Winter Haven Homes For Sale & Real Estate - 889 homes

Remarks: Completely remodeled and move-in ready, this stunning 2-bedroom, 2.5-bathroom condo in Casa Del Sol Village offers modern updates and a comfortable layout in the heart of Winter Haven. Every corner has been renovated, featuring new flooring, paint, lighting, kitchen appliances, doors, and beautifully updated bathrooms. The spacious living room and downstairs guest half-bath make entertaining a breeze, while both upstairs bedrooms boast private en-suite bathrooms for added convenience. Enjoy a low-maintenance lifestyle with an attached one-car garage, access to the community pool, and a location close to shops and restaurants—all amidst the beautiful landscapes and lakes that surround this lovely community.

Listing is courtesy of: WF REALTY CORP. (407-994-2900)

Listing Agent: Adriana Sanchez (321-947-4014)

Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Welcome home to easy Florida living in the beautiful, gated golf community of Cypresswood/Oak Grove! Tucked away on a quiet street, this 3-bedroom, 2-bath home offers the perfect blend of comfort, space, and relaxed lifestyle — plus major updates for peace of mind. From the moment you walk in, you’ll notice the soaring ceilings and natural light that make the home feel open and inviting. The layout flows effortlessly, with a formal dining space for holiday meals and special gatherings, along with a spacious eat-in kitchen featuring a breakfast bar that opens right into the family room — keeping everyone connected whether you’re entertaining or enjoying a cozy night in. The family room showcases tray ceilings and sliding glass doors leading to the enclosed patio — the perfect place for morning coffee, evening relaxation, or casual weekend get-togethers. It’s a wonderful extension of your living space and ideal for enjoying Florida’s year-round sunshine. The primary suite offers a peaceful retreat at the end of the day, while the additional bedrooms provide flexibility for guests, a home office, or hobbies. Even better, big-ticket items have already been taken care of — the roof was replaced in 2021, the water heater was replaced in 2023, home was freshly painted in 2022, and the A/C unit was replaced in 2018, giving you added confidence and long-term value. Living in Cypresswood means more than just owning a home — it’s about embracing the lifestyle. Residents enjoy a 24-hour manned gate, championship golf course, community pool, tennis courts, fitness center, and clubhouse. Spend your mornings on the course, afternoons by the pool, and evenings strolling through this beautifully maintained neighborhood. Conveniently located near shopping, dining, medical facilities, and major roadways, you’re close to everything while still enjoying the privacy and charm of a gated community. If you’ve been looking for comfort, community, smart updates, and a relaxed Florida lifestyle — this is it. Schedule your showing today!

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

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

Remarks: ***PRICE REDUCTION***Your turnkey oasis awaits! Welcome to a home that still feels brand new. This 2022-built gem in the peaceful Villa Mar community offers four spacious bedrooms and a bright, open floor plan designed for making memories. Whether you're hosting a dinner party in the modern kitchen or relaxing on your private, custom-screened lanai, every inch of this 1,680 sq. ft. home reflects quality and care. The interior boasts durable ceramic tile through the main living areas for a sleek, low-maintenance look, while the primary suite serves as a true retreat with elegant stone counters and dual vanities. Beyond the front door, the lifestyle is just as impressive. You’ll have access to fantastic community amenities like a resort-style pool, dog park, and playground, all while being located near top-rated schools. Best of all, you are just a short drive away from the world-class fun of Legoland, making this the perfect home base for weekend adventures. With a two-car garage and a generously sized laundry room, this home delivers the ultimate blend of style and convenience. Come see for yourself why this Villa Mar beauty is the perfect place to call home!

