Winter Haven, FL Homes for Sale under $300,000

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  /10

  $230,000

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

  705 Glad Rd, Winter Haven, FL 33880

  Seller is offering $5000 toward Buyer's closing costs. Not to be confused as Buyer broker fee.

  Gloria Moody

  705 Glad Rd, Winter Haven, FL 33880
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  /73

  $250,000

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

  11 Casarena Ct, Winter Haven, FL 33881

  Discover a rare opportunity to own this architecturally distinctive 2-bedroom, 2.5-bath residence located in the gated community of Casarena on the Lakes. This well-designed home offers an impressive blend of indoor and outdoor living spaces. The main level features a formal living room with a fireplace and wet bar, a dining area, a functional kitchen with breakfast bar, a guest half bath, and

  Tim Weisheyer DREAM BUILDERS REALTY

  11 Casarena Ct, Winter Haven, FL 33881
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  /28

  $224,999

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

  1904 3rd St NE, Winter Haven, FL 33881

  CONCESSIONS AVAILABLE! Welcome home to this beautifully updated 4 bed, 2 bath in the heart of Winter Haven! Inside you’ll find stylish upgrades like vinyl flooring, granite countertops, and stainless steel appliances. A brand new roof offers peace of mind, and the inviting side yard is perfect for gatherings, gardening, or simply relaxing in the Florida sun. With ~1,400 sq ft, this move-in ready

  Henry Linder XPERT REALTY GROUP

  1904 3rd St NE, Winter Haven, FL 33881
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  /39

  $270,000

  • 3 Beds
  • 2 Baths
  • 1,666 Sq Ft

  2817 Wingfoot Ct, Winter Haven, FL 33884

  Welcome to 2817 Wingfoot Ct, located in the desirable Cypresswood Golf Villas. This beautifully maintained villa sits along the 8th fairway of the prestigious Cypresswood Golf & Country Club, a guard-gated community offering both privacy and tranquility. Inside, you'll find three spacious bedrooms and two full bathrooms. The living and dining areas feature vaulted ceilings that enhance the open

  Dee Norris NEXTHOME NORRIS & COMPANY REAL

  2817 Wingfoot Ct, Winter Haven, FL 33884
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  /35

  $273,900

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

  3923 Baldwin Ln, Winter Haven, FL 33884

  WELCOME TO 3923 BALDWIN LANE, NEW ROOF 2023, NEW A/C 2025, FRESHLY PAINTED 2024. LOCATED IN THE HIGHLY SOUGHT-AFTER TRADITIONS GATED COMMUNITY IN WINTER HAVEN! THIS BEAUTIFULLY MAINTAINED HOME OFFERS THE PERFECT BLEND OF COMFORT, STYLE, AND LOW-MAINTENANCE LIVING. FEATURING SPACIOUS LIVING AREAS, A WELL-APPOINTED KITCHEN, AND A SERENE SCREENED-IN LANAI, IT'S IDEAL FOR RELAXING OR ENTERTAINING.

  Brian Reeves LPT REALTY, LLC

  3923 Baldwin Ln, Winter Haven, FL 33884
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  /39

  $200,000

  • 2 Beds
  • 1 Bath
  • 1,274 Sq Ft

  601 Avenue U NE, Winter Haven, FL 33881

  EXCELLENT INVESTMENT OPPORTUNITY IN THE HEART OF WINTER HAVEN! LOCATED AT 601 AVE U NE, THIS PROPERTY OFFERS INCREDIBLE POTENTIAL FOR RENTAL INCOME OR FUTURE DEVELOPMENT. WITH A SPACIOUS LOT AND SOLID STRUCTURE, IT'S PERFECT FOR INVESTORS LOOKING TO RENOVATE, RENT, OR FLIP. CONVENIENTLY SITUATED NEAR DOWNTOWN WINTER HAVEN, SCHOOLS, SHOPPING, AND MEDICAL FACILITIES, THIS LOCATION IS IDEAL FOR

