Homes For Sale in Winter Haven 33884 - 435 homes

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: Discover your dream home without the hassle! This stunning two-year old construction features all the modern upgrades you desire. Why buy new when you can purchase this like-new home with so many stylish finishes and energy efficient appliances. 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 upgraded 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 whether you are relaxing, entertaining or hosting family gatherings. Lots of upgrades! Close to shopping, dining, and Legoland. Perfectly situated between Orlando and Tampa .

Listing is courtesy of: RIGHT TRACK REALTY (953-437-4747)

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

Remarks: DON'T WAIT OPPORTUNITY IN CEDAR COVE Inside, the home offers a thoughtful split of comfort and function with 3 bedrooms and 2 baths, including a private primary suite featuring dual walk-in closets and a beautifully updated bath with a sleek tiled walk-in shower and designer-inspired finishes. Secondary bedrooms include built-ins, creating versatile space for a home office, hobby room, or guest accommodations. The kitchen is designed for both everyday living and entertaining, offering abundant cabinetry, generous prep space, stylish finishes, and an oversized secondary pantry for exceptional storage. Throughout the home, natural light pours in through skylights and expansive windows, highlighting soaring ceilings, durable hard-surface flooring, and a warm fireplace that anchors the main living space. Step outside and feel the difference. This is where Florida living shines. A spacious fenced backyard shaded by majestic oak trees creates a private retreat, complete with a screened lanai, brick paver patio, storage shed, and double gate access. It's ideal for weekend gatherings, quiet evenings, and effortless indoor-outdoor living. VALUE AND PEACE OF MIND ARE BUILT IN: With an acceptable offer, the seller will provide a NEW ROOF before closing and a NEW WATER HEATER already installed, making this a rare, move-in-ready opportunity with major updates already handled. Located just minutes from Tampa and Orlando, this SE Winter Haven cul-de-sac home offers quick access to major airports, world-famous attractions, top dining, shopping, schools, medical facilities, and LEGOLAND Florida. Whether for commuting or weekend escapes to Gulf or Atlantic beaches, the location delivers unmatched convenience and lifestyle flexibility. Homes with this combination of location, outdoor space, and upgrades are hard to find. Schedule your showing before it's gone.

Listing is courtesy of: CENTURY 21 BEGGINS ENTERPRISES (813-658-2121)

Listing Agent: John Evans (813-992-3483)

Remarks: Welcome to the Spring model in Peach Crossings, a spacious five-bedroom, three-bathroom, two-story home perfectly positioned on a premium corner lot with no rear neighbors, offering added privacy and an open, peaceful setting. From the moment you walk through the door, you’re greeted by a long, inviting foyer that sets the tone for this warm and welcoming home. The first floor features a bright, open-concept family room that’s perfect for entertaining or everyday living. The modern kitchen is designed with both style and function in mind, showcasing a large island with breakfast bar seating, plenty of cabinet space, and brand-new Whirlpool appliances. A downstairs guest bedroom and full bathroom provide the perfect setup for visitors, multigenerational living, or a private home office. Upstairs, the spacious owner’s suite offers plenty of room for a king-sized bed, additional furniture, and even a cozy sitting area or reading nook. The en-suite bathroom includes dual vanities, a linen closet, and an oversized walk-in closet with ample storage. The additional bedrooms are all generously sized, giving everyone their own comfortable space while also offering flexibility for a playroom, gym, office, or hobby room. With three full bathrooms throughout the home, busy mornings are made easy. You’ll also love the oversized upstairs laundry room complete with extra storage and a dedicated closet for added convenience. Step outside and enjoy the covered back patio and charming covered front porch ideal for relaxing with your morning coffee or entertaining guests year-round. Located in the highly desirable Peach Crossings community, this move-in-ready home offers easy access to top-rated Polk County schools, shopping, dining, and local attractions. Best of all, all upgrades are already included, making this home truly turnkey. Schedule your private showing today!

Listing is courtesy of: LA ROSA REALTY CW PROPERTIES L (407-910-2168)

Listing Agent: Kennia Lozada Rivera (407-259-9096)

Remarks: Virtually Staged. Welcome to this beautiful home in peace creek reserve! this thoughtfully designed single-story residence offers 4 bedrooms and 2.5 bathrooms, combining comfort and functionality. The open-concept floor plan seamlessly connects the family room, dining area, and kitchen—complete with a central island—creating the perfect space for everyday living and entertaining. Located in the desirable peace creek reserve community, residents enjoy a serene setting surrounded by nature, including a picturesque creek. situated in winter haven—known as the chain of lakes city with over 26 connected lakes—this area offers a variety of shopping, dining, and outdoor activities such as biking and water recreation. Peace creek reserve provides the perfect balance of a peaceful, small-town atmosphere with everyday convenience—an ideal place to call home.

