Winter Haven, FL Homes

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  /30

  $77,000

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

  1011 Eagle Dr, Winter Haven, FL 33881

  This stunning 2 bedroom, 2 bath home has been thoughtfully renovated throughout, featuring newer windows and stylish vinyl plank flooring. The updated kitchen offers plenty of cabinetry and a cozy eat-in area-perfect for morning coffee or casual meals. Both bathrooms have been tastefully updated for a clean, modern feel. You'll love the spacious Florida Room across the front of the home, finished

  

  Cindy Minnick

  Sun Resales, Inc.

  (863) 869-2719

  1011 Eagle Dr, Winter Haven, FL 33881
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  /8

  $1,295 per month

  • 3 Beds
  • 1 Bath
  • 950 Sq Ft
  • House for Rent

  400 Avenue D SE Unit 3, Winter Haven, FL 33880

  Rent with confidence from a licensed leasing agent. Our application process is quick and straightforward — reach out through this website or give us a call to schedule a tour (when the property is available) and apply. Welcome to this charming 3-bed, 2-bath home! The spacious layout offers plenty of room for comfortable everyday living. As you approach the home, you'll find a lovely outdoor area

  Erich Spivey ALABAMA LLC

  400 Avenue D SE Unit 3, Winter Haven, FL 33880
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  $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 $259,216

  Last Listing Agent Vivian Ortiz OAK AVENUE REAL ESTATE LLC

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

  Est $511,100 Not Listed For Sale

  1621 Hummingbird Ln, Winter Haven, FL 33884

  • 5 Beds
  • 3 Baths
  • 2,457 Sq Ft
  • Built 2024

  1621 Hummingbird Ln, Winter Haven, FL 33884

  Last Sold Summary

  • 9% Above List Price
  • $192/SF
  • 53 Days On Market

  Last Sold Price $470,995

  Last Listing Agent Dale Human CASA FRESCA REALTY
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  /29

  $140,000

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

  104 Mayfair Place SW, Winter Haven, FL 33880

  Enjoy this clean 2 bedroom, 2 bath villa in the community of Mayfair Place. Step into a spacious great room with soaring ceilings and all ceramic tile floors throughout, offering both style and ease of maintenance. The open kitchen includes plenty of counterspace, gas range/stove, and breakfast bar. The primary suite features sliding glass doors leading to a peaceful back patio, the perfect spot

  

  CarLee Marchetti

  STAR REALTY OF WINTER HAVEN

  (863) 343-3020

  104 Mayfair Place SW, Winter Haven, FL 33880
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  /11

  $1,395 - $2,050 per month

  Magnolia at Lake Hamilton

  1 - 3 Beds

  2850 W Lake Hamilton Dr, Winter Haven, FL 33881

  Welcome Home to Magnolia at Lake Hamilton!

  2850 W Lake Hamilton Dr, Winter Haven, FL 33881
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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 $239,439

  Meritage Homes VillaMar - Classic Series

  4981 Kaia Ave, Winter Haven, FL 33884
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  /2

  Est $304,064 Not Listed For Sale

  1954 Sarah Ln, Winter Haven, FL 33884

  • 4 Beds
  • 2 Baths
  • 1,824 Sq Ft
  • Built 2025

  1954 Sarah Ln, Winter Haven, FL 33884

  Last Sold Summary

  • 7% Above List Price
  • $156/SF
  • 66 Days On Market

  Last Sold Price $284,999

  Last Listing Agent Ben Goldstein LENNAR REALTY
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  /28

  $185,000 Pending

  • 2 Beds
  • 1 Bath
  • 576 Sq Ft

  1607 2nd St SE, Winter Haven, FL 33880

  PRIME LOCATION!! Prime Investment Opportunity with Commercial Zoning! Located in the Historic Pughsville neighborhood of Winter Haven. This property offers incredible versatility. Currently a cozy 2-bedroom, 1-bath residential wood framed home, the lot is zoned commercial, opening the door for various business uses. The property features a spacious, fenced-in yard with the added benefit of No HOA

  

  Twanna Dewdney

  LA ROSA REALTY PRESTIGE

  (863) 532-7906

  1607 2nd St SE, Winter Haven, FL 33880
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  /60

  $2,700 per month

  • 4 Beds
  • 3 Baths
  • 2,884 Sq Ft
  • House for Rent

  570 Sanctuary Blvd, Winter Haven, FL 33881

  Bring the entire family at this majestic home artfully laid out in an airy, open floor plan with plenty of rooms & abundant spaces. Resident(s) are responsible for utilities as well as renter's insurance, & lawn maintenance. All occupants 18 yrs. old above must complete the application. Applicants are encourage to disclose employment & credit information prior to scheduling a showing. Application

