Winter Haven Homes For Sale & Real Estate - 1006 homes

Remarks: Under contract-accepting backup offers. POOL HOME ON AN OVERSIZED CORNER LOT WITH A SCREENED LANAI, DETACHED SHE SHED/MAN CAVE, AND A FULLY FENCED BACKYARD! Tucked beneath mature shade trees in Winter Haven's established High Point community, this well-maintained home offers the space, flexibility, and outdoor living opportunities that many buyers have been searching for. From the inviting covered front porch to the multiple outdoor gathering areas, every part of this property is designed to be enjoyed. Step inside to a bright and welcoming interior where natural light fills the living spaces and creates a comfortable atmosphere throughout. The living room serves as the heart of the home and flows effortlessly into the dining area and kitchen, creating a layout that feels connected and functional for both everyday living and entertaining. The kitchen features ample cabinetry, generous countertop space, stainless steel appliances, breakfast bar seating, and easy access to the home's outdoor living areas. The home offers three comfortable bedrooms, each providing flexibility for family, guests, hobbies, or a home office. The centrally located bathroom features a dual-sink vanity with ample storage and countertop space. An indoor laundry room adds everyday convenience, and an additional flexible room currently used for storage offers opportunities for future use based on your needs. One of the home's standout features is the expansive screened lanai stretching across the rear of the property. This impressive outdoor living space creates the perfect setting for morning coffee, outdoor dining, game days, or relaxing evenings while enjoying Florida's beautiful weather. Beyond the lanai, the fully fenced backyard offers multiple areas to gather, entertain, and unwind. The above-ground pool creates a refreshing backyard retreat surrounded by mature landscaping and outdoor living spaces. A detached 12x20 she shed/man cave provides exceptional flexibility and can easily be utilized as a hobby room, creative studio, fitness space, game room, workshop, or private retreat. The property also features two separate carports, providing covered parking and additional space for vehicles, equipment, projects, and everyday convenience. The oversized corner lot offers additional outdoor space and versatility rarely found in many homes of this size. Whether you're hosting family gatherings, working on hobbies, gardening, relaxing by the pool, or simply enjoying the shade of the mature trees, this property provides room to live, work, and play. Conveniently located near shopping, dining, parks, schools, medical facilities, Winter Haven's renowned Chain of Lakes, Legoland Florida Resort, downtown Winter Haven, and major roadways connecting throughout Central Florida, this home offers convenient access to everyday essentials and local recreation. If you've been searching for a property that offers more than just a house—a place with room to gather, relax, create, and enjoy the Florida lifestyle—this home is ready to welcome its next owner.

Listing is courtesy of: KELLER WILLIAMS CLASSIC (407-292-5400)

Listing Agent: Simi Lakhani (407-408-7393)

Remarks: New - New - New! This 3 bedroom 2 bath features a beautiful lake view and has been completely remodeled. Updates include a new HVAC system, new metal roof, new kitchen with granite counters, new bathrooms, new flooring, and new septic system. No HOA means you can store your boat. Can be purchased together with 73 High Street to make a family compound or have an income producing property. (MLS P4937859)

Listing is courtesy of: ALLSTATE REALTY SERVICES (863-965-0207)

Listing Agent: Dwight Head (863-965-0207)

Remarks: Under contract-accepting backup offers. Improved Price!! All new window in the building...Price improvement...Seller ready to sell! Beautifully maintained 55+ condominium located in Lake Ridge Winter Haven. This is a gated community offering a tranquil living space. Conveniently located near hospitals, restaurants, shopping, entertainment and so much more. This home offers everything you need to live a true Floridian lifestyle. Amenities include heated pool ALL year around, tennis court, shuffleboard, pickle ball, car washing area, outdoor grills, community room, and covered guest parking for your family to enjoy when they visit. The community offers community events so boredom is not an option. So much opportunity to socialize and create amazing memories. This specific unit offers a relaxing airy and bright Florida room to sit back and enjoy your coffee. Association will be putting in new windows and fresh exterior paint this summer. The assessment is PAID in FULL so you can affordable live in style. Monthly association covers water, sewer, trash, fiber optics cable, internet, prime HD package, condo reserves, and maintenance. This is truly a hidden gem waiting for its new owner! Whether you are looking for a winter retreat or a forever home, this condominium offers you your own piece of paradise. Check it out before its gone! Schedule your showing TODAY!

