Winter Haven, FL Homes

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  $149,500

  • 2 Beds
  • 1.5 Baths
  • 1,332 Sq Ft

  5850 Cypress Gardens Blvd Unit 302, Winter Haven, FL 33884

  Welcome to this charming and updated, move-in ready 2-bedroom, 1.5-bath condo nestled right on Cypress Gardens Blvd in Winter Haven — just minutes from world-class shopping, dining, and the famous LEGOLAND Florida Resort! This well-maintained two-story unit has been tastefully updated throughout. Rich dark luxury vinyl plank flooring flows through the spacious living areas, giving the home a

  Vince Reina HAVEN REALTY & INVESTMENTS

  5850 Cypress Gardens Blvd Unit 302, Winter Haven, FL 33884
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  $2,300 per month

  • 4 Beds
  • 2 Baths
  • 1,696 Sq Ft
  • House for Rent

  263 Sunfish Dr, Winter Haven, FL 33881

  Now available for rent in the Lake Lucerne community—this well-maintained 4-bedroom, 2-bathroom home features a spacious and open floor plan.Newly fenced yard. The kitchen is equipped with granite countertops, stainless steel appliances, and a center island that overlooks the living and dining areas. The primary suite offers a walk-in closet and private bath. Tile flooring is featured in the main

  Leslie Soto HONEST EXPERTS REAL ESTATE LLC

  263 Sunfish Dr, Winter Haven, FL 33881
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  $55,000 Sold Jun 03, 2025

  613 Avenue O NE, Winter Haven, FL 33881

  • Land
  • 0.4 Acre
  • $137,500 per Acre

  Last Sold Summary

  • 4 Days On Market

  Current Estimated Value $53,786

  Last Listing Agent Michael Gay KELLER WILLIAMS REALTY SMART 1

  613 Avenue O NE, Winter Haven, FL 33881
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  /16

  Est $278,999 Not Listed For Sale

  4174 Roberta Dr, Winter Haven, FL 33881

  • 3 Beds
  • 2 Baths
  • 1,721 Sq Ft
  • Built 2017

  4174 Roberta Dr, Winter Haven, FL 33881

  Last Sold Summary

  • 2% Below List Price
  • $166/SF
  • 138 Days On Market

  Last Sold Price $286,000

  Last Listing Agent Vivian Ortiz OAK AVENUE REAL ESTATE LLC
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  $320,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 1,933 Sq Ft

  569 Reggie Rd, Winter Haven, FL 33884

  Under contract-accepting backup offers. Welcome to this beautifully designed two-story, 4 bedroom, 2.5 bathroom home, built in 2024 and located in the desirable Peace Creek Reserve community. This modern residence offers a functional layout, stylish finishes, and a peaceful setting with no rear neighbors. As you enter, you’re greeted by an inviting open floor plan that seamlessly connects the

  John Hubbert, Jr BHHS FLORIDA PROPERTIES GROUP

  569 Reggie Rd, Winter Haven, FL 33884
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  /19

  $1,575 total monthly price

  • 2 Beds
  • 1 Bath
  • 650 Sq Ft
  • Condo for Rent

  650 Ave B SW Unit 650 Avenue B SW, Winter Haven, FL 33880

  650 Ave B SW Unit 650 Avenue B SW, Winter Haven, FL 33880
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  $180,000 Sold Mar 24, 2026

  2833 Wingfoot Ct, Winter Haven, FL 33884

  • 2 Beds
  • 2 Baths
  • 1,471 Sq Ft
  • Built 1988

  Last Sold Summary

  • 5% Below List Price
  • $122/SF
  • 16 Days On Market

  Current Estimated Value $189,378

  Last Listing Agent CarLee Marchetti STAR REALTY OF WINTER HAVEN

  2833 Wingfoot Ct, Winter Haven, FL 33884
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  /25

  Est $344,074 Not Listed For Sale

  124 Waterside Cir, Winter Haven, FL 33880

  • 4 Beds
  • 2.5 Baths
  • 2,556 Sq Ft
  • Built 2017

  124 Waterside Cir, Winter Haven, FL 33880

  Last Sold Summary

  • 2% Below List Price
  • $137/SF
  • 129 Days On Market

  Last Sold Price $350,000

  Last Listing Agent ALLISON JOHNSTON THE SIMON SIMAAN GROUP
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  $315,000 Pending

  • 3 Beds
  • 2 Baths
  • 2,053 Sq Ft

  689 Vittorio Dr, Winter Haven, FL 33884

  Under contract-accepting backup offers. Welcome to the Serendipity floor plan — where comfort meets style!This stunning three-bedroom, den, two-bathroom home offers the perfect blend of modern design and everyday convenience. Step inside to find a bright, open-concept layout featuring high vaulted ceilings, a spacious great room, a beautifully appointed kitchen with a large island and walk-in

  Kelly Martinez CORCORAN CONNECT LLC

  689 Vittorio Dr, Winter Haven, FL 33884
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  /19

  $1,600 per month

  • 2 Beds
  • 2 Baths
  • 1,017 Sq Ft
  • Condo for Rent

  1704 Eagle Pond Dr Unit 1704, Winter Haven, FL 33884

  GROUND FLOOR Eagle Pond condominium in the highly desirable gated community of Cypresswood Golf and Country Club. This professionally-managed condominium has just been partially renovated to include luxury vinyl flooring and fresh paint throughout. Key features are interior laundry, walk-in closets, open concept living space, and so much more. The spacious master bedroom features an en suite

  Kayly Malinas JOHN WOOD REALTY, INC.

