Winter Haven Homes For Sale & Real Estate - 803 homes

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: Seller motivated. Welcome to your home in Winter Haven—just minutes from Legoland, shopping, medical facilities, and Highway 27 for easy commuting! Originally a 3-bedroom, 2-bath layout, this home has been converted into a spacious 5-bedroom, 2-bath residence, offering incredible versatility for growing families, multigenerational living, or those needing extra space for a home office or hobby rooms. It will need some TLC due to tenant being in property. With five true bedrooms, everyone in the family can have their own retreat while still enjoying generous shared living spaces. Outside, you’ll find a property ideally situated for convenience—whether you’re heading to Legoland for weekend fun, accessing everyday amenities just minutes away, or commuting via Highway 27. This home offers the perfect blend of location, and space in one of Winter Haven’s most desirable areas.

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

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

Remarks: Discover unparalleled versatility and breathtaking lakefront living with this beautifully remodeled/converted dual-unit home on the shores of Lake Jessie in Winter Haven, Florida. Although zoned single-family residential, this property has been thoughtfully converted into two stunning living spaces—ideal for multigenerational families, in-law accommodations, or dual-family living side-by-side. Unit 1- 2,900 SF welcomes you with a fully renovated two-story layout featuring 4 bedrooms and 3 full bathrooms and 1 half bath. Enjoy gorgeous lakefront views from multiple vantage points and modern finishes throughout, creating the perfect blend of comfort and style. Unit 2- 2,800 SF, mirrors the same level of craftsmanship, two story offering 5 bedrooms and 3 full bathrooms. This spacious unit is also fully remodeled and showcases sweeping views of Lake Jessie, making every day feel like a retreat. Two car garage with additional storage room off the front of the garage. Your backyard becomes a true private oasis—complete with a fire pit, outdoor grill area with a pergola, and a covered boat dock equipped with a boat lift, water, and electric. Watch sea planes take off and land daily from Brown’s Sea Plane Base right from your own waterfront sanctuary. Whether you’re seeking a unique multigenerational setup, an expansive home for a large family, or the ultimate lakeside lifestyle, this exceptional property delivers it all. Don’t miss the opportunity to own this one-of-a-kind lakefront retreat in beautiful Winter Haven, Florida.

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: Under contract-accepting backup offers. Welcome to 20 N Lake Idylwild Dr—an incredible 6 bed | 4 bath multigenerational lakefront estate on a private .98-acre homesite. This two-story pool home features two fireplaces, a two-story dock, and a second-story deck overlooking the water. Located on Winter Haven’s legendary Chain of 24 Lakes, enjoy true Florida waterfront living with the freedom to boat to LEGOLAND® and local waterfront bars and restaurants. Start your mornings with sunrise views, host unforgettable gatherings, and embrace year-round outdoor living. With nearly 60’ of lake frontage, this property is a standout opportunity for full-time living, a second home, or an attractive Airbnb/short-term rental investment in one of Central Florida’s most sought-after lake communities. Just minutes from Winter Haven Municipal Airport for easy travel access. Schedule your private showing today—this one is a must-see.

Listing is courtesy of: AUSTIN DEANE REALTY INC (863-698-2329)

Listing Agent: Victoria King (813-853-8548)

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! Welcome to the Flagler floor plan, where timeless charm meets modern luxury. The home’s traditional elevation with a welcoming front porch sets the tone for elegance and comfort. Inside, a versatile flex space off the entry offers the perfect spot for a home office or cozy reading nook. The heart of the home features a chef-inspired kitchen with an oversized quartz island, sleek cabinetry, and abundant counter space, all seamlessly flowing into the dining and living areas. Natural light pours in through sliding glass doors, opening to the backyard and creating the ideal setting for entertaining or everyday living. Two spacious bedrooms, a full bath, and a conveniently placed laundry room are located just off the kitchen, designed with functionality and ease in mind. At the back of the home, the private primary suite feels like a true retreat with elegant tray ceilings, a generous walk-in closet, and a spa-style bathroom with dual vanities and designer finishes. With its open-concept design, luxurious finishes, and thoughtful split-bedroom layout, the Flagler offers the perfect balance of style, comfort, and sophistication an exceptional place to call home.

