Winter Haven, FL Homes

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  $384,990 New Construction

  • 4 Beds
  • 2 Baths
  • 2,267 Sq Ft

  Highbourne Plan at Willowbrook North, Winter Haven, FL 33881

  HIGHBOURNE: Beautiful 2 Level, 2 Car Garage Home with Open Concept Living and up to 5 Bedrooms! The Highbourne plan is available in Coastal, Farmhouse or Traditional exterior designs. The inviting front porch opens to a gracious foyer with spacious flex space that leads to the island kitchen that overlooks the cafe and family room. The primary suite boasts an en suite bathroom with shower,

  DRB Homes Builder

  0 Fl-544 St Unit 36849118, Winter Haven, FL 33881
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  $1,475 per month

  • 1 Bed
  • 1 Bath
  • 2,093 Sq Ft
  • House for Rent

  1313 Diego Terrace Unit In-Law Suite, Winter Haven, FL 33884

  One or more photo(s) has been virtually staged. For Lease: Private In-Law Suite in Winter Haven, FL – $1,500/Month Looking for a clean, private rental in Winter Haven? This 450 sq. ft. in-law suite offers comfortable living in a quiet, well-located neighborhood. Important: This is a separate in-law suite attached to the main home. The main house is owner-occupied. This listing is not for the full

  Andrea Jastemski DALTON WADE INC

  1313 Diego Terrace Unit In-Law Suite, Winter Haven, FL 33884
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  $376,990 Sold Aug 29, 2025

  2526 Sage Valley Way, Winter Haven, FL 33884

  • 4 Beds
  • 3 Baths
  • 2,372 Sq Ft
  • Built 2024

  Last Sold Summary

  • 7% Below List Price
  • $159/SF
  • 275 Days On Market

  Current Estimated Value $377,969

  Last Listing Agent Paul King DR HORTON REALTY OF CENTRAL FLORIDA LLC

  2526 Sage Valley Way, Winter Haven, FL 33884
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  /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

  • $142/SF
  • 33 Days On Market

  Last Sold Price $147,500

  Last Listing Agent Judy Morgan FREEDOM REALTY
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  $230,000

  • 3 Beds
  • 1 Bath
  • 1,044 Sq Ft

  3426 Hickory St, Winter Haven, FL 33881

  One or more photo(s) has been virtually staged. NO HOA! LOW TAXES! ASSUMABLE FHA LOAN! Bring your boat, your work vehicle and your RV! This home is has plenty of yard to hold all your toys and you won't be bothered by an HOA! This move-in ready property features brand new flooring and fresh interior paint, offering a clean, modern feel throughout. This home is light and bright and ready for its

  Heather Carr, PA BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY

  3426 Hickory St, Winter Haven, FL 33881
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  $1,945 per month

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

  930 Deming Dr, Winter Haven, FL 33880

  Welcome to your dream home! Step inside this pet-friendly home featuring modern finishings and a layout designed with functionality in mind. Enjoy the storage space found in the kitchen and closets as well as the spacious living areas and natural light throughout. Enjoy outdoor living in your yard, perfect for gathering, relaxing, or gardening!Take advantage of the incredible location,

  930 Deming Dr, Winter Haven, FL 33880
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  $324,990 Sold Nov 27, 2025

  3251 Nightfall Rd, Winter Haven, FL 33881

  • 3 Beds
  • 2 Baths
  • 1,761 Sq Ft
  • Built 2025

  Last Sold Summary

  • $185/SF
  • 20 Days On Market

  Current Estimated Value $337,355

  Last Listing Agent Reed Williams ASHTON WOODS FLORIDA REALTY LLC

  3251 Nightfall Rd, Winter Haven, FL 33881
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  Est $308,810 Not Listed For Sale

  257 Oleander St, Winter Haven, FL 33881

  • 4 Beds
  • 2.5 Baths
  • 2,195 Sq Ft
  • Built 2018

  257 Oleander St, Winter Haven, FL 33881

  Last Sold Summary

  • 4% Below List Price
  • $147/SF
  • 78 Days On Market

  Last Sold Price $322,500

  Last Listing Agent Vilmari Caraballo RE/MAX
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  $1,015,000

  • Land
  • 4.83 Acres
  • $210,145 per Acre

  0 Recker Hwy Unit 25572387, Winter Haven, FL 33880

  Presenting a rare opportunity to acquire up to 4.83 acres of strategically positioned, BPC-2 zoned land along Recker Highway in the heart of Winter Havens rapidly growing industrial and logistics corridor. Offered as a full assemblage or as individual parcels, each lot provides flexible development potential for business park, flex-industrial, or light manufacturing uses under Polk Countys

