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

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  $299,990 New Construction

  • 3 Beds
  • 2 Baths
  • 1,562 Sq Ft

  2795 San Marco Way, Winter Haven, FL 33884

  Welcome to the Ventura — Stylish Single-Story Living Meet the Ventura, a home design offering up to 1,562 square feet of comfortable, single-level living. This thoughtfully designed floor plan includes 3 to 4 bedrooms, 2 bathrooms, and a spacious 2-car garage — all on one convenient floor. The Ventura’s open-concept layout creates a bright, airy space with a built-in flex area that adapts to your

  

  Maronda Homes

  Builder

  2795 San Marco Way, Winter Haven, FL 33884
• 

  $284,990 New Construction

  • 3 Beds
  • 2 Baths
  • 1,492 Sq Ft

  2751 San Marco Way, Winter Haven, FL 33884

  Efficient and Thoughtfully Designed Living in The Victoria Though compact in size, The Victoria offers a smart and efficient floor plan designed for modern family living. A charming front porch leads into a practical entryway with convenient access to the mudroom and two-car garage. At the heart of the home, a spacious family room serves as the central gathering space. The breakfast room, located

  

  Maronda Homes

  Builder

  2751 San Marco Way, Winter Haven, FL 33884
• 

  

  /2

  $299,990 New Construction

  • 3 Beds
  • 2 Baths
  • 1,562 Sq Ft

  2775 San Marco Way, Winter Haven, FL 33884

  Welcome to the Ventura — Stylish Single-Story Living Meet the Ventura, a home design offering up to 1,562 square feet of comfortable, single-level living. This thoughtfully designed floor plan includes 3 to 4 bedrooms, 2 bathrooms, and a spacious 2-car garage — all on one convenient floor. The Ventura’s open-concept layout creates a bright, airy space with a built-in flex area that adapts to your

  

  Maronda Homes

  Builder

  2775 San Marco Way, Winter Haven, FL 33884
• 

  $269,990 New Construction

  • 3 Beds
  • 2 Baths
  • 1,492 Sq Ft

  2767 San Marco Way, Winter Haven, FL 33884

  Efficient and Thoughtfully Designed Living in The Victoria Though compact in size, The Victoria offers a smart and efficient floor plan designed for modern family living. A charming front porch leads into a practical entryway with convenient access to the mudroom and two-car garage. At the heart of the home, a spacious family room serves as the central gathering space. The breakfast room, located

  

  Maronda Homes

  Builder

  2767 San Marco Way, Winter Haven, FL 33884
• 

  $300,000 New Construction

  • 4 Beds
  • 2 Baths
  • 1,607 Sq Ft

  5009 Kaia Ave, Winter Haven, FL 33884

  An open floorplan that makes entertaining easy in the open kitchen, dining, and great room that flow to the patio. The primary suite is tucked in the rear of the home offering plenty of privacy and features a spacious walk-in closet and shower.

  

  Meritage Homes

  Builder

  5009 Kaia Ave, Winter Haven, FL 33884
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  /2

  $285,000 New Construction

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

  5001 Kaia Ave, Winter Haven, FL 33884

  Open kitchen flows to the dining space, great room and outside patio.

  

  Meritage Homes

  Builder

  5001 Kaia Ave, Winter Haven, FL 33884
• 

  $270,000 New Construction

  • 3 Beds
  • 2 Baths
  • 1,269 Sq Ft

  4989 Kaia Ave, Winter Haven, FL 33884

  Prepare dinner while catching up on the day's events from this home's chef-inspired kitchen which overlooks a great room.

