Homes For Sale in Winter Haven 33881 - 271 homes

Remarks: Welcome to this fully upgraded 4-bedroom, 2.5 bath Winter Haven home! This home offers modern living, featuring new flooring, appliances, new windows with pull-out panes for easy access and cleaning along with new Plantation Shutters on all windows! You will also enjoy the stylish bathroom/kitchen renovations featuring in the kitchen beautiful backsplash and new pantry door, new tile in guest bath and new shower in primary bathroom! Centrally located near Legoland, shopping, and all your medical facilities, the property includes a new fenced back yard and new storage shed, HOA/City approved. Sellers are highly motivated!

Listing is courtesy of: STACEY TOWNS REALTY LLC (863-422-1585)

Listing Agent: Cathy Stripling (863-422-1585)

Remarks: One or more photo(s) has been virtually staged. Welcome to this stunning Winston floorplan, located in the highly sought-after community of Willowbrook near a beautiful golf course in Winter Haven, FL. This spacious 5-bedroom, 3-bath home offers 2,531 square feet of living space and provides excellent curb appeal in its elevation. Inside, you'll find gorgeous White 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: Cindy Sapp (352-516-2843)

Remarks: HUGE PRICE DROP! Completely renovated home with new pool on Cannon Lake! Welcome to your dream lakeside retreat on a sprawling lot with 120 feet of pristine lakefront on Lake Cannon. This completely renovated three-bedroom, two-bathroom home boasts an open floor plan with high ceilings and a desirable split-bedroom layout. The stunning kitchen features granite countertops, a counter-height breakfast bar, and brand-new Samsung bespoke appliances, including an induction stove, perfect for culinary enthusiasts. The expansive primary suite offers a luxurious en suite bath with a large shower equipped with multiple showerheads, including a rain showerhead, and sliding glass doors that lead to an impressive outdoor entertaining space. The screened-in patio, perfect for hosting gatherings, overlooks the brand-new saltwater, heated pool and spa, completed in 2025, creating an idyllic setting for relaxation and fun. Additionally, the home features a new roof and new windows, ensuring peace of mind for years to come. Enjoy unobstructed views of the lake from your large outdoor area, ideal for summer barbecues or evening stargazing. Conveniently located near shopping, restaurants, and entertainment, this home truly offers the best of lakeside living on the chain of lakes.

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. This 3 bedroom, 2 bathroom home is located in Idylwild Heights a charming residential subdivision nestled in Winter Haven, Florida. Winter Haven is a picturesque city celebrated for its chain of lakes and friendly community atmosphere. Known for its welcoming ambiance and established neighborhood feel, Idylwild Heights offers residents an appealing blend of suburban tranquility and convenient urban access.

Listing is courtesy of: CENTURY 21 WOLF'S CROSSING REALTY (407-449-0000)

Listing Agent: Lucy Martinez (863-521-4156)

Remarks: Welcome to 6617 Westchester Dr NE in Winter Haven, located in the highly desirable 55+ no pet community of Lake 'n Golf Estates. This spacious and well maintained home has been lovingly owned by the same family since 1992 and offers comfort, convenience, and a true Florida lifestyle. Inside, you’ll find a bright and inviting layout with generous living spaces, engineered wood flooring in the main living areas and bedrooms, and porcelain tiles in the kitchen, bathrooms, and hallway. The home also features an inside laundry room for added ease. It will be sold mostly furnished, making it a perfect move in ready option for seasonal or full time living. A standout feature is the enclosed front Florida room, complete with its own mini/split system for heating and cooling, along with updated windows, blinds, porcelain flooring, a ceiling fan, and a hide-a-bed, creating a comfortable and versatile bonus space year round. This home has been thoughtfully updated over time, including a new roof (2023), updated heat pump and ductwork, a membrane roof over the sunroom and new siding (2025). Additional improvements include updated windows and doors, enhanced plumbing throughout (including replacement of gray piping, water heater, fixtures, and disposal) and upgraded appliances such as a new stove (2025) and microwave (2024). Outside, you’ll appreciate the large carport, a beautifully finished driveway, and additional space for golf cart parking, along with a cement golf cart path for added convenience. With NO REAR neighbors, the property offers a private and peaceful setting. Additional included items such as select furnishings, a leather recliner, beds, TVs, ceiling fans, blinds, and an outside antenna add even more value and convenience. Residents of Lake 'n Golf Estates enjoy a vibrant and active lifestyle with access to lake Henry, a clubhouse, pool, shuffleboard courts, and a variety of social activities. Conveniently located near shopping, dining, and everyday amenities, this community offers both relaxation and accessibility. Don’t miss your opportunity to own a beautifully updated and spacious home in one of Winter Haven’s most welcoming 55+ communities, schedule your private showing today!

Listing is courtesy of: RE/MAX HERITAGE PROFESSIONALS (863-256-2188)

Listing Agent: Patricia De Graaff, Llc (863-307-0061)

Remarks: One or more photo(s) has been virtually staged. Welcome to this stunning Dream Finders Poinciana floorplan, located in the highly sought-after community of Willowbrook near a beautiful golf course in Winter Haven, FL. This spacious 4-bedroom, 3-bath home offers 2,110 square feet of living space, and providing excellent curb appeal in it's elevation. Inside, you'll find gorgeous white 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: Your new Florida home is waiting for you. This home has many updates and improvements. The shingled roof was installed in December 2024 and the HVAC is 6 years old. A new vapor barrier has been installed. There are new plywood subfloors and luxury vinyl plank in the living room, dining room, hall, and both bathrooms. There is no carpet in this home. The kitchen is perfect for preparing all those special meals. The living room is open and spacious. The front Florida room is perfect for your morning coffee. Lake n Golf Estates, a 55+ community, offers many amenities including a pool, shuffleboard, and clubhouse. Join in the activities or just sit back and enjoy the peaceful community.

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

Listing Agent: Kathy Devor (573-450-1679)

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: Another Great Listing brought to you by Paul Jacques, P.A. EveryThing Real Estate. Gated Community, Like New. Open floor plan. minutes from downtown Winter Haven. Low HOA, you’ll enjoy neighborhood security and amenities without the extra cost. Commuters will love the quick access to Hwy 27, providing an easy drive to area beaches, Orlando’s theme parks, and more. Price To Sell.

Listing is courtesy of: XCELLENCE REALTY INC. (866-595-6025)

Listing Agent: Paul Jacques (561-441-9695)