48,523

Winter Haven, FL Homes

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  • /39

    $182,000 Pending

    • 2 Beds
    • 2 Baths
    • 1,017 Sq Ft

    307 Eagle Pond Dr, Winter Haven, FL 33884

    Under contract-accepting backup offers. PRICE ADJUSTMENT ALERT—the opportunity you've been waiting for! Welcome to easy, low-maintenance living in the 24/7 guard-gated Cypresswood Golf & Country Club. This charming condo offers peaceful POND VIEWS from the living room and both bedrooms, creating the perfect backdrop for relaxing mornings and quiet evenings.Inside, you'll love the bright, open

    Agent Photo

    Mabel Vassallo

    CENTURY 21 MYERS REALTY

    (863) 431-4399

    307 Eagle Pond Dr, Winter Haven, FL 33884
  • /18

    $2,000 per month

    • 3 Beds
    • 2 Baths
    • 1,483 Sq Ft
    • House for Rent

    4973 Kaia Ave, Winter Haven, FL 33884

    Welcome to this brand-new 2025-built home located in the highly desirable Villa Mar community in Winter Haven! Offering 3 bedrooms, 2 full bathrooms, 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 perfect space for both everyday living and entertaining. The

    Paola Martinez CENTURY 21 MCBRIDE REALTY GROUP

    4973 Kaia Ave, Winter Haven, FL 33884
  • /2

    $314,990 Sold May 27, 2025

    1606 Teagan Ln, Winter Haven, FL 33884

    • 4 Beds
    • 3 Baths
    • 2,174 Sq Ft
    • Built 2025

    Last Sold Summary

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

    Current Estimated Value $314,765

    Last Listing Agent Ben Goldstein LENNAR REALTY

    1606 Teagan Ln, Winter Haven, FL 33884
    • /2

      Est $317,843 Not Listed For Sale

      Unlisted Address

      • 4 Beds
      • 2 Baths
      • 1,820 Sq Ft
      • Built 2024
      Unlisted Address

      Last Sold Summary

      • 1% Below List Price
      • $177/SF
      • 163 Days On Market

      Last Sold Price $321,660

      Last Listing Agent Jose Nunez ADAMS HOMES REALTY

  • /31

    $69,000

    • 3 Beds
    • 2 Baths
    • 1,512 Sq Ft

    1006 Eagle Dr, Winter Haven, FL 33881

    Step into this stunning furnished 3-bedroom, 2-bath home with a den, offering over 1,500 sq. ft. of beautifully designed living space PLUS a huge enclosed Florida room with heat and AC-perfect for year-round enjoyment! You'll love the bright open living and dining area and the spacious kitchen featuring tons of counter and cabinet space along with a built-in desk for convenience. An interior

    Agent Photo

    Cindy Minnick

    Sun Resales, Inc.

    (863) 223-4692

    1006 Eagle Dr, Winter Haven, FL 33881
  • /12

    $1,189 - $1,598 per month

    Barrington Place At Winter Haven

    1 - 2 Beds

    1101 Cambridge Square, Winter Haven, FL 33880

    Barrington Place at Winter Haven is an intimate and charming community located in Winter Haven, FL. Our exclusive residences offer a serene retreat for residents seeking comfort and convenience. Discover the perfect balance of tranquility and accessibility, with proximity to Cypress Gardens Blvd., top-rated schools, healthcare facilities, and shopping destinations just moments away. Choose from

    1101 Cambridge Square, Winter Haven, FL 33880
  • /16

    $316,990 Sold Sep 04, 2025

    3466 Evening Star Dr, Winter Haven, FL 33881

    • 3 Beds
    • 2 Baths
    • 1,536 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • $206/SF
    • 26 Days On Market

    Current Estimated Value $324,949

    Starlight Homes Sunset Hills

    3466 Evening Star Dr, Winter Haven, FL 33881
    • /2

      Est $257,862 Not Listed For Sale

      1708 Teagan Ln, Winter Haven, FL 33884

      • 3 Beds
      • 2 Baths
      • 1,555 Sq Ft
      • Built 2024
      1708 Teagan Ln, Winter Haven, FL 33884

