Homes For Sale in Winter Haven 33881 - 286 homes

Remarks: Welcome to this beautifully built 2022 new construction home in Winter Haven, FL, offering the perfect blend of modern design, energy efficiency, and affordability — all conveniently located near Orlando’s world-famous attractions, including Walt Disney World and Universal Studios. Built by one of Winter Haven’s most recognized affordable builders, J&S Properties, this 3-bedroom, 2-bathroom, 2-car garage home features 1,421 square feet of thoughtfully designed living space with an open-concept floor plan ideal for both everyday living and entertaining. Step inside to find tray ceilings in the living room and primary suite, enhancing the home’s spacious feel, along with LED recessed lighting throughout and abundant natural light. The kitchen is equipped with granite countertops, solid wood soft-close cabinetry, and energy-efficient appliances, combining style with functionality. This home is loaded with upgrades and energy-saving features, including efficient pull-out windows, architectural 30-year shingles, Decora switches, ceiling fans throughout, and window blinds already in place — making it truly move-in ready. Enjoy the benefits of new construction in Central Florida without the wait to build, all in a location that offers easy access to Orlando, Lakeland, Tampa, shopping, dining, and major highways.

Listing is courtesy of: REAL BROKER, LLC (855-450-0442)

Listing Agent: Regan Fuller (727-243-6216)

Remarks: 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)

Remarks: Back to the Market – Get $5,000 to help with your closing costs. Turnkey duplex generating immediate income $2550 from day one! Located at 3356 Avenue Q NW, this well-maintained property features two spacious 2-bed/1-bath units, both currently leased to reliable tenants. No vacancies, no renovations needed—just steady rental income. Situated in a quiet, established neighborhood, the property is surrounded by public schools within a 2-mile radius, making it appealing for families and long-term renters. One of its biggest draws is proximity to Winter Haven’s famous Chain of Lakes, offering public boat ramps, fishing spots, scenic parks, and walking/biking trails. Nearby Lake Shipp Park and South Lake Howard Nature Park provide playgrounds, picnic areas, and space for outdoor activities. The location offers quick access to shopping, dining, and community amenities, while remaining peaceful and residential. LEGOLAND Florida Theme Park is just 20 minutes away, adding even more appeal for tenants seeking convenience and recreation. Whether you’re an experienced investor or just starting your portfolio, this property checks all the boxes: consistent rental history, excellent location, tenant appeal, and low-maintenance operation. Opportunities like this in such a desirable area don’t last—secure your income-producing asset today!

Listing is courtesy of: BANERSY REAL ESTATE, LLC (407-962-6201)

Listing Agent: Enrique Ojeda (321-946-8241)

Remarks: Una oportunidad difícil de encontrar en Florida. Esta propiedad de 3 habitaciones y 1.5 baño se encuentra en un amplio lote de 10,000 sq ft, con hermosa vista al lago y sin HOA, ofreciendo mayor libertad y espacio para disfrutar o ampliar la propiedad. Ubicada sobre una vía principal en Winter Haven, cerca de escuelas, comercios y servicios, lo que la convierte en una opción muy conveniente para vivir o invertir. Además, cuenta con techo nuevo del 2023 (aprox. 1.5 años), un valor agregado importante para el comprador. Ideal para primer comprador o inversión, y con posibilidad de aplicar a programas de ayuda para el down payment y gastos de cierre.

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

Listing Agent: Leidy Marroquin Bello (321-408-1934)

Remarks: Welcome home to this inviting upstairs condo located in the peaceful Lake Buckeye Condo community, where tranquil lake views and relaxed living come together. Step inside to find laminate and ceramic tile flooring throughout, offering both durability and easy maintenance. The open living and dining area is light and welcoming, seamlessly extending to a private 3x7 balcony, the perfect place to enjoy your morning coffee or unwind at the end of the day. Just beyond, the well-appointed kitchen comes complete with all appliances, granite countertops, and an adjacent utility room with washer/dryer hookups and extra cabinet storage. The split-bedroom floor plan provides excellent privacy. The primary suite features a walk-in closet and a private en-suite bathroom with a walk-in tile shower, while the second bedroom is conveniently located near the hall bath, ideal for guests or a home office. Residents enjoy access to community amenities, including a sparkling pool overlooking beautiful Lake Buckeye and community docks, perfect for lakeside relaxation and peaceful views. This condo offers a wonderful blend of comfort, convenience, and serene surroundings—an opportunity you won’t want to miss!

