Winter Haven, FL Homes for Sale with Pool

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  /36

  $29,500

  • 2 Beds
  • 2 Baths
  • 672 Sq Ft

  515 Century Dr, Winter Haven, FL 33881

  2 Bed | 1 1/2 Bath | 672 square foot | $29,500 (Hidden Golf Club Lot 515) Charming 2-bedroom home in highly sought after 55+ Hidden Golf Community with great bones and lots of potential! This home has a NEW ROOF, VINYL SIDING, AND CARPORT. Inside, the home needs a little TLC but offers a cozy open layout. This gem is full of potential just waiting on your personal touch! Key Features include -NEW

  Brandi Sappington CRF Communities

  515 Century Dr, Winter Haven, FL 33881
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  /21

  $269,990

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,423 Sq Ft

  Summit Plan at Peace Creek Reserve - Serenity, Winter Haven, FL 33884

  This new two-story townhome offers ample space to live and grow with a total of three bedrooms. The first level features a spacious and flexible open-concept layout shared between the kitchen and family room, maximizing the interior living space. Two secondary bedrooms and a lavish owner’s suite featuring a full bathroom comprise the second floor.

  Lennar Builder

  3024 Captain Jax Way Unit 40307311, Winter Haven, FL 33884
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  /29

  $74,900

  $35K PRICE DROP

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

  100 El Camino Dr Unit 101, Winter Haven, FL 33884

  Owner motivated and ready to negotiate — WOW! This BEAUTIFUL 1361SF 2BR/2BA FIRST-FLOOR condo in Orchid Springs offers stunning lagoon/pond views! Located in the 55+ Granada Building, where at least one occupant must be 55+. IMMEDIATELY AVAILABLE and MOVE-IN READY!Step into an open, airy floor plan with tile throughout, creating a bright and spacious feel. The dining area, living room,

  Sharon Gastelbondo LPT REALTY, LLC

  100 El Camino Dr Unit 101, Winter Haven, FL 33884
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  /19

  $84,900

  • 2 Beds
  • 2 Baths
  • 1,160 Sq Ft

  1058 La Costa Ln Unit 100, Winter Haven, FL 33881

  2 Bed | 2 Bath | 1160 Sq. Ft. | $84,900|Four Lakes Golf Club - Lot 100 Beautiful Fully Furnished Home in a Gated 55+ Golf Community Enjoy resort-style living in this well-maintained 2000 Home of Merit manufactured home, located in a desirable gated 55+ community with outstanding amenities and golf privileges. Home Features 2 Bedrooms 2 Full Bathrooms Extra-Large Kitchen with elegant granite

  Cheryl Dobbs CRF Communities

  1058 La Costa Ln Unit 100, Winter Haven, FL 33881
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  /21

  $274,999

  New Construction $5K PRICE DROP

  • 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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  /65

  $655,000

  • 4 Beds
  • 3 Baths
  • 3,001 Sq Ft

  2428 Wildwood Ct, Winter Haven, FL 33884

  Welcome to Eloise Pointe Estates, an established gated community near the shores of Lake Eloise and the Winter Haven Chain of Lakes, just minutes from LEGOLAND Florida Resort. Tucked away at the end of a quiet cul-de-sac, this beautifully maintained 4-bedroom, 3-bathroom home offers 3,001 square feet of living space and an exceptional combination of privacy, comfort, and upgrades.Inside,

  Josh Taylor VILLAGE REALTY OF WINTER HAVEN

  2428 Wildwood Ct, Winter Haven, FL 33884
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  /39

  $356,315

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,227 Sq Ft

  816 Andreas St, Winter Haven, FL 33881

  Beautiful 2 Level, 2 Car Garage Home with Open Concept Living, Loft and 4 Bedrooms! Ready in October 2026! This Naples is in Coastal Elevation. The inviting front porch opens to a gracious foyer with adjacent powder room. The well-appointed, island kitchen is open to the adjoining cafe and spacious family room. The primary suite boasts an en suite bathroom with dual sink vanity, shower, private

  DRB Homes Builder

  816 Andreas St, Winter Haven, FL 33881
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  /25

  $274,900

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,302 Sq Ft

  3328 White Ibis Ln, Winter Haven, FL 33884

  Under Construction. Discover the Downing 2 floorplan at Harmony at Lake Eloise in Winter Haven, featuring 1,302 square feet, three bedrooms and two bathrooms, this home prioritizes efficient living without sacrificing an ounce of warmth. Step inside and be greeted by a thoughtfully arranged space, designed to maximize both comfort and flow. (Luxury vinyl) flooring guides you through the home,