  Saunders Estate Saunders Land

  0 Recker Hwy Unit 25572387, Winter Haven, FL 33880
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  /22

  $4,500 per month

  • 3 Beds
  • 3 Baths
  • 2,266 Sq Ft
  • House for Rent

  236 Ruby Lake Ln, Winter Haven, FL 33884

  One or more photo(s) has been virtually staged. Wake up every morning to the most breath taking views imaginable. Almost every room in the home overlooks the spectacular private Lake Ruby & Lake Bess. Upon entering the home you will find yourself captivated with the spacious and luxurious open floor plan and high degree of natural light that envelops you. Besides having the exquisite view, this

  Scott Kline KLINE REAL ESTATE SERVICES

  236 Ruby Lake Ln, Winter Haven, FL 33884
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  $82,500 Sold May 22, 2025

  517 Cipres Cir, Winter Haven, FL 33880

  • 3 Beds
  • 2 Baths
  • 1,101 Sq Ft
  • Built 1998

  Last Sold Summary

  • 10% Above List Price
  • $75/SF
  • 111 Days On Market

  Current Estimated Value $215,954

  Last Listing Agent David Small KELLER WILLIAMS REALTY SMART 1

  517 Cipres Cir, Winter Haven, FL 33880
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  Not Listed For Sale

  6482 Peppertree Path NE, Winter Haven, FL 33881

  • 2 Beds
  • 2 Baths
  • 1,300 Sq Ft
  • Built 1986

  6482 Peppertree Path NE, Winter Haven, FL 33881

  Last Sold Summary

  • $119/SF
  • 52 Days On Market

  Last Sold Price $155,000

  Last Listing Agent Jean Murphy CENTURY 21 MYERS REALTY
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  /5

  $925,000

  • Land
  • 4.16 Acres
  • $222,356 per Acre

  5637 Recker Hwy, Winter Haven, FL 33880

  Presenting a rare opportunity to acquire up to 4.16 acres of strategically positioned, BPC-2 zoned land along Recker Highway in the heart of Winter Havens rapidly growing industrial and logistics corridor. Offered as a full assemblage or as individual parcels, each lot provides flexible development potential for business park, flex-industrial, or light manufacturing uses under Polk Countys

  Saunders Estate Saunders Land

  5637 Recker Hwy, Winter Haven, FL 33880
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  $1,780 per month

  • 3 Beds
  • 2 Baths
  • 1,316 Sq Ft
  • House for Rent

  3320 Timberline Rd W, Winter Haven, FL 33880

  Beautiful, pet-friendly home coming soon! Apply now, Move-In is available on or after the listed date. Upon approval, $500 reservation deposit to reserve (applied to security deposit and/or refundable). Application fee: $50 per adult. Security Deposit: one month?s rent. Pet fees: $250 + $40/mo per pet. Some homes may include pool ($150/mo), septic ($15/mo), and/or HOA fees; other fees may apply.

  3320 Timberline Rd W, Winter Haven, FL 33880
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  $334,970 Sold Jul 10, 2025

  3158 Laurel Oak Ln, Winter Haven, FL 33884

  • 4 Beds
  • 2 Baths
  • 2,005 Sq Ft
  • Built 2025

  Last Sold Summary

  • 2% Below List Price
  • $167/SF
  • 1 Day On Market

  Current Estimated Value $339,551

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

  3158 Laurel Oak Ln, Winter Haven, FL 33884
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  Est $107,322 Not Listed For Sale

  2040 San Marcos Dr SE Unit 108, Winter Haven, FL 33880

  • 1 Bed
  • 1 Bath
  • 666 Sq Ft
  • Built 1985

  2040 San Marcos Dr SE Unit 108, Winter Haven, FL 33880

  Last Sold Summary

  • 19% Below List Price
  • $199/SF
  • 28 Days On Market

  Last Sold Price $132,500

  Last Listing Agent Spyro Lefkimiotis RE/MAX
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  $760,000