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

Listing Agent: Twanna Dewdney (863-207-1634)

Remarks: Welcome home to this well-priced, beautifully maintained 4-bedroom, 2-bath residence located in the highly sought-after gated Hidden Creek Community of Winter Haven. Perfectly positioned just minutes from the Polk Parkway, LEGOLAND Florida Resort, and conveniently situated between Lakeland and Winter Haven, this home offers both comfort and unbeatable accessibility. From the moment you arrive, you’ll appreciate the extra-long, widened driveway accented with elegant stone pavers leading to a spacious 3-car garage—ideal for guests, toys, or extra storage. Step inside to discover a bright, open living space filled with natural light, creating a warm and welcoming atmosphere perfect for everyday living and entertaining. The expansive great room features large windows and sliding glass doors overlooking the enormous, screened lanai (please note, only a screen enclosure no pool ever installed), seamlessly blending indoor and outdoor living. The open floor plan flows effortlessly into the kitchen, which is equipped with 42-inch cabinetry, granite countertops, stainless steel appliances, and an oversized island, making it the heart of the home. Ceiling fans and lighting throughout add a fresh, modern touch. The primary suite is a true retreat, showcasing a tray ceiling, generous walk-in closets, and a spa-like ensuite bath complete with dual vanities, a garden tub, walk-in shower, and private water closet—perfect for unwinding at the end of the day. One of the standout features of this home is the massive screened-in lanai, offering the ideal space for morning coffee, weekend barbecues, or relaxing evenings with family and friends. Bring your imagination for the outdoor living area that could be enhanced. Hidden Creek is located next to preserved land on the northwest side that brings peaceful living when in this community. Homes in this desirable gated community do not last long. Schedule your private showing today and experience the lifestyle Hidden Creek has to offer.

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

Listing Agent: Brandy Duncan (863-585-6849)

Remarks: Under contract-accepting backup offers. ON THE GOLF COURSE. GORGEOUS VIEWS AND SUNSETS! Well maintained 2 bed / 2 bath golf villa overlooks the 8th fairway and features split bedrooms, large living /dining combo, enclosed lanai with heat and air, partially covered courtyard, rear patio and carport parking space.

Listing is courtesy of: LOCKHART & ASSOCIATES INC (863-293-1234)

Listing Agent: Steven Smith, Pa (863-224-2297)

Remarks: MOVE IN CONDITION! Nestled on a beautifully landscaped and tree shaded lot this well maintained 2 bedroom 2 bathroom patio home features split bedrooms with ample closets, an expansive great room with space for living and dining areas, breakfast nook in the kitchen and an attached 2 car garage. Additional amenities include an oversized rear screened porch overlooking a picturesque greenspace with large shade-producing oak trees, Architectural Shingles, Pull-down Attic Stairs in the garage, Gas Water Heater and a 2-Car Garage. Cypresswood Golf & Country Club offers a variety of amenities, including an 18-hole golf course, clubhouse with pro shop and lounge, Jr Olympic swimming pool and a soon-to-be-completed tennis, pickleball and recreation area. Located in close proximity to HWY 27 affords easy access to I-4 and within 1.5 hours of either coast. This ideal location is just a mile down the road from a brand new Publix set to open shortly as well as being conveniently close to shopping, restaurants, and Legoland.

Listing is courtesy of: LOCKHART & ASSOCIATES INC (863-293-1234)

Listing Agent: Steven Smith, Pa (863-224-2297)

Remarks: Welcome to a home that checks the boxes and adds a little personality along the way! Located at 3396 Ave U NW in Winter Haven, this beautifully remodeled 4-bedroom, 2-bath residence is move-in ready and waiting for its next chapter. Step inside and you’ll immediately notice the fresh updates throughout—because let’s be honest, no one wants a “project” unless it’s on a vision board. This home features a brand-new roof, HVAC system, and windows, water heater, granite countertops, stainless steel appliances, cabinets + more, giving you peace of mind and energy efficiency from day one. Translation? Less worrying, more living. The layout offers flexibility for a variety of living arrangements, including a separate entrance that opens the door to endless possibilities—whether you’re thinking guest suite, private office, creative studio, or simply a little extra breathing room. You decide how it fits your lifestyle. Outside of the home, the location delivers convenience and entertainment all in one. You’re just minutes from LEGOLAND, perfect for fun-filled weekends or hosting out-of-town guests. Nearby, you’ll find a variety of dining options, shopping centers, and everyday essentials to make life easier. Access to quality healthcare is close by as well, including Winter Haven Hospital, giving added peace of mind when it matters most. Whether you're looking for space to grow, room to host, or simply a place that feels like home the moment you walk in—this one delivers. Schedule your private showing today and come see why this property might just be “the one” you didn’t know you were waiting for.