  

  Meritage Homes

  Builder

  4989 Kaia Ave, Winter Haven, FL 33884
• 

  /2

  $273,900 New Construction

  • 3 Beds
  • 2 Baths
  • 1,266 Sq Ft

  985 Lunar Ln, Winter Haven, FL 33884

  Under Construction. Crescent Pointe is a brand new community located in Winter Haven, FL, conveniently situated off State Rd 653 and boasting easy access to a range of nearby attractions. For residents who enjoy outdoor activities, the Winter Haven Chain of Lakes is nearby. It offers opportunities for boating, fishing, and other recreational activities. The community is also close to the bustling

  Keith Greene VANTAGE PROPERTY MANAGEMENT LLC

  985 Lunar Ln, Winter Haven, FL 33884
• 

  $294,900 New Construction

  • 3 Beds
  • 2 Baths
  • 1,787 Sq Ft

  The Westminster II Plan at Crescent Pointe, Winter Haven, FL 33884

  

  Southern Homes

  Builder

  7623 State Highway 653 Hwy Unit 37275852, Winter Haven, FL 33884
• 

  $286,900 New Construction

  • 3 Beds
  • 2 Baths
  • 1,478 Sq Ft

  The Bristol II Plan at Crescent Pointe, Winter Haven, FL 33884

  

  Southern Homes

  Builder

  7623 State Highway 653 Hwy Unit 37275824, Winter Haven, FL 33884
• 

  $277,900 New Construction

  • 3 Beds
  • 2 Baths
  • 1,447 Sq Ft

  The Newport II Plan at Crescent Pointe, Winter Haven, FL 33884

  

  Southern Homes

  Builder

  7623 State Highway 653 Hwy Unit 37275805, Winter Haven, FL 33884
• 

  $273,900 New Construction

  • 3 Beds
  • 2 Baths
  • 1,266 Sq Ft

  The Charlotte II Plan at Crescent Pointe, Winter Haven, FL 33884

  

  Southern Homes

  Builder

  7623 State Highway 653 Hwy Unit 37275765, Winter Haven, FL 33884
• 

  

  /21

  $245,000

  • 3 Beds
  • 2 Baths
  • 1,317 Sq Ft

  144 Brad Cir, Winter Haven, FL 33880

  Short Sale. DELIGHTFUL 3 bedroom, 2 bath home with a 2-car garage! Spanning just over 1,300 square feet of living space, this home offers an OPEN FLOOR Plan with a nice-sized living room combined with the dining area and kitchen with an eat-in space. The kitchen boasts lovely countertops with a matching backsplash and ample cabinets for storage. Split Bedrooms! The primary bedroom is complete

  Chrissi Jasso ASSOCIATE REALTY

  144 Brad Cir, Winter Haven, FL 33880
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  /29

  $255,000

  • 3 Beds
  • 2 Baths
  • 1,725 Sq Ft

  3305 Royal Tern Dr, Winter Haven, FL 33881

  Short Sale. ***SHORT SALE*Discover Your Dream Home at Lakeside Landing! Welcome to this immaculate home in the picturesque community of Lakeside Landing! This property offers the ultimate in modern living, combining comfort, style, and functionality. It's move-in ready and equipped with smart home technology, energy-efficient windows, and solar panels to help you save on energy costs. Plus, enjoy

  Brenda Anglada RE/MAX PRIME PROPERTIES

  3305 Royal Tern Dr, Winter Haven, FL 33881
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  /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
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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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  /23

  $249,000

  • 3 Beds
  • 3 Baths
  • 1,696 Sq Ft

  130 Avenue H SE, Winter Haven, FL 33880

  Short Sale. Step into timeless character blended with thoughtful updates in this charming 2-story home. Enter through a welcoming foyer where you’ll find the staircase leading to the second floor and a warm sense of home. The heart and soul of this property is the beautifully remodeled kitchen, featuring tall ceilings, eat-in area, and elegant granite countertops and backsplash—perfect for

  Nancy Parkhurst LA ROSA REALTY KISSIMMEE

  130 Avenue H SE, Winter Haven, FL 33880
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  /17

  $215,000

  • 2 Beds
  • 2 Baths
  • 1,118 Sq Ft

  1224 Vienna Square Dr, Winter Haven, FL 33884

  REDCUCED AGAIN! CAN'T BEAT THIS PRICE IN THIS COMMUNITY!!! This is a charming 2-bedroom, 2-bath home in a desirable adult living gated community. This well-kept residence features a spacious master suite with a walk-in shower, a bright and open living area, and a functional kitchen perfect for everyday living. Step outside to a screened-in back porch—ideal for relaxing or entertaining in comfort.

