48,920

Winter Haven, FL Homes

Section Image Section Image Section Image
  • /28

    $65,000

    • 2 Beds
    • 2 Baths

    1014 Eagle Dr, Winter Haven, FL 33881

    Tucked away at the end of the street, this charming 2-bedroom, 2-bath home offers privacy and peaceful living with no side or rear neighbors. The desirable split floor plan provides comfort and functionality, perfect for both everyday living and hosting guests. Enjoy a series of thoughtful updates, including stainless steel appliances (2022), A/C (2020), roof & leaf filter system (2023), new

    Agent Photo

    Cindy Minnick

    Sun Resales, Inc.

    (863) 900-9366

    1014 Eagle Dr, Winter Haven, FL 33881
  • /16

    $1,835 Per Month

    • 3 Beds
    • 2 Baths
    • 1,101 Sq Ft
    • House for Rent

    150 Madera Dr, 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.

    (863) 340-7308

    150 Madera Dr, 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 $286,029

    Last Listing Agent Lori Raath LAKE ASHTON REALTY INC.

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

      Est $339,206

      Not Listed For Sale

      3021 Royal Tern Dr, Winter Haven, FL 33881

      • 5 Beds
      • 3 Baths
      • 2,616 Sq Ft
      • Built 2018
      3021 Royal Tern Dr, Winter Haven, FL 33881

      Last Sold Summary

      • 192 Days On Market

  • /49

    $279,900

    $80K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,223 Sq Ft

    31 Lake Link Cir SE, Winter Haven, FL 33884

    Short Sale. Lender has provided preliminary net guidance based on a recent appraisal. Offers will be reviewed in accordance with lender and VA guidelines. Buyer is encouraged to submit highest and best offer. Final approval subject to lender review.This is the kind of home that just feels right the moment you pull in. Set on an oversized .29-acre lot with no rear neighbors and peaceful

    Agent Photo

    Katie Sweet

    WATSON REALTY CORP.

    (863) 265-5379

    31 Lake Link Cir SE, Winter Haven, FL 33884
  • /16

    $2,020 Per Month

    • 3 Beds
    • 2 Baths
    • 1,951 Sq Ft
    • House for Rent

    301 Majestic Gardens 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,

    (863) 451-8439

    301 Majestic Gardens Dr, 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 $154,004

    Last Listing Agent Renee Butler BROKERS REALTY OF CENTRAL FLOR

    205 Winter Ridge Blvd Unit 3, Winter Haven, FL 33881
    • /41

      Est $287,301

      Not Listed For Sale

      2185 Rose Blvd, Winter Haven, FL 33881

      • 4 Beds
      • 2 Baths
      • 1,851 Sq Ft
      • Built 2018
      2185 Rose Blvd, Winter Haven, FL 33881

      Last Sold Summary

      • 49 Days On Market

  • /45

    $302,500

    • 4 Beds
    • 2 Baths
    • 1,583 Sq Ft

    780 Overlook Grove Dr, Winter Haven, FL 33884

    Need 4 bedrooms, but don't need to break the budget? This is what you've been searching for here in the heart of Winter Haven! Situated perfectly W of Hwy 27 and out of the hustle and bustle of the city, this 4/2/2 home is ready for you! Close to houses of worship, schools, shopping, golf, and SO much more! Upon arrival, you note the quaint neighborhood, which quickly says "community." The home

    Agent Photo

    Cyleste Goodson

    FLORIDA REAL ESTATE COMPANY

    (863) 265-1231

    780 Overlook Grove Dr, Winter Haven, FL 33884
  • /15

    $1,750 Per Month

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

    3320 Timberline Rd W, 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,

    (863) 431-4711

    3320 Timberline Rd W, Winter Haven, FL 33880
  • /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 $281,997

    Lennar Peace Creek Reserve - Estate Key Collection

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

      Est $405,322

      Not Listed For Sale

      2973 Dayton Dr, Winter Haven, FL 33884

      • 3 Beds
      • 3 Baths
      • 2,659 Sq Ft
      • Built 2018
      2973 Dayton Dr, Winter Haven, FL 33884

