Homes For Sale in Winter Haven 33884 - 432 homes

Remarks: Enjoy the Florida Country Club Lifestyle in this affordable and updated 2 bedroom 2 bath villa. Recent updates include new luxury vinyl flooring, new dishwasher and new microwave. MOVE IN CONDITION. The country club amenities include access to the clubhouse with bar and grill, jr. Olympic swimming pool and pickleball/tennis courts. The championship 18 hole golf course is open to the public. As an added bonus, Publix just opened a brand new location just a mile down the road which is sure to attract other popular businesses.

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

Listing Agent: Steven Smith, Pa (863-224-2297)

Remarks: Under contract-accepting backup offers. Better than new! Completely Remodeled! This 3 bedroom 2 bath home has been completely remodeled, to include a new a/c, new water heater, a beautiful new kitchen, new flooring, new lights & fixtures, and new paint, and the roof was replaced in 2023.

Listing is courtesy of: ALLSTATE REALTY SERVICES (863-965-0207)

Listing Agent: Dwight Head (863-965-0207)

Remarks: Relaxed golf community living inside the gated and guarded Cypresswood Golf & Country Club. Welcome to 460 Pinehurst Ct in Winter Haven, Florida — an updated and spacious 2 bedroom, 2 bath patio home tucked away on a quiet cul-de-sac street with no through traffic. A private walled walkway leads to a charming front porch with sitting area, creating a warm and welcoming approach. Step inside the foyer to discover a clean, updated interior offering more than 1,600 square feet of comfortable living space, highlighted by beautiful new flooring, a freshly painted interior, and a long list of thoughtful improvements. All carpeting has been removed, the outdated popcorn ceilings have been scraped and refinished for a more modern look, and the overgrown landscaping has been cleared away to create a clean, attractive, and easy-to-maintain property. The roof was replaced in 2020 for added peace of mind, and gutters have also been installed for convenience and functionality. The great room design creates a spacious and open feel, accentuated by built-in shelving and large glass sliders that bring in natural light while offering the perfect space to showcase personal décor and seasonal accents. Sliding glass doors open to the enclosed, air-conditioned Florida room, seamlessly expanding the living area and creating an easy indoor-outdoor lifestyle that can be enjoyed year-round. The great room also offers space for formal dining in addition to the casual eat-in area found within the kitchen. The generously sized kitchen features abundant real wood cabinetry, a large breakfast bar, closet pantry, and an inviting dining area ideal for casual meals and everyday living. The primary suite offers comfortable dimensions, a walk-in closet, and an en-suite bath complete with a tiled walk-in shower. The guest bedroom is also nicely sized and features its own walk-in closet along with convenient access to the full guest bathroom with tub and shower. Storage is abundant throughout the home with multiple interior closets, garage storage closets, and a spacious 2-car garage with laundry connections, helping keep everything neatly organized and out of sight. Additional features include an irrigation system and low-maintenance exterior living. Beyond the home, Cypresswood delivers one of Winter Haven’s most enjoyable golf community lifestyles. Residents enjoy access to the 18-hole championship golf course, originally opened in 1969 and designed by award-winning architect Ron Garl. Known for its rolling fairways and mature landscaping, the course also features a pro shop, driving range, putting green, and dedicated short-game practice areas. Just a short stroll from the home, residents can enjoy the recently refurbished junior Olympic-sized swimming pool, tennis courts, pickleball courts, and Wellness Center. The Cypresswood Pub & Restaurant serves as the social heart of the community, offering planned events, a full bar, great food, and live weekend music in a relaxed setting overlooking the golf course. Whether you are searching for a full-time residence, winter retreat, or low-maintenance golf community home, 460 Pinehurst Ct offers an exceptional opportunity to enjoy the Florida lifestyle in one of Winter Haven’s most established gated golf communities.

Listing is courtesy of: THE STONES REAL ESTATE FIRM (863-412-2080)

Listing Agent: Michael Stone (863-412-9733)

Remarks: Like-new 2022-built home on a desirable corner lot in the heart of 33884, located in a community loaded with amenities! This beautifully maintained 3-bedroom, 2-bath home offers modern living with an open, functional layout and split floorplan. A standout feature is the upgraded enclosed patio/all-seasons room, complete with windows and screens—perfect for relaxing year-round, entertaining guests, or enjoying Florida living without the bugs. The home shows like new and offers peace of mind with newer construction, while the community amenities add incredible value and lifestyle appeal. Conveniently located near shopping, dining, and everything Winter Haven has to offer. Move-in ready and priced to sell—don’t miss this one!

