Winter Haven Homes For Sale & Real Estate - 803 homes

Remarks: Hidden gem with upgrades you won’t expect! First-floor condo for easy access and numerous updates throughout. The kitchen features a new backsplash, new sink and faucet, freshly painted cabinets, and newer appliances, including the refrigerator and dishwasher. A new water heater adds additional peace of mind. Both bathrooms have been updated with new vanities, faucets, and tile backsplashes. Custom wood shelving has been installed throughout the home—no wire shelving—along with custom closet organizers in both bedrooms. The spacious primary bedroom features beautiful plantation shutters. Stylish barn doors enclose the laundry area with a washer and dryer, and the hall closet. Covered parking included. Situated on scenic Lake Howard, part of the famous Winter Haven Chain of Lakes, this community offers boat dock access. Residents also enjoy a sparkling pool, gazebo with grilling area, shuffleboard courts, and a quiet, secure atmosphere. Even better, the HOA covers cable, internet, water, sewer, trash, exterior maintenance, and lawn care—you only pay for electricity. Truly affordable, maintenance-free Florida living.

Listing is courtesy of: VILLAGE REALTY OF WINTER HAVEN (863-299-6767)

Listing Agent: Nancy Cini (727-612-0375)

Remarks: One or more photo(s) has been virtually staged. This 3 bedroom, 2 bathroom home is located in Idylwild Heights a charming residential subdivision nestled in Winter Haven, Florida. Winter Haven is a picturesque city celebrated for its chain of lakes and friendly community atmosphere. Known for its welcoming ambiance and established neighborhood feel, Idylwild Heights offers residents an appealing blend of suburban tranquility and convenient urban access.

Listing is courtesy of: CENTURY 21 WOLF'S CROSSING REALTY (407-449-0000)

Listing Agent: Lucy Martinez (863-521-4156)

Remarks: Under contract-accepting backup offers. Beautiful 4-bedroom, 2-bath home in Magnolia Preserve with an open-concept layout, high ceilings, and a large backyard overlooking a pond with a fountain. The spacious great room features wood-look flooring, recessed lighting, and a ceiling fan, while the kitchen offers a large breakfast bar, ample cabinetry, stainless steel appliances, and generous counter space. The primary suite includes a walk-in closet and an en-suite bath with dual sinks, garden tub, and separate shower. Enjoy the covered rear patio, interior laundry room, and 2-car garage. Move-in ready and conveniently located near shopping, dining, and major roadways.

Listing is courtesy of: LOKATION (954-545-5583)

Listing Agent: Jeremy Harper, Pa (863-288-0886)

Remarks: This move-in-ready, three-bedroom, two-bathroom home is located in the sought-after Lake Dexter Woods community. The residence features a functional layout designed for modern comfort and style, highlighted by an attached one-car garage and low-maintenance tile flooring throughout the entire home. The updated kitchen serves as a stylish centerpiece, equipped with beautiful granite countertops and sleek stainless-steel appliances. Outside, you can relax and enjoy the fresh air from your private porch and patio, which overlooks a fully fenced-in backyard, providing a secure space for outdoor entertaining or pets. The location offers a perfect blend of comfort and convenience, situated near top-rated schools, multiple grocery stores, and popular local attractions. Residents can enjoy a resort-style lifestyle with access to premium community amenities, including sparkling pools, tennis/pickleball courts, and more.

Listing is courtesy of: ENTERA REALTY LLC (888-216-6364)

Listing Agent: Robert Salmons (888-216-6364)

Remarks: Under contract-accepting backup offers. Back on market, buyer financing fell through. Their loss, your gain! Stunning ranch modern transformation that will take your breath away! Welcome to this 2019 impeccably redesigned modern rustic 4 bed/2 bath retreat on fenced one-third acre lot on cul-de-sac with seamless indoor-outdoor entertaining. Homeownership pride from the front curb to the back fence! As you approach, you are greeted by a New sprawling 13’x46’ covered front porch with ample space for hosting gatherings while you enjoy the beautifully landscaped front yard with extended driveway that includes a tall RV cover. Step inside to the farmhouse chic living room that seamlessly flows through the sliding barn doors into the heart of the home, the custom designed kitchen, featuring wood beam tray ceiling with pendent lighting, white cabinets, butcher block counter, SS appliances including smart fridge w/tv & Alexa, large island with farm sink and breakfast bar, & barn door pantry with luxury vinyl plank flooring throughout and fresh interior paint. Adjacent to the kitchen on one side is the laundry room with built in cabinets that leads to the back yard, and the other side to the spacious family room, with every inch thoughtfully styled that create a warm, inviting atmosphere. Included is the entertainment center with the wide screen tv. The main bedroom has spacious on-suite bathroom that features beadboard panels & stone backsplash, dark matching accent trim, double sinks, garden tub, separate rain head shower with glass sliding door, and storage closet. The 2, 3 ,& 4th bedroom share a convenient 2nd bathroom with shower/tub. The property also includes a large storage shed with electric— perfect for tools, hobbies, or extra storage. Situated in a peaceful area of Winter Haven, this home offers the best of both worlds: quiet suburban living with easy access to shopping, dining, and major highways for commuting throughout Central Florida. Don’t miss your chance to own this move-in-ready home with modern updates, generous space, and outdoor charm — all with no HOA!