Listing is courtesy of: CENTURY 21 MYERS REALTY (863-875-5656)

Listing Agent: Brenda Brooks (863-370-9667)

Remarks: Welcome to this beautifully maintained newer home in the desirable Squires Grove community of Winter Haven! Built in 2022, this spacious 3-bedroom, 2-bath residence offers an open-concept layout with a bright living and dining area—perfect for entertaining. The modern kitchen features ample cabinetry, sleek appliances, and a large island overlooking the main living space. A split-bedroom floor plan provides privacy, with a generous primary suite including a walk-in closet and en-suite bath. Enjoy outdoor living in the private backyard with room to relax or host gatherings. Additional highlights include a 2-car garage, indoor laundry, and energy-efficient construction. Conveniently located near shopping, dining, schools, and major roadways, this home offers comfort, style, and convenience in one of Winter Haven’s growing communities.

Listing is courtesy of: MARK SPAIN REAL ESTATE (855-299-7653)

Listing Agent: Danielle Williams (813-297-8258)

Remarks: Let's make a deal!! Bring them an OFFER!! Turn Key House on the North Chain of Lakes. 2023 Roof, 2022 POOL! Welcome to this pristine, beautifully maintained home in the quiet and highly desirable Island Lakes community—where there’s no through traffic and peaceful living comes naturally. Gorgeous real hardwood floors, stand up tub for the later years, huge shed and a low HOA fee. Step outside and you’ll fall in love with the vinyl-planked dock that gives you direct access to the Chain of Lakes, making it ideal for boating, fishing, and sunset cruises. Whether you prefer relaxing in the screened-in outdoor area or lounging by the sparkling pool, this home is designed for anyone who loves outdoor living. Inside, the home is in immaculate condition. It offers three bedrooms, including a spacious master suite complete with a walk-in tub for easy washing and added convenience. Every room feels well cared for, move-in ready, and prepared for its next owner to enjoy. This stunning property truly has it all—comfort, water access, serenity, and style. It’s ready and waiting for the next buyer who wants to fully embrace lakeside living.

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

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

Remarks: Spacious & Updated on a Corner Lot! Welcome home to this beautifully updated 3-bedroom, 2-bath mobile home situated on a generous .41-acre corner lot with no shortage of outdoor space. Fully fenced for privacy, this property offers both comfort and functionality with room to spread out. And the best part is....NO HOA! Inside, you’ll find NEW WINDOWS that enhance energy efficiency and fill the home with natural light. The open and practical layout features a living room and a separate family room. Enjoy your large primary suite complete with a walk-in closet and private bath, creating a relaxing retreat. Two additional bedrooms provide flexibility for family, guests, or a home office. The AC, appliances and roof were all updated in 2017 so you will have peace of mind moving forward. Step outside to the back porch, perfect for morning coffee, grilling, or enjoying Florida evenings. In the backyard you also have a 110-volt receptacle with a 30-amp breaker for RV hook up. With ample yard space for pets, storage, or future additions, this corner-lot property offers incredible versatility. You have your own little slice of heaven with the privacy you'll love. Ideal for those seeking space, privacy, and affordability—this move-in-ready home checks all the boxes. Schedule your showing today!

Listing is courtesy of: REGAL REAL ESTATE LLC (863-660-7927)

Listing Agent: Tammy Storie (863-698-6000)

Remarks: Charming & Renovated Single Family Home With NO HOA & Great Investment Potential! Welcome to this cozy 3 Bed, 1 Bath residence that features a seamless open floor plan, with a bright living room and dining room combo that flows into the modern kitchen. The interior has been thoughtfully updated with luxury vinyl and tile flooring throughout, providing a stylish and easy-to-clean environment. The private backyard is spacious and perfect for outdoor gardening or relaxing. Located just 5 miles from LEGOLAND Florida, this property offers excellent access to major highways, hospitals, lakes, and all of Central Florida's top attractions. The home is "rental-ready" and has strong income potential as a short-term or long-term rental. Schedule a private tour and make this beautiful home your new residence or add to your income producing profolio... Matterport 3D tour is available that provide virtual 3D tour & room measurements.