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

Listing Agent: Katherine Montana - De Jesus (863-508-3000)

Remarks: Under Construction. This BEATIFUL ROBIE Model home has 5 bedrooms, 3 baths & a 2-car garage-2447 SqFt. NEWLY UPGRADED! Large 2-STORY open floor plan with Living & Dining room & Kitchen to entertain & enjoy the company of your guests. One bedroom located in the first floor, W/FULL BATH. Your very spacious master suite located on the 2nd floor with a large walk-closet & a double sink vanity with stall shower. This Home provides Stainless Appliances which include range, hood microwave, refrigerator, dishwasher and much more. We also provide Smart Home Technology which allows you to set the scene and connect to your home with your voice, from your smart phone, or through the smart panel interface. Your Smart Home comes with Alarm app, Echo Dot, Kwikset Smart Front Lock, IQ Panel, SkyBell, Z-Wave Thermostat, and a Z-Wave Light Switch. *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: Welcome to this beautifully maintained 2 Bedroom 2 Bath home offering the perfect blend of comfort, style, and functionality. From the moment you arrive, you’ll appreciate the inviting curb appeal and thoughtfully designed layout. Inside, you’ll find spacious living areas filled with natural light & generously sized bedrooms designed for everyday living and entertaining alike. Step outside and discover one of this home’s standout features — a fully equipped man cave/workshop in the backyard complete with its own powerful 5-ton A/C unit, making it the perfect space for entertaining, hobbies, a game room, home gym, or additional workspace year-round. Or a possible income opportunity! Conveniently located near shopping, dining, schools, and major roadways, this home combines peaceful living with everyday convenience. Whether you’re a first-time buyer, growing family, or looking for your next investment opportunity, this property is one you won’t want to miss. Schedule your private showing today!

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

Listing Agent: Candice Knoll (863-608-5114)

Remarks: Located in one of SE Winter Haven's most desirable gated communities, this meticulously maintained 4-bedroom, 3-bath pool home offers the perfect blend of elegance, comfort, and Florida outdoor living. Showcasing a desirable triple-split floor plan and numerous updates, including a new roof in 2022 and a new water heater in 2026, this move-in-ready residence is designed to accommodate both everyday living and entertaining with ease. Stepping through the front door, you'll immediately appreciate the soaring ceilings, elegant crown molding, and luxury vinyl flooring that flows seamlessly throughout the entire home. The thoughtfully designed layout offers both formal and casual living spaces, providing a warm and inviting atmosphere. The formal living room features stacking sliding glass doors that open to the lanai and pool, creating seamless indoor-outdoor living, while the adjacent formal dining room provides an elegant setting for gatherings and special occasions. At the heart of the home, the spacious kitchen has been beautifully updated with professionally painted maple wood cabinetry, granite countertops, stainless appliances, a breakfast bar, and a double-door closet pantry offering exceptional storage. The adjoining family room creates a comfortable space to relax and enjoy time with family and friends. The primary suite is a true retreat, featuring pool access, two walk-in closets, and a spacious en-suite bathroom with dual vanities, a soaking tub, and a separate walk-in shower. The home's triple-split layout provides excellent privacy, with two guest bedrooms sharing a full bathroom while the fourth bedroom is tucked away at the rear of the home behind a pocket door alongside the third bathroom, creating an ideal guest suite, in-law space, or home office. The third bathroom also serves as a pool bath. All guest bedrooms are generously sized, and one bedroom features sliding barn doors and a custom-made Lego wall. The interior laundry room adds convenience with built-in cabinetry and a hanging rack. Spend sunny Florida afternoons relaxing in the screen-enclosed swimming pool, lounging on the expansive pool deck, or enjoying shade beneath the covered lanai. The vinyl-fenced backyard offers exceptional privacy with no rear neighbors, creating a peaceful setting for entertaining, pets, or simply enjoying the outdoors. An irrigation well helps keep the landscaping lush while reducing monthly water expenses. Additional features include a generator connection with transfer switch (2024), new toilets (2023), rain gutters, garage work/storage station, extended driveway for additional parking, and more. Residents of Ruby Lake enjoy the security of a gated entrance along with a warm, neighborly atmosphere. Spend peaceful afternoons birdwatching by the scenic community pond, enjoy leisurely bike rides through the neighborhood, or connect with neighbors during an evening stroll along the quiet streets. Conveniently located in Winter Haven with easy access to Legoland FL, downtown restaurants, farmers markets, arts festivals, shopping and a vibrant nightlife scene. Centrally positioned between Tampa and Orlando, this location also provides convenient access to major airports, world-famous attractions, and beautiful Gulf and Atlantic Coast beaches. Combining quality craftsmanship, exceptional privacy, and a desirable location, this beautifully maintained pool home offers an outstanding opportunity to enjoy the very best of Florida living.