      Last Sold Summary

      • 5% Above List Price
      • $158/SF
      • 97 Days On Market

      Last Sold Price $245,000

      Last Listing Agent Ben Goldstein LENNAR REALTY

  • /71

    $440,000 Open Fri 5PM - 8PM

    • 3 Beds
    • 2 Baths
    • 2,363 Sq Ft

    5357 Hogan Ln, Winter Haven, FL 33884

    One or more photo(s) has been virtually staged. WATERFRONT CUSTOM St. John floor plan with CDD bond debt PAID IN FULL! Recent Upgrades: Kinetico whole-house water softener, refrigerator (2025), New roof (2024), AC, dishwasher, stove, additional screened room with pavers, and upgraded landscaping (2022). Experience Florida living at its finest in this beautifully upgraded 3-bedroom + den, 2-bath

    Agent Photo

    Emily Muscarella

    A+ REALTY LLC

    (863) 431-8559

    5357 Hogan Ln, Winter Haven, FL 33884
  • /14

    $2,000 per month

    • 3 Beds
    • 2 Baths
    • 1,483 Sq Ft
    • House for Rent

    3889 Giorgio Dr, Winter Haven, FL 33884

    Welcome to this brand-new 2025-built home located in the highly desirable Villa Mar community in Winter Haven! Offering 3 bedrooms, 2 full bathrooms, 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 perfect space for both everyday living and entertaining. The

    Paola Martinez CENTURY 21 MCBRIDE REALTY GROUP

    3889 Giorgio Dr, Winter Haven, FL 33884
  • /33

    $389,557 Sold Nov 14, 2025

    276 Meredith Blvd, Winter Haven, FL 33881

    • 4 Beds
    • 3 Baths
    • 2,110 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • $185/SF
    • 20 Days On Market

    Current Estimated Value $356,667

    Dream Finders Homes Willowbrook North

    276 Meredith Blvd, Winter Haven, FL 33881
    • /2

      Est $342,686 Not Listed For Sale

      3612 Julius Estates Blvd, Winter Haven, FL 33881

      • 4 Beds
      • 2.5 Baths
      • 2,759 Sq Ft
      • Built 2014
      3612 Julius Estates Blvd, Winter Haven, FL 33881

      Last Sold Summary

      • 2% Above List Price
      • $122/SF
      • 138 Days On Market

      Last Sold Price $336,000

      Last Listing Agent Robert Arnold SAND DOLLAR REALTY GROUP INC

  • /41

    $375,000

    • 4 Beds
    • 2 Baths
    • 2,336 Sq Ft

    262 Santa Rosa Dr, Winter Haven, FL 33884

    Spacious 2,336 SF pool home in the gated, tranquil Overlook Estates. This 4BR/2BA floorplan features a split-bedroom layout and generous living space including an eat-in kitchen, 17x18 vaulted family room, 10x16 dining room with bay window, and a large foyer. The master suite includes a dressing alcove and walk-in closet; an adjacent bedroom makes an ideal office or nursery. High-traffic areas

    Agent Photo

    Amy Reynolds

    LOCKHART & ASSOCIATES INC

    (863) 328-6637

    262 Santa Rosa Dr, Winter Haven, FL 33884
  • /50

    $1,236 - $1,806 per month

    Vista Lake Ned

    1 - 3 Beds

    4025 Lake Ned Village Cir, Winter Haven, FL 33884

    Flow through the good life at Vista Lake Ned Apartments. The park-like setting, eclectic amenities, and expansive interiors will make you fall in love with our apartments in Winter Haven. Even better, our Cypress Gardens location places you right off Highway 27 and close to Legoland! Add in the top-notch services that have earned us glowing reviews throughout the years, and you know you're in the

    4025 Lake Ned Village Cir, Winter Haven, FL 33884
  • /2

    $282,990 Sold Apr 24, 2025

    3440 Costello Cir, Winter Haven, FL 33884

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

    Last Sold Summary

    • 4% Below List Price
    • $170/SF
    • 52 Days On Market

    Current Estimated Value $299,824

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

    3440 Costello Cir, Winter Haven, FL 33884
    • /2

      Est $545,484 Not Listed For Sale

      306 Avenue C NE, Winter Haven, FL 33881

      • 3 Beds
      • 4 Baths
      • 3,060 Sq Ft
      • Built 1921
      306 Avenue C NE, Winter Haven, FL 33881