  Don Jerue KELLER WILLIAMS REALTY SMART 1

  1224 Vienna Square Dr, Winter Haven, FL 33884
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  /5

  $270,000

  • 4 Beds
  • 2 Baths
  • 1,828 Sq Ft

  1104 Star Ruby Ln, Winter Haven, FL 33880

  Short Sale. Spacious Cali model featuring 4 bedrooms and 2 baths. The home is located within the Squires Grove community of Winter Haven. The home features 4 spacious bedrooms. The open concept kitchen is great for entertaining with family and friends. The home also features an attached 2 car garage. The home is being sold in as is condition.This home is being sold through the short sale

  Jesse Carriedo REALTYCITY INC

  1104 Star Ruby Ln, Winter Haven, FL 33880
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  /7

  $245,000

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

  1540 Avenue C NE, Winter Haven, FL 33881

  Short Sale. Quaint 3/2 home perfect for 1st time homebuyers or could be a great rental property. Contract is contingent upon third party bank approval. Centrally located to major highways and shopping.

  Robert Miller MILLSHIRE REALTY

  1540 Avenue C NE, Winter Haven, FL 33881
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  /44

  $270,000

  • 3 Beds
  • 2 Baths
  • 1,698 Sq Ft

  136 Krenson Bay Loop, Winter Haven, FL 33881

  Short Sale. PRICE REDUCED—MOTIVATED SELLER! Nestled in the desirable gated community of Krenson Bay, this well-maintained 3-bedroom, 2-bathroom home is move-in ready and waiting for you! Offering 1,720 sq. ft. of thoughtfully designed living space, this home blends comfort, style, and energy efficiency—built by Adams Homes to help keep utility costs low. Step inside to all-tile flooring, with

  Lori Edwards COLDWELL BANKER REALTY

  136 Krenson Bay Loop, Winter Haven, FL 33881
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  /51

  $289,900

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft

  300 Lake Smart Cir, Winter Haven, FL 33881

  Short Sale. Price must be approved by the bank. Short Sale-Welcome to this beautiful 3-bedroom, 2-bathroom single-family home featuring a spacious two-car garage and a relaxing screened-in patio. Nestled in a desirable community with a private fishing pier, this home is perfect for outdoor enthusiasts. Plus, a public boat ramp is conveniently located just across the street, providing easy access

  Brandy Duncan COLDWELL BANKER REALTY

  300 Lake Smart Cir, Winter Haven, FL 33881
• 

  

  /23

  $265,000

  • 4 Beds
  • 2.5 Baths
  • 3,020 Sq Ft

  5018 Strada Dr, Winter Haven, FL 33880

  Short Sale. Packed with potential! This spacious two-story home, featuring 4 bedrooms, 2.5 baths, and a versatile bonus room needs some repairs, cleaning, and TLC, but that’s where the attractive price comes in! The main floor includes a large great room, white kitchen with granite countertops, front living room/den, laundry, enclosed bonus room and a 3-car garage. The lanai offers a great

  Tanja Cisliek FUTURE HOME REALTY INC

  5018 Strada Dr, Winter Haven, FL 33880
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  /12

  $295,500

  • 4 Beds
  • 3 Baths
  • 2,020 Sq Ft

  3077 Brenton Manor Loop, Winter Haven, FL 33881

  Short Sale. SHORT SALE. SHORT SALE, Calling Investors ,FIXER UPPER, 4 bedrooms, 3 bath home in Central Florida! Enjoy privacy with only one side neighbor and no back neighbor, come and see this Beautiful Home with an open-concept layout and spacious bedrooms & high vaulted ceilings Don't miss the chance to make this property your new home. SELLER WILL NOT MAKE ANY REPAIRS, PROPERTY IS AS IS.