Listing is courtesy of: THE STONES REAL ESTATE FIRM (863-412-2080)

Listing Agent: Deanna Stone (863-412-2080)

Remarks: Welcome to this meticulously maintained 3-bedroom, 2-bath pool home located in the highly sought-after 24-hour guard-gated Cypresswood Golf and Country Club community of Winter Haven. Thoughtfully designed with a desirable split-bedroom floorplan, this residence offers both privacy and functionality for everyday living and entertaining. Plus, seller is currently in the process of installing a NEW ROOF! Step inside to find beautiful hardwood and tile flooring throughout, creating a warm yet low-maintenance living environment. The spacious primary suite serves as a private retreat, complete with direct access to the screen-enclosed pool deck — perfect for enjoying your morning coffee or an evening swim under the stars. The heart of the home flows seamlessly into a dedicated dining area, with an exciting bonus room just beyond featuring a fun wet bar — ideal for hosting gatherings, game nights, or creating your own lounge space. Two additional bedrooms are situated on the opposite side of the home, providing comfort and privacy for family or guests. Outdoors, the screened pool deck offers the perfect space for relaxing or entertaining year-round. The garage includes a dedicated workshop area, making it ideal for hobbyists, DIY enthusiasts, or extra storage needs. Beyond the home itself, residents enjoy an exceptional lifestyle within this premier community, featuring a championship 18-hole golf course, community pool, fitness center, clubhouse, on-site restaurant, and pro shop. Exciting new amenities are on the way, including lighted tennis courts, pickleball, and basketball courts — offering something for everyone. Whether you’re raising a family, welcoming visiting guests, or enjoying a seasonal escape, this home offers the space, setting, and lifestyle to fit every chapter. The Cypresswood 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! This is more than just a home — it’s a lifestyle. Schedule your private showing today!

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

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

Remarks: Short Sale. Welcome to this beautiful Winter Haven home! Villamar This property offers a spacious layout, abundant natural light, and comfortable living areas ideal for everyday living and entertaining. The backyard provides great outdoor potential. Conveniently located near shopping, dining, schools, and major highways. Short Sale opportunity — perfect for buyers looking for value and investment potential.

Listing is courtesy of: MY REALTY GROUP, LLC. (786-847-7421)

Listing Agent: Yoja Mirabal (407-543-7789)

Remarks: Welcome home to this immaculate 4 bedroom / 2 bathroom / 2 car garage home in Winter Haven! Shows like a model! No CDD! Low HOA fees, and lower taxes. GREAT OPEN FLOORPLAN with lots of living space, this home was BUILT IN 2024 and has plenty of features throughout. The home has tiled flooring throughout the main living areas and a huge great room, perfect for entertaining! The kitchen features a spacious center island, granite countertops, stainless steel appliances, tiled backsplash, and plenty of cabinetry space. There are 4 spacious bedrooms. The owner's suite boasts an en suite bathroom with dual sinks. The backyard is generously sized and is FULLY FENCED and includes a screened patio and a shed for a perfect outside living experience for relaxing, entertaining and family gatherings. Lots of upgrades! Close to shopping, dining, and Legoland. Perfectly situated between Orlando and Tampa .