      Last Sold Summary

      • 2% Below List Price
      • $181/SF
      • 47 Days On Market

      Last Sold Price $555,000

      Last Listing Agent Barry Macchione RE/MAX

  • /15

    $250,000 Pending

    • 3 Beds
    • 2 Baths
    • 1,732 Sq Ft

    3180 Country Club Cir, Winter Haven, FL 33881

    Under contract-accepting backup offers. Short Sale. BANKRUPTCY SHORT SALE! Located In The Country Walk Community, This 2019 Built Home At 3180 Country Club Cir, Winter Haven, FL 33881 Features The Popular DR Horton Aria Floor Plan Offering 3 Bedrooms, 2 Bathrooms, & 1,672 Sq Ft Of Living Space. This Home Offers an Open Concept Layout With A Spacious Living Area, Split Bedroom Floor Plan, & a

    Agent Photo

    Jon McCall PA

    DALTON WADE INC

    (863) 250-1507

    3180 Country Club Cir, Winter Haven, FL 33881
  • /31

    $2,050 per month

    • 4 Beds
    • 2 Baths
    • 1,845 Sq Ft
    • House for Rent

    1993 Sarah St, Winter Haven, FL 33884

    Welcome to this spacious, modern 4-bedroom, 2-bathroom one-story home in the sought-after Peace Creek Reserve community! Perfectly positioned near Hwy 27, this prime location offers quick access to Legoland, Downtown Winter Haven & Lake Wales, shopping, dining, and the stunning Chain of Lakes—ideal for boating, fishing, and outdoor adventures. Step inside and spoil yourself with the upscale Bloom

    Anna Shi LPT REALTY, LLC

    1993 Sarah St, Winter Haven, FL 33884
  • /2

    $267,900 Sold Aug 17, 2025

    2021 Oliver Place, Winter Haven, FL 33881

    • 3 Beds
    • 2 Baths
    • 1,627 Sq Ft
    • Built 1967

    Last Sold Summary

    • 1% Below List Price
    • $165/SF
    • 21 Days On Market

    Current Estimated Value $265,563

    Last Listing Agent Glen Barron C BUDDY JOHNSON REALTY, LLC

    2021 Oliver Place, Winter Haven, FL 33881
    • /2

      Est $266,622 Not Listed For Sale

      1622 Tressel Ct, Winter Haven, FL 33881

      • 3 Beds
      • 2 Baths
      • 1,598 Sq Ft
      • Built 2019
      1622 Tressel Ct, Winter Haven, FL 33881

      Last Sold Summary

      • 2% Above List Price
      • $164/SF
      • 6 Days On Market

      Last Sold Price $262,000

      Last Listing Agent Melissa Witter KELLER WILLIAMS REALTY SMART 1

  • /24

    $250,000

    • 3 Beds
    • 1 Bath
    • 985 Sq Ft

    2122 Lake Blvd, Winter Haven, FL 33881

    This property is a RENT TO OWN OPPORTUNITY!!! Enjoy relaxed Florida living with beautiful lake views right from the front of this inviting home. Filled with natural light, the comfortable layout offers an easy, functional flow that makes everyday living and entertaining feel effortless. The thoughtfully designed interior keeps maintenance simple while maximizing comfort and usability. One of the

    Agent Photo

    Catherine Torres

    IAD FLORIDA LLC

    (863) 264-0380

    2122 Lake Blvd, Winter Haven, FL 33881
  • /26

    $1,160 - $1,575 per month

    Della Vita Apartments

    1 - 3 Beds

    4200 Mahogany Run, Winter Haven, FL 33884

    Della Vita Apartments offers the best in brand new interior finishes, abundant community amenity offerings and quick and easy access to some of the best shopping, entertainment and dining Winter Haven has to offer. We’ve recently started a multi-million dollar renovation that will enhance your everyday lifestyle. Our 1, 2 & 3 bedroom apartment homes include large bedrooms with walk-in closets,

    4200 Mahogany Run, Winter Haven, FL 33884
  • /2

    $313,162 Sold Oct 19, 2025

    1558 Jessica Blvd, Winter Haven, FL 33884

    • 5 Beds
    • 2.5 Baths
    • 2,326 Sq Ft
    • Built 2025

    Last Sold Summary

    • 6% Below List Price
    • $135/SF
    • 28 Days On Market

    Current Estimated Value $321,146

    Last Listing Agent Ben Goldstein LENNAR REALTY

    1558 Jessica Blvd, Winter Haven, FL 33884
    • /2

      Est $353,289 Not Listed For Sale

      2048 Marigold Aly, Winter Haven, FL 33884

      • 5 Beds
      • 3 Baths
      • 2,423 Sq Ft
      • Built 2024
      2048 Marigold Aly, Winter Haven, FL 33884

      Last Sold Summary

      • $146/SF
      • 257 Days On Market

      Last Sold Price $353,999

      Last Listing Agent Dale Human CASA FRESCA REALTY

  • /45

    $159,000

    • 2 Beds
    • 2 Baths
    • 2,208 Sq Ft

    194 Fairway Cir, Winter Haven, FL 33881

    This beautifully updated 2-bedroom, 2-bathroom unfurnished home offers modern comfort and timeless charm, nestled on a spacious private lot along the 14th hole of the golf course. Step inside to discover a fully renovated interior featuring luxury finishes throughout. A chef's dream kitchen, boasting a 5' double-door pantry, additional storage closet with shelving, tile backsplash, deep

    Agent Photo

    Cindy Minnick

    Sun Resales, Inc.