  1704 Eagle Pond Dr Unit 1704, Winter Haven, FL 33884
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  $249,000 Sold Jul 09, 2025

  1040 Cambridge Dr, Winter Haven, FL 33881

  • 3 Beds
  • 2 Baths
  • 1,727 Sq Ft
  • Built 2021

  Last Sold Summary

  • 4% Below List Price
  • $144/SF
  • 45 Days On Market

  Current Estimated Value $254,498

  Last Listing Agent Robert Jones OFFERPAD BROKERAGE FL, LLC

  1040 Cambridge Dr, Winter Haven, FL 33881
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  Est $302,396 Not Listed For Sale

  1152 Bowline St, Winter Haven, FL 33880

  • 3 Beds
  • 2 Baths
  • 1,622 Sq Ft
  • Built 2013

  1152 Bowline St, Winter Haven, FL 33880

  Last Sold Summary

  • 4% Below List Price
  • $194/SF
  • 0 Days On Market

  Last Sold Price $314,000

  Last Listing Agent Florina Sharrock GERMEROTH REALTY LLC
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  $320,690 New Construction

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

  2527 Sage Valley Way, Winter Haven, FL 33884

  The property is located at 2527 Sage Valley Way WINTER HAVEN FL 33884 priced at 320690, the square foot and stories are 1672, 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

  2527 Sage Valley Way, Winter Haven, FL 33884
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  $3,250 total monthly price

  • 2 Beds
  • 2.5 Baths
  • 1,600 Sq Ft
  • Condo for Rent

  154 2nd St SW Unit 2, Winter Haven, FL 33880

  Raingarden Apartments is a 9-unit collection of spacious luxury townhouse apartments located in downtown Winter Haven. Perfect for those looking to embrace a walkable, urban lifestyle where environmentally conscious living meets uncompromising, modern sophistication. All units have an enclosed 2-car garage and courtyard patio.

  154 2nd St SW Unit 2, Winter Haven, FL 33880
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  $265,000 Sold Mar 10, 2026

  3643 Julius Estates Blvd, Winter Haven, FL 33881

  • 3 Beds
  • 2 Baths
  • 1,750 Sq Ft
  • Built 2014

  Last Sold Summary

  • 4% Below List Price
  • $151/SF
  • 83 Days On Market

  Current Estimated Value $265,309

  Last Listing Agent Stacey Vazquez KELLER WILLIAMS REALTY AT THE LAKES

  3643 Julius Estates Blvd, Winter Haven, FL 33881
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  Est $231,448 Not Listed For Sale

  2327 Whispering Trails Place, Winter Haven, FL 33884

  • 3 Beds
  • 2 Baths
  • 1,148 Sq Ft
  • Built 2006

  2327 Whispering Trails Place, Winter Haven, FL 33884

  Last Sold Summary

  • 1% Below List Price
  • $205/SF
  • 21 Days On Market

  Last Sold Price $234,900

  Last Listing Agent Jeff Inman FHG REALTY, LLC
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  $329,000 Pending

  • 5 Beds
  • 3 Baths
  • 2,616 Sq Ft

  814 Sun Burst Rd, Winter Haven, FL 33880

  Under contract-accepting backup offers. This 2022-built 'Hayden' model in Squires Grove surpasses new construction, offering five generously sized bedrooms and a flexible open-concept floor plan. The property features a bright, south-facing backyard, ideal for enjoying Florida afternoons, a contemporary kitchen equipped with granite countertops, and the assurance of a low-risk Flood Zone X

  Dee Leon FLORIDA REALTY INVESTMENTS

  814 Sun Burst Rd, Winter Haven, FL 33880
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  $1,850 per month

  • 3 Beds
  • 2 Baths
  • 1,536 Sq Ft
  • Townhouse for Rent

  2727 Rutledge Ct, Winter Haven, FL 33884

  For Rent – 2727 Rutledge Court | $1,950/monthMove-in ready and available now! This end-unit townhome offers 2 bedrooms, 2 bathrooms, plus a flexible office/bonus room that can easily serve as a third bedroom, with 1,536 square feet of bright, low-maintenance Florida living.At $1,950 per month, rent includes internet, cable, lawn care, community pool access, a fishing dock, and a beautiful

  Veronica Bard LA ROSA REALTY PRESTIGE

  2727 Rutledge Ct, Winter Haven, FL 33884
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  $275,900 Sold Jan 19, 2026

  5117 Sylas Jax Ave, Winter Haven, FL 33884

  • 3 Beds
  • 2 Baths
  • 1,568 Sq Ft
  • Built 2026

  Move in Ready Sold Summary

  • $176/SF
  • 40 Days On Market

  Current Estimated Value $272,333

  Highland Homes VillaMar

  5117 Sylas Jax Ave, Winter Haven, FL 33884
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  Est $231,514 Not Listed For Sale

  1621 Vienna Square Dr, Winter Haven, FL 33884

  • 2 Beds
  • 2 Baths
  • 1,497 Sq Ft
  • Built 2015

  1621 Vienna Square Dr, Winter Haven, FL 33884

  Last Sold Summary

  • 7% Below List Price
  • $166/SF
  • 61 Days On Market

  Last Sold Price $249,000

  Last Listing Agent Wanda Dicks COLDWELL BANKER REALTY

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