  Lienyvette Grimaldo MAZELG REALTY

  570 Sanctuary Blvd, 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 $261,897

  Last Listing Agent Stuart Hurry NU HOME FINDERS, INC

  4710 Osprey Way, Winter Haven, FL 33881
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  /2

  Est $251,914 Not Listed For Sale

  3868 Giorgio Dr, Winter Haven, FL 33884

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

  3868 Giorgio Dr, Winter Haven, FL 33884

  Last Sold Summary

  • 1% Above List Price
  • $197/SF
  • 36 Days On Market

  Last Sold Price $250,000

  Last Listing Agent Tatiana Souza FLORIDA CONNEXION PROPERTIES
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  /37

  $290,000

  • 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

  (863) 900-9378

  1085 Brenton Manor Dr, Winter Haven, FL 33881
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  /65

  $959 - $1,793 per month

  Carlton Arms Of Winter Haven

  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.

  7676 Carlton Arms Blvd, Winter Haven, FL 33884
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  /5

  $244,990 Sold Aug 29, 2025

  230 Turtle Bay Ave, Winter Haven, FL 33881

  • 3 Beds
  • 2 Baths
  • 1,604 Sq Ft
  • Built 2025

  Move in Ready Sold Summary

  • $153/SF
  • 11 Days On Market

  Highland Homes Harbor at Lake Henry - Townhomes

  230 Turtle Bay Ave, Winter Haven, FL 33881
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  /2

  Est $269,128 Not Listed For Sale

  1379 Benevento Dr, Winter Haven, FL 33884

  • 3 Beds
  • 2 Baths
  • 1,491 Sq Ft
  • Built 2025

  1379 Benevento Dr, Winter Haven, FL 33884

  Last Sold Summary

  • $180/SF
  • 45 Days On Market

  Last Sold Price $268,000

  Last Listing Agent Tatiana Souza FLORIDA CONNEXION PROPERTIES
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  /49

  $290,000

  • 3 Beds
  • 2 Baths

  542 Eagle Landing Blvd, Winter Haven, FL 33880

  Welcome to the Eagle Landing community in Winter Haven, FL. This well-maintained single-family home is move-in ready and waiting for its new owner(s). The open-floor concept creates a comfortable flow throughout the main living areas, while the split floor plan provides added privacy for the primary bedroom and bath with spacious walk-in closet.The kitchen features stainless steel appliances

  

  Carla Miro

  CENTURY 21 WATSON & MYERS REAL

  (863) 312-0574

  542 Eagle Landing Blvd, Winter Haven, FL 33880
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  /18

  $2,039 per month

  • 4 Beds
  • 3 Baths
  • 2,150 Sq Ft
  • House for Rent

  Unlisted Address

  Take a look at this beautiful home, Clean and Move-In Ready, featuring 4 bedrooms, _3 bathrooms, 2 car garage and approximately 2,150 heated square feet. Enjoy the freedom of a virtually maintenance free lifestyle while residing in a great community. Smart Home Tech - $21.95/mo; Washer/Dryer - $35/mo; High Speed Cable/Internet (if applicable by 3rd Party user) $55/mo; Renters insurance reqrd,

  Cathy Behe TAH FLORIDA LLC

  Unlisted Address
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  /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
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  /2

  Est $326,980 Not Listed For Sale

  1620 Leamington Ln, Winter Haven, FL 33884

  • 4 Beds
  • 2.5 Baths
  • 2,168 Sq Ft
  • Built 2025

  1620 Leamington Ln, Winter Haven, FL 33884

  Last Sold Summary

  • 2% Above List Price
  • $148/SF
  • 53 Days On Market

  Last Sold Price $319,795

  Last Listing Agent Tatiana Souza FLORIDA CONNEXION PROPERTIES
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  /43

  $369,999

  • 4 Beds
  • 2 Baths
  • 1,907 Sq Ft

  6003 Live Oak Dr, Winter Haven, FL 33880

  Honey, stop the car! This is the one you’ve been waiting for.This beautifully maintained 4-bedroom, 2-bathroom home sits on a spacious 0.45-acre fenced lot, offering the space, privacy, and outdoor lifestyle today’s buyers are searching for. Enjoy the soon-to-be easy access to Avalon and Disney via Sawgrass Rd extension.Step inside and you’re welcomed by a spacious foyer that flows into a