Listing is courtesy of: OPULENT REALTY INTERNATIONAL (863-323-7778)

Listing Agent: Alicia Self (863-450-8394)

Remarks: MOVE-IN READY! Step inside this stunning one-story Castaway home feel right at home. As you enter through the front door, a welcoming foyer sets the tone for the open and inviting layout. Two spacious bedrooms are tucked at the front of the home and share a beautifully designed full bathroom, perfect for family or guests. A third bedroom with its own private bath offers comfort and privacy, ideal for visitors or a home office setup. Continue down the hallway and the home opens up into a wide, light-filled living area where the kitchen, dining, and family room seamlessly connect. The kitchen features sleek gray cabinets, quartz countertops, and a large island that overlooks the gathering spaces, making it the heart of the home—perfect for cooking, dining, and entertaining all at once. At the back of the home, the private primary suite provides a peaceful retreat with a spacious bathroom featuring double vanities, a walk-in shower, and a generous walk-in closet. Step outside through the sliding doors to a covered lanai, where you can relax and enjoy Florida’s sunshine year-round. Situated on a desirable corner homesite in Willowbrook North, this beautifully designed home offers modern finishes, an open concept layout, and a lifestyle made for comfort and connection.

Listing is courtesy of: DRB GROUP REALTY, LLC (407-270-2747)

Listing Agent: Adam Schott (407-270-2747)

Remarks: MOVE-IN READY! Beautiful 2 Level, Coastal elevation, 2 Car Garage Home with Open Concept Living and 3 Bedrooms! The inviting front porch opens to a gracious foyer that leads you to the open main living space. The family room is open to the dining area and adjacent kitchen. The primary suite boasts an ensuite bathroom with dual sink vanity, shower, private water closet, and large walk-in closet. The second level offers a spacious loft and 2 secondary bedrooms each with walk-in closets and a full bathroom.

Listing is courtesy of: DRB GROUP REALTY, LLC (407-270-2747)

Listing Agent: Adam Schott (407-270-2747)

Remarks: One or more photo(s) has been virtually staged. Step into comfort, space, and opportunity in this move-in ready 4-bedroom, 2.5-bath home located in the established Forest Ridge community of Winter Haven—with no CDD. From the moment you arrive, the inviting covered front porch and mature landscaping set the tone for what’s inside. The thoughtfully designed layout offers the perfect balance of everyday comfort and flexible living. The main level features an open kitchen and living area, a versatile bonus room near the entry—ideal for a home office, playroom, or creative space—and a convenient half bath for guests. At the center of the home, the open-concept kitchen is built for connection, featuring a center island, black and stainless steel appliances, and seamless flow into the dining and living areas—perfect for entertaining or simply enjoying day-to-day life. Recently upgraded dishwasher and garbage disposal. Durable tile flooring and recently upgraded carpet throughout all the main living spaces and upstairs bedrooms adds a clean, modern feel and abundant natural light creates a bright, welcoming atmosphere. Upstairs, you’ll find all four bedrooms, including a spacious primary suite designed for relaxation, along with two full bathrooms and a conveniently located laundry area equipped with a smart washer and dryer. Each space is designed with comfort and functionality in mind. Step outside to a generously sized backyard ready for your vision—whether it’s a future pool, outdoor kitchen, garden, or play space, the possibilities are endless. Set within the peaceful surroundings of Forest Ridge, you’ll enjoy quiet streets while being just minutes from Highway 27 and a short drive to I-4, giving you easy access to shopping, dining, schools, and everything Central Florida has to offer. This home checks all the boxes—space, flexibility, location, and value. Schedule your private showing today and see the potential for yourself!

