32

4-Bedroom Houses in Winter Haven, FL under $500,000

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  • /50

    $409,900

    • 4 Beds
    • 2 Baths
    • 2,376 Sq Ft

    4346 Thomas Wood Ln E, Winter Haven, FL 33880

    Spacious 4-Bedroom Home in Winter Haven, FL – Bring Your Boat, RV & More!Welcome to this updated and move-in-ready 4-bedroom, 2-bathroom home in beautiful Winter Haven! Situated on a generous lot with plenty of room to roam, this property offers the ideal setup for families, hobbyists, and outdoor enthusiasts alike. With no HOA restrictions, you’re free to bring your boat, RV, or any other

    Carmelo Velez ELEVATE REAL ESTATE BROKERS OF FLORIDA LLC

    4346 Thomas Wood Ln E, Winter Haven, FL 33880
  • /47

    $416,900

    • 4 Beds
    • 3 Baths
    • 2,302 Sq Ft

    2980 Dayton Dr, Winter Haven, FL 33884

    Experience the best of Florida’s 55+ lifestyle at 2980 Dayton Drive. A refined offering set on a large corner lot in Traditions at Lake Ruby, one of Winter Haven’s active adult communities. Impeccably maintained and thoughtfully designed, this 4-bedroom, 3-bath residence offers the perfect blend of comfort, elegance, and convenience — whether you’re seeking a full-time retreat or a seasonal

    Ryan Mullis NEXTHOME NORRIS & COMPANY REALTY

    2980 Dayton Dr, Winter Haven, FL 33884
  • /40

    $449,990

    • 4 Beds
    • 2 Baths
    • 1,855 Sq Ft

    4027 Island Lakes Dr, Winter Haven, FL 33881

    Welcome to your dream lakefront retreat on the Chain of Lakes. Situated on the picturesque shores of Lake Conine, this property offers direct access to the extensive canal system of the Chain of Lakes, opening up endless opportunities for fishing, boating, water skiing, paddleboarding, and canoeing. Imagine spending your days on the water, enjoying all the recreational activities this vibrant

    David Small KELLER WILLIAMS REALTY SMART 1

    4027 Island Lakes Dr, Winter Haven, FL 33881
  • /55

    $450,000 Open Sun 11AM - 2PM

    • 4 Beds
    • 3 Baths
    • 2,067 Sq Ft

    4812 Mandolin Ct, Winter Haven, FL 33884

    Welcome to this stunning 4-bedroom, 3-bathroom home with a dedicated office and a sparkling inground saltwater pool, nestled in the gated community of Mandolin. From the moment you step inside, you’ll appreciate the seamless flow of laminate flooring throughout—offering a clean, carpet-free living experience. The heart of the home is the spacious, open-concept kitchen, featuring stone

    John Hubbert, Jr BHHS FLORIDA PROPERTIES GROUP

    4812 Mandolin Ct, Winter Haven, FL 33884
  • /27

    $440,000

    • 4 Beds
    • 3 Baths
    • 2,420 Sq Ft

    415 Smiley Ct, Winter Haven, FL 33884

    3 spacious bedrooms + 1 versatile study/office??? Large great room with excellent natural light??? Open kitchen integrated into the dining room, ideal for family sharing?? 3 full bathrooms: ?? Covered garage for 3 vehicles?? Large private pool with terrace area for outdoor enjoyment?? Large side garden, perfect for games, pets, or

    Adriana Sanchez AGENT TRUST REALTY CORPORATION

    415 Smiley Ct, Winter Haven, FL 33884
  • /48

    $459,000

    • 4 Beds
    • 2 Baths
    • 2,369 Sq Ft

    1081 Sandpiper Loop, Winter Haven, FL 33881

    Welcome to 1081 Sandpiper Loop, a stunning home in a quiet, exclusive community of fewer than 90 homes. Nestled just off Country Club Road in Winter Haven, this property offers the perfect balance of privacy and convenience—close to downtown, yet featuring spacious 1⁄4-acre lots so you’ll never feel crowded.Step inside to beautiful vinyl flooring throughout the common areas, creating a modern,

