Winter Haven Single Family Homes For Sale - 708 homes

Remarks: Under contract-accepting backup offers. Private tri-level pool home on a quiet dead-end street—just minutes from the Winter Haven Chain of Lakes and LEGOLAND® Florida Resort. This 4-bedroom, 3.5-bath home is designed for flexibility, privacy, and real Florida living. Situated at the end of a street with no drive-by traffic, this property offers a peaceful setting that’s hard to come by—perfect for those who value space and quiet. One of the biggest advantages here is the tri-level layout, featuring a separate downstairs bedroom and full bathroom—ideal for guests, multi-generational living, or even a private office setup with its own space away from the main living areas. Out back, you’ll find a screen-enclosed pool and expansive patio, built for year-round enjoyment and entertaining. The large, fully fenced yard adds another layer of privacy and gives you room to spread out without feeling boxed in. And here’s where this one separates itself—there’s plenty of room for RV or boat parking with coverage, making it a rare find for buyers needing space for larger vehicles or recreational toys. Inside, the home offers a comfortable flow with multiple living areas, a spacious primary suite, and well-sized secondary bedrooms—giving everyone their own space while still feeling connected. Highlights: 4 Bedrooms | 3.5 Bathrooms Tri-level layout with private downstairs bedroom & full bath Dead-end street – no through traffic Screen-enclosed pool with large outdoor living area Fully fenced yard with strong privacy Covered parking for RV, boat, or extra vehicles Close to Chain of Lakes, boat ramps, and LEGOLAND® If you’re looking for a home that offers privacy, flexibility, and outdoor living—while still being close to everything—this one delivers. Call for your very own private showing today!

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

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

Remarks: Welcome to this exceptional custom-built 2023 luxury residence located within the gated community of Sanctuary by the Lake, where modern elegance, thoughtful design, and everyday comfort come together seamlessly. Perfectly positioned on a spacious corner lot directly across from the lake, this stunning home immediately impresses with its commanding presence and refined architectural detail. Step through the beautiful double front doors and experience an immediate sense of openness, highlighted by soaring ceilings, abundant natural light, and expansive living spaces designed to feel both grand and inviting. With over 3,600 square feet of living space, the thoughtfully designed open layout effortlessly connects formal and casual living areas, creating an ideal setting for both entertaining and relaxed daily living. At the heart of the home lies a beautifully appointed chef’s kitchen, featuring granite countertops, upgraded stainless steel appliances, a breakfast bar, walk-in pantry, and generous prep space, perfect for hosting gatherings or enjoying quiet mornings at home. The kitchen flows naturally into the impressive great room and dining areas, enhancing the home’s seamless indoor living experience. One of the standout features is the oversized covered and enclosed Florida room, custom added by the owners to extend the living space year-round. Whether hosting celebrations, entertaining guests, or simply unwinding while enjoying peaceful surroundings, this space truly elevates the lifestyle this home offers. Designed with privacy in mind, the desirable triple split floor plan includes 4 spacious bedrooms, 3 full bathrooms, and a dedicated private office, ideal for remote work or flexible living needs. The luxurious primary suite serves as a private retreat, complete with dual vanities, a garden tub, separate walk-in shower, makeup vanity, and a very generous walk-in closet. Beautiful luxury vinyl plank flooring flows throughout the main living areas, complemented by tasteful finishes and quality craftsmanship that reflect the home’s custom construction. A well-equipped laundry room with cabinetry, countertop workspace, and sink adds everyday convenience. A 50 amp generator port was added for peace of mind. Beyond the home itself, the location offers the best of Central Florida living. Just minutes from downtown Winter Haven, residents enjoy award-winning restaurants, local boutiques, parks, and year-round entertainment, while nearby access to Lakeland and I-4 provides an easy commute to both Tampa and Orlando. Florida’s Atlantic and Gulf beaches are approximately 90 minutes away, making weekend coastal escapes effortlessly accessible. This is more than a home, it is a refined living experience combining space, luxury, and lifestyle within one of Winter Haven’s most desirable gated communities.

