Winter Haven Homes For Sale & Real Estate - 971 homes

Remarks: Fixer upper! THIS COULD BE THE ONE. PRIVATE POOL! So many possibilities! Lovely vaulted ceilings, 2 fireplaces, open kitchen, lovely wood accents, mahogany kitchen cabinets, office has a closet and could be converted to a 3rd bedroom 3 car garage/ carport and a separate workshop all on .75 of an acre. roof 10 years old, ac replaced 2024, UVI light 2024

Listing is courtesy of: YELLOWFIN REALTY (813-347-7547)

Listing Agent: Marcia Rains - Nadal, Mrs (813-493-2221)

Remarks: This property is zoned for a duplex and features a large backyard, offering excellent potential for investors. The home is being sold as-is and will be delivered with all items currently inside. Located in a great family-friendly neighborhood, with a new Publix plaza opening nearby adding even more value and convenience to the area.

Listing is courtesy of: FLATFEE.COM (954-965-3990)

Listing Agent: Cliff Glansen

Remarks: One or more photo(s) has been virtually staged. Beautifully renovated home in the heart of Winter Haven! Located 2.1 miles to LEGOLAND Florida Resort, this home is ideal as a primary residence, vacation home, or investment opportunity. Conveniently close to shopping, restaurants, and medical facilities, with easy access to everything Winter Haven has to offer. This move-in ready property features updated finishes throughout and offers the perfect combination of comfort and convenience. Enjoy a large fenced backyard with plenty of space for entertaining, pets, or outdoor activities. Don’t miss your chance to own this charming home in a prime location!

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

Listing Agent: Twinkle Robinson (863-860-6645)

Remarks: Don’t miss this incredible opportunity to own a villa in one of Winter Haven’s most sought-after gated golf communities — at an unbeatable price! This 2-bedroom, 2-bathroom villa offers 1,278 sq ft of comfortable Florida living with a peaceful pond view backdrop. The open floor plan flows effortlessly, and the private enclosed Florida room is perfect for year-round entertaining. The generous primary suite features a walk-in shower, and the guest bath includes a tub/shower combo. Why this is a steal: Priced well below comparable properties in the community, Resort-style amenities INCLUDED — 18-hole golf course, tennis, pickleball, pool, fitness center, clubhouse & restaurant, 24-hour manned gate for peace of mind, Pets welcome, Flexible for investors — 6-month minimum lease allowed. Whether you’re looking for your Florida dream home, a seasonal getaway, or a smart rental investment, this property checks every box at a price that won’t last long. Act fast — opportunities like this don’t stay on the market!

Listing is courtesy of: HUMAN TOUCH REAL ESTATE FIRM (863-651-8236)

Listing Agent: Susan Human (863-651-8236)

Remarks: One or more photo(s) has been virtually staged. Enjoy the beauty of true Florida lakefront living on private Lake Lucerne! Situated on just over half an acre, this fully fenced waterfront property offers peaceful water views, breathtaking sunsets, and endless opportunities for fishing, boating, kayaking, or simply relaxing by the lake. Surrounded by mature trees and natural beauty. This versatile property features a grandfathered-in 3-bedroom, 2-bath single-wide mobile home offering excellent flexibility and future potential. The home includes tiedowns, a slab foundation, power, air conditioning, and a covered and screened patio area perfect for relaxing outdoors while enjoying the peaceful lakefront setting. The metal roof adds durability and functionality, while water has not been connected to the mobile home during the seller’s ownership the existing structure creates opportunities for continued use, renovation, replacement, or redevelopment. The property is grandfathered to allow replacement of the existing mobile home or the opportunity to build your own custom lakefront home. The seller is also including custom home blueprints valued at approximately $3,000 to help bring your vision to life. A major BONUS is the included 2017 KEYSTONE PASSPORT UlLTRA LITE 195RB CAMPER overlooking the lake, offering a comfortable turnkey setup perfect for weekend getaways, seasonal use, or full-time living. The camper is fully furnished and includes all furniture, décor, kitchenware, appliances, manuals, and household contents. Features include heat and air conditioning, working appliances, newer awning, newer tires including spare tire, backup camera, load distribution hitch, small grill, coffee maker, booth-style dining area, full kitchen, cozy sleeping area, and scenic lake views throughout. Additional property features include mature fruit trees such as banana, avocado, pecan, persimmon, and peach, along with a private well, septic system, metal storage shed, and convenient frontage on a main road while still maintaining a quiet waterfront atmosphere. Located in Winter Haven’s desirable lake region, this property is approximately 25 minutes from LEGOLAND Florida Resort and about 35 minutes from Walt Disney World. Whether you’re looking for a waterfront getaway, investment opportunity, or future dream homesite, this unique property captures the charm of Old Florida living while offering privacy, flexibility, and future potential.

