Winter Haven Homes For Sale & Real Estate - 1035 homes

Remarks: Located on a spacious corner lot in the heart of Winter Haven, this income-producing duplex offers an unbeatable combination of location, and long-term potential. One unit is currently rented for $1,300 on a month to month lease. The other unit is currently vacant. Featuring a brand-new roof and easy access to Winter Haven’s famous Chain of Lakes, including Lake Howard and Lake Cannon. Residents can enjoy boating, fishing, and waterfront dining. Ideally situated only about 8 minutes from Downtown Winter Haven, residents can also enjoy local restaurants, shops, entertainment, and community events while still having quick access to major roadways for an easy commute throughout Polk County. The property also offers convenient access to nearby schools, including Inwood Elementary just 2 minutes away, Westwood Middle approximately 4 minutes away, and Winter Haven Senior High around 8 minutes away. Whether you’re looking to expand your investment portfolio or secure a property in one of Central Florida’s fastest-growing lakefront communities, This property has exceptional value with its prime location, recent improvements, and proximity to Winter Haven’s iconic lakes and downtown district.

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

Listing Agent: Corey Ayala (618-638-3273)

Remarks: Welcome to 8 St. Kitts Circle in Winter Haven—a move-in ready home that checks all the right boxes. Freshly painted and well-maintained, this property offers comfort and peace of mind with a metal roof (2023) and a newer A/C unit (2020). Even better, a brand-new water heater will be installed prior to closing, making this home truly ready for its next owner. Step outside to enjoy the vinyl-fenced rear yard—perfect for pets, play, or relaxing in your own private outdoor space. Enjoy the benefits of low-maintenance living with an incredibly affordable HOA fee of just $95 per year. Whether you're a first-time buyer, downsizing, or adding to your investment portfolio, this home offers a great combination of value, updates, and convenience. Don’t miss your chance to make it yours!

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

Listing Agent: Michelle Smith (863-412-7577)

Remarks: Short Sale. This property presents a great opportunity for buyers looking to renovate and add value. With a functional floor plan and generous living areas, it offers a solid starting point for updates and improvements. The layout provides flexibility to reimagine the space to suit your needs and design preferences. Spacious rooms allow for creative customization throughout. The kitchen area offers ample space to redesign and enhance. Bedrooms are well sized and provide potential to create comfortable retreats. There is opportunity to refresh both the interior and exterior to maximize appeal. Outdoor space allows room for landscaping or additional enhancements. Ideal for investors or buyers seeking a renovation project. Schedule your showing today and explore the possibilities.

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

Listing Agent: Cesar Estrada, Pa (321-209-4782)

Remarks: Under Construction. BELOW MARKET INTEREST RATES with use of Seller's Preferred Lender. Indigo - Check out the Indigo, a spacious two-story, 5-bedroom, 3-bathroom, 2-car garage home perfect for growing families or hosting guests. Enter the impressive foyer with soaring ceilings that creates an immediate sense of openness. From the foyer, the home effortlessly flows into the main living areas and kitchen. With quartz countertops throughout, stainless-steel appliances and a smart thermostat for energy efficient climate control, the Indigo brings all the things that matter together. The downstairs guest suite and bathroom are tucked away for added seclusion, while the open concept living space is perfect for entertaining. Upstairs, you'll find a generously sized recreation space, ideal for family time or unwinding. The owner's suite is a true sanctuary, featuring a walk-in shower, double vanities, and a spacious walk-in closet. A laundry room with a new washer and dryer is just off the owner’s suite, conveniently located near the 3 additional bedrooms and full bathroom. The Indigo is as functional as it is stylish, providing the perfect balance of comfort and modern living. Close to it all, Villa Mar places you near the natural beauty of the Winter Haven Chain of Lakes, the charm of downtown Winter Haven, and family fun at LEGOLAND® Florida Resort. Back at home, residents enjoy community amenities including a pool, dog park, playground, and walking trails. Images shown are for illustrative purposes only and may differ from actual home. Completion date subject to change. Contact or make an appointment for more details on interest rates.

