Winter Haven Homes For Sale & Real Estate - 805 homes

Remarks: Under contract-accepting backup offers. Experience the best of College Grove living in this stunning POOL HOME just minutes from Lake Elbert's scenic waterfront. This spacious two story residence features 3 bedrooms, 2.5 bathrooms, and recent updates including a NEW ROOF (2025), EXTERIOR PAINT (2026), and NEW WATER HEATER (2024), plus a HOME WARRANTY for complete peace of mind. Dramatic cathedral ceilings with arched windows flood the formal living and dining rooms with natural light, while the inviting family room showcases a brick fireplace with wood-burning or gas-burning options perfect for cozy evenings. The kitchen includes a bright dinette area ideal for everyday meals and morning coffee. Step outside to your covered patio and sparkling screened pool area where the true Florida lifestyle comes alive, whether you're hosting poolside gatherings, enjoying morning swims, or relaxing under the covered lanai. The fully fenced yard provides a secure, spacious retreat perfect for children to play, pets to roam freely, or creating your own private outdoor oasis with room for gardens, play equipment, or additional entertaining spaces. Upstairs, the spacious primary bedroom offers a private balcony overlooking the screened pool, a peaceful retreat to start or end your day. The primary bath features a walk in closet, dual vanity, a soaking tub and separate shower for added comfort. Two additional bedrooms provide flexible space for family, guests, or home office. Located just minutes from scenic Lake Elbert, where you can enjoy walking paths and beautiful waterfront views, this home offers the perfect balance of tranquility and convenience. With NO HOA, you have the freedom to truly make this property your own. Situated close to Polk State College, top-rated Winter Haven schools, shopping, dining, and Highway 17 with access to LEGOLAND and Central Florida. This is more than a home. It is an opportunity to live comfortably, entertain beautifully, and enjoy everything Winter Haven has to offer.

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

Listing Agent: Jessica Estrada (863-409-1771)

Remarks: Under contract-accepting backup offers. MOTIVATED SELLER-Ready to negotiate-submit your strongest offer... Come and discover the experience of owning this well-maintained 3-bedroom, 2-bath home with 1,450 sq. ft. of living space featuring an open and thoughtfully designed floor plan. Located in the desirable Lake Smart Point community, you’ll enjoy proximity to both Lake Conine and Lake Smart—each with its own boat ramp, perfect for fishing and outdoor activities. This cozy home boasts tile flooring in all common areas, solid wood kitchen cabinets, granite countertops in the kitchen, and quartz countertops in the bathrooms—offering both elegance and durability. The kitchen is further enhanced with stainless steel appliances, all included, giving it a modern and sophisticated touch. Ideally located near hospitals, schools, gas stations, shopping centers, and medical offices. Enjoy quality family time in this growing area with easy access to local attractions such as Legoland, the Historical Wildlife Tour of the Chain of Lakes, and much more. Conveniently located near Highway 27 and I-4 for a smooth commute. Schedule your private tour today!

Listing is courtesy of: HOMETRUST REALTY GROUP (813-444-5777)

Listing Agent: Barbara Prins (407-361-6061)

Remarks: Come enjoy the beautiful Florida sunsets, In this beautiful, furnished home. You can relax in the enclosed Florida room, Carport is long enough to put two cars in. floors have the beautiful laminate wood flooring, all through out the livingroom,and dining areas. All located in a beautiful gated 55 plus park. Two heated pools, two clubhouses, tennis ,fishing pier, minature golf, shuffle board, plus much more. this home want last, act fast.

Listing is courtesy of: SOUTHERN BELLE REALTY (863-299-7800)

Listing Agent: Reta Stead (863-299-7800)

Remarks: The Poinciana floorplan offers a well-designed, one-story layout that includes 4 bedrooms and 2 bathrooms, complete with a spacious two-car garage. This home is centered around a sizable great room, which seamlessly connects to the open kitchen and cozy café area, making it ideal for family gatherings and entertaining. The owner's suite, located at the back for added privacy, includes a walk-in closet and an en-suite bathroom. Three additional bedrooms are thoughtfully arranged to provide flexibility for family, guests, or a home office. A covered patio extends your living space outdoors, perfect for relaxation or dining al fresco. The Poinciana floorplan is designed for those seeking both functionality and comfort in a beautiful, single-story home.

Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)

Listing Agent: Nancy Pruitt, Pa (352-552-7574)

Remarks: Under Construction. Discover this stunning brand-new construction 3-bedroom, 2-bath home with an open living space and a convenient 2-car garage, this move-in-ready gem boasts elegant granite countertops in the kitchen for a touch of luxury and everyday functionality. The bright, airy layout offers three spacious bedrooms, two full baths, and a peaceful setting perfect for relaxing or family life—ideal for first-time buyers or those seeking fresh, contemporary Florida living. Minutes from shopping, dining, parks, and the Chain of Lakes, this serene location combines tranquility with easy access to everything Central Florida offers. Don't miss this pristine new build—schedule your private tour today! All measurements and sizes are deemed to be accurate but not guaranteed; any information contained here that is critical to buyers' purchasing decisions must be verified by the buyers. Private financing is available to qualified buyers.

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

Listing Agent: Juan Carrion (863-581-6028)

Remarks: Under Construction. Discover this stunning brand-new construction 3-bedroom, 2-bath home with an open living space and a convenient 2-car garage, this move-in-ready gem boasts elegant granite countertops in the kitchen for a touch of luxury and everyday functionality. The bright, airy layout offers three spacious bedrooms, two full baths, and a peaceful setting perfect for relaxing or family life—ideal for first-time buyers or those seeking fresh, contemporary Florida living. Minutes from shopping, dining, parks, and the Chain of Lakes, this serene location combines tranquility with easy access to everything Central Florida offers. Don't miss this pristine new build—schedule your private tour today! All measurements and sizes are deemed to be accurate but not guaranteed; any information contained here that is critical to buyers' purchasing decisions must be verified by the buyers. Private financing is available to qualified buyers.

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

Listing Agent: Juan Carrion (863-581-6028)

Remarks: Under contract-accepting backup offers. LAKEFRONT! MUST SEE! Charming FURNISHED 55+ LAKEFRONT 2BR 2BA condo in Winter Haven, FL! Located on the top floor of the complex, providing one of the best views in the building. The Spring Lake Towers community offers many amenities and social events. The association fee covers cable, internet, building and grounds maintenance, common facilities including a gym, library, community kitchen, laundry area, outdoor grills, and more! This condo features a large master suite with a walk-in closet and a roomy shower, a Sizable living/dining area, perfect for entertaining guests, a kitchen that has a unique design, a secondary bedroom that could double as a den or TV room, an enclosed balcony that has an additional storage closet, and relatively new flooring/water heater. The complex is situated on Spring Lake, but it is not limited to it. This lake is part of a canal-connected chain of lakes ranging in size. This area is perfect for many water-based activities, such as fishing, boating, and much more. Additionally, the association offers a very spacious pool deck area overlooking the Lake, and boat slips are available for a reasonable fee. Wonderful location! The property is conveniently located right next to several grocery stores, Northgate Shopping Plaza, and a bus line, as well as minutes away from a movie theater, restaurants, services, medical centers, Winter Haven Hospital, and downtown Winter Haven. All furniture conveys. Seller or private financing available; Do not wait, it will not last long!

Listing is courtesy of: HUT TEAM REALTY (407-559-2929)

Listing Agent: Daniel Hut (863-400-6090)

Remarks: 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.

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

Listing Agent: David Small (407-601-8351)

Remarks: One or more photo(s) has been virtually staged. A rare opportunity to own one of only six cluster homes positioned along the peaceful shoreline of Lake Buckeye! A charming open courtyard entry welcomes you to the front door, creating a private and inviting approach that sets this home apart. Inside, the living room immediately draws your eye outdoors, featuring double French doors that open to an enclosed lanai and extended open patio overlooking lake views. It’s the perfect space to enjoy morning coffee, evening breezes, or simply take in the calm waterfront setting. The layout flows comfortably from the living area into the wrap-around kitchen and adjoining dining space, where a large window overlooks the courtyard entrance and fills the home with natural light. The primary bedroom suite offers a private retreat with its own en-suite bath featuring a walk-in shower, while the second bedroom sits just steps from the guest bath with tub/shower combination — ideal for guests, family, or flexible use as a home office. Additional highlights include a laundry closet and an oversized 550 sq ft 2-car garage with ample storage, providing both convenience and functionality. For easy lake access, the public boat ramp onto Lake Buckeye is located just 0.1 mile down the road. Homes within The Clusters on Lake Buckeye rarely come to market, making this a special opportunity for buyers seeking a property with character, peaceful surroundings, and direct access to one of Winter Haven’s beautiful lakes. **A/C is 2015, Roof is 2017**

