Winter Haven Homes For Sale & Real Estate - 1041 homes

Remarks: Here is your opportunity to own an immaculate home in the sought after community of Cypresswood Golf and Country Club. Consistently voted the Number 1 Golf Course in the area. This vibrant community has it all. Aside from the fantastic course right out your door, enjoy everything else it has to offer. A wonderful restaurant and Club House where they host live music 3 nights a week and top notch food offerings. An Olympic size pool that was just recently redone along with newly redone tennis courts and pickle ball courts. There is even a fitness center. Take a drive in your golf cart in the evenings and enjoy the natural elements and animals that Central Florida is famous for. Bald Eagles, wild turkey, Sand Cranes are just some of the sights you are likely to see on your ride. Then, come home to your beautifully maintained home that allows for easy entertaining, or peaceful times out on the back screened in patio where you can watch golfers and animals alike. The combination kitchen and family room is second to none. Stainless steel appliances including a new dishwasher for the experienced chef or novice. You can't help enjoying cooking in this home. Second bedroom with it's own ensuite full bath, and two other bedrooms that share a Jack and Jill full bath. You will find storage gallore everywhere you look. Peaceful yard offers privacy and views for days. Come and tour this home today, and you will know that you have found The One!

Listing is courtesy of: REMAX EXPERTS (863-802-5262)

Listing Agent: Stacy Tuttle (863-602-9554)

Remarks: Beautiful 4BR/2BA home in desirable Winter Haven featuring a spacious split floor plan, bright open living areas, and a screened lanai overlooking a large backyard. Roof is only 1 year old with transferable warranty to new owners! The primary suite includes dual vanities and a private bath, while three additional bedrooms allow plenty of space for family, guests, or a home office. Enjoy great curb appeal, a two-car garage, and a peaceful setting with convenient access to shopping, dining, schools, and major roadways. A wonderful opportunity to enjoy comfortable Florida living! Don't miss the opportunity to make this move-in-ready home yours—schedule your private showing today!

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

Listing Agent: Tony Acosta (863-224-5956)

Remarks: Under Construction. New construction home with 1,479 square feet on one-story including 3 bedrooms, 2 baths, and an open living area. Enjoy an open kitchen with Quartz countertops, Samsung stainless steel appliances, pantry, and a spacious counter height bar, fully open to the dining café and gathering room. The living area, laundry room, and baths include luxury wood vinyl plank flooring, with stain-resistant carpet in the bedrooms. Your owner's suite is complete with a walk-in wardrobe and a private en-suite bath with a tiled shower and linen closet. Plus, enjoy a covered lanai, 2-car garage, custom-fit window blinds, architectural shingles, energy-efficient insulation and windows, and a full builder warranty. Please note, virtual tour/photos showcases the home layout; colors and design options in actual home for sale may differ. Furnishings and decor do not convey."

Listing is courtesy of: CAMBRIDGE REALTY OF CENTRAL FL (863-797-4999)

Listing Agent: George Lindsey, Iii (863-797-4999)

Remarks: Fully remodeled 2-bedroom, 1-bath home in the heart of Winter Haven. This move-in-ready property features a new roof, updated electrical and plumbing, and modern finishes throughout. Situated on a spacious lot with no HOA, it offers both comfort and flexibility. Conveniently located near major roads, shopping, dining, schools, and just minutes from downtown Winter Haven and LEGOLAND Florida Resort, making it an excellent option for homeowners or investors.

Listing is courtesy of: AGENT TRUST REALTY CORPORATION (407-251-0669)

Listing Agent: Ed Ospina (407-970-9488)

Remarks: Welcome home to this charming bungalow-style 3-bedroom, 2-bath residence offering comfort, character along with modern updates. Inside, you'll find durable wood-look tile flooring throughout, beautiful granite countertops and a cozy wood-burning fireplace that creates the perfect gathering space. Major improvements include a new roof and windows in 2020, providing added peace of mind. Step outside to enjoy the fully fenced backyard - ideal for pets, play or entertaining. Best of all, there's no HOA, giving you the freedom to truly make this home your own. Conveniently located in the heart of Winter Haven, with easy access to shopping, dining, schools and everything Central Florida has to offer. Schedule your private showing today!

