Winter Haven Homes For Sale & Real Estate - 1004 homes

Remarks: This home is a must see!! Very well maintained home located in Village Park, a 55+ community where dogs are allowed. The home features new thermal efficient windows and all new plumbing. The vapor barrier is also new. The kitchen is very open and functional. The living room is comfortable and inviting. The primary bath has a new vanity and the bedroom carpet is new. Plus, the laundry is located inside a closet in the hall bath. The vaulted ceilings give the feel of spaciousness. Outside you will find a double shed which opens to the the front and back. Sit on the front porch and enjoy your morning coffee or evening cocktail. The community features a clubhouse, pool, and shuffleboard. There are many activities available, or you can just sit back and enjoy the peaceful community. This home is a must see!

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

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

Remarks: NO LOT RENT. Welcome to your slice of Florida living in Winter Haven! This well-maintained 2-bedroom, 2-bath home offers 1,620 sq ft of comfortable living space and is packed with valuable upgrades, including the ROOF 2023 and 4 ton A/C 2023, Water Heater 2024 or 2025, water softener, reverse osmosis system, and rain gutters with leaf guards for added peace of mind. Step inside to find a spacious floor plan. Relax and unwind in the large screened-in lanai, ideal for enjoying Florida’s beautiful weather year-round. The property also features a large storage shed with air conditioning, giving you plenty of room for tools, hobbies, or seasonal items and an inside laundry with washer and dryer included. Located in the desirable Village Park community for those 55+ years young, residents enjoy an incredibly low HOA fee of just $55 a month, which includes access to a sparkling pool and community amenities. Best of all—you own the land! Limited trailer/RV storage is also available on a first-come basis. Perfectly situated between Tampa and Orlando, this home offers convenient access to world-renowned attractions like LEGOLAND Florida Resort, Walt Disney World, Universal Studios Florida, Busch Gardens Tampa Bay, ZooTampa at Lowry Park, and Seminole Hard Rock Hotel & Casino Tampa. You’re also just minutes from shopping, dining, grocery stores, hospitals, golf courses, nature parks, and Florida’s beautiful beaches. With both Tampa and Orlando international airports within about an hour’s drive, travel is incredibly convenient. Whether you're looking for a full-time residence or a seasonal retreat, this home checks all the boxes. Don’t miss your opportunity to live in Village Park—schedule your private showing today!

Listing is courtesy of: DALTON WADE INC (888-668-8283)

Listing Agent: Carolyn Christian, Llc (863-514-6378)

Remarks: Charming and well maintained! 2-Bedroom 2- Bath Home in Desirable 55+ Community – You Own the Land with low HOA fees! This inviting home features fresh interior and exterior paint and a newly screened-in front porch, perfect for enjoying your morning coffee, afternoon tea or just relaxing in the Florida breeze. The property also offers a fenced-in backyard, ideal for pets to play or gardening. Additional highlights include a one-car carport and a spacious 22x11 workshop/storage area, providing plenty of room for hobbies, tools, or extra storage. Residents enjoy access to a community clubhouse and sparkling pool, perfect for socializing and staying active in this welcoming neighborhood. Conveniently located near shopping, dining, and local amenities, this home offers both comfort and convenience. Don’t miss this opportunity to own an affordable home with land ownership in a vibrant 55+ community!

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

Listing Agent: Michelle Armbruster (863-521-6879)

Remarks: Cypresswood Golf & Country Club welcomes you to 419 Greenfield Drive. This desirable gated golf community has a host of activities and treasures, but by far the most impressive one is this gem and it shows. As you pull up to the extended driveway, low maintenance landscape ushers you into a well appointed home. Once in the front door, sparkling floor tiles guide you through this beautiful 3 bedroom 2 bath split floor plan home. Quartz counters and wall to wall cabinet space give anyone that loves to cook the space they need to store items and create meals while hosting family or company. Right off of the kitchen there is a climate controlled Florida room, with an additional screened-in patio to the rear. When you are ready to retire for the evening, your primary bedroom has plenty of space to stretch out in and keep your belongings in the large walk-in closet. Move right in and leave your worries behind. Not only has the kitchen and flooring been recently upgraded, all your major components have been replaced within the last 5 years - brand new electric panel w/surge protection installed (May 2026), roof (2022) , water heater (2021), A/C (2021). Schedule your private tour and make this home yours for years to come.