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

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

Remarks: PRICE REDUCED $15,000! Welcome to the Enclave at Cypresswood Golf & Country Club. Cypresswood is a Gated community featuring a 24-Hour Guard, 18 Hole Golf Course, Community Pool, Lighted Tennis Courts, Restaurant, and a Pub. This 2 Bedroom Villa is For Sale and Move-In Ready! The owners updated their Home in 2023, just 3 years ago, with Granite Countertops, Stainless Steel Appliances, and the Interior was Freshly Painted. Be sure to take time to enjoy the view from your Screened Porch. There are No Homes behind you, just open pastures, roaming cows, and trees. Very peaceful. The HOA fee also includes the Landscaping, Lawn Maintenance, Exterior Painting, and Roof (replaced in 2023) for your Villa. This Home allows you to relax and enjoy a game of Golf, take a swim in the Olympic Pool, or just enjoy the view from your Screened Porch. The Home is located close to Shopping (New Publix), Restaurants, Downtown, and Highway 27 which leads to Interstate 4 for Tampa and Orlando (Disney World). Come see what this home can offer you!

Listing is courtesy of: XCELLENCE REALTY, INC (866-595-6025)

Listing Agent: David Shippey (863-521-4517)

Remarks: Under contract-accepting backup offers. This beautifully updated move-in-ready home sits in a quiet, established community on Lake Dexter, one of Winter Haven’s pristine spring-fed lakes. The neighborhood offers an exceptional lifestyle with private access to a residents-only boat ramp, a sparkling saltwater community pool, and a serene waterfront park complete with a fishing dock, gazebo, playground, and shady green space to enjoy year-round. It’s a rare setting—peaceful, well-maintained, and so close to everything that you can even walk to Legoland. Inside, the home feels bright, airy, and inviting, thanks to thoughtful updates and fresh finishes throughout. The layout is comfortable and functional, featuring a spacious primary suite, two additional bedrooms, and two full bathrooms. The third office or bedroom sits just off the kitchen and is framed by French doors, making it the perfect space for a home office, guest room, or flex space to fit your lifestyle. The seller has invested in quality improvements, including a brand-new roof, fresh interior and exterior paint, a new electric water heater, a full water-softening system, updated light fixtures and hardware, refreshed landscaping, a newly rescreened back patio, and recent servicing of both the AC and irrigation systems. The main living areas feature attractive luxury laminate flooring, adding warmth and style, while the screened back porch provides a quiet, private place to relax overlooking the neatly manicured yard. Winter Haven’s central location between Tampa and Orlando puts major attractions, beaches, airports, and dining just a short drive away, making this an ideal full-time residence or a low-maintenance Florida getaway. This charming home truly checks all the boxes for comfort, convenience, and easy Florida living. All measurements are approximate and should be verified by the buyer or buyer’s agent.

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

Listing Agent: Emily Ward (863-632-1865)

Remarks: The property you are inquiring about is located in Winter Haven, FL in the Emerald Acres/Grassy/Lake Estates area of Polk County. This beautiful lakefront, 4+ bedrooms, 2-bath home is situated on over 2 acres on Grassy Lake! Just needs a little TLC and a new owner to enjoy a relaxed lifestyle with a beautiful view! Call, text, and see! *Agents, please read MLS Remarks.*

Listing is courtesy of: BROKERS REALTY OF CENTRAL FLOR (863-294-6773)

Listing Agent: Renee Butler (863-294-6773)

Remarks: The property you are inquiring about is located in Winter Haven, FL, in the Orchid Springs area of Polk County. This is a second-floor unit with 2 bedrooms, 2 bathrooms, and is ready to move into. This is a 55+ community and has a nice square footage for this lifestyle. Many amenities are included in the HOA fee structure - lawn, water, sewer, natural gas, grounds, clubroom. The dishwasher is in as-is condition. This is a secluded area with no noise behind you (maybe a squirrel), but more peace and tranquility. Text, call, email, and see it today! Agents, please see MLS (Realtor) remarks.

