Homes For Sale in Winter Haven 33880 - 190 homes

Remarks: Under contract-accepting backup offers. COMPLETE RE-MODEL ON THIS LAKEFRONT LOT. HISTORIC CHARM WITH ALL MODERN UPGRADES! THIS PROPERTY BOASTS EXPANSIVE VIEWS OF LAKE SHIPP, PART OF WINTER HAVEN'S 24 INTERCONNECTED CHAIN OF LAKES. EVERYTHING HAS BEEN DONE: NEW WINDOWS, PARTIALLY RE-PLUMBED AND RE-WIRED, NEW A/C. AND ROOF MEMBRANE, STUCCO, EXTERIOR PAINT, FLOORING, AND FIXTURES. AS YOU ENTER THE FRONT DOOR, THE SPACIOUS LIVING ROOM HAS A BEAUTIFUL FIREPLACE WHICH IS OPEN TO THE LARGE DINING ROOM. THE KITCHEN, WITH ACCESS POINTS TO ALL LIVING AREAS, FEATURES STAINLESS APPLIANCES, PANTRY AND LAUNDRY CLOSET. JUST OFF THE LIVING AREA IS A FAMILY ROOM (GATHERING ROOM) WHICH HAS FRENCH DOORS LEADING TO A DECK OVERLOOKING THE POOL AND LAKE. A SMALL OFFICE/DEN ALSO HAS ACCESS TO THE POOL DECK. THE MASTER SUITE IS LOCATED ON THE FIRST LEVEL FEATURING A SITTING AREA, DOUBLE CLOSET AND AMAZING LAKE VIEWS. FRENCH DOORS LEAD OUT TO A REAR DECK OVERLOOKING THE OVERSIZED POOL AND LAKE. THE MASTER BATH FEATURES A DOUBLE VANITY AND TILED SHOWER. THE SECONDARY BEDROOMS ARE LOCATED ON THE UPPER LEVEL WITH A SHARED BATH. THE IN-LAW SUITE OFFERS EXCELLENT FLEXIBILITY! ENTRANCE FROM THE MAIN LIVING AREA AS WELL AS A PRIVATE REAR DOOR. IDEAL FOR FAMILY, GUESTS OR SIMPLY MORE LIVING SPACE! THE FIRST LEVEL IS SPACIOUS (IDEAL LIVING/KITCHEN OPTION) INCLUDES A FULL SIZE BATH. A STAIRWAY LEADS TO A LARGE BEDROOM WHICH COULD ALSO BE PERFECT FOR AN OFFICE/DEN. AT THE REAR OF THE HOUSE, THERE IS A SMALL BASEMENT (COULD BE GREAT WORKSHOP OR STORAGE AREA). OWNER WOULD CONSIDER SELLING ADJACENT LOT - GREAT POTENTIAL SECOND HOME, GARAGE - THE POSSIBILITIES ARE ENDLESS. LOCATION IS IDEAL WITH EASY ACCESS TO WINTER HAVEN, CYPRESS GARDENS, BARTOW AND HWY 570 - WHICH MEANS CLOSE PROXIMITY TO THE NEW ORLANDO HEALTH CAMPUS IN LAKELAND.

Listing is courtesy of: CHARLES RUTENBERG REALTY INC (727-538-9200)

Listing Agent: Rob Brandt Dee, Pa (407-415-3800)

Remarks: VERY MOTIVATED SELLER!! Walk right into this well maintained home. The furnishings you see will remain with the home. The kitchen is large and very functional with lots of cabinets and counter space. Enjoy the open and inviting living area, perfect for entertaining. Sit on the screened front porch enjoying your morning coffee with a nice view of the lake. There is no carpet in this home with laminate flooring in all the living areas. Oakwood Estates, a 55+ community offers many amenities and activities. Get your coffee and donuts every Wednesday morning at Koffee Klatch, enjoy an ice cream sundae twice a month or dance to the music at any of the dances held during the winter months. In addition to the many activities, there are two pools and two clubhouses, shuffleboard, miniature golf, bocci ball, tennis courts, and much more. You can be as busy as you would like 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: Turnkey Villa in Stonebridge — Low Maintenance Living, Prime Location Step into easy Florida living with this move-in ready 2-bedroom, 2-bath villa in the highly desirable Stonebridge community. With vaulted ceilings, abundant natural light, and an open-concept layout, the home feels bright, spacious, and immediately inviting. The thoughtfully designed split-bedroom floor plan offers ideal privacy for guests, roommates, or a dedicated home office. The primary suite provides a relaxing retreat with a walk-in closet and a spacious walk-in shower. The kitchen is both functional and welcoming, featuring generous counter space, ample cabinetry, and a breakfast bar that flows seamlessly into the main living area—perfect for everyday living or casual entertaining. Major systems—including the roof, HVAC, and water heater—are all approximately 3 years old, giving buyers peace of mind from day one. Step outside and enjoy one of the home’s standout features: direct proximity to the community pool—just steps away for effortless relaxation. Conveniently located near downtown Winter Haven, Legoland, Disney, and major roadways with access to Florida’s beaches, this home is ideal for full-time living, a seasonal retreat, or an investment opportunity. Opportunities like this don’t last—schedule your private showing today.