  Paul King DR HORTON REALTY OF CENTRAL FLORIDA LLC

  3328 White Ibis Ln, Winter Haven, FL 33884
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  /73

  $1,699,900

  $100K PRICE DROP

  • 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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  /30

  $424,900

  New Construction

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

  1757 Hummingbird Rd, Winter Haven, FL 33884

  The property is located at 1757 Hummingbird Road WINTER HAVEN FL 33884 priced at 424900, 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

  1757 Hummingbird Rd, Winter Haven, FL 33884
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  /29

  $253,990

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,463 Sq Ft

  4719 Tony St, Lake Wales, FL 33859

  The property is located at 4719 Tony Street LAKE WALES FL 33859 priced at 253990, the square foot and stories are 1463, 2.The number of bath is 2, halfbath is 1 there are 3 bedrooms and 1 garages. For more details please, call or email.

  D.R. Horton Builder

  4719 Tony St, Lake Wales, FL 33859
• 

  Price To Be Determined

  New Construction

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

  Plan 2200 at Villamar, Winter Haven, FL 33884

  Adams Homes Builder

  836 Vienna Dr Unit 36462969, Winter Haven, FL 33884
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  /65

  $85,000

  $24K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,035 Sq Ft

  4127 Sprucewood St, Winter Haven, FL 33880

  Great home with an open living space ready for it's next owner. This home has a fresh coat of paint and is a blank slate for it's new owners. Sit on the front porch and enjoy your morning coffee. The rooms are nice sized with great closet space. The laundry/shop area has plenty of space for your Do-it-yourself projects. Oakwood Estates, a 55+ community offers 2 pools, 2 clubhouses, shuffleboard,

  Kathy Devor COLDWELL BANKER REALTY

  4127 Sprucewood St, Winter Haven, FL 33880
• 

  Price To Be Determined

  New Construction

  • 4 Beds
  • 2 Baths
  • 1,574 Sq Ft

  FLETCHER Plan at Annabelle Estates, Lake Wales, FL 33859

  Get ready to make our new community Annabelle Estates your new home in Lake Wales, Florida. You’ll find homes that range from 3 to 5 bedrooms and 1,328 to 2,077 square feet. Perfect for a variety of lifestyles and space needs. In addition to our single-family homes, Annabelle Estates also features stylish two-story townhomes offering 3 bedrooms, 2.5 baths, and a 1-car garage.Annabelle

  D.R. Horton Builder

  4019 Penelope Ave Unit 41623441, Lake Wales, FL 33859
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  /29

  $243,990

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,464 Sq Ft

  4706 Tony St, Lake Wales, FL 33859

  The property is located at 4706 Tony Street LAKE WALES FL 33859 priced at 243990, the square foot and stories are 1464, 2.The number of bath is 2, halfbath is 1 there are 3 bedrooms and 1 garages. For more details please, call or email.

  D.R. Horton Builder

  4706 Tony St, Lake Wales, FL 33859
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  /32

  $63,000

  $12K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,701 Sq Ft

  60 Bern Dr Unit 60, Winter Haven, FL 33881

  Swiss Village / Lot #60 / 2 Bedroom/ 2 Bath/ 1,701 Sq. Ft. / $63,000.00 SPRING SAVINGS WITH A 12K PRICE REDUCTION!!!! This GORGEOUS home has been meticulously taken care of and updated with: New Flooring, A/C, Roof, 13x9 Florida Room (which adds additonal sq. footage), & Updated Bathrooms! Fully furnished, this spacious home allows you plenty of room for storage and moving about (not that you

  Jennifer Torres CRF Communities

  60 Bern Dr Unit 60, Winter Haven, FL 33881
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  /69

  $164,900

  • 3 Beds
  • 2 Baths
  • 1,568 Sq Ft

  312 Siberian Cypress Cir, Winter Haven, FL 33881

  RENT TO OWN OPTION. SELLER IS WILLING TO RENT FOR A YEAR WITH AN OPTION TO BUY. Welcome to 312 Siberian Cypress Circle, a beautifully maintained 2019 home located in the highly desirable gated 55+ community of Cypress Creek Village in Winter Haven. One of this home's biggest advantages is its affordable lot rent of just **$616 per month**, making it an exceptional value in today's market while

