Winter Haven, FL Homes

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  /30

  $54,900

  $35K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,456 Sq Ft

  385 Tennis Ln, Winter Haven, FL 33881

  Community living in a great location with tons of activities in the very popular 55+ gated community of Swiss Golf and Tennis in Winter Haven, FL. This 1989 Homes of Merit 2 bedroom, 2 bath has a nice roomy entryway with laminate flooring throughout and the layout is spacious and open. You will find updates in the bathrooms with newer sink, flooring, commode, faucet, and lighting. The living room

  

  Cindy Minnick

  Sun Resales, Inc.

  385 Tennis Ln, Winter Haven, FL 33881
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  /24

  Starting at $1,365 Per Month

  • 2 Beds

  2000 15th Ct NW, Winter Haven, FL 33881

  Aqua Apartment Homes in Winter Haven, FL offers comfortable apartment living with on-site conveniences.Residents can enjoy a pool and an outdoor area, while pet owners benefit from a dedicated dog park and a pet-friendly community. Practical features include parking and a community laundry room for added convenience.For more information, visit us at

  Aqua Apartment Homes

  

  2000 15th Ct NW, Winter Haven, FL 33881
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  /2

  $189,900

  Sold Aug 14, 2026

  6346 Bayberry Blvd NE, Winter Haven, FL 33881

  • 3 Beds
  • 2 Baths
  • 1,440 Sq Ft
  • Built 2005

  Last Sold Summary

  • 12% Below List Price
  • $132/SF
  • 253 Days On Market

  Last Listing Agent Corinna Weaver CROSBY & ASSOCIATES, INC.

  6346 Bayberry Blvd NE, Winter Haven, FL 33881
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  /2

  Est $289,593

  Not Listed For Sale

  536 Squires Grove Dr, Winter Haven, FL 33880

  • 4 Beds
  • 2 Baths
  • 1,872 Sq Ft
  • Built 2018

  536 Squires Grove Dr, Winter Haven, FL 33880

  Last Sold Summary

  • 63 Days On Market

  Last Listing Agent Andrea Friedmann KELLER WILLIAMS REALTY SMART 1
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  /39

  $44,000

  $21K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,056 Sq Ft

  369 Putter Cir, Winter Haven, FL 33881

  This 2-bedroom, 2-bathroom home offers a perfect place for relaxation plus lots of room for activities. Enjoy the convenience of an inside laundry and unwind in your private screened room at the back of the home. The central A/C was upgraded to "mini splits" in 2028 & 2019 in the living room, the Florida room and both of the bedrooms. The windows were replaced in 2018. There is a

  

  Cindy Minnick

  Sun Resales, Inc.

  369 Putter Cir, Winter Haven, FL 33881
• 

  

  /11

  $2,500 Per Month

  • 4 Beds
  • 3 Baths
  • 1,579 Sq Ft
  • House for Rent

  110 Broward Dr, Winter Haven, FL 33884

  Beautiful Move-In Ready Home – 3 Bedrooms, 2 Bathrooms + Private Anex with Independent EntranceThis spacious and fully updated home is ready for immediate occupancy and allows sub-rentalThe main home features 4 bedrooms and 3 bathrooms, along with a separate anex with its own private entrance, perfect for extended family, guests, or additional workspace. The property has been fully

  

  Maria Carolina Lopez

  LOKATION

  110 Broward Dr, Winter Haven, FL 33884
• 

  /2

  $259,000

  Sold Mar 16, 2026

  3674 Queens Cove Blvd, Winter Haven, FL 33880

  • 4 Beds
  • 2 Baths
  • 1,750 Sq Ft
  • Built 2005

  Last Sold Summary

  • $148/SF
  • 51 Days On Market

  Current Estimated Value $266,413

  Last Listing Agent Vivian Ortiz OAK AVENUE REAL ESTATE LLC

  3674 Queens Cove Blvd, Winter Haven, FL 33880
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  /2

  Est $141,848

  Not Listed For Sale

  1740 Inman Dr NW, Winter Haven, FL 33881

  • 3 Beds
  • 1 Bath
  • 805 Sq Ft
  • Built 1961

  1740 Inman Dr NW, Winter Haven, FL 33881

  Last Sold Summary

  • 6 Days On Market

  Last Listing Agent Carrissa Henshaw RE/MAX COLLECTIVE
• 

  

  /22

  $69,000

  • 2 Beds
  • 2 Baths
  • 938 Sq Ft

  508 Century Dr, Winter Haven, FL 33881

  Rare gem, gorgeous 2 bedroom 2 bath, 1989 Homes of Merit, on beautiful golf course with a pond view. Renovated home with over 1400 sf, laminate flooring (2022) throughout, both bathrooms (2020), updated kitchen including granite counter tops (2018), screened patio (2021), windows surround the enclosed Fl room with mini split system to enjoy the golf course view and some of Florida's wildlife

  

  Cindy Minnick

  Sun Resales, Inc.

