Homes For Sale in Winter Haven 33881 - 308 homes

Remarks: LOW-COST YEAR AROUND LIVING! VERY WELL MAINTAINED! Fully Furnished everything stays! Pet Friendly lot. Gorgeous updating, Very Clean & Move-In ready! Brookhaven Village Resident Owned and located in the heart of Central Florida is a well-established and maintained age 55+ community. You Own your Lot! Perfect for winter months or year around living. Very affordable $34.00 monthly HOA which includes Clubhouse activities, Heated Pool, Shuffleboard, Common grounds maintenance and a boat or trailer storage parking area. This home has numerous updates including a new metal Roof in 2022, New central HVAC 2022, house has been Replumbed, Kitchen and Bath updates and more. This home also features convenient double wide driveway parking, carport, attached utility/workshop/storage, 16X12 Florida porch with screen and vinyl windows, plus a rear 13X11 open patio. No rear neighbors. Located just steps from the Clubhouse/Heated Pool and activities. Take a Look! Easy to show. Quick response to offers and can close fast. All items on property will convey!

Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)

Listing Agent: Don Cleveland, Jr (863-206-4953)

Remarks: Welcome to this 2-bedroom, 2-bathroom ground-floor condo in the desirable Lake Buckeye community. This home features a bonus room and includes the washer and dryer for move-in ease. Step inside and enjoy seamless indoor-outdoor living with a cozy open patio off the dining area. The community enhances your lifestyle with amenities such as a sparkling pool, fishing pier, dock all while showcasing tranquil views of Lake Buckeye that make every day feel like a retreat. Ideally located just minutes from Polk State College, Winter Haven Hospital, Bond and Gessler Clinics, and the lively downtown of Winter Haven, you’ll enjoy easy access to dining, breweries, shopping, the farmers market, and seasonal events. Publix and the Diamond plex sports complex are less than 10 minutes away, Legoland Resort is only 15 minutes, and world-class attractions like Walt Disney World and Universal Studios are about an hour’s drive. With leasing permitted and no age restrictions, this property is an excellent choice for both homeowners and investors. Don’t miss your chance to make it yours.

Listing is courtesy of: KELLER WILLIAMS REALTY SMART 1 (863-508-3000)

Listing Agent: Brian Cox (863-559-3627)

Remarks: One or more photo(s) has been virtually staged. HUGE $15,000 PRICE DROP! Completely renovated and move-in ready, this beautifully updated home combines modern style with everyday comfort in the heart of Central Florida. Step inside to a bright, open floor plan filled with natural light from large floor-to-ceiling windows throughout—including in the bedrooms. The spacious living areas flow seamlessly, creating a warm and inviting atmosphere perfect for both relaxing and entertaining. The stunning kitchen has been completely updated with beautiful soft-close cabinetry, luxurious quartz countertops, stainless steel appliances, and recessed lighting—offering a sleek, contemporary look and exceptional functionality. Luxury vinyl plank flooring runs throughout the home, complemented by fresh interior paint, modern fixtures, and stylish ceiling fans that complete the elegant finish. The primary suite provides a private retreat, while additional bedrooms offer flexibility for family, guests, or a home office. Both bathrooms have been tastefully remodeled with updated tile, vanities, and fixtures. Outside, enjoy your private backyard oasis—fully enclosed with a block wall for enhanced privacy. A sparkling inground pool with paver deck sets the stage for year-round Florida living, whether you’re hosting a gathering or enjoying a quiet evening under the stars. Additional features include a separate exterior laundry/storage room for added convenience. Ideally located near shopping, dining, schools, and major roadways, this home offers easy access to Winter Haven’s famous Chain of Lakes and other nearby Central Florida attractions. Every detail has been updated—move right in and start enjoying the Florida lifestyle today! Schedule your private showing before it’s gone.

Listing is courtesy of: KELLER WILLIAMS REALTY SMART 1 (863-508-3000)

Listing Agent: David Small (407-601-8351)

Remarks: One or more photo(s) has been virtually staged. Spacious 1-story home located in the Elbert Park subdivision of Winter Haven! This property features 3 bedrooms and 2 full bathrooms, offering a functional layout with great potential. The large living room showcases high ceilings, exposed wood beams, ceramic tile flooring, and a wood-burning fireplace—ideal for gatherings and everyday living. The dining area flows seamlessly onto a large screened patio, providing a great space to relax or entertain. The kitchen offers ample space and is ready for your personal updates to create the home you’ve been envisioning. Step outside to enjoy the fully fenced backyard, complete with a large shed for additional storage. Conveniently located near Lake Elbert and Rotary Park, this home offers easy access to outdoor recreation. Don’t miss this opportunity to add value and make this home your own—schedule your private showing today before it’s gone!