  Daniel Butler Sun Realty of Florida

  312 Siberian Cypress Cir, Winter Haven, FL 33881
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  /50

  $450,000

  • 3 Beds
  • 2.5 Baths
  • 2,352 Sq Ft

  205 Thomas Ct, Winter Haven, FL 33880

  Welcome to this spacious 3-bedroom, 2.5-bath home offering 2,352 square feet of living space on a generous .33-acre lot tucked away on a quiet cul-de-sac. Designed for both comfortable everyday living and entertaining, this home offers plenty of space inside and out.One of the standout features is the massive bonus room with its own private entrance and an impressive feature wall complete

  Stephanie Mayo REGAL REAL ESTATE LLC

  205 Thomas Ct, Winter Haven, FL 33880
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  /8

  $259,900

  New Construction $29K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,358 Sq Ft

  5125 Sylas Jax Ave, Winter Haven, FL 33884

  Move-in ready 3-bedroom home for sale in Winter Haven, Florida, featuring an open living area with airy volume ceilings, a private en-suite owner's bath, and outdoor living space on a covered lanai!This home includes features and finishes hand-selected by our professional designers to provide you with enduring style, move-in convenience, and easy home maintenance:A bright, open

  Highland Homes Builder

  5125 Sylas Jax Ave, Winter Haven, FL 33884
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  /11

  $26,900

  • 2 Beds
  • 2 Baths

  526 Cardinal Blvd, Winter Haven, FL 33881

  Welcome to maintenance-free, active resort-style living! This charming 2019 single-wide mobile home measures 12x52 and offers a comfortable, modern layout featuring two bedrooms and two spacious bathrooms, each complete with a full-size tub. Enjoy an inviting open-concept kitchen and living area filled with lovely natural light, complemented by a convenient mix of durable laminate flooring and

  Yvonne Straub Bedrock MH Sales LLC

  526 Cardinal Blvd, Winter Haven, FL 33881
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  /52

  $849,900

  • 5 Beds
  • 3.5 Baths
  • 4,108 Sq Ft

  25 Lakewood Causeway, Winter Haven, FL 33884

  Welcome to a truly special waterfront property in Winter Haven, set on 1.28 private acres with water on both sides. Located on Lake Link with Lake Otis directly across the street, the two lakes form a connected two-lake chain offering boating, fishing and plenty of opportunities to enjoy life on the water. Enjoy beautiful lake views from both sides of the home and spectacular sunsets over Lake

  Melissa Meyer KEENE'S POINTE REALTY

  25 Lakewood Causeway, Winter Haven, FL 33884
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  /76

  $139,900

  • 2 Beds
  • 2 Baths
  • 1,804 Sq Ft

  4234 Rolling Oaks Dr, Winter Haven, FL 33880

  Walk right into this beautiful home located in Oakwood Estates, a 55+ community. You will find the home nicely furnished which all conveys with the sale of the home. The open living area at the front of the home has a beautiful lake view. The kitchen is open to another living space or dining area. The primary bedroom at the rear of the home is nice sized and will accommodate a king sized bed. The

  Kathy Devor COLDWELL BANKER REALTY

  4234 Rolling Oaks Dr, Winter Haven, FL 33880
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  /56

  $99,000

  • 2 Beds
  • 1 Bath
  • 840 Sq Ft

  1700 6th St NW Unit C24, Winter Haven, FL 33881

  Peaceful oasis in a premier 55+ community! This lovely 2 bedroom, 1 bath second-floor condo in Winter Haven Harbour Apartments offers a perfect blend of comfort, functionality, and an active, low-maintenance lifestyle. Inside, you will find a spacious living room that flows effortlessly into a dedicated dining room, and a galley-style kitchen that maximizes counter space and storage, making meal

  Chrissi Jasso ASSOCIATE REALTY

  1700 6th St NW Unit C24, Winter Haven, FL 33881
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  /2

  $287,355

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,358 Sq Ft

  4490 Rapallo Ave, Winter Haven, FL 33884

  Move-in ready 3-bedroom home for sale in Winter Haven, Florida, featuring an open living area with airy volume ceilings, a private en-suite owner's bath, and outdoor living space on a covered lanai!This home includes features and finishes hand-selected by our professional designers to provide you with enduring style, move-in convenience, and easy home maintenance:A bright, open