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

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

Remarks: Under contract-accepting backup offers. •Motivated seller! Seller will contribute $10,000 at closing to be used at buyers' discretion for a permanent or temporary interest rate buy-down or closing fee. Move-In Ready 5 Bedroom Home with Resort-Style Amenities in Villamar This beautifully maintained 5 bedroom, 3 bathroom, 2,616 sq ft home is located in the desirable Villamar community. The home features both a living room and a family room that opens to the kitchen. The open-concept floor plan includes a spacious gathering room that flows into the dining area and a well-appointed kitchen complete with stainless steel appliances, shaker-style cabinets, a breakfast bar, and a walk-in pantry. The private owner’s suite offers a large walk-in closet, dual sinks, and a private water closet. Luxury vinyl plank flooring enhances the interior. A versatile downstairs bedroom and full bath provide flexible living options, ideal for a home office, guest suite, or multigenerational accommodations. Enjoy outdoor living on the covered lanai and large screened porch overlooking the preserve, along with beautifully maintained, Florida-friendly landscaping with irrigation. The community resort-style pool is perfect for relaxing in the Florida sun.

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

Listing Agent: Irene Bryan (863-289-6789)

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: Under contract-accepting backup offers. Welcome to 333 Lake Howard Dr NW, Unit 313A — a beautifully updated 2-bedroom, 2-bath condo located on the top (3rd) floor of a well-maintained 55+ community. The building offers elevator access and is wheelchair accessible, providing both comfort and convenience. This move-in ready unit features large windows in the living room overlooking the community pool, filling the space with natural light and offering peaceful views. Recent updates include all new kitchen cabinets and countertops, a new lanai cabinet, upgraded bathrooms, a new walk-in shower, new carpet throughout, fresh interior paint, new light fixtures, and new vent covers. The roof has also been replaced, adding additional value and peace of mind. Residents enjoy a variety of amenities including a community pool, fitness center, and direct lake access to Lake Howard. The private dock and boat parking make it easy to enjoy fishing, relaxing by the water, or docking your boat — all included in the HOA dues. Additional features include assigned covered carport parking and a 4x4x4 extra storage space located on the 2nd floor. Enjoy low-maintenance living with resort-style amenities in a prime location.

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

Listing Agent: Brian Cox (863-559-3627)

Remarks: One or more photo(s) has been virtually staged. Motivated Seller!! *Welcome to this spacious Move-in-ready 4 bedroom, 2.5 bathroom home tucked away in the heart of Royal Hills, Winter Haven. The Home has recent upgrades including freshly painted Exterior in 2025, Roof 2024. The entire upper level has been revitalized with well-maintained carpeting while the ground floor showcases ceramic tile throughout. The kitchen contains Sleek granite countertops for that touch of sophistication,Stainless-steel appliances along with bright light fixtures.The home also has a BONUS Room on the ground level - perfect for a Home office or Media Room and a HUGE Fenced backyard. Conveniently situated near US-27, this property offers quick access to interstate travel and shopping centers. Don't let the opportunity slip by to make this beautiful house your next family home

Listing is courtesy of: MILLENNIUM REALTY CENTER LLC (407-843-8996)

Listing Agent: Phabie Terzier (407-692-7452)

Remarks: Turnkey Villa in Stonebridge — Low Maintenance Living, Prime Location Step into easy Florida living with this move-in ready 2-bedroom, 2-bath villa in the highly desirable Stonebridge community. With vaulted ceilings, abundant natural light, and an open-concept layout, the home feels bright, spacious, and immediately inviting. The thoughtfully designed split-bedroom floor plan offers ideal privacy for guests, roommates, or a dedicated home office. The primary suite provides a relaxing retreat with a walk-in closet and a spacious walk-in shower. The kitchen is both functional and welcoming, featuring generous counter space, ample cabinetry, and a breakfast bar that flows seamlessly into the main living area—perfect for everyday living or casual entertaining. Major systems—including the roof, HVAC, and water heater—are all approximately 3 years old, giving buyers peace of mind from day one. Step outside and enjoy one of the home’s standout features: direct proximity to the community pool—just steps away for effortless relaxation. Conveniently located near downtown Winter Haven, Legoland, Disney, and major roadways with access to Florida’s beaches, this home is ideal for full-time living, a seasonal retreat, or an investment opportunity. Opportunities like this don’t last—schedule your private showing today.