Listing is courtesy of: GLASSTONE GROUP INC (321-988-4663)

Listing Agent: Barbara Cunha De Freitas (617-458-0838)

Remarks: PRICE REDUCTION! Spacious 2,336 SF pool home in the gated, tranquil Overlook Estates. This 4BR/2BA floorplan features a split-bedroom layout and generous living space including an eat-in kitchen, 17x18 vaulted family room, 10x16 dining room with bay window, and a large foyer. The master suite includes a dressing alcove and walk-in closet; an adjacent bedroom makes an ideal office or nursery. High-traffic areas feature tile flooring; sliding glass doors in three rooms recess into the wall and open to a 31x50 pool deck — perfect for indoor/outdoor living. Additional highlights: 95x130 lot, terraced front walkway, 7x8 laundry with cabinetry and utility sink, 22x23 garage with built-in storage, tankless water heater, and leaf filter gutter guards. Ready for your finishing touches!

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

Listing Agent: Amy Reynolds (863-412-2279)

Remarks: Under Construction. *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: Spacious 3-Bedroom Home with Investment Potential Welcome to this beautifully maintained home featuring three generously sized bedrooms, including a primary suite with a walk-in closet, offering ample storage and comfort. The two additional bedrooms each feature built-in closets, perfect for family, guests, or tenants. Enjoy the convenience of two full bathrooms, a bright and open floor plan, and expansive living and dining areas that create the perfect space for entertaining or relaxing. The modern kitchen is both stylish and functional, ready for daily cooking or hosting gatherings. Additional highlights include a 2-car attached garage for secure parking and storage, and ceiling fans in all bedrooms and the living room, ensuring comfort and energy efficiency year-round. The home is also equipped with seamless gutters around the entire house, offering long-term durability and low maintenance. Whether you're looking for a primary residence or a smart investment property, this home checks all the boxes. With its spacious layout, attractive features, and low-maintenance upgrades, it’s a fantastic opportunity for investors seeking long-term value and strong rental appeal. Don't miss out—schedule your showing today and discover the potential this property offers!

Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)

Listing Agent: Osvaldo Junior (407-693-3133)

Remarks: Charming and well-maintained and can be your HOME in Winter Haven! This property features a functional open concept floor plan with soacious living areas to entertain the entire family. This property is perfect for starter or investment! Schedule your private showing today. Buyer shall verify all the measuremetns provided herein.

Listing is courtesy of: HOMES UNLIMITED REAL ESTATE CORP (407-378-5600)

Listing Agent: Waleska Rodriguez Leon (407-929-2734)

Remarks: Under Construction. Brand new, energy-efficient home available by Jul 2026! An open floorplan that makes entertaining easy in the open kitchen, dining, and great room that flow to the patio. The primary suite is tucked in the rear of the home offering plenty of privacy and features a spacious walk-in closet and shower. Visit Villamar and explore new single-family homes for sale in Winter Haven, FL. Residents will have access to two resort-style amenity centers featuring a clubhouse, pool, and playground. Winter Haven is known for its beautiful chain of lakes with lakeside restaurants and its award-winning community theater. Nearby attractions include Legoland Florida and Peppa Pig Theme Park. A brand-new model and new phase are coming soon. Each of our homes is built with innovative, energy-efficient features designed to help you enjoy more savings, better health, real comfort and peace of mind.

Listing is courtesy of: MERITAGE HOMES OF FL REALTY (813-703-8860)

Listing Agent: Bryan Sumner (813-336-5895)

Remarks: Beautiful lake-view condo in Winterset! This ground-floor 2-bedroom, 2-bath residence offers amazing views of Lake Winterset, part of the renowned Winter Haven Chain of Lakes. The spacious great room features tile flooring, sliding glass doors to the screened porch, and stunning lakefront vistas. Just off the kitchen is a comfortable dining area, creating an inviting space for everyday living and entertaining. The kitchen is beautifully appointed with custom Kraft Maid wood cabinetry, granite countertops, a breakfast bar, and a complete appliance package. The primary bedroom enjoys peaceful lake views and includes plush carpeting with a gel pad, a large 11' X 7' walk-in closet, a ceiling fan, sliding doors to the patio, and an en-suite bath featuring dual sinks, quartz countertops, and an oversized walk-in shower with a seamless glass door. The guest bedroom is generously sized at 13' x 10', offering ample closet space and convenient access to the guest bathroom, which features quartz countertops and tile flooring. The screened porch is the perfect place to relax and enjoy breathtaking lakefront views and spectacular sunsets. Residents enjoy true resort-style living with access to a community clubhouse, pool, spa, shuffleboard courts, tennis & Pickleball courts. The highly desirable location offers close proximity to shopping, dining, schools, medical facilities, and LEGOLAND Florida Resort. Additional features include a private storage room off the patio, inside laundry, a tile roof, air conditioning, 24-hour security, meticulously maintained grounds, assigned parking, and ample guest parking. This is Florida lakefront living at its finest.