  • Land
  • 3.62 Acres
  • $209,945 per Acre

  0 Recker Hwy Unit 25572359, Winter Haven, FL 33880

  Presenting a rare opportunity to acquire up to 3.62 acres of strategically positioned, BPC-2 zoned land along Recker Highway in the heart of Winter Havens rapidly growing industrial and logistics corridor. Offered as a full assemblage or as individual parcels, each lot provides flexible development potential for business park, flex-industrial, or light manufacturing uses under Polk Countys

  Saunders Estate Saunders Land

  0 Recker Hwy Unit 25572359, Winter Haven, FL 33880
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  $1,750 per month

  • 2 Beds
  • 2 Baths
  • 1,490 Sq Ft
  • House for Rent

  14 Lamplight Ln, Winter Haven, FL 33884

  Welcome to 14 Lamplight Lane in beautiful Winter Haven — a delightful 2-bedroom, 2-bath home offering 1,490 square feet of comfortable living space plus a versatile bonus room that adds flexibility to fit your lifestyle. This inviting residence features a bright and open living area filled with natural light, creating a warm and welcoming atmosphere from the moment you step inside. With 1,490

  Leila Torres LA ROSA REALTY PRESTIGE

  14 Lamplight Ln, Winter Haven, FL 33884
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  $620,000 Sold Apr 14, 2026

  4310 Shadow Wood Trail, Winter Haven, FL 33880

  • 3 Beds
  • 4 Baths
  • 3,051 Sq Ft
  • Built 1985

  Last Sold Summary

  • 4% Below List Price
  • $203/SF
  • 48 Days On Market

  Current Estimated Value $630,229

  Last Listing Agent MaryAnn Bartlett NEX REALTY

  4310 Shadow Wood Trail, Winter Haven, FL 33880
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  Not Listed For Sale

  713 Byni Ridge, Winter Haven, FL 33880

  • 3 Beds
  • 2 Baths
  • 924 Sq Ft
  • Built 1990

  713 Byni Ridge, Winter Haven, FL 33880

  Last Sold Summary

  • $168/SF
  • 14 Days On Market

  Last Sold Price $154,900

  Last Listing Agent Ron Denney LAND SOUTH REALTY, LLC
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  $359,990 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,227 Sq Ft

  Naples Plan at Willowbrook North, Winter Haven, FL 33881

  NAPLES: Beautiful 2 Level, 2 Car Garage Home with Open Concept Living, Loft and up to 5 Bedrooms! The Naples plan is available in Coastal, Farmhouse or Traditional exterior designs. The inviting front porch opens to a gracious foyer with adjacent powder room. The well-appointed, island kitchen is open to the adjoining cafe and spacious family room. . The primary suite boasts an en suite bathroom

  DRB Homes Builder

  0 Fl-544 St Unit 36849116, Winter Haven, FL 33881
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  $2,340 per month

  • 4 Beds
  • 2.5 Baths
  • 2,400 Sq Ft
  • House for Rent

  2973 Whispering Trails Dr, Winter Haven, FL 33884

  We make Pre-Leasing easy! Apply now and, once you’re approved, take this home off the market by paying a Pre-Lease Hold Fee; ask your Leasing Professional for more information. Once the home is made ready, we'll notify you that it's available for touring and for you to accept or decline. If you decline the home, we'll be happy to help you find a different home or refund your Hold Fee. This home

  2973 Whispering Trails Dr, Winter Haven, FL 33884
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  $290,000 Sold Feb 18, 2026

  4525 Ashford Dr, Winter Haven, FL 33880

  • 3 Beds
  • 2 Baths
  • 2,434 Sq Ft
  • Built 1998

  Last Sold Summary

  • 9% Below List Price
  • $119/SF
  • 24 Days On Market

  Current Estimated Value $302,437

  Last Listing Agent Clarisa Moody MARZUCCO REAL ESTATE

  4525 Ashford Dr, Winter Haven, FL 33880
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  /28

  Est $130,580 Not Listed For Sale

  689 Lake Howard Dr NW Unit 103, Winter Haven, FL 33880

  • 3 Beds
  • 2 Baths
  • 1,232 Sq Ft
  • Built 1975

  689 Lake Howard Dr NW Unit 103, Winter Haven, FL 33880

  Last Sold Summary

  • 16% Below List Price
  • $126/SF
  • 23 Days On Market

  Last Sold Price $155,000

  Last Listing Agent Catherine Kluytenaar THE K TEAM REAL ESTATE SERVICES LLC
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  /25