  Highland Homes Builder

  4490 Rapallo Ave, Winter Haven, FL 33884
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  /64

  $125,000

  $3K PRICE DROP

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

  4239 Cedarwood St, Winter Haven, FL 33880

  Open and spacious living area is the best way to describe this home. The home features two living areas plus the lanai for additional space. The primary bedroom is large offering two built in closets and a spacious bathroom. The guest bedroom has the bath attached, perfect for visiting guests. The kitchen has an updated island perfect for entertaining. The laundry is located inside the home. Move

  Kathy Devor COLDWELL BANKER REALTY

  4239 Cedarwood St, Winter Haven, FL 33880
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  /21

  $360,000

  • 4 Beds
  • 2 Baths
  • 2,256 Sq Ft

  313 Terranova Blvd, Winter Haven, FL 33884

  Virtually Staged. This Winter Haven one-story home offers a two-car garage. Included 100-Day Home Warranty with buyer activation

  Karen Albright OPENDOOR BROKERAGE LLC

  313 Terranova Blvd, Winter Haven, FL 33884
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  /44

  $315,000

  $10K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,109 Sq Ft

  516 Reggie Rd, Winter Haven, FL 33884

  Built in 2024, this single-story home in Peace Creek Reserve offers the Freedom floor plan with a dedicated office and a private Next Gen suite — its own entrance, bedroom, living area, kitchenette, and dedicated laundry area with washer/dryer hookups, separate from the main home's laundry room. Inside, an open-concept kitchen with quartz countertops, stainless steel appliances, an oversized

  Sandra Vargas Valdeleon MY REALTY GROUP, LLC.

  516 Reggie Rd, Winter Haven, FL 33884
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  /8

  $325,000

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft

  4913 Kaia Ave, Winter Haven, FL 33884

  Stunning VillaMar residence in Winter Haven, built in 2024, showcasing modern construction with a clean, contemporary design throughout. The interior features an inviting layout highlighted by a chef-style kitchen that opens seamlessly to a spacious great room, creating an ideal space for both everyday living and entertaining.This home includes a whole-house water filtration system, a

  Lucy Elias LEGACY REALTY PARTNERS, LLC.

  4913 Kaia Ave, Winter Haven, FL 33884
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  /2

  $330,900

  New Construction $17K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,227 Sq Ft

  4498 Rapallo Ave, Winter Haven, FL 33884

  Move-in ready 2-story home for sale in Winter Haven, Florida, with 4 bedrooms plus a loft!Downstairs, enjoy a welcoming, open living area with luxury vinyl plank flooring, opening to desirable outdoor living space with a large covered lanai spanning the entire back of your home! Upstairs, your beautiful owner's suite is complete with a private en-suite bath with a decorative tiled shower

  Highland Homes Builder

  4498 Rapallo Ave, Winter Haven, FL 33884
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  /53

  $399,000

  $21K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,676 Sq Ft

  605 Sarner Pass Way, Winter Haven, FL 33881

  This 4-bedroom, 2.5-bathroom home offers modern comfort, thoughtful design, and nearly convenience. Built in 2022, this spacious two-story residence is ideally situated on a desirable corner lot in Lake Lucerne community. The main level features an open-concept layout that connects the living room, dining area, and kitchen—perfect for everyday living and entertaining. The kitchen is features

  Nankumar Seelall HOMESMART

  605 Sarner Pass Way, Winter Haven, FL 33881
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  /20

  $133,000

  $19K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 989 Sq Ft

  6764 Brentwood Dr NE, Winter Haven, FL 33881

  Welcome to one of the most desirable 55+ communities in Florida! You have found this hidden gem located on a canal front lot between Lake Henry and Lake Hamilton in Northeast Winter Haven. This FURNISHED 2-bedroom, 2-bathroom manufactured home will offer you a relaxing move-in ready lifestyle with multiple upgrades. Some of the extras included in your purchase are a new roof, upgraded kitchen

  Toni Albritton TONI ALBRITTON

  6764 Brentwood Dr NE, Winter Haven, FL 33881
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  /9

  $295,900

  New Construction $12K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,568 Sq Ft

  5121 Sylas Jax Ave, Winter Haven, FL 33884

  Move-in ready, open layout, 2-story home for sale in Winter Haven, Florida, with 3 bedrooms plus a loft!Downstairs, you'll enjoy a desirable open living area with luxury vinyl plank flooring. Upstairs, you'll find privacy in your owner's suite complete with an en-suite bath with dual vanities, a decorative tiled shower with glass enclosure, a closeted toilet, and a walk-in wardrobe. Two

