Winter Haven Single Family Homes For Sale - 748 homes

Remarks: Welcome to TRADITIONS, an active 55+ gated community located in the heart of the state on Lake Ruby. From swimming laps in the olympic size pool, casting a line at the lake, swinging a pickleball racquet or utilizing the fitness room and scheduled classes, there is plenty to do to stay in shape. If you prefer a more relaxed day, the clubhouse provides plenty of social spaces for card games, crafting, puzzles and reading a book. The community has planned monthly activities, they even plan a yearly community cruise if that's your vibe. You don't need to leave the community to find something to do, however; Disney and Universal Studios are nearby and you can reach either coast in less than two hours. The community is close to shopping (Publix coming soon), medical facilities, Legoland and the quaint downtown area of Winter Haven with boutique shops and local restaurants. This community is truly the ultimate 55+ lifestyle. The monthly dues include: community amenities, Spectrum cable and internet, lawn maintenance, common area maintenance, and exterior paining every 8 years. Now for the house: This is a Kennedy model floorplan, one of the most sought after in this community. It is a SHOW STOPPER from top to bottom and these Sellers have executed great care during their ownership. You will appreciate some of the additions they have made such as the extended rear screened lanai with Coolaroo shades and a motorized hurricane shutter. They also extended a paver BBQ area for those who like to grill. They added overhead storage racks in the garage and if you are an angler you will appreciate the storage system for the fishing poles! They have also added a motorized screen door for the days that you want to tinker in the garage and keep the bugs out. The exterior was just painted in 2025. The lawn is manicured with professional landscape edged flower beds and best of all the grass is maintained by the HOA. Step inside the front door to be instantly impressed with the high ceilings. The space is open enough for great entertaining but also offers space to spread out when needed. Ceramic tile in all the wet areas and living spaces with 5 inch baseboards and crown molding give the feeling of luxury. Recessed lighting, pendant lights as well as good window placement bring good lighting into the space. The kitchen is spectacular. 42 inch upper cabinets, quartz counters, walk in pantry and preparation island make the space functional for the chef and easy to entertain in. There are three dining space choices: formal dining area, breakfast nook and a breakfast bar providing with plenty of seating. The living room flows perfectly from the triple sliding door onto the lanai. The wall mounted TV's convey. The floorplan also offers a triple split bedroom plan. The primary bedroom offers an ensuite and the walk in closet has custom built in shelving. The ensuite has dual sinks, private commode room, linen closet and soaking tub. The walk in shower has no step and has nice glass doors. The 2nd and 3rd bedrooms share a guest bath with dual sinks and the 4th bedroom has a private ensuite. You truly have to see this home to appreciate its flow, style, tidiness and all the features that make this place a HOME! If 55+ living in Florida is what you have been dreaming of, you just found it! Come make some new Traditions!

Listing is courtesy of: DREAM REALTY GROUP (863-450-7973)

Listing Agent: Christie Weeks (863-450-7973)

Remarks: Under contract-accepting backup offers. ****PRICE IMPROVEMENT**** This home presents an exceptional opportunity to own in one of Winter Haven’s most desirable 55+ communities. This beautifully maintained 2-bedroom, 2-bath home offers the perfect blend of comfort, privacy, and effortless Florida living. Step inside to a bright, open-concept layout where the living and dining areas flow seamlessly into the kitchen—creating an inviting space ideal for both everyday living and entertaining. Large windows flood the home with natural light, highlighting the clean, well-kept finishes throughout. What truly sets this property apart is the oversized fenced backyard and extended pavered screened-in porch—a rare find in the community. This private outdoor retreat provides unmatched space and flexibility. Whether you have pets, enjoy gardening, or simply value extra room to unwind, this backyard delivers both privacy and possibility. The expanded screened porch feels like a true extension of the home—perfect for outdoor dining, hosting guests, or enjoying peaceful mornings and relaxing evenings in comfort. The primary suite offers a tranquil escape, complete with a walk-in closet and glass-enclosed shower. A spacious secondary bedroom provides versatility for guests, a home office, or hobby space. Thoughtfully designed and move-in ready, this home allows for low-maintenance living so you can fully enjoy the lifestyle you deserve. Residents of Traditions at Lake Ruby enjoy resort-style amenities including a 19,000-square-foot clubhouse, heated pool and spa, fitness center, tennis and pickleball courts, scenic walking trails, and private lake access to Lake Ruby—all just minutes from shopping, dining, and medical facilities. With its recent price improvement, exceptional outdoor space, and prime location, this home stands out as one of the best values in the community. Schedule your private showing today before this opportunity is gone.

