Winter Haven, FL Homes

• 

  

  

  /40

  $235,000

  $20K PRICE DROP Under Contract

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

  3363 Livingston Way, Winter Haven, FL 33884

  Under contract-accepting backup offers. Beautifully updated cottage-style villa located in a desirable 55+ gated community. This fully remodeled home features ceramic tile flooring throughout, with the exception of the second bedroom. The spacious two-car garage includes a laundry area that can easily be enclosed for additional privacy or functionality. The appliances are approximately four years

  

  Beena Kokeram

  VREELAND REAL ESTATE LLC

  3363 Livingston Way, Winter Haven, FL 33884
• 

  

  

  /39

  Starting at $1,350 Per Month

  • 1 - 2 Beds

  200 Avenue C SW, Winter Haven, FL 33880

  Discover a living experience that moves with you. At Raindance, we have reimagined the modern residence as a sanctuary of light and fluid design. Each floor plan is a masterclass in spatial harmony, meticulously curated to balance expansive windows with intimate, designer-led interiors. Our commitment to excellence is woven into the very bones of the building, exceeding the highest energy

  Raindance

  

  200 Avenue C SW, Winter Haven, FL 33880
• 

  

  /2

  $308,900

  Sold Aug 13, 2026

  448 Ituna Cir, Winter Haven, FL 33881

  • 3 Beds
  • 2 Baths
  • 1,744 Sq Ft
  • Built 2026

  Last Sold Summary

  • 3% Below List Price
  • $177/SF
  • 26 Days On Market

  Current Estimated Value $316,877

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

  448 Ituna Cir, Winter Haven, FL 33881
• 

  

  /2

  Est $301,868

  Not Listed For Sale

  961 Oleander Dr SE, Winter Haven, FL 33880

  • 3 Beds
  • 2 Baths
  • 2,030 Sq Ft
  • Built 1956

  961 Oleander Dr SE, Winter Haven, FL 33880

  Last Sold Summary

  • 77 Days On Market

  Last Listing Agent Renee Butler BROKERS REALTY OF CENTRAL FLOR
• 

  

  

  /29

  $172,500

  $13K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,398 Sq Ft

  1026 Medinah Dr, Winter Haven, FL 33884

  Enjoy the Florida Country Club Lifestyle in this affordable and updated 2 bedroom 2 bath villa.Recent updates include new luxury vinyl flooring, new dishwasher and new microwave.MOVE IN CONDITION.The country club amenities include access to the clubhouse with bar and grill, jr. Olympic swimming pool and pickleball/tennis courts. The championship 18 hole golf course is open to the

  

  Steven Smith, PA

  LOCKHART & ASSOCIATES INC

  1026 Medinah Dr, Winter Haven, FL 33884
• 

  

  /21

  $1,400 Per Month

  • 2 Beds
  • 1 Bath
  • 880 Sq Ft
  • Townhouse for Rent

  5638 Struthers Ct, Winter Haven, FL 33884

  Beautifully renovated 1/2 Duplex for rent in SE Winter Haven. 2BR/1BA with Screened Porch (14x10). Ceramic Tile Flooring throughout with New Luxury Vinyl Flooring in the bedrooms. New kitchen with slow close wood cabinets, granite countertops and stainless appliances. Inside washer/dryer hookup. Lawn Service included with rent. Sorry, NO PETS!

  

  Amy Reynolds

  LOCKHART & ASSOCIATES INC

  5638 Struthers Ct, Winter Haven, FL 33884
• 

  /2

  $325,000

  Sold Nov 04, 2025

  3828 Eloise Estates Ct, Winter Haven, FL 33881

  • 4 Beds
  • 2 Baths
  • 1,867 Sq Ft
  • Built 2014

  Last Sold Summary

  • 2% Below List Price
  • $174/SF
  • 132 Days On Market

  Current Estimated Value $320,681

  Last Listing Agent Lamanda Jones CENTURY 21 WATSON & MYERS REALTY

  3828 Eloise Estates Ct, Winter Haven, FL 33881
• 

  /2

  Est $240,064

  Not Listed For Sale

  4007 Cypress Landing S, Winter Haven, FL 33884

  • 2 Beds
  • 2 Baths
  • 1,578 Sq Ft
  • Built 1986

  4007 Cypress Landing S, Winter Haven, FL 33884

  Last Sold Summary

  • 6 Days On Market

  Last Listing Agent Kathy Alexander CENTURY 21 WATSON & MYERS REALTY
• 

  

