Winter Haven Single Family Homes For Sale - 748 homes

Remarks: Completely renovated and move in-ready Large 4 bedroom, 2 bathroom house awaits your family! On a desirable corner lot, in a quiet neighborhood. New Roof, New Paint, New Flooring all through the house, New Stainless Steel Appliances, New Kitchen Faucet, Like a New Home!! Master Bath has a walk in closet and Garden Tub and Seperate Shower with a Seat. This home offeres a Separate Dining area and a Office or Playroom. Close to the new Polk Parkway extension, so travel to schools, shopping, restaurants and entertainment is super convenient. Great school district and priced to sell quickly. Call today for a showing!

Listing is courtesy of: AVERY PROPERTIES INC. (863-682-1902)

Listing Agent: Anne Greenhow (863-698-4562)

Remarks: Motivated seller alert! USDA financing eligible for qualified buyers! Welcome to 6006 Country Walk Lane in Winter Haven, where space, privacy, and value come together. This beautifully maintained 4-bedroom, 2-bath home offers 1,809 square feet of comfortable living on an expansive 0.36-acre fully fenced lot in the established Country Walk community with low HOA dues of just $29 a month. Major updates have already been completed, including a roof replaced in 2023, brand-new stainless steel dishwasher, water softener system, and a new back door with built-in doggy door. The home features a desirable split floor plan for added privacy and no carpet throughout, creating a clean, low-maintenance living environment. A 10x16 storage shed and spacious backyard provide plenty of room to entertain, garden, or even add a pool. Unlike nearby new construction, this property offers land, privacy, and an established neighborhood setting without the wait. The sellers are highly motivated and willing to contribute toward buyer closing costs. Don’t miss this opportunity to secure one of the best lot values in Winter Haven. You’ll appreciate the thoughtful upgrades throughout—no carpet anywhere, a split floor plan for added privacy, and recent improvements designed for easy living, including a brand-new stainless-steel dishwasher, Maytag soft-water system, new back door with built-in doggie door, 10×16 storage shed, fully fenced yard, and even a hot tub—perfect for relaxing on those warm Florida evenings. Situated on a spacious 0.36-acre lot with low HOA dues of just $29/month, this move-in-ready home offers room to breathe while remaining conveniently close to the Polk Parkway, providing easy access to both Tampa and Orlando. Homes with this combination of space, upgrades, and incentives. Schedule your private showing today and experience why Country Walk living truly feels like Florida bliss!

Listing is courtesy of: RE/MAX HERITAGE PROFESSIONALS (863-256-2188)

Listing Agent: Anna Impiduglia (407-861-6223)

Remarks: REMODELED! LOW HOA FEE! This 4-bedroom, 3.5-bath home is located in a desirable Winter Haven area and shows like a model. Recent upgrades include new 100% waterproof luxury vinyl flooring throughout the entire home, fresh interior and exterior paint, and epoxy countertops in the kitchen and all bathrooms. The first floor features formal living and dining areas, perfect for entertaining along with an open-concept kitchen, laundry room, and a spacious family room ideal for relaxing. The kitchen is equipped with a chef's island and built-in features, offering ample storage and prep space. Upstairs, you'll find a large loft area that can serve as a home office or additional living space. The second floor also includes three secondary bedrooms, including a generous junior suite with its own private bathroom and large closet, plus an additional shared bathroom. The oversized master suite offers two walk-in closets and a luxurious bathroom with a garden tub and separate shower. Conveniently located near I-4 and Hwy 27, this home provides easy access to shopping, schools, restaurants, medical facilities, and Legoland. Move-in ready and A must-ses!

Listing is courtesy of: CENTURY 21 CARIOTI (407-573-2121)

Listing Agent: Sandy Ou (407-573-2121)

Remarks: Discover lakeside living at Willowbrook North in Winter Haven, where modern single-family homes meet scenic Florida charm. Nestled near beautiful Lake Fannie and adjacent to the Willowbrook Golf Course, this boutique community offers thoughtfully designed homes with open-concept layouts, energy-efficient features, and stylish finishes. Residents enjoy convenient access to Hwy 27, Downtown Winter Haven, shopping, dining, entertainment, and the new Haines City Target & Crossroads Village. Community highlights include low HOA fees, scenic surroundings, and select homesites with water views. Experience comfort, convenience, and connectivity in one of Winter Haven’s most desirable new home communities.