    (863) 336-6201

    194 Fairway Cir, Winter Haven, FL 33881
  • /13

    $1,275 per month

    • 2 Beds
    • 2 Baths
    • 2,732 Sq Ft
    • Apartment for Rent

    521 20th St SW Unit c, Winter Haven, FL 33880

    Winter Haven.. private home with rental unit. Only mins walk to Lake Howard and Lake Howard Nature Park.This unit is currently available for May 1 . Only minutes from major shopping and dining, and directly across from Lake Howard. This one bedroom unit is ground floor has large living space. Open floor plan with eat-in space in kitchen. Kitchen includes all appliances. Additional items include

    Scott Butts KIMBRIDGE REALTY, LLC

    521 20th St SW Unit c, Winter Haven, FL 33880
  • /2

    $395,000 Sold May 14, 2025

    410 Majestic Gardens Blvd, Winter Haven, FL 33880

    • 3 Beds
    • 2.5 Baths
    • 2,094 Sq Ft
    • Built 2006

    Last Sold Summary

    • $189/SF
    • 26 Days On Market

    Current Estimated Value $382,609

    Last Listing Agent Geraldine Anarumo FLORIDA REALTY MARKETPLACE

    410 Majestic Gardens Blvd, Winter Haven, FL 33880
    • /2

      Est $243,823 Not Listed For Sale

      899 5th St, Winter Haven, FL 33880

      • 3 Beds
      • 2 Baths
      • 1,710 Sq Ft
      • Built 1973
      899 5th St, Winter Haven, FL 33880

      Last Sold Summary

      • 2% Below List Price
      • $146/SF
      • 123 Days On Market

      Last Sold Price $250,000

      Last Listing Agent Erica Gonzalez LA ROSA REALTY PRESTIGE

  • /22

    $35,000

    • 2 Beds
    • 2 Baths

    625 Century Dr, Winter Haven, FL 33881

    This 940 sq ft home offers an open floor plan and a bright Florida room at the front of the house-perfect for relaxing or morning coffee. Recent improvements include new plumbing throughout (10/2023), a newer roof (2023), and an AC system installed around 2020. The home features convenient stackable inside laundry and a large shed for extra storage. A wonderful opportunity to make this home your

    Agent Photo

    Cindy Minnick

    Sun Resales, Inc.

    (863) 270-3168

    625 Century Dr, Winter Haven, FL 33881
  • /32

    $1,475 - $2,200 per month

    Lakeshore Club

    1 - 3 Beds

    1300 Lake Howard Dr SW, Winter Haven, FL 33880

    Welcome to luxury living in Winter Haven. Lakeshore Club is located on the Chain of Lakes between Lake Howard and Lake Mary minutes from downtown Winter Haven.

    1300 Lake Howard Dr SW, Winter Haven, FL 33880
  • /2

    $285,000 Sold Mar 16, 2026

    5316 Hogan Ln, Winter Haven, FL 33884

    • 2 Beds
    • 2 Baths
    • 1,339 Sq Ft
    • Built 2013

    Last Sold Summary

    • 1% Below List Price
    • $213/SF
    • 13 Days On Market

    Current Estimated Value $287,797

    Last Listing Agent Lori Raath LAKE ASHTON REALTY INC.