Listing is courtesy of: BOARDWALK REALTY ASSOCIATES, LLC (800-567-0535)

Listing Agent: Ralph Eugene (813-263-8432)

Remarks: Be the first to own this stunning 2024-built semi-custom home located in the gated, lakefront community of Woodpointe in Winter Haven’s desirable 33884 zip code. Thoughtfully designed with both comfort and functionality in mind, this spacious residence features 4 bedrooms, 3.5 bathrooms, and an incredibly smart split-bedroom floorplan that offers privacy and flexibility for modern living. The seamless flow and attention to detail throughout brings you first to the expansive living area that encompasses the living, kitchen, and dining rooms complimented with a walk-in pantry and bonus room that's perfect for an office, playroom, gym, or anything your hobbies and interests desire. The primary suite is a true retreat, complete with a luxurious en-suite bath and a huge walk-in closet that conveniently connects directly to the oversized laundry room—making everyday living effortless and latenight chores not disturbing family and guests. On the opposite side of the home, the additional bedrooms are well-appointed and thoughtfully positioned to maximize space and privacy, including another bedroom with ensuite bath, plus two additional bedrooms and another full bathroom. A convenient half bath is located near the garage entry, where you'll also find a practical "mud" area perfect for keeping things organized after a long day. Situated on just over one-third of an acre, the property offers ample outdoor space with room to create your ideal backyard oasis. As part of the exclusive Woodpointe community, residents enjoy the peace of a gated neighborhood along with access to beautiful lakefront surroundings. This home blends modern convenience, smart design, and a prime location—making it an exceptional opportunity in one of Winter Haven’s most sought-after areas. The Woodpointe community is minutes from Highway 27 and the I-4 corridor, Winter Haven's very own Legoland Florida Resort, the Polk Parkway, and in the center of a thriving community with many convenient grocery, restaurant, shopping, and commuting options for travel in less than an hour from Disney World and other Orlando attractions, the Orlando and Tampa International Airports, and the gulf-side beaches of Tampa/St. Pete. See this home in person to really appreciate ALL that it has to offer!

Listing is courtesy of: JOHN WOOD REALTY, INC. (863-324-9663)

Listing Agent: Kayly Malinas, Pa (863-258-1426)

Remarks: Discover affordable luxury and modern Florida living in this beautifully designed brand-new 2025 home located in the growing Peach Crossings community of Winter Haven. Perfectly positioned for first-time homebuyers, growing families, remote professionals, and buyers seeking more space without sacrificing style, this move-in ready 4-bedroom, 2-bath residence offers the ideal combination of comfort, functionality, and value in one of Polk County’s rapidly expanding areas. Built by LGI Homes, the highly sought-after “Summit” floor plan features an open-concept design with soaring ceilings, abundant natural light, and thoughtfully designed living spaces perfect for entertaining and everyday living. The spacious chef-inspired kitchen is equipped with granite countertops, solid wood cabinetry, Whirlpool stainless steel appliances, generous prep space, and seamless flow into the dining and family room area creating the perfect setting for gatherings, holidays, and movie nights at home. The oversized primary suite offers a peaceful retreat with a large walk-in closet and spa-style en-suite bathroom featuring dual vanities, stone countertops, and a step-in shower. Three additional bedrooms provide flexibility for guest rooms, a home office, fitness room, or playroom. Luxury vinyl flooring throughout the main living areas, energy-efficient windows, smart layout design, interior laundry room, and modern finishes add both style and practicality for today’s buyers. Step outside and enjoy covered outdoor living space ideal for relaxing evenings, weekend cookouts, or enjoying Florida’s year-round sunshine. Professionally designed landscaping, irrigation, sidewalks, and attractive curb appeal make this home stand out from the moment you arrive. Located near shopping, dining, medical facilities, parks, and major commuter routes, Peach Crossings offers convenient access to Lakeland, Orlando, and Central Florida attractions while still maintaining a quieter residential atmosphere. Community amenities include playgrounds, parks, picnic areas, and access to highly desired Polk County schools, making this neighborhood especially appealing to families and buyers relocating to Florida. With no CDD fees, low HOA costs, builder warranty coverage, and financing options including FHA, VA, USDA, and Conventional loans, this property presents an exceptional opportunity for buyers looking for affordable new construction in Winter Haven with long-term value and lifestyle appeal.