Listing is courtesy of: DRB GROUP REALTY, LLC (407-270-2747)

Listing Agent: Adam Schott (407-270-2747)

Remarks: Welcome to 5445 Chandler in Winter Haven—a great opportunity for buyers looking to add their own personal touch! This home offers generous square footage and plenty of living space, giving you room to spread out, entertain, or reimagine the layout to fit your needs. The property has already seen some key updates, including a brand-new roof and fresh interior paint, providing a solid foundation for future improvements. Inside, you’ll find a functional layout with large living areas and ample space, making it ideal for those seeking both comfort and potential. While the home could use some additional updates and TLC, it presents an excellent chance for homeowners or investors to build equity and truly make it their own. Conveniently located near shopping, dining, and Winter Haven’s beautiful lakes, this property offers both space and opportunity. If you’re looking for a home with room to grow and the ability to add value, this is one you won’t want to miss!

Listing is courtesy of: TRANSCEND REALTY (407-518-7653)

Listing Agent: Jacob Hara (407-933-5478)

Remarks: Short Sale. Lender has provided preliminary net guidance based on a recent appraisal. Offers will be reviewed in accordance with lender and VA guidelines. Buyer is encouraged to submit highest and best offer. Final approval subject to lender review.This is the kind of home that just feels right the moment you pull in. Set on an oversized .29-acre lot with no rear neighbors and peaceful conservation views behind you, this spacious 4-bedroom, 2-bath home offers room to breathe, grow, and truly settle in. Inside, you’ll find more than 2,200 square feet of comfortable living space—plus a converted garage that gives you even more flexibility. Need a fifth bedroom? A home office? A workout room or game space? This home easily adapts to whatever stage of life you’re in. The heart of the home is the open kitchen, breakfast nook, and family room, designed for everyday living and easy entertaining. Large windows over the kitchen sink flood the space with natural light, while ample cabinetry and a charming barn-door pantry add both function and personality. The living room’s feature wall gives the space character, and luxury vinyl flooring throughout keeps things both stylish and practical. Every bedroom has ceiling fans, making the home comfortable year-round. One of the hidden gems here is the oversized laundry room—complete with built-in cabinets and direct access to the backyard—perfect for storage, projects, or keeping life organized. Major updates mean peace of mind: newer windows and sliding glass doors, updated insulation, a replaced sewer line, newer appliances, a 2021 roof, and solar panels installed in 2022. Even better? The solar panels often result in credits from the power company, helping keep monthly utility costs surprisingly low. Step outside and you’ll see where this home really shines. The backyard feels private and inviting, with a large screened porch, fire pit for cozy evenings, and two storage sheds for all your tools and toys. Whether you’re hosting friends, enjoying a quiet morning coffee, or winding down after a long day, there’s space here to enjoy Florida living your way. The wide driveway easily fits four or more vehicles, making gatherings easy. Located in a quiet non-HOA neighborhood, you’ll enjoy the freedom to live how you want—no HOA or CDD fees—while still being close to shopping, dining, schools, and local attractions. And if you love boating or an active outdoor lifestyle, you’ll appreciate the flexibility this neighborhood offers. This home isn’t just about square footage or upgrades—it’s about comfort, flexibility, and the feeling of finally finding the one. Come see it in person and imagine the life you could build here.

