Winter Haven Homes For Sale & Real Estate - 983 homes

Remarks: Welcome to the Eagle Landing community in Winter Haven, FL. This well-maintained single-family home is move-in ready and waiting for its new owner(s). The open-floor concept creates a comfortable flow throughout the main living areas, while the split floor plan provides added privacy for the primary bedroom and bath with spacious walk-in closet. The kitchen features stainless steel appliances and granite countertops, offering both style and functionality. Additional conveniences include a laundry room, two car garage and low HOA dues, making this home an affordable and practical choice. Experience the charm of small-town living while enjoying the growth and expansion happening throughout Winter Haven. Conveniently located just minutes from Legoland, shopping, dining, and entertainment, and centrally positioned between Tampa and Orlando for easy travel in either direction. Solar panels will be paid off at closing, providing the new owner with the benefit of low electricity bills. The spacious backyard offers room to relax or entertain.

Listing is courtesy of: CENTURY 21 WATSON & MYERS REALTY (863-324-1000)

Listing Agent: Carla Miro (786-897-4081)

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: Spacious 4-Bedroom, 3-Bath Pool Home in the admired Lakewood Community. Nestled on an oversized lot with mature trees, this remodeled tri-level home offers a perfect blend of modern luxury and comfort. With a spacious layout, a private pool, and an abundance of natural light, this home is designed for both relaxation and entertaining. As you enter, you’ll immediately notice the bright and airy atmosphere created by large windows that allow natural light to flood the home. The home features stunning luxury vinyl plank flooring and a beautiful brick fireplace, adding warmth and character to the space. The kitchen is of good size and boasting sleek countertops, new modern appliances, and ample cabinet space. Enjoy casual meals in the eat-in kitchen or step outside to the screened-in porch, an ideal spot for dining al fresco or simply relaxing while overlooking the expansive backyard and pool. Come add your personal touches and make this house your beautiful home!

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

Listing Agent: Michelle Armbruster (863-521-6879)

Remarks: Under contract-accepting backup offers. Welcome home to this beautifully updated 3-bedroom, 2-bath residence ideally situated in the heart of Winter Haven, just minutes from downtown and surrounded by the area’s picturesque lakes. This move-in ready home has been thoughtfully upgraded throughout, offering stylish vinyl flooring, refreshed bathrooms, modern light fixtures, and a beautifully renovated kitchen featuring granite countertops, updated cabinetry, a trendy backsplash, and stainless steel appliances. The inviting living room is anchored by a cozy fireplace, creating the perfect space to relax or entertain. Step outside to your private, fully fenced backyard complete with a fire pit—ideal for enjoying Florida evenings with family and friends. Additional highlights include a spacious two-car garage with laundry area, a convenient enclosed storage space, and a newer roof (2022) for added peace of mind. With no HOA and a prime location close to shopping, dining, and everything downtown Winter Haven has to offer, this home truly combines comfort, style, and convenience. Don’t miss your chance to make it yours!

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

Listing Agent: Robert Johnson (813-364-2250)

Remarks: PRICED BELOW RECENT APPRAISED VALUE OF $795,000 — APPRAISAL AVAILABLE FOR REVIEW! (Real Matterport Tour & Videos in Virtual Tour Links) Rare opportunity to own one of the most desirable waterfront golf course homes in Cypresswood Golf & Country Club. Positioned on a private corner lot overlooking the pond, 4th green, and 5th tee, this extensively updated 5-bedroom, 4.5-bath estate offers nearly 4,200 SQ FT of luxury living with breathtaking views, incredible sunsets, and no rear neighbors. Inside, soaring ceilings, engineered hardwood floors, custom finishes, a gas fireplace, expansive entertaining spaces, and a completely secret hidden room create a one-of-a-kind luxury experience unlike anything else on the market. The chef’s kitchen features stainless LG appliances, propane gas range, custom cabinetry, oversized island, and seamless flow into the family room and entertainer’s wet bar — all designed around the stunning golf and water views. The downstairs owner’s suite offers a private retreat with spa-style bath, oversized closet, and direct pool views, while upstairs features spacious guest suites and a dedicated movie room/loft ideal for entertaining, working from home, or multigenerational living. The screened outdoor living area feels like a private resort with a sparkling pool, newer gas heater, outdoor summer kitchen with gas grill, and peaceful panoramic golf course and waterfront scenery. Major upgrades include new downstairs HVAC (2025), updated engineered hardwood flooring, newer pool equipment and pump, tankless gas water heaters, roof updates and annual inspections, fresh interior paint, and more. Located inside the 24-hour guard-gated Cypresswood Golf & Country Club community featuring championship golf, tennis, pickleball, clubhouse dining, fitness center, and resort-style amenities. Conveniently located near Legoland, Disney, Orlando attractions, top restaurants, shopping, malls, medical facilities, and major highways with easy access to both Tampa and Orlando. Luxury golf properties with this combination of views, privacy, updates, lot positioning, and value rarely become available.