  Highland Homes Builder

  5121 Sylas Jax Ave, Winter Haven, FL 33884
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  /43

  $452,000

  $18K PRICE DROP

  • 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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  /35

  $319,990

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,305 Sq Ft

  5588 Taverna Loop, Winter Haven, FL 33884

  The property is located at 5588 Taverna Loop WINTER HAVEN FL 33884 priced at 319990, the square foot and stories are 2305, 2.The number of bath is 2, halfbath is 1 there are 4 bedrooms and 2 garages. For more details please, call or email.

  D.R. Horton Builder

  5588 Taverna Loop, Winter Haven, FL 33884
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  /61

  $284,500

  $26K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,109 Sq Ft

  2925 Dayton Dr, Winter Haven, FL 33884

  Discover the perfect blend of comfort, elegance, and low-maintenance living in this beautifully maintained 3-bedroom, 2-bath home, ideally situated in the highly sought-after 55+ gated community of Traditions at Lake Ruby. Thoughtfully designed with both style and functionality in mind, this residence offers the ideal setting for a relaxed Florida lifestyle. A spacious covered front entry

  Eileen Belanger CENTURY 21 MYERS REALTY LAKE WALES

  2925 Dayton Dr, Winter Haven, FL 33884
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  /26

  $284,990

  New Construction $13K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,480 Sq Ft

  337 Meredith Blvd, Winter Haven, FL 33881

  MOVE-IN READY! Single Level Home with 3 Bedrooms! Welcome to your dream home in the sought-after Willowbrook North community! This stunning Ranch-style, one-story residence offers effortless living with 3 spacious bedrooms, 2 full bathrooms, and a versatile flex space—perfect for a home office or additional living area. You'll fall in love with the modern open-concept layout, featuring quartz

  DRB Homes Builder

  337 Meredith Blvd, Winter Haven, FL 33881
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  /58

  $78,000

  $21K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,568 Sq Ft

  148 Greenview Dr, Winter Haven, FL 33881

  2 Bed | 2 Bath | 1568 square foot | $78,000 (Swiss Golf and Tennis- Lot 148) Huge PRICE DROP! Enjoy resort-style living in this completely remodeled home with large bedrooms and walk in closets. Located in highly sought after 55+ Community! Home Features -New roof and A/C - only 2 years old -Modern kitchen with new cabinets, granite countertops, and new stainless-steel appliances -All new windows

  Brandi Sappington CRF Communities

  148 Greenview Dr, Winter Haven, FL 33881
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  /33

  $340,000

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

  604 Sarner Pass Way, Winter Haven, FL 33881

  Seller motivated — great opportunity for investors or future homeowners! This beautiful corner lot home features 4 bedrooms and 2 bathrooms, offering comfort, space, and excellent income potential. The spacious kitchen comes fully equipped with all appliances, including a refrigerator, stove, microwave, and dishwasher, making it move-in ready from day one. The open-concept layout seamlessly

  Anderson Siqueira, Sr WRA BUSINESS & REAL ESTATE

  604 Sarner Pass Way, Winter Haven, FL 33881
• 

  

  /22

  $289,989

  New Construction $5K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,625 Sq Ft

  296 Meredith Blvd, Winter Haven, FL 33881

  Move into your brand-new home at Willowbrook North, with completion anticipated in August 2026! The thoughtfully designed Bradley floor plan offers 1,625 square feet of open-concept living that feels even more spacious thanks to its soaring 9'4 ceilings and seamless layout. This home features a bright and inviting kitchen with beautiful stone countertops that continue into every bathroom for a

  Dream Finders Homes Builder

  296 Meredith Blvd, Winter Haven, FL 33881
• 

  

  /20

  $304,950

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,710 Sq Ft

  Azure Plan at Annabelle Estates, Lake Wales, FL 33859

  Formal entry and hallway as you enter the home with study located at front of home. Spacious great room with kitchen open to dining and family entertainment area that then open to a covered patio. Great size owner’s bedroom with dual sink owner’s bath and walk in closet. Convenient mud room and laundry room at entry from garage. Optional 3rd bedroom at study available.

  Richmond American Builder

  4130 Old Bartow Lake Wales Rd Unit 36431552, Lake Wales, FL 33859

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