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

Listing Agent: Renee Anthony (407-603-5935)

Remarks: Welcome to 511 Heather Glen Drive. This beautifully maintained home is in move in ready condition. Offering 4 bedrooms and 2 bathrooms, the home has new interior and exterior paint. This is a split floor plan with a large family room looking out to the screened in patio. Off the kitchen is a dinette. The guest bathroom has been remodeled. Both bathrooms have new toilets. New carpeting in bedrooms 2 and 3. The A/C is brand new with a HALO system that purifies the air in the house. The roof is 9 years old. Brand new hot water heater. There is an inside laundry room leading out to the garage. Riding lawnmower is included! The home is centrally located close to Legoland, dining, shopping and major highways and in between Orlando and Tampa. This home shows pride of ownership! Make your appointment today!

Listing is courtesy of: THE HOME COMPANY (863-268-8157)

Listing Agent: Sue Ann Williamon (863-258-3115)

Remarks: Immaculate 4-Bedroom, 3-Bathroom Plus Office Home in the Coveted Crossroads at Lake Region Welcome to this beautifully maintained residence located in the highly desirable gated community of Crossroads at Lake Region. This spacious four-bedroom, three-bathroom home with a dedicated office offers the perfect blend of comfort and functionality. As you arrive, you’re welcomed by a handsome paver driveway that adds both charm and curb appeal. Step inside to soaring vaulted ceilings and an open-concept floor plan, ideal for both everyday living and entertaining. Expansive living and dining areas flow effortlessly, creating a bright, airy feel throughout the home. The oversized primary suite, located just off the main living area, is a true retreat. It features a luxurious en suite bathroom complete with a large soaking tub, separate walk-in shower, dual sinks, and a spacious walk-in closet. Fresh interior paint gives the home a crisp, updated look, and a new roof provides added peace of mind. A private office offers the perfect space to work from home or can easily flex to fit your lifestyle. This home is situated just a short distance away from the community pool and hot tub. This one checks all the boxes!

Listing is courtesy of: CENTURY 21 MYERS REALTY (863-875-5656)

Listing Agent: Jill Lingenfelter (863-242-0900)

Remarks: Under contract-accepting backup offers. Welcome to 8 The Village Blvd—nestled in a highly desirable gated community in Winter Haven with exclusive access to beautiful Spirit Lake! This well-maintained former model home offers 3 bedrooms, 2 baths, and a 2-car garage, combining comfort, style, and thoughtful upgrades throughout. Step inside to an inviting open floorplan featuring gleaming wood floors, a formal dining area overlooking the spacious front yard, and a stunning magnolia tree that enhances the home’s curb appeal. The kitchen is designed to impress with Corian countertops, upgraded appliances, and abundant cabinet and counter space, flowing seamlessly into a bright breakfast nook with views of the backyard and large screened lanai. The split-bedroom layout provides privacy, with two generously sized guest bedrooms and a full bath (with lanai access) tucked away on one side of the home. The spacious primary suite is located on the opposite side and features sliding glass doors to the lanai, dual walk-in closets, and a luxurious en-suite bath complete with a garden tub, separate shower, and ample counter space. Major updates offer peace of mind, including a new roof (May 2023), upgraded 50-gallon water heater (2021), new garage door opener (2022), upgraded main electrical panel (2024), and a Brinks Home Security System and Goodman AC (2025) with transferable warranty. The 2-car garage includes a Chamberlain opener (2022), built-in shelving, and a pegboard—perfect for organization. Enjoy all the amenities this sought-after gated community has to offer, including a clubhouse, recently refinished pool, tennis and basketball courts, updated exterior lighting, and a freshly painted entrance and clubhouse. Residents also enjoy private access to Spirit Lake via a boat ramp and dock. This move-in-ready home is truly “neat as a pin” and ready for its next owner. Survey and floorplan available—schedule your private showing today!