Listing is courtesy of: VIVA ORLANDO REALTY INC. (407-861-0000)

Listing Agent: Larry King (404-441-5050)

Remarks: Short Sale. MAKE AN OFFER ON This better than new construction stunning 4-bedroom, 3-bathroom home is just 2 years young and beautifully maintained—ready for you to move right in! Step into a bright and spacious open-concept layout featuring luxury vinyl flooring throughout, soaring high ceilings, and a seamless flow between the living room and kitchen. The kitchen boasts elegant cabinetry, sleek countertops, and modern finishes. Energy-efficient solar panels help keep utility costs low, and the property is fully enclosed with a new vinyl fence for added privacy. The master suite offers a spacious walk-in closet and a spa-like bathroom complete with an extended walk-in shower, dual sink vanity, and a dedicated towel closet. A second bedroom features its own private ensuite, while a third full bathroom is ideal for guests or inlaws. Relax in your fenced in back patio and enjoy the peace and privacy of your surroundings. Conveniently located near shopping where more stores are being built like a new Target, dining, hospitals, schools and top Central Florida attractions—Legoland is 15 minutes away--this home has it all and more. Don’t miss the opportunity to make it yours!

Listing is courtesy of: KELLER WILLIAMS ADVANTAGE III (407-207-0825)

Listing Agent: Marisol Rivera (407-607-5201)

Remarks: Under contract-accepting backup offers. This 2022-built 'Hayden' model in Squires Grove surpasses new construction, offering five generously sized bedrooms and a flexible open-concept floor plan. The property features a bright, south-facing backyard, ideal for enjoying Florida afternoons, a contemporary kitchen equipped with granite countertops, and the assurance of a low-risk Flood Zone X designation. Avoid the typical waiting period for new construction and transition into this energy-efficient smart home promptly. This residence is perfectly suited for either a primary dwelling or an investment opportunity. We encourage you to schedule an appointment to view the home today.

Listing is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)

Listing Agent: Delaindse Leon (407-791-7595)

Remarks: Under contract-accepting backup offers. PRICED TO SELL! Welcome to this spacious 3-bedroom, 2-bathroom home in the highly sought-after Squires Grove community of Winter Haven. This turnkey opportunity features over 1,600 sq. ft. of living space with a functional single-story, split floor plan designed for maximum privacy and flow. Perfectly situated in the booming Central Florida market, you are minutes away from the famous Chain of Lakes and a seamless commute to Lakeland and Orlando. The home boasts a well-sized kitchen, an attached garage, and a peaceful setting in a prime, established neighborhood. Major systems include a well-maintained 2007 roof and an HVAC approximately 10 years old. Note: The solar panel lease provides flexibility as it can be canceled by the new owner. MOTIVATED SELLER—bring your buyer today! This gem won't last long!

Listing is courtesy of: INVEST READY REALTY (786-452-6501)

Listing Agent: Gabriel Penton (239-413-6050)

Remarks: Located in the new Residences at Winter Haven community, this home features the Everglades model floor plan, designed with an open-concept layout that maximizes natural light and functionality. The home backs directly to the community pond, offering open view and added privacy. Built with double-pane insulated windows and constructed in compliance with the current Florida Building Energy Efficiency Code, the home offers modern efficiency standards. Residences at Winter Haven is a newly developed single-family home community conveniently located near shopping, dining, major roadways, and everyday conveniences. There is a natural ease to this home, from the open layout to the thoughtful finishes. The 8-foot doors and premium flooring flow throughout the main living areas, creating a clean and consistent feel. In the kitchen, the focus is on quality and gathering, highlighted by a large waterfall island and 42” cabinetry with crown molding. It’s a home designed for both quiet mornings and hosting friends, with an open living area that leads out to a covered lanai. It’s a clean, modern space that’s ready for you to make it your own. A model home is available for on-site visits within the community.

