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

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  $291,990 New Construction

  • 3 Beds
  • 2 Baths
  • 1,672 Sq Ft

  ARIA Plan at Harmony at Lake Eloise, Winter Haven, FL 33880

  The Aria is one of our one-story floorplans featured in Harmony at Lake Eloise in Winter Haven, Florida. With multiple exteriors to choose from, the Aria is a popular home. Inside this 3-bedroom, 2-bathroom home, you’ll find 1,672 square feet of comfortable living. This all-concrete block constructed, one-story layout optimizes living space with an open concept kitchen overlooking the living

  D.R. Horton Builder

  1651 Hummingbird Rd Unit 36202790, Winter Haven, FL 33880
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  /30

  $283,990 New Construction

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

  4036 Giorgio Dr, Winter Haven, FL 33884

  Under Construction. This BEATIFUL HARPER Model home is located in the quaint town of Winter Haven. Ski capital & home of LEGOLAND. The NEWLY UPDATED HARPER has 4 bedrooms, 2baths & a 2-car garage - 1665 SqFt. This new model has an open floor plan with a spacious GREAT room off the kitchen to entertain & enjoy the company of your guests. You will love the split floor plan with beautiful & spacious

  Paul King DR HORTON REALTY OF CENTRAL FLORIDA LLC

  4036 Giorgio Dr, Winter Haven, FL 33884
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  /35

  $265,990 New Construction

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

  4517 Faith Dr, Lake Wales, FL 33859

  The property is located at 4517 Faith Drive LAKE WALES FL 33859 priced at 265990, the square foot and stories are 1328, 1.The number of bath is 2, halfbath is 0 there are 3 bedrooms and 2 garages. For more details please, call or email.

  D.R. Horton Builder

  4517 Faith Dr, Lake Wales, FL 33859
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  /52

  $224,900

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

  2348 Isle Royale Ct SE, Winter Haven, FL 33880

  Recently Fully Renovated Townhouse – Move-In Ready! Seller offering $4,000 credit toward buyer’s closing costs or interest rate buydown. Don’t miss your chance to own this completely remodeled 2-bedroom, 2.5-bathroom townhouse in Park Lake, now available at an unbeatable price! This home has been beautifully updated from top to bottom, offering modern style and worry-free living. All 3 bathrooms

  Fatma Higdon HIGDON HOMES REALTY LLC

  2348 Isle Royale Ct SE, Winter Haven, FL 33880
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  /17

  $290,000

  • 3 Beds
  • 2 Baths
  • 1,089 Sq Ft

  1516 Avenue D NE, Winter Haven, FL 33881

  Fully renovated 3BR/2BA home with an open space perfect for office or extra space located in Winter Haven NO HOA! New Roof, New AC, New Water Heater, New Flooring, New Kitchen Cabinets, updated bathrooms cabinets, and modern finishes throughout. Turn-key and move-in ready with a spacious yard and great location. Huge fenced backyard with banana trees Plus, NO HOA — enjoy more freedom and lower

  Karina Turcios LPT REALTY, LLC

  1516 Avenue D NE, Winter Haven, FL 33881
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  $259,000

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

  3161 Royal Tern Dr, Winter Haven, FL 33881

  Short Sale. One of the most sought-after floor plans, this 4-bedroom, 2-bathroom home boasts numerous charming features and is set on an oversized lot with no rear neighbors and a serene water view. As you enter, you'll find three spacious bedrooms and a modern bathroom. To the left, the inviting, contemporary kitchen showcases a large pantry offering ample storage space. The open dining area

  Krichely Gonzalez Rodriguez KELLER WILLIAMS ADVANTAGE III

  3161 Royal Tern Dr, Winter Haven, FL 33881
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  /20

  $259,900

  • 3 Beds
  • 2 Baths
  • 1,259 Sq Ft

  151 1st St S, Winter Haven, FL 33880

  Welcome to your move in ready dream home! Built in 2023 and still sparkling like new, this 3 bedroom , 2 bath beauty comes with an attached 1 car garage, sits at the at the end of of a peaceful dead end street in the highly sought after unincorporated Winter Haven-offering the perfect blend of privacy and convenience.Step inside to an open, light filled floor plan where every detail shines.

  Juan Garcia LIVE FLORIDA REALTY

  151 1st St S, Winter Haven, FL 33880
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  /21

  $288,600

  • 3 Beds
  • 2 Baths
  • 1,702 Sq Ft

  1150 High Seas St, Winter Haven, FL 33880

  Charm and curb appeal abound for this Winter Haven home! Step inside into the inviting foyer and into the well-appointed living room, positioned at the center of the home. The kitchen boasts a 4-piece appliance package, ample storage, hard surface countertops, and an eat-in dining room. This split floorplan offers the primary bedroom on one side of the home and two secondary on the other. Come

  Blake Keathley EVERYSTATE INC.