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

Listing Agent: Justino Zoppe (417-848-1383)

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: Come see 2953 Whispering Trails Dr, a residence showcasing recent fresh interior paint and fresh exterior paint for a clean, cohesive appearance. The kitchen is equipped with all stainless steel appliances, and the primary bathroom provides practical double sinks. Outside, a welcoming patio leads to a fully fenced in backyard. This move-in ready property blends comfort and recent updates seamlessly. Included 100-Day Home Warranty with buyer activation

Listing is courtesy of: OPENDOOR BROKERAGE LLC (480-462-5392)

Listing Agent: Karen Albright (480-462-5392)

Remarks: Come see 1100 Carefree Cove Dr, recently improved with a new roof, fresh exterior paint, and fresh interior paint, presenting a comprehensively refreshed presentation. Partial flooring replacement further updates the interior living spaces, while a fenced in backyard provides practical outdoor areas. This property embodies a fresh approach to comfortable living. Included 100-Day Home Warranty with buyer activation

Listing is courtesy of: OPENDOOR BROKERAGE LLC (480-462-5392)

Listing Agent: Karen Albright (480-462-5392)

Remarks: Short Sale. SHORT SALE APPROVED. LIST PRICE APPROVED BY BANK. Amazing opportunity to purchase a 3 bedroom, 2 bath home situated on a spacious ¼ acre lot with NO HOA. Priced to sell and offering exceptional value, this property will not last long. The home features an open floor plan with a spacious living room, kitchen and dining combination, and additional family room space. The primary bedroom is generously sized and includes a private en suite bathroom. A bonus room with exterior access provides flexible space for a home office, game room, or additional living area. Attached oversized 1 car garage. The kitchen includes appliances and a breakfast bar. The covered outdoor area and wood deck have great potential for entertaining, and the fenced backyard with no rear neighbors adds privacy and space. Subject to lender approval. Home does now have some deferred maintenance.

Listing is courtesy of: THE AGENCY FL (407-335-4119)

Listing Agent: Cristina Porretto (407-264-1870)

Remarks: Location, Location , Location Rare opportunity! Exceptional home with 4 bedrooms, 2 baths, and 2-car attached garage. Open-concept living with quartz kitchen, center island, and ceramic tile floors. Primary suite with walk-in closet and an-suite bath. Features include covered screened lanai, fully fenced yard, gutters, irrigation, and inside laundry. Desirable location, this home won’t last!

Listing is courtesy of: MIHOUSE REALTY LLC (407-286-2690)

Listing Agent: Martha Leighton, Pa (407-223-7767)

