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

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  /18

  $485,000

  • Land
  • 11.52 Acres
  • $42,101 per Acre

  0 Lucerne Park Rd Unit MFRO6281805, Winter Haven, FL 33881

  Prime Investment Opportunity! This 11+ acre vacant lot is zoned R-3 multi-family and residential, providing exceptional potential for development. Featuring approximately 1,047 feet of frontage along State Road 544, the property is situated in a rapidly growing area—ideal for investors and developers. Nearby utilities include electric, water, and sewer for convenient access. All dimensions are

  Cardichon Christloudjy EXP REALTY LLC

  0 Lucerne Park Rd Unit MFRO6281805, Winter Haven, FL 33881
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  /16

  $414,900

  • 4 Beds
  • 2 Baths
  • 1,400 Sq Ft

  40 Jimmy Lee Rd, Winter Haven, FL 33880

  GREAT COUNTRY LIVING ON A SPRAWLING 2.3 ACRE LOT ON A DEAD END STREET WITH NO HOA!! CENTRALLY LOCATED BETWEEN WINTER HAVEN, LAKELAND, AUBURNDALE, AND POLK PARKWAY. THIS WELL MAINTAINED HOMe FEATURES NEWER STAINLESS KITCHEN APPLIANCES 4tH BEDROOM HAS MULTIPLE BUILTINS, COULD BE USED AS OFFICE OR HOBBY ROOM, ROOF AND A/C ARE JUST TWO YEARS OLD. RELAX ON YOUR SCREENED PATIO OVERLOOKING YOUR SERENE

  Rebecca Brown SUN N LAKES REALTY, LLC

  40 Jimmy Lee Rd, Winter Haven, FL 33880
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  /43

  $402,546 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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  /50

  $459,990

  • 4 Beds
  • 3 Baths
  • 2,357 Sq Ft

  402 Terranova St, Winter Haven, FL 33884

  **Closing Cost assistance, Brand New Roof**Welcome to 402 Terranova Street in Winter Haven, FL!This beautifully updated 4-bedroom, 3-bath pool home offers the perfect blend of comfort, style, and convenience. Nestled in the desirable gated community of Terranova, this residence sits on a quarter-acre lot—ideal for entertaining, outdoor fun, or simply enjoying the Florida sunshine. Step inside

  Sejida Self OPULENT REALTY INTERNATIONAL

  402 Terranova St, Winter Haven, FL 33884
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  /23

  $400,000

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

  29 Golfview Cir NE, Winter Haven, FL 33881

  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 appliances, and a comfortable primary suite with a walk-in closet. Enjoy outdoor living

  Chris Sakamoto MARK SPAIN REAL ESTATE

  29 Golfview Cir NE, Winter Haven, FL 33881
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  /86

  $417,000

  • 3 Beds
  • 2 Baths
  • 1,533 Sq Ft

  2755 Taylor Rd, Winter Haven, FL 33880

  Charming 4.33-Acre Property with Potential for Additional Home Discover the appeal of this spacious 4.33-acre property thoughtfully prepared for comfortable living and future expansion. While the land cannot currently be subdivided, it offers the unique opportunity to build an additional home on-site, providing flexibility for growing families or investment possibilities. Key Features and Layout

  Rick DePalma KELLER WILLIAMS REALTY SMART 1

  2755 Taylor Rd, Winter Haven, FL 33880
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  /25

  $409,900 New Construction

  • 5 Beds
  • 3 Baths
  • 2,244 Sq Ft

  1783 White Elephant Loop, Winter Haven, FL 33884

  Welcome to the Spring model in Peach Crossings, a spacious five-bedroom, three-bathroom, two-story home situated on a desirable corner lot with no rear neighbors, offering extra privacy and an open feel.As you step inside, a long and inviting foyer welcomes you into the home. The first floor boasts a bright and open family room, perfect for gathering, along with a modern kitchen featuring a

  Gayle Van Wagenen LGI REALTY- FLORIDA, LLC

  1783 White Elephant Loop, Winter Haven, FL 33884
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  /55

  $424,900

  • 4 Beds
  • 5 Baths
  • 2,368 Sq Ft

  937 Avenue L SE, Winter Haven, FL 33880

  Discover Florida living at its best in this charming Winter Haven home! Enjoy a beautifully updated kitchen featuring modern finishes and plenty of space for cooking and gathering. Step outside to your own private oasis — a sparkling swimming pool perfect for relaxing or entertaining year-round. This property is well-kept, inviting, and ready for its next chapter. The Seller is motivated, making

  Kurt Neubauer AGILE GROUP REALTY

  937 Avenue L SE, Winter Haven, FL 33880
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  /43

  $479,900

  • 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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  /26

  $499,900

  • 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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  /68

  $409,000

  • 8 Beds
  • 4 Baths
  • 2,862 Sq Ft

  2435 Edwin St NE, Winter Haven, FL 33881

  Tenant occupied.Do not disturb tenant, contact selling agent to request showing. 24 hr notice please.