  1150 High Seas St, Winter Haven, FL 33880
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  $259,990 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,758 Sq Ft

  2735 Gladiola Rd, Winter Haven, FL 33884

  Under Construction. The Vale is one of our two-story townhome floorplans featured in our Harmony at Lake Eloise community in Winter Haven, Florida. Welcome to this stylish and modern townhome nestled in a serene community. Boasting three spacious bedrooms, two and a half luxurious baths, and a convenient two-car garage, this residence offers the perfect blend of comfort and functionality. This

  Paul King DR HORTON REALTY OF CENTRAL FLORIDA LLC

  2735 Gladiola Rd, Winter Haven, FL 33884
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  /21

  $294,990 New Construction

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

  6464 Domizio Dr, 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 Builder

  6464 Domizio Dr, Winter Haven, FL 33884
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  $290,900

  • 3 Beds
  • 2 Baths
  • 1,537 Sq Ft

  1518 Fuji Ct, Winter Haven, FL 33881

  Discover resort-style living in this charming 3-bedroom, 2-bath home built in 2023, nestled in the amenity-rich Villages at BridgeWater community. Boasting 1,537 sq ft of modern comfort on a 5,998 sq ft lot, enjoy an open floor plan with vaulted ceilings, a modern kitchen with large island, and a private primary suite. Community perks include a pool, fitness center, tennis courts, and a

  John Crusinberry MARK SPAIN REAL ESTATE

  1518 Fuji Ct, Winter Haven, FL 33881
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  $275,000

  • 4 Beds
  • 3 Baths
  • 2,040 Sq Ft

  1201 5th St NE, Winter Haven, FL 33881

  Well-maintained income property featuring a 3-bedroom / 2-bath main residence plus a detached 1-bedroom / 1-bath unit with private entrance. The property has been operated as a rental by the current owner and offers immediate income with upside potential. The main home features fresh interior paint, durable tile flooring throughout, a large indoor laundry/storage area, and recent upgrades

  George Waller, JR BTW PROPERTIES OF LAKELAND

  1201 5th St NE, Winter Haven, FL 33881
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  /31

  $299,990 New Construction

  • 4 Beds
  • 3 Baths
  • 1,988 Sq Ft

  3873 Giorgio Dr, Winter Haven, FL 33884

  Under Construction. Brand new, energy-efficient home available by Aug 2025! Open floor plan creates a unified living space with a large great room that overlooks the kitchen. Visit Villamar and explore new single-family homes for sale in Winter Haven, FL. Residents will have access to two resort-style amenity centers featuring a clubhouse, pool, and playground. Winter Haven is known for its

  Bryan Sumner MERITAGE HOMES OF FL REALTY

  3873 Giorgio Dr, Winter Haven, FL 33884
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  /16

  $279,990 New Construction

  • 4 Beds
  • 2 Baths
  • 1,874 Sq Ft

  6448 Domizio Dr, Winter Haven, FL 33884

  This expansive two-story home boasts a well-designed layout, featuring a first floor dedicated to shared living and entertaining. The open concept design seamlessly connects the kitchen, dining room and family room, with a patio extending the interior space outdoors. Upstairs, a spacious loft separates the three secondary bedrooms from the serene owner's suite. Completing the home is a convenient

  Lennar Builder

  6448 Domizio Dr, Winter Haven, FL 33884
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  /22

  $295,000 Open Sat 9AM - 7PM

  • 3 Beds
  • 2 Baths
  • 1,757 Sq Ft

  7010 Summit Cir, Winter Haven, FL 33884

  Welcome to this beautifully maintained property located at 7010 Summit Cir. The living room sets a welcoming tone with fresh interior paint lending a modern, clean feel, while tasteful partial flooring updates add subtle elegance. The kitchen is a chef’s dream featuring all stainless steel appliances and a layout designed for effortless daily cooking. The bedrooms offer a peaceful retreat,

  Karen Albright OPENDOOR BROKERAGE LLC

  7010 Summit Cir, Winter Haven, FL 33884
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  $294,366 Open Sun 10AM - 5PM