Listing is courtesy of: WATSON REALTY CORP. (407-589-1600)

Listing Agent: Katie Sweet (863-990-5141)

Remarks: Welcome to this FULLY renovated, beautiful and large 3Bed 2bath home in Winter Haven!! Property has been fully renovated to 2026 standards in and out. Fresh pain in and out. Brand new 6" baseboards throughout the home. Crown molding throughout the main living space. Brand new water resistant LVP tile. Pool has been repainted. Walls have been refreshed and smoothened out. Popcorn ceiling through the main home has been sanded down and smoothened. Garage has been given a fresh coating of pain and the floors smoothened. Both Florida rooms have been renovated as well. Roof (2020) A/C (2020) New Water-heater installed (2026) Stainless Steel Samsung Dishwasher (2026) Stainless Steel Samsung Fridge (2026) Stainless Steel Whirlpool Electric Range (2026) Stainless Steel Broan-NuTone Range Hood (2026). Solar Panels are fully owned. Full 3D property walk-through video available upon request. PLEASE NOTE - I AM NOT AVAILABLE ON THE SABBATH/SATURDAYS

Listing is courtesy of: CARDINAL REALTY GROUP, LLC. (305-910-2902)

Listing Agent: Meir Tenenbaum (305-721-7408)

Remarks: One or more photo(s) has been virtually staged. **Seller offering $5,000 toward closing costs.** 2020-built 4BR move-in ready home in Winter Haven with appliances included! Modern comfort meets everyday convenience in this well-maintained, open-concept home featuring a s floor plan, spacious living areas, and a true turnkey setup. Enjoy a fully equipped kitchen with refrigerator, stove, dishwasher, plus washer & dryer included for ad value. Recent updates include new carpet in select bedrooms, and an irrigation system keeps the yard looking great with minimal effort. The private primary suite offers a walk-in closet and full bath, while three additional bedrooms provide flexibility for family, guests, or a home office. Built in 2020, this home offers the benefits of newer construction-lower maintenance, modern systems, a efficient living—all in a convenient Winter Haven location close to shopping, schools, dining, and major roadways. Move-in ready and priced for today's market-don't miss this opportunity.

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

Listing Agent: Roderick Small (863-712-0657)

Remarks: Welcome to this charming 2 bedroom, 2 bathroom home in Orchid Springs, a non–age-restricted community where all ages are welcome, located in SE Winter Haven. Thoughtfully updated, this home features new wood plank tile flooring. The open floor plan is highlighted by a spacious and light-filled great room with vaulted ceilings creating a warm and inviting space ideal for everyday living. Just off the great room is a beautiful atrium to fill with your favorite plants or enjoy the evenings outside in your private sanctuary. The primary suite includes built-in closets, sliding glass door open to the back courtyard and an en-suite bathroom with updated wood plank tile flooring, updated vanity and mirror the secondary bedroom is generously sized and located next to the guest bathroom, which features updated vanity and tile flooring. Additional highlights include a one-car garage with laundry area Outdoors, enjoy a paver patio courtyard ideal for BBQs and entertaining. There are plenty of private outdoor spaces for relaxing there is are front and rear screened porches as well as the outdoor courtyard. Orchid Springs is a well-established community offering a swimming pool and clubhouse, with lawn maintenance and amenities included for a low monthly fee. Conveniently located within minutes of shopping, dining, medical facilities, and LEGOLAND® Florida, and centrally positioned between Tampa and Orlando for easy access to theme parks and international airports. Call today to schedule your private showing.

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

Listing Agent: Anita Lowe (863-269-6461)

Remarks: Beautifully updated home located in the heart of Winter Haven! This charming property features 2 bedrooms, 1 bathroom, plus a versatile bonus room with an additional bathroom — perfect for guests, a home office, playroom, or extra living space. The home has been thoughtfully upgraded with a NEW ROOF, updated electrical installation, modern kitchen improvements, and NEW flooring throughout, offering comfort and peace of mind for future homeowners. The bright and welcoming interior creates the perfect blend of charm and functionality. Step outside and enjoy a prime location just minutes from Downtown Winter Haven, restaurants, shopping centers, schools, and major highways. One of the standout features of this home is its proximity to the beautiful Winter Haven Recreation Center, located right behind the property, offering basketball courts, sports fields, recreational activities, and outdoor spaces to enjoy with family and friends. The area also offers nearby parks, lakes, and entertainment that make Winter Haven one of Central Florida’s fastest-growing communities. Conveniently located near LEGOLAND Florida and within driving distance to Disney and Orlando attractions, this property is perfect for first-time buyers, families, or investors looking for a move-in-ready opportunity with excellent location benefits. A bonus room and an additional bathroom may not be reflected in public records. Buyer to verify all measurements, permits, and property information. Property sold AS-IS.