Listing is courtesy of: HOUWZER INC (267-765-2080)

Listing Agent: Daniel Robinson (904-447-8922)

Remarks: This property NOW INCLUDES 20 STORAGE UNITS and nearly 3 acres of land, creating a truly rare lakefront development opportunity within the Winter Haven Downtown CRA District. Enjoy beautiful views of Lake May with direct access to the Winter Haven Chain of Lakes — a prime location for growth and investment. Current DOR use code (0852) permits duplexes, triplexes, and quadplexes — up to 9 units — throughout the Polk City, Auburndale, Lake Alfred, and Winter Haven areas. The property also features a 1,208 sq. ft. concrete block structure built in 1955, offering additional utility or potential for redevelopment. The value lies in the land, location, and flexibility of use. Possible future options include multi-family housing, office/professional, or light industrial projects (subject to approvals). Conveniently close to downtown Winter Haven’s shopping, dining, parks, and major roadways, this site is positioned perfectly for future growth. A rare opportunity to invest, develop, or hold in one of Central Florida’s fastest-growing markets.

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

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

Remarks: New Price and $2500 Seller Credit!! Relocating to Florida? This pristine 5-bedroom, 3-bath home offers nearly 2,700 square feet of thoughtfully designed living space in the heart of Central Florida, providing the space, flexibility, and value many buyers from northern states and high-cost markets are seeking. Priced at $374,900—approximately $140 per square foot—this home delivers exceptional value compared to similar properties in California and many northern metro areas. The well-planned layout includes five true bedrooms, three full bathrooms, and a versatile flex space that could easily be converted into a sixth bedroom. This additional space makes the home ideal for growing families, multigenerational living, aging parents, young adults living at home, or a private home office or hobby room. A guest suite on the first floor adds even more functionality and convenience. The main living areas feature upgraded tile flooring, while the kitchen is finished with granite countertops and ample workspace for everyday living and entertaining. The home has been meticulously maintained and is in pristine, move-in-ready condition. Outdoors, enjoy added privacy with no rear neighbors, creating a peaceful and open backdrop rarely found in newer communities. Located just 5 minutes from downtown Winter Haven, residents enjoy easy access to historic charm, the Ritz Theatre, Saturday farmers markets, a beautiful public library, and a growing selection of high-end and locally owned dining options. A brand-new Publix grocery store is currently under construction within walking distance, adding everyday convenience and long-term appeal. The community features a very low HOA and no CDD fees, helping keep ownership costs manageable—an important advantage for relocating buyers. Ideally positioned just 5 minutes from Legoland Florida and approximately 30 minutes from Disney, the home offers access to Central Florida attractions while maintaining a comfortable residential setting. With generous square footage, flexible living spaces, privacy, and proximity to downtown amenities, this home is an outstanding opportunity for buyers ready to trade cold winters or high housing costs for a more flexible and comfortable Florida lifestyle.

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

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

Remarks: One or more photo(s) has been virtually staged. Step into this renovated farmhouse charm : 2-bedroom, 2-bathroom home, nestled on a spacious lot in the established Villa Manor neighborhood. NO HOA This move-in-ready residence presents luxury finishes, laminate flooring throughout, a sleek new kitchen with updated cabinets, carrara white quarts countertops, and stainless steel appliances, and a freshly tiled bathroom with contemporary finishes. Fresh interior and exterior paint, and upgraded lighting fixtures. Roof 2020 - - Repipe 2025 - The large backyard offers plenty of space for outdoor living or future expansion. Located minutes from local schools, parks, and downtown Winter Haven’s shops and restaurants, this home is perfect for first-time buyers, downsizers, or investors seeking turnkey potential.

Listing is courtesy of: KELLER WILLIAMS LEGACY REALTY (407-855-2222)

Listing Agent: Daniel Araque (321-276-0747)

Remarks: Welcome to 255 Haines Boulevard, Winter Haven, Florida! This beautifully maintained home offers the perfect blend of comfort, convenience, and Florida living. Featuring a spacious floor plan with plenty of natural light, this property is ideal for families, first-time homebuyers, or investors alike. The kitchen provides ample cabinet and counter space and flows seamlessly into the living and dining areas, making it perfect for entertaining guests. Step outside and enjoy the generous yard with room for outdoor activities, gardening, or future enhancements. Conveniently located near shopping, dining, schools, medical facilities, and major roadways, this home provides easy access to everything in Winter Haven. Whether you're looking for a primary residence, seasonal home, or investment property, this move-in-ready opportunity is one you won't want to miss. Schedule your private showing today!