  508 Century Dr, Winter Haven, FL 33881
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  /35

  $2,375 Per Month

  • 4 Beds
  • 2 Baths
  • 1,791 Sq Ft
  • House for Rent

  322 Royal Palm Way, Winter Haven, FL 33881

  Built in 2022, this 4-bedroom, 2-bath home features wood-look tile throughout, a modern kitchen with quartz countertops and stainless steel appliances, 100% LED lighting, LED-lit tray ceilings, ceiling fans in every room, 2" blinds, energy-efficient doors and windows, a covered porch, and a 2-car garage. A separate office sits off its own hallway and can serve as a fourth bedroom. All appliances

  322 Royal Palm Way, Winter Haven, FL 33881
• 

  /2

  $286,000

  Sold Jul 31, 2026

  1715 Sandalwood Cir SW, Winter Haven, FL 33880

  • 3 Beds
  • 2 Baths
  • 1,556 Sq Ft
  • Built 1990

  Last Sold Summary

  • 4% Below List Price
  • $184/SF
  • 72 Days On Market

  Current Estimated Value $283,060

  Last Listing Agent Teri Markley CENTURY 21 WATSON & MYERS REALTY

  1715 Sandalwood Cir SW, Winter Haven, FL 33880
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  /7

  Est $293,445

  Not Listed For Sale

  3711 Julius Estates Blvd, Winter Haven, FL 33881

  • 4 Beds
  • 2 Baths
  • 1,842 Sq Ft
  • Built 2014

  3711 Julius Estates Blvd, Winter Haven, FL 33881

  Last Sold Summary

  • 76 Days On Market

  Last Listing Agent Stephanie Florez CENTURY 21 WOLF'S CROSSING REALTY
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  /32

  $1,200,000

  • 3 Beds
  • 2 Baths
  • 2,129 Sq Ft

  4401 Chambliss Rd, Winter Haven, FL 33884

  Welcome to your slice of heaven in Winter Haven! Situated on just over 6.5 acres you will find this charming 3/2/2 Cassidy custom pool home surrounded by green meadows and mature oak trees. 4401 Chambliss Rd. offers space, freedom, and a lifestyle you simply won’t find inside typical neighborhoods. This expansive homestead provides room for horses, chickens, gardens, equipment, and future

  

  Cyleste Goodson

  FLORIDA REAL ESTATE COMPANY

  4401 Chambliss Rd, Winter Haven, FL 33884
• 

  /2

  $1,450 Per Month

  • 3 Beds
  • 2.5 Baths
  • 1,356 Sq Ft
  • Condo for Rent

  5850 Cypress Gardens Blvd Unit 806, Winter Haven, FL 33884

  MAINTENANCE-FREE LIVING JUST STEPS FROM LEGOLAND! This 3-bedroom, 2.5-bathroom townhome-style condo in Royal Crescent Condominiums offers comfortable living in a convenient Southeast Winter Haven location. The two-story floor plan features all bedrooms upstairs, including a spacious primary suite with a walk-in closet, private bathroom, and balcony overlooking the community pool. The second and

  

  Amy Reynolds

  LOCKHART & ASSOCIATES INC

  5850 Cypress Gardens Blvd Unit 806, Winter Haven, FL 33884
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  /12

  $265,000

  Sold Sep 23, 2025

  4981 Kaia Ave, Winter Haven, FL 33884

  • 3 Beds
  • 2 Baths
  • 1,269 Sq Ft
  • Built 2025

  Move in Ready Sold Summary

  • $209/SF
  • 145 Days On Market

  Current Estimated Value $237,410

  Meritage Homes VillaMar - Classic Series

  4981 Kaia Ave, Winter Haven, FL 33884
• 

  

  /23

  Est $307,475

  Not Listed For Sale

  213 Majestic Gardens Ln, Winter Haven, FL 33880

  • 4 Beds
  • 2 Baths
  • 1,840 Sq Ft
  • Built 2017

  213 Majestic Gardens Ln, Winter Haven, FL 33880

  Last Sold Summary

  • 55 Days On Market

  Last Listing Agent Nikki Scudiero ATRIUM REALTY, LLC
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  /49