Listing is courtesy of: VIVA ORLANDO REALTY INC. (407-861-0000)

Listing Agent: Larry King (404-441-5050)

Remarks: Owner motivated and ready to negotiate — WOW! This BEAUTIFUL 931 SF 1BR/1BA FIRST-FLOOR condo in Orchid Springs offers stunning lagoon views! Located in the 55+ Granada Building, where at least one occupant must be 55+. IMMEDIATELY AVAILABLE and MOVE-IN READY! Step into an open, airy floor plan with tile throughout, creating a bright and spacious feel. The dining area, living room, and bonus room flow seamlessly together, all overlooking the tranquil lagoon. As an end unit, the living room and bedroom enjoy extra windows with peaceful courtyard views. The bedroom features a walk-in closet plus an additional hallway closet, providing excellent storage. The bathroom includes a custom vanity and a tub/shower combo. A washer and dryer are included, offering added convenience. Additional highlights include assigned parking directly in front of the unit. Perfect for year-round living or a seasonal retreat in a serene, well-maintained community.

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

Listing Agent: Sharon Gastelbondo (863-800-4655)

Remarks: Owner motivated and ready to negotiate — WOW! This BEAUTIFUL 1361SF 2BR/2BA FIRST-FLOOR condo in Orchid Springs offers stunning lagoon/pond views! Located in the 55+ Granada Building, where at least one occupant must be 55+. IMMEDIATELY AVAILABLE and MOVE-IN READY! Step into an open, airy floor plan with tile throughout, creating a bright and spacious feel. The dining area, living room, and bonus room flow seamlessly together, all overlooking the tranquil lagoon. As an end unit, the living room and bedrooms enjoy extra windows with peaceful courtyard views. The primary bedroom features a walk-in closet plus an additional hallway closet, providing excellent storage. Both bathrooms are well-appointed, with one offering a custom vanity and a tub/shower combo. Additional highlights include assigned parking directly in front of the unit. Perfect for year-round living or a seasonal retreat in a serene, well-maintained community.

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

Listing Agent: Sharon Gastelbondo (863-800-4655)

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: 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: 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: 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)

Remarks: Back on Market one more chance for you.This stunning 5-bedroom, 3-bathroom home offers the perfect blend of modern comfort, energy efficiency, and scenic beauty. Located in the desirable VillaMar community, this spacious home features an open-concept layout ideal for family living and entertaining. Enjoy peaceful mornings with breathtaking pond views right in your backyard — your private retreat for relaxation and tranquility. The home also includes solar panels, helping you save on energy bills while living sustainably. With elegant finishes, a large kitchen, and plenty of natural light throughout, this home is move-in ready and waiting for its new owners. Features resort-style community amenities including a zero-entry swimming pool with a lap lane, a playground, a dog park and sidewalks.Conveniently located near shopping, restaurants, and top-rated schools — this is the lifestyle you’ve been looking for in Winter Haven!

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

Listing Agent: Karina Turcios (407-346-7606)

Remarks: Under contract-accepting backup offers. PRICE ADJUSTMENT....Located within a desirable gated community, this beautifully maintained home at 455 Majestic Gardens Blvd offers both comfort and functionality. Featuring a 1-year-old roof and an open floor plan, the home is designed for effortless everyday living and entertaining. The kitchen is appointed with granite countertops and flows seamlessly into a spacious family room. Tile and laminate flooring run throughout the home, adding durability and style. A bonus room provides flexible space ideal for a home office or additional sitting area. Step outside to your private backyard oasis with a fully fenced yard, inground swimming pool with spa, and a paver deck—perfect for relaxing or hosting gatherings. This home combines modern updates, versatile living spaces, and resort-style outdoor living in a secure, gated setting. This home boasts a 30 panel solar system that generates 16,447 kwz per year. The pool is heated by a separate propane system.

Listing is courtesy of: CRAIG BURKE REAL ESTATE GROUP, LLC (863-899-5010)

Listing Agent: Craig Burke (863-899-5010)