  Pedro Fernandez Salvador CONTEMPORARY REALTY GROUP

  2435 Edwin St NE, Winter Haven, FL 33881
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  /28

  $415,000

  • 5 Beds
  • 3 Baths
  • 2,696 Sq Ft

  344 Alexzander Way, Winter Haven, FL 33881

  Welcome to this stunning 5-bedroom, 3-bath home located in the Jace Landing community of Winter Haven. Built in 2021, this modern two-story residence provides nearly 2,700 square feet of living space designed for comfort, flexibility, and contemporary living. The open-concept layout features a bright and spacious great room, modern finishes, and a large kitchen with stainless steel appliances,

  Andres Ramirez DALTON WADE INC

  344 Alexzander Way, Winter Haven, FL 33881
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  /53

  $400,000

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

  126 Lake Region Cir, Winter Haven, FL 33881

  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 study, library

  Carol Sheil JUDY B CLEAVES PROPERTIES INC

  126 Lake Region Cir, Winter Haven, FL 33881
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  /27

  $414,500

  • 4 Beds
  • 2 Baths
  • 2,013 Sq Ft

  807 Hart Lake St, Winter Haven, FL 33884

  Nestled in the exclusive gated community of Hart Lake Hills, this stunning four-bedroom, two-bath home offers a perfect blend of style, comfort, and functionality, all with the added bonus of water access to Hart Lake! As you approach, you’ll be greeted by a quaint covered front porch, an inviting space that whispers “welcome home.” Step inside to discover an open-concept floor plan that

  David Small KELLER WILLIAMS REALTY SMART 1

  807 Hart Lake St, Winter Haven, FL 33884
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  /73

  $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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  /54

  $425,000

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

  716 Santa Maria Dr, Winter Haven, FL 33884

  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 the foyer which is

  Sue Webb WATSON REALTY CORP.

  716 Santa Maria Dr, Winter Haven, FL 33884
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  /56

  $469,000 Open Sun 12PM - 2PM

  • 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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  /39

  $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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  /50

  $440,000

  • 4 Beds
  • 2 Baths
  • 1,982 Sq Ft

  260 Lake Smart Cir, Winter Haven, FL 33881

  Experience the perfect blend of style, comfort, and sustainability in this beautifully maintained 4-bedroom, 2-bathroom home, built in 2021. Nestled in a serene neighborhood, this home offers not only modern features but also breathtaking views of Lake Smart which it's part of Polk County Chain of Lakes. Highlights Include: Stunning lake view to enjoy daily sunrises, sunsets, and peaceful vibes.

  Veddy Diaz Rosario CHARLES RUTENBERG REALTY ORLANDO

  260 Lake Smart Cir, Winter Haven, FL 33881
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  /53

  $449,000

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

  108 Lake Region Blvd N, Winter Haven, FL 33881

  Builder’s model home with numerous upgrades and architectural details throughout. Located within the quaint, gated community of The Gates of Lake Region and built by Alan Ulch Construction, the home offers nearly 2,500 square feet of spacious living area. Construction includes high-efficiency Ytong concrete block, providing superior sound reduction, enhanced structural performance, and meaningful

  Michael Stone THE STONES REAL ESTATE FIRM

  108 Lake Region Blvd N, Winter Haven, FL 33881
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  /19

  $429,900

  • 3 Beds
  • 2 Baths
  • 2,122 Sq Ft

  99 14th St SE, Winter Haven, FL 33884

  Introducing this 3 bedroom 2 bath home, located Near Downtown Winter Haven in the Community of Lake Elbert sitting on just under a quarter acre of land. This home is one block up from the Beautiful Lake Elbert and Less than a Half Mile from Lake Elbert Elementary School. Step Inside you will find just under 2200 square feet of space, that has been completely reimagined. This home design includes,

