Homes For Sale in Winter Haven 33881 - 346 homes

Remarks: Welcome to 239 Sunfish Dr, a 4-bedroom, 2-bath home in one of Winter Haven’s growing communities, offering modern comfort, thoughtful upgrades, and outdoor spaces designed to be enjoyed year-round. Built in 2021 and offering nearly 2,000 square feet of living space, this home is move-in ready and packed with value for homeowners and investors alike. Inside, you’ll find a spacious open-concept layout with a split-bedroom floor plan that offers both functionality and privacy. The kitchen opens seamlessly to the main living and dining areas, creating the perfect flow for everyday living and entertaining. With four full bedrooms, there is plenty of space for a growing household, guests, or a home office setup. What truly sets this home apart is the outdoor living experience. Enjoy a fully screened-in back porch, perfect for relaxing in the evenings without worrying about bugs, plus an extended outdoor living area ideal for grilling, gathering, or simply unwinding. A custom paver walkway leads to a charming gazebo, creating the perfect shaded retreat to enjoy the outdoors while staying out of the Florida sun. Whether you're hosting friends or enjoying a quiet morning coffee, this backyard was designed to be used and enjoyed. Additional upgrades include a full gutter system for added function and protection, helping direct water away from the home and adding peace of mind during Florida’s rainy season. Located in a growing area of Winter Haven with convenient access to shopping, dining, schools, and major roadways, 239 Sunfish Dr offers the perfect blend of newer construction, smart upgrades, and comfortable Florida living. Whether you're looking for your next home or a strong long-term investment, this one is easy to love.

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

Listing Agent: Noah Stevens (863-400-1172)

Remarks: Under Construction. The Ponte Vedra floor plan at Willowbrook North offers spacious two-story living with 5 bedrooms, 3 full baths, and approximately 2,371 square feet of thoughtfully designed space. This open-concept home features a modern kitchen overlooking the great room and dining area, a spacious primary suite, flexible living areas, and available options. Located near Lake Fannie and adjacent to Willowbrook Golf Club, Willowbrook North offers scenic surroundings with convenient access to shopping, dining, parks, downtown Winter Haven, and major commuter routes to Orlando and Tampa. Buyers will also enjoy energy-efficient features and modern interior finishes.

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

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

Remarks: Back on market buyers financing fell through. Welcome home! Your forever home is located near downtown Winter Haven and just a short distance from Polk State College. Completely remodeled in 2021 with a New Roof, New A/C, New Water Heater, New Electrical system, new windows new kitchen (Quartz Countertops), new appliances, new floors (Vinyl). This home has a huge, oversized corner lot and with summer around the corner, this will be the place for all the summer BBQ's.

Listing is courtesy of: FLATFEE.COM (954-965-3990)

Listing Agent: Cliff Glansen

Remarks: Under contract-accepting backup offers. Short Sale. ***SHORT SALE*Discover Your Dream Home at Lakeside Landing! Welcome to this immaculate home in the picturesque community of Lakeside Landing! This property offers the ultimate in modern living, combining comfort, style, and functionality. It's move-in ready and equipped with smart home technology, energy-efficient windows, and SOLAR PANELS to help you save on energy costs. Plus, enjoy the privacy of having no rear neighbors and a fully fenced large yard. Recent Upgrades and Features Flooring: Experience the elegance of luxury vinyl flooring throughout the home, with upgraded plush carpeting in the primary bedroom. The bathrooms boast stylish tile flooring. Bathroom Updates: Enjoy the convenience of brand-new toilets and an updated guest bathroom that features a new vanity and mirror. Kitchen Enhancements :Crown molding on kitchen cabinets Added cabinet hardware, Stunning new backsplash, Farm-style door leading to the pantry New wooden pantry shelves Additional Interior Features: Ceiling fans in both the primary bedroom and living area Neutral color scheme with fresh, whole-house interior paint Outdoor Living Relax and unwind on your screened-in porch while overlooking your spacious, fenced yard. It's the perfect spot for enjoying a morning coffee or evening gatherings with friends and family. Community Amenities Lakeside Landing offers a variety of community features to enhance your lifestyle, including: Resort-style pool: Dive into relaxation and enjoy the sun by the pool. Ideal Location Convenience is at your doorstep with easy access to major highways like 27 and I-4. Nearby attractions include Legoland, Disney World, and Universal Studios, making this home an ideal location for entertainment enthusiasts. Additionally, Posner Park is just around the corner for all your shopping needs. Don't miss the opportunity to make this like-new, energy-efficient home yours. Come check it out and experience the best of Lakeside Landing living!*CDD INCLUDED IN TAXES . OWNER MOTIVATED

