Winter Haven, FL Homes

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  /45

  $179,900

  • 2 Beds
  • 2 Baths
  • 2,208 Sq Ft

  194 Fairway Cir, Winter Haven, FL 33881

  This beautifully updated 2-bedroom, 2-bathroom unfurnished home offers modern comfort and timeless charm, nestled on a spacious private lot along the 14th hole of the golf course. Step inside to discover a fully renovated interior featuring luxury finishes throughout. A chef's dream kitchen, boasting a 5' double-door pantry, additional storage closet with shelving, tile backsplash, deep

  

  Cindy Minnick

  Sun Resales, Inc.

  (863) 336-6201

  194 Fairway Cir, Winter Haven, FL 33881
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  /55

  $1,097 - $2,405 per month

  The Carlton at Lake Dexter

  1 - 3 Beds

  1015 Mahaffey Rd, Winter Haven, FL 33884

  A luxury rental lakefront apartment community in Winter Haven, Florida. Accepting leases now.

  1015 Mahaffey Rd, Winter Haven, FL 33884
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  /28

  $279,490 Sold Sep 24, 2025

  • 1,665 Sq Ft
  • $168/SF

  • 4 Beds
  • 2 Baths
  • Built 2025

  4144 Giorgio Dr, Winter Haven, FL 33884

  The property is located at 4144 Giorgio Drive WINTER HAVEN FL 33884 priced at 279490, 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

  4144 Giorgio Dr, Winter Haven, FL 33884
• 

  

  /2

  Est $225,157 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,191 Sq Ft

  1739 Avenue C NE, Winter Haven, FL 33881

  1739 Avenue C NE, Winter Haven, FL 33881
• 

  

  

  /32

  $252,000

  • 3 Beds
  • 2 Baths
  • 1,252 Sq Ft

  3510 Majesty Loop, Winter Haven, FL 33880

  Welcome to this beautifully designed contemporary home, nestled in a quiet neighborhood in Central Florida—known as the Water Skiing Capital of the World. Offering both comfort and convenience, this home is just a short drive from world-famous theme parks such as Disney, Universal, and LegoLand, and only about 1.5 hours from the stunning beaches on either side of the State.As you step onto

  

  Russ Yerton

  ELEVATE REAL ESTATE BROKERS

  (863) 349-3859

  3510 Majesty Loop, Winter Haven, FL 33880
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  /12

  $1,695 per month

  • 2 Beds
  • 2 Baths
  • 1,398 Sq Ft
  • Apartment for Rent

  1062 Medinah Dr, Winter Haven, FL 33884

  Great Rental in Cypresswood. We think this unit is in the best location of all the Villas in the area. Come take a look for yourself!

  Doug DeWitt NEW HOME ADVANTAGE LLC

  1062 Medinah Dr, Winter Haven, FL 33884
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  /71

  $44,900 Sold Aug 29, 2025

  654 Century Ln, Winter Haven, FL 33881

  • 2 Beds
  • 2 Baths
  • 1,140 Sq Ft
  • Built 1988

  Last Sold Summary

  • 44% Below List Price
  • $39/SF
  • 225 Days On Market

  Last Listing Agent Cynthia Cole Sunset Home Sales

  654 Century Ln, Winter Haven, FL 33881
• 

  /2

  Est $276,097 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,437 Sq Ft

  215 Kingshill Ct SE, Winter Haven, FL 33884

  215 Kingshill Ct SE, Winter Haven, FL 33884
• 

  

  /30

  $154,500

  • 2 Beds
  • 2 Baths
  • 1,289 Sq Ft

  146 Winter Ridge Dr Unit 160, Winter Haven, FL 33881

  Beautiful two-bedroom, two-bath condominium in the desirable waterfront community of Winter Ridge with direct access to Lake Smart on the Chain of Lakes. This corner end unit features laminate flooring throughout the main living areas and carpet in both bedrooms. Open living and dining area with a galley-style kitchen offering plenty of cabinets, a walk-in pantry, and a washer and dryer. The

  

  Amy Reynolds

  LOCKHART & ASSOCIATES INC

  (863) 282-7696

  146 Winter Ridge Dr Unit 160, Winter Haven, FL 33881
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  /66

  $1,200 - $1,650 per month

  The Jade

  1 - 2 Beds

  1150 3rd St SW, Winter Haven, FL 33880

  The Best Amenities in TownThe Jade offers the most comprehensive amenity package in town, offering an unmatched blend of luxury, comfort, and convenience at one inclusive price—no other apartment complex nearby provides such a diverse range of options under one roof.