  Brian Reeves LPT REALTY, LLC

  601 Avenue U NE, Winter Haven, FL 33881
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  /31

  $239,900

  • 2 Beds
  • 2 Baths
  • 1,368 Sq Ft

  14 Enclave Dr, Winter Haven, FL 33884

  Fresh on the market is this meticulously maintained and professionally updated 2 bedroom 2 bath villa located in the sought after "Enclave" neighborhood in Cypresswood, a gated golf community in SE Winter Haven.The open floor plan features an expansive kitchen with breakfast nook, spacious living/dining room combo, split bedrooms with ample closets, inside laundry area equipped with a washer

  Steven Smith, PA LOCKHART & ASSOCIATES INC

  14 Enclave Dr, Winter Haven, FL 33884
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  /40

  $220,000

  • 3 Beds
  • 3 Baths
  • 1,426 Sq Ft

  1858 4th St SE, Winter Haven, FL 33880

  NEW ROOF already installed september 2025, however non functional electrical panel, non functional AC so only CASH and Private HARD MONEY is available for this home. New Roof & Great Structure. With some upgrades and TLC the possibilities are endless as the enclosed carport can be expanded for additional 2 bedrooms to bring to a total 5 bedroom home Rental or for a Large Family to Enjoy. View of

  Jean Cidel SUNSTATE REALTY OF CENTRAL FL

  1858 4th St SE, Winter Haven, FL 33880
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  /46

  $234,900

  • 2 Beds
  • 2 Baths
  • 1,563 Sq Ft

  1077 Medinah Way, Winter Haven, FL 33884

  HARD TO FIND ...YET EASY TO OWN.!!! ENJOY COMING HOME TO THIS WONDERFUL COMMUNITY IN A TENNIS VILLA. IT IS A SPACIOUS END UNIT IN THE BEAUTIFUL CYPRESSWOOD GOLF AND TENNIS COMMUNITY WITH LOTS OF AMENITIES INCLUDING GATE SECURITY. CALL TO PREVIEW THIS WELL-MAINTAINED 2 BED 2 BATH CB VILLA, WITH FORMAL LIVING AND DINING AREA, SPACIOUS FLORIDA ROOM OVERLOOKING THE TENNIS COURTS AND POOL AREA, NICE

  Heidi Gravel WESTLAKE REAL ESTATE CO., INC.

  1077 Medinah Way, Winter Haven, FL 33884
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  /8

  $299,900

  • Land
  • 1.04 Acres
  • $288,365 per Acre

  1100 Eloise Loop Rd, Winter Haven, FL 33884

  PRIME COMMERCIAL LOT FOR SALE - EXCEPTIONAL OPPORTUNITY! This strategically located commercial lot is ideal for retail, office, industrial, multi-family or mixed use development. Easy access and close proximity to residential neighborhoods, this buildable one acre parcel offers unmatched versatility and growth potential. AS A BONUS, it has been cleared, engineered and permitted for building one

  Rhonda Martin SIGNATURE PROPERTIES OF CENTRAL FLORIDA LLC

  1100 Eloise Loop Rd, Winter Haven, FL 33884
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  /37

  $285,000

  • 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 and 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

  Dee Norris NEXTHOME NORRIS & COMPANY REAL

  441 San Jose Dr, Winter Haven, FL 33884
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  /21

  $240,000

  • 2 Beds
  • 1.5 Baths
  • 1,043 Sq Ft

  3208 Timberline Rd, Winter Haven, FL 33880

  MOVE-IN READY & COMPLETELY REMODELED!This stunning home features a bright, open layout with modern shiplap accents, skylights, and a cozy fireplace. Enjoy NEW luxury vinyl plank flooring, a chef’s kitchen with soft-close cabinets, quartz countertops, and stainless steel appliances. The owner’s suite includes a walk-in closet and private bath. Both bathrooms have been fully updated. Plus,