Listing is courtesy of: COLDWELL BANKER REALTY (407-352-1040)

Listing Agent: Brenda Anglada (407-493-3464)

Remarks: This dynamically unique home in Winter Haven offers waterfront living, with direct access to the renowned Chain of Lakes. Ideally situated on Lake Cannon, the property delivers stunning water views and a peaceful setting that’s hard to match. Located within a gated, low-maintenance community, this home allows you to enjoy all the perks of ownership without the added upkeep. The community pool and hot tub sits just steps away—offering the feel of a personal pool without the responsibility. Residents also enjoy access to a community dock with first-come, first-served boat slips, making it easy to embrace the lake lifestyle. The property itself features a fenced yard, and a beautiful pergola—perfect for relaxing, entertaining, or enjoying the serene lakefront setting. The garage is equipped with a 2021 split-unit AC system, creating a versatile space ideal for a workshop, gym, or even additional living area. For added peace of mind, the home includes a gas-powered generator that automatically kicks on when needed. Inside, the home is nothing short of impressive—boasting soaring cathedral ceilings, expansive balconies with breathtaking views, and a layout that is both majestic and thoughtfully designed. The primary suite is a true retreat, featuring a private balcony, dual vanities, and a luxurious soaking tub designed for relaxation. Additional office and bonus spaces offers flexibility and can easily be converted into extra bedrooms to fit your needs. Updates include two AC units installed in 2017, along with a durable metal roof added in 2021 and the roof tiles were sealed and coated for an extra long life. Whether you’re looking for a full-time residence, a seasonal getaway, or a place to gather with family and friends, this home delivers a warm, inviting atmosphere with unique architectural character throughout. Enjoy peaceful mornings overlooking the lake, afternoons gardening in your yard, or evenings unwinding on the balcony while taking in the surrounding wildlife. Conveniently located near shopping, grocery stores, and Home Depot, this is more than just a home—it’s a lifestyle. A property like this must be seen in person to truly appreciate the grandeur and exceptional living experience it offers.

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

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

Remarks: Florida Living at Its Best! Welcome home to this beautifully updated 2-bedroom, 2-bath residence offering the perfect combination of comfort, style, and convenience. From the moment you walk through the door, you'll be impressed by the bright, open floor plan, modern finishes, wood-look flooring, and inviting living spaces designed for everyday living and entertaining. The spacious primary suite serves as a private retreat and features sliding glass doors leading to a screened and covered lanai. A portion of the lanai has been enclosed to create a flexible bonus room—ideal for a home office, reading nook, fitness area, or hobby room. Step outside to your private tiled patio, the perfect place to enjoy your morning coffee, unwind after a long day, or host family and friends. This sought-after community offers amenities rarely found at this price point, including assigned covered parking, a sparkling community pool, and direct access to beautiful Lake Smart with a private boat ramp. Whether you enjoy boating, fishing, kayaking, or simply watching the sunset over the water, you'll love the lifestyle this community provides. Located just minutes from shopping, restaurants, medical facilities, and major roadways, this move-in-ready home offers the convenience buyers are looking for and the Florida lifestyle they dream about. Opportunities like this don't come along often. Schedule your private tour today and discover why this could be the perfect place to call home.

Listing is courtesy of: TRUE FLORIDA REALTY LLC (863-337-9667)

Listing Agent: Diana Acosta (914-562-3386)

Remarks: Under contract-accepting backup offers. Tucked away on a dead-end street in Winter Haven, this spacious lakefront home on Lake Buckeye offers almost 2,400 square feet of living space, a private dock, and a rare combination of privacy, character, and major updates. Situated on over 1/3 of an acre, the property features low traffic, peaceful waterfront views, and a fenced backyard area for pets or animals. Inside, you’ll find a massive living room with triple sliding glass doors overlooking the lake, a floor-to-ceiling stone wood-burning fireplace, and beautiful wood ceilings that create a warm lakeside atmosphere. All 4 bedrooms are positioned on one side of the home, while the oversized living and entertaining areas maximize the waterfront setting and provide excellent flexibility for future remodeling or customization. Major improvements include a metal roof (2019), HVAC system (2016), water heater (2018), upgraded double-pane storm-resistant windows (2010), re-piped plumbing, septic pumped in July 2025, new drain field installed in 2025, and refrigerator replaced in 2023. Lake Buckeye provides a more private setting with fewer homes on the lake while still providing public boat ramp access. Conveniently located a few miles from downtown Winter Haven and only about a mile from Polk State College, this property combines waterfront living, space, and long-term value in a highly convenient location.