  $189,900

  $29K PRICE DROP Pending

  • 2 Beds
  • 2 Baths
  • 1,257 Sq Ft

  1502 Buckeye Rd NE Unit 4, Winter Haven, FL 33881

  Virtually Staged. A rare opportunity to own one of only six cluster homes positioned along the peaceful shoreline of Lake Buckeye! A charming open courtyard entry welcomes you to the front door, creating a private and inviting approach that sets this home apart. Inside, the living room immediately draws your eye outdoors, featuring double French doors that open to an enclosed lanai and extended

  

  CarLee Marchetti

  STAR REALTY OF WINTER HAVEN

  1502 Buckeye Rd NE Unit 4, Winter Haven, FL 33881
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  /31

  $1,800

  Total Monthly Price

  • 4 Beds
  • 2 Baths
  • 1,368 Sq Ft
  • House for Rent

  3960 Avenue U NW, Winter Haven, FL 33881

  Don't miss out on this 4 bedroom home, at an amazing price. This home has been freshly painted and has ceramic tile throughout. The French doors lead to a paver patio that provides access to a huge backyard. The uncovered gazebo/patio area is perfect for those fire pit evenings. Your front covered patio gives you a Waterview of Lake Blue.

  3960 Avenue U NW, Winter Haven, FL 33881
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  /2

  $235,000

  Sold Jul 17, 2026

  852 Cinnamon Dr, Winter Haven, FL 33880

  • 3 Beds
  • 2 Baths
  • 1,072 Sq Ft
  • Built 1981

  Last Sold Summary

  • $219/SF
  • 3 Days On Market

  Current Estimated Value $234,826

  Last Listing Agent Gregory Buckley LOKATION

  852 Cinnamon Dr, Winter Haven, FL 33880
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  /2

  Not Listed For Sale

  3008 Thornhill Rd, Winter Haven, FL 33880

  • 4 Beds
  • 2 Baths
  • 1,440 Sq Ft
  • Built 1984

  3008 Thornhill Rd, Winter Haven, FL 33880

  Last Sold Summary

  • 19 Days On Market

  Last Listing Agent Dawn Justice CHARLES RUTENBERG REALTY INC
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  /32

  $399,999

  $20K PRICE DROP

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

  205 Tifton St, Winter Haven, FL 33880

  Honey, stop the car! This home truly has it all. Featuring 5 bedrooms, 4 full baths, a spacious loft, and a 3-car garage, this property offers room for everyone.Your 68,132 sq. ft. homesite (1.56 acres) is a little piece of heaven—flat, open space with no rear neighbor, perfect for privacy and endless possibilities.Inside, you’ll find an entertainer’s paradise: a double oven, a kitchen

  

  Paul Shearn

  FUTURE HOME REALTY INC

  205 Tifton St, Winter Haven, FL 33880
• 

  

  /20

  $1,700 Per Month

  • 2 Beds
  • 1 Bath
  • 1,032 Sq Ft
  • House for Rent

  1313 4th St NE, Winter Haven, FL 33881

  Welcome home to this charming 2-bedroom, 1-bathroom rental located in the desirable Chain of Lakes area of Winter Haven! This beautifully renovated home offers a comfortable and inviting space with plenty of room to make it your own. Featuring a newer roof installed in Fall 2023, the home also includes a versatile bonus room that can be used as a home office, guest space, playroom, or additional

  

  Rafael Narvaez

  EXP REALTY LLC

  1313 4th St NE, Winter Haven, FL 33881
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  /2

  $245,000

  Sold Jan 13, 2026

  4710 Osprey Way, Winter Haven, FL 33881

  • 4 Beds
  • 2 Baths
  • 1,992 Sq Ft
  • Built 2019

  Last Sold Summary

  • 18% Below List Price
  • $123/SF
  • 150 Days On Market

  Current Estimated Value $262,791

  Last Listing Agent Stuart Hurry NU HOME FINDERS, INC

  4710 Osprey Way, Winter Haven, FL 33881
• 

  /2

  Est $286,373

  Not Listed For Sale

  1429 Wallace Manor Pass, Winter Haven, FL 33880

  • 3 Beds
  • 2 Baths
  • 1,750 Sq Ft
  • Built 2013

  1429 Wallace Manor Pass, Winter Haven, FL 33880

  Last Sold Summary

  • 55 Days On Market

  Last Listing Agent Kali Sikes PREMIER REALTY NETWORK, INC
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  /63