Listing is courtesy of: COLDWELL BANKER REALTY (407-352-1040)

Listing Agent: Vivian Correa (401-263-5921)

Remarks: Under Construction. The Astor is one of our one-story floorplans featured in Harmony at Lake Eloise in Winter Haven, Florida. With 3 exteriors to choose from, the Astor is sure to turn heads. Inside this 3 bedroom, 2 bathroom home, you’ll find 1,565 square feet of comfortable living. This home offers a two-car garage and covered porch in the rear of the home. As you enter, you're greeted with a spacious living area, coat and linen storage closets and dedicated laundry room. The kitchen located in the center of the home features quartz countertops, an island, stainless steel appliances and a pantry. You’ll never be too far from the action with the living and dining area to the immediate left and right. The primary bedroom has an attached bathroom that features a walk-in closet, double sink vanity and all the space you need to get ready in the morning. Every bedroom features carpeted floors and a closet. Whether these rooms become bedrooms, office spaces, or other bonus rooms, there is sure to be comfort. Like all homes in Harmony at Lake Eloise, the Astor includes all concrete block and also smart home technology, which allows you to control your home anytime with your smart device while near or away. Contact us today and find your home at Harmony at Lake Eloise. *Photos are of similar model but not that of the exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability, and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

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

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

Remarks: PRICE ADJUSTMENT***Don't Miss This Opportunity! This home offers amazing potential and features 4 bedrooms and 1 full bath, making it ideal for homeowners or investors. The kitchen is just off from the spacious dining area, great for family gatherings, while the spacious living room and family room provides extra space to relax. The primary bedroom as well as the other rooms are generously sized, offering a built-in closets. This home is a great candidate to be transformed into your ideal living space or added to your rental portfolio. Property is being sold As-Is. All buyers MUST view the home in person before submitting an offer. Opportunities like this don't last long, schedule your showing today before it's gone! ** FURNISHINGS, WASHER, DRYER, OR REFRIGERATOR DOES NOT CONVEY WITH THE SALE OF HOME.

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

Listing Agent: Twanna Dewdney (863-207-1634)

Remarks: SELLER MOTIVATED!! Welcome to an exceptional opportunity in Lake Ashton West, where refined elegance meets effortless resort-style living. This highly upgraded 3-bedroom, 2-bath St. John floor plan—with a versatile office or additional living space—offers a residence that is nothing short of breathtaking. From the moment you arrive at the beveled double French glass door entry, a sense of sophistication unfolds. Inside, the home reveals impeccable craftsmanship at every turn—graceful round columns frame the formal dining area, while raised archways seamlessly guide you into the heart of the home. The great room is a true showpiece, highlighted by coffered ceilings with recessed lighting, crown molding, and expansive 8-foot triple sliders that invite natural light to pour in while opening to the lanai. The kitchen is designed to impress and perform, featuring 42-inch raised-panel custom cabinetry with crown molding, gleaming granite countertops, stainless steel appliances, pendant lighting, and an abundance of drawer storage. A breakfast bar and adjoining nook create the perfect setting for both casual mornings and elegant entertaining. Thoughtfully designed with a split-bedroom layout, privacy is paramount. The primary suite is a tranquil retreat, offering serene views and direct lanai access. The en-suite bath elevates daily living with dual walk-in closets, double vanities, a soaking tub, a walk-in shower, and a dedicated linen closet. Step outside to the expansive screened lanai, where sweeping views of the 13th hole, a peaceful pond, and surrounding nature create a picturesque backdrop for relaxation or gathering with friends. Every inch of this home reflects meticulous care—this is a property that has been exceptionally maintained, offering peace of mind with no concerns awaiting its next owner. Beyond the home, Lake Ashton delivers an unparalleled lifestyle. This premier 55+ golf community is rich with amenities, including a movie theatre, bowling alley, pickleball, tennis, bocce courts, fitness centers, pools, dog parks, and two beautifully appointed clubhouses. Enjoy access to fishing, a private marina, boat ramp, and the security of 24-hour guard-gated entry with private roads. The Health and Fitness Center further enhances the experience with an indoor pool, sauna, racquetball, and basketball courts. Endless clubs, social events, dances, and entertainment ensure there is always something to enjoy. With a newer roof installed in 2021 and all appliances included, this home is move-in ready and waiting to be enjoyed. Opportunities like this do not linger—schedule your private showing today and experience firsthand why this home stands apart.