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

Listing Agent: Sean Denney (863-602-0424)

Remarks: One or more photo(s) has been virtually staged. Welcome to maintenance-free Florida living in the peaceful 55+ community of Imperial Harbours. This 3rd floor 2-bedroom, 2-full-bath condo offers the relaxed lifestyle many buyers look for, complete with elevator access for easy entry. You are greeted by views of the community pool and cabana area right from your front entrance, while the interior features a bright Florida Room and a relaxed lakeside atmosphere. Best of all, the monthly HOA fee covers everything except your electric bill, making your budget completely stress-free. Enjoy premier amenities like a private boat ramp and fishing pier right on Winter Haven's popular Chain of Lakes. Located just across the water from downtown shopping and dining, this well-established, owner-occupied neighborhood is ready to welcome you home to a truly wonderful community lifestyle!

Listing is courtesy of: REGAL REAL ESTATE LLC (863-660-7927)

Listing Agent: Natalie Elson (863-709-3516)

Remarks: Welcome to 1217 Michelangelo Ln., a beautifully updated Wakefield model by Centex Homes located in one of Winter Haven’s most desirable communities — with NO CDD fees and convenient access to shopping, dining, medical facilities, and local attractions! Situated on a premium corner lot, this spacious 4-bedroom, 3.5-bath home offers the perfect blend of style, functionality, and modern updates throughout. From the moment you walk in, you’ll notice the designer touches including updated lighting, modern fixtures, sleek ceramic tile flooring, and tasteful upgrades in every room. The open-concept kitchen features granite countertops, stainless steel appliances, updated faucets and fixtures, beautiful pendant lighting, and abundant cabinet space — perfect for entertaining and everyday living. The spacious primary suite is conveniently located on the main level and includes dual sinks, a relaxing garden tub, separate shower, and an oversized walk-in closet. Also downstairs is a stunning French door office that can easily function as a 5th bedroom, guest room, or flex space if desired. Upstairs, enjoy a large bonus room ideal for a media room, playroom, fitness area, or second living space. The beautifully designed laundry room adds both style and convenience. Step outside to your oversized fenced backyard featuring a white vinyl fence, offering privacy and plenty of room for pets, gatherings, or future outdoor living additions. Additional upgrades include a new water softener system for added comfort and value. Located just minutes from Winter Haven Hospital and close to everything Winter Haven has to offer, this move-in ready home truly checks all the boxes. Don’t miss your opportunity to own this exceptional property!

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

Listing Agent: Susan Brown (863-640-5722)

Remarks: One or more photo(s) has been virtually staged. Short Sale. Back on the market with renewed opportunity! Enjoy peaceful lakefront living in this beautiful updated 2 bedroom, 2 bath condo located in the gated Winterset community. Featuring an open floor plan granite countertops, stainless steel appliances, upgraded cabinetry, and a cozy breakfast nook, this home offers both comfort and style. The enclosed balcony showcases stunning views of Garden Lake, perfect for quiet mornings or relaxing evenings. Recent updates include plumbing, electrical, lighting, bathroom vanities, and updated flooring throughout, making this home truly move-in ready. Winterset offers resort - style amenities including pool, spa, clubhouse, tennis and pickleball courts, and a private lakefront pier. Conveniently located just minutes from LEGOLAND and under an hour to Orlando attractions. Short sale- priced in alignment with lender expectations. A great opportunity for buyers looking for value, a primary residence, or an investment property.

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

Listing Agent: Valerie Howze (863-604-9080)

Remarks: Under contract-accepting backup offers. Fully remodeled two story 4 bedrooms 3 bathrooms home featuring a modern neutral color palette, white cabinets, vinyl plank flooring throughout, and brand new stainless steel appliances. Bright and updated interior with a clean contemporary feel. Move-in ready and designed for low-maintenance living.

