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

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  /7

  $260,000 New Construction

  • 3 Beds
  • 2 Baths
  • 1,683 Sq Ft

  1740 2nd St NE, Winter Haven, FL 33881

  Brand-new 3-bedroom, 2-bath home just minutes from Downtown Winter Haven and the Chain of Lakes! Designed with flexibility in mind, this modern layout offers a potential private-entry suite ideal for in-laws, guests, or rental income. Featuring laminate wood floors, white cabinetry, stainless steel appliances, tankless water heater, and spacious open living areas. Move-in ready, no HOA, and close

  Daryl Ash, II KELLER WILLIAMS REALTY SMART

  1740 2nd St NE, Winter Haven, FL 33881
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  /35

  $240,000

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft

  24 Flamingo Blvd, Winter Haven, FL 33880

  Discover your cozy Winter Haven retreat - where comfort, style, and convenience come together in one inviting package! This charming 1,344 sq ft home offers 3 bedrooms and 2 bathrooms, making it an ideal fit for a growing family or anyone seeking a perfectly sized, easy-to-maintain space.Enjoy the freedom of owning both the home and the land. With no lot fees, no HOA, and no CDD fees, you're

  Cheryl Roda-Wu CENTURY 21 BE3

  24 Flamingo Blvd, Winter Haven, FL 33880
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  /37

  $283,000

  • 3 Beds
  • 2.5 Baths
  • 1,629 Sq Ft

  2302 Brassie Ct, Winter Haven, FL 33884

  One or more photo(s) has been virtually staged. PRICED TO SELL ! Great INVESTMENT opportunity in the desirable community of Winter Haven. This near-new home 2022 build is ideally situated for both comfort and convenience. This modern property offers 3 bedroom , 2 full baths and an additional bonus room perfect for an office, playroom, gym, or extra living space. Must see, do not look any further.

  Elena Garcia TOP AGENCY REALTY INC

  2302 Brassie Ct, Winter Haven, FL 33884
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  /27

  $300,000

  • 4 Beds
  • 2 Baths
  • 1,829 Sq Ft

  3112 Saint Charles Place, Winter Haven, FL 33884

  Short Sale. Perfect starter home or investment property! Welcome to this 4-bedroom, 2-bathroom residence located in the desirable Orleans community. Built in 2023, this charming corner-lot home offers an open floor plan with a spacious living area, kitchen, and dinette—all featuring easy-to-maintain tile flooring. A sliding glass door leads to the covered lanai, perfect for relaxing or

  Veronica Figueroa EXP REALTY LLC

  3112 Saint Charles Place, Winter Haven, FL 33884
• 

  $267,900 New Construction

  • 3 Beds
  • 2 Baths
  • 1,544 Sq Ft

  129 Nemo Ln, Winter Haven, FL 33881

  Brand-new, 3-bedroom, 2-story townhome with a garage for sale in Winter Haven, FL! Downstairs, enjoy an open living area with a spacious gathering room, plus a convenient powder room, a flex space, and a private covered lanai. Upstairs, relax in your private owner's suite with a walk-in wardrobe and a private en-suite bathroom including dual vanities, a decorative tiled shower, closeted toilet,

  Highland Homes Builder

  129 Nemo Ln, Winter Haven, FL 33881
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  /30

  $284,490 New Construction

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

  5535 Taverna Loop, Winter Haven, FL 33884

  Under Construction. Introducing the Harper floorplan at Villamar, where every square foot is put to use with sophistication and comfort. Inside this 4 bedroom, 2 bathroom home, you’ll find 1,665 square feet of comfortable living. This meticulously designed residence combines modern convenience with timeless elegance, showcasing granite and tile floors throughout. As you step inside, you are

  Paul King DR HORTON REALTY OF CENTRAL FLORIDA LLC

  5535 Taverna Loop, 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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  /26

  $209,900

  • 3 Beds
  • 1 Bath
  • 1,021 Sq Ft

  126 Summer View Cir, Winter Haven, FL 33880

  Step inside this charming 3-bedroom, 1-bathroom home in the heart of Winter Haven! Perfect for a first-time homebuyer or an investor looking to add a great rental to their portfolio, this solid block home is full of character and potential. Situated on a quiet street, the property offers a spacious yard that serves as a blank canvas ideal for adding a pool, creating a garden oasis, or designing