Listing is courtesy of: STAR REALTY OF WINTER HAVEN (863-299-7827)

Listing Agent: Carlee Marchetti (863-258-3338)

Remarks: Under contract-accepting backup offers. Turn-Key Furnished Home in Lakefront 55+ Community Welcome to easy Florida living in the peaceful 55+ lakefront community of Lake Henry. This fully furnished 2-bedroom, 2-bath home is truly move-in ready, offering comfort, convenience, and a relaxed lifestyle just steps from the water. Inside, you'll find a bright and inviting layout with a spacious living area, functional kitchen, and dining space perfect for everyday living or hosting guests. The home includes all furnishings, making it an ideal option for seasonal residents, snowbirds, or anyone looking for a turnkey Florida retreat. Additional features include: • Covered carport parking • Utility/laundry room with extra storage • Spacious primary suite with private bath • Comfortable guest bedroom and second full bath • Low-maintenance living Residents enjoy access to community amenities including a community pool, social activities, and a private dock on Lake Henry, perfect for fishing, relaxing sunsets, and enjoying Florida's beautiful outdoors. Located in the heart of Winter Haven, you're just minutes from shopping, dining, golf courses, and medical facilities. Whether you're looking for a full-time residence, seasonal getaway, or low-maintenance retirement lifestyle, this furnished home offers incredible value in a welcoming community. Schedule your private showing today and experience the relaxed Florida lifestyle this home has to offer.

Listing is courtesy of: KELLER WILLIAMS RLTY NEW TAMPA (813-994-4422)

Listing Agent: Mario Paniagua Ovando (813-953-6003)

Remarks: Welcome to Winter Haven Harbor condos a 55+ community. This two bedroom one bath condo is an end unit and it is on the first floor, very close to your parking spot. The home has Nice laminate flooring throughout. The Dining room is next to kitchen, a little open concept area. The master bedroom has a nice size walk in closet. The home also boasts new energy efficient windows. The community features a massive heated pool, clubhouse with exercise room, kitchen, pool table, shuffleboard, and a grilling area with a nice area to entertain friends and family. This community also features a car washing area. Public bus transportation-Citrus connection available right out front. Buyer approval required. You are walking distance from shopping, Hospital and other medical centers. Centrally located between Tampa and Orlando. Schedule your appointment to view this home and make it yours today.

Listing is courtesy of: HARPER REALTY FL, LLC (863-687-8020)

Listing Agent: Annie Wood (321-229-1913)

Remarks: Discover your serene retreat at Winter Haven Harbour Condos—a charming 55+ community featuring this delightful third-floor, two-bedroom, one-and-a-half-bath residence. Recently refreshed 3 years ago with a brand-new roof, fresh paint, and plush new carpeting in both bedrooms and the living space, this home is move-in ready. The kitchen is bright and functional, with plenty of cabinetry that extends into the dining area and ceramic tile flows seamlessly through the kitchen and baths. Enjoy a screened front porch, perfect for morning coffee. The community offers a large heated pool, a clubhouse, shuffleboard, and a grilling area—ideal for gatherings. Conveniently located near shopping, medical centers, and with easy access to both Tampa and Orlando, this is a rare opportunity. Schedule your private tour today!