    Chris Loschiavo RE/MAX HERITAGE PROFESSIONALS

    1081 Sandpiper Loop, Winter Haven, FL 33881
  • /54

    $444,900

    • 4 Beds
    • 4 Baths
    • 3,586 Sq Ft

    16 Golfview Cir NE, Winter Haven, FL 33881

    Large and lovely mid-century pool home in the heart of Winter Haven/North Lake Elbert Heights, near Polk State College, Lake Elbert, the Diamondplex Sports Complex, and beautiful and vibrant downtown! Enter the foyer to the living room and formal dining room with newer wood floors throughout and plenty of space for dinner parties and family time. The bright chef's kitchen has numerous cabinets, a

    Natalie Oldenkamp BHHS FLORIDA PROPERTIES GROUP

    16 Golfview Cir NE, Winter Haven, FL 33881
  • /50

    $440,000

    • 4 Beds
    • 2 Baths
    • 1,982 Sq Ft

    260 Lake Smart Cir, Winter Haven, FL 33881

    Experience the perfect blend of style, comfort, and sustainability in this beautifully maintained 4-bedroom, 2-bathroom home, built in 2021. Nestled in a serene neighborhood, this home offers not only modern features but also breathtaking views of Lake Smart which it's part of Polk County Chain of Lakes. Highlights Include: Stunning lake view to enjoy daily sunrises, sunsets, and peaceful vibes.

    Veddy Diaz Rosario CHARLES RUTENBERG REALTY ORLANDO

    260 Lake Smart Cir, Winter Haven, FL 33881
  • /39

    $458,000

    • 4 Beds
    • 3 Baths
    • 2,433 Sq Ft

    212 Terranova Blvd, Winter Haven, FL 33884

    100% FINANCING AVAILABLE – NO PMI AND NO INCOME LIMIT – MAKING THIS HOME THE BEST OPTION FOR YOU AND YOUR FAMILY! This elegant and impeccably maintained 4-bedroom, 3-bath former model home with a solar-heated pool is located in a beautiful gated community and offers stunning conservation views. Used only as a second residence, it features a spacious layout with soaring ceilings, wood floors,

    Valerie Casals INVESTOR'S REAL ESTATE LLC

    212 Terranova Blvd, Winter Haven, FL 33884
  • /20

    $440,000

    • 4 Beds
    • 3 Baths
    • 2,513 Sq Ft

    1924 Eloise Cove Dr, Winter Haven, FL 33884

    Welcome to 1924 Eloise Cove Drive, a spacious 4 bedroom home with 3 full baths in the desirable gated community of Eloise Cove. Residents of Eloise Cove enjoy the security of a gated community and access to the stunning Chain of Lakes via Lake Eloise, making it easy to enjoy boating, fishing, and the natural beauty that makes Winter Haven such a special place to live.Inside the home, you’ll

    Melanie Thomas REAL BROKER, LLC

    1924 Eloise Cove Dr, Winter Haven, FL 33884
  • /35

    $485,000

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

    305 Hernando Rd, Winter Haven, FL 33884

    Welcome to your Dream home!! Step into this stunning residence 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 suite. This home has a formal living area, family

    Sherry Sapp COLDWELL BANKER REALTY

    305 Hernando Rd, Winter Haven, FL 33884
  • /39

    $400,000

    • 4 Beds
    • 3.5 Baths
    • 2,194 Sq Ft

    1317 Avenue A SE, Winter Haven, FL 33880

    Welcome to 1317 Avenue A SE in Winter Haven, FL – A truly one-of-a-kind! This 4-bedroom, 3.5-bath home (including an en suite) is overflowing with charm, character, and endless potential! Step into your private outdoor oasis featuring an inviting inground pool and a spacious screened-in porch—perfect for relaxing, entertaining, or enjoying your morning coffee in comfort.Inside, the home

    Don Jerue KELLER WILLIAMS REALTY SMART 1

    1317 Avenue A SE, Winter Haven, FL 33880
  • /35

    $430,000

    • 4 Beds
    • 3 Baths

    459 Lanham Dr, Winter Haven, FL 33881

    Incredible seller financing opportunity—no banks, no hassle! Enjoy flexible terms with a 30-year fixed rate and easy qualification based on debt-to-income. This beautifully maintained, fully furnished home sits in the gated community of Sanctuary by the Lake, offering exclusive access to peaceful lake views, parks, and playgrounds. Perfect for a first-time buyer or someone seeking simplicity and