Listing is courtesy of: KN PREMIER REALTY, INC (407-668-8888)

Listing Agent: Guanhua Zhang (407-668-8888)

Remarks: Under Construction. This BEATIFUL ROBIE Model home has 5 bedrooms, 3 baths & a 2-car garage-2447 SqFt. NEWLY UPGRADED! Large 2-STORY open floor plan with Living & Dining room & Kitchen to entertain & enjoy the company of your guests. One bedroom located in the first floor, W/FULL BATH. Your very spacious master suite located on the 2nd floor with a large walk-closet & a double sink vanity with stall shower. This Home provides Stainless Appliances which include range, hood microwave, refrigerator, dishwasher and much more. We also provide Smart Home Technology which allows you to set the scene and connect to your home with your voice, from your smart phone, or through the smart panel interface. Your Smart Home comes with Alarm app, Echo Dot, Kwikset Smart Front Lock, IQ Panel, SkyBell, Z-Wave Thermostat, and a Z-Wave Light Switch. *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. Let me Introduce you to the Astor this 1593 Sqft. 3 Bedroom 2 Bath home with the Garage in the rear 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 Astor has an Open Floor plan that allows you to entertain guest even if they are in the living or dining room. Spacious bedrooms and an Owners Suite that can easily fit a King size bed. If you like sitting outside, you have a covered lanai that is perfect for BBQing. 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: Short Sale. Located in the Villamar community of Winter Haven, this 3-bedroom, 2-bath home built in 2023 offers modern construction with a two-car garage and a functional layout designed for everyday living. The home features open living spaces, well-sized bedrooms, and contemporary finishes typical of newer construction. The property appears to require cosmetic refreshing, presenting an opportunity for buyers to personalize a relatively new home without undertaking a major renovation. With a low HOA of approximately $212 and no flood zone designation, this home offers both affordability and added peace of mind. Conveniently located near shopping, dining, schools, and major roadways throughout Winter Haven and Polk County. Buyers are encouraged to conduct their own inspections to determine condition. Agents: Please review all private remarks prior to scheduling a showing.

Listing is courtesy of: KELLER WILLIAMS ELITE REALTY (239-949-8338)

Listing Agent: Jonathon, Pa Mcleod (239-357-8938)

Remarks: Welcome to this beautifully updated home in Winter Haven! This move-in ready property combines classic charm with modern upgrades, featuring stunning high-gloss marble-style porcelain flooring throughout that creates a bright and elegant living space. Enjoy a spacious layout filled with natural light, a well-maintained kitchen with stainless steel appliances, wood cabinetry, and a stylish backsplash — perfect for everyday living. The home also offers a renovated bathroom with modern finishes and a convenient interior laundry area. Step outside to a large, fully fenced backyard, ideal for entertaining, pets, or simply enjoying your own private outdoor space. The covered carport and extended driveway provide ample parking. Located in a quiet, well-established neighborhood, this home is perfect for first-time buyers or investors. Property is being sold AS-IS, presenting a great opportunity for buyers looking for value and flexibility. Schedule your private showing today!

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

Listing Agent: Gabriel Rivera Gonzalez (407-724-4717)

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: Welcome to this beautifully updated 3-bedroom, 1-bath home in Winter Haven! Move-in ready and filled with recent improvements, this property offers comfort, style, and peace of mind. The kitchen was completely updated in May 2025 with new cabinets, granite countertops, and sink, creating a fresh and modern space for everyday living. Major system upgrades include a new roof with warranty (April 2025), new electrical panel with warranty (May 2025), new hot water heater (September 2024), and updated A/C coils and air handler box (January 2024). New flooring installed in October 2025 adds to the home's updated appeal. The living area features a built-in entertainment center with fireplace, added in March 2025, creating a cozy focal point for relaxing or entertaining. Step outside to enjoy the screened back patio, where you'll also find the laundry area for added convenience. Conveniently located near shopping, dining, schools, and major roadways, this well-maintained home is ready for its next owner. Schedule your private showing today!