  $434,900

  • 4 Beds
  • 2.5 Baths
  • 2,850 Sq Ft

  240 Santa Rosa Dr, Winter Haven, FL 33884

  *** Motivated seller! Beautiful 4/2.5 pool home with new roof (2024), septic (2024), A/C (2025) in gated Overlook Estates. Fresh price reduction, bring your offers! *** Experience the pinnacle of Florida living in this exceptional pool home, offering 2,850 sq ft of light-drenched space in the established Overlook Estates neighborhood, where privacy and prestige define the community. This is the

  Brian Surrency LIVE FLORIDA REALTY

  240 Santa Rosa Dr, Winter Haven, FL 33884
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  $2,100 per month

  • 4 Beds
  • 2.5 Baths
  • 1,880 Sq Ft
  • House for Rent

  6424 Domizio Dr, Winter Haven, FL 33884

  One or more photo(s) has been virtually staged. Welcome to this brand-new 2025-built home located in the highly desirable Villa Mar community in Winter Haven. Offering 4 bedrooms, 2 full bathrooms, and 1 half bath, this modern residence combines style, functionality, and comfort in one beautifully designed floor plan. Step inside to an open-concept layout filled with natural light, creating the

  Rodrigo Araujo Machado WRA BUSINESS & REAL ESTATE

  6424 Domizio Dr, Winter Haven, FL 33884
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  $307,500 Sold Jun 25, 2025

  4924 Saint James St, Winter Haven, FL 33881

  • 4 Beds
  • 2 Baths
  • 1,992 Sq Ft
  • Built 2018

  Last Sold Summary

  • 7% Below List Price
  • $154/SF
  • 88 Days On Market

  Current Estimated Value $314,739

  Last Listing Agent Mathias Jenniges IAD FLORIDA LLC

  4924 Saint James St, Winter Haven, FL 33881
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  Est $291,712 Not Listed For Sale

  5069 Brenton Manor Ave, Winter Haven, FL 33881

  • 3 Beds
  • 2 Baths
  • 1,895 Sq Ft
  • Built 2013

  5069 Brenton Manor Ave, Winter Haven, FL 33881

  Last Sold Summary

  • 1% Above List Price
  • $153/SF
  • 154 Days On Market

  Last Sold Price $290,000

  Last Listing Agent Christine Hubbert BHHS FLORIDA PROPERTIES GROUP
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  /34

  $317,000

  • 3 Beds
  • 2 Baths
  • 1,888 Sq Ft

  129 Morning Glory Cir, Winter Haven, FL 33884

  Welcome to this well-maintained 3-bedroom, 2-bath home with a 2-car garage, offering just under 1,900 square feet of comfortable living space. Built in 2002 and topped with a long-lasting, low-maintenance tile roof designed for lasting durability, this home is ideally positioned with no direct neighbors—backing up to peaceful green space for added privacy. This property has been thoughtfully

  Laurie Nock LPT REALTY, LLC

  129 Morning Glory Cir, Winter Haven, FL 33884
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  $2,295 per month

  • 4 Beds
  • 2 Baths
  • 1,730 Sq Ft
  • House for Rent

  331 Columbo St, Winter Haven, FL 33880

  We are currently making final preparations for this home to be available. We make Pre-Leasing easy! Apply now and, once you’re approved, take this home off the market by paying a Pre-Lease Hold Fee; ask your Leasing Professional for more information. Once the home is made ready, we'll notify you that it's available for touring and for you to accept or decline. If you decline the home, we'll be

  331 Columbo St, Winter Haven, FL 33880
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  $275,490 Sold Jan 28, 2026

  4157 Giorgio Dr, Winter Haven, FL 33884

  • 3 Beds
  • 2 Baths
  • 1,504 Sq Ft
  • Built 2026

  Move in Ready Sold Summary

  • $183/SF
  • 35 Days On Market

  Current Estimated Value $246,667

  D.R. Horton VillaMar

  4157 Giorgio Dr, Winter Haven, FL 33884
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  Est $513,544 Not Listed For Sale

  1877 Woodpointe Dr, Winter Haven, FL 33884

  • 3 Beds
  • 2 Baths
  • 2,024 Sq Ft
  • Built 2021

  1877 Woodpointe Dr, Winter Haven, FL 33884

  Last Sold Summary

  • 7% Below List Price
  • $274/SF
  • 3 Days On Market

  Last Sold Price $555,000

  Last Listing Agent Kelly Jones KELLER WILLIAMS REALTY SMART 1
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  $479,000