Listing is courtesy of: KELLER WILLIAMS HERITAGE REALTY (407-862-9700)

Listing Agent: Sheryl Manche (386-882-2121)

Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Charming 2-bedroom, 1.5-bath home located in Winter Haven presenting a great opportunity for first-time home buyers or investors. This property features a functional layout with comfortable living spaces and a practical design suited for everyday living. The home sits on a generously sized lot, providing plenty of outdoor space for entertaining, gardening, or future improvements. Conveniently located near local schools, shopping, dining, and major roadways, this property provides both accessibility and convenience. With strong potential as a starter home, rental property, or investment opportunity, this home is a great option for buyers looking to enter the market or expand their portfolio in the growing Winter Haven area.

Listing is courtesy of: IMPACT REALTY TAMPA BAY (813-321-1200)

Listing Agent: Jay Patel (863-399-5820)

Remarks: Under Construction. BELOW MARKET INTEREST RATES with use of Seller's Preferred Lender. The Turquesa is the ultimate family haven, a two-story home featuring 4 bedrooms, 2.5 bathrooms and a private 2-car garage. This home offers an open concept living space designed for both relaxation and entertainment. The half bathroom off the foyer ensures every guest feels at home while the extended foyer opens to the main living and dining area. Featuring luxury vinyl plank flooring and convenient indoor-outdoor living with a lanai through sliding glass doors, it’s a haven of comfort and style perfect for gatherings. The kitchen includes stunning quartz countertops and sleek stainless-steel appliances. Enjoy the spacious upstairs recreation room and the convenience of a laundry room just steps away from the bedrooms. Did we mention the brand-new washer and dryer? The owner's suite is a secluded retreat with oversized his-and-her walk-in closets, dual vanity and a walk-in shower. Completing this expansive home is the smart thermostat with voice control and professionally designed landscaping, this is truly the epitome of family-friendly luxury! Contact or make an appointment for more details on interest rates. Just off US-27 with quick access to I-17, Villa Mar puts you close to local hotspots, and everything that makes Central Florida shine. Discover Winter Haven’s Chain of Lakes, explore the historic downtown district, or enjoy a fun-filled day with the family at LEGOLAND® Florida Resort. At Villa Mar, you’ll enjoy a fresh approach to relaxed living, with everyday essentials and local favorites right around the corner. Images shown are for illustrative purposes only and may differ from actual home. Completion date subject to change. Contact or make an appointment for more details on interest rates.

Listing is courtesy of: CASA FRESCA REALTY (813-343-4383)

Listing Agent: Michael Human (813-343-4383)

Remarks: Under Construction. BELOW MARKET INTEREST RATES with use of Seller's Preferred Lender. Meet the Esperanza, a single-story, multi-generational home designed for modern living with flexibility and comfort. This 4-bedroom, 3-bathroom, 2-car garage home features a separate multi-gen suite with its own bathroom and kitchenette, ideal for extended family or guests. The spacious layout offers distinct areas for gathering and relaxing, including an open-concept living and dining space paired with a thoughtfully designed kitchen featuring quartz countertops, stainless steel appliances, and smart home technology for everyday convenience. With smart design and stylish touches throughout, the Esperanza balances independence and togetherness, providing room to grow—together. Just off US-27 with quick access to I-17, Villa Mar puts you close to local hotspots, and everything that makes Central Florida shine. Discover Winter Haven’s Chain of Lakes, explore the historic downtown district, or enjoy a fun-filled day with the family at LEGOLAND® Florida Resort. At Villa Mar, you’ll enjoy a fresh approach to relaxed living, with everyday essentials and local favorites right around the corner. Images shown are for illustrative purposes only and may differ from actual home. Completion date subject to change. Contact or make an appointment for more details on interest rates.