Listing is courtesy of: KELLER WILLIAMS REALTY AT THE LAKES (407-566-1800)

Listing Agent: Rodrigo Gomes De Almeida (407-837-8173)

Remarks: You finally have freedom & privacy without the constraints of an HOA & it's USDA Eligible which is a rare find! This charming home is situated on a half-acre of dry, high-fenced land, providing the perfect blend of comfort, space & security. The home boasts a 2016 durable metal roof, new Pergo flooring, updated Cold AC, updated plumbing, 50 gallon 2023 water heater and fresh paint inside & out. Perfect for entertaining with open floorplan with large kitchen, breakfast bar, living room, split-bedroom layout and large, screen/window back porch with brick extended patio and outdoor brick grill. One of the highlights of this home is its prime location, backing up to over 300 acres of tranquil woods. Say goodbye to backyard neighbors and look forward to waking up to the sounds of nature, enjoying your morning coffee in a peaceful setting. But that's not all! Calling all car guys! The property comes with a Huge 24’ x 24’ x 13.6’ high garage/shed with INSULATED ceiling and walls. Constructed for 150 mph hurricane winds on a slab with every post 4 ft deep in concrete. It provides ample space & electricity for a shop to work on your cars, RV, boat, recreational toys, storage or a home business. Plus, there is a carport on slab attached to another shed for combined area 43’ x 45’ with privacy fence shielding the back yard. Irrigation system in front and back yard. Conveniently located with easy access to the Parkway & i-4, making commutes to Lakeland, Orlando or Tampa a breeze. Don't miss out on this fantastic opportunity – make this home yours and embrace a lifestyle of comfort, tranquility, and freedom with no HOA! Call today to schedule your private showing!

Listing is courtesy of: KELLER WILLIAMS HERITAGE REALTY (407-862-9700)

Listing Agent: Sheryl Manche (386-882-2121)

Remarks: BIG PRICE REDUCTION – $7,000! Recently Fully Renovated Townhouse – Move-In Ready! Seller offering $4,000 credit toward buyer’s closing costs or interest rate buydown. Don’t miss your chance to own this completely remodeled 2-bedroom, 2.5-bathroom townhouse in Park Lake, now available at an unbeatable price! This home has been beautifully updated from top to bottom, offering modern style and worry-free living: All 3 bathrooms fully renovated with fresh, modern finishes Brand-new kitchen featuring stainless steel appliances (refrigerator, gas range, range hood, microwave), new sink & faucet, New A/C system & new gas water heater for comfort and efficiency Fresh paint throughout (walls, doors, and closets), New vertical and window blinds, New ceiling fans with remote controls and stylish light fixtures in every room, balcony, and lanai, Garage floor freshly painted for a clean, polished look, Washer and dryer included. The spacious main living area is filled with natural light and opens to an extra-large screened lanai, perfect for entertaining or relaxing outdoors. Upstairs, both bedrooms are oversized with private bathrooms, and the primary suite features its own screened balcony. All 3 Bathrooms are renovated, brand new vanities. Prime Winter Haven Location! Next to the new collegiate baseball stadium and parks project, bringing $60M in growth to the city, Direct access to Lake Lulu, part of the Chain of 22 Lakes for boating, fishing, and outdoor fun, Walking distance to dining and shopping: Starbucks, Chick-fil-A, Panera, Outback, Red Lobster, Steps from the Rowdy Gaines Olympic Pool and Advent Fieldhouse, This townhouse is truly move-in ready—all major upgrades are already completed. Perfect as a primary residence, vacation home, or investment property in one of Winter Haven’s most desirable communities. Schedule your private showing today!

Listing is courtesy of: HIGDON HOMES REALTY LLC (863-209-2543)

Listing Agent: Fatma Higdon (863-209-5243)

Remarks: Under contract-accepting backup offers. Florida classic with NEW ROOF now available in Winter Haven! This 3/2 is close to everything, and walking distance to the High School. A/C was replaced in 2022, all appliances convey, and home is clean and move-in ready! Home also includes 2 living areas, a large screened porch (carport), a dining area with terrazzo floors, and a huge backyard with shade tree. Better Hurry!

Listing is courtesy of: STORMS REALTY (813-293-4652)

Listing Agent: Steve Storms (813-293-4652)

Remarks: What a find! Cute as a button, historic charm with some nice updates. From the welcoming front porch to the massive fenced back yard, complete with dog washing station, this is a cozy spot to call home! Love the original hardwood floors, open bright kitchen, and character such as built ins. Roof is less than 10 years old, and the sellers have updated the HVAC including adding a mini split to the main bedroom for those who like it extra cold at night. Plenty of parking and extra storage outside as well...check this one before it gets away!

