Winter Haven Single Family Homes For Sale - 756 homes

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: Under contract-accepting backup offers. Beautiful 4 bedroom, 2 1/2-bathroom, pool home with new roof (2024), septic (2024), A/C (2025) in gated Overlook Estates. Fresh price reduction, bring your offers! Experience the pinnacle of Florida living in this exceptional pool home, offering 2,850 sq ft of light-drenched space in the established Overlook Estates neighborhood, where privacy and prestige define the community. This is the rare opportunity you've been waiting for: a spacious, ultra-private luxury home in a top-tier location. Schedule your showing today and make this dream residence yours before it's gone.

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

Listing Agent: Brian Surrency (863-204-4298)

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: 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: This 3-bedroom, 2-bath home located conveniently close to the Polk Parkway for ease of travel throughout Central Florida, is a great home! It features a roof that is less than 3 years old, fenced yard, detached garage, and a covered porch. Inside the home features split bedrooms, stainless steel appliances, inside laundry room, ceramic tile and vinyl throughout the house, and eat-in kitchen. This home comes with a water softener and NO HOA for extra convenience. Call today for your private showing. *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: This dynamically unique home in Winter Haven offers waterfront living, with direct access to the renowned Chain of Lakes. Ideally situated on Lake Cannon, the property delivers stunning water views and a peaceful setting that’s hard to match. Located within a gated, low-maintenance community, this home allows you to enjoy all the perks of ownership without the added upkeep. The community pool and hot tub sits just steps away—offering the feel of a personal pool without the responsibility. Residents also enjoy access to a community dock with first-come, first-served boat slips, making it easy to embrace the lake lifestyle. The property itself features a fenced yard, and a beautiful pergola—perfect for relaxing, entertaining, or enjoying the serene lakefront setting. The garage is equipped with a 2021 split-unit AC system, creating a versatile space ideal for a workshop, gym, or even additional living area. For added peace of mind, the home includes a gas-powered generator that automatically kicks on when needed. Inside, the home is nothing short of impressive—boasting soaring cathedral ceilings, expansive balconies with breathtaking views, and a layout that is both majestic and thoughtfully designed. The primary suite is a true retreat, featuring a private balcony, dual vanities, and a luxurious soaking tub designed for relaxation. Additional office and bonus spaces offers flexibility and can easily be converted into extra bedrooms to fit your needs. Updates include two AC units installed in 2017, along with a durable metal roof added in 2021 and the roof tiles were sealed and coated for an extra long life. Whether you’re looking for a full-time residence, a seasonal getaway, or a place to gather with family and friends, this home delivers a warm, inviting atmosphere with unique architectural character throughout. Enjoy peaceful mornings overlooking the lake, afternoons gardening in your yard, or evenings unwinding on the balcony while taking in the surrounding wildlife. Conveniently located near shopping, grocery stores, and Home Depot, this is more than just a home—it’s a lifestyle. A property like this must be seen in person to truly appreciate the grandeur and exceptional living experience it offers.

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

Listing Agent: Keith St. Onge (863-651-1397)

Remarks: One or more photo(s) has been virtually staged. Meet 2234 Avenue B NW, a residence recently enhanced by fresh interior paint and a partial flooring replacement. A functional fireplace enhances the living area, and an exterior storage shed provides practical utility. The property also includes a well-defined fenced in backyard. Thoughtful updates and practical features make this a must-see.. Included 100-Day Home Warranty with buyer activation

Listing is courtesy of: OPENDOOR BROKERAGE LLC (480-462-5392)

Listing Agent: Karen Albright (480-462-5392)

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: 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)

Remarks: Short Sale. Bank approved price! Welcome to this beautifully updated 4-bedroom, 1.5-bath single-family home located in Winter Haven with NO HOA! This solid block construction home offers peace of mind with a new roof and AC installed in 2024. Inside, you’ll find newer flooring throughout along with a recently renovated kitchen and bathrooms, giving the home a fresh, modern feel. The kitchen features quartz countertops, stainless steel appliances, and updated cabinetry, perfect for both everyday living and entertaining. The functional layout includes four spacious bedrooms, a full bathroom, and an additional half bath for added convenience. Enjoy outdoor living in the fully fenced backyard, ideal for pets, gatherings, or simply relaxing in your private space. The home also includes a 1-car garage for storage and parking. Ideally situated near Lake Conine, part of Winter Haven’s famous Chain of Lakes, this property offers easy access to boating, fishing, and outdoor recreation. Conveniently located near major roadways, providing a quick commute to Orlando, Tampa, and world-renowned attractions like Disney. This move-in ready home combines modern updates, a great location, and no HOA restrictions—don’t miss your opportunity to make it yours!

