintained 4-bedroom, 2-bath residence located in the highly sought-after gated Hidden Creek Community of Winter Haven. Perfectly positioned just minutes from the Polk Parkway, LEGOLAND Florida Resort, and conveniently situated between Lakeland and Winter Haven, this home offers both comfort and unbeatable accessibility. From the moment you arrive,

  Brandy Duncan COLDWELL BANKER REALTY

  1051 Lena Run Ct, Winter Haven, FL 33880
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  $439,000

  • 4 Beds
  • 2.5 Baths
  • 2,495 Sq Ft

  108 Lake Region Blvd N, Winter Haven, FL 33881

  Gated custom home in the Gates of Lake Region! This quiet and highly-desirable neighborhood has the look, feel and privacy of an age-restricted community, but it is open to all ages. This property was constructed as a builder’s model home so it offers numerous upgrades and architectural details that can be found throughout. Located within the quaint, gated community of The Gates of Lake Region

  Michael Stone THE STONES REAL ESTATE FIRM

  108 Lake Region Blvd N, Winter Haven, FL 33881
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  $418,990 New Construction

  • 4 Beds
  • 3 Baths
  • 2,336 Sq Ft

  1749 Hummingbird Rd, Winter Haven, FL 33884

  The property is located at 1749 Hummingbird Road WINTER HAVEN FL 33884 priced at 418990, the square foot and stories are 2336, 1.The number of bath is 3, halfbath is 0 there are 4 bedrooms and 3 garages. For more details please, call or email.

  D.R. Horton Builder

  1749 Hummingbird Rd, Winter Haven, FL 33884
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  $495,000

  • 4 Beds
  • 3 Baths
  • 2,884 Sq Ft

  570 Sanctuary Blvd, Winter Haven, FL 33881

  Bring the entire family & gather your friends at this majestic home artfully laid out in an airy, open floor plan with plenty of rooms & abundant spaces. The huge entry foyer welcomes you to the delightful formal dining room w/ alluring arch-designed interiors, & natural light freely flowing to the grand living areas. The luxurious kitchen encompasses a counter-height island, a wide seated

  Lienyvette Grimaldo MAZELG REALTY

  570 Sanctuary Blvd, Winter Haven, FL 33881
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  $405,000

  • 3 Beds
  • 2 Baths
  • 2,218 Sq Ft

  104 Woden Way, Winter Haven, FL 33884

  Valhalla - A GATED subdivision with pool, club house and more! 3-bedroom, 2-bath villa home with a connecting property but considered a single family home. This special villa has a functional layout with updated features throughout. A screened entry with leaded glass doors opens to vaulted ceilings and custom architectural touches.The open concept kitchen includes granite countertops,

  Karen Myers CENTURY 21 MYERS REALTY

  104 Woden Way, Winter Haven, FL 33884
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  $430,000 Open Sat 11AM - 2PM

  • 4 Beds
  • 2.5 Baths
  • 2,497 Sq Ft

  280 Lake Smart Cir, Winter Haven, FL 33881

  Welcome to your 4 bedroom, 2.5 bathroom 2 story home located conveniently in Winter Haven with easy access to shopping, dining, and major roadways. Arriving at the home, you’ll appreciate the tastefully landscaped yard and screened in entry way. Entering the home, you’ll find LVP flooring throughout the home. The bright and open kitchen features stainless steel appliances, quartz countertops, a

  Casandra Vann KELLER WILLIAMS REALTY SMART

  280 Lake Smart Cir, Winter Haven, FL 33881
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  /25

  $440,000

  • 4 Beds
  • 3 Baths
  • 2,206 Sq Ft

  252 Lake Link Rd, Winter Haven, FL 33884

  SELLER IS OFFERING $5,000 towards closing depending on offer!!! Welcome to this beautifully updated 4 bedroom, 3 bath pool home, ideally positioned on a half-acre lot in the highly desirable gated community of Lake Link. Surrounded by oak-lined streets and refreshing lake breezes, this home combines elegant updates with a functional layout designed for everyday living and entertaining. Inside, an

  Katie Melson THE STONES REAL ESTATE FIRM

  252 Lake Link Rd, Winter Haven, FL 33884
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  $469,000

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

  6165 Pebble Beach Blvd, Winter Haven, FL 33884

  Welcome to the next exciting chapter of your life in Lake Ashton, Central Florida’s premier 55+ active-adult community, where this immaculately maintained 3-bedroom, 2-bath home awaits. From the stone on the front elevation and bronze screened front entry to the 32’ x 18’ bronze screened veranda, the home impresses in every way. It is situated on a quiet cul-de-sac with views of a large pond and

  Brad Kirwan GLOBAL LIFESTYLE LLC

  6165 Pebble Beach Blvd, Winter Haven, FL 33884
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  $400,000

  • 5 Beds
  • 3 Baths
  • 2,579 Sq Ft

  129 Lake Otis Rd, Winter Haven, FL 33884

  Short Sale. This charming home is a diamond in the rough, waiting for the right owner to unlock its full potential. Located in a sought-after neighborhood of picturesque red brick homes, this property offers a unique opportunity for those with vision and ambition. This home is being sold as a short sale, making it an ideal project for those looking to invest in a renovation loan and transform it