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

  1564 Leamington Ln, Winter Haven, FL 33884

  Under Construction. This 2200 square foot Home is a stunning home design that offers a perfect balance of style and functionality. With 4 bedrooms and 3 baths, this home provides ample space for comfortable living. The open-concept layout seamlessly connects the kitchen, dining area, and living room, creating a spacious and inviting atmosphere. The modern kitchen is equipped with high-quality

  Claudia Gutierrez ADAMS HOMES REALTY

  1564 Leamington Ln, Winter Haven, FL 33884
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  /25

  $249,990 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,673 Sq Ft

  2717 Gladiola Rd, Winter Haven, FL 33884

  Under Construction. This beautiful and spacious townhome is currently under construction and built entirely in concrete blockacross both stories, offering durability and peace of mind. Featuring 3 bedrooms, 2.5 bathrooms, and anupstairs laundry room, the layout is thoughtfully designed for modern living. Luxury vinyl flooring enhancesthe common areas, while plush carpeting adds

  Paul King DR HORTON REALTY OF CENTRAL FLORIDA LLC

  2717 Gladiola Rd, Winter Haven, FL 33884
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  /13

  $274,740 New Construction

  • 3 Beds
  • 2 Baths
  • 1,429 Sq Ft

  Belmont Plan at Peace Creek Reserve - Manor Key Collection, Winter Haven, FL 33884

  This new home is laid out on a single level for low maintenance living. Two secondary bedrooms share a bathroom in the hall at the front of the home, while the owner’s suite is tucked into the back corner with an attached bathroom and walk-in closet. Down the foyer is the open-concept living area, which includes a fully equipped kitchen, an intimate dining room and family room with patio access.

  Lennar Builder

  1108 Tyler Loop Unit 36037860, Winter Haven, FL 33884
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  /20

  $209,900

  • 3 Beds
  • 1 Bath
  • 1,008 Sq Ft

  520 35th St NW, Winter Haven, FL 33880

  Winter Haven Single Family Residential home, 3B/1ba offers a well landscaped Corner Lot. The Interior accommodates Electric AC & natural gas heat. This home still boasts original well maintained kitchen cabinets & oven appliances. The Exterior features are Concrete Block Detached storage/workshop 20x14’, covered carport 20x12’, exterior lighting, irrigation well, pole barn for RV parking 28x20’

  Wendy Gibbs WATSON & WATSON INC REALTORS

  520 35th St NW, Winter Haven, FL 33880
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  /15

  $210,000

  • 2 Beds
  • 2 Baths
  • 972 Sq Ft

  1213 8th St NW, Winter Haven, FL 33881

  Experience effortless living in this stunning, maintenance-free villa, perfectly located within a short walk of Publix, local dining, and serene lakes. This 2-bedroom, 2-bathroom home was beautifully upgraded in 2025 and features new LVP flooring. The heart of the home is the brand-new kitchen, boasting modern cabinets, sleek countertops, a stylish backsplash, bright LED lighting and a full suite

  Darrell Durham DARRELL RAY DURHAM

  1213 8th St NW, Winter Haven, FL 33881
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  /20

  $239,900

  • 4 Beds
  • 2 Baths
  • 1,599 Sq Ft

  306 Fern Rd, Winter Haven, FL 33880

  Short Sale. ***SHORT SALE *** BEAUTIFUL HOUSE COMPLETELY REMODELED, stainless steel appliances, wooden cabinets and whole house Laminate flooring.

  Consuelo Zea ZEA REALTY & ASSOCIATES

  306 Fern Rd, Winter Haven, FL 33880
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  /57

  $269,900 Open Sun 1PM - 3PM

  • 3 Beds
  • 3 Baths
  • 2,583 Sq Ft

  2410 Hartridge Point Dr W Unit 23, Winter Haven, FL 33881

  Water views take center stage in this beautifully positioned 3-bedroom, 3-bath condo overlooking Lake Hartridge on the Winter Haven Chain of Lakes. Located within a boutique 28-residence enclave, the home enjoys immediate proximity to the shared dock and uninterrupted lake views from both stories. The entry level opens to a bright, open-concept living and dining arrangement highlighted by a

  Rich Harbin COLDWELL BANKER REALTY

  2410 Hartridge Point Dr W Unit 23, Winter Haven, FL 33881
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  /5

  $259,900 New Construction

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

  353 Wharf Way, Winter Haven, FL 33881

  Brand-new 3-bedroom, open-layout 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 large walk-in wardrobe and a private en-suite bathroom including dual vanities, a decorative tiled shower, closeted toilet, and

  Highland Homes Builder

  353 Wharf Way, Winter Haven, FL 33881
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  $262,990 New Construction

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

  4249 Lester Dr, Lake Wales, FL 33859

  The property is located at 4249 Lester Drive LAKE WALES FL 33859 priced at 262990, the square foot and stories are 1328, 1.The number of bath is 2, halfbath is 0 there are 3 bedrooms and 2 garages. For more details please, call or email.

