Winter Haven Homes For Sale & Real Estate - 904 homes

Remarks: Under contract-accepting backup offers. Step inside through the large enclosed foyer—perfect as a welcoming entryway, mudroom, or additional sitting space. The home features a comfortable living room and a well-appointed kitchen with a separate dining area, ideal for everyday living and entertaining. A bonus back room provides flexibility and can easily be used as a home office, hobby room, or additional living space. Enjoy outdoor living on the covered back porch overlooking a fully fenced yard—perfect for pets, gatherings, or simply relaxing in your own private oasis. The property is a true gem for those who love fresh fruit, featuring numerous mature trees including mango, avocado, peach, lemon, and other citrus varieties. Additional highlights include two large storage sheds with electricity already in place, offering excellent space for a workshop, storage, or creative projects. There is also a full RV hookup with electric, water, and septic—perfect for travelers or accommodating guests. This property offers a rare combination of comfort, utility, and outdoor enjoyment. Don’t miss this opportunity to own a home with so much to offer!

Listing is courtesy of: LAND SOUTH REALTY, LLC (863-937-8867)

Listing Agent: Ron Denney (863-660-3919)

Remarks: Welcome to your move in ready home in Oakwood Estates, a gated community designed for those aged 55 and older. This beautifully maintained 2-bedroom, 2-bathroom manufactured home comes fully furnished and is being sold as-is, allowing you to move in comfortably without additional expenses. The double panes windows add thermal efficiency, and the 2014 shingle roof is in great condition . Features Include: - Two spacious bedrooms (split bedroom ) and bathrooms - Two attached screened-in porches, perfect for enjoying the Florida sunshine - Utility shed for additional storage (houses washer/dryer) - Parking space for two vehicles - Access to community amenities, including swimming, shuffleboard, fishing pier, and tennis Location: Conveniently located close to shopping centers and restaurants, everything you need is just a short drive away. Enjoy a vibrant community lifestyle with various social activities and events right at your doorstep. This section is a “No Dog” area but other inside pets are acceptable (cat, bird, fish)

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Andi Gamble (954-235-7723)

Remarks: Under Construction. 2-story new construction townhome with 1,604 square feet, 3 bedrooms, and a covered lanai, located in the brand-new Harbor of Lake Henry community. Downstairs, enjoy an open layout and a gourmet kitchen with, shaker-style wood cabinets, Samsung stainless steel appliances, including a pantry. The spacious gathering room opens to your covered lanai. The entire lower level and upstairs baths are finished with luxury vinyl plank flooring, with stain-resistant carpet in the bedrooms. Upstairs, you'll find three spacious bedrooms including your owner's suite complete with a walk-in wardrobe, linen closet, and a private en-suite bath with dual vanities and a tiled shower. Additional features for your convenience include a half bath downstairs, upstairs hall bath for the secondary bedrooms, energy-efficient insulation and windows, and a full builder warranty.

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

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

Remarks: Welcome to this immaculately maintained 4-bedroom, 3-bathroom home with a spacious 3-car garage, perfectly situated in the highly desirable Country Club area of Northeast Winter Haven. Located within a gated community, this home offers both privacy and peace of mind. Backing up to an 11-acre jurisdictional wetland, the property provides complete rear privacy with a beautiful natural landscape—no rear neighbors, just serene views and tranquil surroundings. Inside, you’ll find a thoughtfully designed split floor plan with upgraded flooring, modern cabinetry, and stylish countertops throughout. The layout offers both functionality and comfort, ideal for those who love to entertain. Step outside to your private screened back porch retreat and fully fenced yard—perfect for relaxing evenings or weekend gatherings while enjoying the quiet, natural backdrop. This home truly combines luxury, privacy, and location—don’t miss the opportunity to make it yours.

