Courtesy: EXP REALTY LLC
888-883-8509
One or more photo(s) has been virtually staged. Discover this exceptional investment opportunity in the thriving city of Winter Haven! This spacious and well-maintained 2-bedroom, 1.5-bath apartment offers the perfect blend of comfort, location, and long-term rental potential. Ideal for investors seeking stable returns, this unit comes equipped with all appliances, including an in-unit washer and dryer, providing added convenience and desirability for future tenants. Perfectly situated, the property is only 5 minutes (approx. 3 miles) from the world-renowned Legoland Theme Park, making it highly attractive for families and professionals relocating to the area. You’ll also be just minutes from Port 27, Winter Haven’s newest lifestyle and entertainment destination located on Lake Hamilton, featuring waterfront dining, recreation, and a growing selection of family-friendly activities. Inside, the unit offers a functional layout with comfortable living spaces, natural light, and low-maintenance living—an excellent advantage for landlords. Whether the intended use is long-term leasing or adding a turnkey property to an investment portfolio, this apartment checks all the boxes. Winter Haven continues to experience strong residential growth, fueled by its central location, access to major highways, beautiful chain of lakes, and expanding entertainment and commercial developments. This upward trend makes the area highly appealing for long-term renters and a promising market for investors. Don’t miss the chance to secure a property in one of Central Florida’s most dynamic and fast-growing communities. This is a solid investment you’ll want to add to your portfolio!
Courtesy: EVERYSTATE INC.
501-725-1234
Charm and curb appeal abound for this Winter Haven home! Step inside into the inviting foyer and into the well-appointed living room, positioned at the center of the home. The kitchen boasts a 4-piece appliance package, ample storage, hard surface countertops, and an eat-in dining room. This split floorplan offers the primary bedroom on one side of the home and two secondary on the other. Come and see for yourself the possibilities that this home has to offer!
Courtesy: SPANN & ASSOCIATES REAL ESTATE
407-468-7512
Turnkey Duplex Near Legoland – Investor Ready! Don't miss this fully renovated, income-producing duplex in a prime Winter Haven location. It is just moments from Legoland Florida and local shopping plazas. This is the perfect turnkey investment or an excellent opportunity for owner-occupancy with built-in rental income. Enjoy hassle-free ownership with a new roof, new flooring and new, efficient mini-split AC systems in both units. Each unit is equipped with stainless appliances and features modern updates throughout. The property offers a highly desirable configuration: Unit A is a spacious 3 Bed/1 Bath, and Unit B is a comfortable 2 Bed/1 Bath. That is a total of five bedrooms and two bathrooms across two separate units. Located in a high-demand rental market near major employment and amenities, this duplex is ready to generate income from day one. Invest smarter—act now before it's gone!
Courtesy: EXP REALTY LLC
888-883-8509
Welcome home! This cheerful 3-bedroom, 2-bath beauty is just four years young and sits in the sought-after community of Lucerne Park Reserve. Step inside and you’ll be greeted by bright open spaces and plenty of space for the whole family. The island kitchen is ready for real everyday living with stainless steel appliances and a roomy pantry that keeps everything in its place. The primary suite offers a comfortable retreat with a walk-in closet and a comfortable walk-in shower featuring a dual-sink vanity. With its split floor plan, you’ll also enjoy two additional bedrooms, a second full bath, and the convenience of an indoor laundry room. Out back, the covered porch gives you a relaxing spot to unwind and soak up that famous Florida sunshine. You’ll be less than 10 minutes from Highway 27 and only about 20 minutes from Legoland—making everyday errands and weekend fun easy. This is a solid home in a community people love. Schedule your showing today—you don’t want to let this one slip by.