  Kelley Vogel Blackburn COLDWELL BANKER REALTY

  129 Lake Otis Rd, Winter Haven, FL 33884
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  /10

  $400,000

  • Land
  • 0.39 Acre
  • $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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  $432,990 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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  $424,900 Open Sun 12PM - 2PM

  • 3 Beds
  • 2 Baths
  • 2,095 Sq Ft

  4033 Phoenician Way, Winter Haven, FL 33884

  Located within the prestigious Lake Ashton 55+ community, offering gated entry with 24-hour guard service, this beautifully appointed three-bedroom, two-bath pool home offers a refined Florida lifestyle defined by comfort, quality, and thoughtful design. Lush, well-maintained landscaping and a welcoming screened front porch create an elegant first impression and set the tone for the home’s

  Jessica Hancock-Batson THE STONES REAL ESTATE FIRM

  4033 Phoenician Way, Winter Haven, FL 33884
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  $499,900

  • 5 Beds
  • 3 Baths
  • 3,022 Sq Ft

  1491 Axel Cir, Winter Haven, FL 33880

  Conveniently located in the heart of Winter Haven, this 5 Bedroom 3 Bathroom home with two Flex Rooms is move in ready and close to everything loved, including: Easy commuting, Grocery Stores, Shopping, Dining, Chain of Lakes, Boat Ramps, Scenic Walking Trails, Legoland Florida Resort, and Beaches just an hour and a half away! Step outside to your private oasis featuring a Caged Saltwater Pool

  Andrea Friedmann KELLER WILLIAMS REALTY SMART 1

  1491 Axel Cir, Winter Haven, FL 33880
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  $465,000

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

  183 Lake Thomas Dr, Winter Haven, FL 33880

  Situated on the sought-after Lake Thomas Drive, this charming 3-bedroom, 2-bathroom residence offers the perfect blend of comfort and convenience. The open-concept living area flows effortlessly, creating an ideal space for entertaining friends or quiet family evenings. Step outside to a spacious backyard, perfect for weekend BBQs or enjoying the Florida sunshine. Located just minutes from the

  Lucy Martinez CENTURY 21 WOLF'S CROSSING REALTY

  183 Lake Thomas Dr, Winter Haven, FL 33880
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  $450,000

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

  1209 Sawgrass Dr, Winter Haven, FL 33884

  Your Florida Dream Home Awaits in Lake Ashton, an exclusive gated 55+ community. Discover this beautiful 3 bedroom, 2 bathroom Sebastian Floor Plan home with an oversized backyard with pond and trees beyond. This PET FREE home is perfectly positioned; one home removed from a cul-de-sac. With over 2,045 sq. ft. living area, this home offers great curb appeal with a well maintained lawn, gutters,

  Lori Raath LAKE ASHTON REALTY INC.

  1209 Sawgrass Dr, Winter Haven, FL 33884
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  $459,000

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

  6216 Pinehurst Loop, Winter Haven, FL 33884

  Stunning Sebastian Floor Plan Home in an Exclusive, Secure 55+ Florida Community, Lake Ashton. Discover this exceptional single-family home built in 2022, designed with every modern comfort in mind. Perfectly positioned home with a POND VIEW. With a thoughtfully crafted open floor plan, this home with over 2,045 sq.ft. living area, combines style and functionality, perfect for those seeking

  Lori Raath LAKE ASHTON REALTY INC.

  6216 Pinehurst Loop, Winter Haven, FL 33884
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  /30

  $409,000 Open Sun 12PM - 2PM

  • 3 Beds
  • 2.5 Baths
  • 2,148 Sq Ft

  2901 Plantation Rd, Winter Haven, FL 33884

  Welcome home to effortless Florida living in the highly sought-after Plantation community of Cypresswood, where space, comfort, and lifestyle come together. Set on an oversized 0.46-acre lot, this beautifully maintained single-story ranch-style home offers privacy, flexibility, and room to breathe—both inside and out. Step inside to a bright, open layout made for gathering and relaxing. The

  Mark Loewenberg KELLER WILLIAMS REALTY/P B

  2901 Plantation Rd, Winter Haven, FL 33884
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  $405,000

  • 3 Beds
  • 2 Baths
  • 2,027 Sq Ft

  4081 Dunmore Dr, Lake Wales, FL 33859

  Discover exceptional value in the guard-gated 55+ community of Lake Ashton with this pristine waterfront residence, featuring the significant advantage of a fully paid CDD debt. Situated on a prime waterfront lot, this home is just steps away from the resort-style amenities. This 3-bedroom, 2-bath property with a separate office offers impressive energy savings through leased solar panels at

  Mary Sorrell MAZELG REALTY

  4081 Dunmore Dr, Lake Wales, FL 33859

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