5-Bedroom Homes for Sale in Winter Haven, FL

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  /23

  $750,000

  • 11 Beds
  • 7 Baths
  • 4,518 Sq Ft

  662 24th St NW, Winter Haven, FL 33880

  Investor Special! Rare opportunity to acquire a 7-unit, duplex-style community offering excellent potential and cash-flow possibilities. The property features two duplex buildings, each consisting of two 2-bedroom, 1-bathroom units, plus one triplex building with three 1-bedroom, 1-bathroom units. All units require updating, providing an outstanding value-add opportunity to significantly increase

  Chris Renfro KELLER WILLIAMS REALTY SMART

  662 24th St NW, Winter Haven, FL 33880
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  /49

  $639,000

  • 5 Beds
  • 3 Baths
  • 3,680 Sq Ft

  4225 Shadow Wood Ct, Winter Haven, FL 33880

  No HOA or CDD fees! This expansive 3,600 sq. ft. residence is perfectly designed for a multi generational family with a mother in-law suite! With 5 bedrooms and 3 bathrooms, this home offers ample space for everyone, including a huge family room looking out on the back deck and pool area! There is also a large bedroom with it’s own full bath that would make a great mother in-law suite! Key

  Gary Peach S & D REAL ESTATE SERVICE LLC

  4225 Shadow Wood Ct, Winter Haven, FL 33880
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  /100

  $1,490,000

  • 8 Beds
  • 7 Baths
  • 7,810 Sq Ft

  3001 Crystal Beach Rd, Winter Haven, FL 33880

  Welcome to your dream home at 3001 Crystal Beach Road in Winter Haven, FL—a masterpiece of luxury and sophistication. This breathtaking 8-bedroom, 7-bathroom estate redefines opulence, offering unparalleled features and amenities designed for both grand entertaining and everyday indulgence.As you step into this expansive residence, you'll be captivated by the soaring high ceilings,

  David Small KELLER WILLIAMS REALTY SMART 1

  3001 Crystal Beach Rd, Winter Haven, FL 33880
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  /38

  $1,650,000

  • 8 Beds
  • 7 Baths
  • 5,194 Sq Ft

  1957 Rifle Range Rd, Winter Haven, FL 33880

  One or more photo(s) has been virtually staged. Nestled on 14 acres of serene land, this expansive property offers a rare combination of space, privacy, and convenience, with easy access to downtown Winter Haven and Legoland. The main residence features a spacious split floor plan with 3 bedrooms and 2 bathrooms. Vaulted ceilings and an open layout create an airy, inviting atmosphere, while the

  David Small KELLER WILLIAMS REALTY SMART 1

  1957 Rifle Range Rd, Winter Haven, FL 33880
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  /48

  $1,650,000

  • 8 Beds
  • 6 Baths
  • 5,194 Sq Ft

  1957 Rifle Range Rd, Winter Haven, FL 33880

  One or more photo(s) has been virtually staged. Nestled on 14 acres of serene land, this expansive property offers a rare combination of space, privacy, and convenience, with easy access to downtown Winter Haven and Legoland. The main residence features a spacious split floor plan with 3 bedrooms and 2 bathrooms. Vaulted ceilings and an open layout create an airy, inviting atmosphere, while the

  David Small KELLER WILLIAMS REALTY SMART 1

  1957 Rifle Range Rd, Winter Haven, FL 33880
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  /89

  $695,000

  • 9 Beds
  • 4 Baths
  • 3,446 Sq Ft

  121 Bates Ave SE, Winter Haven, FL 33880

  This rare offering consists of three parcels with a mix of C-3 commercial and R-3 residential zoning, presenting an exceptional investment opportunity on 1st Street South in the heart of Winter Haven. Located on a bustling four-lane road with 30,000 cars passing daily, these properties provide unparalleled exposure for businesses. The first two parcels, located at 212 1st St S and 210 1st St S,