Courtesy: KELLER WILLIAMS REALTY SMART 1
863-508-3000
Welcome to resort-style living in the highly sought-after gated waterfront community of Winterset, where convenience meets comfort in this charming 2-bedroom, 2-bathroom downstairs condo. Step inside to discover a spacious living and dining room combo that creates an inviting atmosphere for relaxation and entertaining. The well appointed kitchen features stainless steel appliances and a convenient breakfast bar, perfect for causal dining or morning coffee. The master bedroom suite features a generous walk-in closet, providing ample storage space. For your convenience, a stackable washer and dryer are included. This professionally managed community boasts a plethora of amenities, including a clubhouse, fishing pier, heated pool, hot tub, and tennis courts—all overlooking the serene Lake Winterset, part of the renowned "Chain of Lakes." Enjoy peace of mind with state-of-the-art security in this well-maintained environment. You’re just minutes away from Lego Land and conveniently located near Disney and other Florida amusement parks, shopping, dining, and more. Alternatively, relish the numerous community offerings, including a fitness center, shuffleboard, and expansive green spaces perfect for walking your family pet. Additionally, most furniture is negotiable, providing a seamless transition into your new home. Experience the perfect blend of leisure and lifestyle at Winterset!
Courtesy: COLDWELL BANKER REALTY
863-294-7541
What an amazing home just waiting for it's new owner!! The kitchen has been completely updated with new cabinets and flooring. The home offers two additional living spaces. The lanai on the side of the home is vented with the central ac and is included in the total square footage. or you can escape to the front porch which is also vented increasing the square footage by an additional 200 sf bringing the total living area to 1216 sf. The primary bathroom has an updated vanity. The laundry is located behind the side lanai so you don't have to go outside. The air conditioner is brand new in December 2025. This home is located in Oakwood Estates, a 55+ community which offers many amenities and activities. You can stay as busy as you like, or just sit back and enjoy the peaceful community.
Courtesy: CENTURY 21 WOLF'S CROSSING REALTY
407-449-0000
Cute 2 bed 1 bath home, in a quite area, oversized fenced lot, laminate floors, some renovations done.
Courtesy: FLORIDA REALTY INVESTMENTS
407-207-2220
Completely remodeled 4beds and 3baths with a brand-new roof; freshly painted interior and exterior. Vinyl flooring throughout the home and tile in the bathrooms. This home also features a living/dining room combo with a breakfast bar style kitchen counter. Stainless steel appliances in the kitchen and ceiling fans in every bedroom. There is a room with a bathroom and standing shower on the opposite side of the house. This home is located in a quiet neighborhood, close to all the local restaurants and in walking distance of the public middle and high school in Winter Haven. A fenced in back yard with room to do what you would like to do in this non-HOA neighborhood. Buyers Must verify the measurements and info on this home and property.
Courtesy: SOUTHERN BELLE REALTY
863-299-7800
Cash Only, This home has a new roof, but needs a lot of work.priced accordingly! If you are allergic to smoke do not go in this home, because smoke smell is very strong. But would be a beautiful home with some rehab work.
Courtesy: ASSOCIATE REALTY
863-618-4000
Cable and Internet are included in HOA Fees, valued around $250 monthly. Cable coverage should follow to a secondary home. Move-in ready with room to make it your own! Come see this 3rd FLOOR UNIT located in the beautifully maintained 55+ Granada Building in Orchid Springs! Spanning over 1,500 square feet, this 2 bedroom, 2 bath condo with an OVERSIZED bonus room offers GORGEOUS views of the lagoon — perfect for savoring your morning coffee or unwinding at the end of a long day. Step inside to find an open living and dining area with a tucked-away kitchen. The laundry facility is conveniently located in the same building! OR a washer/dryer hookup could be added to the closet. There is even an ELEVATOR! The monthly HOA fee includes the use of the clubhouse, HEATED community pool, gas, water, trash, cable, internet, pest control, and exterior & grounds maintenance. Whether you're looking to downsize or enjoy a more relaxed pace, this condo offers the perfect blend of comfort and convenience. Don't miss out - CALL us TODAY and start enjoying the best of low-maintenance living in a tranquil setting with captivating water views!