Listing is courtesy of: HARPER REALTY FL, LLC (863-687-8020)

Listing Agent: Annie Wood (321-229-1913)

Remarks: One or more photo(s) has been virtually staged. Seller is offering $5,000 towards the buyers closing costs and prepaids! Completed in 2020 and ready for immediate occupancy, this property blends modern construction with thoughtful recent upgrades. Notable features include a brand-new roof installed in 2023, fully paid solar panels, a freshly painted interior, and professionally serviced and cleaned air ducts, all contributing to energy efficiency and average utility costs of approximately $85–$100 a month. The home is equipped with smart home technology and constructed with concrete block on both the first and second floors, offering added durability and peace of mind. Inside, the kitchen opens naturally to the main living spaces, creating an inviting layout for everyday living and entertaining. A future flooring update provides an easy opportunity to personalize the space. Bedrooms are generously sized, with the primary suite located upstairs, and a fully fenced backyard enhances privacy and functionality. Ideally positioned within the community, the home is just a short walk to the mailbox, pool, and playground, with convenient access to shopping, dining, grocery stores, major roadways, just a short drive to LEGOLAND® and less then one hour from Walt Disney World.

Listing is courtesy of: KELLER WILLIAMS ADVANTAGE REALTY (407-977-7600)

Listing Agent: Kristin Duncan (407-274-5911)

Remarks: Fall in love with this expansive 5-bedroom, 3-bath, 3-car garage home situated on a quarter-acre of land, where luxury, functionality, and energy efficiency come together. Explore every corner of this stunning property right now through a 3D interactive walkthrough or a full video tour. Designed with an open layout and split bedrooms for privacy, the home feels massive yet efficient. The heart of the home is a wide-open living area and a huge kitchen featuring a gigantic island, 42-inch upper cabinets, a spacious pantry, and top-of-the-line stainless steel appliances. Whether you are relaxing, hosting, or cooking, the home provides boundless space to move and mingle. High-quality finishes are found throughout, including granite countertops in the bathrooms, luxury vinyl plank flooring in the main areas, and premium carpeting in the bedrooms. This isn't just a home; it’s an investment featuring $30,000 in upgrades available for your review! One of the standout benefits of this property is the incredible energy efficiency. Powered by solar panels plus a solar-powered attic fan, the home’s energy costs are cut in half compared to neighboring homes that have much smaller living areas. The solar panel lease is a manageable $180 a month, which keeps the actual electric bill payable to TECO energy as low as $5 to $20 a month. For added convenience, the home also includes a paid security system and a water softener system paired with reverse osmosis in the kitchen. The outdoor space is just as impressive, featuring a large, private backyard on a quarter-acre lot fully enclosed by a vinyl fence. You can enjoy the Florida weather from the comfort of a huge, screened-in lanai, surrounded by custom pavers that wrap seamlessly around the sides and back of the home. The meticulous landscaping is easily maintained by a full irrigation system. Located in a quiet, peaceful community in Polk County, you are perfectly positioned near Highway 27 for an easy drive to Disney and the Orlando Airport. Best of all, there are no CDD fees and a low HOA of only $725 a year. This home is being sold AS IS and is ready for you to move in. Schedule your showing today!

Listing is courtesy of: MAZELG REALTY (863-399-0226)

Listing Agent: Mary Sorrell (765-434-1802)

Remarks: One or more photo(s) has been virtually staged. Welcome to 6450 Hollyberry Lane in Brookhaven Village—a highly sought-after 55+ community where you own your land, making this a rare opportunity! This beautifully updated, move-in ready home features new luxury vinyl flooring (2025) and a bright, open layout perfect for everyday living and entertaining. The upgraded kitchen offers butcher block countertops, slide-out metal racks for added storage, and a brand-new dishwasher. Washer and dryer are included. Both bathrooms have been beautifully remodeled with modern finishes. Major updates include a new roof (Dec 2024), new HVAC system (2025) with ductwork and air handler, new windows (2025), and all-new screening, including the lanai with vinyl windows—perfect for enjoying Florida living year-round. The home is also fully replumbed with updated anchors and straps, including a vapor barrier that was installed about 4 years ago. The home also includes a great storage shed/workshop—ideal for hobbies or extra storage. Enjoy a super low HOA with access to a community pool and clubhouse, all in the heart of Winter Haven near shopping, dining, and lakes. Fully updated + land ownership + prime 55+ community—this one stands out. Schedule your showing today!