  • 4 Beds
  • 3 Baths
  • 2,569 Sq Ft

  305 Hernando Rd, Winter Haven, FL 33884

  Listing price reduced!!! Enjoy the quaint living in this deed restricted community! Step into this stunning home through a spacious, light-filled foyer and prepare to be impressed by the thoughtfully, well maintained designed layout and exceptional features throughout. This home offers oversized bedrooms and a versatile bonus room—perfect for a game room, home office, or even a private in-law

  Sherry Sapp COLDWELL BANKER REALTY

  305 Hernando Rd, Winter Haven, FL 33884
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  $1,795 per month

  • 3 Beds
  • 2 Baths
  • 1,269 Sq Ft
  • House for Rent

  3063 Laurel Oak Ln, Winter Haven, FL 33884

  2ND MONTH RENT FREE: Move-In Ready, Pet-Friendly, 2-Car Garage! Available for immediate occupancy! Step into this stunning 2023 Meritage Home in the heart of Winter Haven, Florida—a highly upgraded 3-bedroom, 2-bath single-story home designed to impress. This move-in ready home features neutral tones throughout, a chef-inspired kitchen with stainless steel appliances, quartz countertops, and a

  Katrina Anarumo RENT A FLORIDA HOME

  3063 Laurel Oak Ln, Winter Haven, FL 33884
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  $232,000 Sold Oct 21, 2025

  3118 Walnut St, Winter Haven, FL 33881

  • 3 Beds
  • 1 Bath
  • 1,013 Sq Ft
  • Built 1955

  Last Sold Summary

  • 1% Below List Price
  • $229/SF
  • 99 Days On Market

  Current Estimated Value $221,978

  Last Listing Agent Kathi Zerilli REDFIN CORPORATION

  3118 Walnut St, Winter Haven, FL 33881
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  Est $306,834 Not Listed For Sale

  3810 Fieldstone Cir, Winter Haven, FL 33881

  • 3 Beds
  • 2 Baths
  • 2,000 Sq Ft
  • Built 2016

  3810 Fieldstone Cir, Winter Haven, FL 33881

  Last Sold Summary

  • 1% Below List Price
  • $154/SF
  • 206 Days On Market

  Last Sold Price $309,000

  Last Listing Agent ALLISON JOHNSTON THE SIMON SIMAAN GROUP
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  $343,950 New Construction

  • 4 Beds
  • 3 Baths
  • 2,070 Sq Ft

  Slate Plan at Annabelle Estates, Lake Wales, FL 33859

  The thoughtfully designed Slate floor plan opens with two bedrooms flanking a full hall bath. Beyond the entry, you'll find an open layout with a dining nook, a great room with access to an inviting covered patio, and a kitchen with a center island, walk-in pantry and abundant cabinetry. The owner's suite is nearby, offering a generous walk-in closet and a private bath with optional dual sinks, a

  Richmond American Homes Builder

  4130 Old Bartow Lake Wales Rd Unit 36431511, Lake Wales, FL 33859
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  $2,130 per month

  • 4 Beds
  • 2 Baths
  • 1,946 Sq Ft
  • House for Rent

  264 Daisy Estates Dr, Winter Haven, FL 33884

  Please note, our homes are available on a first-come, first-serve basis and are not reserved until the lease is signed by all applicants and security deposits are collected.This home features Progress Smart Home - Progress Residential's smart home app, which allows you to control the home securely from any of your devices. Learn more at Want to tour on your own? Click the “Self

  264 Daisy Estates Dr, Winter Haven, FL 33884
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  $229,000 Sold Jul 15, 2025

  4174 Pirates Landing, Winter Haven, FL 33884

  • 2 Beds
  • 2 Baths
  • 1,332 Sq Ft
  • Built 1985

  Last Sold Summary

  • 5% Below List Price
  • $172/SF
  • 91 Days On Market

  Current Estimated Value $230,180

  Last Listing Agent Jill Lingenfelter CENTURY 21 MYERS REALTY

  4174 Pirates Landing, Winter Haven, FL 33884
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  Not Listed For Sale

  225 Sweet Cir, Winter Haven, FL 33884

  • 2 Beds
  • 2 Baths
  • 1,144 Sq Ft
  • Built 1986

  225 Sweet Cir, Winter Haven, FL 33884

  Last Sold Summary

  • $114/SF
  • 64 Days On Market

  Last Sold Price $130,000

  Last Listing Agent Hank Petty KELLER WILLIAMS REALTY SMART 1

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