Winter Haven Homes For Sale & Real Estate - 805 homes

Remarks: Back on market, property passed inspections already. Welcome to 2683 Wyndsor Oaks Way, Winter Haven, FL – an extraordinary residence in the highly sought-after gated Wyndsor at Lake Winterset community, offering a luxurious lifestyle with lake access, tennis courts, and a playground. This stunning home blends timeless elegance with modern comforts, creating a perfect sanctuary for discerning buyers. As you enter, a gracious foyer welcomes you into a sunlit living area that exudes warmth and sophistication. The open layout features a cozy yet spacious living room, perfect for relaxing with loved ones. A formal dining area leads seamlessly into the gourmet kitchen, equipped with high-end stainless steel appliances, recently updated double ovens, exquisite granite countertops, and ample custom cabinetry. This thoughtfully designed home offers flexibility and functionality, including a versatile den/bonus room on the main floor, ideal as a home office, playroom, or entertainment space. The oversized primary suite on the main level is a true retreat, featuring a spa-like en-suite bath with dual vanities, a luxurious soaking tub, a walk-in shower, and generous closet space. Step outside to your own private paradise – a serene outdoor haven with a sparkling pool, lush landscaping offering amazing pond views. The pool’s salt cell has been recently replaced, ensuring easy maintenance for years to come. The expansive patio invites al fresco dining, summer gatherings, and tranquil evenings under the stars. Upstairs, you’ll find three well-appointed guest bedrooms and a media room all with recently updated flooring, There are two additional guest bathrooms, providing comfort and privacy for family and guests alike. Additional highlights include a three-car garage, offering plenty of storage and convenience and plenty of parking space including a circular paved driveway. Located in the heart of Winter Haven, this home offers central access to both Tampa and Orlando. It is just minutes from Legoland and approximately 1.5 hours from Florida’s beautiful east and west coasts, making it ideal for those who appreciate both convenience and adventure. Don’t miss this rare opportunity to call 2683 Wyndsor Oaks Way your forever home – schedule your private showing today!

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

Listing Agent: Patricia De Graaff, Llc (863-307-0061)

Remarks: Welcome to 6044 Grand Oaks Dr SE in Winter Haven, a beautifully updated waterfront home in the desirable 55+ community of Garden Grove Oaks, where you OWN THE LAND! Enjoy peaceful water views right from your backyard and take advantage of a recent $15,000 price improvement, making this home an incredible value. This charming 2-bedroom, 2-bath residence offers the perfect blend of comfort, modern updates, and Florida lifestyle living. The spacious and open floorplan features laminate flooring throughout the main living areas, creating a bright and inviting atmosphere. The kitchen has been tastefully updated with new cabinet facings, countertops, and stainless steel appliances, offering both style and functionality. The Florida room, complete with vinyl plank flooring, updated sliding doors, and custom blinds, provides the perfect spot to relax and soak in the tranquil water views. Additional updates include double-pane windows throughout, as well as refreshed flooring, toilet, and faucets in the guest bathroom. The primary suite offers a barn door entry and private ensuite bathroom, while the guest bedroom provides flexibility for visitors or a home office. Garden Grove Oaks is a welcoming, well-maintained community offering a heated pool, clubhouse, and active social calendar, all with NO LOT RENT. With its waterfront setting, modern updates, and excellent value, this home is truly move-in ready. Don’t miss the opportunity to make it yours, schedule your private showing today!

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

Listing Agent: Patricia De Graaff, Llc (863-307-0061)

Remarks: Welcome to easy, low-maintenance Florida living in this fully furnished 1 bedroom, 1 bathroom ground-floor condo located in the well-established Winter Haven Harbour community! Ideally positioned with direct views of the pool and shuffleboard courts, this unit offers both convenience and a relaxed lifestyle. Step inside to find a move-in ready space complete with living room furniture, bedroom furnishings, dining set, and a fully equipped kitchen. Many furnishings are brand new and have never been used. This is perfect for seasonal living, downsizing, or a full-time residence. The ground-floor location provides easy access with close proximity to elevators, laundry facilities, mailboxes, and the community bulletin board. Enjoy everything this quiet and well-maintained community has, including a resort-style pool, shuffleboard courts, clubhouse, fitness area, and multiple outdoor seating and gathering spaces. Each unit includes assigned covered parking and a dedicated storage area, along with additional guest parking available. The monthly association fee covers water, sewer, trash, grounds maintenance, and upkeep of all community amenities—making for truly stress-free living. Whether you’re a snowbird, retiree, or simply looking to simplify your lifestyle, this condo offers the perfect opportunity to enjoy Florida living at its best. Move right in as-is or you have the opportunity to update to your personal taste!