  

  Paul Shearn

  FUTURE HOME REALTY INC

  (863) 204-4704

  6003 Live Oak Dr, Winter Haven, FL 33880
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  /38

  $1,274 - $1,899 per month

  Dream Winter Haven

  1 - 2 Beds

  5004 Dream Dr, Winter Haven, FL 33880

  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 33880
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  /2

  $352,690 Sold Sep 10, 2025

  2803 San Marco Way, Winter Haven, FL 33884

  • 3 Beds
  • 2.5 Baths
  • 2,298 Sq Ft
  • Built 2025

  Move in Ready Sold Summary

  • $153/SF

  Current Estimated Value $354,715

  Maronda Homes VillaMar

  2803 San Marco Way, Winter Haven, FL 33884
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  /2

  Est $352,960 Not Listed For Sale

  452 Ituna Cir, Winter Haven, FL 33881

  • 3 Beds
  • 2 Baths
  • 1,646 Sq Ft
  • Built 2024

  452 Ituna Cir, Winter Haven, FL 33881

  Last Sold Summary

  • 11% Above List Price
  • $193/SF
  • 95 Days On Market

  Last Sold Price $317,900

  Last Listing Agent George Lindsey, III CAMBRIDGE REALTY OF CENTRAL FL
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  /16

  $115,000

  • 2 Beds
  • 1.5 Baths
  • 851 Sq Ft

  831 Orchid Springs Dr Unit 831, Winter Haven, FL 33884

  Whether you are looking for your first home or first rental property, this condominium is a must see! Ideally located off of Overlook Drive in Winter Haven, minutes form Legoland, downtown Winter Haven, and the Chain of Lakes. This unit features an updated kitchen with an upgraded stainless steel gas stove, stainless steel dish washer, and a one-year-old refrigerator. Additionally, there are

  

  Steven Perkins

  CLARK REALTY LLC

  (863) 434-8323

  831 Orchid Springs Dr Unit 831, Winter Haven, FL 33884
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  /7

  $2,100 per month

  • 3 Beds
  • 2 Baths
  • 1,418 Sq Ft
  • House for Rent

  1734 Carnostie Rd, Winter Haven, FL 33884

  Beautiful Comfortable home awaits your tenant and their family. This 3/2/2 has an open floor concept. The great room plan opens up to vaulted ceiling . The kitchen has is a comfy breakfast nook. The home also features a Gourmet Kitchen The beautiful master bedroom is a split plan. All bedrooms are comfortable sized. Carpet in all bedrooms and tiles in the wet area. This is a must see. Wont last

  Hillorie Knight CHARLES RUTENBERG REALTY INC

  1734 Carnostie Rd, Winter Haven, FL 33884
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  /2

  $55,000 Sold Jul 11, 2025

  4151 Sprucewood St, Winter Haven, FL 33880

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

  Last Sold Summary

  • 42% Below List Price
  • $64/SF
  • 107 Days On Market

  Last Listing Agent Brandy Duncan COLDWELL BANKER REALTY

  4151 Sprucewood St, Winter Haven, FL 33880
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  /2

  Not Listed For Sale

  444 Ituna Cir, Winter Haven, FL 33881

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

  444 Ituna Cir, Winter Haven, FL 33881

  Last Sold Summary

  • $168/SF
  • 103 Days On Market

  Last Sold Price $339,900

  Last Listing Agent George Lindsey, III CAMBRIDGE REALTY OF CENTRAL FL
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  /33

  $195,000

  • 3 Beds
  • 2 Baths
  • 1,410 Sq Ft

  936 Avenue T SE, Winter Haven, FL 33880

  AGENTS - PLEASE VIEW REALTOR REMARKS IN THE MLS. Welcome to this beautiful 3-bedroom, 2-bathroom block home perfectly positioned at the end of a quiet cul-de-sac in Winter Haven's sought-after Cypress Gardens neighborhood. With 1,400 square feet of interior living space and a layout designed for both comfort and connection, this home checks every box. Step inside and you're immediately greeted by

  

  Daniel Rodriguez

  NEW HEIGHTS REALTY GROUP

  (863) 285-3066

  936 Avenue T SE, Winter Haven, FL 33880
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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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  /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 $143,528

  Last Listing Agent Laura Barnes CHAIN OF LAKES REALTY INC

  1550 11th St NE Unit B6, Winter Haven, FL 33881
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  /2