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

Listing Agent: Garrett Robinson (863-838-5210)

Remarks: *** No CDD fees!!***Welcome to this stunning smart home offering the perfect blend of modern design, space, and functionality. This impressive two-story residence features 5 bedrooms, 3 full bathrooms, and a spacious 3-car garage, making it ideal for growing families or those who love to entertain. Step inside to discover a bright and open floor plan designed for today’s lifestyle. The main living areas flow seamlessly, creating the perfect space for gatherings, while large windows bring in abundant natural light. The modern kitchen serves as the heart of the home, featuring sleek finishes, ample cabinetry, and generous counter space for cooking and entertaining. With five generously sized bedrooms, there’s room for everyone—including a flexible space for guests, a home office, or multi-generational living. The primary suite offers a private retreat with a well-appointed en-suite bathroom and plenty of closet space. This home is equipped with smart home technology, providing convenience, efficiency, and peace of mind at your fingertips.Step outside and enjoy your own private outdoor retreat situated on a generous 0.24-acre lot, offering plenty of space for relaxation, play, or future customization. The covered back patio and screened enclosure create the perfect setting for year-round outdoor living—ideal for morning coffee, evening gatherings, or simply enjoying Florida’s beautiful weather without the bugs. Built in 2023, this home offers the advantages of newer construction without the wait, combining modern features with move-in ready convenience. Home is just minutes from Legoland and the sea life aquarium! Don’t miss the opportunity to own this beautifully designed home—schedule your private showing today!

Listing is courtesy of: JASON MITCHELL REAL ESTATE FLO (754-307-0607)

Listing Agent: David Hartigan (407-955-1156)

Remarks: Under contract-accepting backup offers. Price Reduced. Excellent Investment Opportunity. Zoning MX district. Seller Motivated. Recived $10,000 toward buyers closing cost. Charming Colonial Home — Elegantly Renovated in Central Winter Haven. Welcome to timeless charm blended with modern comfort in this beautifully Colonial residence, perfectly situated in the heart of Winter Haven, Florida. Meticulously updated while honoring its historic character, this home offers the ideal blend of classic architectural details and contemporary living. As you approach, you’re greeted by a stately façade showcasing symmetrical Colonial proportions, a welcoming front porch, and original period craftsmanship that has stood the test of time. Current zoning classification is MX (Mixed-Use), which allows a wide range of commercial and residential uses. Typical permitted uses examples are: Professional and medical offices, Assisted living facilities, ALF) / senior care, Group homes and supportive housing, Multifamily residential buildings, Live/work units and mixed commercial-residential developments.

Listing is courtesy of: CENTRAL REALTY GROUP AND PROPERTIES (407-582-9011)

Listing Agent: Raul Briceno (407-715-2550)

Remarks: PRICE REDUCTION! WELCOME TO YOUR NEW HOME! Experience peaceful lakefront living in a charming SE Winter Haven location, just minutes from LEGOLAND Florida Resort and the beautiful Chain of Lakes. This home is perfect for buyers looking to slow down and enjoy the simple things—morning coffee with a water view, evenings by the lake, and weekends spent fishing or unwinding in your own backyard. While the lake is smaller and offers a more quiet setting with no public boat access, that’s part of its charm—less traffic, more tranquility. Situated on a spacious lot with a fenced backyard, there’s plenty of room for pets, gatherings, or creating your own outdoor oasis. Inside, the home offers a solid foundation and a warm, inviting layout, ready for your personal style and updates to truly make it your own. If you’ve been searching for an affordable lakefront lifestyle with room to grow, this is your opportunity to put down roots and create a home that reflects you.

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

Listing Agent: Lamanda Jones (863-557-3627)

Remarks: Under Construction. The Archer II is one of our one-story floorplans features in our Willowbrook South community in Winter Haven, Florida. Take your pick between two sleek exterior options when choosing this floorplan. Inside this 3 bedroom, 2 bathroom home you’ll find 1,328 square feet of comfortable living. The open concept layout allows for seamless movement between spaces making entertaining guests a breeze. It also provides homeowners versatile design options. The kitchen features shaker-style cabinets, quartz countertops, and stainless steel appliances, which are sure to both turn heads and make meal prep easy. You’ll bever be too far from the action with the living and dining area right there. In every bedroom, besides the primary bedroom, you’ll have carpeted floors and a closet in each room. Whether these rooms become bedrooms, office spaces, or other bonus rooms, there is sure to be comfort. The primary bedroom features luxury vinyl plank flooring that will be sure to stand out. It also has its own attached bathroom that features a walk-in closet and all the space you need to get ready in the morning. Sharing a sink isn’t a worry with the double vanity, and you also get additional privacy with a separate door for the toilet and shower. Contact us today and find your home at Willowbrook South.

Listing is courtesy of: DR HORTON REALTY OF CENTRAL FLORIDA LLC (407-250-7299)

Listing Agent: Paul King (407-519-3940)