  Hank Petty KELLER WILLIAMS REALTY SMART 1

  121 Bates Ave SE, Winter Haven, FL 33880
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  /86

  $370,000

  • 5 Beds
  • 3 Baths
  • 2,601 Sq Ft

  821 Sun Burst Rd, Winter Haven, FL 33880

  POLK COUNTY OFFERING UP TO $7,500 OF DOWNPAYMENT ASSISTANCE!!! HOME IS MINUTES FROM LEGOLAND!! This modern 5 bedroom, 3 bathroom home, just two years old, is perfect for those seeking both comfort and functionality. Located in a peaceful cul-de-sac, the home features an inviting open floor plan that seamlessly connects the living room, kitchen and dining area. The kitchen is spacious, offering

  Gigi Sevilla WYNNMORE REALTY LLC

  821 Sun Burst Rd, Winter Haven, FL 33880
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  /81

  $1,150,000

  • 5 Beds
  • 4 Baths
  • 4,591 Sq Ft

  121 E Lake Summit Dr, Winter Haven, FL 33884

  ***The seller agrees to pay off the solar panels at closing.*** Step into a world of lakeside luxury with this majestic red-brick residence, where modern updates meet timeless elegance. Enter through the brick-paved tropical walkways and courtyard, accented by charming coach house light fixtures, leading you to a spacious 5-bed, 4-bath home. Recently enhanced with a new AC system installed just 6

  David Small KELLER WILLIAMS REALTY SMART 1

  121 E Lake Summit Dr, Winter Haven, FL 33884
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  /48

  $1,350,000

  • 5 Beds
  • 4.5 Baths
  • 4,513 Sq Ft

  1441 S Lake Roy Dr, Winter Haven, FL 33884

  CHAIN OF LAKES!!! POOL!!! 5 BEDROOMS AND 4.5 BATHROOMS!!! This is the listing you have been waiting for - look no further. This incredible residence is situated on over half an acre of maturely landscaped waterfront property and has a remarkable list of features and finishes. The sprawling floor plan encompasses 4,513SqFt of LIVING AREA with 5 generous bedrooms and 4.5 beautiful baths; 3.5 of

  Catherine Kluytenaar THE K TEAM REAL ESTATE SERVICES LLC

  1441 S Lake Roy Dr, Winter Haven, FL 33884
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  /73

  $1,699,900

  • 5 Beds
  • 8 Baths
  • 8,505 Sq Ft

  999 Oleander Dr SE, Winter Haven, FL 33880

  Significant Price Adjustment on this Fantastic, One of a kind, lake front estate on 3.22 acres: Architectural designed by Architect Frances R Hoffman (Student of Frank Lloyd Wright). Very Contemporary style offers a flowing floor plan which encompasses 8485 Square Feet of luxury living offering exceptional appointments. Specialty ceilings, plantation shutters, Dupioni silk drapes and solid wood

  Rick Hemenway CROSBY & ASSOCIATES, INC.

  999 Oleander Dr SE, Winter Haven, FL 33880
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  /28

  $1,150,000

  • 6 Beds
  • 5.5 Baths
  • 6,100 Sq Ft

  1200 W Lake Otis Dr SE, Winter Haven, FL 33880

  THIS PROPERTY WAS ORIGINALLY 2 HOMES THAT WERE CO-JOINED. THE CURRENT OWNER HAS RECREATED TWO FULLY SEPARATE LIVING SPACES. OWNER LIVES IN ONE SIDE AND HAS A VERY SUCCESSFUL AIRBNB ON THE OTHER SIDE. THIS IS A UNIQUE OPPORTUNITY FOR A LARGE FAMILY, EXTENDED FAMILY WITH IN-LAWS, OR THOSE LOOKING FOR A STEADY STREAM OF SUPPLEMENTAL INCOME.BEAUTIFUL LAKEFRONT POOL HOME WITH EXPANSIVE VIEWS.

