Courtesy: LA ROSA REALTY PRESTIGE
863-940-4850
PRIME LOCATION!! Prime Investment Opportunity with Commercial Zoning! Located in the Historic Pughsville neighborhood of Winter Haven. This property offers incredible versatility. Currently a cozy 2-bedroom, 1-bath residential wood framed home, the lot is zoned commercial, opening the door for various business uses. The property features a spacious, fenced-in yard with the added benefit of No HOA and No CDD fees. Ideally situated near Legoland, hospitals, shopping centers, hotels, and Walmart. Don't miss this unique opportunity—make an offer today!
Courtesy: EXP REALTY LLC
888-883-8509
BACK ON MARKET DUE TO BUYERS FAILED FINANCING!! MAGNIFICENT 4BR/3BA POOL HOME!! Located in the gated Winter Haven subdivision of Tuscanny, this exquisitely maintained one story home, with approx. 3,242 sqft including an air conditioned sunroom, has so much to offer; it showcases a full GUEST SUITE and a new roof as of April 2021! Fantastic Features include: crown molding, ceramic tile, laminate flooring in all 4 bedrooms, updated granite countertops, sinks and fixtures, volume ceilings and fresh paint. The Kitchen is a chefs dream!! It has stainless steel appliances with a Subzero fridge, custom maple cabinetry, gas range with a restaurant style warming lamp and commercial vent, accent lighting, and a large walk-in pantry. A spacious family room flows off the kitchen and overlooks the pool, patio, and air conditioned Florida room. The luxurious Master Suite showcases tray ceilings and dual walk-in closets, with a well-appointed en suite Master Bath, including dual vanities, walk-in shower, a jetted tub and a water closet for privacy. The GUEST SUITE has its own private full en suite bathroom. There are 2 additional bedrooms and a guest bathroom, which also connects as a pool bath with outside access. The air conditioned enclosed sunroom is just off the master bedroom, through the French doors, overlooking the pool; perfect to enjoy your morning coffee, and adding great flow to the well thought out floor plan. The pool and deck have been repainted in recent years, and pool AND BUILT IN HOT TUB area have been re-screened. A BBQ patio has been newly added out back for an expansion of the outdoor enjoyment. Also added, a privacy fence tree line and poolside sun shades ensuring separation from rear neighbors. There is an OVERSIZED 2 car side garage, large pavered CIRCULAR DRIVEWAY, attractive mature landscaping, and MORE!!! All this in a beautiful gated community just minutes from LEGOLAND, Disneyworld, and Universal Studios! This well appointed home is PRICED TO SELL. What are you waiting for???!
Courtesy: THE URBAN GROUP, INC.
954-522-6226
Welcome to this special Winter Haven retreat! This spacious 3-bedroom, 1-bath home sits on a large lot and delivers the perfect blend of comfort, convenience, and Florida lifestyle living. Step inside to enjoy generous square footage, fresh upgrades throughout, and an inviting layout ideal for families, investors, or first-time buyers. Major Upgrades Include: Brand-new roof for peace of mind, New HVAC system + thermostat to keep you cool year-round, New water heater, New pool pump & chlorinator for easy, crystal-clear maintenance, New laundry units included, New front exterior doors, Expansive driveway with plenty of parking. Outside, the in-ground pool sets the stage for relaxation and fun, while the oversized lot gives you a blank canvas—create the backyard of your dreams, build additional outdoor living areas, or store all your toys. Located conveniently right in town, you'll love being part of a thriving neighborhood and community. Boat and fishing enthusiasts will appreciate being just minutes from Gene's Lakeside Marina, offering quick access to Winter Haven's famous Chain of Lakes. On the weekends, enjoy the local farmers market, tee off at one of Winter Haven’s 9 golf courses, or make memories with the family at LEGOLAND® Florida Resort. Top 3 Fun Facts About Winter Haven, Florida Winter Haven is the Water Ski Capital of the World: Winter Haven is renowned for its water ski legacy and the iconic Cypress Gardens ski team. There are over 50 Interconnected Lakes: The city boasts one of the largest chains of freshwater lakes in the world—perfect for boating, waterfront dining, and endless fishing adventures. It is Home of the First Theme Park Shows: Long before modern theme parks, Cypress Gardens pioneered live entertainment with its famous water ski shows and Southern Belle performers. Schedule a showing today! With the new hospital opening Dec 2025, this one won't last long!
Courtesy: KELLER WILLIAMS REALTY SMART
863-577-1234
Welcome home! Wait until you enter this large 3 bedroom, 2 bathroom, 2 car garage home. Once you enter you'll notice on the right there's a HUGE formal living room and to the left is the dining room. The Kitchen has newer appliances and overlooks the family room with high ceilings. This is a split floor plan so the 2 guest bedrooms and bathroom are on one side of the home and the primary bedroom is on the other. The primary bedroom is very large and also has vaulted ceilings. The primary bath has a garden tub, separate walk in shower, and a walk in closet. There is also an inside laundry room! No carpet anywhere, just beautiful and luxurious tile throughout. Roof is 2022 and new AC 2025. The home is located 10 mins from Legoland, down the street from the Winter Haven Dog Park, Winter Haven Fire Department, a brand new Publix (currently under construction), Winter Haven Chain of Lakes and tons of restaurants and shopping!
Courtesy: PREFERRED RE BROKERS III
407-440-4900
Short Sale. SHORT SALE---Explore the charm of 440 Kensington View Drive in Winter Haven, Florida, a delightful home boasting a private vinyl fenced side and backyard on an oversized corner lot. Step inside to find three bedrooms and two bathrooms, where the primary suite offers serene privacy and comfort. The kitchen is a homeowner’s dream with upgraded granite countertops, complemented by stylish brown cabinets. Hard flooring flows throughout most of the home, providing both beauty and durability, while the cozy carpet in one guest bedroom offers a touch of warmth. Freshly painted walls and even the ceiling fan in the family room have just been updated, giving the whole space a fresh, inviting feel. Additionally, a covered lanai provides a perfect spot for relaxation or entertaining. Easy access to the Polk Parkway to Orlando And Tampa,
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!!!
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.