      Last Sold Summary

      • 99 Days On Market

  • /62

    $449,900

    Under Contract
    • 4 Beds
    • 3 Baths
    • 2,354 Sq Ft

    308 Terranova Blvd, Winter Haven, FL 33884

    Welcome to your ideal Florida home, nestled in a quiet gated community only a short drive to the hustle and bustle of Orlando, the fun capital. This cozy 4 bed 3 bath home offers a perfect blend of comfort, style and convenience. A warm and inviting living space with an open- concept layout that flows effortlessly from the entry through the living and dining areas ideal for everyday living or

    Agent Photo

    Dawn Burlace

    Florida Real Estate Navigators

    (863) 887-8571

    308 Terranova Blvd, Winter Haven, FL 33884
  • /2

    $1,475 Per Month

    • 2 Beds
    • 1 Bath
    • 1,206 Sq Ft
    • House for Rent

    850 17th Terrace NE, Winter Haven, FL 33881

    MOVE-IN READYThis home is move-in ready. Schedule your tour now or start your application today.Welcome to this 2-bedroom, 1-bathroom home in Winter Haven, Florida, offering a practical layout and inviting living spaces throughout. An attached carport adds everyday convenience, while the enclosed patio provides additional versatile space to enjoy.Inside, hard surface

    (863) 356-8702

    850 17th Terrace NE, Winter Haven, FL 33881
  • /2

    $369,900

    Sold Feb 11, 2026

    7044 Summit Cir, Winter Haven, FL 33884

    • 4 Beds
    • 2 Baths
    • 2,113 Sq Ft
    • Built 2005

    Last Sold Summary

    • $175/SF
    • 6 Days On Market

    Current Estimated Value $367,452

    Last Listing Agent Arturo Matamoros EXP REALTY LLC

    7044 Summit Cir, Winter Haven, FL 33884
    • /40

      Est $275,426

      Not Listed For Sale

      1436 Wallace Manor Pass, Winter Haven, FL 33880

      • 3 Beds
      • 2 Baths
      • 1,531 Sq Ft
      • Built 2014
      1436 Wallace Manor Pass, Winter Haven, FL 33880

      Last Sold Summary

      • 0 Days On Market

  • /42

    $359,000

    $10K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,476 Sq Ft

    1063 Brimstone Cir, Winter Haven, FL 33884

    Welcome to this stunning 2024-built Ensley model located in the highly sought-after Harmony at Lake Eloise community in Winter Haven, Florida. Offering, 2,476 square feet of beautifully designed living space and over 2,900 total square feet under roof and all exterior block construction. This two-story smart home perfectly blends modern style, comfort, and functionality. Step inside to an

    Agent Photo

    Brad Martin

    BETTER HOMES AND GARDENS REAL ESTATE LIFESTYLES REALTY

    (863) 310-1889

    1063 Brimstone Cir, Winter Haven, FL 33884
  • /20

    $2,595 Per Month

    • 4 Beds
    • 2 Baths
    • 1,851 Sq Ft
    • House for Rent

    397 Corso Loop, Winter Haven, FL 33884

    Property Id: 1220815Beautiful and spacious 4-bedroom, 2-bath single-family home located in the highly desirable Villamar community in Winter Haven. Built in 2020, this modern home features an open-concept floor plan with a bright living area, spacious kitchen, stainless steel appliances, laminate floor throughout, and a large island perfect for entertaining. The split-bedroom layout

    (424) 688-3903

    397 Corso Loop, Winter Haven, FL 33884
  • /2

    $300,000

    Sold Apr 13, 2026

    561 Cody Caleb Dr, Winter Haven, FL 33884

    • 4 Beds
    • 2.5 Baths
    • 2,773 Sq Ft
    • Built 2006

    Last Sold Summary

    • 3% Below List Price
    • $108/SF
    • 61 Days On Market

    Current Estimated Value $301,784

    Last Listing Agent Lesley Guarino CITRAVEST MANAGEMENT LLC

    561 Cody Caleb Dr, Winter Haven, FL 33884
    • /38

      Not Listed For Sale

      304 Temple Ct, Winter Haven, FL 33880

      • 3 Beds
      • 2 Baths
      • 1,456 Sq Ft
      • Built 1986
      304 Temple Ct, Winter Haven, FL 33880

      Last Sold Summary

      • 9 Days On Market

  • /42

    $279,900

    $16K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 1,792 Sq Ft

    104 11th St SE, Winter Haven, FL 33880

    One or more photo(s) has been virtually staged. Welcome to this charming 3-bedroom, 3-bath home located in one of Winter Haven’s most established and sought-after neighborhoods. Situated on a spacious 0.26-acre lot, this property offers timeless character, mature surroundings, and a location rich in local history. A standout feature of the home is the private suite with its own entrance and full