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

Listing Agent: Don Jerue (863-259-9550)

Remarks: Under contract-accepting backup offers. 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: Winter Haven's premier condominium located directly overlooking the picturesque Lake Spring that is part of the famous 17-lake Winter Haven Chain of Lakes. Be the first to enjoy this beautiful extensively remodeled and upgraded 5th floor corner unit directly off of the elevators. Lots of natural light through the expansive windows looking out to Lake Spring and the pool area. Lots of storage closets and an extra storage locker. Its turn-key & ready to move into. Exquisitely maintained building and has passed the newly required Florida State Milestone Inspection & Reserves Study. Many amenities including a covered assigned parking space, guest parking, boat slips & fishing pier, paver brick pool area, large work-out room, library and community room w/ kitchen. Outdoor grills for your use, shuffle board & patio furniture on the huge pool deck overlooking Lake Spring. Publix shopping center by walking across the side street is a great convenience. Close to downtown No pets or smoking. Owner will consider different leasing and/or purchase & financing options. Short term seasonal or long term lease. Tenants and/or buyers have to be approved and interviewed by the HOA as this is a 98% owner occupied building. Nicest condominium building in Polk County with full-time maintenance and management on-site daily.

Listing is courtesy of: KLINE REAL ESTATE SERVICES (863-287-0204)

Listing Agent: Scott Kline (863-287-0204)

Remarks: One or more photo(s) has been virtually staged. Price Improvement! Charming 1920s home in Winter Haven featuring original hardwood floors, modern updates, and desirable R-3 zoning. Located in one of Central Florida's fastest-growing markets, this move-in-ready property offers flexibility, character, and investment potential. Inside, you'll find a bright foyer, spacious living and dining areas with original hardwood flooring, and a functional kitchen complete with refrigerator, range, microwave, and dishwasher. The split-bedroom layout provides added privacy, while a bonus flex space off the primary bedroom is ideal for a home office, nursery, gym, or hobby room. A large Florida room adds extra living space and offers direct driveway access, perfect for entertaining or relaxing. The R-3 zoning creates opportunities for investors and future development potential (buyers should verify permitted uses with the City of Winter Haven). Conveniently located near downtown Winter Haven, LEGOLAND® Florida Resort, shopping, dining, medical facilities, major highways, and the Chain of Lakes. Now offered at a reduced price—schedule your private showing today!

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

Listing Agent: Michael Hochadel (863-604-0018)

Remarks: Immaculate 4-Bedroom, 3-Bathroom Plus Office Home in the Coveted Crossroads at Lake Region Welcome to this beautifully maintained residence located in the highly desirable gated community of Crossroads at Lake Region. This spacious four-bedroom, three-bathroom home with a dedicated office offers the perfect blend of comfort and functionality. As you arrive, you’re welcomed by a handsome paver driveway that adds both charm and curb appeal. Step inside to soaring vaulted ceilings and an open-concept floor plan, ideal for both everyday living and entertaining. Expansive living and dining areas flow effortlessly, creating a bright, airy feel throughout the home. The oversized primary suite, located just off the main living area, is a true retreat. It features a luxurious en suite bathroom complete with a large soaking tub, separate walk-in shower, dual sinks, and a spacious walk-in closet. Fresh interior paint gives the home a crisp, updated look, and a new roof provides added peace of mind. A private office offers the perfect space to work from home or can easily flex to fit your lifestyle. This home is situated just a short distance away from the community pool and hot tub. This one checks all the boxes!