Courtesy: LPT REALTY, LLC
877-366-2213
Discover this beautifully maintained home offering a perfect blend of comfort, style, and functionality. Enjoy a brand-new kitchen featuring modern cabinetry, updated countertops, and sleek appliances—perfect for cooking and entertaining. The spacious living areas are filled with natural light, and the well-appointed bedrooms provide comfort for today’s modern lifestyle. Step outside to a private backyard ideal for relaxation or gatherings. Located close to schools, shopping, major highways, and local attractions, this home delivers exceptional value and true move-in readiness. Don’t miss the opportunity to make it yours!
Courtesy: THE MARKET REALTY COMPANY
863-999-4643
Charming and Affordable 2/2 Block Home in Cypresswood Golf Community Discover comfort and convenience in this beautifully maintained 2 bedroom, 2 bathroom split floor plan block home located in the highly desirable Cypresswood Golf Community. This inviting residence offers a bright, open layout with spacious living areas and large walk-in closets in both bedrooms, providing plenty of storage space. Enjoy the ease of a 2-car garage, a well-designed kitchen, and peaceful views from your private patio. The split floor plan ensures added privacy, making it ideal for guests or a home office setup. Nestled within the scenic Cypresswood community, residents can enjoy beautifully landscaped surroundings, 24-hour gated security, and convenient access to golf, dining, shopping, and major roadways. This home offers the perfect blend of affordability, comfort, and resort-style Florida living.
Courtesy: COLDWELL BANKER REALTY
863-294-7541
Seller motivated. Welcome to your home in Winter Haven—just minutes from Legoland, shopping, medical facilities, and Highway 27 for easy commuting! Originally a 3-bedroom, 2-bath layout, this home has been converted into a spacious 5-bedroom, 2-bath residence, offering incredible versatility for growing families, multigenerational living, or those needing extra space for a home office or hobby rooms. It will need some TLC due to tenant being in property. With five true bedrooms, everyone in the family can have their own retreat while still enjoying generous shared living spaces. Outside, you’ll find a property ideally situated for convenience—whether you’re heading to Legoland for weekend fun, accessing everyday amenities just minutes away, or commuting via Highway 27. This home offers the perfect blend of location, and space in one of Winter Haven’s most desirable areas.
Courtesy: COLDWELL BANKER REALTY
863-294-7541
Discover unparalleled versatility and breathtaking lakefront living with this beautifully remodeled/converted dual-unit home on the shores of Lake Jessie in Winter Haven, Florida. Although zoned single-family residential, this property has been thoughtfully converted into two stunning living spaces—ideal for multigenerational families, in-law accommodations, or dual-family living side-by-side. Unit 1- 2,900 SF welcomes you with a fully renovated two-story layout featuring 4 bedrooms and 3 full bathrooms and 1 half bath. Enjoy gorgeous lakefront views from multiple vantage points and modern finishes throughout, creating the perfect blend of comfort and style. Unit 2- 2,800 SF, mirrors the same level of craftsmanship, two story offering 5 bedrooms and 3 full bathrooms. This spacious unit is also fully remodeled and showcases sweeping views of Lake Jessie, making every day feel like a retreat. Two car garage with additional storage room off the front of the garage. Your backyard becomes a true private oasis—complete with a fire pit, outdoor grill area with a pergola, and a covered boat dock equipped with a boat lift, water, and electric. Watch sea planes take off and land daily from Brown’s Sea Plane Base right from your own waterfront sanctuary. Whether you’re seeking a unique multigenerational setup, an expansive home for a large family, or the ultimate lakeside lifestyle, this exceptional property delivers it all. Don’t miss the opportunity to own this one-of-a-kind lakefront retreat in beautiful Winter Haven, Florida.