  D.R. Horton Builder

  4249 Lester Dr, Lake Wales, FL 33859
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  $242,990 New Construction

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

  4607 Linda Dr, Lake Wales, FL 33859

  The property is located at 4607 Linda Drive LAKE WALES FL 33859 priced at 232990, 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

  4607 Linda Dr, Lake Wales, FL 33859
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  $292,490 New Construction

  • 3 Beds
  • 2 Baths
  • 1,672 Sq Ft

  ARIA Plan at VillaMar, Winter Haven, FL 33884

  The Aria is one of our one-story floorplans featured in Villamar in Winter Haven, Florida. With multiple exteriors to choose from, the Aria is a popular home. Inside this 3-bedroom, 2-bathroom home, you’ll find 1,672 square feet of comfortable living. This all-concrete block constructed, one-story layout optimizes living space with an open concept kitchen overlooking the living area, dining room,

  D.R. Horton Builder

  3744 Giorgio Dr Unit 36202850, Winter Haven, FL 33884
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  /15

  $259,000

  • 3 Beds
  • 2 Baths
  • 1,102 Sq Ft

  1414 26th St NW, Winter Haven, FL 33881

  Charming Inwood home, located one block to lake Alfred. This 3 bedroom , 2 bathroom is perfect for 1st time home buyer or as an investment property. Its close to school and shopping. The drain field was done approximately 8 mths ago, New kitchen cabinets were put in, also both toilets and vanity, plus a new hot water tank. Please note that the hose will need a new A/C unit., however if the buyer

  Baijnauth Singh LIBERTY HOME SALES INC

  1414 26th St NW, Winter Haven, FL 33881
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  /27

  $267,618 New Construction

  • 3 Beds
  • 2 Baths
  • 1,407 Sq Ft

  4093 Penelope Ave, Lake Wales, FL 33859

  Want a move-in-ready home with quartz countertops, high ceilings, a covered lanai, and smart home technology — plus community amenities the whole family will love? Step into the Auburndale floor plan at Annabelle Estates by Dream Finders Homes, Builder of the Year. Imagine cooking in your modern kitchen with 42-inch cabinets, relaxing in your spacious living room with soaring ceilings, or

  Dream Finders Homes Builder

  4093 Penelope Ave, Lake Wales, FL 33859
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  /47

  $297,000

  • 4 Beds
  • 2 Baths
  • 1,851 Sq Ft

  1596 Leamington Ln, Winter Haven, FL 33884

  Short Sale. Motivated Sellers- Listing reflects appraisal price for Short Sale - Price is negotiable - Located in the growing Villa Mar community, this Cali floor plan offers 1,828 square feet of modern comfort in a location that blends resort-style amenities with everyday convenience. Residents enjoy a sparkling pool with a second on the way, a playground, and a planned dog park, creating an

  Christian Clay DALTON WADE INC

  1596 Leamington Ln, Winter Haven, FL 33884
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  /14

  $215,000

  • 3 Beds
  • 2 Baths
  • 1,097 Sq Ft

  3256 Avenue M NW, Winter Haven, FL 33881

  This charming Winter Haven home offers comfort, functionality, and a convenient location. Featuring a well-designed layout with spacious living areas and natural light throughout, this property is perfect for homeowners or investors alike.The kitchen provides ample cabinet space and flows easily into the main living area, creating an inviting space for everyday living and entertaining. The

  Phillip Randall DALTON WADE INC

  3256 Avenue M NW, Winter Haven, FL 33881
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  /39

  $219,000

  • 2 Beds
  • 2 Baths
  • 1,012 Sq Ft

  802 Magnolia Place, Winter Haven, FL 33884

  One or more photo(s) has been virtually staged. Waterfront condo on the Winter Haven Chain of Lakes! Spend every day surrounded by breathtaking sunrises and sunsets in this beautifully maintained ground-floor condo located within the highly desirable, gated waterfront community of Winterset on Lake Winterset. Perfectly positioned along the shores of the Winter Haven Chain of Lakes, this residence