Listing is courtesy of: STAR REALTY OF WINTER HAVEN (863-299-7827)

Listing Agent: Carlee Marchetti (863-258-3338)

Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Don't miss out on this opportunity to own this beautiful home that in 1990 was an AWARD winner in the Polk County Builders Association Parade of Homes and built by local custom home builder Gordon Collins. Upon walking up the home your greeted with a very welcoming courtyard. This home has had some updates. The appliances in the kitchen are all updated Frigidaire Gallery Series. The roof was replaced in 2024. The pool/spa was resurfaced in 2023 and also comes with a 10 year warranty. The home features a split bedroom plan and a large open concept great room area, perfect for entertaining. Around the property is beautiful foliage providing privacy. Having a side load 3-car garage with high ceilings is also a bonus. Gorgeous views from inside of the home can be had from several vantage points. Beautiful natural lighting are also assets of the home. Perfect set-up for adding an an ourtdoor kitchen on the covered lanai/ pool area. Some of the furnishings will be included with this property. There is also a central vacuum system throughout. This beautiful home in this desirable sought after neighborhood will not last long at this price.

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

Listing Agent: Scott Kline (863-287-0204)

Remarks: Under contract-accepting backup offers. Pack your bags and move right into this beautiful home. The kitchen was remodeled three years ago. The side porch/lanai adds approximately 200 sf of living space (included in total sf) and is vented with central air. The home features beautiful built ins in the dining area as well as the 2nd bedroom. The primary bathroom has an updated shower and vanity. The shingled roof is 11 years old and the ac is 12 years old. The home comes furnished. Walk through the new sliding door to the front porch which features tinted windows and Berber carpet. This home is located in the Dog area where you can have two pets up to 20lb each. Enjoy Oakwood Estates, a peaceful 55+ community offering many amenities and activities, or just sit on the front porch and watch the world go by. This home is located in the area of Oakwood Estates that allows dogs. There is a 2 pet limit of up to 20 lbs.

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

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

Remarks: Under contract-accepting backup offers. Don’t miss your chance to own this fully rented quadplex offering immediate cash flow. All four units are currently occupied with month-to-month tenancies paying $1200 per month, giving a new owner flexibility to increase rents to market value or renovate units for added equity and higher returns. Each unit features: 2 Bedrooms / 1 Bathroom, spacious living and dining room combination, dedicated laundry room with washer/dryer hookups, gas stoves and hot water heaters. The roof is only 5 years old. Whether you’re looking to expand your portfolio or secure a strong income-producing property, this quadplex checks all the boxes with built-in upside potential.

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

Listing Agent: Harold Baker (863-604-6272)

Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Discover comfortable, low-maintenance living in this inviting 2 bedroom, 2 bath villa located in a small 55+ community in Winter Haven. This well-designed home features vaulted ceilings, great natural light, and a spacious split bedroom layout, giving you and your guests plenty of privacy. Both bedrooms offer generous proportions and walk-in closets, and the primary suite includes a convenient step-in shower.The living room opens to a 12x12 covered patio through sliding glass doors, creating an easy indoor-outdoor flow for relaxing or enjoying fresh air. The one-car garage includes an electric roll-down screen, perfect for ventilation while keeping the space shaded and tidy. Additional highlights include a whole-house water treatment and softener, plus a new roof in 2024 for added peace of mind.The low HOA covers exterior paint, building and roof maintenance, irrigation system repairs, the community wall, and road upkeep, making day-to-day living simple and stress free.This community offers a convenient location near the bus line, medical offices, hospitals, shopping, and dining. You are also close to Winter Haven’s vibrant downtown filled with boutiques, restaurants, and year-round events, along with the city’s beautiful Chain of Lakes known for boating, fishing, and waterfront dining. Ideal for full-time residents or seasonal buyers looking for comfort, convenience, and a welcoming 55+ setting.