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

Listing Agent: Aubrie Flint (863-618-6347)

Remarks: Welcome to 2849 Cathy Blvd, Winter Haven, FL 33880—a beautifully designed ranch-style home offering an airy, open-concept layout centered around a spacious great room and a modern kitchen, perfect for both everyday living and entertaining. The kitchen features quartz countertops, stainless steel appliances, and elegant 42" white upper cabinets, while the bathrooms showcase cultured marble finishes for a clean, polished look. The private primary suite includes a generously sized bedroom, a large en-suite bath, and a walk-in closet. Step outside to enjoy the covered screened in patio—ideal for relaxing or hosting gatherings year-round with the privacy of your fenced in yard!. All appliances included, adds to the home’s move-in ready appeal. Conveniently located in Winter Haven, this home offers easy access to shopping, dining, and entertainment, including nearby grocery stores, local restaurants, and parks. Just a short drive to downtown Winter Haven, you can enjoy the Chain of Lakes, outdoor recreation, and community events. With close proximity to major roadways, commuting to Lakeland, Orlando, and surrounding areas is a breeze.

Listing is courtesy of: KELLER WILLIAMS ADVANTAGE III (407-207-0825)

Listing Agent: Krichely Gonzalez Rodriguez (407-953-4377)

Remarks: This property is a RENT TO OWN OPPORTUNITY!!! Enjoy relaxed Florida living with beautiful lake views right from the front of this inviting home. Filled with natural light, the comfortable layout offers an easy, functional flow that makes everyday living and entertaining feel effortless. The thoughtfully designed interior keeps maintenance simple while maximizing comfort and usability. One of the home’s standout features is the fully fenced yard, providing privacy, security, and plenty of space for pets, gatherings, gardening, or creating your own outdoor retreat. Paired with the peaceful water views, the setting creates a welcoming atmosphere that feels both calm and connected. Perfect for first-time buyers, downsizers, seasonal residents, or investors, this home offers charm, outdoor space, and scenic surroundings — all while providing a flexible path to ownership in a highly desirable Central Florida setting.

Listing is courtesy of: IAD FLORIDA LLC (407-720-0020)

Listing Agent: Catherine Torres (863-632-4177)

Remarks: Beautifully renovated property in an excellent and highly desirable location. This home features modern finishes throughout, including a stunning quartz kitchen countertop and brand-new appliances. Conveniently located near hospitals, medical offices, major avenues, schools, restaurants, and shopping centers. Its strategic location offers great versatility, making it ideal for both residential living and potential commercial use. A rare opportunity to own a fully updated property in a prime area.

Listing is courtesy of: LA ROSA REALTY KISSIMMEE (407-930-3530)

Listing Agent: Graceshaly Collazo (939-441-3991)

Remarks: Back on the market, home appraised over list price buyer lost job before closing. This home boast over 1614 heated living square foot. The home has tile floor and wood throughout all rooms. The large kitchen has solid stone granite counter tops and a large breakfast bar. The seller will credit the buyer for a brand new roof from one of their recent quotes of $10,600 at time of closing (See attached roof est). The large fully fenced in backyard is perfect for entertaining or pets. There is a one car detached garage in the backyard and the shed also conveys.

Listing is courtesy of: MAZELG REALTY (863-399-0226)

Listing Agent: Eric Sigismondi, Llc (863-651-9257)

Remarks: Fully renovated 3BR/2BA home with an open space perfect for office or extra space located in Winter Haven NO HOA! New Roof, New AC, New Water Heater, New Flooring, New Kitchen Cabinets, updated bathrooms cabinets, and modern finishes throughout. Turn-key and move-in ready with a spacious yard and great location. Huge fenced backyard with banana trees Plus, NO HOA — enjoy more freedom and lower monthly costs Don’t miss it!

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

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

Remarks: Short Sale. One of the most sought-after floor plans, this 4-bedroom, 2-bathroom home boasts numerous charming features and is set on an oversized lot with no rear neighbors and a serene water view. As you enter, you'll find three spacious bedrooms and a modern bathroom. To the left, the inviting, contemporary kitchen showcases a large pantry offering ample storage space. The open dining area flows seamlessly into the airy living room, creating a perfect space for gatherings. Step outside to your private screened-in patio and enjoy the expansive yard with a tranquil, picturesque view. The luxurious Master Suite features dual sinks and a generous walk-in closet. The kitchen island and open layout are perfect for entertaining. This home comes complete with all major appliances, blinds, and is equipped with Smart Home Technology, including Alexa. Conveniently located near I-4, shopping, and entertainment, and offering access to a community pool. All of this at an unbeatable price in an up-and-coming location!