  Michael Stone THE STONES REAL ESTATE FIRM

  802 Magnolia Place, Winter Haven, FL 33884
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  /16

  $275,900 New Construction

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

  Aurora Plan at VillaMar, Winter Haven, FL 33884

  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

  521 Vittorio Dr Unit 37315717, Winter Haven, FL 33884
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  /23

  $225,000 Open Sun 4PM - 6PM

  • 3 Beds
  • 2 Baths
  • 1,176 Sq Ft

  1250 31st St NW, Winter Haven, FL 33881

  Price Improvement — Exceptional Value!Beautifully renovated home tucked away in a quiet, no-HOA community and situated on a spacious corner lot offering added yard space and great curb appeal.This move-in ready property features an open-concept layout with modern finishes, abundant natural light, and fresh updates throughout. The spacious primary suite includes a private bath, and the

  Daryle Henry, Jr. LA ROSA REALTY CW PROPERTIES L

  1250 31st St NW, Winter Haven, FL 33881
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  /11

  $235,000

  • 2 Beds
  • 2 Baths
  • 1,536 Sq Ft

  2673 Rutledge Ct, Winter Haven, FL 33884

  Welcome to this charming 2 bedroom, 2 bathroom end unit townhome located in the desirable Rutledge Court community of Winter Haven. Designed for comfort and convenience, this well-maintained home features an open and functional layout ideal for everyday living or entertaining. The spacious living and dining areas flow seamlessly into the kitchen, offering ample cabinet space and room to gather.

  Chace Vaughn TOWN & COUNTRY REAL ESTATE

  2673 Rutledge Ct, Winter Haven, FL 33884
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  $249,900

  • 2 Beds
  • 2 Baths
  • 1,790 Sq Ft

  6825 S Lake Henry Dr NE, Winter Haven, FL 33881

  Enjoy true Florida lakefront living in this spacious 2-bedroom, 2-bath home offering almost 1800 square feet of heated living space, perfectly positioned on a waterfront lot with your own private dock, ideal for relaxing, fishing, or simply taking in the peaceful views of Lake Henry. Inside, the home features a large kitchen with a center island, stainless steel appliances including a built-in

  Patricia de Graaff RE/MAX HERITAGE PROFESSIONALS

  6825 S Lake Henry Dr NE, Winter Haven, FL 33881
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  $279,990 New Construction

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

  6444 Domizio 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

  6444 Domizio Dr, Winter Haven, FL 33884
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  /30

  $283,990 New Construction

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

  4032 Giorgio Dr, Winter Haven, FL 33884

  Under Construction. This BEATIFUL HARPER Model home is located in the quaint town of Winter Haven. Ski capital & home of LEGOLAND. The NEWLY UPDATED HARPER has 4 bedrooms, 2baths & a 2-car garage - 1665 Sq Ft. This new model has an open floor plan with a spacious GREAT room off the kitchen to entertain & enjoy the company of your guests. You will love the split floor plan with beautiful &

  Paul King DR HORTON REALTY OF CENTRAL FLORIDA LLC

  4032 Giorgio Dr, Winter Haven, FL 33884
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  /27

  $234,990 New Construction

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

  Pearson Plan, Lake Wales, FL 33859

  Annabelle Estates presents the Pearson, available to build in Winter Haven, Florida. This spacious all block construction townhome features 3 bedrooms and 2.5 bathrooms. When entering you are greeted with a long foyer and powder room or the option to go right upstairs. This home was designed with an open concept living feel. Enjoy the spacious kitchen with bar seating, and dining and living space

  4019 Penelope Ave Unit 37026745, Lake Wales, FL 33859
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  /42

  $225,000

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

  6827 S Lake Henry Dr, Winter Haven, FL 33881

  Discover lakeside living at its finest in this spacious 4-bedroom, 2-bath home located in the highly desirable 55+ community of Golf & Lake Estates in Winter Haven. Here, you own both the home and the land—a rare find in this area. Perfectly positioned with Lake Henry as your backyard, this home offers stunning water views from the large living area, where expansive windows fill the space with

  Samantha Conley GREEN STAR REALTY, INC.

  6827 S Lake Henry Dr, Winter Haven, FL 33881
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  /24

  $290,000

  • 3 Beds
  • 2 Baths
  • 2,015 Sq Ft

  584 Cody Caleb Dr, Winter Haven, FL 33884

  Discover this charming three-bedroom, two-bathroom residence in the desirable Savannah Estates, where comfort meets style. This inviting space features laminate flooring throughout, complemented by tile in the bathrooms. The open-concept design showcases a spacious kitchen, complete with ample cabinets, generous counter space, a breakfast bar, and stainless steel appliances, including a gas

  David Small KELLER WILLIAMS REALTY SMART 1

  584 Cody Caleb Dr, Winter Haven, FL 33884

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