  Caspian Collany COLLANY PROPERTIES

  1200 W Lake Otis Dr SE, Winter Haven, FL 33880
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  /2

  $369,127

  • 8 Beds
  • 6 Baths
  • 3,304 Sq Ft

  2007 40th St NW, Winter Haven, FL 33881

  MULTI-FAMILY SPECIAL! THIS WILL NOT LAST. 8 BEDROOMS AND 6 BATHS.1 BLOCK SINGLE FAMILY HOME, 2/12 MOVIL HOMES 2/2 AND 3/21 ADDITIONAL STUDIO 1/1ALL INCLUDED IN ONE PRICE.

  Ada Molina RE/MAX REALTEC GROUP

  2007 40th St NW, Winter Haven, FL 33881
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  /27

  $358,490 New Construction

  • 5 Beds
  • 3 Baths
  • 2,077 Sq Ft

  4407 Blackwell Ave, Lake Wales, FL 33859

  Under Construction. "Welcome to the Lakeside, one of our one-story floorplans featured in our Annabelle in Lake Wales, Florida. Take your pick between two artfully designed exteriors.Inside this beautiful 5 bedroom, 3 bathroom home, you'll find 2,077 square feet of comfortable living. The living area is an open concept, where your kitchen, living, and dining areas blend seamlessly into a

  Paul King DR HORTON REALTY OF CENTRAL FLORIDA LLC

  4407 Blackwell Ave, Lake Wales, FL 33859
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  /26

  $353,490 New Construction

  • 5 Beds
  • 3 Baths
  • 2,077 Sq Ft

  4415 Blackwell Ave, Lake Wales, FL 33859

  Under Construction. "Welcome to the Lakeside, one of our one-story floorplans featured in our Annabelle in Lake Wales, Florida. Take your pick between two artfully designed exteriors.Inside this beautiful 5 bedroom, 3 bathroom home, you'll find 2,077 square feet of comfortable living. The living area is an open concept, where your kitchen, living, and dining areas blend seamlessly into a

  Paul King DR HORTON REALTY OF CENTRAL FLORIDA LLC

  4415 Blackwell Ave, Lake Wales, FL 33859
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  /24

  $331,990 New Construction

  • 5 Beds
  • 2.5 Baths
  • 2,326 Sq Ft

  1918 Sarah St, Winter Haven, FL 33884

  This two-story home highlights a modern open layout, seamlessly integrating a first-floor kitchen with a central island, a dining room and a welcoming family room with patio access. On the same level is a private owner's suite with an attached bathroom. Situated upstairs is a versatile loft for additional shared living space and four secondary bedrooms to provide restful retreats to family

  Lennar

  Georgia, Winter Haven, FL 33884
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  /25

  $364,990 New Construction

  • 5 Beds
  • 3 Baths
  • 2,691 Sq Ft

  2779 San Marco Way, Winter Haven, FL 33884

  READY NOW! Discover the perfect blend of modern convenience and timeless design in The Springfield, a beautifully crafted residence located in the sought-after Villamar community—part of our Heritage Collection. This two-story home offers 2,691 square feet of thoughtfully planned living space, blending classic charm with contemporary comfort.Step into a welcoming foyer that sets the tone

  Charles Pennant NEW HOME STAR FLORIDA LLC

  2779 San Marco Way, Winter Haven, FL 33884
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  /26

  $330,990 New Construction

  • 5 Beds
  • 3 Baths
  • 2,447 Sq Ft

  4944 Kaia Ave, Winter Haven, FL 33884

  Under Construction. "The Robie is a two-story floorplan featured in Villamar in Winter Haven, Florida. With 2 exteriors to choose from, the Robie is sure to turn heads. Inside this inviting 5-bedroom, 3-bathroom home, you’ll find 2,447 square feet of comfortable living. This impressive all concrete block construction, two-story plan features a versatile floorplan to fit your needs. A