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

Listing Agent: Amanda Plowden (863-224-7088)

Remarks: Pre-Construction. To be built. Discover a home where modern comfort meets effortless style in the beautiful VillaMar community of Winter Haven. Surrounded by scenic lake views and resort-style amenities, this is more than a place to live—it’s a place to truly enjoy life. The Ventura floor plan offers up to 1,562 square feet of thoughtfully designed living space with 4 bedrooms and 2 bathrooms. At the heart of the home, the open-concept layout creates a bright and welcoming atmosphere. The beautifully designed kitchen features a large island with quartz countertops—perfect for gathering, entertaining, or enjoying everyday meals. It flows seamlessly into the spacious great room, where natural light pours in through upgraded windows, creating a warm and airy feel throughout. Your private primary suite, located at the rear of the home, offers a peaceful retreat. Enjoy a spacious walk-in closet, dual sinks, and a walk-in shower designed for both relaxation and ease. There are three other bedrooms and a full bath are tucked away at the front of the home, creating a private and functional space. Built with today’s lifestyle in mind, The Ventura includes smart home features such as a Ring Video Doorbell, Smart Thermostat, Keyless Entry Door Lock, and customizable DEAKO light switches—giving you control and peace of mind at your fingertips. Enjoy the amenities offered in the community with a resort style pool, playground and dog park. Experience the perfect blend of style, convenience, and community living at VillaMar. Your future home is waiting—make The Ventura your own and start creating lasting memories.

Listing is courtesy of: RE/MAX ASSURED (800-393-8600)

Listing Agent: Vilmari Caraballo (407-583-9870)

Remarks: Under Construction. The Aria is one of our one-story floorplans featured in Harmony at Lake Eloise in Winter Haven, Florida. With multiple exteriors to choose from, the Aria is a popular home. Inside this 3-bedroom, 2-bathroom home, you’ll find 1,672 square feet of comfortable living. This all-concrete block constructed, one-story layout optimizes living space with an open concept kitchen overlooking the living area, dining room, and covered lanai. Entertaining is a breeze, as this popular single-family home features a living and dining in the heart of the home, with covered lanai just steps away in your backyard. The spacious kitchen features stainless steel appliances, a convenient island, and walk-in pantry with ample storage. 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. Two additional bedrooms share a second bathroom. This home also features a nice laundry room space with privacy doors and a two-car garage for parking or storage. Like all homes in Harmony at Lake Eloise, the Aria includes 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 Harmony at Lake Eloise. *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. PRICE REDUCED $9,600 FOR QUICK SALE !!!!!!!! Discover this stunning brand-new construction 3-bedroom, 2-bath home with an open living space and a convenient 2-car garage, this move-in-ready gem boasts elegant granite countertops in the kitchen for a touch of luxury and everyday functionality. The bright, airy layout offers three spacious bedrooms, two full baths, and a peaceful setting perfect for relaxing or family life—ideal for first-time buyers or those seeking fresh, contemporary Florida living. Minutes from shopping, dining, parks, and the Chain of Lakes, this serene location combines tranquility with easy access to everything Central Florida offers. Don't miss this pristine new build—schedule your private tour today! All measurements and sizes are deemed to be accurate but not guaranteed; any information contained here that is critical to buyers' purchasing decisions must be verified by the buyers. Private financing is available to qualified buyers.

Listing is courtesy of: DALTON WADE INC (888-668-8283)

Listing Agent: Juan Carrion (863-581-6028)

Remarks: Under contract-accepting backup offers. Short Sale. Charming, move-in ready 3-bed, 2-bath home in a peaceful Winter Haven community. Features an open living/dining layout, updated kitchen with modern finishes, and spacious bedrooms. Enjoy plenty of natural light, a private backyard perfect for gatherings and outdoor living, and an attached 2-car garage. Well-maintained and thoughtfully updated, this home offers both comfort and convenience. Monthly HOA of just $50 includes community maintenance for worry-free living. Close to shopping, dining, schools, and major roadways for easy commuting. Don’t miss this opportunity to own in a quiet, established neighborhood — schedule your showing today!