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

Listing Agent: Joshua Taylor (863-651-5471)

Remarks: MOVE-IN READY Home with lakefront homesite! This stunning Highbourne with Coastal elevation greets you with a charming front porch, perfect for relaxing and enjoying the outdoors. Inside, a versatile flex space offers an ideal area for a formal living room or home office, conveniently connected to the kitchen. Just past the flex room is a thoughtfully placed half bathroom. The heart of the home features an expansive open-concept kitchen, dining, and living area, perfect for entertaining family and friends. The kitchen showcases elegant granite countertops, shaker cabinets, and a spacious layout. Sliding doors off the dining area lead to a covered lanai and an oversized backyard, providing serene views of the woods and lake. Upstairs, the oversized primary suite offers a luxurious primary bathroom with dual vanities, providing a private retreat. Three additional bedrooms and a centrally located laundry room complete the second floor, making the home ideal for families. The first floor is fully tiled, adding a sleek and easy-to-maintain finish throughout the main living areas. This Highbourne quick move-in home at Willowbrook North combines modern design, thoughtful layout, and beautiful natural surroundings, offering the perfect balance of comfort and style.

Listing is courtesy of: DRB GROUP REALTY, LLC (407-270-2747)

Listing Agent: Adam Schott (407-270-2747)

Remarks: Welcome to this stunning 5-bedroom, 3-bath home located in the Jace Landing community of Winter Haven. Built in 2021, this modern two-story residence provides nearly 2,700 square feet of living space designed for comfort, flexibility, and contemporary living. The open-concept layout features a bright and spacious great room, modern finishes, and a large kitchen with stainless steel appliances, ample cabinetry, and an oversized island perfect for family gatherings and entertaining. The first floor also includes a versatile flex room or optional sixth bedroom and a full bathroom, making it ideal for guests, a home office, or multi-generational living. Upstairs, the primary suite provides a private retreat with a large walk-in closet and an ensuite bath featuring dual vanities and a walk-in shower. Four additional bedrooms and a convenient upstairs laundry room create plenty of space for the whole family. This home is built with durable block construction on both levels and includes smart-home technology with Alexa integration and energy-efficient systems throughout. Outside, enjoy the covered patio and spacious backyard — perfect for relaxing or hosting outdoor get-togethers. Conveniently located just minutes from downtown Winter Haven, Legoland, shopping, dining, and with easy access to I-4, this home combines modern comfort with everyday convenience. Don’t miss your chance to own this move-in-ready home in one of Winter Haven’s most desirable communities.

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

Listing Agent: Andres Ramirez (863-845-3310)

Remarks: Short Sale. Welcome to 503 Holt Circle! This corner-lot property boasts 3 bedrooms, 2 full bathrooms and an abundance of outdoor space. There are plenty of windows to let the natural light in, and a sliding glass door to access the screened-in patio. Enjoy peace of mind with a 2024 roof, 2023 A/C and 2023 electric water heater. Both bathrooms contain thoughtful upgrades for design and functionality. Don’t miss your chance to own a move-in ready home where style, function, and a convenient neighborhood come together. Special financing available with the seller's preferred lender.

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

Listing Agent: Adam Faucett (813-385-2821)

Remarks: With expanded living areas and versatile spaces, this home offers a comfortable and practical Florida lifestyle in a well-established Winter Haven community. New flooring and fresh interior paint provide a clean, neutral foundation ready for its next owner. Tucked toward the back of the community and accessed by charming, canopy tree-lined roads, the setting offers a peaceful, neighborhood feel ideal for evening walks or bike rides. The enclosed Florida room adds valuable square footage and serves as a flexible extension of the main living area, perfect for everyday living or casual entertaining. A fully enclosed and roofed former atrium creates a unique bonus space that can be enjoyed year-round, offering additional flexibility for hobbies, relaxation, or storage. The fenced backyard provides a private outdoor retreat and features resident koi fish, adding a tranquil touch. The home is equipped with a whole-house generator, offering dependable peace of mind. Residents also enjoy access to the community clubhouse and amenities. Conveniently located near shopping, dining, medical facilities, and major roadways, this property combines comfort, function, and location within a charming, established neighborhood.