Listing is courtesy of: KEYSTONE RESIDENTIAL GROUP LLC (407-556-3249)

Listing Agent: Lisa Bertossa (407-709-1447)

Remarks: Honey, stop the car! This is the one you’ve been waiting for. This beautifully maintained 4-bedroom, 2-bathroom home sits on a spacious 0.45-acre fenced lot, offering the space, privacy, and outdoor lifestyle today’s buyers are searching for. Enjoy the soon-to-be easy access to Avalon and Disney via Sawgrass Rd extension. Step inside and you’re welcomed by a spacious foyer that flows into a cozy sitting area and formal dining room—perfect for gathering with family or entertaining guests. The open-concept kitchen features a charming breakfast nook and overlooks the main living area, creating a warm, connected space where everyone can come together. The private primary suite is a true retreat, complete with dual vanities, a relaxing soaking tub, a walk-in shower, and a large walk-in closet. The split floor plan provides privacy for everyone, while soaring high ceilings throughout the home create a bright and airy feel. Step outside and discover what truly sets this property apart—an outdoor entertainer’s dream. The covered paver lanai opens to a massive fenced backyard with endless possibilities for entertaining, gardening, play, or simply enjoying peaceful Florida evenings. Additional highlights include: New roof installed in 2021 Covered paver lanai perfect for outdoor gatherings Large private backyard with storage shed Two-car garage Interior laundry room Move-in ready condition in a quiet, established neighborhood Homes with this much space, privacy, and charm don’t come around often. Don’t miss your chance—schedule your private showing today before someone else calls it home.

Listing is courtesy of: FUTURE HOME REALTY INC (813-855-4982)

Listing Agent: Paul Shearn (407-713-2127)

Remarks: Welcome to this beautifully maintained 4-bedroom, 3-bath home built in 2023 and located in the Lucerne Park area of Winter Haven. This spacious home with over 3,000 square feet of living space with an open floor plan designed for both comfort and functionality. The large kitchen opens to the main living area, creating the perfect space for entertaining and everyday living. The primary suite provides a private retreat with a spacious bathroom and walk-in closet, while additional bedrooms provide plenty of room for family, guests, or a home office. Conveniently located near shopping, dining, schools, and just a short drive to LEGOLAND Florida Resort. Don’t miss the opportunity to own this nearly new home in a growing community.

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

Listing Agent: Jessica Delgado (407-520-0159)

Remarks: One or more photo(s) has been virtually staged. Under Construction. BELOW MARKET INTEREST RATES with use of Seller's Preferred Lender. Check out the Indigo, a spacious two-story, 5-bedroom, 3-bathroom, 2-car garage home perfect for growing families or hosting guests. Enter the impressive foyer with soaring ceilings that creates an immediate sense of openness. From the foyer, the home effortlessly flows into the main living areas and kitchen. With quartz countertops throughout, stainless-steel appliances and a smart thermostat for energy efficient climate control, the Indigo brings all the things that matter together. The downstairs guest suite and bathroom are tucked away for added seclusion, while the open concept living space is perfect for entertaining. Upstairs, you'll find a generously sized recreation space, ideal for family time or unwinding. The owner's suite is a true sanctuary, featuring a walk-in shower, double vanities, and a spacious walk-in closet. A laundry room with a new washer and dryer is just off the owner’s suite, conveniently located near the 3 additional bedrooms and full bathroom. The Indigo is as functional as it is stylish, providing the perfect balance of comfort and modern living. Just off US-27 with quick access to I-17, Villa Mar puts you close to local hotspots, and everything that makes Central Florida shine. Discover Winter Haven’s Chain of Lakes, explore the historic downtown district, or enjoy a fun-filled day with the family at LEGOLAND® Florida Resort. At Villa Mar, you’ll enjoy a fresh approach to relaxed living, with everyday essentials and local favorites right around the corner. Images shown are for illustrative purposes only and may differ from actual home. Completion date subject to change. Contact or make an appointment for more details on interest rates.

Listing is courtesy of: CASA FRESCA REALTY (813-343-4383)

Listing Agent: Michael Human (813-343-4383)

Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Welcome home to this beautifully maintained move-in ready 3-bedroom, 2-bathroom home with a screened-in porch located in Winter Haven, Florida. As you step inside, you are greeted by elegant French doors and a stunning bay window that fills the living room with an abundance of natural light. The primary suite is privately located on one side of the home and offers its own en-suite bathroom and walk in closet, creating a peaceful retreat at the end of the day. On the opposite side of the home, you will find two additional bedrooms and a second full bathroom. The kitchen features a practical layout and opens to the dining room, creating a comfortable space for daily living and hosting guests. An interior laundry closet adds convenience and makes household tasks simple and accessible. Step outside to enjoy the spacious screened-in back porch, ideal for relaxing or hosting family gatherings. The fully fenced backyard and additional side patio offers a great space for grilling and spending time with friends and loved ones. A one car garage provides secure parking along with additional storage space. This home is conveniently located in the Whisper Lake Community off Highway 17 with quick access to the Polk Parkway, making commutes to Orlando and Tampa simple and efficient. Located just minutes from LEGOLAND Florida Resort, as well as shopping, dining, and everyday amenities. The 3rd bedroom is currently not fully enclosed, but can easily be completed to create a fully private third bedroom, home office, or flex space. It is currently left open behind the dinning room to create a larger space. This delightful home is ready for you, schedule your private showing today.

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

Listing Agent: Ashley Lopez (863-585-0585)

Remarks: Under contract-accepting backup offers. ***More Pictures Coming Soon*** Experience refined living in the heart of Downtown Winter Haven with this architecturally significant residence just moments from the city’s vibrant lakeside lifestyle. Perfectly positioned within walking distance of local restaurants, boutiques, parks, and entertainment, this exceptional residence places you at the center of one of Central Florida’s most charming downtown districts. Residents will also enjoy quick access to LEGOLAND® Florida Resort, the renowned Chain of Lakes, and nearby tennis and recreation facilities. Originally designed by celebrated architect Gene Leedy, a pioneer of the Sarasota School of Architecture, this residence showcases the timeless elegance of Florida modernism. Clean architectural lines, open living spaces, and distinctive exposed concrete elements reflect Leedy’s philosophy of blending structural beauty with functional design. Expansive interiors allow natural light to flow throughout the home, creating a seamless connection between indoor comfort and the surrounding Florida landscape. Inside, the thoughtfully designed floor plan offers 2 spacious bedrooms, 2 full bathrooms, and a convenient half bath, with 1,408 square feet of living space that balances openness with privacy. The residence provides a comfortable setting for professionals, couples, or small families seeking both style and convenience in one of Winter Haven’s most desirable walkable locations. With its architectural pedigree, prime downtown setting, and close proximity to the lakes, recreation, and major attractions, 503 Avenue B NW #503 offers a rare opportunity to enjoy living in the heart of Winter Haven.

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

Listing Agent: James Barris (863-258-6321)

Remarks: Under contract-accepting backup offers. This 2 BR, 2 BA home is located near Rotary Park and Kiwanis Park which is on Lake Martha, both public parks. Each park has room for games and family gatherings. Rotary Park has a baseball field with backstop and other outside activity areas. This home is located near schools, the Winter Haven downtown post office, the Winter Haven (Bay Care Hospital) and several doctors offices and medical clinics. The Winter Haven Public Library is also 6+/- blocks to the west of this property. The home has a metal roof which offers a long life and better storm protection than typical asphalt shingles. The windows have been replaced and the central A/c - Heat system has recently been inspected. A detached storage building provides room for lawn equipment or other items not needed inside the residence, but are more easily accessed than typical attic space provides.

Listing is courtesy of: TOWN & COUNTRY REAL ESTATE (863-293-1141)

Listing Agent: Timothy Irby (863-206-4464)

Remarks: Under contract-accepting backup offers. New price!!! Sellers are motivated. Move-In Ready 3-Bedroom Home on a Premium Lot in Villamar, Winter Haven! Welcome to 124 Emanuelle Dr, nestled in the sought-after Villamar community of Winter Haven! This beautifully maintained 3-bedroom, 2-bath home, built in 2021, sits on a premium lot and offers the perfect blend of comfort, style, and convenience. Step inside to discover a bright, open floor plan designed for modern living. The spacious living area flows seamlessly into a contemporary kitchen, making it ideal for entertaining family and friends. With move-in ready features, you can settle in and start enjoying your new home right away! Enjoy exclusive access to Villamar’s resort-style amenities, including a sparkling pool and a fun-filled playground—perfect for relaxing weekends or active afternoons. The premium lot provides extra space and privacy, setting this home apart from the rest. This home is ideal for families and first-time buyers seeking a welcoming community, modern comforts, and a low-maintenance lifestyle. Don’t miss your chance to own this exceptional property! Schedule your private tour today and make 124 Emanuelle Dr your new address.

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

Listing Agent: Jody Pagan (863-604-2367)