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

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

Remarks: Under Construction. 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: This beautifully updated move-in-ready home sits in a quiet, established community on Lake Dexter, one of Winter Haven’s pristine spring-fed lakes. The neighborhood offers an exceptional lifestyle with private access to a residents-only boat ramp, a sparkling saltwater community pool, and a serene waterfront park complete with a fishing dock, gazebo, playground, and shady green space to enjoy year-round. It’s a rare setting—peaceful, well-maintained, and so close to everything that you can even walk to Legoland. Inside, the home feels bright, airy, and inviting, thanks to thoughtful updates and fresh finishes throughout. The layout is comfortable and functional, featuring a spacious primary suite, two additional bedrooms, and two full bathrooms. The third office or bedroom sits just off the kitchen and is framed by French doors, making it the perfect space for a home office, guest room, or flex space to fit your lifestyle. The seller has invested in quality improvements, including a brand-new roof, fresh interior and exterior paint, a new electric water heater, a full water-softening system, updated light fixtures and hardware, refreshed landscaping, a newly rescreened back patio, and recent servicing of both the AC and irrigation systems. The main living areas feature attractive luxury laminate flooring, adding warmth and style, while the screened back porch provides a quiet, private place to relax overlooking the neatly manicured yard. Winter Haven’s central location between Tampa and Orlando puts major attractions, beaches, airports, and dining just a short drive away, making this an ideal full-time residence or a low-maintenance Florida getaway. This charming home truly checks all the boxes for comfort, convenience, and easy Florida living. All measurements are approximate and should be verified by the buyer or buyer’s agent.

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

Listing Agent: Emily Ward (863-632-1865)

Remarks: Built in 2023, this 4-bedroom, 2-bath Winter Haven home combines modern design with ultimate convenience. The bright, open-concept interior features ceramic tile floors and a chef-inspired kitchen with a large island. Relax on your screened-in lanai overlooking a private backyard. Located minutes from shopping, schools, and attractions—this move-in-ready gem is a must-see!

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

Listing Agent: Anthony Medina (863-242-9847)

Remarks: One or more photo(s) has been virtually staged. Under Construction. This two-story Georgia will definitely be on your mind… This beauty highlights a modern open layout, seamlessly integrating a first-floor kitchen with a central island, a dining room and a welcoming family room with patio access. On the same level is a private owner's suite with an attached bathroom. Situated upstairs is a versatile loft for additional shared living space and four secondary bedrooms to provide restful retreats to family members and guests alike. Villa Mar is a masterplan community of new single-family homes. Near Historic downtown Winter Haven. There are lots of shops, restaurants, bike paths, and easy access to nearby highways. Close to Legoland and Bok Tower Gardens. The much anticipated “Villar Mar” community is what you have been looking for. A safe small town feel with convenience.

Listing is courtesy of: LENNAR REALTY (800-229-0611)

Listing Agent: Ben Goldstein (407-310-7677)

Remarks: One or more photo(s) has been virtually staged. Under Construction. The first floor of the stunning Edison two-story home is host to an open-concept layout that combines the kitchen with the living and dining areas, and an outdoor patio is easily reached off the main living space. Upstairs, five bedrooms surround a versatile loft, including the luxe owner’s suite, complete with a generous walk-in closet and en-suite bathroom. Villa Mar is a masterplan community of new single-family homes. Near Historic downtown Winter Haven. There are lots of shops, restaurants, bike paths, and easy access to nearby highways. Close to Legoland and Bok Tower Gardens. The much anticipated “Villar Mar” community is what you have been looking for. A safe small town feel with convenience.

Listing is courtesy of: LENNAR REALTY (800-229-0611)

Listing Agent: Ben Goldstein (407-310-7677)

Remarks: HUGE $25,000 PRICE DROP! Welcome to one of the largest homes in the desirable Harmony Lake Eloise community! This spacious 5-bedroom, 3-bathroom residence offers a versatile and thoughtfully designed layout perfect for modern living. A generously sized flex room—currently used as a dining area—can easily be converted into a 6th bedroom, home office, or bonus space to suit your needs. The spacious kitchen is a true centerpiece, featuring quartz countertops, beautiful cabinetry, recessed lighting, stainless steel appliances, a large kitchen island, and a walk-in pantry. The interior paint throughout the home offers a soft, inviting color palette that’s easy on the eyes. The first floor showcases beautiful tile flooring throughout, along with a large bedroom and full bathroom—ideal for guests or multigenerational living. You’ll also find an additional sitting area or playroom, providing even more functional living space. Upstairs, all bedrooms are upgraded with luxury vinyl flooring, offering both style and durability. The conveniently located upstairs laundry room adds everyday ease. The expansive primary suite boasts his-and-her closets, dual vanities, and a walk-in shower —your own private retreat. With tons of storage throughout and one of the largest floor plans in the community, this home combines space, comfort, and flexibility. Enjoy a low monthly HOA fee and access to a beautiful community pool. Ideally located just minutes from Lake Eloise, Legoland Florida Resort, shopping, dining, schools, and major roadways, with easy access to Orlando, Tampa, and Walt Disney World. This is a must-see property in Winter Haven!