  Carolina Cruz Acedo LPT REALTY, LLC

  3208 Timberline Rd, Winter Haven, FL 33880
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  /31

  $294,000

  • 2 Beds
  • 2 Baths
  • 1,691 Sq Ft

  1452 Grand Cayman Cir, Winter Haven, FL 33884

  PRICE REDUCTION!! Discover this stunning lakefront gem on Lake Dexter—a peaceful 166-acre lake in southeast Winter Haven, accessible only through private community ramps. Perfect for fishing, waterskiing, or simply cruising, Lake Dexter has something for everyone.Located in the highly sought-after Lake Dexter Moorings Community, residents enjoy a sparkling community pool and private boat

  Tomi Miller-Troupe COLDWELL BANKER REALTY

  1452 Grand Cayman Cir, Winter Haven, FL 33884
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  /50

  $250,000

  • 3 Beds
  • 2 Baths
  • 1,144 Sq Ft

  657 Avenue C SW, Winter Haven, FL 33880

  Discover this beautifully 3/2 home with a brand new roof 2022 in serene neighborhood .With no HOA or CDD ,this property offers peace of mind and potential for a primary residence ,rental investment ,or Airbnb .Currently rented for $1350 per month .The open concept living space is filled with natural light .The kitchen features a glass cooktop range ,ample counter space .Each generously sized

  Hala Saleh LoKation

  657 Avenue C SW, Winter Haven, FL 33880
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  /52

  $217,900 Open Sat 11AM - 2PM

  • 2 Beds
  • 2.5 Baths
  • 1,281 Sq Ft

  2348 Isle Royale Ct SE, Winter Haven, FL 33880

  BIG PRICE REDUCTION – $7,000! Recently Fully Renovated Townhouse – Move-In Ready! Seller offering $4,000 credit toward buyer’s closing costs or interest rate buydown. Don’t miss your chance to own this completely remodeled 2-bedroom, 2.5-bathroom townhouse in Park Lake, now available at an unbeatable price! This home has been beautifully updated from top to bottom, offering modern style and

  Fatma Higdon HIGDON HOMES REALTY LLC

  2348 Isle Royale Ct SE, Winter Haven, FL 33880
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  /15

  $250,000

  • 3 Beds
  • 2 Baths
  • 1,329 Sq Ft

  123 Osprey Heights Dr, Winter Haven, FL 33880

  Beautiful 3BR/2BA home in a gated community of Osprey Heights. All floors are covered with wood laminate. The Solar system is paid off and included in the price of the home with no extra payment.

  Othner Stfleurose OSF REAL ESTATE SERVICE

  123 Osprey Heights Dr, Winter Haven, FL 33880
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  /44

  $225,000

  • 2 Beds
  • 2 Baths
  • 1,231 Sq Ft

  1561 Vienna Square Dr, Winter Haven, FL 33884

  R E D U C E D ... YOU'LL LOVE THIS MAINTENANCE FREE LIFESTYLE IN DESIREABLE VIENNA SQUARE , LOCATED IN WINTER HAVEN. THIS VILLA IS MOVE IN READY. THIS 2BR-2BA VILLA OFFERS AN OPEN GREAT ROOM DESIGN WITH SPLIT BEDROOMS. THE MASTER ENSUITE HAS WALK IN CLOSET WITH STEP IN SHOWER FOR CONVENIENCE. THE 2ND BEDROOM OFF FRONT ENTRANCE OF HOME HAS AN ADJOINING BATH WITH TUB AND SHOWER. DON'T WAIT, THIS

  Glenda Pruitt FLORIDA HOME CHOICE REALTY

  1561 Vienna Square Dr, Winter Haven, FL 33884
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  /51

  $295,000

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

  912 Avenue T SE, Winter Haven, FL 33880

  Location, Location! This charming 3-bedroom, 2-bath home, large living room and a huge family room ( could be a 4th bedroom) is situated in the vibrant and growing Winter Haven area. Conveniently close toLEGOLAND, shopping centers, hospitals, and medical offices, it offers both comfort and accessibility. Solar Panels( worth $44K) will be paid by seller at closing ! This home has a nice back