Listing is courtesy of: CROSBY & ASSOCIATES, INC. (863-293-5600)

Listing Agent: Chip Fortenberry, Iii (863-673-9368)

Remarks: NO CDD Fees • Low HOA • *Lower Taxes • Luxury Heated Pool • Resort-style backyard • Move-In Ready Home. Welcome to this beautifully maintained and gently lived-in upscale home situated on an oversized 70’ wide homesite in a desirable community offering low HOA fees and *lower property taxes. Designed for both comfort and entertaining, this expansive 4-bedroom, 3.5-bath, two-story home has approximately 2,894 sq. ft. of thoughtfully designed living space, including TWO primary suites — one conveniently located on the first floor with a luxury bath and spacious walk-in closet, and a second upstairs primary suite featuring its own full bath and walk-in closet. The first floor also includes a versatile enclosed flex room which can be used as a home office, guest room, or potential 5th bedroom. The second floor has three other bedrooms with walk-in closet and oversized loft about 21'x17'. Step outside into your private resort-style backyard featuring a heated, fully automated full-size pool and spa with premium PebbleTec finish, already prepped for expansion with a concrete footer for future screen enclosure installation, upgraded pavers, large covered lanai, gutters and downspouts for improved drainage, fully fenced yard and extended front porch — creating the perfect Florida outdoor living experience— for entertaining, relaxing, pets, and family gatherings. Inside, the open-concept kitchen is beautifully upgraded with: • premium color cabinets, • oversized island, • stylish backsplash, • single-bowl sink, • granite countertops, • pendant lighting, • and stainless-steel appliances. Additional interior highlights include: • recessed LED lighting throughout, • tile flooring in wet areas, kitchen, hallway, and gathering room, • exterior-vented microwave, • and abundant natural light throughout. This truly move-in-ready home includes: • first-floor family room sofa set with wall-mounted 75” TV, • upstairs loft recliner sofa set with wall-mounted 75” TV, • refrigerator, washer, dryer, and window blinds, • home alarm system, • outdoor security cameras, • video doorbell, • and remote thermostat. Additional peace of mind includes: • transferable Pulte Homes 5/10-year warranty, • and 1 year of complimentary pool maintenance. This home has the perfect blend of luxury, functionality, and convenience in a family-friendly community with a safe small-town feel while remaining close to shopping, dining, everyday amenities and just minutes away from Legoland. READY TO MOVE IN. *Some photos have been virtually rendered.

Listing is courtesy of: BEYCOME OF FLORIDA LLC (804-656-5007)

Listing Agent: Steven Koleno (804-656-5007)

Remarks: Under Construction. Brand new, energy-efficient home available by May 2026! Entertain guests with ease with an open kitchen which overlooks the dining and great room. First floor flex space can be best used to fit your needs. Upstairs primary suite features an oversized walk-in closet. Visit Villamar and explore new single-family homes for sale in Winter Haven, FL. Residents will have access to two resort-style amenity centers featuring a clubhouse, pool, and playground. Winter Haven is known for its beautiful chain of lakes with lakeside restaurants and its award-winning community theater. Nearby attractions include Legoland Florida and Peppa Pig Theme Park. A brand-new model and new phase are coming soon. Each of our homes is built with innovative, energy-efficient features designed to help you enjoy more savings, better health, real comfort and peace of mind.

Listing is courtesy of: MERITAGE HOMES OF FL REALTY (813-703-8860)

Listing Agent: Bryan Sumner (813-336-5895)

Remarks: Under Construction. Brand new, energy-efficient home available by May 2026! Open floor plan creates a unified living space with a large great room that overlooks the kitchen. Visit Villamar and explore new single-family homes for sale in Winter Haven, FL. Residents will have access to two resort-style amenity centers featuring a clubhouse, pool, and playground. Winter Haven is known for its beautiful chain of lakes with lakeside restaurants and its award-winning community theater. Nearby attractions include Legoland Florida and Peppa Pig Theme Park. A brand-new model and new phase are coming soon. Each of our homes is built with innovative, energy-efficient features designed to help you enjoy more savings, better health, real comfort and peace of mind.