    Agent Photo

    Dave Westphal

    REAL BROKER, LLC

    (863) 340-7511

    104 11th St SE, Winter Haven, FL 33880
  • /13

    $2,125 Per Month

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

    331 Columbo St, Winter Haven, FL 33880

    Apply now or schedule your self-tour today and take the first step toward getting more than just a place to live. Rent with FirstKey Homes for a home that's right for you, plus professional service and maintenance, innovative resident programs, and more… that's the power of purple!This 4-bedroom, 2-bathroom rental home in Winter Haven, FL, may be the right place for you. See the pictures

    (863) 457-3015

    331 Columbo St, Winter Haven, FL 33880
  • /2

    $290,000

    Sold Nov 26, 2025

    1480 Leamington Ln, Winter Haven, FL 33884

    • 4 Beds
    • 2.5 Baths
    • 2,202 Sq Ft
    • Built 2024

    Last Sold Summary

    • 17% Below List Price
    • $132/SF
    • 402 Days On Market

    Current Estimated Value $300,496

    Last Listing Agent Claudia Gutierrez ADAMS HOMES REALTY

    1480 Leamington Ln, Winter Haven, FL 33884
    • /23

      Est $307,377

      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

  • /39

    $309,000

    $9K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,680 Sq Ft

    1799 Carnostie Rd, Winter Haven, FL 33884

    ***PRICE REDUCTION***Your turnkey oasis awaits! Welcome to a home that still feels brand new. This 2022-built gem in the peaceful Villa Mar community offers four spacious bedrooms and a bright, open floor plan designed for making memories. Whether you're hosting a dinner party in the modern kitchen or relaxing on your private, custom-screened lanai, every inch of this 1,680 sq. ft. home reflects

    Agent Photo

    Twanna Dewdney

    LA ROSA REALTY PRESTIGE

    (863) 624-3914

    1799 Carnostie Rd, Winter Haven, FL 33884
  • /16

    $2,180 Per Month

    • 4 Beds
    • 2 Baths
    • 2,101 Sq Ft
    • House for Rent

    3808 Mckinley Dr, Winter Haven, FL 33880

    EXCITING NEWS: WE ARE CURRENTLY RENOVATING THIS HOME! NOTE THAT THE PHOTOS SHOWN REPRESENT THE HOME BEFORE RENOVATION AND DO NOT REFLECT ANY UPDATES. PLANNED IMPROVEMENTS INCLUDE: NEW STAINLESS STEEL APPLIANCES. APPLY TODAY OR ASK YOUR LEASING SPECIALIST FOR MORE DETAILS! Apply now or schedule your self-tour today and take the first step toward getting more than just a place to live. Rent

    (863) 887-7467

    3808 Mckinley Dr, Winter Haven, FL 33880
  • /16

    $269,990

    Sold Apr 02, 2026

    6448 Domizio Dr, Winter Haven, FL 33884

    • 4 Beds
    • 2 Baths
    • 1,874 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • 13% Below List Price
    • $144/SF
    • 60 Days On Market

    Lennar Villa Mar

    6448 Domizio Dr, Winter Haven, FL 33884
    • /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

  • /32

    $299,000

    $46K PRICE DROP Pending
    • 4 Beds
    • 2 Baths
    • 1,665 Sq Ft

    107 Mandolin Dr, Winter Haven, FL 33884

    Under contract-accepting backup offers. SELLER MOTIVATED! | NEW ROOF | NO CDD| GATED COMMUNITY Welcome home to 107 Mandolin Drive, a move-in ready, single-story gem nestled inside the sought-after Mandolin gated community in SE Winter Haven. This beautifully maintained 4-bedroom, 2-bath residence offers the perfect blend of comfort, style, and security, all with No CDD and a low HOA.A

    Agent Photo

    Mabel Vassallo

    CENTURY 21 MYERS REALTY

    (863) 270-2960

    107 Mandolin Dr, Winter Haven, FL 33884
  • /2

    $1,850 Per Month

    • 3 Beds
    • 2 Baths
    • 1,460 Sq Ft
    • House for Rent

    206 Kingshill Ct SE, 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.Interested in this home? You clearly have exceptional taste. This charming 3.0-bedroom, 2.0-bathroom home is not only pet-friendly, but also equipped with smart home features to make everyday life more convenient and

