Winter Haven Homes For Sale & Real Estate - 931 homes

Remarks: One or more photo(s) has been virtually staged. Short Sale. Welcome home to Villa Mar, a vibrant and growing community in beautiful Winter Haven! Built in 2023 and occupied for just one year, this 5-bedroom, 3-bathroom home offers that “like-new” feel with thoughtful upgrades throughout. As you step inside, you’re greeted by an inviting open-concept layout designed for both comfort and connection. The kitchen shines with stainless steel appliances, an oversized pantry, and cabinets with updated fixtures, all opening to the main living area with NEW laminate flooring—creating a seamless space for gathering and entertaining. A bedroom and full bathroom on the main floor offer ideal flexibility for guests or multi-generational living. Upstairs, you’ll find four additional bedrooms, a loft that’s perfect for a home office or a cozy nook to unwind and recharge, and a conveniently located laundry room. The oversized primary suite features a large walk-in closet and an ensuite bathroom complete with a stand-alone shower, upgraded shower head, and linen closet for added convenience. Step outside to a fully fenced backyard, offering privacy and plenty of space to create your own outdoor retreat—whether that means adding a future pool, garden, or simply enjoying a quiet evening of relaxation. The oversized under-the-stairs storage and two-car garage add even more practicality, while the LOW HOA helps keep ownership easy and affordable. Perfectly situated just off US-27, residents enjoy proximity to dining, shopping, and grocery options, as well as easy access to I-17. Outdoor enthusiasts will love being near the Winter Haven Chain of Lakes, ideal for boating, kayaking, fishing, or simply soaking up the sunshine. Plus, the charming Downtown Winter Haven Historic District is nearby—home to local restaurants, boutiques, and community events like First Fridays, the Wine, Chocolate & Cheese Festival, and so many more! For a weekend of fun with the family and friends, LEGOLAND is only 3.5 miles away! This home beautifully blends modern comfort, functional space, and a convenient location—making it a must-see in the heart of Winter Haven. This is the one you've been waiting on. Schedule a showing today and make it yours!

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

Listing Agent: Brianna Perez Montalvo (407-687-3837)

Remarks: Welcome to this well-kept home in the highly sought-after Cypresswood Golf and Country Club, a gated community known for its beautiful grounds and exceptional amenities. Inside, you’ll find bright, open living spaces that flow seamlessly from the living room to the dining area and kitchen, creating a warm and functional layout for everyday comfort. The kitchen offers ample cabinetry and a practical design, while the bedrooms provide generous space and a relaxing atmosphere. The bathrooms are clean, comfortable, and thoughtfully maintained. At the front of the home, a charming courtyard gives you a private spot to unwind or personalize with your own touches. Residents of Cypresswood enjoy access to golf, tennis, and an on-site clubhouse restaurant, all within a peaceful, well-established community. With convenient access to Winter Haven’s shops, dining, lakes, and major roadways, this home offers a perfect blend of comfort, lifestyle, and location.

Listing is courtesy of: COMPASS FLORIDA LLC (727-339-7902)

Listing Agent: Darin Dobson (407-947-6773)

Remarks: Experience lakefront living at its best in this 2-story townhouse with 3 bedroom 3 bath on Lake Buckeye, located just minutes from Winter Haven. Christian School. !Enjoy breathtaking panoramic lake views from the living room, master bedroom balcony, . this spacious home is perfect for anyone looking to customize their living space. This property has great potential and features an oversized attached 2-car garage with ample storage space and access to a private lift station. Don't miss out on the chance to make this lakefront gem your own. Investment Only.Tenant Occupied. Lease start on 04/01/2026 & Expire On 03/31/2026. $1950/M.CASH FLOW INVESTMENT. INVESTMENT OLY WITH 20% DOWN. DSCR BUSINESS LOAN.

Listing is courtesy of: KURUVILA REALTY ASSOCIATES LLC (954-530-9477)

Listing Agent: Joe Kuruvila (954-822-7900)

Remarks: Under Construction. The Archer II is one of our one-story floorplans features in our Willowbrook South community in Winter Haven, Florida. Take your pick between two sleek exterior options when choosing this floorplan. Inside this 3 bedroom, 2 bathroom home you’ll find 1,328 square feet of comfortable living. The open concept layout allows for seamless movement between spaces making entertaining guests a breeze. It also provides homeowners versatile design options. The kitchen features shaker-style cabinets, quartz countertops, and stainless steel appliances, which are sure to both turn heads and make meal prep easy. You’ll bever be too far from the action with the living and dining area right there. In every bedroom, besides the primary 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 features luxury vinyl plank flooring that will be sure to stand out. It also 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, and you also get additional privacy with a separate door for the toilet and shower. Contact us today and find your home at Willowbrook South. *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: 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 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: 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: 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: 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: 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)

Remarks: Welcome to this charming and versatile property located in the heart of Winter Haven! This 2-bedroom, 1-bath home offers comfort, character, and added flexibility with a private in-law suite — perfect for extended family, guests, or potential rental income. The main home features a bright and inviting living space, a functional kitchen, and well-sized bedrooms filled with natural light. Roof and AC units are 2020. The separate in-law suite provides its own private entrance, offering privacy and convenience for multi-generational living or investment opportunities. Situated in an established neighborhood, this property is conveniently located near shopping, dining, schools, and just minutes from the Chain of Lakes. Whether you’re a first-time buyer, investor, or looking for a home with extra space for loved ones, this property is full of potential. Schedule your private showing today!