Listing is courtesy of: WORLD PROPERTIES GROUP (407-574-5920)

Listing Agent: Mona Cherkaoui (407-947-5736)

Remarks: Under contract-accepting backup offers. **MOTIVATED SELLERS** Welcome to the community of Eagle Landing in beautiful SE Winter Haven, Florida. This newer home features 4 Bedrooms/2.5 Bathrooms with a spacious two-story layout that maximizes space and natural light perfect for any lifestyle with Low HOA and NO CDD. The modern kitchen design with Island and Breakfast Bar complete with Granite countertops. The primary bedroom with en-suite bathroom with dual sinks, walk in shower and walk-in closet and 3 additional bedrooms offers plenty of space for a growing family or multi-general family. Needs a little TLC on the inside. The solar panels feature a great savings to help keep your energy cost down. Conveniently located in a quiet neighborhood, this property is ideally situated close to Publix, Legoland, schools and the Winter Haven Chain of Lakes. If you're looking for a modern, quiet neighborhood, this is your chance. Schedule your showing today before it's gone!

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

Listing Agent: Cheryl Brewer (863-224-0045)

Remarks: Under contract-accepting backup offers. Elegant Living in a Prestigious Gated Community Welcome home to this beautifully maintained 3-bedroom, 2-bath residence with a dedicated office, offering the perfect blend of comfort, style, and peace of mind. Nestled in an upscale gated community, this move-in-ready home features a thoughtfully designed split floor plan with durable tile flooring throughout the main living areas and spacious rooms filled with natural light. The private primary suite is a true retreat, featuring dual vanities, a luxurious Jacuzzi soaking tub, and a separate shower, creating the perfect space to unwind after a long day. The versatile office provides an ideal setting for working from home, a library, or hobby room. Major updates provide exceptional value and confidence, including an updated roof (2023), air conditioning system (2026), and water heater (2026), while the Guardian Generac natural gas whole-house generator with battery replaced in 2024 provides reliable backup power and added peace of mind year-round. Step outside to the spacious screened lanai, the perfect extension of your living space. Whether you're enjoying your morning coffee, entertaining friends, or relaxing with a book while taking in the Florida breeze, the screened enclosure allows for year-round outdoor living with comfort and privacy. Enjoy entertaining in the open living spaces or relax in the serene surroundings of this sought-after community. Conveniently located just minutes from LEGOLAND®, shopping, dining, medical facilities, and beautiful parks, this home offers the perfect balance of tranquility and accessibility. Highlights 3 Bedrooms | 2 Bathrooms + Dedicated Office Updated Roof (2023) New A/C System (2026) New Water Heater (2026) Guardian Generac Natural Gas Whole-House Generator (Battery Replaced 2024) Spacious Primary Suite with Jacuzzi Tub & Double Vanities Tile Flooring Throughout Main Living Areas Large Screened Lanai for Year-Round Outdoor Enjoyment Open, Functional Split Floor Plan Upscale Gated Community Minutes from LEGOLAND®, Shopping, Restaurants, Medical Facilities & Parks This exceptional home combines timeless elegance, modern updates, and an unbeatable location—making it the perfect place to call home. From the inviting interior to the peaceful screened lanai and the security of a whole-house generator, every detail has been thoughtfully designed for comfortable Florida living. Schedule your private showing today and discover everything this beautiful home has to offer!