Listing is courtesy of: KELLER WILLIAMS ADVANTAGE III (407-207-0825)

Listing Agent: Krichely Gonzalez Rodriguez (407-953-4377)

Remarks: Welcome to one of THE MOST DESIRABLE AND BEAUTIFUL 55+ GATED communities in Winter Haven, FL! MOTIVATED SELLERS!!! LAKE ASHTON has great amenities for their residents to enjoy. An enormous club house were events are held, two pools, dog park and more. This gorgeous well maintained home has MULTIPLE UPGRADES that the future owner would enjoy. NEW ROOF, AC AND WATER SOFTENER WERE INSTALLED ON 2023. ROOF has a special insulation for climate control inside the house and a warranty of 25 years from day of installation. NEW WIND IMPACT AND DOUBLE PANEL WINDOWS WERE INSTALLED ON 2022, A NEW MICROWAVE ON 2025, NEW SMART GARAGE DOOR OPENER ON FEBRUARY 2026. Kitchen has been UPGRADED WITH AN ELEGANT QUARTZ COUNTERTOP. THIS HOME HAS BEAUTIFUL CERAMIC TILE ALL OVER THE HOUSE AND GUEST BATHROOM HAS BEEN UPDTADED TO AN ASSESIBLE BATH. SOLAR PANELS WERE INSTALLED AND THEY ARE PAID OFF helping to lower the electric bill cost. This is great for the new owner. A selective landscaping has been installed with gorgeous plants giving the feeling of been surrounded by nature. On the garage you will find cabinets for your storage, an epoxy floor and TANKLESS WATER HEATER saving space for more storage. COME AND SEE THIS AMAZING HOME THAT WILL MAKE YOU FEEL IN PARADISE!

Listing is courtesy of: LA ROSA REALTY LLC (321-939-3748)

Listing Agent: Francis Alvarez Lopez (787-564-4822)

Remarks: Don’t Miss This Opportunity! This fixer-upper offers amazing potential and features 4 bedrooms and 2 full baths, making it ideal for homeowners or investors. The kitchen includes a cozy dinette area, great for family gatherings, while the spacious living room opens to a screened front patio, providing extra space to relax. The primary bedroom is generously sized, offering a walk-in closet and an upgraded full bath with attractive tile. The second bathroom has also been updated by the previous owner. This home is a great candidate to be transformed into your ideal living space or added to your rental portfolio. Property is being sold As-Is. All buyers MUST view the home in person before submitting an offer. Opportunities like this don’t last—schedule your showing today before it’s gone!

Listing is courtesy of: REALTYCITY INC (863-438-6605)

Listing Agent: Jesse Carriedo (863-438-6605)

Remarks: Spacious two-story home offering 5 bedrooms, 2.5 bathrooms, a dedicated office/flex room, and approximately 2,952 heated square feet in a quiet Winter Haven community. The kitchen features granite countertops (2021), a center island, large pantry, abundant cabinetry, and newer stainless-steel appliances, including a WiFi-enabled smart refrigerator. The kitchen opens to a generous living area, creating an ideal layout for everyday living and entertaining. A formal dining room, half bath, and versatile office/flex room (possible 6th bedroom) complete the main level. A storage closet under the stairs plus multiple additional closets provide excellent storage throughout. Upstairs includes all five bedrooms plus a spacious loft overlooking the foyer. The primary suite features vaulted ceilings, a garden tub, separate shower, and ample closet space. Secondary bathroom includes a tub/shower combination. Laundry hookups are conveniently located upstairs for added functionality. Major updates include a NEW roof, NEW A/C units (2022), updated water system, and solar panels (solar to be assumed by buyer). The fully fenced backyard offers a concrete patio, fire pit area, and newly seeded lawn areas. A concrete wall at the rear of the property adds privacy and helps minimize traffic noise. The neighborhood features paved sidewalks, street lighting for evening walks, and two community ponds — including one across the street where fishing is permitted. Conveniently located near schools, lakes, shopping, dining, and major roadways.