  /32

  $399,900

  $15K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,107 Sq Ft

  357 Ruby Lake Loop, Winter Haven, FL 33884

  Welcome to your dream home in the gated community of Ruby Lake! This beautifully designed 3-bedroom, 2-bath Cassidy “Ox” floor plan perfectly balances elegance and everyday comfort. Step inside to discover a spacious layout featuring formal living and dining rooms, along with a generous family room—ideal for both entertaining and relaxed living. The updated kitchen is truly the heart of the home,

  

  Steve Lockhart

  LOCKHART & ASSOCIATES INC

  357 Ruby Lake Loop, Winter Haven, FL 33884
• 

  

  /65

  Starting at $959 Per Month

  • Studio - 3 Beds

  7676 Carlton Arms Blvd, Winter Haven, FL 33884

  Carlton Arms of Winter Haven located on 122 acres of wooded lakefront property, offers country club living at many different rental rates. With its cascading fountains, beautifully landscaped grounds, peaceful woods and 5 freshwater lakes, this resort-style community provides every resident with professional management and maintenance that are trademarks of all Mahaffey planned properties.

  Carlton Arms Of Winter Haven

  

  7676 Carlton Arms Blvd, Winter Haven, FL 33884
• 

  $23,000

  Sold Apr 17, 2026

  0 Sunset Dr E, Winter Haven, FL 33881

  • Land
  • 1.77 Acres
  • $13,023 per Acre

  Last Sold Summary

  • 15% Below List Price
  • 107 Days On Market

  Last Listing Agent Silvio Islamaj ELIS Realty Advisors, LLC.

  0 Sunset Dr E, Winter Haven, FL 33881
• 

  /2

  Not Listed For Sale

  4151 Sprucewood St, Winter Haven, FL 33880

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft
  • Built 1982

  4151 Sprucewood St, Winter Haven, FL 33880

  Last Sold Summary

  • 107 Days On Market

  Last Listing Agent Brandy Duncan COLDWELL BANKER REALTY
• 

  

  /26

  $185,000

  • 2 Beds
  • 1 Bath
  • 934 Sq Ft

  790 Avenue Q SE, Winter Haven, FL 33880

  Welcome home to this well-maintained 2-bedroom, 1-bath patio home located in the 55+ community of Parkland Village. This move-in-ready home offers numerous recent updates, including a new roof (December 2025), new windows (2024–2025), new A/C (2022), and a new refrigerator and stove (2026), providing comfort and peace of mind for years to come. Inside, you'll find thoughtful features such as

  

  Amy Reynolds

  LOCKHART & ASSOCIATES INC

  790 Avenue Q SE, Winter Haven, FL 33880
• 

  

  /25

  $1,895 Per Month

  • 3 Beds
  • 2 Baths
  • 1,560 Sq Ft
  • House for Rent

  172 Inman Blvd, Winter Haven, FL 33881

  Move-In Special: 1st Month's Rent is Half-Off for leases beginning on or before September 15, 2026.Welcome to your LIKE-NEW home in the master planned community of INMAN GROVES! This stunning 3-Bedroom, 2-Bath, 2-car garage open floorplan is situated just a short drive from world class theme parks and attractions. Enjoy local restaurants, golf and shopping that are just a short drive

  

  Cheryl Rozanski

  JC FLORIDA REALTY LLC

  172 Inman Blvd, Winter Haven, FL 33881
• 

  /2

  $349,999

  Sold Mar 06, 2026

  5544 Taverna Loop, Winter Haven, FL 33884

  • 5 Beds
  • 3 Baths
  • 2,470 Sq Ft
  • Built 2025

  Last Sold Summary

  • 5% Below List Price
  • $142/SF
  • 10 Days On Market

  Current Estimated Value $349,351

  Last Listing Agent Dale Human CASA FRESCA REALTY

  5544 Taverna Loop, Winter Haven, FL 33884
• 

  /2

  Not Listed For Sale

  4076 Rolling Oaks Dr, Winter Haven, FL 33880

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 1983

  4076 Rolling Oaks Dr, Winter Haven, FL 33880

  Last Sold Summary

  • 3 Days On Market

  Last Listing Agent Kathy Devor COLDWELL BANKER REALTY
• 

  