Listing is courtesy of: KELLER WILLIAMS SUBURBAN TAMPA (813-684-9500)

Listing Agent: Daniel Henzler (813-293-3603)

Remarks: LOCATION, LOCATION! 17 minutes from Cypress Gardens! 8.2 miles away from LEGOLAND! 6 mins from Winter Haven Airport! 11 miles from I-4 east Ramp! 5 mins from Publix and many local restaurants, parks, lakeside views and much more. Located on a quiet road, the newly built 1550 sq ft modern home includes continuous luxury vinyl flooring on both floors, luxury quartz countertops with matching backsplash, two tone kitchen cabinets, neutral paint throughout , high ceilings. Ceiling fans throughout, with glass front door accent. Two tone exterior with ambient lighting and black and gold accents throughout the home. Kitchen includes Calacatta quartz countertop on 6 ft island and backsplash with off white uppers and oak lowers, half bathroom downstairs includes a black and gold designer vanity, upstairs guest bathroom has a pop of black and white arched mosaic detail in the shower included in the vanity mirror as well as the vanity. Master bathroom includes a double fluted wood vanity with drawers and shelves, LED light up mirror and large format black and white Calacatta porcelain tile in entire shower. Chic exterior with a pop of sage green on the front door. Chrome and brush nickel finishings, matching interior lower cabinets and all bathroom vanities are with a pop of color modern finishing included throughout such as LED lights, curved mirrors and matching bathroom tiles.

Listing is courtesy of: UNITED REAL ESTATE PREFERRED (407-243-8840)

Listing Agent: Lajuan Chambers (321-477-8805)

Remarks: Welcome to easy Florida lake view living in this beautifully updated 2-bedroom, 2-bath home located in a friendly 55+ no pet community on the shores of sparkling Lake Henry in sunny Winter Haven. Offering 1,456 square feet of comfortable living space, this well-loved home has been thoughtfully improved from top to bottom and is ready for its next owner. Step inside to find a bright and inviting interior featuring all new flooring, updated lighting, and ceiling fans throughout. The completely renovated kitchen is a standout, showcasing soft-close cabinetry with convenient pull-out drawers, providing both style and functionality. Both bathrooms have been tastefully remodeled, offering a fresh, modern feel. Major updates include a new roof, new AC system, new dual-pane double tilt-in windows, new skylights, and a new electrical panel—giving peace of mind for years to come. The guest bedroom comes fully furnished, making it perfect for visiting family or friends. Enjoy year-round relaxation in the Florida room, complete with its own heating and cooling, or step outside to the private backyard patio surrounded by beautiful landscaping and a full irrigation system. Enjoy lake view from both front and rear of this beautiful home! This home offers the perfect blend of comfort, convenience, and low-maintenance living in a welcoming lakefront community. Call today to schedule your private tour!

Listing is courtesy of: COLDWELL BANKER REALTY (863-687-2233)

Listing Agent: Laura Villardi (317-402-6277)

Remarks: Owner motivated and ready to negotiate — WOW! This BEAUTIFUL 1361SF 2BR/2BA FIRST-FLOOR condo in Orchid Springs offers stunning lagoon/pond views! Located in the 55+ Granada Building, where at least one occupant must be 55+. IMMEDIATELY AVAILABLE and MOVE-IN READY! Step into an open, airy floor plan with tile throughout, creating a bright and spacious feel. The dining area, living room, and bonus room flow seamlessly together, all overlooking the tranquil lagoon. As an end unit, the living room and bedrooms enjoy extra windows with peaceful courtyard views. The primary bedroom features a walk-in closet plus an additional hallway closet, providing excellent storage. Both bathrooms are well-appointed, with one offering a custom vanity and a tub/shower combo. Additional highlights include assigned parking directly in front of the unit. Perfect for year-round living or a seasonal retreat in a serene, well-maintained community.