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

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

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: One or more photo(s) has been virtually staged. Welcome to 228 Spirit Landings Circle, a beautifully maintained 3-bedroom, 2-bath home built in 2023 in the heart of Winter Haven. This move-in-ready home offers modern design, low-maintenance living, and a highly sought-after bonus flex room—perfect as a home office, gym, media room, or even a potential 4th bedroom to fit your lifestyle. The open-concept layout flows seamlessly, featuring spacious living areas, contemporary finishes, and abundant natural light throughout. The split-bedroom floor plan provides both comfort and privacy, making it ideal for families or guests. Perfectly located between Orlando and Tampa, you’ll enjoy easy access to major highways, top employers, and world-class entertainment. Just minutes from LEGOLAND Florida Resort and the scenic Chain of Lakes, this home offers the perfect blend of convenience and lifestyle. If you’re searching for a newer construction home in Winter Haven with flexible living space and prime Central Florida location, this one is a must-see.

Listing is courtesy of: KELLER WILLIAMS ADVANTAGE REALTY (407-977-7600)

Listing Agent: Darein Washington (484-335-8914)

Remarks: One or more photo(s) has been virtually staged. Under Construction. 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. Villa Mar is a masterplan community of new single-family homes. Near Historic downtown Winter Haven. There are lots of shops, restaurants, bike paths, and easy access to nearby highways. Close to Legoland and Bok Tower Gardens. The much anticipated “Villar Mar” community is what you have been looking for. A safe small town feel with convenience.

Listing is courtesy of: LENNAR REALTY (800-229-0611)

Listing Agent: Ben Goldstein (407-310-7677)

Remarks: Welcome to this Charming and newly remodeled home, located in the heart of Winter Haven! This inviting property offers comfortable living with a functional layout, perfect for both relaxing and entertaining. Whether you’re a first-time homebuyer, downsizing, or looking for an investment opportunity, this home is a must-see!

Listing is courtesy of: TCA REALTY, LLC (407-507-3982)

Listing Agent: Deidre Rios (407-433-6238)

Remarks: Welcome to 3410 Fox Ridge Street in Winter Haven, FL. This 3-bedroom 2 bath home features tiled flooring throughout, new appliances, new interior and exterior paint. Granite countertops in kitchen and bathrooms. Open floor plan with a wood burning fireplace. Inside laundry room. Master bedroom features his and her walk-in closets. The home is within walking distance of Garden Grove elementary school. Minutes from Legoland, shopping , medical facilities and many dining options. No HOA in this community. Easy access to major highways and located in between Tampa and Orlando. This home has much to offer. Schedule your appointment today!

Listing is courtesy of: THE HOME COMPANY (863-268-8157)

Listing Agent: Sue Ann Williamon (863-258-3115)

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 contract-accepting backup offers. MOTIVATED SELLERS...OPPORTUNITY KNOCKS ON THIS SPACIOUS & AFFORDABLE 3 Bedroom/2 Bath Home in the heart of SE Winter Haven located in Lake Daisy Estates is ready for you & your family!!! NO HOA or CDD in this established neighborhood that is within 3 miles of LEGOLAND and close to multiple restaurants, shopping, & parks. The natural light fills each room of the home. Open floor plan with split bedrooms. You'll love the large open backyard that is fully fenced. Newer roof (2023). Schedule a tour today!!!

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

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

Remarks: One or more photo(s) has been virtually staged. Fully refreshed and move-in ready, this Ruby Lake home delivers space, thoughtful upgrades, and a layout that stands out from the rest. Offering high ceilings and a well-designed flow from the L-shaped formal living room that transitions into the formal dining area, creating a defined yet open feel. The kitchen sits at the center with a dinette overlooking the family room. A standout feature is the seamless connection to the outdoor space, with three separate access points to the 33x10 screened-in lanai, from the dinette, formal dining area, and primary suite—creating true indoor-outdoor living. The kitchen has been tastefully updated with brand new granite countertops, new range, and new microwave, along with ample cabinetry, a closet pantry, and breakfast bar. The primary suite is generously sized and opens into an en-suite featuring dual walk-in closets, split vanities, a garden tub, walk-in tile shower, and a private water closet. The split-bedroom floor plan offers privacy, while all bedrooms include walk-in closets. Recent improvements make this one stand out from others in the neighborhood, including brand new carpet throughout, fresh interior paint, and a new water heater, giving buyers peace of mind from day one. Located in the gated Ruby Lake community in Southeast Winter Haven, just minutes from convenient access to shopping, dining, Publix, Walmart, Legoland, and Hwy 27 for an easy commute.