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

Listing Agent: Susan Brown (863-640-5722)

Remarks: Welcome to this beautifully maintained 4-bedroom, 2-bath home built in 2021, offering 1,832 sq ft of comfortable living space in the growing area of Winter Haven.This well-kept residence features a functional and open layout with a spacious kitchen that flows seamlessly into the living and dining areas—perfect for both everyday living and entertaining. Oneof the bedrooms offers flexibility and can easily be used as a home office, ideal for today’s lifestyle needs.The home also includes a dedicated laundry room and generously sized primary bedroom, providing comfortand convenience throughout. Located in a rapidly developing area, a new plaza is currently under construction nearby, adding future value and accessibility to shopping and dining options. Plus, LEGOLAND Florida Resort is approximately 20 minutes away, offering fun and entertainment close to home. Don’t miss the chance to own a newer home in a thriving community!

Listing is courtesy of: DENIZ REALTY PARTNERS LLC (407-704-0780)

Listing Agent: Patricia Schraiber (407-413-1801)

Remarks: Don’t miss this beautifully renovated 2-bedroom, 1-bath home conveniently located near downtown Winter Haven and just minutes from Polk State College. Whether you’re a first-time homebuyer, downsizing, or looking for a great investment property, this home offers exceptional value and is priced to sell. Recent updates provide a fresh, modern feel throughout, making this property truly move-in ready. Enjoy the convenience of a covered carport, a spacious screened patio perfect for relaxing or entertaining, and a large backyard with plenty of room for outdoor activities, pets, or future improvements. With its prime location, updated condition, and strong rental potential, this home is an excellent opportunity for both homeowners and investors alike. Schedule your private showing today before it’s gone! Some photos have been virtually staged

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

Listing Agent: James Wible (813-440-0477)

Remarks: Beautiful property located in a remarkable location! Do not miss out on the opportunity of making this property yours. Discover the perfect blend of comfort and convenience in this beautiful Winter Haven property. Nestled in a peaceful neighborhood, this property offers spacious living areas and a welcoming atmosphere. Enjoy bright living, a well-appointed kitchen, and generously sized bedrooms. Don't miss out- schedule a showing today!

Listing is courtesy of: RIVERA & ASSOCIATES REALTY (813-443-5031)

Listing Agent: Maria Rivera (813-842-7399)

Remarks: Welcome to this FULLY renovated, beautiful and large 3Bed 2bath home in Winter Haven!! Property has been fully renovated to 2026 standards in and out. Fresh pain in and out. Brand new 6" baseboards throughout the home. Crown molding throughout the main living space. Brand new water resistant LVP tile. Pool has been repainted. Walls have been refreshed and smoothened out. Popcorn ceiling through the main home has been sanded down and smoothened. Garage has been given a fresh coating of pain and the floors smoothened. Both Florida rooms have been renovated as well. Roof (2020) A/C (2020) New Water-heater installed (2026) Stainless Steel Samsung Dishwasher (2026) Stainless Steel Samsung Fridge (2026) Stainless Steel Whirlpool Electric Range (2026) Stainless Steel Broan-NuTone Range Hood (2026). Solar Panels are fully owned. Full 3D property walk-through video available upon request. PLEASE NOTE - I AM NOT AVAILABLE ON THE SABBATH/SATURDAYS

Listing is courtesy of: CARDINAL REALTY GROUP, LLC. (305-910-2902)

Listing Agent: Meir Tenenbaum (305-721-7408)

Remarks: Welcome to your private backyard paradise! This beautiful home features two bedrooms, one bath, no HOA, a relaxing jacuzzi spa, functional greenhouses for gardening, storage sheds, irrigation system and a rare, gated private alley at the rear of the property which provides convenient access to your backyard. The property is currently an active plant nursery and the sale includes everything to continue that if you choose. Inside you will find an open layout perfect for comfortable living. Enjoy total peace of mind with newer appliances, windows (2026), electrical wiring (2025), HVAC (2025) and also an indoor laundry space. This property is conveniently located five minutes from downtown Winter Haven, near dining and shopping, close to the Chain of Lakes, Legoland and many parks and outdoor activities. If your looking for the Florida lifestyle then come tour this unique property.