    Carlton Watson Listing Spark South Florida

    459 Lanham Dr, Winter Haven, FL 33881
  • /52

    $420,000

    • 4 Beds
    • 2 Baths
    • 1,960 Sq Ft

    301 Terranova Blvd, Winter Haven, FL 33884

    Welcome to your dream home at 301 Terranova Blvd, Winter Haven, FL! Located within an exclusive gated community that offers privacy, security, and peace of mind. Homes in rarely come on the market, making it one of the safest and most sought-after areas.This elegant property features spacious interiors, abundant natural light, and a modern, functional design—perfect for family living or

    Rosa Nieves LPT REALTY, LLC

    301 Terranova Blvd, Winter Haven, FL 33884
  • /47

    $425,000

    • 4 Beds
    • 2 Baths
    • 2,069 Sq Ft

    114 Belmont Dr, Winter Haven, FL 33884

    Welcome to this spacious and beautifully designed pool home, perfect for entertaining and family living! As you step through the front door, you’re welcomed by a tiled foyer leading to a formal dining room with elegant wood laminate flooring and a cozy den that overlooks the pool area.The kitchen features tile flooring, a gas stove, abundant cabinetry, and a farmhouse sink with views of the

    Stacey Towns STACEY TOWNS REALTY LLC

    114 Belmont Dr, Winter Haven, FL 33884
  • /24

    $419,900

    • 4 Beds
    • 2.5 Baths
    • 3,055 Sq Ft

    673 Sarner Pass Way, Winter Haven, FL 33881

    Beautiful property in an oversize lot ( 15,550 sq ft , more than 1/3 of acre ) over 3000 sq ft under air, all tile on the first floor, upon entereing the home it features an office, overlooking the formal dining and living area, behind that is oversize family room and the elegant kitchen, featuring all stainless steel appliances , you are also going to find the oversize lanai in the back of the

    Consuelo Zea ZEA REALTY & ASSOCIATES

    673 Sarner Pass Way, Winter Haven, FL 33881
  • /20

    $420,000 Open Sun 12PM - 3PM

    • 4 Beds
    • 3 Baths
    • 2,320 Sq Ft

    3986 Bedford Ave, Winter Haven, FL 33884

    >> Spacious 4-Bed, 3-Bath Home in the Premier Gated Community of Traditions at Lake Ruby!>> Welcome to your dream home in one of Central Florida’s most desirable active communities! This beautifully designed 4-bedroom, 3-bath residence sits on an oversized lot with no rear neighbors, offering ultimate privacy and tranquil pond views. >> Inside, you’ll love the triple-split floor plan—well

    Steven Koleno BEYCOME OF FLORIDA LLC

    3986 Bedford Ave, Winter Haven, FL 33884
  • /33

    $469,000

    • 4 Beds
    • 3 Baths
    • 2,277 Sq Ft

    3998 Bedford Ave, Winter Haven, FL 33884

    If you are looking for a home in an active community with all the comfort, safety and amenities that your heart could desire for entertaining and water views, then you have finally found your home. This 4/3 Kennedy model with upgrades including tile plank flooring, crown molding, and an extended lanai with screen enclosure and outside patio is a unique opportunity to own the home of your dreams.

    Steven Koleno BEYCOME OF FLORIDA LLC

    3998 Bedford Ave, Winter Haven, FL 33884
  • /76

    $499,000 Open Sun 1PM - 4PM

    • 4 Beds
    • 2 Baths
    • 3,198 Sq Ft

    934 Lake Elbert Dr SE, Winter Haven, FL 33880

    Welcome to this beautifully preserved lakeside home, offering more than 3,100 square feet of versatile living space on over half an acre of direct lakefront property along the scenic shores of Lake Elbert in the heart of Winter Haven.The story goes that this home was originally built in 1926 as one of a pair of nearly identical homes for two brothers and their families, this charming

    Chris Renfro KELLER WILLIAMS REALTY SMART

    934 Lake Elbert Dr SE, Winter Haven, FL 33880
  • /31

    $420,000

    • 4 Beds
    • 2.5 Baths
    • 3,075 Sq Ft

    439 Sunfish Dr, Winter Haven, FL 33881

    **Elegant Two-Story Residence in the Sought-After Lake Lucerne Community** 4 Bedroom 2.5 Bath Plus a Den!Welcome to this impeccably maintained, two-story KB Home nestled on an expansive 70’ x 130’ home-site in the prestigious Lake Lucerne enclave. This distinguished property offers refined living with privacy and tranquility, fully enclosed by a premium vinyl fencing

    Harry D'Onofrio BEST HOMES, LLC.