Listing is courtesy of: BROKERS REALTY OF CENTRAL FLOR (863-294-6773)

Listing Agent: Renee Butler (863-294-6773)

Remarks: This 3-bedroom, 2-bath home located in the community of Orange Manor West is perfect for settling into an active community for the 55+. The home features metal roof, vinyl siding, carport, outside storage and corner lot. Inside home has a spacious living /dining room combo, a nicely sized open kitchen, inside laundry room, with luxury vinyl and carpet highlights the interior. The community of Orange Manor has an active community with pool, putt putt golf, clubhouse, and other amenities. Located conveniently in Southeast Winter Winter Haven with ease of access to Highway 27. Check this one out today! *Agents, please read MLS remarks.*

Listing is courtesy of: BROKERS REALTY OF CENTRAL FLOR (863-294-6773)

Listing Agent: Renee Butler (863-294-6773)

Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Welcome to 5755 Marsh Landing Drive in Winter Haven, Florida! This spacious 5-bedroom, 3-bathroom home with a loft offers 3,172 square feet under roof is and is priced to sell. Built in 2017 and recently refreshed, this home features new interior and exterior paint, luxury vinyl plank flooring and tile throughout. The kitchen features new stainless-steel appliances, huge cabinets, and a functional design overlooking the main living area. The spacious primary suite offers two large walk-in closets and a private en suite, while the additional bedrooms and upstairs loft provide flexible space for family, guests, a home office, game room, or media area. Additional updates include a 2026 roof, updated lighting, and trendy new hardware. Outside, enjoy the amazing benefit of no rear neighbors, giving the backyard a more open and peaceful feel. Conveniently located in Winter Haven, this home offers easy access to shopping, dining, schools, medical facilities, and the area’s Chain of Lakes. This move-in-ready home combines space, updates, and location — schedule your private showing today!

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

Listing Agent: Jason Stone (863-838-8972)

Remarks: WONDERFUL POOL HOME IN GATED COMMUNITY Located in Ruby Lake subdivision, this spacious home boasts appealing architectural enhancements with high ceilings throughout its 2,648 sq.ft. of living area. The layout features an open concept design with a formal living room, formal dining room, large family room and a split-plan for the 4 bedrooms and 3 full baths. The centrally located kitchen offers plenty of beautiful wood cabinets and granite counter space along with the conveniences of a pantry, breakfast bar and a dinette giving great view of the outdoor living space and pool. The generous family room has sliding glass doors to the lanai & pool and stands open to the dinette and kitchen. The seamless transition between the kitchen, formal living and dining rooms, and the casual living areas is perfect for daily life and when hosting get-togethers. The master en suite features a generous bedroom with sliding glass doors to the lanai, walk-in closet, and the bathroom has dual vanities, a soaking tub, walk-in shower, and water closet. The second bathroom stands convenient to the additional bedrooms and living areas and the third bathroom stands convenient to the pool area. This great Central Florida location is near shopping, schools, medical facilities and restaurants with easy access to both Tampa and Orlando.