Listing is courtesy of: CASA FRESCA REALTY (813-343-4383)

Listing Agent: Michael Human (813-343-4383)

Remarks: Under contract-accepting backup offers. Nestled within the peaceful community of Fox Ridge, this exquisite 3-bedroom, 2-bathroom home serves as a sanctuary for those in search of tranquility combined with modern amenities. As you step inside, you'll be greeted by bright, fresh interiors enhanced by newly installed luxury vinyl plank flooring throughout the main living areas. The kitchen, a chef's delight, features stainless steel appliances, sleek white cabinets, and elegant granite countertops. The generous primary suite includes dual closets and a convenient ensuite bathroom for added comfort. An expansive sunroom beckons you to unwind throughout the year, while the private, fenced-in backyard is ideal for gatherings or enjoying a peaceful afternoon. This home also features a new ROOF, a new HVAC system, a two-car garage, and updated lighting and fixtures throughout, ensuring it's move-in ready. Don’t miss the chance to explore this charming retreat today!

Listing is courtesy of: URBAN CORE REALTY (813-418-0207)

Listing Agent: Monica Dudas (813-418-0207)

Remarks: Welcome to 6617 Westchester Dr NE in Winter Haven, located in the highly desirable 55+ no pet community of Lake 'n Golf Estates. This spacious and well maintained home has been lovingly owned by the same family since 1992 and offers comfort, convenience, and a true Florida lifestyle. Inside, you’ll find a bright and inviting layout with generous living spaces, engineered wood flooring in the main living areas and bedrooms, and porcelain tiles in the kitchen, bathrooms, and hallway. The home also features an inside laundry room for added ease. It will be sold mostly furnished, making it a perfect move in ready option for seasonal or full time living. A standout feature is the enclosed front Florida room, complete with its own mini/split system for heating and cooling, along with updated windows, blinds, porcelain flooring, a ceiling fan, and a hide-a-bed, creating a comfortable and versatile bonus space year round. This home has been thoughtfully updated over time, including a new roof (2023), updated heat pump and ductwork, a membrane roof over the sunroom and new siding (2025). Additional improvements include updated windows and doors, enhanced plumbing throughout (including replacement of gray piping, water heater, fixtures, and disposal) and upgraded appliances such as a new stove (2025) and microwave (2024). Outside, you’ll appreciate the large carport, a beautifully finished driveway, and additional space for golf cart parking, along with a cement golf cart path for added convenience. With NO REAR neighbors, the property offers a private and peaceful setting. Additional included items such as select furnishings, a leather recliner, beds, TVs, ceiling fans, blinds, and an outside antenna add even more value and convenience. Residents of Lake 'n Golf Estates enjoy a vibrant and active lifestyle with access to lake Henry, a clubhouse, pool, shuffleboard courts, and a variety of social activities. Conveniently located near shopping, dining, and everyday amenities, this community offers both relaxation and accessibility. Don’t miss your opportunity to own a beautifully updated and spacious home in one of Winter Haven’s most welcoming 55+ communities, schedule your private showing today!

Listing is courtesy of: RE/MAX HERITAGE PROFESSIONALS (863-256-2188)

Listing Agent: Patricia De Graaff, Llc (863-307-0061)

Remarks: Welcome Home to Orchid Springs Village! Step into comfort with this inviting 1-bedroom, 1.5-bath condo located on the second floor of the peaceful Orchid Springs 55+ community. Surrounded by mature landscaping, this residence offers a quiet and comfortable setting, ideal for those looking to enjoy a relaxed Florida lifestyle. You’ll appreciate being conveniently close to shopping, dining, medical facilities, Winter Haven Hospital, US Hwy 27, and I-4. The monthly HOA fee covers water, sewer, trash, natural gas, lawn maintenance, grounds upkeep, and use of the community room, allowing for easy, maintenance-free living. An assigned parking space is included, and one pet is welcome with HOA approval (size and breed restrictions apply). Buyer approval is also required by the HOA. Whether you’re searching for a year-round home or a seasonal retreat, this well-maintained condo at Orchid Springs Village offers comfort, convenience, and a welcoming community atmosphere.