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. SUPER DEAL on a big four bedroom home! Clean, fresh and well maintained home! PLUS, an American Preferred Home Warranty is included! With American Home Warranty, if you ever need to use it, you get to choose your own preferred vendors! Enjoy room for the family and privacy for mom and dad in the spacious split bedroom layout . You are going to like the open-concept living areas, big island kitchen with walk-in kitchen pantry. The large master suite with ensuite bath has a large walk in closet. Plenty of natural light brightens your living spaces from the energy efficient windows. All bedrooms are generously sized. Style and comfort welcome you with brand new beautiful, premium style, extra thick, waterproof luxury vinyl plank flooring in all the living areas. Fresh new carpet in all bedrooms. Pretty ceramic tile in wet areas. ROOF 2024! A fresh coat of premium exterior paint has been done and seals the deal for years to come. MOVE IN READY! Come and see this lovely home in the well-maintained Lakes at Lucerne community today!

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

Listing Agent: Patty Wolfgang (813-389-5226)

Remarks: Welcome Home to this 3 bedroom/2 bath updated home. New granite counters in the kitchen, pass-through bar and both baths. Primary bath features a double vanity and walk-in shower, and secondary bath has large tile surround in the tub/shower combo. Kitchen is spacious and airy with a window sink overlooking the backyard. Freshly painted, new 6-panel doors, ceiling fans and lighting fixtures throughout. Laundry room is inside and has ample shelving for storage and pantry space. Tile throughout, so no carpet to maintain. Close to major throughfares, shopping and restaurants.

Listing is courtesy of: POWERS REAL ESTATE SOLUTIONS LLC (904-703-0905)

Listing Agent: Lynne Powers (904-703-0905)

Remarks: Under Construction. Located in the heart of Winter Haven, Willowbrook South puts you close to the area's Chain of Lakes, beautiful parks, and an array of dining and shopping. With top attractions and everyday conveniences just minutes away, your new home here keeps you connected to everything you love. Your new home at Willowbrook South places you right where you want to be. Let me Introduce you to the Archer II this 1328 Sqft. 3 Bedroom 2 Bath home is just to die for. This home provides Luxury Vinyl tile in all the wet areas, Living and Dining Rooms and Quartz Counter tops in the Kitchen and both Bathrooms. The Kitchen includes a Stove, Microwave, Dishwasher and Refrigerator, all Stainless Steel by Whirlpool and also includes a Washer/Dryer. The Archer II has an Open Floor plan that allows you to entertain guest even if they are in the living or dining room. Spacious bedrooms Owners Suite that can easily fit a King size bed. And on top of all that it also comes with our Home Smart System. Come by today!