  1150 3rd St SW, Winter Haven, FL 33880
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  /2

  $350,990 Sold Dec 26, 2024

  1957 Sarah St, Winter Haven, FL 33884

  • 4 Beds
  • 3 Baths
  • 2,174 Sq Ft
  • Built 2024

  Last Sold Summary

  • 3% Below List Price
  • $161/SF
  • 13 Days On Market

  Current Estimated Value $329,662

  Last Listing Agent Ben Goldstein LENNAR REALTY

  1957 Sarah St, Winter Haven, FL 33884
• 

  /2

  Est $184,298 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,445 Sq Ft

  717 Crestwood Dr, Winter Haven, FL 33881

  717 Crestwood Dr, Winter Haven, FL 33881
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  /42

  $298,000

  • 3 Beds
  • 1.5 Baths
  • 1,852 Sq Ft

  119 Doll Dr, Winter Haven, FL 33884

  This is a solid block home featuring 3 bedrooms and 1.5 bathrooms in a convenient and well-established neighborhood. Enjoy canal access to Lake Daisy, perfect for kayaking, pedal boarding, fishing, or relaxing by the water. The home offers peace of mind with a brand-new 30-year architectural shingle roof, a major upgrade for durability and insurance savings. Ideally located near shopping, dining,

  

  Clarisa Moody

  MARZUCCO REAL ESTATE

  (863) 265-4259

  119 Doll Dr, Winter Haven, FL 33884
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  /33

  $1,695 per month

  • 3 Beds
  • 2.5 Baths
  • 1,625 Sq Ft
  • House for Rent

  2630 Tanoak Terrace, Winter Haven, FL 33881

  One or more photo(s) has been virtually staged. Welcome home to this charming 3-bedroom, 2.5-bath residence designed with both style and functionality in mind. The open-concept layout welcomes you with a bright and spacious living area, a sleek modern kitchen, and an inviting dining space—perfect for entertaining or enjoying quality family time. Upstairs, you’ll find generously sized bedrooms,

  Jacob Hara TRANSCEND REALTY

  2630 Tanoak Terrace, Winter Haven, FL 33881
• 

  /2

  $260,000 Sold Apr 17, 2025

  26 Casarena Ct, Winter Haven, FL 33881

  • 2 Beds
  • 3 Baths
  • 2,045 Sq Ft
  • Built 1985

  Last Sold Summary

  • 9% Below List Price
  • $127/SF
  • 12 Days On Market

  Current Estimated Value $254,581

  Last Listing Agent Cheryl Brewer COLDWELL BANKER REALTY

  26 Casarena Ct, Winter Haven, FL 33881
• 

  /2

  Est $240,729 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,580 Sq Ft

  290 36th St NW, Winter Haven, FL 33880

  290 36th St NW, Winter Haven, FL 33880
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  /27

  $84,900

  • 2 Beds
  • 2 Baths
  • 1,296 Sq Ft

  645 Century Ln, Winter Haven, FL 33881

  Experience comfortable living in this beautifully updated two-bedroom, two-bath home. Enjoy brand-new flooring installed in 2022, enhancing the modern feel throughout. The spacious bonus room offers versatile options for your lifestyle needs, while the large shed provides ample storage. Relax in the inviting Florida room, equipped with an efficient HVAC system for year-round comfort. The primary

  

  Cindy Minnick

  Sun Resales, Inc.

  (863) 431-1518

  645 Century Ln, Winter Haven, FL 33881
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  /65

  $859 - $2,006 per month

  Carlton Arms of Winter Haven

  Studio - 3 Beds

  7676 Carlton Arms Blvd, Winter Haven, FL 33884

  *Call or email for today’s availabilityConveniently located on SR540/US27, Carlton Arms of Winter Haven offers 122 wooded lakefront acres with beautiful grounds, free amenities and great service! Country club living at great monthly rents.

  7676 Carlton Arms Blvd, Winter Haven, FL 33884
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  /2

  $245,000 Sold Mar 17, 2025

  1734 Avenue C NE, Winter Haven, FL 33881

  • 3 Beds
  • 2 Baths
  • 1,176 Sq Ft
  • Built 1989

  Last Sold Summary

  • 2% Below List Price
  • $208/SF
  • 28 Days On Market

  Current Estimated Value $232,653

  Last Listing Agent Keith St. Onge LA ROSA REALTY PRESTIGE

  1734 Avenue C NE, Winter Haven, FL 33881
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  /2

  Est $493,544 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,125 Sq Ft

  23 Oakwood Rd, Winter Haven, FL 33880

  23 Oakwood Rd, Winter Haven, FL 33880
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  /53

  $225,000

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

  703 Magnolia Place, Winter Haven, FL 33884

  PRICE ADJUSTED AND READY FOR ITS NEW OWNER! Welcome to this beautifully updated first-floor condo with stunning sunset views over Lake Winterset. With a recent price improvement, this spacious two-bedroom, two-bath home with a one-car garage offers incredible value, modern updates, and resort-style amenities in a highly desirable lakefront community. Inside, you’ll find brand-new tile flooring in