Listing is courtesy of: MERITAGE HOMES OF FL REALTY (813-703-8860)

Listing Agent: Bryan Sumner (813-336-5895)

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. Brand new, energy-efficient home available by May 2026! An open floorplan that makes entertaining easy in the open kitchen, dining, and great room that flow to the patio. The primary suite is tucked in the rear of the home offering plenty of privacy and features a spacious walk-in closet and shower. Visit Villamar and explore new single-family homes for sale in Winter Haven, FL. Residents will have access to two resort-style amenity centers featuring a clubhouse, pool, and playground. Winter Haven is known for its beautiful chain of lakes with lakeside restaurants and its award-winning community theater. Nearby attractions include Legoland Florida and Peppa Pig Theme Park. A brand-new model and new phase are coming soon. Each of our homes is built with innovative, energy-efficient features designed to help you enjoy more savings, better health, real comfort and peace of mind.

Listing is courtesy of: MERITAGE HOMES OF FL REALTY (813-703-8860)

Listing Agent: Bryan Sumner (813-336-5895)

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. BRAND NEW REFRIGERATOR AND RANGE. 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)

Remarks: Lakefront Opportunity on Lake Elbert! This spacious 5-bedroom, 5.5-bath home sits on a large corner lot with a pool and offers endless potential for both investors and families searching for their dream waterfront home. Featuring a newer roof and newer A/C, the property has solid fundamentals and is ready for your personal updates and vision. Offered below market value, this is a rare chance to create significant equity and enjoy strong appreciation once renovated. Ideal for cash buyers or buyers using conventional financing. Sold As-Is. A unique opportunity to transform this property into a stunning lakefront estate in one of Winter Haven’s most desirable locations. Seller motivated!

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

Listing Agent: Santiago Brito (323-439-7896)

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: Nestled within the exclusive gated community of Tuscany, a charming neighborhood of just 18 homes in Southeast Winter Haven, this 4 bedroom, 3 bath pool home offers over 3,300 square feet under roof on a private 0.33 acre lot. Designed for both comfortable living and entertaining, the home features a dedicated office, formal dining room, living room, and an impressive 25' x 17' poolside bonus room complete with a custom wall-to-wall hardwood entertainment center, surround sound, upgraded lighting, tile flooring, and ceiling fan. The spacious kitchen showcases abundant Kraft Maid cabinetry, granite countertops, generous workspace, and a sunny breakfast nook overlooking the pool. A thoughtfully designed triple-split bedroom floor plan provides privacy for family and guests, while multiple access points lead to the screened pool and outdoor living areas. The spacious primary suite features a double-sink vanity, garden tub, separate shower, private water closet, and oversized walk-in closet. It also as access to the pool area. Additional highlights include hand-scraped real wood flooring throughout most of the home, including the primary suite, an outdoor summer kitchen with built-in gas grill, sink, and refrigerator, indoor laundry room, oversized two-car garage, expanded driveway with parking for up to eight vehicles, a separate entrance to the bonus room, and mature landscaping with an irrigation system on a dedicated meter. The large private backyard offers plenty of space beyond the screened pool area, creating a peaceful retreat while remaining conveniently located less than a mile from schools and Publix supermarket. Experience this exceptional property like never before with a 3D Interactive Virtual Tour or Virtual Reality featuring a 2D Floor Plan and immersive 3D Dollhouse Model, plus a 360-degree Interactive Aerial Virtual Tour showcasing the entire Tuscany community and panoramic views as far as the eye can see. The home features a stunning collection of modern gold crystal chandeliers throughout, including a 23.6" dimmable LED crystal chandelier with adjustable color temperatures in the hallways and kitchen, an elegant gold crystal flush-mount chandelier in the master bedroom, a large modern crystal LED chandelier that serves as a beautiful focal point in the living room, and a luxurious 40" gold rectangular crystal chandelier with 16 lights above the dining area, creating a cohesive, contemporary design with lighting and timeless elegance throughout the home. Meticulously maintained, this one-of-a-kind pool home is a rare opportunity to own a beautiful property in one of Southeast Winter Haven's most desirable gated communities.

Listing is courtesy of: 3D TEAM REALTY LLC (863-604-3662)

Listing Agent: Jimmy Aguilar (863-604-3662)