Winter Haven Homes For Sale & Real Estate - 908 homes

Remarks: This beautifully updated move-in-ready 2/2 home sits in a quiet, established community on Lake Dexter, one of Winter Haven’s pristine spring-fed lakes. The neighborhood offers an exceptional lifestyle with private access to a residents-only boat ramp, a sparkling saltwater community pool, and a serene waterfront park complete with a fishing dock, gazebo, playground, and shady green space to enjoy year-round. It’s a rare setting—peaceful, well-maintained, and so close to everything that you can even walk to Legoland. Inside, the home feels bright, airy, and inviting, thanks to thoughtful updates and fresh finishes throughout. The layout is comfortable and functional, featuring a spacious primary suite, two additional bedrooms, and two full bathrooms. The third office or bedroom sits just off the kitchen and is framed by French doors, making it the perfect space for a home office, guest room, or flex space to fit your lifestyle. The seller has invested in quality improvements, including a brand-new roof, fresh interior and exterior paint, a new electric water heater, a full water-softening system, updated light fixtures and hardware, refreshed landscaping, a newly rescreened back patio, and recent servicing of both the AC and irrigation systems. The main living areas feature attractive luxury laminate flooring, adding warmth and style, while the screened back porch provides a quiet, private place to relax overlooking the neatly manicured yard. Winter Haven’s central location between Tampa and Orlando puts major attractions, beaches, airports, and dining just a short drive away, making this an ideal full-time residence or a low-maintenance Florida getaway. This charming home truly checks all the boxes for comfort, convenience, and easy Florida living. All measurements are approximate and should be verified by the buyer or buyer’s agent.

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

Listing Agent: Emily Ward (863-632-1865)

Remarks: Your Florida Dream Home Awaits in Lake Ashton, an exclusive gated 55+ community. A golf membership (expires Sept. 30, 2026) for a single golfer will convey. Discover this beautiful 3 bedroom, 2 bathroom Sebastian Floor Plan home with an oversized backyard with pond and trees beyond. This PET FREE home is perfectly positioned; one home removed from a cul-de-sac. With over 2,045 sq. ft. living area, this home offers great curb appeal with a well maintained lawn, gutters, paver driveway & walkway, poured curbing around landscaped areas & separate golf cart garage entry. You'll love the screened entry at the front door with side lights and eyebrow window above. With a spacious open floor plan, this bright and airy home is designed for both comfortable living and seamless entertaining with the kitchen overlooking the living room and dining room areas with tile flooring and trey ceiling. Built in 2017 this desirable home has SS Appliances, Under Cabinet Lighting, Breakfast bar, 42" cabinets, Walk In Pantry and generous Granite counter space in the kitchen, making it a chefs delight. Bedroom 2 & 3 are located to the right of the front door just off of the front entrance of the home. Bedroom 2 with carpet, built in closet and Bay window is on the front of the home. Bedroom 3 with tile plank flooring, built in desk with cabinets above and two side closets could be used as a sitting room, craft room or additional tv room for guests. - You choose. The Guest Bathroom separates BR 2 and BR 3. Guests will love the walk in shower with glass enclosure, comfort height vanity and accent glass block above. A linen closet is in the hallway that separates BR 2 and BR 3. The living room has triple glass sliding doors that open to the covered and screened lanai. You'll love the water and nature views from the LR, Dinette and Primary Suite. This well-maintained home with newly cleaned windows has a central vacuum system, too! The Primary Suite is located on the back of the home directly off the Living Room. The En- Suite offers a large walk in closet, separate water closet with window, His and Her Comfort Height Vanities and Large corner Walk In Shower with tiled corner seat/footrest, accent glass block above and a door separates the Primary Bath and Primary Bedroom. Unwind after a long day of having FUN on the screened, covered Lanai with one acrylic window wall. Place your grill on the paver pad just outside of the lanai and take in the tranquil surroundings of your oversized backyard with seasonal pond and trees beyond. The SOLAR PANELS on this home will provide additional monthly savings to YOU. The washer/dryer in the spacious laundry room will convey with the sale of the home. The laundry room has a wash sink, additional cabinets (upper and lower), a seat so you can put on your shoes with ease and a shoe organizer. The garage floor has an epoxy coating and an automatic screen is on the double car garage. Residents in Lake Ashton enjoy the main clubhouse with outdoor pool, bocce, movie theater, card, craft, billiards, bowling lanes, media room, fitness center and grand ballroom. Residents also enjoy the Health and Fitness Center with indoor pool, indoor basketball, indoor racquetball, card, craft and billiards, pickle ball, tennis courts and MORE. Golf Memberships are optional. 2 18-hole golf courses are located within Lake Ashton. Restaurants, Entertainment, Shopping and Medical Facilities are just a short distance away. You MUST See this home!