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

Listing Agent: Matthew Hazlett (407-470-6515)

Remarks: Under contract-accepting backup offers. 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. 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: NO CDD fees! Welcome to Peach Crossings, Winter Haven’s newest community! This brand-new three-bedroom, two-bathroom home is designed for both comfort and style. The kitchen is the heart of the home, offering ample counter space—perfect for meal prep and entertaining. It comes fully equipped with Whirlpool stainless steel appliances, including a refrigerator, stove, dishwasher, and microwave—all included at no extra cost! Granite countertops and modern cabinetry provide a classic, elegant touch. This home also features high ceilings, enhancing the open and airy feel throughout the living spaces. Enjoy the outdoors year-round with the covered patio, a great spot for dining, relaxing, and taking in the fresh air—made even better by the privacy of having no rear neighbors and a beautiful pond view. This home is packed with energy-efficient features, such as double-pane windows, a programmable thermostat, coach lighting, and a Wi-Fi-enabled garage door opener for added convenience. A mudroom off the garage offers the perfect drop zone for shoes, bags, and coats, making daily routines easier. Located next to the laundry room, this space helps keep everything organized and clutter-free. Situated in Polk County, Peach Crossings offers a balance of peaceful lake life and easy access to shopping, dining, and major attractions. Families will love the top-rated Polk County schools, and the community features a playground and picnic area for all to enjoy. Don’t miss out on this incredible opportunity—schedule your tour today!

Listing is courtesy of: LGI REALTY- FLORIDA, LLC (904-449-3938)

Listing Agent: Gayle Van Wagenen (904-449-3938)

Remarks: Under Construction. BELOW MARKET INTEREST RATES with use of Seller's Preferred Lender. Indigo - Check out the Indigo, a spacious two-story, 5-bedroom, 3-bathroom, 2-car garage home perfect for growing families or hosting guests. Enter the impressive foyer with soaring ceilings that creates an immediate sense of openness. From the foyer, the home effortlessly flows into the main living areas and kitchen. With quartz countertops throughout, stainless-steel appliances and a smart thermostat for energy efficient climate control, the Indigo brings all the things that matter together. The downstairs guest suite and bathroom are tucked away for added seclusion, while the open concept living space is perfect for entertaining. Upstairs, you'll find a generously sized recreation space, ideal for family time or unwinding. The owner's suite is a true sanctuary, featuring a walk-in shower, double vanities, and a spacious walk-in closet. A laundry room with a new washer and dryer is just off the owner’s suite, conveniently located near the 3 additional bedrooms and full bathroom. The Indigo is as functional as it is stylish, providing the perfect balance of comfort and modern living. Close to it all, Villa Mar places you near the natural beauty of the Winter Haven Chain of Lakes, the charm of downtown Winter Haven, and family fun at LEGOLAND® Florida Resort. Back at home, residents enjoy community amenities including a pool, dog park, playground, and walking trails. 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. Indigo BELOW MARKET INTEREST RATES with use of Seller's Preferred Lender. Check out the Indigo, a spacious two-story, 5-bedroom, 3-bathroom, 2-car garage home perfect for growing families or hosting guests. Enter the impressive foyer with soaring ceilings that creates an immediate sense of openness. From the foyer, the home effortlessly flows into the main living areas and kitchen. With quartz countertops throughout, stainless-steel appliances and a smart thermostat for energy efficient climate control, the Indigo brings all the things that matter together. The downstairs guest suite and bathroom are tucked away for added seclusion, while the open concept living space is perfect for entertaining. Upstairs, you'll find a generously sized recreation space, ideal for family time or unwinding. The owner's suite is a true sanctuary, featuring a walk-in shower, double vanities, and a spacious walk-in closet. A laundry room with a new washer and dryer is just off the owner’s suite, conveniently located near the 3 additional bedrooms and full bathroom. The Indigo is as functional as it is stylish, providing the perfect balance of comfort and modern living. Close to it all, Villa Mar places you near the natural beauty of the Winter Haven Chain of Lakes, the charm of downtown Winter Haven, and family fun at LEGOLAND® Florida Resort. Back at home, residents enjoy community amenities including a pool, dog park, playground, and walking trails.  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)