Listing is courtesy of: CITARELLI REALTY GROUP LLC (321-607-3586)

Listing Agent: Ambre Leblanc (407-494-8334)

Remarks: BACK ON MARKET DUE TO BUYERS FAILED FINANCING!! MAGNIFICENT 4BR/3BA POOL HOME!! Located in the gated Winter Haven subdivision of Tuscanny, this exquisitely maintained one story home, with approx. 3,242 sqft including an air conditioned sunroom, has so much to offer; it showcases a full GUEST SUITE and a new roof as of April 2021! Fantastic Features include: crown molding, ceramic tile, laminate flooring in all 4 bedrooms, updated granite countertops, sinks and fixtures, volume ceilings and fresh paint. The Kitchen is a chefs dream!! It has stainless steel appliances with a Subzero fridge, custom maple cabinetry, gas range with a restaurant style warming lamp and commercial vent, accent lighting, and a large walk-in pantry. A spacious family room flows off the kitchen and overlooks the pool, patio, and air conditioned Florida room. The luxurious Master Suite showcases tray ceilings and dual walk-in closets, with a well-appointed en suite Master Bath, including dual vanities, walk-in shower, a jetted tub and a water closet for privacy. The GUEST SUITE has its own private full en suite bathroom. There are 2 additional bedrooms and a guest bathroom, which also connects as a pool bath with outside access. The air conditioned enclosed sunroom is just off the master bedroom, through the French doors, overlooking the pool; perfect to enjoy your morning coffee, and adding great flow to the well thought out floor plan. The pool and deck have been repainted in recent years, and pool AND BUILT IN HOT TUB area have been re-screened. A BBQ patio has been newly added out back for an expansion of the outdoor enjoyment. Also added, a privacy fence tree line and poolside sun shades ensuring separation from rear neighbors. There is an OVERSIZED 2 car side garage, large pavered CIRCULAR DRIVEWAY, attractive mature landscaping, and MORE!!! All this in a beautiful gated community just minutes from LEGOLAND, Disneyworld, and Universal Studios! This well appointed home is PRICED TO SELL. What are you waiting for???! Seller is also the listing agent.

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

Listing Agent: Marissa Taranto (888-883-8509)

Remarks: Brand new, energy-efficient home available by Oct 2025! Prepare dinner while catching up on the days events from this homes chef-inspired kitchen which overlooks a great room and dining area. Well appointed primary suite provides a restful retreat at the end of the day and has a spacious 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: One or more photo(s) has been virtually staged. 943 Summer Glen Dr is a spacious and well-maintained home offering exceptional value in the heart of Winter Haven. This move-in-ready residence features a functional, open floor plan designed for modern living and effortless entertaining. The bright, airy interior flows seamlessly into versatile living spaces, including a comfortable primary suite and additional bedrooms perfect for a growing family or a dedicated home office. Positioned in a quiet, family-oriented community, this property sits just moments from top-rated schools like Lake Shipp Elementary and the renowned Jewett School of the Arts. Residents enjoy immediate access to the Chain of Lakes for premier boating and fishing, as well as the dining and boutiques of historic downtown Winter Haven. Perfectly situated between Orlando and Tampa, this home provides a high-quality lifestyle and significant appreciation potential without the metropolitan price tag. Schedule your private showing today to discover why 943 Summer Glen Dr is the perfect place to start your next chapter!

Listing is courtesy of: KELLER WILLIAMS REALTY AT THE LAKES (407-566-1800)

Listing Agent: Stacey Vazquez (407-874-5751)

Remarks: Welcome to your dream home in the heart of Villamar, where modern living meets serene surroundings. This stunning four-bedroom, two-bathroom residence is perfectly situated on a desirable corner lot, offering privacy and tranquility with no backyard neighbors, as it backs up to a lush conservation area and a picturesque pond. Step inside to discover a bright and airy open-concept design, accentuated by high ceilings that create an inviting ambiance. The gourmet kitchen is a chef's delight, featuring sleek stainless steel appliances, a spacious island with seating for up to six, and elegant decorative lighting that enhances the space. The stylish tile backsplash adds a touch of sophistication to this culinary haven. Retreat to the expansive primary bedroom, where a tray ceiling enhances the sense of luxury. The en suite bathroom completes the suite with a private water closet, a large walk-in shower, dual sinks, a generous walk-in closets, providing ample storage and comfort. This home is designed for modern convenience, featuring a designated indoor laundry room and a host of upgrades, including a water softener system with reverse osmosis. Step through the sliding glass doors to the screened-in lanai, equipped with a ceiling fan and epoxy flooring, perfect for enjoying Florida's beautiful weather. The private backyard, enclosed by a vinyl fence, offers a secure space for relaxation or play. Additional highlights include a spacious two-car garage and access to the community pool, ideal for those hot summer days. Located close to the enchanting Chain of Lakes and Legoland, as well as an array of shopping and dining options, this home promises a lifestyle of comfort and convenience. Don't miss the opportunity to make this exceptional property your new home. Schedule a viewing today and experience all that this remarkable residence has to offer!