Courtesy: BHHS FLORIDA PROPERTIES GROUP
352-688-2227
PRISTINE AND MOVE-IN READY! Come and see this barely lived in 5 BEDROOM, 2.5-BATH home nestled in the solar-friendly community of INMAN GROVES. Built in 2024 and set on a corner lot with NO REAR NEIGHBORS, this home offers peaceful views, unbeatable privacy, and all the advantages of brand-new construction—without the wait. Step inside and be greeted by a bright and open first floor layout designed for effortless living and entertaining. The spacious great room flows seamlessly into the stunning kitchen, featuring QUARTZ COUNTERTOPS, STAINLESS STEEL APPLIANCES, A LARGE CENTER ISLAND, SPACIOUS PANTRY, and ABUNDANT CABINET SPACE. The adjacent dining area makes gathering and conversation feel natural and inviting. A HALF BATH and INSIDE LAUNDRY ROOM add everyday convenience. Upstairs, a VERSATILE LOFT offers the perfect second living space ideal as a TV lounge, playroom, homework hub, or home office. Tucked away in its own private corner is the PRIMARY BEDROOM, complete with an oversized WALK-IN CLOSET and spa-inspired en-suite bathroom with DUAL SINKS, QUARTZ VANITY, and an elegant WALK-IN TILE SHOWER. FOUR SPACIOUS SECONDARY BEDROOMS are thoughtfully arranged around a full bathroom with dual sinks, making room for everyone. Step outside to your FENCED BACKYARD, where a patio awaits—perfect for grilling, lounging, and enjoying Florida’s year-round sunshine. Enjoy low utility costs with your energy-efficient SOLAR PANELS leased at only $93/month. Home is located just off Dundee Road and gives you quick access to Hwy 27, Hwy 17 and Polk Parkway, theme parks like Legoland, Disney and Universal. Close to Winter Haven downtown, hospitals, restaurants, breweries, Chain of lakes and Florida beaches. With contemporary design, energy savings, and an unbeatable location, this home checks every box. Don’t miss your chance to make 271 Inman Blvd your New Haven—schedule your private showing today!
Courtesy: ORLANDO HOMES & INVESTMENTS
407-467-6515
This two bedroom one and a half bath condo offers comfortable living. The kitchen features stainless steel appliances and an eat-in space. Bedrooms are upstairs with a full bath for privacy. A fenced patio provides outdoor relaxation and the community pool is just steps away. Convenient location near shopping dining and Legoland.
Courtesy: LOKATION
954-545-5583
Step into convenience and easy living with this updated 2-bedroom Winter Haven condo, ideally positioned just off the renowned Chain of Lakes. Featuring a brand-new HVAC system and ductwork (2025), an upgraded modern walk-in shower (2025), and durable LVP floors installed in 2024, this home blends comfort with style. Whether you're looking to live near the water, downsize, or add a strong rental to your portfolio, this property delivers. Currently advertised at $1,400 a month for rent—excellent value in a highly desirable location. Located next to Lake Lulu, this home is ideally located within 5 minutes driving distance from Lego Land, as well as several shopping centers. Come see it for yourself!
Courtesy: LIVE FLORIDA REALTY
863-868-8905
Welcome to Lake ‘N Golf Estates! This well-maintained 2-bedroom, 2-bath double-wide manufactured home is situated on 0.09 acres of land that you own, in one of Winter Haven’s desirable 55+ lakefront communities with direct access to the Lake Henry Chain of Lakes. Offering 1,296 sq ft of heated living space, the home features a spacious open layout, large living room, dedicated dining area, and an eat-in kitchen with ample cabinet storage and pantry. The primary suite includes a walk-in closet and private bath, while the guest bedroom also offers a walk-in closet and convenient access to the second full bathroom. Enjoy Florida living year-round with a bright Florida room, enclosed porch, and additional workshop/storage space—ideal for hobbies or extra storage. The covered carport and extended driveway provide convenient parking, and the home is being offered furnished, making it move-in ready. Community amenities include a clubhouse, community pool, boat slips, and golf-cart-friendly streets. Low annual HOA fee covers common area maintenance, recreational facilities, and pool maintenance. Buyer approval required. Conveniently located near shopping, dining, medical facilities, and Winter Haven’s renowned Chain of Lakes lifestyle. Whether you’re seeking a seasonal retreat or full-time residence, this home offers comfort, convenience, and classic Florida charm.