  Lucy Martinez CENTURY 21 WOLF'S CROSSING REALTY

  912 Avenue T SE, Winter Haven, FL 33880
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  /29

  $299,000

  • 3 Beds
  • 2 Baths
  • 1,361 Sq Ft

  751 Avenue B SW, Winter Haven, FL 33880

  This home is waiting just for you! Don’t lose the opportunity to come and see this remodeled house. Walking distance to Lake Howard where you can enjoy your leisure time. House is located just a few minutes from Publix, Walmart, CVS, and Winter Haven Hospital.

  Emina Vasquez CENTURY 21 WOLF'S CROSSING REALTY

  751 Avenue B SW, Winter Haven, FL 33880
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  /24

  $250,000

  • 4 Beds
  • 2 Baths
  • 1,416 Sq Ft

  1027 31st St NW, Winter Haven, FL 33881

  Welcome to a meticulously maintained 4-bedroom, 2-bathroom residence spanning 1416 sqft. Situated on a .32-acre lot in a serene neighborhood, this property offers a harmonious blend of comfort and convenience.Step into an environment that exudes a sense of home from the moment you enter, combining warmth with a straightforward and welcoming ambiance. The property features spacious room

  Jomar Gonzalez LA ROSA REALTY LLC

  1027 31st St NW, Winter Haven, FL 33881
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  /82

  $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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  /15

  $250,000

  • Land
  • 0.79 Acre
  • $316,456 per Acre

  0 Dundee Rd Unit P4924283, Winter Haven, FL 33881

  Just Reduced! Stop by and check on this vacant lot in an area that is growing with new expanded roads. More than 3/4-acre zone C3 lot on Dundee Rd Hwy 542 with approx. 143 feet of road frontage. Ideally positioned in front of the 16th St intersection. The Department of Transportation finished up the Dundee Rd expansion improvements further to the East. This project has given this lot multiple

  Michael Brenner CENTURY 21 MYERS REALTY

  0 Dundee Rd Unit P4924283, Winter Haven, FL 33881
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  /2

  $265,000

  • 3 Beds
  • 2 Baths
  • 1,432 Sq Ft

  961 Harold Pass, Winter Haven, FL 33884

  BEAUTIFUL home built in 2025, featuring 3 bedrooms, 2 baths, and an open living area. The kitchen boasts an open and airy design, with aspacious center island perfect for entertaining, complemented by new stainless-steel appliances,and a walk-in pantry. The dining room is perfectly placed near the kitchen, providing the ideal setting for meals and celebrations of any kind. The family room

  Marian Capriles Garcia LPT REALTY, LLC

  961 Harold Pass, Winter Haven, FL 33884
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  /2

  $285,000

  • 3 Beds
  • 2 Baths
  • 1,265 Sq Ft

  200 Black Skimmer Ln, Winter Haven, FL 33880

  PRE-FORECLOSURE - 3 Bedroom/2 Bath Home in a gated community. This home is only 4 years old, but it needs a lot of cosmetic work. The Buyers may assume the current mortgage at 3% interest.

  Linda Andre COLDWELL BANKER REALTY

  200 Black Skimmer Ln, Winter Haven, FL 33880
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  /2

  $225,000

  • Land
  • 0.29 Acre
  • $775,862 per Acre

  0 Spirit Lake Rd Unit MFRP4934429, Winter Haven, FL 33880

  **Prime Commercial Lot for Sale – Spirit Lake Road, Winter Haven, FL****Location, Location, Location!**This is a rare opportunity to own a prime commercial lot in one of Winter Haven's highest-traffic areas. Located directly on Spirit Lake Road, this vacant parcel is surrounded by thriving businesses, making it an ideal spot for your next commercial venture. With McDonald's as

  James Barris EXP REALTY LLC

  0 Spirit Lake Rd Unit MFRP4934429, Winter Haven, FL 33880
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  /2

  $238,000

  • Land
  • 0.79 Acre
  • $301,266 per Acre

  0 3rd St SW, Winter Haven, FL 33880

  Amazing commercial property ready for a business. Backs up to CSX railroad tracks. Property is in the Elouise CRA so tax incentives are available.