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

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

Remarks: MOVE-IN READY! Welcome to your dream home in the sought-after Willowbrook North community! This stunning Ranch-style, one-story residence offers effortless living with 3 spacious bedrooms, 2 full bathrooms, and a versatile flex space—perfect for a home office, playroom, or additional living area. You'll fall in love with the modern open-concept layout, featuring quartz countertops throughout, soft-close cabinets and drawers, and smart home features designed for comfort and convenience. Enjoy peaceful mornings and relaxing evenings with serene pond views right outside your front door. Built with quality and style in mind, this home is the perfect blend of elegance and functionality—ready for you to move in and make it your own. Don't miss this opportunity to own a beautifully crafted home in a growing, vibrant community!

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

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

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: Welcome to this beautifully renovated lakefront retreat on Thomas Lake in Winter Haven! This stunning two-story home combines modern upgrades with warm character and breathtaking water views. Step inside to tall vaulted ceilings creating an open, airy layout filled with natural light. The home features all-new flooring throughout and a completely updated kitchen showcasing stainless steel appliances, quartz countertops, brand-new cabinetry, and closet pantry – providing plenty of storage and room to cook or entertain. A cozy fireplace with a raised hearth and wood accents adds charm and a welcoming focal point to the living space. Both bedrooms are a peaceful retreat with beautifully updated bathrooms, one featuring a large walk-in closet. The loft could also be used as a 3rd bedroom or flex space! The home also includes a new electric water heater and newer A/C (2022) for added efficiency and peace of mind. Outside, you’ll find a newer roof (2022), fresh exterior paint, an attached 1-car garage with driveway, and plenty of space to enjoy the outdoors. Relax or entertain on the large rear patio, or unwind on the private, enclosed back porches on both floors, each offering gorgeous, tranquil lake views. This move-in-ready lakefront gem blends modern updates, comfort and scenic surroundings, making it a rare opportunity you won’t want to miss!

Listing is courtesy of: PORCHLIGHT HOMES LLC (863-529-3369)

Listing Agent: Angie Reynolds (863-838-1090)

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: Priced to Sell! -A fantastic opportunity awaits the buyer looking for a quiet neighborhood with plenty of outdoor space and wide-open views from the back of the property. Welcome home to this spacious 3-bedroom, 2-bathroom double-wide mobile home, designed for comfortable living and maximum storage. The functional floor plan includes two screened-in porches, one at the front and one at the back, offering a seamless transition between indoor and outdoor living. A practical carport protects your vehicle from the elements, while the detached one-car garage, complete with extra storage, is perfect for a workshop or housing your toys. This double-wide mobile home sits on just over a quarter acre and offers a generous footprint, ready for your personal touch. With a little vision, you can transform this property into your dream home and build instant equity.

Listing is courtesy of: JULIE CLARK REAL ESTATE (863-944-2772)

Listing Agent: Janet Harrison (863-712-0606)

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: Price Improved! Seller is motivated... Welcome to 740 Squires Grove Dr. This beautiful 5 bedroom, 3 bath residence offers the space you've looking for, filled with natural light and and large fenced backyard ideal for gatherings, pets or relaxing outdoors. Well located near shopping, dining, hospitals, major highways, and just minutes from LEGOLAND. Book your showing today!

Listing is courtesy of: NORTHGROUP REAL ESTATE, INC (561-222-1850)

Listing Agent: Lulis Batista (407-969-2098)

Remarks: Price Improvement! Motivated seller brings added opportunity on this inviting four-bedroom, two-bathroom single family home in Winter Haven. Featuring a desirable split floor plan, this home offers privacy comfort, space, and functionality for the primary suite while maintaining an easy, natural flow throughout the main living areas perfect for everyday living and entertaining. The spacious primary suite serves as a relaxing retreat, featuring, a walk-in closet, a soaker tub, and a separate shower. Generously sized secondary bedrooms present flexibility for guests, a home office, or future needs. Enjoy warm and welcoming living spaces that lead to a screened patio, ideal for morning coffee or evening gatherings, all overlooking a fenced backyard that provides privacy and room to enjoy the outdoors. A brand-new roof installed in 2025 adds peace of mind and long-term value. Move-in ready and competitively price. This home is a fantastic opportunity for buyers. Looking for space, comfort, and a great value This home is ready for its next owners. Schedule your showing today and bring your offers. YOUR NEW HOME AWAITS. DOWN PAYMENT ASSISTANCE IS AVAILABLE TO QUALIFIED BUYER(S)

Listing is courtesy of: AUDITH POLEON REALTY (863-709-5643)

Listing Agent: Audith Poleon (863-709-5643)