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

Listing Agent: James Barris (863-258-6321)

Remarks: Quick Move-in! Introducing Villa Mar in Winter Haven, Florida. Master-planned amenities including a pool with cabana that is walking distance from your home, a playground, and shaded seating area. Highway 27, less than 10 minutes away, has everything you are looking for. Grocery stores, movie theaters, shopping centers, golf courses, restaurants, and so much more. The Windermere single-family home is where you want to be. Step in from the 2-car garage and enjoy the good life. Find it in the large family room, where smiling faces greet you and delicious smells fill the gourmet kitchen. Share stories around the island or outside on the lanai. The 1st floor also features a study. Upstairs, 3 bedrooms and a full bath provide privacy while a loft adds extra entertaining space. Your deluxe owner’s suite includes double vanities, a seated shower and a walk-in closet, making The Windermere can’t-miss. All Ryan Homes now include WIFI-enabled garage opener and Ecobee thermostat. **Closing cost assistance is available with use of Builder’s affiliated lender**. DISCLAIMER: Prices, financing, promotion, and offers subject to change without notice. Offer valid on new sales only. See Community Sales and Marketing Representative for details. Promotions cannot be combined with any other offer. All uploaded photos are stock photos of this floor plan. Actual home may differ from photos.

Listing is courtesy of: MALTBIE REALTY GROUP (813-819-5255)

Listing Agent: Bill Maltbie (813-819-5255)

Remarks: Cozy 3-Bed, 3-Bath Home Near Downtown Winter Haven Welcome to your next chapter in the heart of Winter Haven. This warm and inviting 3-bedroom, 3-bathroom home offers the perfect blend of comfort, convenience, and Florida charm. Just minutes from downtown, you’ll enjoy easy access to local shops, dining, parks, and community events while still coming home to a peaceful, cozy retreat. Step inside to discover a spacious layout designed for both relaxation and connection. Whether you’re hosting gatherings or enjoying quiet evenings in, this home offers plenty of room for your family to grow and make memories. One of the standout perks of this location is the proximity to beautiful Lake Silver. Spend your weekends enjoying water sports, lakeside strolls, or taking in the festive fireworks that light up the sky throughout the year. It’s a lifestyle that blends everyday comfort with a touch of lakeside magic. This home is ready to welcome its new family with open arms—and plenty of space.

Listing is courtesy of: COLDWELL BANKER REALTY (407-333-8088)

Listing Agent: Vanessa Marshall (321-377-3606)

Remarks: **SELLERS OFFERING $5,000 CLOSING COST CREDIT** 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. 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: PRICE IMPROVEMENT! Welcome to this super spacious 3-bedroom, 2-bath home located in Lucerne Park Reserve in Winter Haven. Built in 2020, this home offers a modern split floorplan that provides privacy and functionality, perfect for everyday living or entertaining. The open layout creates a bright and airy feel throughout, with generous room sizes and excellent flow. Furniture is negotiable, making this a flexible move-in-ready opportunity for buyers. Enjoy outdoor living with a screened-in patio/lanai overlooking a fully fenced backyard—ideal for pets, play, or relaxing in privacy. Situated in a well-maintained community featuring a pool, playground, and clubhouse, this home offers both comfort and convenience. Enjoy the benefits of newer construction paired with desirable neighborhood amenities, all just minutes from shopping, dining, and major roadways. A great opportunity to own a nearly new home in a fantastic Winter Haven location.

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

Listing Agent: Harold Baker (863-604-6272)

Remarks: Investor Opportunity with Value-Add Potential in Winter Haven! Welcome to 112 Sandburg Ln a 3 bedroom, 2 bathroom block home on a concrete slab offering a solid foundation for investors or renovation buyers seeking a value-add project. The property features durable block construction, a practical floor plan, and ample opportunity for updates to improve functionality and overall appeal. This home is well-suited for a fix-and-flip or long-term rental strategy, with renovation potential that allows the next owner to maximize value. The layout provides flexibility for interior improvements, while the slab foundation and block construction support long-term durability and ease of maintenance. Conveniently located near shopping, dining, schools, and major roadways, the property has strong market appeal once renovated. Whether you're an experienced investor or a buyer looking for a renovation project, this property presents a compelling opportunity in the Winter Haven area. Property requires updates.