Listing is courtesy of: STAR REALTY OF WINTER HAVEN (863-299-7827)

Listing Agent: Carlee Marchetti (863-258-3338)

Remarks: Under contract-accepting backup offers. Welcome to 3108 Buckeye Point Dr — where comfort meets convenience in the heart of Winter Haven. From the moment you arrive, this home invites you in with a layout designed for the way you truly live. With 4 bedrooms and 2 full bath and a brand new A/C system the living spaces feel open yet connected, creating an easy flow for both everyday routines and weekend gatherings. Natural light enhances the home’s warmth, while thoughtful design elements make each space feel intentional and livable. The kitchen serves as the hub of the home, seamlessly connecting to the main living areas — ideal for hosting, relaxing, or simply enjoying a quiet night in. The primary suite offers a private retreat, while additional rooms provide flexibility for guests, work-from-home needs, or hobbies. Step outside and imagine morning coffee, evening unwinding, and effortless Florida living in your own outdoor space. Located in a desirable Winter Haven community, you’ll appreciate the convenience to shopping, dining, medical facilities, schools, and major roadways — all while enjoying the feel of a tucked-away neighborhood setting. Homes that combine layout, location, and livability like this don’t stay available for long. Schedule your private showing and experience 3108 Buckeye Point Dr for yourself.

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

Listing Agent: Jp Phillips (863-670-7923)

Remarks: Welcome to your dream oasis—a stunning craftsman-style 3-bedroom, 2-bath saltwater pool home nestled on just over a quarter acre. This charming property features a large front porch, perfect for relaxing with your morning coffee or enjoying beautiful sunsets. Step inside to find a warm and inviting interior with classic crown molding throughout. The formal dining room offers an elegant space for entertaining, and it can easily double as a home office or flexible bonus room to suit your needs. A cozy dinette off the kitchen provides an additional casual setting for family meals. The backyard is a true retreat, boasting a huge fenced area that provides privacy and security. Dive into the sparkling pool, or unwind on the screened back porch, where you can enjoy the tranquility of your outdoor space. This stunning home also includes a 2-car carport, a long driveway for additional parking, and convenient boat parking—ideal for those who love life on the water. Located near the Lake Howard public boat dock, you’ll enjoy easy access to Winter Haven's sought-after chain of lakes. Additional features include a Generac generator for peace of mind, propane tanks for efficient energy use, and a storage shed for all your gardening tools and equipment. This home perfectly combines comfort, style, and functionality in a picturesque setting. Don’t miss your chance to make it yours!

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

Listing Agent: Michelle Howard (863-944-9920)

Remarks: This move-in ready 3-bedroom Winter Haven pool home offers a fantastic combination of comfort, upgrades, and true Florida living on an oversized lot with no HOA. The home features a brand-new roof, new HVAC system and thermostat, new water heater, new pool pump and chlorinator, new laundry units, new exterior front doors, and an expanded driveway with ample parking. Inside, you’ll find a functional layout with generous living space and fresh improvements throughout. The private in-ground pool creates a relaxing backyard setting, while the large lot provides room for outdoor entertaining, storage, or future additions. Located minutes from the Winter Haven Chain of Lakes, Gene’s Lakeside Marina, LEGOLAND Florida Resort, golf courses, shopping, dining, and local parks, this property sits in one of Central Florida’s most desirable and fast-growing areas. With major updates already completed and convenient access to boating, recreation, and upcoming community development, this home is an excellent opportunity for first-time buyers, families, or investors.

Listing is courtesy of: THE URBAN GROUP, INC. (954-522-6226)

Listing Agent: Ashlee Morrell (941-740-9134)

Remarks: Under contract-accepting backup offers. Now's your chance! Buyer fall out of contract and this home is ready for you! Experience the perfect blend of "Old Florida" soul and modern peace of mind in the heart of the desirable NE downtown grid! This enchanting 1937 vintage gem at 624 Avenue A NE has undergone a comprehensive mechanical evolution over the last 6 months, making it one of the most insurance-friendly historic homes on the market. Major 2025/2026 Upgrades Include: NEW ROOF (6 months old) NEW AC SYSTEM for maximum efficiency ELECTRICAL UPDATES including a brand-new panel PLUMBING UPDATES with modernized piping throughout Inside, you’ll find stunning original hardwood floors and character-rich details. The true "X-factor" is the detached in-law suite—a blank canvas ready for your finishing touches. This versatile space is the ultimate flex-asset: perfect for an income-producing Airbnb, a secluded home office/studio, a private "man cave/she-shed," or a comfortable space for multi-generational living. Located in the premier NE downtown district, you are just steps from the walking trails of Lake Martha and the vibrant dining, boutiques, and breweries of revitalized Downtown Winter Haven. Enjoy a walkable, "park-to-pub" lifestyle with NO HOA and mature oak-canopy streets. With all the major "heavy lifting" already completed, this historic treasure is ready for its next chapter. Schedule your showing today!

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

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