Listing is courtesy of: NUMBER ONE CHOICE REALTY CORP (352-404-5638)

Listing Agent: Daulis Webb Gagnon (407-234-9789)

Remarks: Experience elevated living in this beautifully maintained 3 bedroom, 2 bathroom residence located in the highly desirable Country Walk community in Winter Haven. Designed with style and comfort in mind, this home showcases custom luxury finishes throughout the living room and bedrooms, creating an elegant and inviting atmosphere. The open concept layout offers the perfect blend of functionality and sophistication, while the modern kitchen serves as the centerpiece of the home with sleek cabinetry, quartz countertops, and ample space for cooking and entertaining. The spacious primary suite provides a private retreat with a walk in closet and a beautifully appointed bathroom. Step outside and enjoy the extended paver patio, an ideal space for relaxing or hosting family and friends, all enclosed by a white PVC privacy fence that enhances both comfort and privacy. Conveniently located near shopping, dining, schools, medical facilities, and major highways, this home is also just minutes from LEGOLAND Florida Resort and many of Central Florida’s most popular attractions. Combining stylish interior design, exceptional outdoor living, and a prime location, this residence offers an outstanding opportunity to enjoy the best of the Florida lifestyle.

Listing is courtesy of: KELLER WILLIAMS LEGACY REALTY (407-855-2222)

Listing Agent: Maria Santacruz (407-552-8213)

Remarks: Welcome to resort-style living in the highly sought-after Lake Ashton Golf Club Community! This impeccably maintained home is nestled on a quiet and secluded street, offering the perfect combination of privacy, comfort, and an active Florida lifestyle. From the moment you arrive, you will appreciate the pride of ownership and pristine condition of this beautiful residence. Designed for both everyday living and entertaining, the home offers spacious living areas, abundant natural light, and a floor plan that flows effortlessly throughout. One of the most valuable features of this property is that the CDD bond has been fully paid off, providing significant long-term savings and added value for the new owner. Lake Ashton is one of Central Florida's premier gated 55+ communities, offering an unmatched array of amenities and activities. Residents enjoy access to two private 18-hole championship golf courses, including one of the most challenging and highly regarded courses in the region, making it a favorite among golf enthusiasts. The community also features two expansive clubhouses, a state-of-the-art health and fitness center, resort-style pools, tennis and pickleball courts, bowling lanes, movie theater, ballroom, restaurant and lounge, arts and crafts facilities, numerous social clubs, and a private marina with access to beautiful Lake Ashton. Whether you are looking for an active retirement, a seasonal retreat, or your forever home, this exceptional property offers the perfect opportunity to enjoy the Florida lifestyle at its finest. Schedule your private showing today and discover why so many residents proudly call Lake Ashton home.

Listing is courtesy of: COLDWELL BANKER RESIDENTIAL RE (305-361-5722)

Listing Agent: Emily Bastos Porto (407-969-9830)

Remarks: One or more photo(s) has been virtually staged. 2-Bedroom, 2-Bathroom Mobile Home in a 55+ Community of ORANGE MANOR WEST-NO LOT RENT!-This spacious 1,352 sq. ft. double wide mobile home located in a 55+ community that offers a wealth of amenities for an active lifestyle. BRAND NEW A/C! The living room features sliding glass doors that open to a front enclosed Florida room, perfect for enjoying the view of your front yard. The kitchen comes fully equipped with all appliances and a separate dining room for your meals. The main bedroom boasts an en-suite bathroom and a walk-in closet. The second bedroom is adjacent to a recently updated bathroom. Inside laundry room with additional storage, washer, and dryer included. A long carport that can accommodate two cars, with a garage door leading to extra storage space. Roof: Installed in 2017. Community Amenities: Pool, Clubhouse with billiards and library,Putt-putt golf, Bocce ball and horseshoe fields, Shuffleboard and Basketball court. Please note, this park does not allow pets. Don’t miss out on this wonderful opportunity! Call now for more details.

Listing is courtesy of: COLDWELL BANKER REALTY (863-687-2233)

Listing Agent: Kelley Blackburn (813-478-0023)