  Logan Coon KELLER WILLIAMS WINTER PARK

  126 Summer View Cir, Winter Haven, FL 33880
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  /14

  $259,900

  • 3 Beds
  • 2 Baths
  • 1,425 Sq Ft

  4913 Jackson St, Winter Haven, FL 33884

  Short Sale. Short Sale opportunity on a 2023-built 3BR/2BA home offering modern design, open living space, indoor laundry, and a 2-car garage. A rare chance to own newer construction at an affordable price point. Ideal for first-time buyers or investors seeking strong long-term potential. Conveniently located near shopping, dining, and major roadways. Lender approval required.

  Wanda Turner NONA LEGACY POWERED BY LA ROSA

  4913 Jackson St, Winter Haven, FL 33884
• 

  $279,900 New Construction

  • 3 Beds
  • 2 Baths
  • 1,544 Sq Ft

  109 Nemo Ln, Winter Haven, FL 33881

  Brand-new, 3-bedroom, 2-story townhome with a garage for sale in Winter Haven, FL! Downstairs, enjoy an open living area with a spacious gathering room, plus a convenient powder room, a flex space, and a private covered lanai. Upstairs, relax in your private owner's suite with a walk-in wardrobe and a private en-suite bathroom including dual vanities, a decorative tiled shower, closeted toilet,

  Highland Homes Builder

  109 Nemo Ln, Winter Haven, FL 33881
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  /9

  $246,000

  • 3 Beds
  • 2 Baths
  • 1,264 Sq Ft

  871 Reflections Loop E, Winter Haven, FL 33884

  Beautiful opportunity home with 3 bedrooms plus a den easily convertible into another room. The main room with its bathroom. This property is ideal for both investment and housing, located in a very quiet and pleasant area, perfect for those seeking comfort and quality of life. Very close to Legoland The property offers spacious and functional spaces, a large backyard and a comfortable

  Soraya Rios Afanador MY REALTY GROUP, LLC.

  871 Reflections Loop E, Winter Haven, FL 33884
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  /34

  $230,000

  • 3 Beds
  • 2 Baths
  • 1,268 Sq Ft

  2893 Whispering Trails Dr, Winter Haven, FL 33884

  This cozy home offers a warm and inviting layout, perfect for anyone who prefers comfort and easy living. It features a functional floor plan with a modern kitchen, bright bedrooms, and low-maintenance spaces that make everyday life simple. Ideally located near US-27, US-17, SR-540, and with quick access to I-4, you’re just a short drive from Orlando, Tampa, Disney, Legoland, lakes, parks,

  Jenny Caso LIFESTYLE INTERNATIONAL REALTY

  2893 Whispering Trails Dr, Winter Haven, FL 33884
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  /27

  $283,490 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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  /17

  $244,990

  • 3 Beds
  • 2 Baths
  • 1,309 Sq Ft

  3434 Avenue T NW, Winter Haven, FL 33881

  Remodeled and ready for your family. 3 bedrooms, 2 bathrooms home on lovely lot. Freshly painted, new laminate flooring, stainless steel appliances and more.

  Dewayne Smith CHARLES RUTENBERG REALTY ORLANDO

  3434 Avenue T NW, Winter Haven, FL 33881
• 

  $267,990 New Construction

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

  ALLEX 2 Plan at VillaMar, Winter Haven, FL 33884

  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 everyday living and

  D.R. Horton Builder

  3744 Giorgio Dr Unit 36202857, Winter Haven, FL 33884
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  /39

  $295,000

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

  751 Avenue B SW, Winter Haven, FL 33880

  Charming property with plenty of desirable features! This 3 bedrooms 2 baths remodeled home features a spacious kitchen with quartz countertops, Oversized cabinets, stainless steel appliances, tankless water heater. Come and enjoy the formal dinning room and living room, . Completely remodeled home, near shopping centers, schools, churches and hospitals offers convenience, while amazing views of