Listing is courtesy of: RIGHT TRACK REALTY (954-437-4747)

Listing Agent: Phyllis Haigler (804-641-9763)

Remarks: One or more photo(s) has been virtually staged. Welcome to Peace Creek Reserve! Built in 2024, this move-in ready home offers the benefits of newer construction without the wait. Featuring 4 bedrooms, 3 full bathrooms, and a private in-law suite complete with its own kitchen and full bath, this flexible floor plan is ideal for multigenerational living, extended family, guests, or a private home office setup. The spacious main kitchen serves as the heart of the home, showcasing a center island with sink, abundant cabinetry, and an open-concept design that flows seamlessly into the living areas. Tile flooring extends throughout the main living spaces, while the bedrooms provide the comfort of carpeting. The primary suite offers a generous bedroom, walk-in closet, and private bath with dual vanities. Three additional bedrooms and two full baths provide plenty of room for family and guests. Step outside to the covered rear lanai and backyard, perfect for relaxing or entertaining. Conveniently located in Peace Creek Reserve, residents enjoy onsite pool and playground as well as easy access to shopping, dining, medical facilities, schools, and major commuter routes. Why wait months for new construction when you can move into this nearly new home today?

Listing is courtesy of: REDFIN CORPORATION (617-458-2883)

Listing Agent: Amy Long (863-712-9827)

Remarks: Whether you are looking for your first home or first rental property, this condominium is a must see! Ideally located off of Overlook Drive in Winter Haven, minutes form Legoland, downtown Winter Haven, and the Chain of Lakes. This unit features an updated kitchen with an upgraded stainless steel gas stove, stainless steel dish washer, and a one-year-old refrigerator. Additionally, there are newer dual pane windows, tile throughout the living area, and vinyl plank floors in the bedrooms! The air conditioner is only two years old and has a warranty that expires in 2033 and the washer/dryer is only one year old. The interior walls were just painted and this unit is ready for a new owner or tenant! This is one of the nicest units in the complex! Call today to schedule a showing!

Listing is courtesy of: CLARK REALTY LLC (863-345-2155)

Listing Agent: Steven Perkins (863-797-7276)

Remarks: Under Construction. The Glen is one of our two-story townhome floorplans featured in our Harmony at Lake Eloise community in Winter Haven, Florida. Welcome to this stylish and modern townhome nestled in a serene community. Boasting three spacious bedrooms, two and a half luxurious baths, and a convenient two-car garage, this residence offers the perfect blend of comfort and functionality. This all-concrete block construction home is sure to please, with 1,673 square feet, 3 bedrooms and 2 and a half bathrooms. Step inside to discover sleek, contemporary design elements complemented by high-end finishes throughout. The open concept living area is ideal for both relaxation and entertainment, featuring a kitchen equipped with stainless-steel appliances, granite countertops, and ample cabinet space. Enjoy seamless indoor-outdoor living with a covered rear lanai, perfect for dining or simply soaking in the sunshine. Upstairs, the primary bedroom serves as a tranquil retreat, complete with a lavish ensuite bath featuring dual sinks and a separate walk-in shower. Two additional bedrooms offer flexibility for guests, home offices, or hobbies, while a convenient laundry room adds practicality to daily life. Experience the ultimate convenience with smart home technology integrated throughout, allowing you to control lighting, temperature, security, and more with ease. With energy-efficient features and modern amenities, this townhome provides a sophisticated urban lifestyle in a desirable location. 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: Under Construction. New construction home with 2227 square feet on two-story including 4 bedrooms with loft, 3.5 baths, and an open living area. Enjoy an open kitchen with Quartz countertops, Samsung stainless steel appliances, a walk-in pantry, and a spacious island, fully open to the dining café and gathering room. The living area, laundry room, and baths include luxury wood vinyl plank flooring, with stain-resistant carpet in the bedrooms. Your owner's suite is complete with a walk-in wardrobe and a private en-suite bath with dual vanities, and a tiled shower. Bedrooms 2 and 3 share a jack-and-Jill bathroom. Plus, enjoy a covered lanai, 2-car garage, custom-fit window blinds, architectural shingles, energy-efficient insulation and windows, and a full builder warranty. “Please note, virtual tour/photos showcases the home layout; colors and design options in actual home for sale may differ. Furnishings and decor do not convey."