  Richard Rutledge CHARLES RUTENBERG REALTY ORLANDO

  99 14th St SE, Winter Haven, FL 33884
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  /2

  $402,000

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

  Unlisted Address

  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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  /40

  $419,900

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

  1476 Avenue F NE, Winter Haven, FL 33881

  Near Beautiful Lake ElbertWelcome to this well-maintained 5-bedroom, 2-bathroom home featuring a spacious open floor plan with a cozy fireplace — perfect for both relaxation and entertaining. The bright and airy layout flows seamlessly from the living area into the kitchen and dining spaces, creating a warm and inviting atmosphere throughout. Step out onto the large screened-in porch — an

  Marissa Hipp COLDWELL BANKER REALTY

  1476 Avenue F NE, Winter Haven, FL 33881
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  /34

  $435,000

  • 5 Beds
  • 3.5 Baths
  • 2,829 Sq Ft

  107 Lake Howard Dr NW, Winter Haven, FL 33880

  Welcome to this timeless 1926 brick craftsman located just steps from Lake Howard in Winter Haven. This beautifully maintained 4 bedroom, 2.5 bathroom home offers more than 2,600 sq ft of living space, hardwood floors, and the kind of character no modern build can replicate. The home features a bright great room, formal dining room, an office with access to a screened porch, and updated kitchens

  Ashley Bearden KELLER WILLIAMS REALTY SMART

  107 Lake Howard Dr NW, Winter Haven, FL 33880
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  /49

  $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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  /99

  $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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  /25

  $480,000

  • 4 Beds
  • 3 Baths
  • 1,985 Sq Ft

  1075 8th St NW, Winter Haven, FL 33881

  Income-Generating Property with Two In-Law Suites, sitting on a huge lot with a pool!! Maximize your rental income potential with this 4-bedroom, 3-bathroom property, featuring a 2-bedroom, 1-bathroom main house and two separate in-law suites, each with private entrances—perfect for long-term tenants, short-term rentals, or multi-generational living. The main house offers two spacious bedrooms, a

  Karen Corea Cuadra LPT REALTY, LLC

  1075 8th St NW, Winter Haven, FL 33881
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  /25

  $409,900 New Construction

  • 5 Beds
  • 3 Baths
  • 2,244 Sq Ft

  1774 White Elephant Loop, Winter Haven, FL 33884

  Welcome to the Spring model in Peach Crossings, a spacious five-bedroom, three-bathroom, two-story home perfectly positioned on a corner lot with no side neighbors and no front neighbors. Located right next to the community playground, this home offers both privacy and convenience for families. As you step inside, a long and welcoming foyer sets the stage for the open and thoughtfully designed

  Gayle Van Wagenen LGI REALTY- FLORIDA, LLC

  1774 White Elephant Loop, Winter Haven, FL 33884
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  /52

  $495,000

  • 4 Beds
  • 2 Baths
  • 2,756 Sq Ft

  2405 Melrose St, Winter Haven, FL 33881

  Welcome to this stunning 4-bedroom, 2-bath pool home that blends elegance, comfort, and functionality. From the moment you enter through the double doors, you’re greeted with an open floor plan and wood plank laminate flooring throughout, creating a warm and inviting atmosphere. The home features multiple living and dining spaces, including a formal living room, formal dining room (or

  Stacey Towns STACEY TOWNS REALTY LLC

  2405 Melrose St, Winter Haven, FL 33881
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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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  /31

  $485,000

  • 4 Beds
  • 3 Baths
  • 2,569 Sq Ft

  305 Hernando Rd, Winter Haven, FL 33884

  Welcome to your Dream home!! Step into this stunning residence through a spacious, light-filled foyer and prepare to be impressed by the thoughtfully, well maintained designed layout and exceptional features throughout. This home offers oversized bedrooms and a versatile bonus room—perfect for a game room, home office, or even a private in-law suite. This home has a formal living area, family

  Sherry Sapp COLDWELL BANKER REALTY

  305 Hernando Rd, Winter Haven, FL 33884
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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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  /58

  $425,000

  • 4 Beds
  • 2.5 Baths
  • 2,434 Sq Ft

  5009 Strada Dr, Winter Haven, FL 33880

  Welcome to this well-maintained Winter Haven pool home, offering over 2,400 sq ft of living space on a corner lot. This 4-bedroom, 2.5-bathroom home includes a 3-car garage, wood floors in the kitchen, foyer, and dining room, and spacious rooms with generous closet space. Upstairs, a cozy loft provides the perfect spot to unwind.Step outside to a screened and heated inground pool and spa,