Listing is courtesy of: REALTYCITY INC (863-438-6605)

Listing Agent: Jesse Carriedo (863-438-6605)

Remarks: This move-in ready 3-bedroom Winter Haven pool home offers a fantastic combination of comfort, upgrades, and true Florida living on an oversized lot with no HOA. The home features a brand-new roof, new HVAC system and thermostat, new water heater, new pool pump and chlorinator, new laundry units, new exterior front doors, and an expanded driveway with ample parking. Inside, you’ll find a functional layout with generous living space and fresh improvements throughout. The private in-ground pool creates a relaxing backyard setting, while the large lot provides room for outdoor entertaining, storage, or future additions. Located minutes from the Winter Haven Chain of Lakes, Gene’s Lakeside Marina, LEGOLAND Florida Resort, golf courses, shopping, dining, and local parks, this property sits in one of Central Florida’s most desirable and fast-growing areas. With major updates already completed and convenient access to boating, recreation, and upcoming community development, this home is an excellent opportunity for first-time buyers, families, or investors.

Listing is courtesy of: THE URBAN GROUP, INC. (954-522-6226)

Listing Agent: Ashlee Morrell (941-740-9134)

Remarks: HIGE Price Drops!! Sellers Motivated!! Bring us an offer!! Turn Key House on the North Chain of Lakes. 2023 Roof, 2022 POOL! Welcome to this pristine, beautifully maintained home in the quiet and highly desirable Island Lakes community—where there’s no through traffic and peaceful living comes naturally. This property features a newer roof put on in 2023, a newer in-ground pool put in 2022, and a large backyard shed, offering the perfect blend of comfort, storage, and outdoor enjoyment. Step outside and you’ll fall in love with the vinyl-planked dock that gives you direct access to the Chain of Lakes, making it ideal for boating, fishing, and sunset cruises. Whether you prefer relaxing in the screened-in outdoor area or lounging by the sparkling pool, this home is designed for anyone who loves outdoor living. Inside, the home is in immaculate condition. It offers three bedrooms, including a spacious master suite complete with a walk-in tub for easy washing and added convenience. Every room feels well cared for, move-in ready, and prepared for its next owner to enjoy. This stunning property truly has it all—comfort, water access, serenity, and style. It’s ready and waiting for the next buyer who wants to fully embrace lakeside living.

Listing is courtesy of: LA ROSA REALTY PRESTIGE (863-940-4850)

Listing Agent: Keith St. Onge (863-651-1397)

Remarks: Under contract-accepting backup offers. PRICE REDUCED!!!WELCOME to this beautiful 4-bedroom, 2-bath home, built in 2018, offering 1,755 sq. ft. of comfortable living space on a spacious 0.24-acre fenced lot. Located in a desirable area close to shopping, dining, and major roads, this home is perfect for those seeking both convenience and a peaceful neighborhood feel. Step inside and you'll love the bright and airy vaulted great room and the open floor plan, ideal for entertaining or everyday family living. The home features laminate & ceramic flooring throughout the main areas with cozy carpet in all bedrooms. The kitchen is a standout with its beautiful cabinetry, handmade extra shelving, all the appliances, tile backsplash, and plenty of counter space for cooking and gathering. Eagle crest is also a natural gas community, enjoying nonstop hot water with a tank less water heater. Additional thoughtful upgrades include ceiling fans in every room, custom made wood door casings and trim, washer and dryer included, and a screened lanai — the perfect spot to unwind and enjoy the outdoors. The fully fenced backyard provides privacy, security, and space for pets or family fun. The 2-car garage includes a convenient garage screen door, sprinkler system and the home also feature gutters for added protection. This home has been lovingly maintained and is truly move-in ready. Don’t miss your opportunity—call today to schedule your private tour! Some of the furniture is available for sale. CALL TODAY FOR A PRIVATE TOUR ON THIS BEAUTIFUL HOME!!!

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Gaby Murillo (863-668-1914)

Remarks: One or more photo(s) has been virtually staged. Price reduced to $240,000. This newer construction 3-bedroom, 2-bath home offers a compelling opportunity for buyers looking for location, layout flexibility, and upside potential. Built in 2025, the property features an open living area, laminate wood flooring, white cabinetry, stainless steel appliances, and a tankless water heater. The functional floor plan allows for a variety of uses, whether for primary residence, multigenerational living, or investment purposes. Located just minutes from Downtown Winter Haven, the Chain of Lakes, hospitals, shopping, and dining, and with no HOA, this property offers convenience and long-term appeal. Sold as-is.