    439 Sunfish Dr, Winter Haven, FL 33881
  • /46

    $410,000

    • 4 Beds
    • 2.5 Baths
    • 2,364 Sq Ft

    2674 San Marco Way, Winter Haven, FL 33884

    PREFERRED LENDER IS OFFERING UP TO $5,000 Towards Buyers Closing Costs or Rate Buy Down! Discover this stunning 2023 upgraded, move-in ready home that effortlessly blends style, space, and smart functionality. From the moment you step inside, you’re welcomed by a formal dining room ideal as a versatile flex space or a private home office. The heart of the home features a bright, open-concept

    Amy Kozelka CENTURY 21 CIRCLE

    2674 San Marco Way, Winter Haven, FL 33884
  • /10

    $400,000

    • 4 Beds
    • 2.5 Baths
    • 3,016 Sq Ft

    709 Sarner Pass Way, Winter Haven, FL 33881

    Beautiful 2 Story home ready for you. Home built in 2021, comes with a spacious 4 bedrooms & 2 and half bath home that sits on a larger lot. Home is ready to be moved into. Property has solar panels attached. Great short term rental home for investors.

    Marisol Ortega GATAP REALTY

    709 Sarner Pass Way, Winter Haven, FL 33881
  • /47

    $484,900

    • 4 Beds
    • 2.5 Baths
    • 3,472 Sq Ft

    2 Bridgewater Dr, Winter Haven, FL 33884

    *** SIGNIFICANT SAVINGS-HUGE PRICE REDUCTION*** Welcome home to 2 Bridgewater Drive, Winter Haven, Fl. This 4 bedroom, 2.5 bath, two-story pool home is located in the coveted Bridgewater community, just down the road from Legoland!As you step inside, you are greeted with 19' ceilings in the spacious living room, complemented by a double-sided wood-burning fireplace extending into the

    Jessica Hancock-Batson THE STONES REAL ESTATE FIRM

    2 Bridgewater Dr, Winter Haven, FL 33884
  • /49

    $457,500

    • 4 Beds
    • 2.5 Baths
    • 2,797 Sq Ft

    3217 La Salle St, Winter Haven, FL 33884

    Discover your dream home! This gorgeous, better-than-new 4-bedroom, 2.5-bath residence, built in 2023, offers an impressive nearly 2,800 sq. ft. of luxurious living space. Nestled in an exclusive 42-home community, this gem comes with NO CDD fees and a remarkably LOW annual HOA fee of just $780—an outstanding value in a prime location! Positioned between serene Lake Eloise and picturesque Lake

    Kelly Jones KELLER WILLIAMS REALTY SMART 1

    3217 La Salle St, Winter Haven, FL 33884
  • /34

    $482,000

    • 4 Beds
    • 3 Baths
    • 2,663 Sq Ft

    148 Lake Otis Rd, Winter Haven, FL 33884

    Spacious 4-Bedroom, 3-Bath Pool Home in the admired Lakewood Community. Nestled on an oversized lot with mature trees, this remodeled tri-level home offers a perfect blend of modern luxury and comfort. With a spacious layout, a private pool, and an abundance of natural light, this home is designed for both relaxation and entertaining. As you enter, you’ll immediately notice the bright and airy

    Michelle Armbruster LOCKHART & ASSOCIATES INC

    148 Lake Otis Rd, Winter Haven, FL 33884
  • /25

    $465,000

    • 4 Beds
    • 2 Baths
    • 2,367 Sq Ft

    415 Ruby Lake Place, Winter Haven, FL 33884

    This home sounds like an amazing opportunity! Located in the gated and upscale Ruby Lake community, it offers a fantastic combination of convenience and luxury. With its beautiful 4 bedrooms and 2 bathrooms, it’s spacious enough for both family and guests, and the fresh updates like a new roof, AC, water heater, and freshly painted pool deck give it a move-in-ready feel. The stamped concrete

    Susan Brown COLDWELL BANKER REALTY

    415 Ruby Lake Place, Winter Haven, FL 33884
  • /38

    $419,900

    • 4 Beds
    • 2.5 Baths
    • 2,364 Sq Ft

    953 Cambridge Dr, Winter Haven, FL 33881

    Stunning 4-Bedroom Home in Lucerne Park Reserve, Winter Haven, FL – For Sale!Welcome to 953 Cambridge Dr, Winter Haven, FL 33881—a beautifully designed 4-bedroom, 2.5-bathroom home located in the highly sought-after Lucerne Park Reserve community. Nestled on a prime corner lot, this home offers modern design, spacious living, and a vibrant community—perfect for families and professionals