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

Listing Agent: Tiffany Steck (937-430-9119)

Remarks: This BEATIFUL HARPER Model home is located in the quaint town of Winter Haven. Ski capital & home of LEGOLAND. The NEWLY UPDATED HARPER has 4 bedrooms, 2baths & a 2-car garage - 1665 SqFt. This new model has an open floor plan with a spacious GREAT room off the kitchen to entertain & enjoy the company of your guests. You will love the split floor plan with beautiful & spacious master suite with walk in closet & en suite bathroom away from the other 3 bedrooms. Home comes with WHIRLPOOL Stainless Appliances- range, hood microwave, refrigerator & dishwasher. Home also comes with faux wood blinds throughout & has Smart Home Technology which allows you to set the scene & connect to your home with your voice, from your smart phone. *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: Honey, stop the car! This is the one you’ve been waiting for. This beautifully maintained 4-bedroom, 2-bathroom home sits on a spacious 0.45-acre fenced lot, offering the space, privacy, and outdoor lifestyle today’s buyers are searching for. Enjoy the soon-to-be easy access to Avalon and Disney via Sawgrass Rd extension. Step inside and you’re welcomed by a spacious foyer that flows into a cozy sitting area and formal dining room—perfect for gathering with family or entertaining guests. The open-concept kitchen features a charming breakfast nook and overlooks the main living area, creating a warm, connected space where everyone can come together. The private primary suite is a true retreat, complete with dual vanities, a relaxing soaking tub, a walk-in shower, and a large walk-in closet. The split floor plan provides privacy for everyone, while soaring high ceilings throughout the home create a bright and airy feel. Step outside and discover what truly sets this property apart—an outdoor entertainer’s dream. The covered paver lanai opens to a massive fenced backyard with endless possibilities for entertaining, gardening, play, or simply enjoying peaceful Florida evenings. Additional highlights include: New roof installed in 2021 Covered paver lanai perfect for outdoor gatherings Large private backyard with storage shed Two-car garage Interior laundry room Move-in ready condition in a quiet, established neighborhood Homes with this much space, privacy, and charm don’t come around often. Don’t miss your chance—schedule your private showing today before someone else calls it home.

Listing is courtesy of: FUTURE HOME REALTY INC (813-855-4982)

Listing Agent: Paul Shearn (407-713-2127)

Remarks: Welcome to Vienna Square — a vibrant, beautifully maintained 55+ gated community where resort-style living meets true low-maintenance comfort. This charming 2-bedroom, 2-bath villa offers 1,231 sq ft of thoughtfully designed living space, highlighted by an open-concept layout and an inviting Florida Room with its own portable A/C, giving you year-round flexibility for relaxing, crafting, reading, or entertaining. Inside, you’ll find a bright living and dining area, a well-appointed kitchen, and a desirable split bedroom floor plan that provides privacy for you and your guests. The Florida Room adds valuable extra square footage and seamlessly extends your living space. Life at Vienna Square is all about ease and enjoyment. Residents have access to an impressive lineup of amenities, including a clubhouse, tennis courts, heated community pool, hot tub, movie room, billiards room, fitness center, and a full calendar of weekly social activities that make it easy to stay active and connected. The HOA takes care of the details so you don’t have to — yard maintenance is included, along with exterior paint every 10 years and roof replacement every 15 years. Even better, this villa already benefits from a new roof and fresh exterior paint completed just 2 years ago, offering added peace of mind. Perfectly located just minutes from the brand-new Publix, dining, medical facilities, and all that Winter Haven has to offer, this home delivers the ideal blend of comfort, convenience, and an engaging active-adult lifestyle. Move-in ready, beautifully maintained, and set within one of Winter Haven’s most desirable 55+ communities — this villa is a standout opportunity.

Listing is courtesy of: RE/MAX PRIME PROPERTIES (407-347-4512)

Listing Agent: Tina Bircher (321-228-4267)

Remarks: Welcome to this beautiful 3-bedroom, 2-bathroom home in the heart of Winter Haven! Featuring a desirable open floor plan, this home offers comfortable living with plenty of space to relax and entertain. The modern kitchen is highlighted by granite countertops, ample cabinetry, large island, and a seamless flow into the main living area, making it perfect for gatherings. Just off the entrance, you’ll find a versatile flex space that can easily serve as a home office, dining room, or playroom to suit your needs. The spacious primary suite is a true retreat, complete with a large bedroom and dual master closets, offering plenty of storage. Two additional bedrooms and a second full bathroom provide comfortable accommodations for family or guests. Step outside from the large sliding doors to enjoy the fenced-in backyard, ideal for pets, outdoor activities, or relaxing evenings. Located in a great neighborhood in the heart of Winter Haven, this home is conveniently close to shopping, restaurants, and local schools, offering both comfort and convenience. Don’t miss the opportunity to make this wonderful home yours!