Listing is courtesy of: HEROES REAL ESTATE GROUP LLC (407-947-6420)

Listing Agent: Armando Perez (407-947-6420)

Remarks: Under contract-accepting backup offers. Versatile corner-lot property just minutes from LEGOLAND, offering multiple use possibilities. The main home features 3 bedrooms and 2 baths, plus an attached flex room with water, air, and electric—ideal for a studio, hobby space, or office. A detached approx. 1,200 sq ft building includes central heat/air, water, electric, and a half bath—excellent for a workshop, creative space, or to explore conversion potential with added walls, a kitchen, and a full bath (buyer to verify). An additional detached approx. 600 sq ft building with electric and wall A/C, plus three storage sheds, provide abundant space for projects and storage. Property needs a new roof and interior updating—bring your vision and add value. Convenient location near shopping, dining, and attractions.

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

Listing Agent: Sarah Armstrong (863-287-0252)

Remarks: Discover this unique Spanish/Mediterranean-inspired estate on an oversized lot across from Lake Jessie on the Chain of Lakes. Featuring a 3BR/2BA main home plus a private 1BR/2BA casita/in-law suite, this property is ideal for multi-generational living, vacation rentals, or income-producing opportunities. The versatile floor plan provides the flexibility to function as a triplex-style investment property. Recent upgrades include a NEW roof, NEW AC, NEW water heater, new casita flooring, and more. Inside, enjoy vaulted ceilings, a fireplace, abundant natural light, and spacious living areas designed for entertaining. Step outside to a resort-style screened saltwater heated pool with new heating, cooling, and saltwater systems. Located on a quiet street with no rear neighbors and NO HOA, there’s plenty of room for boats, RVs, and extra vehicles—just steps from the community boat ramp on Lake Jessie. A rare blend of privacy, flexibility, and investment potential. Don't miss this opportunity! Book your appointment today.

Listing is courtesy of: META ONE REALTY GROUP LLC (407-223-3678)

Listing Agent: Aline Oliveira (407-300-7123)

Remarks: Under contract-accepting backup offers. LEASE to OWN option available!!! Welcome to a home that checks the boxes and adds a little personality along the way! Located at 3396 Ave U NW in Winter Haven, this beautifully remodeled 4-bedroom, 2-bath residence is move-in ready and waiting for its next chapter. Step inside and you’ll immediately notice the fresh updates throughout—because let’s be honest, no one wants a “project” unless it’s on a vision board. This home features a brand-new roof, HVAC system, and windows, water heater, granite countertops, stainless steel appliances, cabinets + more, giving you peace of mind and energy efficiency from day one. Translation? Less worrying, more living. The layout offers flexibility for a variety of living arrangements, including a separate entrance that opens the door to endless possibilities—whether you’re thinking guest suite, private office, creative studio, or simply a little extra breathing room. You decide how it fits your lifestyle. Outside of the home, the location delivers convenience and entertainment all in one. You’re just minutes from LEGOLAND, perfect for fun-filled weekends or hosting out-of-town guests. Nearby, you’ll find a variety of dining options, shopping centers, and everyday essentials to make life easier. Access to quality healthcare is close by as well, including Winter Haven Hospital, giving added peace of mind when it matters most. Whether you're looking for space to grow, room to host, or simply a place that feels like home the moment you walk in—this one delivers. Schedule your private showing today and come see why this property might just be “the one” you didn’t know you were waiting for.