    Martha Ramirez B&T REALTY AND MANAGEMENT GROUP LLC

    953 Cambridge Dr, Winter Haven, FL 33881
  • /26

    $407,000

    • 4 Beds
    • 3.5 Baths
    • 2,513 Sq Ft

    1125 Michelangelo Ln, Winter Haven, FL 33884

    HUGE PRICE REDUCTION! SELLER MOTIVATED! Welcome to your meticulously maintained, BETTER THAN NEW home in the exclusive Estates of Lake Florence! This stunning Bayshore floor plan features a single-story, open-concept design that beautifully balances style and functionality. With a layout tailored to your needs, this home is exactly what you’ve been looking for! The designer kitchen showcases a

    Kevin Mize REDFIN CORPORATION

    1125 Michelangelo Ln, Winter Haven, FL 33884
  • /37

    $457,400

    • 4 Beds
    • 2.5 Baths
    • 2,495 Sq Ft

    108 Lake Region Blvd N, Winter Haven, FL 33881

    PRICE REDUCTION of 10k!!! OWNER MOTIVATED!!! Wow, get ready to fall in love with this beautiful custom built home near Winter Haven Country Club! This stunning home built by Alan Ulch Construction is the first home built in Winter Haven using Ytong concrete block which increase the energy efficiency of the home. Energy bills are about half of homes built with regular concrete block. This elegant

    Matthew Hazlett EXP REALTY LLC

    108 Lake Region Blvd N, Winter Haven, FL 33881
  • /2

    $416,105 New Construction

    • 4 Beds
    • 3 Baths
    • 2,773 Sq Ft

    2502 Sage Valley Way, Winter Haven, FL 33884

    Under Construction. Find everything you need in Harmony on Lake Eloise! Located just minutes from world class theme parks and attractions, Harmony on Lake Eloise is the perfect community to call home with its beautiful Florida lifestyle and amenities. This community boasts stunning home sites. You'll enjoy the sparkling local lakes practically in your backyard and the best local restaurants and

    Paul King DR HORTON REALTY OF CENTRAL FLORIDA LLC

    2502 Sage Valley Way, Winter Haven, FL 33884
  • /2

    $416,105 Open Sun 12PM - 6PM

    • 4 Beds
    • 3 Baths
    • 2,773 Sq Ft

    2602 Sage Valley Way, Winter Haven, FL 33884

    Under Construction. Find everything you need in Harmony on Lake Eloise! Located just minutes from world class theme parks and attractions, Harmony on Lake Eloise is the perfect community to call home with its beautiful Florida lifestyle and amenities. This community boasts stunning home sites. You'll enjoy the sparkling local lakes practically in your backyard and the best local restaurants and

    Paul King DR HORTON REALTY OF CENTRAL FLORIDA LLC

    2602 Sage Valley Way, Winter Haven, FL 33884
  • /2

    $416,605 New Construction

    • 4 Beds
    • 3 Baths
    • 2,773 Sq Ft

    2598 Sage Valley Way, Winter Haven, FL 33884

    Under Construction. Find everything you need in Harmony on Lake Eloise! Located just minutes from world class theme parks and attractions, Harmony on Lake Eloise is the perfect community to call home with its beautiful Florida lifestyle and amenities. This community boasts stunning home sites. You'll enjoy the sparkling local lakes practically in your backyard and the best local restaurants and

    Paul King DR HORTON REALTY OF CENTRAL FLORIDA LLC

    2598 Sage Valley Way, Winter Haven, FL 33884

Home Trends in Winter Haven, FL

Housing Trends

Median Sale Price
$285,000
Median Single Family Sale Price
$300,000
Median Townhouse Sale Price
$265,825
Median 2 Bedroom Sale Price
$150,500
Median 1 Bedroom Sale Price
$102,500
Average Price Per Sq Ft
$173
Number of Homes for Sale
889
Last 12 months Home Sales
1,852
Months of Supply
5.80
Median List Price
$310,000
Median Change From 1st List Price
4%
Median Home Sale Price YoY Change
-4%
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