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

Listing Agent: Jill Lingenfelter (863-242-0900)

Remarks: New Price and $2500 Seller Credit!! Relocating to Florida? This pristine 5-bedroom, 3-bath home offers nearly 2,700 square feet of thoughtfully designed living space in the heart of Central Florida, providing the space, flexibility, and value many buyers from northern states and high-cost markets are seeking. Priced at $374,900—approximately $140 per square foot—this home delivers exceptional value compared to similar properties in California and many northern metro areas. The well-planned layout includes five true bedrooms, three full bathrooms, and a versatile flex space that could easily be converted into a sixth bedroom. This additional space makes the home ideal for growing families, multigenerational living, aging parents, young adults living at home, or a private home office or hobby room. A guest suite on the first floor adds even more functionality and convenience. The main living areas feature upgraded tile flooring, while the kitchen is finished with granite countertops and ample workspace for everyday living and entertaining. The home has been meticulously maintained and is in pristine, move-in-ready condition. Outdoors, enjoy added privacy with no rear neighbors, creating a peaceful and open backdrop rarely found in newer communities. Located just 5 minutes from downtown Winter Haven, residents enjoy easy access to historic charm, the Ritz Theatre, Saturday farmers markets, a beautiful public library, and a growing selection of high-end and locally owned dining options. A brand-new Publix grocery store is currently under construction within walking distance, adding everyday convenience and long-term appeal. The community features a very low HOA and no CDD fees, helping keep ownership costs manageable—an important advantage for relocating buyers. Ideally positioned just 5 minutes from Legoland Florida and approximately 30 minutes from Disney, the home offers access to Central Florida attractions while maintaining a comfortable residential setting. With generous square footage, flexible living spaces, privacy, and proximity to downtown amenities, this home is an outstanding opportunity for buyers ready to trade cold winters or high housing costs for a more flexible and comfortable Florida lifestyle.

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

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

Remarks: One or more photo(s) has been virtually staged. Step into this renovated farmhouse charm : 2-bedroom, 2-bathroom home, nestled on a spacious lot in the established Villa Manor neighborhood. NO HOA This move-in-ready residence presents luxury finishes, laminate flooring throughout, a sleek new kitchen with updated cabinets, carrara white quarts countertops, and stainless steel appliances, and a freshly tiled bathroom with contemporary finishes. Fresh interior and exterior paint, and upgraded lighting fixtures. Roof 2020 - - Repipe 2025 - The large backyard offers plenty of space for outdoor living or future expansion. Located minutes from local schools, parks, and downtown Winter Haven’s shops and restaurants, this home is perfect for first-time buyers, downsizers, or investors seeking turnkey potential.

Listing is courtesy of: KELLER WILLIAMS LEGACY REALTY (407-855-2222)

Listing Agent: Daniel Araque (321-276-0747)

Remarks: Experience elevated living in this beautifully maintained 3 bedroom, 2 bathroom residence located in the highly desirable Country Walk community in Winter Haven. Designed with style and comfort in mind, this home showcases custom luxury finishes throughout the living room and bedrooms, creating an elegant and inviting atmosphere. The open concept layout offers the perfect blend of functionality and sophistication, while the modern kitchen serves as the centerpiece of the home with sleek cabinetry, quartz countertops, and ample space for cooking and entertaining. The spacious primary suite provides a private retreat with a walk in closet and a beautifully appointed bathroom. Step outside and enjoy the extended paver patio, an ideal space for relaxing or hosting family and friends, all enclosed by a white PVC privacy fence that enhances both comfort and privacy. Conveniently located near shopping, dining, schools, medical facilities, and major highways, this home is also just minutes from LEGOLAND Florida Resort and many of Central Florida’s most popular attractions. Combining stylish interior design, exceptional outdoor living, and a prime location, this residence offers an outstanding opportunity to enjoy the best of the Florida lifestyle.

Listing is courtesy of: KELLER WILLIAMS LEGACY REALTY (407-855-2222)

Listing Agent: Maria Santacruz (407-552-8213)

Remarks: Welcome home to Brenton Manor! This move-in ready 3-bedroom, 2-bathroom split-plan home checks every box — and then some. The open-concept kitchen flows seamlessly into the great room, creating the perfect space for entertaining or relaxing after a long day. Step outside to your private, fully fenced backyard with no rear neighbors — your own Florida oasis. Big-ticket updates have already been done for you: brand-new 2026 HVAC with UV ray lights and professionally cleaned ductwork, 2026 whole-home water softener system, 2025 tankless water heater, 2025 fresh exterior paint, 2025 gutters, and a 2023 roof. Both bathrooms feature updated showers, so all you need to do is move in and enjoy. Conveniently located near top medical facilities, BayCare Winter Haven Hospital just minutes away, and the nationally recognized Lakeland Regional Health nearby. Everyday conveniences are just as close, with shopping, dining, and retail options all within a short drive. Ideally located for commuters and travelers, this community offers. Ideally located for commuters and travelers, this community offers quick access to Interstate 4, the Polk Parkway (SR-570), and US-27—placing Tampa and Orlando approximately 30 to 40 minutes away and the world-famous theme parks just 35 miles away. Schedule your private showing today!