Listing is courtesy of: OPULENT REALTY INTERNATIONAL (863-323-7778)

Listing Agent: Alicia Self (863-450-8394)

Remarks: Super Motivated Seller!! Discover this charming 4 bedroom, 2 bathroom single family home located in the heart of Winter Haven, just minutes from the serene shores of Lake Howard. With its spacious layout and versatile design, this property is perfect for families and savvy investors alike. It has a separate mother in law suite, offering privacy or the potential for rental income. A recently renovated kitchen complete with modern finishes, making mal prep a delight. A huge backyard, ideal for family gatherings, gardening or creating your dream outdoor retreat. An expansive driveway and 2 car garage, with enough space to park multiple vehicles. A newer roof 2020 for added peace of mind and longevity. Well maintained interior and exterior ensuring move in readiness. prime locatioin near Lake Howard perfect for outdoor enthusiasts who enjoy fishing, boating and lakeside strolls. No HOA fees allowing you the freedom to enjoy your property without added restrictions or costs. Wether you are looking to grow your family or generate extra income, this home is a rare find. Don't miss the opportunity to own a property that combines comfort, style and versatility in a highly desirable area of Winter Haven. Ready to schedule a showing?

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

Listing Agent: Miluska Parot (352-573-3697)

Remarks: Short Sale. We are in the process of getting a short sale approved. So expect delays. Welcome to 29 Golfview Circle NE, a beautifully modernized Winter Haven property offering a rare combination of charm, flexibility, and income-producing potential. The main residence features 3 bedrooms and 2 baths with an open, inviting layout that includes spacious living and dining areas, stainless steel appliances, and a comfortable primary suite with a walk-in closet. Enjoy outdoor living from the covered front porch, the screened back patio, and the fully fenced yard. Additional updates— including a 2021 roof and numerous interior improvements—add peace of mind and long-term value. What truly sets this property apart is the detached 1BR/1BA guest house, completed in 2022 and designed as an ideal in-law suite or rental unit. This private space features polished concrete floors, a sleek updated kitchen, a modern bathroom with a large walk-in shower, an oversized closet with washer/dryer hookups, stainless steel appliances, its own fenced yard, and dedicated parking. Together, both structures offer approximately 2,228 sq. ft. of combined living space and 2,573 sq. ft. total under roof. Located on a corner lot directly across from Polk State College, this home delivers outstanding convenience with exceptional versatility—perfect for multigenerational living, additional income, or both. Opportunities like this are hard to find. Come see everything this remarkable property has to offer!

Listing is courtesy of: MARK SPAIN REAL ESTATE (855-299-7653)

Listing Agent: Chris Sakamoto (904-200-7535)

Remarks: Great investor or first time home buyer opportunity. This house has new windows, a new roof, updated electric panel and an renovated bathroom. The LVP throughout the home with 5-1/4 baseboard. This property has a huge back yard for your family to enjoy. Built in laundry with washer and dryer included. This property is move in ready and won't last long at this price. Schedule your showing today

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

Listing Agent: Stephen Hubbell (863-559-5666)

Remarks: This expansive two-story Columbus has a well-designed layout, featuring a first floor dedicated to shared living and entertaining. The open concept design seamlessly connects the kitchen, dining room and family room, with a patio extending the interior space outdoors. Upstairs, a spacious loft separates the three secondary bedrooms from the serene owner's suite. Completing the home is a convenient two-car garage. Villa Mar is a masterplan community of new single-family homes. Near Historic downtown Winter Haven. There are lots of shops, restaurants, bike paths, and easy access to nearby highways. Close to Legoland and Bok Tower Gardens. The much anticipated “Villar Mar” community is what you have been looking for. A safe small town feel with convenience.

Listing is courtesy of: LENNAR REALTY (800-229-0611)

Listing Agent: Ben Goldstein (407-310-7677)