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

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

Remarks: Under Construction. Located in the heart of Winter Haven, Willowbrook South puts you close to the area's Chain of Lakes, beautiful parks, and an array of dining and shopping. With top attractions and everyday conveniences just minutes away, your new home here keeps you connected to everything you love. Your new home at Willowbrook South places you right where you want to be. Let me Introduce you to the Archer II this 1328 Sqft. 3 Bedroom 2 Bath home is just to die for. This home provides Luxury Vinyl tile in all the wet areas, Living and Dining Rooms and Quartz Counter tops in the Kitchen and both Bathrooms. The Kitchen includes a Stove, Microwave, Dishwasher and Refrigerator, all Stainless Steel by Whirlpool and also includes a Washer/Dryer. The Archer II has an Open Floor plan that allows you to entertain guest even if they are in the living or dining room. 2 Spare Bedrooms and an Owners Suite that can easily fit a King size bed. And on top of all that it also comes with our Home Smart System. Come by today! *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: Under Construction. Located in the heart of Winter Haven, Willowbrook South puts you close to the area's Chain of Lakes, beautiful parks, and an array of dining and shopping. With top attractions and everyday conveniences just minutes away, your new home here keeps you connected to everything you love. Your new home at Willowbrook South places you right where you want to be. Now let me Introduce you to the Freeport II this 1498 sqft, 4 Bedroom 2 Bath home is just to die for. This home provides Luxury Vinyl tile in all the wet areas and Great room and Quartz Counter tops in the Kitchen and both Bathrooms. The Kitchen includes a Stove, Microwave, Dishwasher and Refrigerator, all Stainless Steel by Whirlpool and the laundry room also includes a Washer and Dryer. With 2 Spare Bedrooms in the Front one in the Middle and an Owners Suite in the Back. The Owners Suite can easily fit a King size bed and has a large Walk-in closet. It also includes a Home Smart System. Come by today! *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: New Price and $2500 Seller Credit!! Relocating to Florida? This pristine 5-bedroom, 3-bath home offers nearly 2,700 square feet of thoughtfully designed living space in the heart of Central Florida, providing the space, flexibility, and value many buyers from northern states and high-cost markets are seeking. Priced at $374,900—approximately $140 per square foot—this home delivers exceptional value compared to similar properties in California and many northern metro areas. The well-planned layout includes five true bedrooms, three full bathrooms, and a versatile flex space that could easily be converted into a sixth bedroom. This additional space makes the home ideal for growing families, multigenerational living, aging parents, young adults living at home, or a private home office or hobby room. A guest suite on the first floor adds even more functionality and convenience. The main living areas feature upgraded tile flooring, while the kitchen is finished with granite countertops and ample workspace for everyday living and entertaining. The home has been meticulously maintained and is in pristine, move-in-ready condition. Outdoors, enjoy added privacy with no rear neighbors, creating a peaceful and open backdrop rarely found in newer communities. Located just 5 minutes from downtown Winter Haven, residents enjoy easy access to historic charm, the Ritz Theatre, Saturday farmers markets, a beautiful public library, and a growing selection of high-end and locally owned dining options. A brand-new Publix grocery store is currently under construction within walking distance, adding everyday convenience and long-term appeal. The community features a very low HOA and no CDD fees, helping keep ownership costs manageable—an important advantage for relocating buyers. Ideally positioned just 5 minutes from Legoland Florida and approximately 30 minutes from Disney, the home offers access to Central Florida attractions while maintaining a comfortable residential setting. With generous square footage, flexible living spaces, privacy, and proximity to downtown amenities, this home is an outstanding opportunity for buyers ready to trade cold winters or high housing costs for a more flexible and comfortable Florida lifestyle.

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

Listing Agent: Veronica Bard (863-670-7526)

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: Under contract-accepting backup offers. Welcome to Lake Smart Estates - This Beautiful spacious home has had one owner and backs to a pond. This home has tons of upgrades for you to enjoy. The kitchen is spacious and features slab granite with under-mount sink, stainless steel appliances, pantry and breakfast bar. The kitchen opens to the living room with sliding glass door out to your screened in Lani. Also right off of the kitchen is a large formal dining room big enough for all of your get togethers. The first floor also features an office that could be used as the fourth bedroom. Travel upstairs To the open loft which is perfect for a study area, game or theater room... or hang out area for friends and guests. The master suite is large in every way featuring double sinks, soak tub, full tile walk in shower with glass door and large walk-in closet. All bedrooms in your new home are spacious and feature newer floors. The upstairs hall bath also features a double sink and the tub shower combo. Your new home sits right off of 544 with easy access to Highway 27 and I4, it is also located in a neighborhood that features a community pool and access to the chain of lakes. This home is priced to sell and won't last long call us today.

Listing is courtesy of: TRANSCONTINENTAL REALTY GROUP, (407-401-8522)

Listing Agent: Elizabeth Olivares (863-258-0113)

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)