  

  Mabel Vassallo

  CENTURY 21 MYERS REALTY

  (863) 456-7957

  703 Magnolia Place, Winter Haven, FL 33884
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  /37

  $4,000 per month

  • 4 Beds
  • 4 Baths
  • 3,330 Sq Ft
  • House for Rent

  2445 Gerber Dairy Rd, Winter Haven, FL 33880

  Move in ready, Furnished rental ready to move in on Oct 15th. Peaceful and serene ranch tucked away from the hustles of the city. Walk into the entry foyer with 12 ft ceiling, open family room, kitchen with granite counter tops and new appliances. It's custom built to allow maximum open space for large gatherings. Fifth bedroom is currently used as theatre room. All bedrooms have bathrooms which

  Dylan Hamilton WEICHERT REALTORS-BRANDON REALTY

  2445 Gerber Dairy Rd, Winter Haven, FL 33880
• 

  /2

  $400,000 Sold Apr 25, 2025

  1116 Cypress Point W, Winter Haven, FL 33884

  • 3 Beds
  • 2 Baths
  • 2,030 Sq Ft
  • Built 1978

  Last Sold Summary

  • $197/SF
  • 6 Days On Market

  Current Estimated Value $398,498

  Last Listing Agent Erin Floyd COLDWELL BANKER REALTY

  1116 Cypress Point W, Winter Haven, FL 33884
• 

  /2

  Est $512,806 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,382 Sq Ft

  1865 Woodpointe Dr, Winter Haven, FL 33884

  1865 Woodpointe Dr, Winter Haven, FL 33884
• 

  

  /100

  $284,900

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

  5325 Nicklaus Dr, Winter Haven, FL 33884

  Pride of ownership is evident in this well-maintained "snowbird" owned Caribbean floor plan home. The curb appeal comes from the quality landscaping, which includes tasteful plantings, palms, and a paver walk and drive. All the landscaping is "watered" by an automatic irrigation system. The home has many special features and recent upgrades that frees up the new owners. The roof was replaced in

  

  Michael Krigelski

  A+ REALTY LLC

  (863) 663-6182

  5325 Nicklaus Dr, Winter Haven, FL 33884
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  /46

  $1,299 - $2,139 per month

  Dream Winter Haven

  1 - 3 Beds

  5004 Dream Dr, Winter Haven, FL 33881

  Embrace the art of living fully at Dream Winter Haven, where each day is a masterpiece waiting to be painted. Here, life is about more than just a home—it's about thriving in a community designed to enrich your every experience. Discover the charm of brand-new luxury 1, 2, and 3-bedroom apartments, complemented by resort-style amenities that encourage you to live fully. Set in the heart of Winter

  5004 Dream Dr, Winter Haven, FL 33881
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  /24

  $327,990 Sold Nov 03, 2025

  • 1,761 Sq Ft
  • $186/SF

  • 3 Beds
  • 2 Baths
  • Built 2025

  3450 Evening Star Dr, Winter Haven, FL 33881

  Entering from the front porch, you step into the foyer, where two bedrooms greet you at the front of the home—each featuring a walk-in closet and sharing a full bath. As you continue down the hallway, you'll pass a coat closet, the laundry room, and access to the two-car garage. The layout then opens into the kitchen, family room, and dining area, creating a welcoming space for everyday living. A

  Starlight Homes

  3450 Evening Star Dr, Winter Haven, FL 33881
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  /2

  Est $286,542 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,716 Sq Ft

  802 Reflections Loop E, Winter Haven, FL 33884

  802 Reflections Loop E, Winter Haven, FL 33884
• 

  

  /14

  $128,900

  • 2 Beds
  • 1 Bath
  • 826 Sq Ft

  1100 Martinique Dr Unit 203, Winter Haven, FL 33884

  SO close to HWY 27, Legoland, shopping, golf, and MORE! This beautifully renovated 2/1 condo comes complete with all new appliance suite, including a gas range for the home chef in you! (Gad is included in your HOA) Brand new cabinetry, ceiling fans, laminate flooring, and so much more. There are no age restrictions, and the LOW HOA covers exterior maintenance, grounds maintenance, gas for

  

  Cyleste Goodson

  FLORIDA REAL ESTATE COMPANY

  (863) 328-4197

  1100 Martinique Dr Unit 203, Winter Haven, FL 33884
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  /12

  $1,100 per month

  • 1 Bed
  • 1 Bath
  • 475 Sq Ft
  • Condo for Rent

  1103 Cypress Gardens Blvd Unit C-106, Winter Haven, FL 33884

  1 bedroom 1 bath ground floor condo with access to Lake Roy on the famous Winter Haven Chain of Lakes.New Luxury Vinyl Plank Flooring and fresh interior paint.