  Lucy Martinez CENTURY 21 WOLF'S CROSSING REALTY

  751 Avenue B SW, Winter Haven, FL 33880
• 

  $289,970 New Construction

  • 3 Beds
  • 2 Baths
  • 1,479 Sq Ft

  525 Ituna Cir, Winter Haven, FL 33881

  Brand-new 3-bedroom home for sale in Winter Haven, Florida, with a bright, open living area with volume ceilings, a beautiful owner's suite complete with a dual vanity en-suite bath, and a covered lanai for outdoor living! 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: Open

  Highland Homes Builder

  525 Ituna Cir, Winter Haven, FL 33881
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  /22

  $290,000

  • 3 Beds
  • 2 Baths
  • 1,453 Sq Ft

  541 Heather Glen Dr, Winter Haven, FL 33884

  Welcome to Heather Glen, a gated community in the heart of Winter Haven with an HOA of ONLY $150 A YEAR! This charming 3 bedroom, 2 bathroom home with an attached 2-car garage offers comfort, security, and convenience & ready for a quick close & move in. Featuring neutral gray walls, wood-look tile flooring, and plantation shutters throughout, this open-concept home is filled with natural light

  Jeavanna Lanza PA EXP REALTY LLC

  541 Heather Glen Dr, Winter Haven, FL 33884
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  /5

  $269,750 New Construction

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

  373 Wharf Way, Winter Haven, FL 33881

  3-bedroom, open layout, end-unit townhome for sale in Winter Haven, FL! Downstairs, enjoy an open living area with a spacious gathering room, plus a convenient powder room, den, and a private covered lanai. Upstairs, relax in your private owner's suite with a walk-in wardrobe and a private en-suite bathroom including dual vanities, a decorative tiled shower, closeted toilet, and linen closet. Two

  Highland Homes Builder

  373 Wharf Way, Winter Haven, FL 33881
• 

  

  /22

  $212,500

  • 2 Beds
  • 2 Baths
  • 1,517 Sq Ft

  2872 Attwater Loop, Winter Haven, FL 33884

  Ready to enjoy retirement the way it was meant to be? Welcome to 2872 Attwater Loop in Winter Haven, a desirable corner-unit home located in a peaceful and welcoming 55+ lakefront community designed for relaxed, low-maintenance living. This thoughtfully designed 2-bedroom, 2-bath residence with a flex/bonus room offers versatility for a home office, hobby space, or guest accommodations. As a

  Michelle Urena REALTY OF AMERICA

  2872 Attwater Loop, Winter Haven, FL 33884
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  /32

  $240,000

  • 4 Beds
  • 3 Baths
  • 2,174 Sq Ft

  5580 State Road 542 W, Winter Haven, FL 33880

  PRICE REDUCTION!!! MOTIVATED SELLER!!! Discover this exceptional income-producing property perfectly situated on a spacious 0.48-acre lot in the heart of Winter Haven. This versatile property features two separate living spaces, one currently rented—providing immediate income and excellent long-term investment potential. The main home which is now vacant and ready for it's new owners or tenants

  Jen Victor BRIGHT REALTY

  5580 State Road 542 W, 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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  /4

  $267,900 New Construction

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

  345 Wharf Way, Winter Haven, FL 33881

  Brand-new 3-bedroom, open layout, end-unit townhome for sale in Winter Haven, FL! Downstairs, enjoy an open living area with a spacious gathering room, plus a convenient powder room, flex space, and a private covered lanai. Upstairs, relax in your private owner's suite with a walk-in wardrobe and a private en-suite bathroom including dual vanities, a decorative tiled shower, closeted toilet, and

  Highland Homes Builder

  345 Wharf Way, Winter Haven, FL 33881
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  /31

  $295,000

  • 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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  /8

  $288,580 New Construction

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

  5125 Sylas Jax Ave, Winter Haven, FL 33884

  Brand-new 3-bedroom home for sale in Winter Haven, Florida! The Aurora features an inviting and open living area under an airy volume ceiling. Relax in your owner's suite with a private en-suite bath and dual closets. Plus, enjoy outdoor living on your covered lanai! This home includes features and finishes hand-selected by our professional designers to provide you with enduring style, move-in