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

Listing Agent: J. Michael Nolen, Jr (863-294-7541)

Remarks: Open and spacious living area is the best way to describe this home. The home features two living areas plus the lanai for additional space. The primary bedroom is large offering two built in closets and a spacious bathroom. The guest bedroom has the bath attached, perfect for visiting guests. The kitchen has an updated island perfect for entertaining. The laundry is located inside the home. Move right into this home, perfect for full time living and spacious for entertaining all the visitors you may have. The TPO roof was installed in 2022 and the ac is 10 years old. Oakwood Estates is a 55+ communities with lots of amenities including two clubhouses, two pools, miniature golf, shuffleboard, tennis courts, and much more. There are activities every day. You can join in or just sit back and enjoy the peaceful community.

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

Listing Agent: Kathy Devor (573-450-1679)

Remarks: A delightful ground-floor 1-bedroom, 1-bath condo that embodies comfortable, low-maintenance Florida living. Step inside to a well-sized living room that invites relaxed gatherings and everyday comfort. The kitchen features a gas stove, ideal for home-cooked meals, and both the A/C and water heater are newer, giving you added peace of mind. This home’s HOA covers exterior maintenance, so you can enjoy more time living and less time on chores. As a resident, you’ll also love the community pool, perfect for refreshing dips on warm Florida afternoons. And to make this condo truly move-in ready, the seller is offering a flooring credit — a great opportunity to personalize the space to your taste. Location highlights: Winter Haven is known for its welcoming community and vibrant lifestyle. Enjoy scenic outdoor living with access to the Chain of Lakes lifestyle, where boating, paddleboarding, fishing, and unforgettable sunsets are part of everyday life. The nearby Chain of Lakes Trail offers miles of paved paths perfect for walking, biking, or jogging. Legoland is just up the road!

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

Listing Agent: Andrew Fearn (863-812-1755)

Remarks: Welcome to this beautifully renovated 3-bedroom, 2-bath family home tucked away on a quiet street. Set on a spacious .39-acre fenced lot, this property offers both privacy and room to roam — perfect for families, pets, or anyone who loves the outdoors. Step inside to find fresh new flooring, a completely updated kitchen with new appliances, and modern interior and exterior paint that give the home a crisp, inviting feel. The family room with a cozy fireplace creates a warm gathering space, while the large screened porch provides the ideal spot to relax and enjoy year-round. With a new roof and new A/C, this home blends comfort and peace of mind with modern updates. Move-in ready and full of charm — come see it for yourself!

Listing is courtesy of: KLINE REAL ESTATE SERVICES (863-287-0204)

Listing Agent: Donna Sealy (863-206-5328)

Remarks: Welcome to the inviting 55+ community of Garden Grove Oaks in Winter Haven, FL. This charming manufactured home offers comfortable living in a peaceful, amenity-rich neighborhood perfect for active adults. Inside, you’ll find a bright, open layout with a spacious living area ideal for relaxing or hosting company. Brand-new flooring has just been installed, giving the home a fresh, updated feel. The kitchen offers plenty of cabinetry, solid counter space, and a cozy dining nook. The primary bedroom provides a comfortable retreat with great storage, and the additional bedroom works well for guests, hobbies, or a home office. Enjoy Florida living year-round in the screened porch — perfect for morning coffee or evening breezes. You’ll also appreciate the covered parking, exterior storage, and easy-care landscaping. The property sits high and dry, even during heavy storms, giving you added peace of mind. The community also provides live security in the evenings, offering an extra layer of comfort and safety. Garden Grove Oaks is known for its friendly atmosphere and strong amenities: a clubhouse, pool, shuffleboard courts, and regular community activities that keep you active and connected. With shopping, dining, medical facilities, and Winter Haven attractions just minutes away, this home delivers comfort and convenience in a truly sought-after 55+ community. Don’t miss your chance to make this your next Florida home.