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Sharon Gastelbondo (863-800-4655)

Remarks: Owner motivated and ready to negotiate — WOW! This BEAUTIFUL 931 SF 1BR/1BA FIRST-FLOOR condo in Orchid Springs offers stunning lagoon views! Located in the 55+ Granada Building, where at least one occupant must be 55+. IMMEDIATELY AVAILABLE and MOVE-IN READY! Step into an open, airy floor plan with tile throughout, creating a bright and spacious feel. The dining area, living room, and bonus room flow seamlessly together, all overlooking the tranquil lagoon. As an end unit, the living room and bedroom enjoy extra windows with peaceful courtyard views. The bedroom features a walk-in closet plus an additional hallway closet, providing excellent storage. The bathroom includes a custom vanity and a tub/shower combo. A washer and dryer are included, offering added convenience. Additional highlights include assigned parking directly in front of the unit. Perfect for year-round living or a seasonal retreat in a serene, well-maintained community.

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Sharon Gastelbondo (863-800-4655)

Remarks: Conveniently located in the heart of Winter Haven, this 5 Bedroom 3 Bathroom home with two Flex Rooms is move in ready and close to everything loved, including: Easy commuting, Grocery Stores, Shopping, Dining, Chain of Lakes, Boat Ramps, Scenic Walking Trails, Legoland Florida Resort, and Beaches just an hour and a half away! Step outside to your private oasis featuring a Caged Saltwater Pool with a Safety Alarm System, perfect for peace of mind. The spacious Gazebo adds a relaxing shaded retreat for outdoor dining, lounging, or entertaining. Unique Bonus Room with a Sound Proofing wall, ideal for Recording Studios, Podcasters, Musicians, Content Creators or any Work from home professionals needing their quiet space. This home shows like new with Fresh interior paint, New Luxury Laminate flooring, Carrara porcelain tile for a sleek modern finish, Bright open concept living spaces and a Spacious Kitchen perfect for gatherings. With this home offering flexibility for Large Families, Multi Generational living or hosting guests comfortably, it is a must see! Schedule your showing soon!

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

Listing Agent: Andrea Friedmann (863-661-6535)

Remarks: Under contract-accepting backup offers. Central Florida Lakefront home for sale now with a HUGE PRICE IMPROVEMENT! Move in ready 4BR/2BA with Office on Private-Access Lake Bess complete with a Slalom Ski Course! Enjoy direct connection to Lake Ruby! You access to TWO beautiful lakes featuring white sandy bottoms, tranquil waters. These lakes are ideal for water sports (private access) and serene lakeside living. The open layout and large glass sliding doors create a seamless connection between Indoor Elegance and Outdoor Beauty, making every arrival feel like a moment of escape! Enjoy Updated Features including ROOF 2019, NEW EPOXY GARAGE FLOORING, Stunning Views, Resurfaced Pool, Covered Lanai for Outdoor Living, NEWLY PAINTED Dock with Boat Lift, Large Windows for Natural Light, Formal Dining Room, Lake View Breakfast Nook and Inside Laundry Room with Utility Sink and Cabinets. The Kitchen offers Lake Views, Granite and a Full Appliance Package, while the Spacious Primary Suite includes a Walk-In Closet and a Luxurious En-Suite Bathroom. This lakefront Split Floor Design not only enhances privacy for you and guests but also creates a more spacious, balanced flow throughout the home, ideal for both everyday living and entertaining. Enjoy lush landscaping with an eco-friendly irrigation system that draws from the lake. Come see why Ruby Lake with barely over 200 homes is ideal with Manicured landscaping, Underground Utilities and quiet streets for evening or morning strolls. Located less then two miles from a Golf Course, less than five to Legoland, shopping, dining, and medical facilities plus easy access to both Tampa and Orlando. Florida's Beautiful Gulf and Atlantic Beaches less then two hours away in either direction! Cruise enthusiasts, Port Canaveral is only 70 miles away! Whether you're seeking adventure on the water or peaceful evenings by the dock, Ruby Lake offers a lifestyle that’s both vibrant and serene!