Listing is courtesy of: 1513 REALTY LLC (863-431-2000)

Listing Agent: Pedro Cartagena (863-528-2376)

Remarks: Beautiful and spacious family home with room for everyone to spread out and enjoy. Featuring over 2,400 square feet of living space, this home offers a warm and functional layout perfect for everyday living, entertaining, and creating lasting memories.??The open kitchen and living area serve as the heart of the home, complete with granite countertops, stainless steel appliances, abundant cabinet space, and a large breakfast bar where family and friends naturally gather. Natural light fills the home, while updated finishes and modern touches create a comfortable, move-in-ready feel.??One of the home’s standout features is the oversized bonus room — ideal for a playroom, media room, home office, homeschool space, gym, or second family room. The flexible layout allows the home to grow with your family’s needs.??Outside, the spacious yard offers endless potential for kids, pets, entertaining, gardening, or even adding a future pool. With no HOA, you have the freedom to truly make the property your own.?Conveniently located near schools, shopping, restaurants, and everything Winter Haven has to offer, this is a wonderful opportunity to own a great family home with space, flexibility, and value.*Agents, please read MLS realtor remarks.*

Listing is courtesy of: BROKERS REALTY OF CENTRAL FLOR (863-294-6773)

Listing Agent: Renee Butler (863-294-6773)

Remarks: Under contract-accepting backup offers. 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. Welcome to this 4-bedroom, 2-bath home located in the desirable gated community of Krenson Bay. Featuring a bright and open split floor plan, this home offers ceramic tile flooring throughout the main living areas, a spacious 2-car garage, and a fenced backyard for added privacy. The split bedroom layout provides comfort and seclusion, with a generous primary suite complete with a walk-in closet and en-suite bath. The covered patio and sizable backyard make it easy to enjoy Florida living—whether relaxing, entertaining, or playtime in the yard. Perfectly situated, this home is just minutes from downtown Winter Haven, where you can browse the Saturday Farmers Market or enjoy world-famous water ski shows on Lake Silver. Polk State College is within walking distance, and you’ll also be close to restaurants, medical centers, and everyday conveniences like Publix. With no CDD and a low HOA, you’ll enjoy neighborhood security and amenities without the extra cost. Commuters will love the quick access to Hwy 27, providing an easy drive to area beaches, Orlando’s theme parks, and more. Nestled in a quiet, well-maintained neighborhood, this home is also near Legoland, top-rated schools, parks, and scenic lakes—an ideal location for a vibrant Central Florida lifestyle.

Listing is courtesy of: RE/MAX 200 REALTY (407-629-6330)

Listing Agent: Mike Rance (407-629-6330)

Remarks: Welcome to SPRING LAKE TOWERS, a premier 55+ community in Winter Haven, Florida offering a relaxed lakefront lifestyle with this well-maintained 2-bedroom, 2-bath condo featuring an open floor plan with stunning lake views, a 12' x 22' great room connected to the kitchen via convenient pass-through, spacious 12' x 18' Primary suite with private bathroom and walk-in closet, 10' x 13' second bedroom adjacent to guest bathroom with tub/shower, and a versatile 7' x 23' Florida room perfect for home office, hobbies, or relaxation. The all-inclusive condo fee covers cable TV, internet, water, sewer, trash removal, building maintenance (exterior, roof, insurance), reserve funds, common area upkeep, on-site management, and access to all community amenities including swimming pool, exercise room, recreation room with kitchen, library, game area, shuffleboard, laundry facilities, and active social calendar with enhanced security features. Situated on the "Chain of Lakes" for fishing, boating, and water activities with boat slips available for a reasonable fee (verify with management), this property boasts a rare assigned covered parking space in close proximity to the unit and is adjacent to Northgate shopping plaza featuring Publix, restaurants, and services, minutes from medical facilities, Winter Haven Hospital, places of worship, and downtown. No pets or smoking permitted. This perfect full-time residence or seasonal retreat (measurements approximate, information believed accurate but not guaranteed).

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

Listing Agent: Kevin Tison (863-206-5755)

Remarks: Under contract-accepting backup offers. PRICE REDUCTION!!! MOTIVATED SELLER!!! Discover this exceptional income-producing property perfectly situated on a spacious 0.48-acre lot in the heart of Winter Haven. This versatile property features two separate living spaces, one currently rented—providing immediate income and excellent long-term investment potential. The main home which is now vacant and ready for it's new owners or tenants offers 3 bedrooms and 2 bathrooms, including a generous master suite with an en-suite bath. The open and functional layout makes it ideal for families or long-term tenants. Attached to the main residence is a 484 sq. ft. in-law suite currently rented, complete with a full kitchen, bedroom, bathroom, and private entrance. This flexible space can serve as an additional rental unit, private guest quarters, or be seamlessly integrated into the main living area for multi-generational living. This home was recently appraised above the asking price, giving buyers instant equity and outstanding value. Whether you’re an investor seeking steady cash flow or a homeowner looking for flexibility, this property is a rare find. Take advantage of strong rental demand, potential appreciation, and the benefits of owning in one of Florida’s fastest-growing counties, consistently rated among the best places to live. Don’t miss your chance to own this unique multi-unit property—schedule your private showing today!