  Highland Homes Builder

  5125 Sylas Jax Ave, Winter Haven, FL 33884
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  /45

  $289,900

  • 4 Beds
  • 2 Baths
  • 1,560 Sq Ft

  2128 Bretton Ridge Blvd, Winter Haven, FL 33884

  Welcome to 2128 Bretton Ridge Blvd, Winter Haven, FL 33884, a beautifully maintained 4-bedroom, 2-bath home built in 2017 and ideally situated in the desirable Winter Haven area of Polk County. With 1,560 square feet under roof, this move-in ready residence offers an open, thoughtfully designed floor plan that balances comfort and functionality. The spacious living and dining areas connect

  Kishroy Gilbert KISHROY REALTY GROUP LLC

  2128 Bretton Ridge Blvd, Winter Haven, FL 33884
• 

  

  /23

  $260,000

  • 3 Beds
  • 2 Baths
  • 1,075 Sq Ft

  1733 Sandalwood Cir SW, Winter Haven, FL 33880

  Attention Investors & Homeowners! Whether you’re a seasoned investor or looking for a home with built-in income, this property presents an exciting opportunity. This well-maintained 3-bedroom, 2-bath block home is located within Winter Haven city limits and offers 1,155 square feet of tile flooring throughout with no HOA. The home features a functional layout, spacious rooms, ample kitchen

  Melissa Ramirez BHHS FLORIDA PROPERTIES GROUP

  1733 Sandalwood Cir SW, Winter Haven, FL 33880
• 

  

  /19

  $235,000

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

  1661 Teagan Ln, Winter Haven, FL 33884

  Welcome to this beautifully built 2024 modern contemporary home located in a quiet and inviting community just minutes from the world-famous Orlando and Kissimmee theme parks. This stylish three-bedroom, two-bath residence features a thoughtfully designed open-concept layout that blends clean lines, functionality, and everyday comfort. The contemporary kitchen showcases sleek quartz countertops,

  Lora Harper Keller Williams Realty of PSL

  1661 Teagan Ln, Winter Haven, FL 33884
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  /32

  $279,465 New Construction

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

  5002 Abigail Dr, Winter Haven, FL 33859

  Welcome home to the Bradley, one of Dream Finders Homes’ most popular floor plans, offering 4 bedrooms, 2 baths, and 1,625 square feet of thoughtful design. Set on a beautiful homesite with no rear neighbors and a serene conservation view, this brand-new home combines privacy with comfort. The open layout showcases a spacious kitchen with quartz countertops, 42-inch cabinets, and energy-efficient

  Dream Finders Homes Builder

  5002 Abigail Dr, Winter Haven, FL 33859
• 

  

  /11

  $209,900

  • 3 Beds
  • 1.5 Baths
  • 1,166 Sq Ft

  1997 26th St NW, Winter Haven, FL 33881

  Cute as a button. Great starter home or investment property. Large corner lot. Featuring NEW ROOF, NEW SEPTIC, NEW ELECTRICAL PANELS. This three bedrooms one & one half bathroom has a new modern eat in kitchen and laminate floors. Open spacious living and dining room. Covered front porch. Why rent just buy. Adjoining vacant lot is not included in the sale and has been removed from the legal

  Angela Chapman CAPITAL REALTY GROUP FLORIDA

  1997 26th St NW, Winter Haven, FL 33881
• 

  $287,355 New Construction

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

  4490 Rapallo Ave, Winter Haven, FL 33884

  Brand-new 3-bedroom home for sale in Winter Haven, Florida! The Aurora features an inviting and open living area under an airy volume ceiling. Relax in your owner's suite with a private en-suite bath and dual closets. Plus, enjoy outdoor living on your covered lanai! This home includes features and finishes hand-selected by our professional designers to provide you with enduring style, move-in

  Highland Homes Builder

  4490 Rapallo Ave, Winter Haven, FL 33884
• 

  

  /19

  $295,000

  • 4 Beds
  • 2 Baths
  • 1,849 Sq Ft

  920 Cambridge Dr, Winter Haven, FL 33881

  Please use showingtime to schedule showings. Call listing agent.