Listing is courtesy of: BOARDWALK REALTY ASSOCIATES, LLC (800-567-0535)

Listing Agent: Amanda Johnson (310-554-9364)

Remarks: BRAND NEW ROOF INSTALLED NOVEMBER, 2025. Enjoy the Florida Country Club Lifestyle in this 2 bedroom patio home featuring a foyer with wet bar, spacious living room, dining area, kitchen with wood cabinets and converted Florida room, ideal as a den, office or play room. Additional amenities include an expansive master bedroom, 2 car garage with door opener and front courtyard wall. The home is in move-in condition but does have some original features and it's priced accordingly. This is an ideal opportunity to make this home your own with some contemporary updates. The home is currently tenant occupied on a month to month rental but the tenant may be willing to stay on for an investor purchase. Tenant has been there for 3 years.

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

Listing Agent: Steven Smith, Pa (863-224-2297)

Remarks: One or more photo(s) has been virtually staged. SELLER IS MOTIVATED!!! RENTAL POTENTIAL!!! NO HOA!!! 20 MINUTES AWAY FROM LEGOLAND!!! NEW FLOORING INSTALLED IN FEBRUARY 2026!!!! NEW ROOF INSTALLED IN 2022!!! This 3-bedroom, 2-bathroom home offers the perfect combination of comfort, functionality, and location. The property features a screened-in back porch overlooking a private, fully fenced backyard — ideal for relaxing or entertaining. Enjoy your own private pool with both shallow and deep areas, perfect for family fun or hosting guests. The backyard also includes an area of synthetic grass and a basketball hoop, creating a versatile outdoor space for all ages. A standout feature of this home is the spacious storage shed, thoughtfully divided into two areas. One half is fully set up as an office, complete with a wooden desk, chair, wall-mounted whiteboard, and air conditioning — perfect for working from home. The other half offers additional storage space. The home was extensively updated, with a new roof installed in 2022, along with renovations completed the same year. The flooring was replaced in February 2026, giving the home a fresh, modern feel. High-quality, newer appliances add both style and functionality to the kitchen. Conveniently located just 20 minutes from LEGOLAND Florida Resort and about one hour from Tampa and the beautiful beaches of Florida’s west coast. You’re also just minutes away from Publix, McDonald's, restaurants, and everyday conveniences. The seller is highly motivated and welcomes offers — don’t miss this opportunity!

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

Listing Agent: Julia Ferreira (352-298-7325)

Remarks: Under contract-accepting backup offers. Short Sale. Welcome to your 3 bedroom 2 bathroom home located conveniently in Winter Haven with easy access to shopping, dining, and major roadways. The roof and AC were replaced in 2023. This home features luxury vinyl plank flooring throughout. The living room is spacious and features vaulted ceilings. The kitchen has been remodeled and features newer cabinets and granite countertops and a closet pantry. The primary bedroom is spacious with a walk in closet and en-suite bathroom. The remaining bedrooms offer plenty of space and share the main hall bathroom featuring a single sink vanity and tub/shower combo. The home also features a large screened in back porch, the perfect spot for entertaining. This home has so much to offer. Schedule your private showing today!

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

Listing Agent: Casandra Vann (863-546-5446)

Remarks: Step into comfort and versatility with this beautifully maintained two-story home featuring 4 spacious bedrooms and 3 full bathrooms, perfect for growing families or those who love extra space. Enjoy peace of mind with a brand-new air conditioning system installed in 2025, ensuring year-round comfort. The home offers a well-designed layout with a spacious walk-in pantry, ideal for keeping your kitchen organized and functional. A mix of laminate, tile, and carpet flooring adds both style and practicality throughout the home. Upstairs, you’ll find a convenient laundry closet, making everyday living even easier. The two-car garage has been partially converted, offering flexible space that can be used as needed while still maintaining storage options. Outside, the ample driveway provides plenty of parking for guests and multiple vehicles. This home combines comfort, functionality, and flexibility, ready for you to make it your own!

Listing is courtesy of: GIPSTAR REALTY LLC (954-678-8416)

Listing Agent: Johanna Carmona (954-865-3673)

Remarks: WELCOME TO 3923 BALDWIN LANE, NEW ROOF 2023, NEW A/C 2025, FRESHLY PAINTED 2024. LOCATED IN THE HIGHLY SOUGHT-AFTER TRADITIONS GATED COMMUNITY IN WINTER HAVEN! THIS BEAUTIFULLY MAINTAINED HOME OFFERS THE PERFECT BLEND OF COMFORT, STYLE, AND LOW-MAINTENANCE LIVING. FEATURING SPACIOUS LIVING AREAS, A WELL-APPOINTED KITCHEN, AND A SERENE SCREENED-IN LANAI, IT'S IDEAL FOR RELAXING OR ENTERTAINING. ENJOY RESORT-STYLE AMENITIES INCLUDING A CLUBHOUSE, HEATED POOL, FITNESS CENTER, TENNIS COURTS, AND LAKE ACCESS WITH A PRIVATE DOCK-PERFECT FOR ACTIVE ADULTS 55 AND BETTER! WITH 24-HOUR SECURED GATED ENTRANCE AND A VIBRANT, FRIENDLY ATMOSPHERE. TRADITIONS OFFERS THE LIFESTYLE YOU HAVE BEEN LOOKING FOR. SCHEDULE YOUR PRIVATE TOUR TODAY AND EXPERIENCE FLORIDA LIVING AT ITS FINEST.

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

Listing Agent: Brian Reeves (877-366-2213)

Remarks: Under contract-accepting backup offers. Charming 3-bedroom, 2-bath home located in Winter Haven. This property features granite countertops and ceramic tile flooring throughout. The original carport has been converted into a third bedroom and is currently utilized as a spacious primary suite. Ideal opportunity for first-time homebuyers or investors seeking a potential rental property. Conveniently located near shopping, dining, and local amenities. Ready to move in!

Listing is courtesy of: AGENT GROUP REALTY (843-656-0550)

Listing Agent: John Wiertel (863-289-0447)