  Anthony Medina KELLER WILLIAMS REALTY SMART 1

  0 3rd St SW, Winter Haven, FL 33880
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  /35

  $284,840 New Construction

  • 3 Beds
  • 2 Baths
  • 1,328 Sq Ft

  2787 Adeline Ave, Winter Haven, FL 33881

  The property is located at 2787 Adeline Ave WINTER HAVEN FL 33881 priced at 284840, the square foot and stories are 1328, 1.The number of bath is 2, halfbath is 0 there are 3 bedrooms and 2 garages. For more details please, call or email.

  D.R. Horton Builder

  2787 Adeline Ave, Winter Haven, FL 33881
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  /27

  $282,090 New Construction

  • 4 Beds
  • 2 Baths
  • 1,665 Sq Ft

  4952 Kaia Ave, Winter Haven, FL 33884

  The property is located at 4952 Kaia Avenue WINTER HAVEN FL 33884 priced at 282090, the square foot and stories are 1665, 1.The number of bath is 2, halfbath is 0 there are 4 bedrooms and 2 garages. For more details please, call or email.

  D.R. Horton Builder

  4952 Kaia Ave, Winter Haven, FL 33884
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  /27

  $292,740 New Construction

  • 4 Beds
  • 2 Baths
  • 1,498 Sq Ft

  2779 Adeline Ave, Winter Haven, FL 33881

  The property is located at 2779 Adeline Ave WINTER HAVEN FL 33881 priced at 292740, the square foot and stories are 1498, 1.The number of bath is 2, halfbath is 0 there are 4 bedrooms and 2 garages. For more details please, call or email.

  D.R. Horton Builder

  2779 Adeline Ave, Winter Haven, FL 33881
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  /27

  $286,840 New Construction

  • 4 Beds
  • 2 Baths
  • 1,498 Sq Ft

  2791 Adeline Ave, Winter Haven, FL 33881

  The property is located at 2791 Adeline Ave WINTER HAVEN FL 33881 priced at 286840, the square foot and stories are 1498, 1.The number of bath is 2, halfbath is 0 there are 4 bedrooms and 2 garages. For more details please, call or email.

  D.R. Horton Builder

  2791 Adeline Ave, Winter Haven, FL 33881
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  /28

  $282,090 New Construction

  • 4 Beds
  • 2 Baths
  • 1,665 Sq Ft

  4048 Giorgio Dr, Winter Haven, FL 33884

  The property is located at 4048 Giorgio Drive WINTER HAVEN FL 33884 priced at 284990, the square foot and stories are 1665, 1.The number of bath is 2, halfbath is 0 there are 4 bedrooms and 2 garages. For more details please, call or email.

  D.R. Horton Builder

  4048 Giorgio Dr, Winter Haven, FL 33884
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  /27

  $280,590 New Construction

  • 4 Beds
  • 2 Baths
  • 1,665 Sq Ft

  4663 Ostero St, Winter Haven, FL 33884

  The property is located at 4663 Ostero Street WINTER HAVEN FL 33884 priced at 283490, the square foot and stories are 1665, 1.The number of bath is 2, halfbath is 0 there are 4 bedrooms and 2 garages. For more details please, call or email.

  D.R. Horton Builder

  4663 Ostero St, Winter Haven, FL 33884
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  /27

  $280,590 New Construction

  • 4 Beds
  • 2 Baths
  • 1,665 Sq Ft

  4160 Giorgio Dr, Winter Haven, FL 33884

  The property is located at 4160 Giorgio Drive WINTER HAVEN FL 33884 priced at 283490, the square foot and stories are 1665, 1.The number of bath is 2, halfbath is 0 there are 4 bedrooms and 2 garages. For more details please, call or email.