  Paul King DR HORTON REALTY OF CENTRAL FLORIDA LLC

  4944 Kaia Ave, Winter Haven, FL 33884
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  /36

  $330,990 New Construction

  • 6 Beds
  • 3 Baths
  • 2,463 Sq Ft

  2220 Chris Dr, Winter Haven, FL 33884

  One or more photo(s) has been virtually staged. Under Construction. BEAUTIFUL CORNER LOT!! This new two-story home boasts a modern layout with an open-concept floorplan consisting of a stylish kitchen, dining room and family room on the first floor. A convenient bedroom is located toward the back of the home, perfect as a guest suite or home office. Five additional bedrooms can be found upstairs,

  Ben Goldstein LENNAR REALTY

  2220 Chris Dr, Winter Haven, FL 33884
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  /21

  $375,686 New Construction

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

  5159 Kinsley Dr, Lake Wales, FL 33859

  Under Construction. Welcome to this notable Tourmaline home, ready for quick move-in! Included features: a covered entry; a smartly planned kitchen offering white 42" cabinets, stainless-steel appliances, a sizable island, and an adjacent dining area; an impressive great room; a main-floor bedroom and full bath; a spacious loft; a lavish primary suite showcasing an immense walk-in closet and a

  Stephanie Morales THE REALTY EXPERIENCE POWERED BY LRR

  5159 Kinsley Dr, Lake Wales, FL 33859
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  /47

  $385,000 New Construction

  • 5 Beds
  • 2.5 Baths
  • 2,215 Sq Ft

  934 Cattleman St, Winter Haven, FL 33884

  Stunning 5BR/2.5BA single family home on an oversized lot in the sought-after Inman Groves community. Move-in-ready home offers 2,215sq. ft. of thoughtfully designed living space with high ceilings, tile/carpet floors, and an open-concept layout. The kitchen features a spacious island and flows into the expansive family room. Upstairs, the owner’s suite includes a large walk-in closet and

  Cristina de Oliveira Miami New Realty

  934 Cattleman St, Winter Haven, FL 33884
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  /16

  $375,000 New Construction

  • 5 Beds
  • 2.5 Baths
  • 2,254 Sq Ft

  930 Cattleman St, Winter Haven, FL 33884

  Welcome to 930 Cattleman St, located in the charming community of Inman Groves in Winter Haven, FL. This spacious Boston model by Lennar offers an ideal blend of comfort, functionality, and modern living.Boasting 5 generously sized bedrooms and 2.5 baths, this two-story home is perfect for families seeking space to grow or investors looking for strong rental potential. The thoughtfully

  Carlos Lopez Cadena EXP REALTY LLC

  930 Cattleman St, Winter Haven, FL 33884
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  /24

  $301,890 New Construction

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

  2223 Chris Dr, Winter Haven, FL 33884

  One or more photo(s) has been virtually staged. Under Construction. The first floor of the stunning Edison 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

  Ben Goldstein LENNAR REALTY

  2223 Chris Dr, Winter Haven, FL 33884
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  /26

  $330,990 New Construction

  • 5 Beds
  • 3 Baths
  • 2,447 Sq Ft

  4912 Kaia Ave, Winter Haven, FL 33884

  Under Construction. "The Robie is a two-story floorplan featured in Villamar in Winter Haven, Florida. With 2 exteriors to choose from, the Robie is sure to turn heads. Inside this inviting 5-bedroom, 3-bathroom home, you’ll find 2,447 square feet of comfortable living. This impressive all concrete block construction, two-story plan features a versatile floorplan to fit your needs. A

  Paul King DR HORTON REALTY OF CENTRAL FLORIDA LLC

  4912 Kaia Ave, Winter Haven, FL 33884
• 

  

  /26

  $325,990 New Construction

  • 5 Beds
  • 3 Baths
  • 2,447 Sq Ft

  4908 Kaia Ave, Winter Haven, FL 33884

  Under Construction. "The Robie is a two-story floorplan featured in Villamar in Winter Haven, Florida. With 2 exteriors to choose from, the Robie is sure to turn heads. Inside this inviting 5-bedroom, 3-bathroom home, you’ll find 2,447 square feet of comfortable living. This impressive all concrete block construction, two-story plan features a versatile floorplan to fit your needs. A