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

Listing Agent: Bethany Jack (606-584-0518)

Remarks: Under Construction. The Allex II is one of our one-story floorplans featured in Villamar in Winter Haven, Florida. With 2 exteriors to choose from, the Allex is sure to turn heads. Inside this 3-bedroom, 2-bathroom home, you’ll find 1,504 square feet of comfortable living. The living area is an open concept, where your kitchen, living, and dining areas blend seamlessly into a space perfect for everyday living and entertaining. Relax on the covered lanai looking out to your backyard. The kitchen features quartz countertops, stainless-steel appliances and a walk-in pantry which are sure to both turn heads and make meal prep easy. You’ll never be too far from the action with the living and dining area right there. In every bedroom you’ll have carpeted floors and a closet in each room. Whether these rooms become bedrooms, office spaces, or other bonus rooms, there is sure to be comfort. The primary bedroom located in the rear of the home has its own attached bathroom that features a walk-in closet and all the space you need to get ready in the morning. Sharing a sink isn’t a worry with the double vanity. Like all homes in Villamar, the Allex II includes all concrete block and also smart home technology, which allows you to control your home anytime with your smart device while near or away. Contact us today and find your home at Villamar. *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. Open flow sets the tone for this elegant new Crestone II two-story townhome. There are a total of three bedrooms. The first level features a spacious and flexible open-concept layout shared between the kitchen, dining room and family room, maximizing the interior living space. Two secondary bedrooms and a lavish owner’s suite featuring a full bathroom comprise the second floor. Serenity at Peace Creek Reserve is a masterplan community of new townhomes with a beautiful natural creek. Winter Haven is the chain of lakes city, with over 26 linked together by a canal. There are lots of shops, restaurants, and bike paths. Peace Creek Reserve is what you have been looking for. A safe small town feel with convenience, the perfect place to raise a family.

Listing is courtesy of: LENNAR REALTY (800-229-0611)

Listing Agent: Ben Goldstein (407-310-7677)

Remarks: Welcome to 563 Honey Bell Rd, a home that beautifully blends modern comfort, style, and the relaxed Florida lifestyle. From the moment you arrive, you’ll feel the inviting atmosphere of this well-kept community and the pride of ownership reflected throughout this 4-bedroom, 2-bath residence. Step inside and experience a bright, open floor plan filled with natural light—an uplifting space that instantly feels like home. The heart of the property is its elegant, contemporary kitchen, featuring stainless steel appliances, a spacious island, and generous counter space that makes cooking, gathering, and entertaining effortless. The seamless flow into the living and dining areas creates a warm, connected environment perfect for everyday living and special moments with family and friends. Large windows overlook the backyard, allowing sunlight to pour in and giving the home a fresh, airy feel throughout the day. The primary suite offers a peaceful retreat with a spacious layout and a private bath designed for relaxation. Three additional bedrooms provide versatility for guests, a home office, or a growing household. Every corner of this home feels thoughtfully designed to support comfort, convenience, and a lifestyle that feels elevated. Step outside to a spacious backyard that invites you to unwind, enjoy the Florida breeze, or create the outdoor oasis you’ve always imagined. Whether it’s morning coffee on the porch, weekend barbecues, or quiet evenings under the sky, this outdoor space offers the perfect backdrop for relaxation and connection. Lake view. Located in one of Winter Haven’s most desirable and fast-growing areas, this home offers exceptional convenience for professionals commuting to Orlando, Lakeland, or Davenport. You’re just minutes from shopping, dining, hospitals, scenic lakes, parks, and the excitement of Legoland Florida. Here, you enjoy the rare combination of accessibility, tranquility, and a welcoming neighborhood atmosphere. An added advantage: this property already features a reliable tenant in place, making it an excellent opportunity for investors seeking immediate income in a high-demand rental market. Whether you’re looking for a primary residence or a strong investment asset, 563 Honey Bell Rd delivers value, comfort, and long-term potential. This home is more than a place to live—it’s a space to build memories, find comfort, and enjoy the best of Central Florida living. Move-in ready, beautifully maintained, and perfectly located, it offers an exceptional opportunity for anyone seeking quality, convenience, and a lifestyle that feels truly elevated.

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

Listing Agent: Braulymar Gonzalez Inojosa (239-672-3217)