Homes For Sale in Winter Haven 33880 - 176 homes

Remarks: Welcome to this well-maintained 2-bedroom, 2-bath home located in the desirable community of Oakwood Estates in Winter Haven. This home offers a peaceful, well-kept neighborhood with a welcoming atmosphere and a beautiful lake view to enjoy. Recent updates include new kitchen and bathroom flooring, new windows, and new interior and exterior doors, along with a roof that is approximately 5 years old, offering added value and peace of mind. No lot rent—ownership includes the land, with only a low monthly HOA fee. Oakwood Estates is a gated 55+ community offering resort-style amenities including clubhouses, heated pools, fitness center, shuffleboard, tennis courts, and a full calendar of activities. Conveniently located near shopping, dining, medical facilities, and major roadways. Schedule your private showing today and experience easy living in this vibrant community.

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

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

Remarks: This is a beautiful condo located in the heart of Downtown Winter Haven, FL. The sunsets over Lake Howard are unbelievably gorgeous and can be enjoyed sitting on either patio overlooking the waterfront. This is an end unit that comes with 2 covered parking spaces located directly underneath the space. A must see.

Listing is courtesy of: COLLANY PROPERTIES (863-295-9886)

Listing Agent: Christopher Collany (863-412-2170)

Remarks: **PRICE IMPROVEMENT** MAINTENCE-FREE LIVING...Located right in the Heart of Winter Haven at Imperial Villas, a 55+ community. This very well maintained 2 Bedroom/ 2 Bathroom Villa that offers a complete update, boasting tasteful renovations throughout. Being sold Fully Furnished! From the kitchen to the bathrooms, flooring to the roof, nearly everything has been thoughtfully upgraded. Step inside to discover new ceramic tile and luxury vinyl flooring that sets a modern tone. The kitchen showcases stainless steel appliances, granite countertops, ample cabinet and countertop space. Retreat to the owner's suite at the back of the villa, offering a beautifully tiled walk-in shower and a generous walk-in closet. Through the great room, step into to enclosed lanai. Updates include: Roof (2020), Electrical Panel (2023), HVAC (2012) & Tankless Hot Water Heater (2018). Residents of this community have access to a refreshing pool, making it perfect for leisurely afternoons. The low HOA fee of $270/month covers water, internet, cable, gas, trash and grounds maintenance, ensuring a hassle-free lifestyle. Conveniently located just a short walk from the picturesque Lake Howard and minutes away from downtown Winter Haven. You'll have easy access to charming shops, delectable restaurants, the historic Ritz Theater, and vibrant events like farmers markets in the park. Don't miss out on the opportunity to make this your new home. Schedule your private showing today and experience the epitome of Florida living!!

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

Listing Agent: Cheryl Brewer (863-224-0045)

Remarks: PRICE REDUCTION!! Welcome to the lakefront community of Edgewater Manor! Come see this awesome custom built 2017 4 bed 3 bath corner lot (1/3 ac.) home with fenced backyard! Located just off Cypress Gardens Blvd., this bright, open floorplan includes combo living and dining area, an office, and a spacious kitchen with white wood cabinets and grey granite counter tops, stainless steel appliances, gas stove, and eat-in area. There is a large family room off the kitchen, crown molding throughout the home, vinyl fencing, and much more, including: gas tankless WH, vinyl planking floor everywhere but bedrooms, plantation shutters, double pane low E windows, a screened lanai. There is even a plug for an electric car built into garage wall, and a shallow well for lawn irrigation. Plus, close to Legoland, restaurants, shopping, and the chain of lakes. A great find!