  Est $298,374 Not Listed For Sale

  4117 Giorgio Dr, Winter Haven, FL 33884

  • 3 Beds
  • 2 Baths
  • 1,672 Sq Ft
  • Built 2024

  4117 Giorgio Dr, Winter Haven, FL 33884

  Last Sold Summary

  • $178/SF
  • 135 Days On Market

  Last Sold Price $296,990

  Last Listing Agent Paul King DR HORTON REALTY OF CENTRAL FLORIDA LLC
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  /31

  $55,500

  • 2 Beds
  • 2 Baths
  • 1,920 Sq Ft

  488 Putter Cir, Winter Haven, FL 33881

  Welcome to this delightful 2-bedroom, 2-bath home where comfort meets convenience. Recent updates include a new AC (2025) and roof (2024), giving you peace of mind for years to come. A circular driveway and golf cart make life easy, while a large shed offers plenty of storage. Inside, you'll love the bonus room with a wet bar, perfect for entertaining, along with the convenience of indoor laundry

  

  Cindy Minnick

  Sun Resales, Inc.

  (863) 349-7230

  488 Putter Cir, Winter Haven, FL 33881
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  /12

  $1,800 per month

  • 3 Beds
  • 1.5 Baths
  • 1,160 Sq Ft
  • House for Rent

  922 Martin Luther King Blvd NE, Winter Haven, FL 33881

  Move-in ready rental opportunity in a convenient Winter Haven location. This property offers comfortable living spaces, great natural light, and a functional layout ideal for families or professionals. Located near major roads, shopping, dining, and local amenities, providing both convenience and accessibility. Monthly rent is $1,800.Schedule your showing today—this opportunity won’t last.

  Leidy Marroquin Bello EXP REALTY LLC

  922 Martin Luther King Blvd NE, Winter Haven, FL 33881
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  /2

  $95,000 Sold Jul 01, 2025

  256 Lakeside Ranch Cir, Winter Haven, FL 33881

  • 2 Beds
  • 2 Baths
  • 1,104 Sq Ft
  • Built 1978

  Last Sold Summary

  • 21% Below List Price
  • $86/SF
  • 92 Days On Market

  Last Listing Agent Lynne Halleran COLDWELL BANKER REALTY

  256 Lakeside Ranch Cir, Winter Haven, FL 33881
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  /2

  Est $291,744 Not Listed For Sale

  2587 Sage Valley Way, Winter Haven, FL 33884

  • 3 Beds
  • 2 Baths
  • 1,504 Sq Ft
  • Built 2024

  2587 Sage Valley Way, Winter Haven, FL 33884

  Last Sold Summary

  • 2% Above List Price
  • $189/SF
  • 124 Days On Market

  Last Sold Price $284,990

  Last Listing Agent Paul King DR HORTON REALTY OF CENTRAL FLORIDA LLC
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  /59

  $387,500

  • 4 Beds
  • 2 Baths
  • 2,078 Sq Ft

  5828 Marsh Landing Dr, Winter Haven, FL 33881

  Welcome to refined Florida living in the serene, gated, 55+ community of Preserve at Lakeside Landings. This community designed with enjoying your Florida lifestyle, is home to 44 residences, 2 pools, a playground, and sidewalks to keep you active. HOA includes lawn maintenance which allows you to relax in your stunning new home! Thoughtfully designed with a triple-split floorplan, this residence

  

  Cyleste Goodson

  FLORIDA REAL ESTATE COMPANY

  (863) 312-0317

  5828 Marsh Landing Dr, Winter Haven, FL 33881
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  /15

  $1,032 - $1,585 per month

  Briarcrest at Winter Haven

  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

  200 Avenue K SE, Winter Haven, FL 33880
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  /2

  $250,000 Sold Jun 30, 2025

  216 Kingshill Ct SE, Winter Haven, FL 33884

  • 3 Beds
  • 2 Baths
  • 1,462 Sq Ft
  • Built 1990

  Last Sold Summary

  • $171/SF
  • 3 Days On Market

  Current Estimated Value $251,945

  Last Listing Agent Ce Ce Devereaux DALTON WADE INC

  216 Kingshill Ct SE, Winter Haven, FL 33884
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  /2

  Est $361,384 Not Listed For Sale

  2571 Sage Valley Way, Winter Haven, FL 33884

  • 5 Beds
  • 3 Baths
  • 2,447 Sq Ft
  • Built 2024

  2571 Sage Valley Way, Winter Haven, FL 33884

  Last Sold Summary

  • 1% Above List Price
  • $147/SF
  • 147 Days On Market

  Last Sold Price $358,490

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

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