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

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

Remarks: The property you are inquiring about is located in Winter Haven, FL, in the Mandolin area of Polk County. This is a just like designer home in the SE gated community of Mandolin. This is the beautiful model with divided bedrooms, supersized main suite and a fabulous floor plan for entertaining. The kitchen is the vocal point with conversation and dining all flowing together for a warm family friendly environment. Roof and hot water 1 year old, oak cabinetry, two-car garage, and priced ??? Tell us what you think to be in a 33884 gated community at this price!!! Call, text, or email to see this property! *Agents, please read MLS remarks.*

Listing is courtesy of: BROKERS REALTY OF CENTRAL FLOR (863-294-6773)

Listing Agent: Renee Butler (863-294-6773)

Remarks: Located in the highly desirable 55+ maintenance-free gated community of Traditions on Lake Ruby, this wonderful 2-bedroom, 2-bathroom home offers charm, functionality, and an exceptional lifestyle. Upon arrival, you’re greeted by a welcoming Screened-in front porch decked out with tile flooring. Inside, the open-concept floor plan features a spacious living room with vaulted ceilings, Laminate wood flooring, a decorative planter shelf, and triple glass sliding doors leading to the Florida room. The eat-in kitchen showcases an arched entryway, maple wood cabinetry, and corian countertops. Functional upgrades include a stainless steel double bowl sink with a gooseneck faucet, a closet pantry and Upgraded Refrigertor. A charming breakfast nook is ideal for casual dining, while the formal dining area—enhanced with sliding glass doors that open to the fenced yard—seamlessly blends indoor and outdoor living. Solid surface flooring throughout the main living areas ensures style and easy maintenance. The primary bedroom suite features Laminate Wood flooring, a walk-in closet, and views of the backyard. Its ensuite bath includes a maple wood vanity, and a walk-in shower with a glass enclosure. Outdoor enjoyment awaits with a fully fenced yard—perfect for relaxation or entertaining. Additional highlights include a Florida room with tile flooring, Laundry Room, with utility sink, washer & dryer, irrigation system, architectural shingle roof (2020), Water Filtration system, water heater (2023), gutters, generator outlet, solar powered attic vent fan, pull down attic stairs, a 2-car garage with door opener and keyless entry pad, plus a paved driveway and walkway. Traditions at Ruby Lake offers an exceptional array of amenities: a lakefront clubhouse, dock and boat ramp, heated swimming pool and spa, ballroom, billiards, meeting rooms, library, computer room, craft room, dog park, tennis and pickleball courts, basketball, bocce, shuffleboard, fitness center, aerobics studio, and more. The monthly HOA fee covers exterior house painting, cable, internet, front-yard lawn service, and access to clubhouse amenities. . Conveniently located near shopping, restaurants, LegoLand and major routes, this home offers an exceptional and carefree lifestyle.

Listing is courtesy of: CENTURY 21 MYERS REALTY LAKE WALES (863-676-4448)

Listing Agent: Eileen Belanger (863-221-0229)

Remarks: PEACEFUL WATERFRONT Living! Many Beautiful Features & Oversized Living Areas Great for Entertaining! 3.2 Miles to Legoland! Formal Living & Dining Rooms, Family Room, and BONUS Room Upstairs (great for crafts, reading, or toys). Primary Suite offers sitting area & plenty of closet space. So much Extra Space that you could have a roommate helping pay the mortgage. Beautiful Kitchen Featuring Extra Space with Cooking Island & LARGE WALK-IN PANTRY! Eat-in Space OVERLOOKING THE WATER! Enjoy Living in the Waterski Capital of the World Featuring the Chain of Lakes! All sizes are approximate. You will love this home!!