  Paul King DR HORTON REALTY OF CENTRAL FLORIDA LLC

  4908 Kaia Ave, Winter Haven, FL 33884
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  /25

  $331,990 New Construction

  • 5 Beds
  • 2.5 Baths
  • 2,326 Sq Ft

  1918 Sarah Ln, Winter Haven, FL 33884

  One or more photo(s) has been virtually staged. Under Construction. This two-story Georgia will definitely be on your mind... This beauty highlights a modern open layout, seamlessly integrating a first-floor kitchen with a central island, a dining room and a welcoming family room with patio access. On the same level is a private owner's suite with an attached bathroom. Situated upstairs is a

  Ben Goldstein LENNAR REALTY

  1918 Sarah Ln, Winter Haven, FL 33884
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  /26

  $330,990 Open Fri 10AM - 6PM

  • 5 Beds
  • 3 Baths
  • 2,447 Sq Ft

  3487 Costello Cir, Winter Haven, FL 33884

  Under Construction. "The Robie is a two-story floorplan featured in Villamar in Winter Haven, Florida. With 2 exteriors to choose from, the Robie is sure to turn heads. Inside this inviting 5-bedroom, 3-bathroom home, you’ll find 2,447 square feet of comfortable living. This impressive all concrete block construction, two-story plan features a versatile floorplan to fit your needs. A

  Paul King DR HORTON REALTY OF CENTRAL FLORIDA LLC

  3487 Costello Cir, Winter Haven, FL 33884
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  /24

  $331,990 New Construction

  • 5 Beds
  • 2.5 Baths
  • 2,326 Sq Ft

  1807 Teagan Ln, Winter Haven, FL 33884

  This two-story home highlights a modern open layout, seamlessly integrating a first-floor kitchen with a central island, a dining room and a welcoming family room with patio access. On the same level is a private owner's suite with an attached bathroom. Situated upstairs is a versatile loft for additional shared living space and four secondary bedrooms to provide restful retreats to family

  Lennar

  Georgia, Winter Haven, FL 33884
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  /19

  $380,190 New Construction

  • 5 Beds
  • 3 Baths
  • 2,451 Sq Ft

  Eclipse, Winter Haven, FL 33884

  The first floor of this two-story home shares an open layout between the kitchen, dining area and family room for easy entertaining with access to the patio. A secondary bedroom on the first floor can easily be converted to a guest room or home office. Upstairs is a versatile loft that serves as an additional shared living space, along with three secondary bedrooms and a luxe owner's suite

  Lennar

  Eclipse, Winter Haven, FL 33884
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  /26

  $361,990 New Construction

  • 5 Beds
  • 2.5 Baths
  • 2,326 Sq Ft

  Georgia, Winter Haven, FL 33884

  This two-story home highlights a modern open layout, seamlessly integrating a first-floor kitchen with a central island, a dining room and a welcoming family room with patio access. On the same level is a private owner's suite with an attached bathroom. Situated upstairs is a versatile loft for additional shared living space and four secondary bedrooms to provide restful retreats to family

  Lennar

  Georgia, Winter Haven, FL 33884
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  /31

  $299,999 Open Sat 11AM - 4PM

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

  1946 Sarah St, Winter Haven, FL 33884

  One or more photo(s) has been virtually staged. Under Construction. The first floor of the stunning Edison 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

  Ben Goldstein LENNAR REALTY

  1946 Sarah St, Winter Haven, FL 33884
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  /2

  $364,999 New Construction

  • 5 Beds
  • 3 Baths
  • 2,850 Sq Ft

  5151 Kinsley Dr, Lake Wales, FL 33859

  Discover this beautiful Tourmaline home, ready for quick move-in! Included features: an inviting covered entry; a main-floor bedroom and bath; a generous great room; a well-appointed kitchen showcasing 42" cabinets, quartz countertops, a center island, and an adjacent dining area; a spacious loft; an elegant primary suite boasting an oversized walk-in closet and a private bath; two additional

  Richmond American Homes

  Tourmaline, Lake Wales, FL 33859
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  /2

  $379,999 New Construction

  • 5 Beds
  • 3 Baths
  • 2,850 Sq Ft

  5155 Kinsley Dr, Lake Wales, FL 33859

  Discover this must-see Moonstone home. Included features: a charming covered entry; a well-appointed kitchen offering white cabinets, quartz countertops, a walk-in pantry, a center island and an adjacent dining area; a spacious great room; a lavish primary suite showcasing a generous walk-in closet and a private bath with double sinks; a convenient laundry; a mudroom and a covered patio.