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

Listing Agent: Scott Cohara (407-398-9554)

Remarks: One or more photo(s) has been virtually staged. This expansive two-story Columbus has a well-designed layout, featuring a first floor dedicated to shared living and entertaining. The open concept design seamlessly connects the kitchen, dining room and family room, with a patio extending the interior space outdoors. Upstairs, a spacious loft separates the three secondary bedrooms from the serene owner's suite. Completing the home is a convenient two-car garage. Peace Creek Reserve is a masterplan community of new single-family homes with a beautiful natural creek. Winter Haven is the chain of lakes city, with over 26 linked together by canal. There are lots of shops, restaurants, 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: Very well kept home on your own lot. No lot rent here! Low HOA of only $65 a month. Garden Grove Oaks is a well-kept and managed over 55 park in a great location in SE Winter Haven. Home has 2 bedrooms and 2 full bathrooms. Kitchen and dining area have tons of cabinets and storage for all your dishes and cookware and includes a closet pantry. There is a wet bar in the dining area with a small sink, open shelves and cabinet storage underneath. The opposite side of the dining room has a built-in china cabinet. Main bedroom is a great size with a walk-in closet and small bathroom with tub and tiled shower. Second bedroom has door opening to nice-sized bathroom with large sink and cabinets and a shower/tub combination. Home has a membrane roof that was installed in spring of 2014. York air conditioner is 8-9 years old. Nice large laundry room has Bosch washer and dryer. Back screened porch is always cool! HOA fee includes use of the clubhouse with many activities planned every month. There is a billiard room, card and game room with library and puzzles to check out, large event area, and great kitchen. Huge heated pool and spa for all residents and their guests. There is also a shuffleboard court. HOA is an award-winning association. Community is close to a Super Walmart and grocery stores as well as shopping and restaurants. Only minutes to Hwy. 27! Winter Haven is famous for its Chain of Lakes! Where else can you find all of this for only $140,000? Please make an appointment to see this great home today!

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

Listing Agent: Peggy Lewellen (863-412-7692)

Remarks: Under Construction. his BEATIFUL ELSTON II Model home has 4 bedrooms, 2.5 baths & a 2-car garage-2305 SqFt. NEWLY UPGRADED! Large 2-STORY open floor plan with spacious great room & kitchen to entertain & enjoy the company of your guests. All bedrooms & laundry located on the 2nd floor. 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 from your smart phone, or through the smart panel interface. Your Smart Home comes with Alarm app, Kwikset Smart Front Lock, IQ Panel, Video Doorbell, Z-Wave Thermostat, and a DEAKO Smart 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. Introducing the Harper floorplan at Villamar, where every square foot is put to use with sophistication and comfort. Inside this 4 bedroom, 2 bathroom home, you’ll find 1,665 square feet of comfortable living. This meticulously designed residence combines modern convenience with timeless elegance, showcasing granite and tile floors throughout. As you step inside, you are greeted by an inviting foyer that leads you into the heart of the home. The open-concept layout seamlessly connects the living room, dining area, and kitchen, creating a perfect space for entertaining family and friends. The spacious living room features abundant natural light, thanks to large windows that provide picturesque views of the surrounding landscape. With ample room for seating, it's an ideal spot for relaxation and gatherings. The chef's kitchen is a true highlight, boasting granite countertops, sleek stainless steel appliances, and an oversized island with a breakfast bar. Whether you're preparing a casual meal or hosting a formal dinner, this kitchen is well-equipped to meet your culinary needs. The four generously sized bedrooms has flexibility for various lifestyles. The primary suite is a tranquil retreat, featuring a private ensuite bathroom with dual sinks, a separate shower, and a walk-in closet. The remaining three bedrooms share one well-appointed bathroom, making morning routines a breeze. Like all homes in Villamar, the Harper 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. Whether you're seeking a peaceful family retreat or a stylish place to call your own, this home is sure to meet your every need. 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: This move-in-ready 3-bedroom, 2-bath home features fresh interior paint, new carpet, and new LVP flooring throughout. The large living room showcases vaulted ceilings, creating an open and airy feel, while the kitchen offers a convenient breakfast bar. Step outside to enjoy a private yard with a patio—perfect for relaxing or entertaining.

Listing is courtesy of: OFFERPAD BROKERAGE FL, LLC (813-534-6326)

Listing Agent: Rob Jones (844-448-0749)

Remarks: You'll definitely want to check out this beautiful, like-new property! The zero entry resort style community pool and playground overlooks one of the many beautiful lakes in Winter Haven. Villamar is a wonderful community close to a top rated Elementary School. Enjoy the privacy of this lot, as it does not have rear neighbors, but instead overlooks a quaint pond and conservatory area! Make sure to schedule your showing today!