    5316 Hogan Ln, Winter Haven, FL 33884
    • /2

      Est $399,624 Not Listed For Sale

      2010 Canton Park Dr, Winter Haven, FL 33881

      • 5 Beds
      • 3.5 Baths
      • 2,692 Sq Ft
      • Built 2024
      2010 Canton Park Dr, Winter Haven, FL 33881

      Last Sold Summary

      • 5% Above List Price
      • $141/SF
      • 365 Days On Market

      Last Sold Price $379,990

      Last Listing Agent Michael Scott NEW HOME STAR FLORIDA LLC

  • /47

    $364,900 Open House 5/02

    • 4 Beds
    • 2 Baths
    • 2,113 Sq Ft

    115 Lake Mariam Way, Winter Haven, FL 33884

    Sellers say sell sell sell!! Welcome to 115 Lake Mariam Way in Winter Haven, FL, located in the highly desirable Lake Mariam Hills community. This updated 4-bedroom, 2-bath single-family home offers a functional layout ideal for comfortable everyday living, entertaining, or remote work. Homeowners have paid attention to detail! Residents enjoy private community boat ramp access to Lake Mariam,

    Agent Photo

    Lynn Arthur

    FAITH AND FAMILY REALTY LLC

    (863) 277-2033

    115 Lake Mariam Way, Winter Haven, FL 33884
  • /8

    $1,100 per month

    • 1 Bed
    • 1 Bath
    • 288 Sq Ft
    • House for Rent

    115 Avenue F SW Unit B, Winter Haven, FL 33880

    This brand-new studio apartment in Winter Haven offers efficient, low-maintenance living with an open layout and vinyl flooring throughout. The space features a bright main living area and a bathroom with a walk-in shower. With its fresh construction and easy-care design, the space maintains a straightforward, functional feel ideal for someone seeking a no-frills place to call home.

    Christin Davis PROPERTY MANAGEMENT OF POLK

    115 Avenue F SW Unit B, Winter Haven, FL 33880
  • /2

    $154,000 Sold Feb 26, 2026

    205 Winter Ridge Blvd Unit 3, Winter Haven, FL 33881

    • 3 Beds
    • 2 Baths
    • 1,073 Sq Ft
    • Built 1992

    Last Sold Summary

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

    Current Estimated Value $156,671

    Last Listing Agent Renee Butler BROKERS REALTY OF CENTRAL FLOR

    205 Winter Ridge Blvd Unit 3, Winter Haven, FL 33881
    • /2

      Est $277,147 Not Listed For Sale

      2523 Salzburg Loop, Winter Haven, FL 33884

      • 3 Beds
      • 2 Baths
      • 1,935 Sq Ft
      • Built 2011
      2523 Salzburg Loop, Winter Haven, FL 33884

      Last Sold Summary

      • 7% Above List Price
      • $133/SF
      • 30 Days On Market

      Last Sold Price $257,900

      Last Listing Agent Jesse Carriedo REALTYCITY INC

  • /35

    $280,000 Pending

    • 3 Beds
    • 2 Baths
    • 1,891 Sq Ft

    606 Turnberry Ct, Winter Haven, FL 33884

    Under contract-accepting backup offers. Looking for a gated community, 3 bedroom home with a bonus room? No need to look any further! Welcome to the highly sought-after Cypresswood Golf Community, where comfort, security, and convenience come together in this spacious 3-bedroom, 2-bath home with an added air conditioned Florida Room that offers a flexible bonus space perfect for anything your

    Agent Photo

    Daniel Rodriguez

    NEW HEIGHTS REALTY GROUP

    (863) 334-3846

    606 Turnberry Ct, Winter Haven, FL 33884
  • /7

    $1,350 - $1,450 per month

    Apartment for Rent

    2 Beds

    510 Avenue K NW, Winter Haven, FL 33881

    This property features a spacious 2-bed, 2-bath unit offering comfortable living space and thoughtful updates.This apartment includes modern conveniences such as central air conditioning, ceiling fans, and comfortable layouts designed for everyday living. There is also an on-site laundry facility exclusive to tenants for no extra cost. The building sits just minutes from downtown Winter

    510 Avenue K NW, Winter Haven, FL 33881
  • /16

    $279,304 Sold Oct 08, 2025

    2126 Chris Dr, Winter Haven, FL 33884

    • 3 Beds
    • 2 Baths
    • 1,487 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • $188/SF
    • 8 Days On Market

    Current Estimated Value $277,483

    Lennar Peace Creek Reserve - Estate Key Collection

    2126 Chris Dr, Winter Haven, FL 33884
    • /2

      Est $96,595 Not Listed For Sale

      4543 Emerald Palms Dr, Winter Haven, FL 33884

      4543 Emerald Palms Dr, Winter Haven, FL 33884

      Last Sold Summary

      • 3% Above List Price
      • 10 Days On Market

      Last Sold Price $93,500

      Last Listing Agent Deana Lainhart KELLER WILLIAMS REALTY SMART

Showing Results 121 - 160, Page 4 of 18

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