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

Listing Agent: David Small (407-601-8351)

Remarks: SELLER MOTIVATED!!! Welcome to this stunning corner-lot home located in the desirable community of Harmony on Lake Eloise — just minutes from LEGOLAND and perfectly situated between Tampa and Orlando! This beautifully designed property offers a modern open-concept floor plan ideal for today’s lifestyle. Step inside to find elegant shaker-style cabinets, quartz countertops, and a stainless-steel range hood vented to the exterior. The kitchen is fully equipped with Whirlpool stainless-steel appliances including range, dishwasher, refrigerator, washer, and dryer — all included! The spacious layout provides comfort and style with thoughtful upgrades throughout. The large corner lot offers a generous backyard, perfect for entertaining, relaxing, or even building your dream outdoor space. Built with quality in mind, the home features block-on-block construction, architectural shingles, and a sleek stucco exterior for long-lasting durability and curb appeal. Inside, integrated smart home technology allows you to control lighting, temperature, and more — all from the palm of your hand. Living in Harmony on Lake Eloise means enjoying Florida’s outdoor lifestyle with access to the Chain of Lakes, nearby parks, shopping centers, restaurants, and golf courses. Plus, with easy access to major highways, commuting is a breeze. Don’t miss your chance to own this move-in-ready home in one of Central Florida’s most convenient and charming communities!

Listing is courtesy of: PREFERRED REAL ESTATE BROKERS (407-440-4900)

Listing Agent: Antonio Chacon (407-227-4683)

Remarks: PRICE REDUCED!!!WELCOME to this beautiful 4-bedroom, 2-bath home, built in 2018, offering 1,755 sq. ft. of comfortable living space on a spacious 0.24-acre fenced lot. Located in a desirable area close to shopping, dining, and major roads, this home is perfect for those seeking both convenience and a peaceful neighborhood feel. Step inside and you'll love the bright and airy vaulted great room and the open floor plan, ideal for entertaining or everyday family living. The home features laminate & ceramic flooring throughout the main areas with cozy carpet in all bedrooms. The kitchen is a standout with its beautiful cabinetry, handmade extra shelving, all the appliances, tile backsplash, and plenty of counter space for cooking and gathering. Eagle crest is also a natural gas community, enjoying nonstop hot water with a tank less water heater. Additional thoughtful upgrades include ceiling fans in every room, custom made wood door casings and trim, washer and dryer included, and a screened lanai — the perfect spot to unwind and enjoy the outdoors. The fully fenced backyard provides privacy, security, and space for pets or family fun. The 2-car garage includes a convenient garage screen door, sprinkler system and the home also feature gutters for added protection. This home has been lovingly maintained and is truly move-in ready. Don’t miss your opportunity—call today to schedule your private tour! Some of the furniture is available for sale. CALL TODAY FOR A PRIVATE TOUR ON THIS BEAUTIFUL HOME!!!

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

Listing Agent: Gaby Murillo (863-668-1914)

Remarks: Under Construction. The Vale 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 1,758 square feet, 3 bedrooms and 2 and a half bathrooms. Step inside to discover sleek, contemporary design elements complemented by high-end finishes throughout. Entertaining is a breeze, as this townhome features a spacious kitchen island, breakfast nook/dining area and a spacious walk-in pantry. 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. As you enter the foyer you are welcomed with a powder room, and a spacious family room overlooking 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 has 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 an urban lifestyle in a desirable location. *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: Great home with an open living space ready for it's next owner. This home has a fresh coat of paint and is a blank slate for it's new owners. Sit on the front porch and enjoy your morning coffee. The rooms are nice sized with great closet space. The laundry/shop area has plenty of space for your Do-it-yourself projects. Oakwood Estates, a 55+ community offers 2 pools, 2 clubhouses, shuffleboard, tennis courts, miniature golf, and much more. In addition to the amenities, Oakwood offers many opportunities to meet with new folks. Come to Koffee Klatch on Wednesday morning, enjoy an ice cream social a couple times a month, or get your Boogie on at one of the dances. Call today to view this home that's just waiting for YOU!!

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

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