Listing is courtesy of: BEYCOME OF FLORIDA LLC (804-656-5007)

Listing Agent: Steven Koleno (804-656-5007)

Remarks: The two-story Atlanta Plan has the “WOW-Factor” with four bedrooms, two and a half baths, loft and a two-car garage. This exquisite home offers an open floor plan with great room, dining room, and kitchen with large island. The kitchen features ample counter space, and generous pantry. The casual dining area allows outdoor access to a covered lanai via sliding glass doors. The second floor includes an owner's retreat featuring an owner's bath with large walk-in shower, dual vanity, and spacious walk-in closet. Three additional bedrooms, a bathroom, a spacious loft, and laundry room finish off this beautiful home. This home comes fully equipped with Everything Included Features like new appliances, solid surface countertops throughout and oversized tile flooring in the wet areas. 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: EXP REALTY LLC (888-883-8509)

Listing Agent: Omar Andreasen (407-883-2989)

Remarks: Price reduction! Bring your buyers. Motivated seller brings added opportunity on this inviting four-bedroom, two-bathroom single family home in Winter Haven. Featuring a desirable split floor plan, this home offers privacy comfort, space, and functionality for the primary suite while maintaining an easy, natural flow throughout the main living areas perfect for everyday living and entertaining. The spacious primary suite serves as a relaxing retreat, featuring, a walk-in closet, a soaker tub, and a separate shower. Generously sized secondary bedrooms present flexibility for guests, a home office, or future needs. Enjoy warm and welcoming living spaces that lead to a screened patio, ideal for morning coffee or evening gatherings, all overlooking a fenced backyard that provides privacy and room to enjoy the outdoors. A brand-new roof installed in 2025 adds peace of mind and long-term value. Move-in ready and competitively price. This home is a fantastic opportunity for buyers. Looking for space, comfort, and a great value This home is ready for its next owners. Schedule your showing today and bring your offers. YOUR NEW HOME AWAITS. DOWN PAYMENT ASSISTANCE IS AVAILABLE TO QUALIFIED BUYER(S)

Listing is courtesy of: AUDITH POLEON REALTY (863-709-5643)

Listing Agent: Audith Poleon (863-709-5643)

Remarks: Welcome to your perfect slice of Florida living! This solid concrete block home combines durability, comfort, and modern updates - making it an exceptional opportunity whether you're searching for your next residence or an investment property. Step inside to discover brand-new vinyl plank flooring that flows beautifully throughout, complemented by newer stainless steel appliances that bring a fresh, modern feel to the home. Major systems have already been taken care of for you, including a 2022 HVAC system and 2022 water heater, plus a metal roof installed in 2012 for long-term peace of mind. Outside, enjoy a fully fenced yard - perfect for pets, entertaining, or simply relaxing under the canopy of mature shade trees. The carport and additional parking pad provide plenty of space for vehicles, guests, or even a boat. Nestled in an established neighborhood, this home offers the rare advantage of NO HOA or CDD fees, giving you both freedom and affordability. You'll love the convenient location - just minutes from lakes, parks, shopping, and vibrant downtown Winter Haven. Whether you're looking to settle in or invest, this property checks all the boxes. Don't miss your chance to own this move-in-ready gem - schedule your private showing today before it's gone!

Listing is courtesy of: CENTURY 21 BEGGINS ENTERPRISES (813-658-2121)

Listing Agent: John Evans (813-992-3483)

Remarks: Minutes from Legoland and Peppa Pig Theme Park, this 5-bedroom, 3-bath home offers comfort and functionality in a quiet cul-de-sac. The open-concept layout features a spacious kitchen, main-floor den, and a first-floor guest suite with full bath. Upstairs includes a versatile loft and a primary suite with walk-in closet and dual vanity. Additional highlights include second-floor laundry, tile in wet areas, a 2-car garage, and a large backyard ideal for entertaining. Conveniently located near shopping and dining. Low HOA—perfect for first-time buyers or investors. (Tenant Occupied - Lease ends October 2026)