Courtesy: WATSON REALTY CORP.
407-589-1600
PRICE REDUCTION!! LOCATION, LOCATION!! Gorgeous 3 bed, 2 bath POOL home with idyllic views across pretty pond with water frontage and private wooded island!! Located in the sought after gated, Overlook Estates on a spacious corner lot with mature landscaping. The open-concept living area creates an inviting atmosphere, ideal for both relaxed family gatherings and formal entertaining. Enter into the foyer which is flanked by dining room, living room and an additional study/den. Continue through into the spacious kitchen and family room with sliding doors leading to the covered lanai and screened pool area. Relax with your favorite beverage and enjoy the tranquil views of the pond and wooded island with an abundance of wildlife! The primary suite is to the left of the family room and boasts an atmospheric, cozy, gas fireplace and spacious primary bathroom. To the right of the family room are two further bedrooms and full size bathroom. Overlook Estates is perfectly situated among the Chain of Lakes in Winter Haven, not far from Cypress Gardens Blvd for fast commuting and access to dining, shopping and much more. Do not miss this opportunity to live the Florida lifestyle in this unique home!
Courtesy: COLDWELL BANKER REALTY
863-294-7541
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!!! New Refrigerator & Dishwasher will be installed before closing. 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!!!
Courtesy: KELLER WILLIAMS REALTY SMART 1
863-508-3000
A beautiful family home is now available in the desirable gated community of Crossroads at Lake Region. This 4-bedroom, 3-bath property feels like new. The welcoming covered entry features 8-foot glass doors with sidelights that fill the space with natural light and open into the foyer, great room, and kitchen area with impressive 13' ceilings. The well-designed 3-way split floor plan offers comfort and privacy for everyone. The spacious kitchen includes granite countertops, 42" cabinets, a subway tile backsplash, stainless steel appliances, a smart refrigerator, and a large breakfast bar with seating for four or more. The expansive primary suite (15x20) showcases a tray ceiling, a huge walk-in closet, and a gorgeous ensuite bathroom with a large double shower, oversized soaking tub, and dual sinks. The backyard is fully enclosed with a privacy fence and includes solar panels that help significantly lower monthly electric panels. Don’t miss the chance to view this wonderful property - schedule your appointment today! Some photos have been virtually staged to illustrate potential use of space.
Courtesy: KELLER WILLIAMS REALTY SMART 1
863-508-3000
One or more photo(s) has been virtually staged. Beautifully remodeled in 2024, this move-in ready home offers modern updates, energy efficiency, and timeless comfort—all with no HOA. Step inside to an open-concept floor plan featuring high ceilings and abundant natural light. The brand-new kitchen impresses with contemporary finishes, while the updated bathrooms offer a fresh, stylish feel. A desirable split floor plan provides added privacy, making the home ideal for both families and guests. Major improvements include a newer roof and full re-plumbing, giving peace of mind for years to come. The home is also equipped with solar panels for low-cost energy, along with a natural-gas stove and gas water heater—perfect for efficiency and everyday convenience. Outside, enjoy great curb appeal, a fully fenced backyard for pets or play, and a spacious attached 2-car garage. With no HOA restrictions, you have the freedom to personalize, park, and use your property exactly the way you want. This beautifully updated home truly checks every box—style, function, efficiency, and freedom.
Courtesy: MARK SPAIN REAL ESTATE
855-299-7653
Short Sale. We are in the process of getting a short sale approved. So expect delays. Welcome to 29 Golfview Circle NE, a beautifully modernized Winter Haven property offering a rare combination of charm, flexibility, and income-producing potential. The main residence features 3 bedrooms and 2 baths with an open, inviting layout that includes spacious living and dining areas, stainless steel appliances, and a comfortable primary suite with a walk-in closet. Enjoy outdoor living from the covered front porch, the screened back patio, and the fully fenced yard. Additional updates— including a 2021 roof and numerous interior improvements—add peace of mind and long-term value. What truly sets this property apart is the detached 1BR/1BA guest house, completed in 2022 and designed as an ideal in-law suite or rental unit. This private space features polished concrete floors, a sleek updated kitchen, a modern bathroom with a large walk-in shower, an oversized closet with washer/dryer hookups, stainless steel appliances, its own fenced yard, and dedicated parking. Together, both structures offer approximately 2,228 sq. ft. of combined living space and 2,573 sq. ft. total under roof. Located on a corner lot directly across from Polk State College, this home delivers outstanding convenience with exceptional versatility—perfect for multigenerational living, additional income, or both. Opportunities like this are hard to find. Come see everything this remarkable property has to offer!