Listing is courtesy of: HARPER REALTY FL, LLC (863-687-8020)

Listing Agent: Paula Shields (863-581-1498)

Remarks: Welcome to your slice of Florida living in Winter Haven! This well-maintained 2-bedroom, 2-bath home offers 1,620 sq ft of comfortable living space and is packed with valuable upgrades, including the ROOF 2023 and 4 ton A/C 2023, water softener, reverse osmosis system, and rain gutters with leaf guards for added peace of mind. Step inside to find a spacious floor plan. Relax and unwind in the large screened-in lanai, ideal for enjoying Florida’s beautiful weather year-round. The property also features a large storage shed with air conditioning, giving you plenty of room for tools, hobbies, or seasonal items and an inside laundry with washer and dryer included. Located in the desirable Village Park community for those 55+ years young, residents enjoy an incredibly low HOA fee of just $55 a month, which includes access to a sparkling pool and community amenities. Best of all—you own the land! Limited trailer/RV storage is also available on a first-come basis. Perfectly situated between Tampa and Orlando, this home offers convenient access to world-renowned attractions like LEGOLAND Florida Resort, Walt Disney World, Universal Studios Florida, Busch Gardens Tampa Bay, ZooTampa at Lowry Park, and Seminole Hard Rock Hotel & Casino Tampa. You’re also just minutes from shopping, dining, grocery stores, hospitals, golf courses, nature parks, and Florida’s beautiful beaches. With both Tampa and Orlando international airports within about an hour’s drive, travel is incredibly convenient. Whether you're looking for a full-time residence or a seasonal retreat, this home checks all the boxes. Don’t miss your opportunity to live in Village Park—schedule your private showing today!

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

Listing Agent: Carolyn Christian, Llc (863-514-6378)

Remarks: Under contract-accepting backup offers. This home is a blank slate with lots of room. Over 1400 sf of living space plus the lanai with over 300 sf. Much of the flooring is removed showing the sturdy plywood floors. The kitchen is very functional with lots of storage space. The laundry is conveniently located just off the kitchen. The split bedroom floor plan offers lots of privacy for guests. The guest bedroom is a large area that could incorporate an office space with a full back conveniently located outside of the room. The shingled roof was installed in 2017, air conditioner has a manufacture date of 2020, and the water heater was installed in December 2025. If that's not enough it is located in the "dog area", so bring those little fur babies and make this home your own. This home is priced to sell quickly. Make your appointment today!!

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

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

Remarks: New - New - New! This 3 bedroom 2 bath features a beautiful lake view and has been completely remodeled. Updates include a new HVAC system, new metal roof, new kitchen with granite counters, new bathrooms, new flooring, and new septic system. No HOA means you can store your boat. Can be purchased together with 73 High Street to make a family compound or have an income producing property. (MLS P4937859)

Listing is courtesy of: ALLSTATE REALTY SERVICES (863-965-0207)

Listing Agent: Dwight Head (863-965-0207)

Remarks: BIG HOUSE, BIG YARD, BIG OPPORTUNITY!! This solid block and brick 5-bedroom, 2-bath home sits on nearly an acre and offers incredible flexibility — whether you're looking to invest or create your own spacious homestead. With a newer roof and two newer central A/C units already in place, several major components have been updated, giving you a strong head start on improvements and long-term value. Inside, you’ll find five generously sized bedrooms, spacious living areas, ceramic tile throughout, and closets galore — many of them walk-in. The oversized kitchen is a true standout, featuring abundant cabinetry and plenty of space to cook, gather, and entertain. An inside laundry room and dedicated office/den add even more functionality. Outside, enjoy covered parking, a covered front porch, an open rear patio, and a nearly one-acre lot offering endless possibilities. For investors, the layout easily lends itself to a duplex conversion or mother-in-law addition, creating multiple income opportunities. The home does need some TLC, but it is in good condition and full of potential. And if you’re simply looking for a large home with a large yard to make your own, this could be the perfect fit. With a little vision and care, this property could truly become someone’s dream home. INVESTORS WELCOME!

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

Listing Agent: Kimberly Gay (863-559-1585)

Remarks: 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!