  Steven Smith, PA LOCKHART & ASSOCIATES INC

  1103 Cypress Gardens Blvd Unit C-106, Winter Haven, FL 33884
• 

  /2

  $339,900 Sold Apr 07, 2025

  444 Ituna Cir, Winter Haven, FL 33881

  • 4 Beds
  • 2.5 Baths
  • 2,029 Sq Ft
  • Built 2024

  Last Sold Summary

  • 14% Below List Price
  • $168/SF
  • 103 Days On Market

  Last Listing Agent George Lindsey, III CAMBRIDGE REALTY OF CENTRAL FL

  444 Ituna Cir, Winter Haven, FL 33881
• 

  /2

  Est $224,267 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,652 Sq Ft

  2231 Devonshire Place, Winter Haven, FL 33880

  2231 Devonshire Place, Winter Haven, FL 33880
• 

  

  /30

  $34,500

  • 2 Beds
  • 2 Baths
  • 915 Sq Ft

  590 Century Dr, Winter Haven, FL 33881

  Welcome to your move-in ready 2-bedroom, 2-bath home that lives larger than its footprint. Bring your own personal style and make it truly feel like home in the 915 sq ft of comfortable neutral living space. Recent updates include fresh interior paint, a renovated kitchen with island, wood cabinets and durable butcher block countertops, and luxury vinyl plank flooring throughout. Systems and

  

  Cindy Minnick

  Sun Resales, Inc.

  (863) 300-0634

  590 Century Dr, Winter Haven, FL 33881
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  /35

  $1,099 - $1,549 per month

  Haven at Lake Deer

  Studio - 2 Beds

  350 24th St NW, Winter Haven, FL 33880

  Haven at Lake Deer is the retreat you've been looking for in Winter Haven, FL. Our lakeside community features studio, one and two bedroom homes complete with patios, wood-style flooring, and upgraded kitchens. What's more, as a member of the community you'll also have access to our sparkling swimming pools and a 24-hour gym. At Haven at Lake Deer, you're guaranteed to find a place to live with a

  350 24th St NW, Winter Haven, FL 33880
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  /12

  $265,000 Sold Sep 23, 2025

  • 1,269 Sq Ft
  • $209/SF

  • 3 Beds
  • 2 Baths
  • Built 2025

  4981 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

  4981 Kaia Ave, Winter Haven, FL 33884
• 

  /2

  Est $211,735 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,292 Sq Ft

  1445 10th Ct NE, Winter Haven, FL 33881

  1445 10th Ct NE, Winter Haven, FL 33881
• 

  

  /36

  $281,500 Pending

  • 2 Beds
  • 2 Baths
  • 1,850 Sq Ft

  1663 W Lake Cannon Dr NW, Winter Haven, FL 33881

  Under contract-accepting backup offers. ANOTHER PRICE REDUCTION!! Enjoy peaceful lake views from this beautifully updated 2-bedroom, 2-bathroom home overlooking Lake Cannon. Freshly painted with all-new luxury vinyl flooring throughout, this home offers both comfort and style. A spacious Living Room provides a clear view of the lake, while the Bonus Room offers flexible space for an office, den,

  

  Amy Reynolds

  LOCKHART & ASSOCIATES INC

  (863) 343-1270

  1663 W Lake Cannon Dr NW, Winter Haven, FL 33881
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  /42

  $2,100 per month

  • 3 Beds
  • 2 Baths
  • 1,950 Sq Ft
  • House for Rent

  512 Mckenna Dr, Winter Haven, FL 33881

  Move-in ready 3 bedroom, 2 bath single-family home available for rent in a quiet and desirable Winter Haven community. This spacious home features an open floor plan, tile and vinyl flooring, and a bright living area with plenty of natural light. The modern kitchen comes fully equipped with refrigerator, range, microwave, dishwasher, and disposal, plus the home includes a washer and dryer for

  Gerd Schwarzenberg IG REAL ESTATE SERVICES LLC

  512 Mckenna Dr, Winter Haven, FL 33881
• 

  

  /5

  $244,990 Sold Aug 29, 2025

  • 1,604 Sq Ft
  • $153/SF

  • 3 Beds
  • 2 Baths
  • Built 2025

  230 Turtle Bay Ave, Winter Haven, FL 33881

  Move-in ready, 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

  230 Turtle Bay Ave, Winter Haven, FL 33881
• 

  /2

  Est $378,242 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,482 Sq Ft

  4442 Mandolin Blvd, Winter Haven, FL 33884

  4442 Mandolin Blvd, Winter Haven, FL 33884

Showing Results 81 - 120, Page 3 of 18