  D.R. Horton Builder

  4160 Giorgio Dr, Winter Haven, FL 33884
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  /35

  $280,840 New Construction

  • 3 Beds
  • 2 Baths
  • 1,328 Sq Ft

  2775 Adeline Ave, Winter Haven, FL 33881

  The property is located at 2775 Adeline Ave WINTER HAVEN FL 33881 priced at 280840, the square foot and stories are 1328, 1.The number of bath is 2, halfbath is 0 there are 3 bedrooms and 2 garages. For more details please, call or email.

  D.R. Horton Builder

  2775 Adeline Ave, Winter Haven, FL 33881
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  /2

  $288,990 New Construction

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

  4521 Faith Dr, Lake Wales, FL 33859

  The property is located at 4521 Faith Drive LAKE WALES FL 33859 priced at 288990, 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

  4521 Faith Dr, Lake Wales, FL 33859
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  /41

  $299,990 New Construction

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

  2747 San Marco Way, Winter Haven, FL 33884

  This thoughtfully designed single-story home offers 3 bedrooms, 2 bathrooms, and 1,680 square feet of comfortable living space with a 2-car garage. The open layout centers around a spacious great room that flows into the dining area and kitchen, creating an ideal space for everyday living and entertaining. The kitchen features a center island, pantry, and dedicated refrigerator space. Sliding

  Maronda Homes Builder

  2747 San Marco Way, Winter Haven, FL 33884
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  /25

  $272,990 New Construction

  • 3 Beds
  • 2 Baths
  • 1,504 Sq Ft

  5561 Taverna Loop, Winter Haven, FL 33884

  Under Construction. The Allex II is one of our one-story floorplans featured in Villamar in Winter Haven, Florida. With 2 exteriors to choose from, the Allex is sure to turn heads. Inside this 3-bedroom, 2-bathroom home, you’ll find 1,504 square feet of comfortable living. The living area is an open concept, where your kitchen, living, and dining areas blend seamlessly into a space perfect for

  Paul King DR HORTON REALTY OF CENTRAL FLORIDA LLC

  5561 Taverna Loop, Winter Haven, FL 33884
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  /16

  $299,490 New Construction

  • 5 Beds
  • 2 Baths
  • 2,112 Sq Ft

  6449 Domizio Dr, Winter Haven, FL 33884

  The first floor of this new two-story home is host to an open-concept layout that combines the kitchen with the living and dining areas, and an outdoor patio is easily reached off the main living space. Upstairs, five bedrooms surround a versatile loft, including the luxe owner’s suite, complete with a generous walk-in closet and en-suite bathroom.

  Lennar Builder

  6449 Domizio Dr, Winter Haven, FL 33884
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  /21

  $299,999 New Construction

  • 3 Beds
  • 2 Baths
  • 1,615 Sq Ft

  5397 San Pietro Dr, Winter Haven, FL 33884

  Feel at home with the Magenta, a single-story home with 3 bedrooms, 2 bathrooms, and a 2-car garage. This layout is a true gem, seamlessly blending modern comfort with Florida charm. Open concept living dazzles with luxury vinyl plank flooring throughout the main living areas. The kitchen, featuring quartz countertops, new stainless-steel appliances and ample storage overlooks the dining and

  Casa Fresca Homes Builder

  5397 San Pietro Dr, Winter Haven, FL 33884
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  /21

  $299,999 New Construction

  • 3 Beds
  • 2 Baths
  • 1,615 Sq Ft

  6010 Navona Way, Winter Haven, FL 33884

  Feel at home with the Magenta, a single-story home with 3 bedrooms, 2 bathrooms, and a 2-car garage. This layout is a true gem, seamlessly blending modern comfort with Florida charm. Open concept living dazzles with luxury vinyl plank flooring throughout the main living areas. The kitchen, featuring quartz countertops, new stainless-steel appliances and ample storage overlooks the dining and

  Casa Fresca Homes Builder

  6010 Navona Way, Winter Haven, FL 33884

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