Listing is courtesy of: NEWBERRY REALTY & DEV GRP INC. (321-607-2354)

Listing Agent: Gylwerd Sevilla Oviedo (305-989-7853)

Remarks: SELLER OFFERS $10,000 CREDIT TOWARD CLOSING COSTS OR UPGRADES, BUYER’S CHOICE PRIOR TO CLOSING! Welcome to this charming 3-bedroom, 2-bathroom home in Winter Haven, offering an open and functional layout perfect for everyday living and entertaining. This solid single-family residence features approximately 1,449 sq. ft. of comfortable living space, including a cozy living/dining combination and a well-appointed kitchen. The property boasts significant recent upgrades, including: - Roof: Installed in 2021 - HVAC: Brand new A/C system, ducts, and air handler installed one year ago - Water Heater: Only 3 months old - Flooring: Brand new tile throughout the entire home Outside, you will find a large fenced backyard providing ample room for gardening, play, or weekend grilling. Ideally located on a quiet residential street, this home is just minutes from shopping, dining, major highways, local attractions, and Legoland. With no HOA, this home is an excellent opportunity for first-time buyers, those looking to downsize, or investors seeking value and convenience. Don’t miss out on this Winter Haven gem!

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

Listing Agent: David Small (407-601-8351)

Remarks: MOVE-IN READY WITH MODERN UPDATES ON A PRIME CORNER LOT! Built in 2017 and featuring a LOW HOA, this beautifully maintained home offers a desirable open floor plan with a 3-way split bedroom layout, delivering the perfect balance of functionality and privacy. Enjoy peace of mind with NEW luxury vinyl plank flooring (2025) and fresh interior paint (2025), creating a clean, modern, truly turnkey feel throughout. Architectural details like decorative arches add character, while 18x18 tile in all wet areas enhances durability and style. The kitchen showcases 36” espresso cabinetry, generous storage, and all appliances included, making it ideal for both everyday living and entertaining. Additional highlights include window treatments throughout, an inside laundry room with washer and dryer, and abundant storage space. Step outside to your covered lanai, perfect for relaxing year-round. Situated on a spacious corner lot, the property offers added privacy and curb appeal. Conveniently located just minutes from Highway 27 and approximately 15 minutes to I-4, providing easy access to commuting, shopping, and dining. 1711 sq ft | 3 Bedrooms | 2 Bathrooms | 2-Car Garage

Listing is courtesy of: KELLER WILLIAMS TAMPA CENTRAL (813-865-0700)

Listing Agent: William Kilpatrick (863-669-8090)

Remarks: Discover this gem in the heart of Winter Haven! This spacious home with 5 bedrooms and 3 full bathrooms combines comfort and style. Imagine natural light flooding every space, a modern kitchen, and generous areas for the whole family. Plus, you’ll

Listing is courtesy of: LA ROSA REALTY KISSIMMEE (407-930-3530)

Listing Agent: Maria Medina Fontes (210-480-9397)

Remarks: Welcome to your own slice of paradise on the private shores of Lake Lewis located in the highly sought-after gated community of Orchid Springs Estates! This stunning Mediterranean-style estate offers the perfect blend of luxury, comfort, and timeless elegance. Boasting 4 spacious bedrooms and 4 full baths, this custom-designed home features a beautifully appointed kitchen ideal for entertaining, a dedicated pool bath for added convenience, and multiple living spaces filled with natural light. Step outside to your private screened-in pool oasis, where tranquil lake views and tropical landscaping create the ultimate Florida lifestyle experience. Enjoy fishing, kayaking, or simply relaxing by the water in this serene, private lakefront setting. With premium finishes throughout and exceptional attention to detail, this home offers everything you need in one of the area's most distinguished neighborhoods. Don’t miss this rare opportunity—schedule your private tour today!