  Richmond American Homes

  Moonstone, Lake Wales, FL 33859
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  /2

  $368,490 Open Fri 10AM - 6PM

  • 5 Beds
  • 3 Baths
  • 2,077 Sq Ft

  2530 Sage Valley Way, Winter Haven, FL 33884

  Under Construction. Find everything you need in Harmony on Lake Eloise! Located just minutes from world class theme parks and attractions, Harmony on Lake Eloise is the perfect community to call home with its beautiful Florida lifestyle and amenities. This community boasts stunning home sites. You'll enjoy the sparkling local lakes practically in your backyard and the best local restaurants and

  Paul King DR HORTON REALTY OF CENTRAL FLORIDA LLC

  2530 Sage Valley Way, Winter Haven, FL 33884
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  /4

  $5,000

  • 5 Beds
  • 3 Baths
  • 2,616 Sq Ft

  3228 Country Walk Club Cir, Winter Haven, FL 33881

  Foreclosure Auction Ends August 04, 2025 at 10:00 AM EST. Discover this well-maintained 5-bedroom, 3-bathroom single-family home located in the desirable Country Walk Estates community of Winter Haven. The list price is the opening bid for the online auction. Sold As-is with Clear Title. Explore more details and submit your bid through the Federa Home App.

  Jamie Boone Jamie L Boone LLC

  3228 Country Walk Club Cir, Winter Haven, FL 33881
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  /35

  $294,000

  • 5 Beds
  • 3 Baths
  • 2,527 Sq Ft

  235 Hibiscus St, Winter Haven, FL 33881

  Discover a rare opportunity for instant equity with this spacious 5-bedroom, 3-bathroom home in Winter Haven. Ideal for multi-generational living or growing households, the first floor features an open layout plus a bedroom and a full bathroom—perfect for guests or extended family. Upstairs, the generous master suite includes a walk-in closet and private bath, along with a large loft for flexible

  Jared Lippelgoos COLDWELL BANKER RESIDENTIAL RE

  235 Hibiscus St, Winter Haven, FL 33881
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  /26

  $354,990 New Construction

  • 5 Beds
  • 3 Baths
  • 2,077 Sq Ft

  4035 Blackwell Ave, Lake Wales, FL 33859

  Under Construction. "Welcome to the Lakeside, one of our one-story floorplans featured in our Annabelle in Lake Wales, Florida. Take your pick between two artfully designed exteriors.Inside this beautiful 5 bedroom, 3 bathroom home, you'll find 2,077 square feet of comfortable living. The living area is an open concept, where your kitchen, living, and dining areas blend seamlessly into a

  Paul King DR HORTON REALTY OF CENTRAL FLORIDA LLC

  4035 Blackwell Ave, Lake Wales, FL 33859
• 

  

  /25

  $359,990 New Construction

  • 5 Beds
  • 3 Baths
  • 2,077 Sq Ft

  4422 Blackwell Ave, Lake Wales, FL 33859

  Under Construction. "Welcome to the Lakeside, one of our one-story floorplans featured in our Annabelle in Lake Wales, Florida. Take your pick between two artfully designed exteriors.Inside this beautiful 5 bedroom, 3 bathroom home, you'll find 2,077 square feet of comfortable living. The living area is an open concept, where your kitchen, living, and dining areas blend seamlessly into a

  Paul King DR HORTON REALTY OF CENTRAL FLORIDA LLC

  4422 Blackwell Ave, Lake Wales, FL 33859

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