  Amanda Linsey VYLLA HOME

  3077 Brenton Manor Loop, Winter Haven, FL 33881
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  /61

  $250,000

  • 3 Beds
  • 2 Baths
  • 1,597 Sq Ft

  103 13th St SE, Winter Haven, FL 33880

  Short Sale. NO HOA! Well-maintained and move-in ready, this three bedroom, two bathroom house has everything you need to call it "home". The roof was replaced in 2022 and the wiring was replaced within the last two years. Wood-look ceramic tile flows throughout the entire home, making it easy to clean and pet friendly. A real wood-burning fireplace is the focal point of the spacious living

  Kris Bender BENDER REALTY, LLC

  103 13th St SE, Winter Haven, FL 33880
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  /65

  $289,000

  • 3 Beds
  • 2 Baths
  • 2,029 Sq Ft

  4469 Turnberry Ln, Lake Wales, FL 33859

  MOTIVATED SELLER! CDD DEBT PAID IN FULL! ******PRICED TO SELL***** 4469 Turnberry Lane Lake Wales, Florida 33859 is a 3 Bedroom/2 Bath Provence floor plan located in Lake Ashton, a gated and guarded 55+ community with resort style amenities and activities. This spacious floor plan offers new interior paint, freshly painted garage floor, tray ceilings, crown molding, custom columns with

  Lori Raath LAKE ASHTON REALTY INC.

  4469 Turnberry Ln, Lake Wales, FL 33859
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  /50

  $225,000

  • 2 Beds
  • 2 Baths
  • 1,083 Sq Ft

  4488 Turnberry Ln, Lake Wales, FL 33859

  Welcome Home! Step into comfort in this cozy 2-bedroom, 2-bathroom retreat nestled in the heart of Lake Ashton’s 55+ community. The kitchen gleams with crown molding, Samsung stainless-steel appliances, and a sleek design that blends style with functionality. A true hidden gem awaits beyond the living room: a three-panel sliding glass door opens wide to a screened lanai, seamlessly merging indoor

  Candra Alston LAKE ASHTON REALTY INC.

  4488 Turnberry Ln, Lake Wales, FL 33859
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  /49

  $250,000

  • 2 Beds
  • 2 Baths
  • 1,319 Sq Ft

  4152 Aberdeen Ln, Lake Wales, FL 33859

  ***PRICE REDUCED***MOTIVATED SELLER! This home is ready for a new owner. This South facing home offers 2 Bedrooms, 2 Baths and an enclosed lanai with transitional windows and awning. Located behind the secure gates of Lake Ashton, this Caribbean Floor Plan home offers a new roof (2021) and gutters and backs up to a pond. The new owner will enjoy the paver driveway and walk way that leads to the

  Lori Raath LAKE ASHTON REALTY INC.

  4152 Aberdeen Ln, Lake Wales, FL 33859
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  /56

  $284,900

  • 2 Beds
  • 2 Baths
  • 1,605 Sq Ft

  4432 Waterford Dr, Lake Wales, FL 33859

  The CDD DEBT IS PAID IN FULL, adding even more value to this incredible property! This wonderful Caribbean model home, located in the prestigious golfing community of Lake Ashton, offers resort-style living at its finest. The spacious 2-bedroom, 2-bathroom floor plan is designed for both comfort and entertainment. As you step through the screened-in front porch, you’ll be welcomed into an

  Eileen Belanger CENTURY 21 MYERS REALTY LAKE WALES

  4432 Waterford Dr, Lake Wales, FL 33859
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  /30

  $262,990 New Construction

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

  4623 Linda St, Lake Wales, FL 33898

  Under Construction. "Introducing the Pearson – where modern elegance meets everyday functionality in this stylish townhome. Located in Anabelle in Lake Wales, Florida. Step into sophistication as you enter through the one-car garage into a spacious and welcoming abode with 1,463 square feet. The heart of the home, a sprawling living space, beckons with its ample room and abundant natural

  Paul King DR HORTON REALTY OF CENTRAL FLORIDA LLC

  4623 Linda St, Lake Wales, FL 33898
• 

  