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

Listing Agent: Steve Lockhart (863-289-9801)

Remarks: Welcome to this beautifully upgraded 3-bedroom, 2-bath home offering 2,045 square feet of refined living space in the highly desirable Lake Ashton 55+ golf community—where luxury meets an active, resort-style lifestyle. This thoughtfully designed home features top-notch upgrades throughout, including an additional sliding glass door leading to the back patio, flooding the living space with natural light and creating a seamless indoor-outdoor living experience. The spacious kitchen is a standout, boasting abundant cabinet storage with extended cabinetry along the back wall, perfect for entertaining, organization, and everyday convenience. Smart hybrid water heater and water softener system as well The open and inviting floor plan provides generous living and dining areas, while the private primary suite offers comfort and tranquility. Two additional bedrooms are ideal for guests, hobbies, or a home office. Both bathrooms are well-appointed, and the home’s layout is designed for easy living. Located within Lake Ashton, residents enjoy world-class amenities including championship golf courses, clubhouses, fitness centers, pools, tennis and pickleball courts, planned activities, and a vibrant social calendar. Experience the best of Florida living in this exceptional home—schedule your private showing today and discover everything Lake Ashton has to offer.

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

Listing Agent: Cliff Glansen

Remarks: Short Sale. Motivated Sellers- well below appraisal price - Price requires bank approval - Located in the growing Villa Mar community, this Cali floor plan offers 1,828 square feet of modern comfort in a location that blends resort-style amenities with everyday convenience. Residents enjoy a sparkling pool with a second on the way, a playground, and a planned dog park, creating an active and welcoming neighborhood lifestyle. Just minutes from Legoland, Highway 27, shopping, schools, medical centers, and dining, this home offers both accessibility and charm. The open kitchen is a chef’s delight with granite countertops, a generous island, upgraded cabinetry, and stainless-steel appliances, all connecting to bright and spacious living and dining areas. The primary suite easily fits a king bed and features a walk-in closet and a large walk-in shower for ultimate comfort. Outside, a covered lanai offers a peaceful water view with no rear neighbors for complete privacy. Schedule your private tour today and discover why Villa Mar is the perfect address for you.

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

Listing Agent: Christian Clay (863-509-7466)

Remarks: Short Sale. Quaint 3/2 home perfect for 1st time homebuyers or could be a great rental property. Contract is contingent upon third party bank approval. Centrally located to major highways and shopping.

Listing is courtesy of: MILLSHIRE REALTY (863-815-8000)

Listing Agent: Robert Miller, Jr (863-899-9324)

Remarks: Beautifully Maintained 2 bedroom, 2 bath home with a large 2 car garage, perfectly situated on a corner lot. Nestled in Lake Dexter Moorings with a Low Monthly HOA fee! Enjoy access to the neighborhood amenities - a sparkling community pool, a private boat ramp, and a dock. Freshly painted interior! Spanning just over 2,000 square feet of living space, this home offers a spacious great room, an expansive Florida room, and a bright and airy kitchen with a cozy dinette. Large sliding doors open up to the Florida room, creating a seamless transition, allowing easy access to additional space for your entertainment needs. The primary bedroom is complete with an en suite bathroom featuring dual sinks and a walk-in shower. Step outside to your custom brick paver patio, perfect for savouring your morning coffee, having a weekend BBQ, or simply relaxing after a long day. Don't miss this WONDERFUL home, call today!

Listing is courtesy of: ASSOCIATE REALTY (863-618-4000)

Listing Agent: Chrissi Jasso (863-618-4000)

Remarks: Move in ready and located on the Winter Haven Chain of Lakes! Welcome to the gated community of Casarena on the Lakes. This well-designed and meticulously maintained home is set up just right for indoor and outdoor living. The first floor is an open design with the fireplace separating the living and dining area. Enjoy granite countertops and updated appliances in the spacious kitchen that provides the perfect setting to create all of your favorite culinary delights. The living area is a versatile space with a cove for a hosting or exercise area. The main floor is also equipped with a half bath. Head upstairs to the loft that overlooks the living area and separates the two bedrooms. The primary bedroom leads to an open balcony on one side and an updated bathroom on the other. Both bedrooms are oversized with plenty of closet space. The new metal roof was installed in October 2023, The HVAC system has been well maintained, there is a new water heater and the home is also equipped with a whole home generator that is tested regularly. Enjoy the community pool, tennis or pickleball court and access to Lake Cannon, which is on the Winter Haven Chain of Lakes. Downtown Winter Haven is only 10 minutes away and you have quick access to Hwy 92 and 27. Call today for your private showing.

Listing is courtesy of: HOMETRUST REAL ESTATE & PTY MGT (863-450-0602)

Listing Agent: Kami Rickert (954-629-7828)