Listing is courtesy of: VALOR REALTY SERVICES LLC (407-668-2448)

Listing Agent: Marian Benson (954-205-3075)

Remarks: Under contract-accepting backup offers. **WONDERFUL PRICE IMPROVEMENT on this lovely lakefront, pool home, nestled in the charming, gated, SE community of Ruby Lake. This beautiful and spacious 4-bedroom, 3-bath provides the perfect blend of elegance and comfort, with views of Ruby Lake from almost every room in the home. Known for being two of the most sought-after lakes for water skiing and fishing, Ruby Lake and Lake Bess are connected by a canal allowing for plenty of space for all water activities. Both feature slalom courses and jump ramps, delivering high excitement and endless entertainment! Perched on gentle elevation, this property boasts breathtaking sunsets and lush scenery, while also offering some of the best views in this quaint and walkable neighborhood. The elegant entryway leads to the formal living and dining area, with spectacular views of the pool and lake. High ceilings throughout the home, enter the open-concept kitchen, breakfast area, and family room that also showcase the incredible views through an abundance of windows. Savor the gentle breezes flowing through open windows and doors at the back of the home, as the calming sounds of the pool waterfall invite you to unwind. The spacious kitchen features plenty of cabinets, solid surface countertops, a generously sized closet pantry, and a welcoming layout, making it easy for everyone to participate in gatherings. The Main Bedroom serves as a private retreat offering the same stunning pool and lake views, featuring high ceilings, two walk-in closets, and a luxurious en-suite bath with a shower, tub, and dual vanities. A true split floor plan featuring spacious and inviting 2nd and 3rd bedrooms, with generously sized closets, wonderful views and a nicely appointed guest bath in between each. The 4th bedroom is currently being used as an office and is conveniently located near the full pool bath allowing privacy for the whole family and guests. The backyard is a true oasis, boasting a screened-in pool, an outdoor kitchen added in 2016, a relaxing sandy beach area, lush gardens, a dock with a boat lift built in 2020, and irrigation conveniently sourced from the lake. The dock also features a cozy sitting area, perfect for enjoying sunsets or catching the Legoland fireworks. Both the front and back yards create a tropical paradise, filled with majestic Palms, Oaks, Crepe Myrtles, and exotic plants that provide a park-like setting, reduce energy costs, and enhance the serene beauty. Park the car, step into the kitchen from the oversized two-car garage and enjoy the convenience of a spacious laundry room with storage just steps away. The large driveway offers plenty of space for family and guest parking. Relax with peace of mind knowing the roof was updated in 2022, new HVAC March 2026, and the hot water heater is newer. Enjoy this wonderful community and its proximity to all things Central Florida to include nearby theme parks, the Winter Haven Chain of Lakes, known as the "Water Ski Capital of the World", local shopping and restaurants and nearby beaches. Come home to this truly delightful and serene retreat—call today to schedule your private showing!

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

Listing Agent: Carmen Padilla (863-968-4233)

Remarks: *NEW ON MARKET*POND VIEW OWN YOUR. *55 PLUS COMMUNITY* YOU OWN THE LAND .* NO LOT RENT* PRICED TO SELL.THIS MOVE IN READY HOME IS LOCATED IN THE VILLAGE PARK COMMUNITY .* FURNITURE CAN BE INLCUDED* THIS 2BR - 2 BATH HAS AN OPEN DESIGN WITH LOADS OF STORAGE IN THE KITCHEN AS WELL AS THE OVERSIZED BATHROOMS. YOU HAVE A BREAKFAST EATING COUNTER UNLESS OF COURSE YOU WANT TO RELAX ON THE SCREEN ENCLOSED PORCH OVERLOOKING THE MORNING SUNRISE WITH A GREAT WATERVIEW. RELAX AND WATCH THE BIRDS AND WILDLIFE, RATHER THAN LOOKING INTO A NEIGHBORS HOME. THIS COMMUNITY HOA IS ONLY $55 MONTHLY AND HAS A CLUBHOUSE, POOL, SHUFFLEBOARD AND SCHEDULED WEEKLY ACTIVITIES. DON'T WAIT, THIS WON'T BE ON THE MARKET LONG.

Listing is courtesy of: LINCOLN MADISON REAL ESTATE LLC (863-521-0549)

Listing Agent: Chris Davies (863-279-0013)

Remarks: One or more photo(s) has been virtually staged. Welcome to this stunning Dream Finders Poinciana floorplan, located in the highly sought-after community of Willowbrook near a beautiful golf course in Winter Haven, FL. This spacious 4-bedroom, 3-bath home offers 2,110 square feet of living space, and providing excellent curb appeal in it's elevation. Inside, you'll find gorgeous white cabinets complemented by sleek quartz countertops in the kitchen, creating a modern, bright atmosphere. Tile flooring runs throughout the wet and common areas, offering durability and easy maintenance. The open layout is perfect for family gatherings and entertaining guests.

Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)

Listing Agent: Nancy Pruitt, Pa (352-552-7574)