  /30

  $257,990 New Construction

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

  4619 Linda St, Lake Wales, FL 33898

  Under Construction. "Introducing the Pearson – where modern elegance meets everyday functionality in this stylish townhome. Located in Annabelle in Lake Wales, Florida. Step into sophistication as you enter through the one-car garage into a spacious and welcoming abode with 1,463 square feet. The heart of the home, a sprawling living space, beckons with its ample room and abundant natural

  Paul King DR HORTON REALTY OF CENTRAL FLORIDA LLC

  4619 Linda St, Lake Wales, FL 33898
• 

  

  /30

  $257,990 New Construction

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

  4615 Linda St, Lake Wales, FL 33898

  Under Construction. "Introducing the Pearson – where modern elegance meets everyday functionality in this stylish townhome. Located in Annabelle in Lake Wales, Florida. Step into sophistication as you enter through the one-car garage into a spacious and welcoming abode with 1,463 square feet. The heart of the home, a sprawling living space, beckons with its ample room and abundant natural

  Paul King DR HORTON REALTY OF CENTRAL FLORIDA LLC

  4615 Linda St, Lake Wales, FL 33898
• 

  

  /30

  $257,990 New Construction

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

  4611 Linda St, Lake Wales, FL 33898

  Under Construction. "Introducing the Pearson – where modern elegance meets everyday functionality in this stylish townhome. Located in Annabelle in Lake Wales, Florida. Step into sophistication as you enter through the one-car garage into a spacious and welcoming abode with 1,463 square feet. The heart of the home, a sprawling living space, beckons with its ample room and abundant natural

  Paul King DR HORTON REALTY OF CENTRAL FLORIDA LLC

  4611 Linda St, Lake Wales, FL 33898
• 

  

  /30

  $257,990 New Construction

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

  4607 Linda St, Lake Wales, FL 33898

  Under Construction. "Introducing the Pearson – where modern elegance meets everyday functionality in this stylish townhome. Located in Annabelle in Lake Wales, Florida. Step into sophistication as you enter through the one-car garage into a spacious and welcoming abode with 1,463 square feet. The heart of the home, a sprawling living space, beckons with its ample room and abundant natural

  Paul King DR HORTON REALTY OF CENTRAL FLORIDA LLC

  4607 Linda St, Lake Wales, FL 33898
• 

  

  /30

  $262,990 New Construction

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

  4603 Linda St, Lake Wales, FL 33898

  Under Construction. "Introducing the Pearson – where modern elegance meets everyday functionality in this stylish townhome. Located in Annabelle in Lake Wales, Florida. Step into sophistication as you enter through the one-car garage into a spacious and welcoming abode with 1,463 square feet. The heart of the home, a sprawling living space, beckons with its ample room and abundant natural

  Paul King DR HORTON REALTY OF CENTRAL FLORIDA LLC

  4603 Linda St, Lake Wales, FL 33898
• 

  

  /35

  $250,000 New Construction

  • 3 Beds
  • 2 Baths
  • 1,450 Sq Ft

  8150 Cherokee Rd, Bartow, FL 33830

  One or more photo(s) has been virtually staged. Under Construction. This brand-new home is scheduled to be completed and affixed to the property by the end of August. The first photo is a rendering for visualization purposes, and the additional images showcase the model unit of the "Marvelous 3" by Clayton Homes. This stunning 3-bedroom, 2-bathroom home offers 1,450 square feet of thoughtfully

  Chad Lindsey KELLER WILLIAMS REALTY SMART 1

  8150 Cherokee Rd, Bartow, FL 33830
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  /13

  $279,990

  • 4 Beds
  • 2 Baths
  • 1,707 Sq Ft

  546 Lorient Dr, Eagle Lake, FL 33839

  Short Sale. Come see this beautiful 4 bedroom 2 bathroom home located in the sought after community of Normandy Heights! Why wait nearly a year on a new construction home when you can move into this 2019 model ASAP and get tons of upgrades as well! This home is nearly 1800 living sq. ft., has an open floor plan great for entertaining, and offers the following upgrades: vinyl plank flooring

  Zaida Cordero LA ROSA REALTY LLC

  546 Lorient Dr, Eagle Lake, FL 33839

Showing Results 281 - 317, Page 8 of 8