    (863) 343-0941

    206 Kingshill Ct SE, Winter Haven, FL 33884
  • /2

    $325,000

    Sold May 27, 2026

    569 Reggie Rd, Winter Haven, FL 33884

    • 4 Beds
    • 2.5 Baths
    • 1,933 Sq Ft
    • Built 2024

    Last Sold Summary

    • 2% Above List Price
    • $168/SF
    • 9 Days On Market

    Current Estimated Value $314,871

    Last Listing Agent John Hubbert, Jr BHHS FLORIDA PROPERTIES GROUP

    569 Reggie Rd, Winter Haven, FL 33884
    • /2

      Est $285,540

      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

  • /30

    $58,000

    $12K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,296 Sq Ft

    398 Tennis Ln, Winter Haven, FL 33881

    This 2-bedroom, 2-bath home offers 1,296 sq ft of comfortable living with spacious hallways, an open kitchen, and a separate dining area perfect for entertaining. The large living room is filled with natural light and features remote-controlled window shades for effortless comfort. Enjoy Florida living year-round in the oversized screened room with durable polyaspartic flooring (2023)-ideal for

    Agent Photo

    Cindy Minnick

    Sun Resales, Inc.

    (863) 342-6382

    398 Tennis Ln, Winter Haven, FL 33881
  • /14

    $1,175 Per Month

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

    3074 St Paul Dr, Jan Phyl Village, FL 33880

    Property Id: 13559002 Bedroom / 1 Bathroom Home for Rent - Winter Haven, FLAddress: 3078,3076,3074,3072 Saint Paul Drive, Winter Haven, FL(3076 is currently for rent)Affordable 2-bedroom, 1-bathroom single-family home located in a Winter Haven neighborhood walking distance from the Publix plaza. This home offers a comfortable layout, perfect for small families,

    (239) 208-1520

    3074 St Paul Dr, Jan Phyl Village, FL 33880
  • /2

    $299,800

    Sold Aug 15, 2025

    2159 Greenway Dr, Winter Haven, FL 33881

    • 4 Beds
    • 3 Baths
    • 2,030 Sq Ft
    • Built 1971

    Last Sold Summary

    • 8% Below List Price
    • $148/SF
    • 15 Days On Market

    Current Estimated Value $297,199

    Last Listing Agent David Small KELLER WILLIAMS REALTY SMART 1

    2159 Greenway Dr, Winter Haven, FL 33881
    • /23

      Est $318,105

      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

  • /67

    $795,000

    $180K PRICE DROP
    • 4 Beds
    • 4 Baths
    • 3,555 Sq Ft

    200 Island Way, Winter Haven, FL 33884

    Welcome to your own slice of paradise on the private shores of Lake Lewis located in the highly sought-after gated community of Orchid Springs Estates! This stunning Mediterranean-style estate offers the perfect blend of luxury, comfort, and timeless elegance. Boasting 4 spacious bedrooms and 4 full baths, this custom-designed home features a beautifully appointed kitchen ideal for entertaining,

    Agent Photo

    Steve Lockhart

    LOCKHART & ASSOCIATES INC

    (863) 343-1106

    200 Island Way, Winter Haven, FL 33884
  • /16

    $2,250 Per Month

    • 3 Beds
    • 2 Baths
    • 1,555 Sq Ft
    • Condo for Rent

    1708 Teagan Ln, Winter Haven, FL 33884

    Welcome to this charming property located in the beautiful city of Winter Haven, Florida. Offering a spacious living environment, this home is ideal for anyone looking to embrace a comfortable lifestyle in a welcoming community. With nearby conveniences, including a department store and the AdventHealth Lake Wales just 13 minutes away, everything you need is just around the corner.Key

    (914) 537-6515

    1708 Teagan Ln, Winter Haven, FL 33884
  • /2

    $282,990

    Sold Jun 18, 2025

    3479 Costello Cir, Winter Haven, FL 33884

    • 4 Beds
    • 2 Baths
    • 1,665 Sq Ft
    • Built 2024

    Last Sold Summary

    • $170/SF
    • 4 Days On Market

    Current Estimated Value $277,225

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

    3479 Costello Cir, Winter Haven, FL 33884
    • /2

      Est $281,851

      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

Showing Results 161 - 200, Page 5 of 18

How to Buy a Home How to Finance a Home How to Sell a Home