Listing is courtesy of: CAMBRIDGE REALTY OF CENTRAL FL (863-797-4999)

Listing Agent: George Lindsey, Iii (863-797-4999)

Remarks: Welcome to this beautifully updated 4-bedroom, 2-bathroom pool home in desirable Southeast Winter Haven. This move-in ready residence sits on a spacious lot with fantastic curb appeal and an incredible backyard oasis. Extensively updated in 2019 and meticulously maintained, the home features an open, light-filled layout with fresh white walls, stylish luxury vinyl flooring, and a cozy brick fireplace. The kitchen offers white cabinetry, stainless steel appliances, quartz countertops, and a dining area perfect for entertaining. The property includes four generous bedrooms—including a primary suite with a walk-in closet—versatile spaces for work or play, and a charming entry gallery. Additionally, a new roof was installed in January 2021. The backyard was further enhanced in 2025 with a complete pool renovation, a new paver deck, and a screened patio. This large covered area with ceiling fans overlooks the refinished pool, while the fully privacy-fenced yard provides ample room for recreation. Conveniently located near local amenities, schools, LEGOLAND, and the Chain of Lakes, this home perfectly combines comfortable living with the Florida lifestyle. Call today to schedule your private tour, this is a gem you won't want to miss!

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

Listing Agent: David Craig (863-605-3437)

Remarks: Under Construction. This two-story Georgia will definitely be on your mind… This beauty highlights a modern open layout, seamlessly integrating a first-floor kitchen with a central island, a dining room and a welcoming family room with patio access. On the same level is a private owner's suite with an attached bathroom. Situated upstairs is a versatile loft for additional shared living space and four secondary bedrooms to provide restful retreats to family members and guests alike. 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: Under Construction. The first floor of the stunning Edison two-story home is host to an open-concept layout that combines the kitchen with the living and dining areas, and an outdoor patio is easily reached off the main living space. Upstairs, five bedrooms surround a versatile loft, including the luxe owner’s suite, complete with a generous walk-in closet and en-suite bathroom. 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: Come see 2953 Whispering Trails Dr, a residence showcasing recent fresh interior paint and fresh exterior paint for a clean, cohesive appearance. The kitchen is equipped with all stainless steel appliances, and the primary bathroom provides practical double sinks. Outside, a welcoming patio leads to a fully fenced in backyard. This move-in ready property blends comfort and recent updates seamlessly. 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: One or more photo(s) has been virtually staged. Under Construction. BELOW MARKET INTEREST RATES with use of Seller's Preferred Lender. Welcome to The Azure, where modern design meets practical living in a home that has it all. With 4 bedrooms, 2.5 bathrooms, and a 2-car garage, this home is crafted for comfort and style. The extraordinary elevation and professionally designed landscaping create a captivating first impression. Step through the front door to discover luxurious vinyl plank flooring that extends throughout the open-concept layout. The kitchen shines with quartz countertops and all-new stainless-steel appliances, overlooking the dining area and patio. A convenient half bath is located downstairs for guests, while the spacious laundry room upstairs comes complete with a brand-new washer and dryer. Upstairs, you’ll find all four bedrooms, including the expansive owner's suite with a walk-in shower, double vanities, and a spacious walk-in closet. A flexible recreation space upstairs provides an ideal spot for family gatherings. With a smart thermostat ensuring energy efficiency and comfort, the Azure seamlessly blends functionality and modern luxury. 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: Turnkey Airbnb opportunity in the heart of Winter Haven! This fully furnished 4-bedroom, 2-bath pool home is perfect for short-term rental income, multi-generational living, or your next investment property. Featuring a flexible multi-generational layout and a suite with its own entrance, the home includes a private in-law suite, creating the ideal setup for guests or extended family. Recent updates include a new roof installed in 2023 for added peace of mind. Inside, you'll find bright and spacious living areas, a functional kitchen with ample cabinet and counter space, and comfortable bedrooms designed for relaxing stays. Outside, enjoy a fully fenced backyard with a private in-ground pool, plenty of room to entertain, and space to unwind. The large driveway and oversized 2-car carport provide ample parking for guests, boats, or multiple vehicles. With no HOA and the property being sold fully furnished, this move-in-ready home offers incredible flexibility as a primary residence, vacation getaway, or income-producing Airbnb. Conveniently located near shopping, dining, schools, and area attractions.

Listing is courtesy of: EXP REALTY LLC (407-706-5000)

Listing Agent: Daniel Betancourt (407-375-9142)