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: One or more photo(s) has been virtually staged. Welcome to this beautifully updated three-bedroom, two-bathroom home with a two-car garage, offering 1,866 square feet under roof in the desirable community of Winter Haven. From the moment you arrive, you’ll appreciate the freshly painted exterior and updated landscaping that create strong curb appeal, setting the tone for what awaits inside. Step through the front door into a bright and refreshed interior featuring newly painted walls, updated doors, and modern light fixtures. The great room is highlighted by new luxury vinyl plank flooring that continues into all bedrooms, offering both durability and a clean, contemporary feel. The kitchen is designed for both functionality and style, featuring brand-new stainless-steel appliances and a seamless flow into the main living space—perfect for everyday living and entertaining. The split-bedroom layout provides privacy, with a spacious primary suite that includes updated mirrors and finishes in the en suite bathroom. Two additional bedrooms and a second full bath offer flexibility for family, guests, or a home office. Throughout the home, you’ll find new ceiling fans, updated blinds for window treatments, and thoughtful upgrades that make this home truly move-in ready. Additional improvements include a Brand-new roof, new hot water heater, and a freshly painted garage floor, adding both value and peace of mind. Located in a sought-after area of Winter Haven, this home offers convenient access to shopping, dining, and local attractions, while still being tucked into a welcoming community known for its charm and proximity to the area’s beautiful lakes. This is a fantastic opportunity to own a fully updated home in one of Central Florida’s most desirable and growing locations.

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

Listing Agent: Jason Stone (863-838-8972)

Remarks: One or more photo(s) has been virtually staged. Beautiful, well-cared-for 2BR/2BA villa in a maintenance-free 55+ community — ready for a new owner. Single-level, move-in ready home with a bright, open floorplan, remodeled kitchen and stainless steel appliances. Durable LVP flooring (2021) throughout the main living areas and new carpet in the bedrooms. Laundry includes washer/dryer 2021; refrigerator 2025. Security system installed. Major recent system and structural upgrades for worry-free ownership: HVAC 2023; 40-gal water heater 2023; PEX water lines 2024; new carport roof 2024; new power panel & upgraded wiring 2021; attic insulation & interior paint 2021. Ease of living: Enjoy true low-maintenance, single-level living with HOA exterior care, easy parking under the new carport roof, and modern systems that minimize upkeep and unexpected expenses. The thoughtful updates and security system provide peace of mind and allow you to spend more time enjoying community amenities, nearby lakes, dining, and shopping rather than home maintenance. Location and lifestyle: Conveniently close to Publix, dining, and scenic lakes — ideal for active adults seeking convenience and leisure.

Listing is courtesy of: KELLER WILLIAMS REALTY SMART (863-577-1234)

Listing Agent: Holly Patterson (717-668-9598)

Remarks: Welcome to the next exciting chapter of your life in Lake Ashton, Central Florida’s premier 55+ active-adult community, where this delightful, remarkably private, and fully updated 3-bedroom, 2-bath home awaits your arrival. To the west lies a forested nature preserve that circles to the north and then east, providing absolute privacy on two sides of the oversized lot and creating a serene, natural backdrop to everyday living. The exterior of the house was freshly painted in 2025, and the roof was replaced on December 29, 2022, offering both beauty and peace of mind. As you approach the home, you will immediately notice the greatly expanded paver driveway and the inviting front screened enclosure at the entryway. The home’s gorgeous front door with sidelights offers a gracious welcome and sets the tone for what awaits inside. Stepping through the entry, you will appreciate the lovely porcelain tile flooring, the tasteful paint color palette, chair railing in the dining area, and elegant crown molding that adds a refined touch throughout. Three solar tubes provide abundant natural light, creating a bright and cheerful interior. The kitchen has been thoughtfully updated with all appliances replaced, including a new refrigerator installed in April 2026. The kitchen floor is marble, and all counters are granite, combining durability with timeless style. The second bedroom hosts a Murphey bed. Extending the living space is the impressive 10’ by 26’ tiled veranda, which is fully enclosed and air conditioned, providing comfortable additional living space year-round. Just outside the veranda, a 14’ by 26’ screened and pavered enclosure offers the perfect setting for entertaining guests or simply relaxing while enjoying the peaceful, natural surroundings and the soothing sounds of nature. Residents of Lake Ashton enjoy unmatched amenities, including two championship 18-hole golf courses, a 26,000-square-foot clubhouse, a state-of-the-art health and fitness center, both indoor and outdoor swimming pools, a movie theater, pickleball courts, a bowling alley, and so much more, creating an active and fulfilling lifestyle. This exceptional property offers the perfect blend of comfort, convenience, and community. Schedule your private showing today and experience the very best of Florida living.