Listing is courtesy of: KELLER WILLIAMS REALTY SMART (863-577-1234)

Listing Agent: Daryl Ash, Ii (863-934-1548)

Remarks: Under contract-accepting backup offers. Tucked away on a dead-end street in Winter Haven, this spacious lakefront home on Lake Buckeye offers almost 2,400 square feet of living space, a private dock, and a rare combination of privacy, character, and major updates. Situated on over 1/3 of an acre, the property features low traffic, peaceful waterfront views, and a fenced backyard area for pets or animals. Inside, you’ll find a massive living room with triple sliding glass doors overlooking the lake, a floor-to-ceiling stone wood-burning fireplace, and beautiful wood ceilings that create a warm lakeside atmosphere. All 4 bedrooms are positioned on one side of the home, while the oversized living and entertaining areas maximize the waterfront setting and provide excellent flexibility for future remodeling or customization. Major improvements include a metal roof (2019), HVAC system (2016), water heater (2018), upgraded double-pane storm-resistant windows (2010), re-piped plumbing, septic pumped in July 2025, new drain field installed in 2025, and refrigerator replaced in 2023. Lake Buckeye provides a more private setting with fewer homes on the lake while still providing public boat ramp access. Conveniently located a few miles from downtown Winter Haven and only about a mile from Polk State College, this property combines waterfront living, space, and long-term value in a highly convenient location.

Listing is courtesy of: KELLER WILLIAMS REALTY SMART 1 (863-508-3000)

Listing Agent: Don Jerue (863-259-9550)

Remarks: One or more photo(s) has been virtually staged. One or more photos have been virtually staged. 1920s home for sale in Winter Haven with original hardwood floors, updated functionality, and R-3 zoning potential in one of Central Florida’s fastest-growing real estate markets. This move-in ready property offers flexible living space, investment potential, and convenient access to shopping, dining, parks, and the Winter Haven Chain of Lakes. The home features a bright tiled foyer with a large coat closet and direct access to a front bedroom ideal for a home office, guest room, or flex space. The main living and dining areas feature original hardwood flooring and an open layout designed for comfortable living and entertaining. The kitchen includes a refrigerator, range, microwave, and dishwasher for everyday convenience. The split-bedroom floor plan provides added privacy, with the primary suite separated from the secondary bedroom. A bonus flex area near the primary bedroom is ideal for a home office, nursery, gym, or media space. A rear Florida room adds additional square footage and direct driveway access, creating extra space for entertaining, relaxing, or indoor-outdoor living. The R-3 zoning offers added value for investors, rental property buyers, or those exploring future development opportunities. Buyers should verify zoning, permitted uses, and redevelopment options with the City of Winter Haven. Located near downtown Winter Haven, Legoland Florida, major highways, medical facilities, and the Chain of Lakes, this Central Florida property combines location, flexibility, and long-term value. Schedule your private showing today.

Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (863-701-2350)

Listing Agent: Michael Hochadel (863-604-0018)

Remarks: From the moment you walk through the door, this home welcomes you with space, comfort, and endless possibilities. Located in the sought-after Lakeside Landings community, this beautifully designed 4-bedroom, 2.5-bath home offers over 2,400 square feet of thoughtfully designed living space. Featuring an open and airy floor plan, generous living areas, and plenty of room to entertain, this home is perfect for growing families or anyone who loves extra space. The large primary suite creates the perfect private escape, while the backyard offers room to relax and enjoy Florida living year-round. Conveniently situated near shopping, dining, and everything Winter Haven has to offer, this home truly checks all the boxes!

Listing is courtesy of: KELLER WILLIAMS REALTY SMART 1 (863-508-3000)

Listing Agent: Harley Holmes (863-632-6946)

Remarks: Under contract-accepting backup offers. This charming 2-bedroom, 2-bath condo offers the perfect blend of comfort and convenience with a layout designed for effortless living. Enjoy a spacious living area, light-filled interiors, and a private outdoor space perfect for morning coffee or evening wind-downs. Located just minutes from Winter Haven’s famous Chain of Lakes, local dining, shopping, and everyday essentials, this is the ideal spot for year-round living, a seasonal retreat, or a smart investment. Low maintenance. Prime location. Relaxed lifestyle. *This home can be purchased with NO INCOME VERIFICATION*