  Briana Willis Global Advantage Realty LLC

  920 Cambridge Dr, Winter Haven, FL 33881
• 

  

  /16

  $275,900 New Construction

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

  Aurora Plan at Harbor at Lake Henry - Single-Family Homes, Winter Haven, FL 33881

  Introducing the Aurora by Highland Homes, featuring desirable details from the Craftsman-style exterior through the inviting interior! The Aurora features: A bright, open living area including a gathering room and kitchen with a pantry and eating space at the breakfast bar, under an airy volume ceiling. An owner's suite with volume ceilings, two wardrobe closets, a linen closet, and a private

  Highland Homes Builder

  612 Ituna Cir Unit 37319199, Winter Haven, FL 33881
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  /54

  $299,900

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

  2925 Dayton Dr, Winter Haven, FL 33884

  Discover the charm of this delightful 3-bedroom, 2-bath home located in the maintenance-free, 55+ gated community of Traditions at Lake Ruby. Thoughtfully designed for comfort and functionality, this home offers an inviting retreat for relaxed, worry-free living. Upon arrival, you’re welcomed by a spacious covered entrance enhanced with a leaded glass door and transom window. Inside, the eat-in

  Eileen Belanger CENTURY 21 MYERS REALTY LAKE WALES

  2925 Dayton Dr, Winter Haven, FL 33884
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  /12

  $298,750

  • 3 Beds
  • 2 Baths
  • 1,424 Sq Ft

  1505 Avenue F NE, Winter Haven, FL 33881

  Beautiful 3BR/2BA pool home on a large fenced lot! Features granite countertops, tile & laminate flooring, screened porch, and brand-new pavers. Enjoy your private pool or take a relaxing walk around nearby Lake Elbert. Conveniently located minutes from Legoland, new elementary school, Polk State College, and a coming-soon Publix.No HOA or CDD

  Lucy Martinez CENTURY 21 WOLF'S CROSSING REALTY

  1505 Avenue F NE, Winter Haven, FL 33881
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  /28

  $265,000

  • 3 Beds
  • 2 Baths
  • 1,454 Sq Ft

  5 Twilight Ln, Winter Haven, FL 33884

  Welcome to this beautifully remodeled 3-bedroom, 2-bathroom home in Winter Haven, where modern updates meet timeless charm. This property, with no HOA, has been extensively upgraded over the years to provide a comfortable and stylish living space. Highlights include a updated roof (July 2025) and HVAC system installed in 2021, all-new windows (October 2024), and full re piping for peace of mind.

  Patricia de Graaff RE/MAX HERITAGE PROFESSIONALS

  5 Twilight Ln, Winter Haven, FL 33884
• 

  

  /20

  $298,950 New Construction

  • 2 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 Homes Builder

  4130 Old Bartow Lake Wales Rd Unit 36431552, Lake Wales, FL 33859
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  /37

  $299,000

  • 3 Beds
  • 2 Baths
  • 1,460 Sq Ft

  403 Avenue J SE, Winter Haven, FL 33880

  **Turnkey Duplex on Prime Corner Lot with Strong Rental Income Potential** Exceptional opportunity to own a well-maintained **bungalow-style duplex** in a highly desirable corner-lot location. With a strong rental history and income-producing potential, this versatile **multi-family property** is ideal for investors or owner-occupants looking to generate rental income and offset mortgage

  Michael Hochadel BHHS FLORIDA PROPERTIES GROUP

  403 Avenue J SE, Winter Haven, FL 33880
• 

  

  /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
• 

  

  /3

  $297,990 New Construction

  • 4 Beds
  • 2 Baths
  • 1,758 Sq Ft

  Hillcrest Plan at Annabelle Estates, Winter Haven, FL 33859

  The Hillcrest floorplan is a spacious and thoughtfully designed one-story home that includes 4 bedrooms and 2 bathrooms, complemented by a two-car garage. This layout features a large great room at the heart of the home, seamlessly flowing into the dining area and kitchen for easy entertaining and family gatherings. The owner's suite is privately positioned and includes a walk-in closet and an

  Dream Finders Homes Builder

  5043 Abigail Dr Unit 36473369, Winter Haven, FL 33859

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