Courtesy: COLDWELL BANKER REALTY
863-687-2233
Welcome to Lake-N-Golf Estates, a well-loved 55+, no pet community in Winter Haven where you own your land and enjoy low annual HOA dues. This beautifully updated 2-bedroom, 2-bath home with 1,232 sq ft offers an abundance of indoor–outdoor living space with three separate screened/Florida rooms, making it truly unique within the community. At the front of the home, a bright and inviting Florida room provides the perfect spot for morning coffee, reading, or greeting neighbors as they stroll by. A second screened room offers a peaceful, breezy retreat ideal for unwinding in the afternoons, while the third rear screened porch creates a private space to enjoy the outdoors without the Florida heat or bugs. Whether you enjoy entertaining, crafting, relaxing, or simply having multiple flex-use areas, these three distinct rooms add incredible versatility and comfort to the home. Inside, the home has been thoughtfully updated with major improvements including a new AC system, new dishwasher, TPO roof, new windows and siding, new sub-flooring, vinyl plank flooring, and new skirting and underpinning—all offering peace of mind and a fresh, modern feel. Home is being sold partially furnished. Lake-N-Golf Estates provides a wonderful lifestyle with amenities such as a community pool, hot tub, clubhouse, covered dock, and boat ramp, making lake access and recreation convenient and enjoyable. With annual HOA dues of just $550, residents can enjoy a comfortable and affordable active community close to shopping, dining, medical facilities, and everything Winter Haven includes. This well-maintained home, paired with its exceptional outdoor living spaces, is ready for its next owner to enjoy Florida living at its best.
Courtesy: KELLER WILLIAMS REALTY SMART 1
863-508-3000
List Price: $289,999 Property Address: 874 Buccaneer Blvd, Winter Haven, FL 33880 Property Type: Single-Family Residence Bedrooms: 3 Bathrooms: 2 Square Feet (Heated): 1,482 (verify per county records) Lot Size: 5,488 sq ft (approx. 0.13 acres) Year Built: 2014 Subdivision / Community: Buccaneer / Winter Haven Garage: 2-Car Garage (verify) Exterior Construction: Block / Stucco Roof: Shingle Cooling / Heating: Central Air / Electric Water / Sewer: Public County: Polk ? ?? Public Remarks (MLS Ready — ~950 characters) Move-in ready 3-bedroom, 2-bath home in a desirable Winter Haven neighborhood! Built in 2014, this charming single-story residence offers an open floor plan with bright natural light, spacious living and dining areas, and a well-appointed kitchen with ample cabinet space. The primary suite features a private bath and generous closet storage. Enjoy relaxing evenings in the fenced backyard, perfect for pets, gardening, or entertaining. Conveniently located near schools, shopping, and major highways for easy commuting. Well-maintained and ready for its next owner! Sellers are highly motivated—come see this beautiful home and make an offer today!
Winter Haven is located in Florida. Winter Haven, Florida has a population of 48,707. Winter Haven is less family-centric than the surrounding county with 26.09% of the households containing married families with children. The county average for households married with children is 26.62%.
The median household income in Winter Haven, Florida is $50,842. The median household income for the surrounding county is $55,099 compared to the national median of $69,021. The median age of people living in Winter Haven is 41 years.
The average high temperature in July is 92.5 degrees, with an average low temperature in January of 49.7 degrees. The average rainfall is approximately 51.2 inches per year, with 0 inches of snow per year.