  /19

  $66,900

  • 2 Beds
  • 2 Baths
  • 1,144 Sq Ft

  56 Greenview Dr, Winter Haven, FL 33881

  WELCOME - SPACIOUS, MOVE-IN READY & BEAUTIFULLY MAINTAINED! Come see this spacious 2-bedroom, 2-bath home offering 1,144 square feet of comfortable living space in the desirable 55+ Swiss Golf & Tennis community, on an exterior lot with no rear neighbors, near a pond and walking path. This well-maintained home offers a wonderful combination of updates, comfort and extras, making it an excellent

  

  Cindy Minnick

  Sun Resales, Inc.

  56 Greenview Dr, Winter Haven, FL 33881
• 

  

  /35

  Starting at $1,099 Per Month

  • 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

  Haven at Lake Deer

  

  350 24th St NW, Winter Haven, FL 33880
• 

  

  /57

  $53,500

  Sold Jan 15, 2026

  109 Rigi Slope Dr, Winter Haven, FL 33881

  • 2 Beds
  • 2 Baths
  • 1,344 Sq Ft
  • Built 1983

  Last Sold Summary

  • 11% Below List Price
  • $40/SF
  • 204 Days On Market

  Last Listing Agent Chrissy Walter Sunset Home Sales

  109 Rigi Slope Dr, Winter Haven, FL 33881
• 

  /2

  Not Listed For Sale

  6059 Southern Oaks Dr SE, Winter Haven, FL 33884

  • 2 Beds
  • 2 Baths
  • 1,152 Sq Ft
  • Built 1985

  6059 Southern Oaks Dr SE, Winter Haven, FL 33884

  Last Sold Summary

  • 162 Days On Market

  Last Listing Agent Michelle Armbruster LOCKHART & ASSOCIATES INC
• 

  

  /16

  $109,999

  $15K PRICE DROP Pending

  • 2 Beds
  • 1 Bath
  • 840 Sq Ft

  900 Avenue Z SE Unit D6, Winter Haven, FL 33880

  Welcome to easy lakefront living in the highly desirable Sandy Cove community on the Winter Haven Chain of Lakes! This beautiful 2nd floor condo offers low-maintenance living perfect for a full-time residence, seasonal retreat, or investment opportunity. This 2-bedroom, 1-bath condo features a bright and functional layout with comfortable living and dining spaces designed for everyday living and

  

  Samantha Whitmore

  WHITMORE PROPERTIES

  900 Avenue Z SE Unit D6, Winter Haven, FL 33880
• 

  

  /47

  $1,700 Per Month

  • 2 Beds
  • 2 Baths
  • 1,078 Sq Ft
  • Condo for Rent

  715 Magnolia Place Unit 715, Winter Haven, FL 33884

  Gorgeous sunset views over Lake Winterset... this is the kind of rental you don’t come across often. Located in the gated Winterset community, this well-maintained 2-bedroom, 2-bath upstairs condo with a private one-car garage offers easy, low-maintenance lakeview living. Inside, you’ll find an open and airy layout with vaulted ceilings, skylights, and large sliding glass doors that bring in tons

  

  CarLee Marchetti

  STAR REALTY OF WINTER HAVEN

  715 Magnolia Place Unit 715, Winter Haven, FL 33884
• 

  /2

  $525,000

  Sold Dec 16, 2025

  1301 Hidden Creek Ct, Winter Haven, FL 33880

  • 3 Beds
  • 2 Baths
  • 2,278 Sq Ft
  • Built 1998

  Last Sold Summary

  • $230/SF
  • 13 Days On Market

  Current Estimated Value $527,788

  Last Listing Agent Brock Jennings THE MARKET REALTY COMPANY

  1301 Hidden Creek Ct, Winter Haven, FL 33880
• 

  /2

  Est $158,497

  Not Listed For Sale

  262 Ware Ave NE, Winter Haven, FL 33881

  • 2 Beds
  • 1 Bath
  • 816 Sq Ft
  • Built 1963

  262 Ware Ave NE, Winter Haven, FL 33881

  Last Sold Summary

  • 229 Days On Market

  Last Listing Agent Alexandre Zapparoli LLC WRA BUSINESS & REAL ESTATE
• 

  