  Florentino Beltran KELLER WILLIAMS ADVANTAGE 2 REALTY

  5009 Strada Dr, Winter Haven, FL 33880
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  /25

  $409,900 New Construction

  • 5 Beds
  • 3 Baths
  • 2,244 Sq Ft

  1761 White Elephant Loop, Winter Haven, FL 33884

  Welcome to the Spring model in Peach Crossings, a stunning two-story home featuring five spacious bedrooms and three bathrooms. Set on a private lot with no side or rear neighbors, this property ensures complete tranquility. An extended driveway adds convenience with plenty of parking, and the home is uniquely positioned next to a serene pond for peaceful views.Enter through a generous

  Gayle Van Wagenen LGI REALTY- FLORIDA, LLC

  1761 White Elephant Loop, Winter Haven, FL 33884
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  /20

  $499,000

  • 3 Beds
  • 2 Baths
  • 2,521 Sq Ft

  6265 Pinehurst Loop, Winter Haven, FL 33884

  Seller may consider buyer concessions if made in an offer ** Welcome to Lake Ashton, Winter Haven’s premier 55+ GUARD GATED COMMUNITY offering RESORT STYLE LIVING at its finest! BUILT IN 2021, this spacious single-story home combines modern design, efficiency, and comfort – all perfectly positioned on a beautiful GOLF COURSE LOT with sweeping views. Inside, you will be pleased to find an OPEN

  Jennifer Wemert WEMERT GROUP REALTY LLC

  6265 Pinehurst Loop, Winter Haven, FL 33884
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  /87

  $425,000

  • 3 Beds
  • 2.5 Baths
  • 2,263 Sq Ft

  239 Golf Aire Blvd, Winter Haven, FL 33884

  An exceptional opportunity to own a beautiful 3brm/2.5 bath home nestled on the 4th hole of the highly sought-after Lake Bess Country Club and Golf Course in Winter Haven. As you step inside, you are welcomed by a charming foyer featuring 14-ft ceilings that create an open and airy ambiance throughout the home. The living room, enhanced by a cozy gas fireplace, provides a perfect setting for

  Christina Ashley DALTON WADE INC

  239 Golf Aire Blvd, Winter Haven, FL 33884
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  /24

  $419,900

  • 4 Beds
  • 2.5 Baths
  • 3,055 Sq Ft

  673 Sarner Pass Way, Winter Haven, FL 33881

  Beautiful property in an oversize lot ( 15,550 sq ft , more than 1/3 of acre ) over 3000 sq ft under air, all tile on the first floor, upon entereing the home it features an office, overlooking the formal dining and living area, behind that is oversize family room and the elegant kitchen, featuring all stainless steel appliances , you are also going to find the oversize lanai in the back of the

  Consuelo Zea ZEA REALTY & ASSOCIATES

  673 Sarner Pass Way, Winter Haven, FL 33881
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  /98

  $479,900

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

  4433 Ventana Ln, Lake Wales, FL 33859

  Welcome to the next chapter of your life in beautiful Lake Ashton—Central Florida’s premier 55+ active-adult community. This immaculate 2,512 sq. ft. residence perfectly blends tasteful style, timeless elegance, and the easygoing charm of Florida living, and the CDD debt is PAID IN FULL. And the list price has been reduced by $10,000! With 3 generous bedrooms, 2 full baths, and a versatile

  Brad Kirwan GLOBAL LIFESTYLE LLC

  4433 Ventana Ln, Lake Wales, FL 33859
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  /68

  $419,000

  • 3 Beds
  • 2 Baths
  • 2,312 Sq Ft

  4497 Strathmore Dr, Lake Wales, FL 33859

  WELCOME HOME!!!!! This St. John Floor Plan has 3-Bedrooms, 2 Baths PLUS a DEN and Separate golf cart garage entrance. It combines everyday comfort and modern living with over 2,300 sq.ft. living area. Nestled in a prime, well-established Florida Retirement community, this home with CDD DEBT PAID IN FULL is located behind the guarded and secure gates of Lake Ashton. Step inside to discover a

  Lori Raath LAKE ASHTON REALTY INC.

  4497 Strathmore Dr, Lake Wales, FL 33859

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