Listing is courtesy of: EVERYSTATE INC. (501-725-1234)

Listing Agent: Blake Keathley (661-900-9145)

Remarks: Welcome to your dream home, a charming 2-bedroom, 2-bath retreat with a versatile bonus room that can be used as a 3rd bedroom or a separate home office featuring its own private exterior entrance! This inviting home has been thoughtfully refreshed and is move-in ready, offering fresh interior paint, a new smart thermostat, recent tree removal, and a brand-new shingle roof (03/24) for peace of mind! Inside, you’ll find a spacious kitchen with a breakfast bar that opens to a bright living room, ideal for everyday living and entertaining. The large dining room or secondary family room is conveniently located next to the kitchen and provides plenty of space for gatherings. Relax in the cozy Florida room, featuring warm wood walls and ceilings and an abundance of windows where you can enjoy views of Lake Elbert! Outside you will find your large paver patio, perfect for entertaining or unwinding, and enjoy the privacy of a newly built fully fenced backyard. Additional updates include a new AC (2022), blown attic insulation (2022), water heater (2019), all kitchen appliances (2021), and Exterior Front Porch paint along with a new front door (2025). Conveniently located just minutes from Downtown Winter Haven, Polk State College, HWY 27, and medical facilities, this home blends comfort, flexibility, and an excellent location. Schedule your showing today!

Listing is courtesy of: LIVE FLORIDA REALTY (863-868-8905)

Listing Agent: Jenna Henderson (850-524-3843)

Remarks: Welcome to the Eagle Landing community in Winter Haven, FL. This well-maintained single-family home is move-in ready and waiting for its new owner(s). The open-floor concept creates a comfortable flow throughout the main living areas, while the split floor plan provides added privacy for the primary bedroom and bath with spacious walk-in closet. The kitchen features stainless steel appliances and granite countertops, offering both style and functionality. Additional conveniences include a laundry room, two car garage and low HOA dues, making this home an affordable and practical choice. Experience the charm of small-town living while enjoying the growth and expansion happening throughout Winter Haven. Conveniently located just minutes from Legoland, shopping, dining, and entertainment, and centrally positioned between Tampa and Orlando for easy travel in either direction. Solar panels will be paid off at closing, providing the new owner with the benefit of low electricity bills. The spacious backyard offers room to relax or entertain.

Listing is courtesy of: CENTURY 21 WATSON & MYERS REALTY (863-324-1000)

Listing Agent: Carla Miro (786-897-4081)

Remarks: Charming and well maintained! 2-Bedroom 2- Bath Home in Desirable 55+ Community – You Own the Land with low HOA fees! This inviting home features fresh interior and exterior paint and a newly screened-in front porch, perfect for enjoying your morning coffee, afternoon tea or just relaxing in the Florida breeze. The property also offers a fenced-in backyard, ideal for pets to play or gardening. Additional highlights include a one-car carport and a spacious 22x11 workshop/storage area, providing plenty of room for hobbies, tools, or extra storage. Residents enjoy access to a community clubhouse and sparkling pool, perfect for socializing and staying active in this welcoming neighborhood. Conveniently located near shopping, dining, and local amenities, this home offers both comfort and convenience. Don’t miss this opportunity to own an affordable home with land ownership in a vibrant 55+ community!

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

Listing Agent: Michelle Armbruster (863-521-6879)

Remarks: Under contract-accepting backup offers. Welcome to this beautifully maintained 4-bedroom, 2-bath home located in the desirable community of Winter Haven! Built by the reputable local builder Southern Homes, this residence showcases quality craftsmanship and thoughtful design throughout. This spacious split floor plan offers both privacy and functionality, ideal for everyday living and entertaining. Step inside to find soaring ceilings in the main living area, creating an open and airy feel that enhances the home’s natural light and livability. The large kitchen provides ample space for cooking and gathering, with tile flooring that extends through the kitchen, dining area, laundry room, and both bathrooms for durability and easy maintenance. The primary suite serves as a true retreat, featuring a tray ceiling with elegant crown molding, two walk-in closets, and a well-appointed en-suite bathroom. The primary bath includes a dual vanity, relaxing garden tub, and a separate step-in shower, offering both comfort and convenience. Additional interior highlights include indoor laundry and well-sized secondary bedrooms that provide flexibility for guests, family, or office space. Outside, enjoy a screened-in covered lanai overlooking a fully fenced backyard—perfect for entertaining, pets, or quiet evenings outdoors. The front landscaping has been freshly updated just in time for spring, giving the home outstanding curb appeal while maintaining a move-in ready interior. The garage is a standout feature, offering an epoxy-coated floor, an extra-long extension for added space, and a convenient man door for easy access. All information and property details are deemed reliable but not guaranteed and Buyer/Buyer's Agent is responsible for their own due diligence including but not limited to verifying HOA, Community Info, Rules, Leasing Requirements, Sqft, Lot Size, Room Dimensions, and Taxes.

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

Listing Agent: Ashli Smith (863-248-9438)