  /31

  $450,000

  $75K PRICE DROP Under Contract

  • 4 Beds
  • 3.5 Baths
  • 2,921 Sq Ft

  184 Lake Otis Rd, Winter Haven, FL 33884

  Under contract-accepting backup offers. Located in the highly sought-after gated community of Lakewood, this beautifully maintained home offers 4 bedrooms and 3.5 bathrooms, set on a lush, manicured lot with mature trees and attractive landscaping. Inside, you’ll find rich wood flooring throughout the spacious living and dining areas, as well as the kitchen and family room—perfect for both

  

  Steve Lockhart

  LOCKHART & ASSOCIATES INC

  184 Lake Otis Rd, Winter Haven, FL 33884
• 

  

  /47

  Starting at $1,200 Per Month

  • 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.

  The Jade

  

  1150 3rd St SW, Winter Haven, FL 33880
• 

  /2

  $273,000

  Sold Dec 03, 2025

  4070 Island Lakes Dr, Winter Haven, FL 33881

  • 4 Beds
  • 2 Baths
  • 1,860 Sq Ft
  • Built 2011

  Last Sold Summary

  • 28% Below List Price
  • $147/SF
  • 400 Days On Market

  Current Estimated Value $282,222

  Last Listing Agent Natalie Rivera VESTI LLC

  4070 Island Lakes Dr, Winter Haven, FL 33881
• 

  

  /44

  Est $309,434

  Not Listed For Sale

  7146 Summit Dr, Winter Haven, FL 33884

  • 3 Beds
  • 2 Baths
  • 1,842 Sq Ft
  • Built 2004

  7146 Summit Dr, Winter Haven, FL 33884

  Last Sold Summary

  • 38 Days On Market

  Last Listing Agent Jordan Prais 54 REALTY LLC
• 

  

  /29

  $149,900

  • 3 Beds
  • 2 Baths
  • 1,218 Sq Ft

  333 Lake Howard Dr NW Unit 211B, Winter Haven, FL 33880

  Remodeled and updated 2nd floor condo with picturesque views of the pool and lush landscaping. This 3 bedroom unit is ready for immediate occupancy. Recent updates include fresh interior paint, new flooring, new kitchen cabinets and solid surface counters.This established 55 and over community is nestled on the shores of Lake Howard on the famous Chain of Lakes and includes a community boat

  

  Steven Smith, PA

  LOCKHART & ASSOCIATES INC

  333 Lake Howard Dr NW Unit 211B, Winter Haven, FL 33880
• 

  

  /37

  $2,150 Per Month

  • 4 Beds
  • 2.5 Baths
  • 1,874 Sq Ft
  • House for Rent

  1938 Sarah St, Winter Haven, FL 33884

  Enjoy this 2025 Lennar-built home, nestled in the growing community of Peace Creek Reserve! This two-story home blends modern finishes with a spacious layout designed for everyday living and comfort. Step into a long foyer that opens to an inviting great room, where the kitchen overlooks the living and dining areas—perfect for gatherings or cozy nights in. Durable ceramic tile flooring spans the

  

  CarLee Marchetti

  STAR REALTY OF WINTER HAVEN

  1938 Sarah St, Winter Haven, FL 33884
• 

  

  /21

  $299,490

  Sold May 28, 2026

  6216 Botticella Blvd, Winter Haven, FL 33884

  • 5 Beds
  • 2 Baths
  • 2,326 Sq Ft
  • Built 2026

  Move in Ready Sold Summary

  • $129/SF
  • 7 Days On Market

  Lennar Villa Mar

  6216 Botticella Blvd, Winter Haven, FL 33884
• 

  /2

  Est $240,762

  Not Listed For Sale

  1825 Wallace Manor Ln, Winter Haven, FL 33880

  • 3 Beds
  • 2 Baths
  • 1,184 Sq Ft
  • Built 2018

  1825 Wallace Manor Ln, Winter Haven, FL 33880

  Last Sold Summary

  • 42 Days On Market

  Last Listing Agent Casandra Vann KELLER WILLIAMS REALTY
• 

  

  /33

  $69,999

  • 2 Beds
  • 2 Baths

  645 Century Ln, Winter Haven, FL 33881

  Welcome to this beautifully updated and spacious 2-bedroom, 2-bath home offering 1,296 sq ft of comfortable living! From the moment you walk in, you'll appreciate the open-concept layout. The kitchen features warm wood cabinetry with plenty of storage, while the home boasts newer flooring installed in 2022 for a fresh, modern feel throughout. The primary suite is a true retreat, highlighted by a

  

  Cindy Minnick

  Sun Resales, Inc.