  $54,990

  $3K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,380 Sq Ft

  104 Rigi Slope Dr, Winter Haven, FL 33881

  Discover retirement retreat in Swiss Village, a 55+ community nestled on Lake Henry. This maintained Palm Harbor manufactured home offers comfortable living with 2 bedrooms and 2 bathrooms, plus bonus spaces that make it truly special. Step inside to find updated polywood flooring throughout, replacing carpet in 2022 when subfloors were also reinforced with 3/4" plywood. Enjoy an enclosed front

  

  Chrissy Walter

  Sunset Home Sales

  104 Rigi Slope Dr, Winter Haven, FL 33881
• 

  

  /35

  $2,400 Per Month

  • 4 Beds
  • 2 Baths
  • 1,791 Sq Ft
  • House for Rent

  330 Royal Palm Way, Winter Haven, FL 33881

  Built in 2022, this 4-bedroom, 2-bath home features wood-look tile throughout, a modern kitchen with quartz countertops and stainless steel appliances, 100% LED lighting, LED-lit tray ceilings, ceiling fans in every room, 2" blinds, energy-efficient doors and windows, a covered porch, and a 2-car garage. A separate office sits off its own hallway and can serve as a fourth bedroom. All appliances

  330 Royal Palm Way, Winter Haven, FL 33881
• 

  /2

  $369,999

  Sold Oct 20, 2025

  5465 San Pietro Dr, Winter Haven, FL 33884

  • 4 Beds
  • 3 Baths
  • 2,292 Sq Ft
  • Built 2025

  Move in Ready Sold Summary

  • $161/SF
  • 10 Days On Market

  Current Estimated Value $346,763

  Casa Fresca Homes Villa Mar

  5465 San Pietro Dr, Winter Haven, FL 33884
• 

  

  /23

  Est $319,115

  Not Listed For Sale

  2972 Whispering Trails Dr, Winter Haven, FL 33884

  • 4 Beds
  • 2.5 Baths
  • 2,770 Sq Ft
  • Built 2013

  2972 Whispering Trails Dr, Winter Haven, FL 33884

  Last Sold Summary

  • 159 Days On Market

  Last Listing Agent ALLISON JOHNSTON THE SIMON SIMAAN GROUP
• 

  

  /56

  $44,990

  • 2 Beds
  • 2 Baths

  293 Alpine Dr, Winter Haven, FL 33881

  Discover your retreat in the heart of Central Florida! This **2-bedroom, 2-bathroom** furnished manufactured home is nestled within **Swiss Village**, an active **55+ retirement community** on beautiful **Lake Henry**. Move in with ease - this home comes furnished minus just a few personal items, so you can start enjoying the Florida lifestyle right away. Recent upgrades bring peace of mind,

  

  Chrissy Walter

  Sunset Home Sales

  293 Alpine Dr, Winter Haven, FL 33881
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  /14

  Starting at $1,000 Per Month

  • Studio - 2 Beds

  130 Avenue C SE, Winter Haven, FL 33880

  Central Haven Apartments

  130 Avenue C SE, Winter Haven, FL 33880
• 

  /2

  $335,000

  Sold Jul 24, 2026

  3600 Julius Estates Blvd, Winter Haven, FL 33881

  • 4 Beds
  • 2.5 Baths
  • 2,526 Sq Ft
  • Built 2014

  Last Sold Summary

  • 4% Below List Price
  • $133/SF
  • 299 Days On Market

  Current Estimated Value $333,668

  Last Listing Agent Gladys Falcon LUXURY REAL ESTATE GROUP LLC

  3600 Julius Estates Blvd, Winter Haven, FL 33881
• 

  /2

  Est $280,641

  Not Listed For Sale

  1109 Normandy Heights Cir, Winter Haven, FL 33880

  • 3 Beds
  • 2 Baths
  • 1,582 Sq Ft
  • Built 2013

  1109 Normandy Heights Cir, Winter Haven, FL 33880

  Last Sold Summary

  • 27 Days On Market

  Last Listing Agent Manny Quiros RE/MAX HERITAGE PROFESSIONALS
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  /37