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

Listing Agent: Andrea Friedmann (863-661-6535)

Remarks: Unique and spacious property offering flexibility and great outdoor living! This home features multiple living areas with beautiful exposed wood beam ceilings, updated flooring throughout, and plenty of natural light. The layout offers generously sized bedrooms and a functional kitchen with ample cabinetry and workspace, perfect for everyday living and entertaining. One of the standout features of the property is the separate guest house structure located in the backyard, providing great potential for extended family, guests, a home office, or additional living space. The backyard also features a pool and a large yard, creating an ideal setting for outdoor gatherings and relaxation. Conveniently located near shopping, dining, schools, and major roadways in Winter Haven.

Listing is courtesy of: LIFESTYLE INTERNATIONAL REALTY (305-809-8085)

Listing Agent: Talitha Lastre (305-772-8849)

Remarks: The seller is OFFERING UP TO $14,000 toward a NEW ROOF or may apply this contribution toward the BUYER'S CLOSING COSTS, providing added flexibility and value. This spacious 4-bedroom, 3-bath ranch-style home offers an impressive amount of living space (2,178 sqft) filled with natural light and designed for comfort and flexibility. The many windows throughout the home create a bright, welcoming atmosphere, while multiple living areas provide room to spread out and enjoy. The remodeled kitchen features a refrigerator, dishwasher, and range, along with a convenient breakfast bar and adjacent dining area—perfect for everyday living and entertaining. A formal living room greets you at the front entry, and the oversized family room offers exceptional gathering space, complete with a built-in desk and direct access to the screened lanai. The generous primary suite includes a walk-in closet, garden tub, separate shower, and an additional wall A/C unit for added comfort. A desirable mini–master suite with its own private bath provides ideal space for guests, extended family, or a private home office. Built-in cabinetry throughout the home adds both character and abundant storage. Situated on a large corner lot, the expansive yard offers endless possibilities for outdoor living, recreation, or future enhancements. The chain-link fenced backyard provides security and functionality while maintaining an open feel. With no HOA restrictions, you’ll enjoy the freedom to personalize the property to suit your needs. Combining space, natural light, a sizable yard, and the advantage of no HOA, this property delivers comfort, flexibility, and room to grow.

Listing is courtesy of: CENTURY 21 MYERS REALTY LAKE WALES (863-676-4448)

Listing Agent: Michelle Heath (863-528-3123)

Remarks: Cozy 2 bedroom 2 bath home with great view of Lake Howard off the master bedroom and patio. Turn around and look out of the front door with a beautiful view of the pool and patio areas. Rood is new this year with all damage from last year's storm repaired. This home is in move-in condition.

Listing is courtesy of: CHOICE PROPERTIES OF CENT FL (863-299-6710)

Listing Agent: Jane Tyl (863-224-1779)

Remarks: Welcome to a move-in ready villa in the desirable 55+ Oakview community of Winter Haven—now strategically repositioned to reflect today’s market and create immediate opportunity. This well-maintained 2-bedroom, 2-bath home offers 1,220 sq ft of comfortable living with a functional open layout, spacious bedrooms with walk-in closets, and a screened lanai designed for relaxed Florida mornings and evenings. Major updates are already done for you, including a NEW ROOF (2024) and HVAC (2019), giving buyers confidence where it matters most. The kitchen has been refreshed with brand-new appliances, making this a truly easy transition with no extra projects needed. A standout feature is the garage screen system, allowing you to enjoy fresh air and added flexibility during the day—an underrated benefit for Florida living. The HOA covers lawn care and exterior maintenance, supporting a low-maintenance, lock-and-leave lifestyle many buyers are actively seeking. Now repositioned to align with current market conditions—creating one of the most compelling opportunities in Oakview today. With recent activity in the community, buyers are moving quickly when the value makes sense—schedule your showing today.

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Vanessa Aybar Badillo (352-557-1682)