  645 Century Ln, Winter Haven, FL 33881
• 

  

  /15

  Starting at $997 Per Month

  • 1 - 3 Beds

  200 Avenue K SE, Winter Haven, FL 33880

  Welcome to Briarcrest at Winter Haven Apartments, ideally located near downtown Winter Haven, FL where convenience meets comfort in a picturesque setting. Choose from our spacious and versatile one, two, and three-bedroom floor plans, each thoughtfully designed to suit diverse lifestyles. Our community boasts not just one, but two sparking pools for residents to unwind and enjoy Florida's

  Briarcrest at Winter Haven

  

  200 Avenue K SE, Winter Haven, FL 33880
• 

  

  /16

  $272,490

  Sold Apr 08, 2026

  2154 Chris Dr, Winter Haven, FL 33884

  • 4 Beds
  • 2 Baths
  • 1,880 Sq Ft
  • Built 2026

  Move in Ready Sold Summary

  • 5% Below List Price
  • $145/SF
  • 38 Days On Market

  Current Estimated Value $275,224

  2154 Chris Dr, Winter Haven, FL 33884
• 

  

  /24

  Est $285,620

  Not Listed For Sale

  184 Fall Glo Rd, Winter Haven, FL 33880

  • 4 Beds
  • 2 Baths
  • 1,867 Sq Ft
  • Built 2018

  184 Fall Glo Rd, Winter Haven, FL 33880

  Last Sold Summary

  • 206 Days On Market

  Last Listing Agent Vivian Ortiz OAK AVENUE REAL ESTATE LLC
• 

  

  /23

  $269,900

  $30K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,355 Sq Ft

  362 Holly Ridge Rd, Winter Haven, FL 33880

  Discover the perfect blend of style, comfort, and peace of mind in this beautifully updated 3-bedroom, 2-bath home that’s ready for you to move right in. Thoughtfully refreshed with fresh interior and exterior paint, this home offers a bright, welcoming atmosphere from the moment you arrive.The heart of the home is the stunning kitchen, featuring gorgeous granite countertops, sleek

  

  Katrina Asher

  MILLSHIRE REALTY

  362 Holly Ridge Rd, Winter Haven, FL 33880
• 

  

  /15

  $1,200 Per Month

  • 2 Beds
  • 2 Baths
  • 930 Sq Ft
  • Condo for Rent

  8402 Waterview Way Unit 8402, Winter Haven, FL 33884

  2 bedroom 2 bath ground floor condo located in gated Winterset on the Shores of Lake Winterset.Enjoy a community pool, club house, tennis courts and community boat ramp.Partially furnished or furniture can be removed.

  

  Steven Smith, PA

  LOCKHART & ASSOCIATES INC

  8402 Waterview Way Unit 8402, Winter Haven, FL 33884
• 

  

  /28

  $279,490

  Sold Sep 24, 2025

  4144 Giorgio Dr, Winter Haven, FL 33884

  • 4 Beds
  • 2 Baths
  • 1,665 Sq Ft
  • Built 2025

  Move in Ready Sold Summary

  • $168/SF
  • 13 Days On Market

  D.R. Horton VillaMar

  4144 Giorgio Dr, Winter Haven, FL 33884
• 

  

  /52

  Est $316,542

  Not Listed For Sale

  208 Fall Glo Rd, Winter Haven, FL 33880

  • 4 Beds
  • 3 Baths
  • 2,526 Sq Ft
  • Built 2018

  208 Fall Glo Rd, Winter Haven, FL 33880

  Last Sold Summary

  • 68 Days On Market

  Last Listing Agent David Small KELLER WILLIAMS REALTY SMART 1

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