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

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

Remarks: Short Sale. Step into one of the largest units at the vibrant 55+ community of Imperial Harbor in Winter Haven! This spacious 3-bedroom, 2-bath condo also features a bonus room. With three comfortable bedrooms, there’s ample space for guests, a home office, or crafting area. Enjoy an active lifestyle with shuffleboard courts, a well-equipped gym, and a billiard room. The heated pool ensures year-round relaxation, and a private community dock on Lake Howard is ideal for boating and fishing enthusiasts. Association dues cover water, basic cable, and internet, and also include access to dock your own boat. Located in the heart of Winter Haven, Imperial Harbor offers a serene and friendly community atmosphere, close to shopping, dining, recreational activities, and medical facilities. Act quickly because a property like this will not last long.

Listing is courtesy of: REALTY COOPERATIVE (800-704-6411)

Listing Agent: Tony Giglio (513-505-5222)

Remarks: You will fall in love with this home from the time you walk through the front door. Has so much to offer, Has rear screen porch and backs up to drainage ditch. Roof is less than a year old and C/H/A is approximately two years. All main furniture will stay. Located in a 55 plus co op with low maintenance fees. Community is gated and has two club houses, two heated pools, Tennis,fishing pier plus much more. This home want last.

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

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

Remarks: Charming 2-bedroom, 2-bath home situated on a beautiful 1-acre lot offering space, privacy, and functionality. This unique property is a true gardener’s paradise, featuring an impressive variety of mature fruit trees including mango, pineapple, plum, pecan, pear, cherry, loquat, peach, and pink guava — providing both beauty and the opportunity to enjoy fresh fruit right from your own backyard. A spacious Florida room offers the perfect space for relaxing, entertaining, or enjoying your morning coffee while overlooking the peaceful surroundings. The property also includes two storage sheds, ideal for tools, equipment, or additional storage needs. Recent updates add value and peace of mind, including new tie-downs, a new hot water heater, a new bladder tank on the well, and a new power pole. Whether you're looking for a quiet retreat, space to garden, or room to spread out, this home offers comfort, practicality, and the charm of country-style living — all on a full acre.

Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (863-701-2350)

Listing Agent: Brandon Casselman (863-808-2755)

Remarks: Under contract-accepting backup offers. Step inside through the large enclosed foyer—perfect as a welcoming entryway, mudroom, or additional sitting space. The home features a comfortable living room and a well-appointed kitchen with a separate dining area, ideal for everyday living and entertaining. A bonus back room provides flexibility and can easily be used as a home office, hobby room, or additional living space. Enjoy outdoor living on the covered back porch overlooking a fully fenced yard—perfect for pets, gatherings, or simply relaxing in your own private oasis. The property is a true gem for those who love fresh fruit, featuring numerous mature trees including mango, avocado, peach, lemon, and other citrus varieties. Additional highlights include two large storage sheds with electricity already in place, offering excellent space for a workshop, storage, or creative projects. There is also a full RV hookup with electric, water, and septic—perfect for travelers or accommodating guests. This property offers a rare combination of comfort, utility, and outdoor enjoyment. Don’t miss this opportunity to own a home with so much to offer!

Listing is courtesy of: LAND SOUTH REALTY, LLC (863-937-8867)

Listing Agent: Ron Denney (863-660-3919)

Remarks: Welcome to your move in ready home in Oakwood Estates, a gated community designed for those aged 55 and older. This beautifully maintained 2-bedroom, 2-bathroom manufactured home comes fully furnished and is being sold as-is, allowing you to move in comfortably without additional expenses. The double panes windows add thermal efficiency, and the 2014 shingle roof is in great condition . Features Include: - Two spacious bedrooms (split bedroom ) and bathrooms - Two attached screened-in porches, perfect for enjoying the Florida sunshine - Utility shed for additional storage (houses washer/dryer) - Parking space for two vehicles - Access to community amenities, including swimming, shuffleboard, fishing pier, and tennis Location: Conveniently located close to shopping centers and restaurants, everything you need is just a short drive away. Enjoy a vibrant community lifestyle with various social activities and events right at your doorstep. This section is a “No Dog” area but other inside pets are acceptable (cat, bird, fish)

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

Listing Agent: Andi Gamble (954-235-7723)

Remarks: Welcome to this beautifully designed 3 bedroom, 2 bathroom home located in the heart of Winter Haven, situated on a generous ½-acre lot. This property offers the perfect blend of space, comfort, and functionality. Step inside to a large open floor plan that’s ideal for both everyday living and entertaining. The open layout allows natural light to flow throughout the home, creating a bright and welcoming atmosphere. The kitchen seamlessly connects to the living and dining areas, making it perfect for gatherings and family time. The home features a 2-car garage, providing ample storage and convenience. Outside, the expansive half-acre lot offers endless possibilities—room for a pool, outdoor entertaining, gardening, or simply enjoying the extra space and privacy.