  $288,500

  $27K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,770 Sq Ft

  1085 Brenton Manor Dr, Winter Haven, FL 33881

  Charming and inviting, this 3-bed, 2-bath home sits in a lovely Winter Haven community with a very low HOA. Built in 2015, it offers a modern design, a comfortable one-level layout, a 2-car garage, and all appliances included. Tucked into the vibrant Chain of Lakes region, you’re surrounded by peaceful views, leafy lakes, and plenty of outdoor fun from boat cruises to paddle boarding. And when

  

  Clarisa Moody

  MARZUCCO REAL ESTATE

  1085 Brenton Manor Dr, Winter Haven, FL 33881
• 

  

  /35

  $2,425 Per Month

  • 4 Beds
  • 2 Baths
  • 1,791 Sq Ft
  • House for Rent

  326 Royal Palm Way, Winter Haven, FL 33881

  Built in 2022, this 4-bedroom, 2-bath home features wood-look tile throughout, a modern kitchen with quartz countertops and stainless steel appliances, 100% LED lighting, LED-lit tray ceilings, ceiling fans in every room, 2" blinds, energy-efficient doors and windows, a covered porch, and a 2-car garage. A separate office sits off its own hallway and can serve as a fourth bedroom. All appliances

  326 Royal Palm Way, Winter Haven, FL 33881
• 

  /2

  $124,500

  Sold Apr 08, 2026

  4204 Cedarwood Dr, Winter Haven, FL 33880

  • 2 Beds
  • 2 Baths
  • 1,496 Sq Ft
  • Built 1983

  Last Sold Summary

  • 3% Below List Price
  • $83/SF
  • 9 Days On Market

  Last Listing Agent Kathy Devor COLDWELL BANKER REALTY

  4204 Cedarwood Dr, Winter Haven, FL 33880
• 

  

  /40

  Est $298,774

  Not Listed For Sale

  5816 Marsh Landing Dr, Winter Haven, FL 33881

  • 3 Beds
  • 2 Baths
  • 1,722 Sq Ft
  • Built 2017

  5816 Marsh Landing Dr, Winter Haven, FL 33881

  Last Sold Summary

  • 4 Days On Market

  Last Listing Agent Nathan Meyer EXP REALTY LLC
• 

  

  /45

  $425,000

  $40K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,663 Sq Ft

  148 Lake Otis Rd, Winter Haven, FL 33884

  HUGE PRICE REDUCTION! SELLER VERY MOTIVATED! Spacious 4-Bedroom, 3-Bath Pool Home in the admired Lakewood Community. Nestled on an oversized lot with mature trees, this remodeled tri-level home offers a perfect blend of modern luxury and comfort. With a spacious layout, a private pool, and an abundance of natural light, this home is designed for both relaxation and entertaining. As you enter,

  

  Michelle Armbruster

  LOCKHART & ASSOCIATES INC

  148 Lake Otis Rd, Winter Haven, FL 33884
• 

  

  /23

  Starting at $1,026 Per Month

  • 2 - 3 Beds

  4225 Vista Del Lago Dr, Winter Haven, FL 33881

  You've found your slice of paradise at Villas at Lake Smart in sunny Winter Haven, FL! Our spacious and affordable two and three-bedroom apartment homes offer the perfect sanctuary for you to unwind after a long day. Ensuring you don't have to go far for fun and fitness, our community features a volleyball court, playground, fitness center, clubhouse, pool, and more! Looking for some

  Villas at Lake Smart Apartments

  

  4225 Vista Del Lago Dr, Winter Haven, FL 33881
• 

  /2

  $144,500

  Sold Jan 23, 2026

  1550 11th St NE Unit B6, Winter Haven, FL 33881

  • 2 Beds
  • 2 Baths
  • 1,148 Sq Ft
  • Built 1974

  Last Sold Summary

  • 4% Below List Price
  • $126/SF
  • 7 Days On Market

  Current Estimated Value $141,152

  Last Listing Agent Laura Barnes CHAIN OF LAKES REALTY INC

  1550 11th St NE Unit B6, Winter Haven, FL 33881
• 

  

  /22

  Not Listed For Sale

  6776 Brentwood Dr NE, Winter Haven, FL 33881

  • 2 Beds
  • 2 Baths
  • 1,040 Sq Ft
  • Built 1984

  6776 Brentwood Dr NE, Winter Haven, FL 33881

  Last Sold Summary

  • 33 Days On Market

  Last Listing Agent Judy Morgan FREEDOM REALTY

Showing Results 121 - 160, Page 4 of 18