Listing is courtesy of: COLDWELL BANKER REALTY (407-696-8000)

Listing Agent: Cynthia Davis (407-619-2937)

Remarks: Welcome to this stunning 4-bedroom, 2-bath home located in a vibrant and growing neighborhood. Built in 2020, this modern residence offers the perfect blend of style, comfort, and functionality—ideal for today’s lifestyle. Step inside to discover a bright and spacious open-concept floor plan, perfect for both everyday living and entertaining. The gourmet kitchen is a true centerpiece, featuring rich espresso cabinetry, gleaming granite countertops, stainless-steel appliances, and a massive center island with sink—ideal for hosting gatherings or preparing family meals. Retreat to the primary suite, complete with a generous walk-in closet, dual vanities and a walk-in shower. Three additional bedrooms provide ample space for family, guests, or a home office. Enjoy Florida living at its best on the covered patio, overlooking a large, fully fenced backyard—perfect for summer barbecues, pets, play, and relaxing evenings under the stars. With modern finishes, thoughtful design, and move-in-ready condition, this home is a must-see. Don’t miss your opportunity to own this exceptional property—schedule your private showing today!

Listing is courtesy of: LA ROSA REALTY LLC (321-939-3748)

Listing Agent: Humberto Cuevas (407-725-9971)

Remarks: Seller motivated and open to reasonable offers. Don’t miss this opportunity, schedule your private showing today! Back on market. Buyer’s financing fell through. Move-in ready and meticulously maintained! This spacious 4-Bedroom, 2.5-Bathroom two-story home was built in 2022. The main level offers seamless flow between the living room, dining area, and kitchen perfect for family gatherings. The kitchen showcases granite countertops, stainless steel appliances, a large center island with seating, deep sink, upgraded fixtures, and abundant cabinet space. A private main-floor office/den with double doors adds flexibility for remote work, fitness, or study, plus a convenient half bath downstairs. Upstairs, the generous primary suite features a large walk-in closet and an ensuite bath with dual sinks, granite counters, and an upgraded walk-in shower. The additional bedrooms are spacious, and the upstairs laundry room is centrally located for convenience. Situated on a desirable corner lot, the home offers excellent outdoor space including a covered back porch, ideal for relaxing or hosting gatherings. The backyard provides plenty of room to enjoy Florida living year-round. Lake Lucerne residents enjoy community amenities including two pool, a playground, and beautifully maintained space. Ideally located with easy access to Hwy 27 and approximately 20 minutes to I-4, you’re centrally positioned between Orlando and Tampa, about 45 minutes to Disney, 20 minutes to Legoland, and 35 minutes to Lakeland. Close to Winter Haven Hospital, Downtown Winter Haven, Publix, Walmart, Shopping and more! The roof, AC unit and water heater are all 4 years old.

Listing is courtesy of: HOMESMART (407-476-0451)

Listing Agent: Nan Seelall Llc (352-978-1050)

Remarks: Under contract-accepting backup offers. Nice home 3/1 in Winter Heven

Listing is courtesy of: EMPIRE NETWORK REALTY (407-440-3798)

Listing Agent: Maritza Cruz (863-512-0009)

Remarks: Fixer upper! THIS COULD BE THE ONE. PRIVATE POOL! So many possibilities! Lovely vaulted ceilings, 2 fireplaces, open kitchen, lovely wood accents, mahogany kitchen cabinets, office has a closet and could be converted to a 3rd bedroom 3 car garage/ carport and a separate workshop all on .75 of an acre. roof 10 years old, ac replaced 2024, UVI light 2024

Listing is courtesy of: YELLOWFIN REALTY (813-347-7547)

Listing Agent: Marcia Rains - Nadal, Mrs (813-493-2221)

Remarks: This property is zoned for a duplex and features a large backyard, offering excellent potential for investors. The home is being sold as-is and will be delivered with all items currently inside. Located in a great family-friendly neighborhood, with a new Publix plaza opening nearby adding even more value and convenience to the area.

Listing is courtesy of: FLATFEE.COM (954-965-3990)

Listing Agent: Cliff Glansen