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

Listing Agent: Jenni Thompson (863-899-5255)

Remarks: Under Construction. Welcome to the Campbell, a stunning four-bedroom, two and a half bathroom home located in the heart of Winter Haven, Florida at our Harmony at Lake Eloise community. A beautiful patio welcomes you to a home that optimizes living space with an open concept kitchen overlooking the living area, dining room, and outdoor lanai. Entertaining is a breeze, as this popular single-family home features a spacious kitchen island, quartz countertops, dining area and a walk-in pantry for extra storage. Ample windows and a set of sliding glass doors allow lighting into the dining area and luxury vinyl plank flooring throughout is stylish and charming. The first floor also features a powder bathroom off the living area for convenience. As we head up to the second floor, we are greeted with bedroom one that features an en-suite bathroom with a double vanity and a spacious walk-in closet providing substantial space for storage. Three additional bedrooms, a full bathroom, and a laundry area are located on the second floor. Like all homes in Harmony at Lake Eloise, the Campbell includes a Home is Connected smart home technology package which allows you to control your home with your smart device while near or away. With its spacious layout and contemporary finishes, the Campbell in Harmony at Lake Eloise provides the perfect blend of style and functionality. *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: Best-Priced 2BR Villa with Garage in Vienna Square – and it’s a corner! Built 2022 Welcome to one of the best values in Vienna Square—this corner unit is a light-filled 2-bedroom, 2-bath villa with a 2+ car private garage. You’ll have low-maintenance living in one of Winter Haven’s most sought-after 55+ communities. Built in 2022, this home features a bright, open-concept layout with a seamless flow between the living, dining, and kitchen areas—perfect for both everyday living and entertaining. The kitchen offers modern finishes, tons of cabinets, and great sightlines into the main living space. New stainless refrigerator and microwave in December 2025! In-unit laundry closet for convenience! The spacious primary suite includes a private bathroom and 2 generous walk-in closets. The second large bedroom and full bath provide flexibility for guests or a home office. Enjoy your morning coffee or unwind in the evening on the screened lanai, offering a quiet and comfortable outdoor retreat. Refreshed inside and out with most main furniture included. Vienna Square is known for its active, pet-friendly lifestyle and amenities, including a clubhouse, resort-style pool, fitness center, and social activities—all with a convenient location close to shopping, dining, and medical facilities. Association fees include: • Exterior paint • Roof maintenance • Irrigation water • Lawn mowing • Shrub trimming • Spectrum Internet and TV Priced to sell—schedule your showing today. Easy to show for buyer’s agents using ShowingTime.

Listing is courtesy of: FLAT FEE MLS REALTY (813-642-6030)

Listing Agent: Stephen Hachey (813-642-6030)

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: Welcome to this well-maintained home located in Winter Haven. This property features several recent upgrades that enhance both style and functionality. The interior showcases all new laminate flooring installed throughout the entire home just six months ago, creating a fresh and cohesive look. The home also features updated lighting fixtures in the dining room and bathrooms, adding a modern touch to the living spaces. Outside, the backyard has been thoughtfully improved with a newly installed fence for added privacy and a spacious paver patio area with a sunshade, perfect for outdoor entertaining, relaxing, or enjoying Florida evenings. Additional exterior upgrades include new sod and landscaping, providing great curb appeal and a welcoming first impression. Residents of the community also enjoy access to a community pool and playground, offering great spaces for relaxation and recreation. This home offers a move-in ready opportunity with tasteful updates both inside and out.

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

Listing Agent: Yolanda Floyd (863-577-9369)

Remarks: One or more photo(s) has been virtually staged. Brand new, energy-efficient home available NOW! Retreat to your primary suite located in the back of the home for plenty of privacy and offers a huge walk-in closet. Visit Villamar and explore new single-family homes for sale in Winter Haven, FL. Residents will have access to two resort-style amenity centers featuring a clubhouse, pool, and playground. Winter Haven is known for its beautiful chain of lakes with lakeside restaurants and its award-winning community theater. Nearby attractions include Legoland Florida and Peppa Pig Theme Park. A brand-new model and new phase are coming soon. Each of our homes is built with innovative, energy-efficient features designed to help you enjoy more savings, better health, real comfort and peace of mind.

Listing is courtesy of: MERITAGE HOMES OF FL REALTY (813-703-8860)

Listing Agent: Bryan Sumner (813-336-5895)