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

Listing Agent: Marissa Hipp (863-624-4995)

Remarks: Short Sale. Welcome to 503 Holt Circle! This corner-lot property boasts 3 bedrooms, 2 full bathrooms and an abundance of outdoor space. There are plenty of windows to let the natural light in, and a sliding glass door to access the screened-in patio. Enjoy peace of mind with a 2024 roof, 2023 A/C and 2023 electric water heater. Both bathrooms contain thoughtful upgrades for design and functionality. Don’t miss your chance to own a move-in ready home where style, function, and a convenient neighborhood come together. Special financing available with the seller's preferred lender.

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

Listing Agent: Adam Faucett (813-385-2821)

Remarks: Attention investors and those looking for a great deal! Seize a truly unique opportunity to own two homes for the price of one. This property includes a single-family home with 2 bedrooms and 1 bathroom address 215 10th Wahneta St W Winter Haven FL, as well as a single-wide mobile home from 1988 with 2 bedrooms and 1 bathroom address 213 10th Wahneta St W Winter Haven FL 33880. The single-family & Mobile home needs Lot's TLC but has great potential. It could be perfect for someone willing to put in some work or an investor looking to flip or rent it out. Also included on the property is a detached garage offering an extra 480 square feet of storage space. This unique setup offers flexibility depending on your needs. This is truly a rare find at this price point. Don't miss out on this fantastic investment opportunity! Dual Rental Income, Fix-and-Flip Potential, Multi-Generational Living

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

Listing Agent: Jennifer Daniell (863-440-3603)

Remarks: Open and spacious living area is the best way to describe this home. The home features two living areas plus the lanai for additional space. The primary bedroom is large offering two built in closets and a spacious bathroom. The guest bedroom has the bath attached, perfect for visiting guests. The kitchen has an updated island perfect for entertaining. The laundry is located inside the home. Move right into this home, perfect for full time living and spacious for entertaining all the visitors you may have. The TPO roof was installed in 2022 and the ac is 10 years old. Oakwood Estates is a 55+ communities with lots of amenities including two clubhouses, two pools, miniature golf, shuffleboard, tennis courts, and much more. There are activities every day. You can join in or just sit back and enjoy the peaceful community.

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

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

Remarks: A delightful ground-floor 1-bedroom, 1-bath condo that embodies comfortable, low-maintenance Florida living. Step inside to a well-sized living room that invites relaxed gatherings and everyday comfort. The kitchen features a gas stove, ideal for home-cooked meals, and both the A/C and water heater are newer, giving you added peace of mind. This home’s HOA covers exterior maintenance, so you can enjoy more time living and less time on chores. As a resident, you’ll also love the community pool, perfect for refreshing dips on warm Florida afternoons. And to make this condo truly move-in ready, the seller is offering a flooring credit — a great opportunity to personalize the space to your taste. Location highlights: Winter Haven is known for its welcoming community and vibrant lifestyle. Enjoy scenic outdoor living with access to the Chain of Lakes lifestyle, where boating, paddleboarding, fishing, and unforgettable sunsets are part of everyday life. The nearby Chain of Lakes Trail offers miles of paved paths perfect for walking, biking, or jogging. Legoland is just up the road!

Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (863-701-2350)

Listing Agent: Andrew Fearn (863-812-1755)

Remarks: Under contract-accepting backup offers. Picture yourself in this top-floor, 3-bedroom, 2-bathroom condo with a Sun/Florida room, nestled in the desirable Imperial Harbor community of Winter Haven. With easy access via an elevator, this is the peaceful 55+ retreat you’ve been searching for!Imagine waking up and enjoying a morning stroll to the private community dock on Lake Howard, where you can cast a fishing line or set off on a boat ride—and yes, boat docking is INCLUDED in your HOA dues! Spend your afternoons soaking in the heated pool, staying active in the fitness center, or playing a friendly round of shuffleboard or billiards. This is truly resort-style living at its finest. Centrally located only about 45 minutes to Tampa or Orlando.Step inside to discover a bright, open layout with a spacious kitchen, perfect for entertaining. The primary suite boasts a walk-in closet, while the additional bedrooms provide plenty of space for guests, hobbies, or a home office. Plus, the in-unit laundry closet comes equipped with a washer and dryer for ultimate convenience.Best of all, your water, basic cable, and internet are included, making for effortless, low-maintenance living. This is the dream lifestyle you deserve—schedule your private tour today and make it yours!

Listing is courtesy of: IMPACT REALTY TAMPA BAY (813-321-1200)

Listing Agent: Justin Cans (347-238-0790)

Remarks: Welcome to this beautifully renovated 3-bedroom, 2-bath family home tucked away on a quiet street. Set on a spacious .39-acre fenced lot, this property offers both privacy and room to roam — perfect for families, pets, or anyone who loves the outdoors. Step inside to find fresh new flooring, a completely updated kitchen with new appliances, and modern interior and exterior paint that give the home a crisp, inviting feel. The family room with a cozy fireplace creates a warm gathering space, while the large screened porch provides the ideal spot to relax and enjoy year-round. With a new roof and new A/C, this home blends comfort and peace of mind with modern updates. Move-in ready and full of charm — come see it for yourself!

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

Listing Agent: Donna Sealy (863-206-5328)

Remarks: **PRICE IMROVEMENT- MOTIVATED SELLER** Welcome to the community of Eagle Landing in beautiful SE Winter Haven, Florida. This newer home features 4 Bedrooms/2.5 Bathrooms with a spacious two-story layout that maximizes space and natural light perfect for any lifestyle with Low HOA and NO CDD. The modern kitchen design with Island and Breakfast Bar complete with Granite countertops. The primary bedroom with en-suite bathroom with dual sinks, walk in shower and walk-in closet and 3 additional bedrooms offers plenty of space for a growing family or multi-general family. The solar panels offer a great savings to help keep your energy cost down. Conveniently located in a quiet neighborhood, this property is ideally situated close to Publix, Legoland, schools and the Winter Haven Chain of Lakes. If you're looking for a modern, quiet neighborhood, this is your chance. Schedule your showing today before it's gone!

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

Listing Agent: Cheryl Brewer (863-224-0045)

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

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

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

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

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

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

Remarks: Land, flexibility, and future income potential set this property apart. This well-maintained three-bedroom, two-bath home with bonus room and half bath sits on a spacious .93-acre lot, offering privacy and room to grow. The split-bedroom floor plan provides functional living, while the open living and dining areas create an inviting space for everyday life and entertaining. The kitchen offers abundant cabinet storage, and the primary suite features a walk-in closet and relaxing soaking tub. Polk County Building Division has approved the property for a secondary accessory dwelling unit up to 1,000 square feet, creating opportunity for multigenerational living, guest space, rental income, or a private office or studio. Enjoy nearly an acre of usable land with space for a garden, workshop, recreational vehicles, or outdoor entertaining. Conveniently located just minutes from the Chain of Lakes, LEGOLAND, parks, dining, shopping, and with easy access to both Tampa and Orlando. Buyer and buyer’s agent to verify all measurements and ADU requirements.

Listing is courtesy of: S & D REAL ESTATE SERVICE LLC (863-824-7169)

Listing Agent: Tiffani Kline (863-450-0207)