Listing is courtesy of: BRIGHT REALTY (941-552-6036)

Listing Agent: Jen Victor (941-587-2787)

Remarks: Under contract-accepting backup offers. Welcome to 1033 Sawgrass Dr, where modern comfort meets thoughtful upgrades in this beautifully maintained 3-bedroom, 2-bath home. Designed with everyday living in mind, this home features an open-concept layout filled with natural light, creating a bright and inviting space perfect for both relaxing and entertaining. The kitchen offers quality finishes and a clean, contemporary feel, seamlessly connecting to the main living area. Elegant crown molding adds a refined touch, while plantation shutters provide both style and function throughout the home. The primary suite offers a spacious retreat, complete with a large walk-in closet for ample storage. Outside, the widened driveway adds extra convenience and functionality—an upgrade you’ll appreciate daily. Located in the highly sought-after Lake Ashton community, residents enjoy access to an impressive array of amenities designed for an active and social lifestyle. From two 18-hole golf courses to expansive clubhouses, fitness centers, indoor and outdoor pools, and courts for tennis, pickleball, bocce, and more, there’s always something to do. Additional features include a bowling alley, movie theater, arts and crafts spaces, pet areas, and a full calendar of community events. Positioned in Central Florida with convenient access to both Tampa and Orlando, this property offers the perfect balance of comfort, convenience, and lifestyle.

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

Listing Agent: Veronica Bard (863-670-7526)

Remarks: SPACIOUS & AFFORDALE IN SOUTHEAST WINTER HAVEN, THIS 3BR/2BATH home features newer vinyl plank flooring throughout, brand new dishwasher just installed and newer kitchen cabinets! The great room has beautiful dark beams on the ceiling that give the room so much more character. Sliding glass doors open to the 10x23 screened-in patio and partially fenced & spacious rear yard for pets. Adjacent to the kitchen is an extra room, could be great for an office/den space for those who work from home. On the other side of the living area, you'll find 3 bedrooms and a guest bath with tub/shower. The primary bedroom has a walk-in closet with an en-suite bath with walk-in tiled shower. There is an oversized 1-car garage with workshop area and plenty of shelving. Located near the Lake Ned public boat ramp with kid's playground & basketball court! Great location with quick in-town access!!

Listing is courtesy of: THE K TEAM REAL ESTATE SERVICES LLC (863-604-1601)

Listing Agent: Cathy Kluytenaar (863-604-6220)

Remarks: Looking for the perfect starter home or turnkey investment? Welcome to 117 4th Ave N! This well-maintained 3-bedroom, 1.5-bath home has been lovingly cared for by the same family for over 40 years and is now ready for its next chapter. Situated just minutes from shopping and dining, this property delivers both comfort and convenience in the heart of Winter Haven. Recent updates include a brand-new roof (2025), providing peace of mind and long-term value. For investors, current tenants are interested in staying—offering an immediate income opportunity if desired. Inside, you'll find an open and inviting floor plan where the kitchen flows seamlessly into the spacious living room. Each bedroom offers generous space with nice-sized closets, perfect for growing families or long-term renters. But here's the bonus: attached to the back of the home is additional flex space not included in the square footage. This area could easily be converted into a 4th bedroom, mother-in-law suite, home office, or studio—adding even more value and versatility to the property. Parking is another standout feature with a covered carport plus a detached garage—ideal for extra vehicles, storage, or workshop space. Priced to sell and brimming with potential, this gem won't last long.

Listing is courtesy of: FIVE STAR REAL ESTATE OF FLORIDA LLC (904-539-3336)

Listing Agent: Arina Reid-Martin (770-500-0514)