Listing is courtesy of: GLOBAL LIFESTYLE LLC (727-455-2709)

Listing Agent: Brad Kirwan (863-280-0390)

Remarks: Welcome to this spacious and recently upgraded home sitting on a rare 0.40-acre corner lot with NO HOA and NO CDD, giving you the freedom and space you’ve been looking for. Major recent improvements include updated HVAC, electrical, and plumbing systems for added peace of mind, along with attractive interior upgrades featuring modern flooring, an updated kitchen with stylish cabinetry and stainless-steel appliances, and refreshed bathrooms with contemporary tile finishes. The oversized lot offers endless possibilities and plenty of room to park your RV, boat, jet ski, work vehicles, or recreational toys worry-free — something hard to find in today’s market. Conveniently located near major supermarkets, restaurants, schools, and main roads for easy commuting, this property is ideal for homeowners seeking space and flexibility or investors looking for a strong opportunity. Schedule your private showing today and discover the value, freedom, and potential this unique property has to offer!

Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)

Listing Agent: Jose Hooker-Gomez (407-272-6986)

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: Under contract-accepting backup offers. It's all about Location! Nestled in between Lake Roy and Lake Summit! Welcome home! The living room and dining area wrap around the kitchen. New Island with breakfast bar that sits 6! The eat in nook area and doors to step out to the screened room and shady backyard, a perfect spot for reading, napping and relaxing. The Primary bedroom is of nice size and the two additional bedrooms are down the hall and have ample closet space. The Inside Utility has access to the side breezeway and the garage. Endless possibilities! Need a seasonal home instead of renting or investment property? This is it! This home's location can’t be beat in the beautiful center of Winter Haven known for the Chain of Lakes for fishing, boating and water sports, Legoland, Shopping, Dining in beautiful Winter Haven. Easy commute to Central Florida Attractions! Call today for more details and showing!

Listing is courtesy of: KELLER WILLIAMS REALTY SMART (863-577-1234)

Listing Agent: Tina Heim, Pa (863-370-1786)

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

Remarks: One or more photo(s) has been virtually staged. Beautifully renovated home in the heart of Winter Haven! Located 2.1 miles to LEGOLAND Florida Resort, this home is ideal as a primary residence, vacation home, or investment opportunity. Conveniently close to shopping, restaurants, and medical facilities, with easy access to everything Winter Haven has to offer. This move-in ready property features updated finishes throughout and offers the perfect combination of comfort and convenience. Enjoy a large fenced backyard with plenty of space for entertaining, pets, or outdoor activities. Don’t miss your chance to own this charming home in a prime location!

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

Listing Agent: Twinkle Robinson (863-860-6645)

Remarks: Don’t miss this incredible opportunity to own a villa in one of Winter Haven’s most sought-after gated golf communities — at an unbeatable price! This 2-bedroom, 2-bathroom villa offers 1,278 sq ft of comfortable Florida living with a peaceful pond view backdrop. The open floor plan flows effortlessly, and the private enclosed Florida room is perfect for year-round entertaining. The generous primary suite features a walk-in shower, and the guest bath includes a tub/shower combo. Why this is a steal: Priced well below comparable properties in the community, Resort-style amenities INCLUDED — 18-hole golf course, tennis, pickleball, pool, fitness center, clubhouse & restaurant, 24-hour manned gate for peace of mind, Pets welcome, Flexible for investors — 6-month minimum lease allowed. Whether you’re looking for your Florida dream home, a seasonal getaway, or a smart rental investment, this property checks every box at a price that won’t last long. Act fast — opportunities like this don’t stay on the market!

Listing is courtesy of: HUMAN TOUCH REAL ESTATE FIRM (863-651-8236)

Listing Agent: Susan Human (863-651-8236)