Listing is courtesy of: ENGEL & VOELKERS LAKELAND (863-412-6633)

Listing Agent: Donna Fiore (904-228-0198)

Remarks: Paradise Awaits !!!! Lakefront Living at its finest...... This cozy one bedroom hideaway could be your Dream Come True! This home is located on Lake Lucerne just a short drive to downtown Winter Haven, Hwy 27, and loads of amenities including shopping, restaurants, and more. Nestled on almost an acre of gorgeous lake frontage, you can enjoy all your favorite things right at home. The living area is on the second level. It includes a nice family room/dining room combo, primary bedroom, bath and kitchen! Everything you need!! The decking on the lakeside gives the best views around Lake Lucerne. Lake Lucerne is a Private lake covering 40 acres. What an awesome location to kick back, relax and enjoy nature at its best. The lower level is currently a storage and laundry area but there is potential for additional living space with a bit of imagination. There is no shortage of storage....2 sheds will allow you plenty of room for all that "Stuff" that you need to put away. There is also a great air-conditioned "Hobby Shack" for you to DO whatever it is you LOVE TO DO!! The possibilities are limitless!! This is a wonderful property that would be great for rental income or just enjoying the lakefront lifestyle..... NO HOA as an added bonus. Don't miss out on this amazing property.....call today to schedule a private showing.

Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)

Listing Agent: Eunice Arroyo-Kirchgessner (863-698-9369)

Remarks: Welcome to this charming 2-bedroom, 1-bath home in the growing city of Winter Haven. Situated on a .16-acre oversized lot, this property offers both comfort and opportunity. The home features a functional layout and a new AC installed in 2024, providing added efficiency and peace of mind. The spacious backyard includes a detached shed with great potential, perfect for a workshop, studio, storage, or a future conversion to fit your needs. Conveniently located just minutes from shopping, dining, and everyday essentials, and close to the new Publix plaza currently under development, this home is perfectly positioned in an area experiencing exciting growth. A great opportunity for homeowners or investors looking to own in one of Winter Haven’s expanding neighborhoods.

Listing is courtesy of: DALTON WADE INC (888-668-8283)

Listing Agent: Pedro Perez, Jr (863-236-8799)

Remarks: Under Construction. The Freeport II floor plan at Willowbrook South offers the perfect blend of comfort, functionality, and modern design. Built with durable all-concrete block construction, this one-story home maximizes living space with a bright, open-concept layout that’s ideal for everyday living and entertaining. As you enter through the foyer, you’ll find two spacious guest bedrooms and a full guest bath with a modern vanity. A convenient linen closet is positioned between the bathroom and bedrooms for easy storage. Further down the hallway, a third bedroom offers flexibility for a home office or guest space, alongside a private laundry area and direct access to the two-car garage. The heart of the home features a well-appointed kitchen with stainless steel appliances, overlooking the dining area, great room, and covered patio perfect for gatherings and family time. Tucked at the rear of the home, the primary bedroom offers a peaceful retreat with a walk-in closet and a spa-inspired bathroom featuring a double vanity sink and a spacious shower. Every home in Willowbrook South comes equipped with the Home Is Connected Smart Home Technology package, allowing you to control locks, thermostat, and more right from your smartphone whether you’re home or away. With its thoughtful design and modern features, the Freeport makes owning a new home in Winter Haven, FL both easy and enjoyable. *Photos are of similar model but not that of the exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability, and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

Listing is courtesy of: DR HORTON REALTY OF CENTRAL FLORIDA LLC (407-250-7299)

Listing Agent: Paul King (407-519-3940)

Remarks: Welcome to this stunning Dream Finders Bradley floorplan, located in the highly sought-after community of Willowbrook near a beautiful golf course in Winter Haven, FL. This spacious 4-bedroom, 2-bath home offers 1,589 square feet of living space and boasts excellent curb appeal due to its impressive elevation. Inside, you'll find gorgeous Gray cabinets complemented by sleek quartz countertops in the kitchen, creating a modern, bright atmosphere. Tile flooring runs throughout the wet and common areas, offering durability and easy maintenance. The open layout is perfect for family gatherings and entertaining guests.

Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)

Listing Agent: Nancy Pruitt, Pa (352-552-7574)

Remarks: HUGE PRICE REDUCTION! POND-VIEW MOVE-IN READY HOME! Enjoy a serene setting and modern updates including tile flooring & kitchen backsplash (2022) and a NEW ROOF (2023). Kitchen features granite countertops and stainless steel refrigerator. Spacious master suite with pond view, walk-in closet, and large bathroom. Split bedroom layout offers privacy and comfort. Located near Lake Smart with Chain of Lakes access! Community offers a pool and is just a short walk to the lake. This community also offers a community dock so bring your poles. Conveniently located near HWY 27, I-4, and HWY 60. Approx. 6 miles to LEGOLAND, 4 miles to Winter Haven Hospital & Publix, and 6 miles to Winter Haven Regional Airport. Furnishings negotiable (TVs do not convey). Schedule your showing today—don’t miss this opportunity!

Listing is courtesy of: CENTURY 21 WATSON & MYERS REALTY (863-324-1000)

Listing Agent: Lamanda Jones (863-557-3627)

Remarks: Built in 2019 and thoughtfully designed for modern living, this well-maintained 4-bedroom, 2-bath residence offers nearly 1,600 square feet of comfortable living space in the established community of Lucerne Park. The single-story layout features an open floor plan that seamlessly connects the living and dining areas, creating an inviting setting for both everyday living and entertaining. Ceramic tile flooring anchors the main living spaces, while the kitchen is equipped with stone countertops, ample cabinetry, and a full appliance package including a built-in oven, range, refrigerator, dishwasher, and disposal. The private primary suite provides a quiet retreat with a spacious walk-in closet and an en-suite bath, while three additional bedrooms offer flexibility for guests, a home office, or hobbies. Additional highlights include central air and heat, a dedicated laundry area, window treatments, and a two-car attached garage. Set on a 0.16-acre homesite with paved streets and sidewalks, the property also features a welcoming front porch and contemporary Florida-style architecture with durable block and stucco construction. Residents of Lucerne Park enjoy deed-restricted community living with golf carts permitted, sidewalks throughout the neighborhood, and convenient access to nearby schools, parks, and everyday amenities. With a low HOA of approximately $30 per month and located in Flood Zone X, this home presents a compelling opportunity for those seeking a newer construction home in Polk County.

Listing is courtesy of: ENGEL & VOLKERS SOUTH TAMPA (813-448-2876)

Listing Agent: Desiree Swanz (813-727-1336)

Remarks: Experience refined lakefront living on the iconic Winter Haven Chain of Lakes, perfectly situated on the coveted shores of Lake Mirror—one of the most picturesque and desirable lakes in the chain. Known for its tranquility, stunning estate homes, and seamless access to the full chain, Lake Mirror offers a rare combination of privacy, beauty, and true waterfront lifestyle. This impeccably maintained 4-bedroom, 3.5-bath residence is a showcase of timeless architecture and elevated design, where every space has been thoughtfully curated to maximize comfort, light, and connection to the outdoors. From the moment you enter, you’re met with expansive living areas, soaring ceilings, and walls of French doors that line the back of the home, flooding the interior with natural light and creating a seamless transition to the outdoor living spaces. These multiple sets of French doors not only enhance the home’s elegance, but also provide direct access from several rooms to the patio, pool, and lakefront setting, blurring the line between indoor and outdoor living in the most effortless way. The outdoor experience is nothing short of exceptional. A resort-style screened pool and spa overlook the water, framed by peaceful lake views and designed for both quiet relaxation and unforgettable entertaining. Whether hosting guests, enjoying a sunset swim, or simply unwinding after a long day, this space delivers a level of serenity that is hard to replicate. Step beyond to your private dock and embrace everything the Chain of Lakes lifestyle has—boating to dinner, skiing across open water, fishing at sunrise, and cruising through one of Central Florida’s most connected and sought-after lake systems. Additional highlights include a brand-new seamless metal roof in 2025, an expansive 3-car garage, and meticulous pride of ownership throughout, ensuring both beauty and peace of mind. This is a rare opportunity to own a home where luxury, lifestyle, and location come together effortlessly—a true lakefront retreat in the heart of Winter Haven.

Listing is courtesy of: THE MARKET REALTY COMPANY (863-999-4643)

Listing Agent: Brock Jennings (863-990-5846)

Remarks: Under contract-accepting backup offers. Welcome to this charming 2-bedroom, 1-bathroom home in the West Cannon Heights neighborhood of Winter Haven, an excellent opportunity for first-time buyers or investors. With a really large open kitchen, this home is move-in ready. The exterior features a covered parking area and a workshop with a new roof. This property offers a cozy living space and a convenient location, with no HOA fees. Don't miss the chance to own this piece of Winter Haven.

Listing is courtesy of: PEOPLE'S CHOICE REALTY SVC LLC (813-933-0677)

Listing Agent: Pablo Lluveras Matos (813-406-3652)