Listing is courtesy of: LAKE ASHTON REALTY INC. (863-221-5970)

Listing Agent: Lori Raath (863-409-6899)

Remarks: CALLING ALL INVESTORS!! Amazing opportunity with a blank canvas to be creative! This property boasts 2 separate dwellings, both with living spaces, kitchens, dining areas, 2 bedrooms and 1 bathroom WITH an in ground pool in between! Property also has a THREE car garage AND a huge open space in the attic with stair access from a bedroom! Direct view and access to Lake Cannon, WOW!! Make your appointment today to secure this amazing opportunity! CASH ONLY, BEING SOLD AS IS.

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

Listing Agent: Veronica Davis (863-326-8001)

Remarks: Welcome to your dream home in the gated community of Ruby Lake! This beautifully designed 3-bedroom, 2-bath Cassidy “Ox” floor plan perfectly balances elegance and everyday comfort. Step inside to discover a spacious layout featuring formal living and dining rooms, along with a generous family room—ideal for both entertaining and relaxed living. The updated kitchen is truly the heart of the home, showcasing sleek quartz countertops, a breakfast bar, closet pantry, and durable tile flooring. Retreat to the impressive primary suite, offering a large 17x15 bedroom, walk-in closet, and a spa-like en suite bath complete with soaking tub, walk-in shower, and dual vanities. Thoughtfully designed, the secondary bedroom and bath are handicap accessible with widened doorways for added ease. Enjoy Florida living year-round on the expansive 10x38 screened lanai—perfect for gatherings or quiet evenings. Additional highlights include an interior laundry room with sink, surround sound throughout, plantation shelving with ambient lighting, ceiling fans, irrigation system with separate meter, and a 2-car garage with a high-profile door. Conveniently located near shopping, dining, medical facilities, schools, and Legoland, with easy access to Tampa and Orlando—this exceptional home truly has it all. Don’t miss your opportunity to make it yours!

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

Listing Agent: Steve Lockhart (863-289-9801)

Remarks: Over a half-acre fenced in lot with a 4 bedroom 2 1/2 bath home with an office or den. Large family room with a separate formal dining room. Eat in kitchen with 2 pantry's. New roof in 2017-2018 and a new air conditioner in 2019. Great location minutes from State Road 60 and close to all the dining and theme parks and spring baseball field in Winter Haven.

Listing is courtesy of: BROOKS REALTY GROUP LLC (813-653-7291)

Listing Agent: Erica Ranson (863-934-3510)

Remarks: Welcome to 720 Overlook Grove Dr in beautiful Winter Haven! This move-in ready home has just received a fresh interior and exterior paint update, giving it a clean, modern feel throughout. Enjoy peace of mind with a new roof (2023) and numerous upgrades that make this property truly stand out. The updated kitchen features modern finishes, refreshed cabinetry, and upgraded countertops—perfect for everyday living and entertaining alike. Natural light fills the living spaces, creating a warm and inviting atmosphere. Situated on a large lot within the subdivision, the property offers plenty of outdoor space and is completely fenced in for added privacy—ideal for pets, gatherings, or simply relaxing outdoors. Step outside to your patio lanai, the perfect spot for morning coffee or evening unwinding. Located in a rapidly growing area, this community is seeing exciting expansion with new construction homes and grocery stores being built nearby, adding convenience and future value. With easy access to shopping, dining, and major roadways, this home offers the perfect blend of comfort, updates, and prime location. Don’t miss your opportunity to own this beautifully updated property!

Listing is courtesy of: LOKATION (954-545-5583)

Listing Agent: Jenny Nguyen (407-202-2640)

Remarks: EXCELLENT INVESTMENT OPPORTUNITY IN THE HEART OF WINTER HAVEN! LOCATED AT 601 AVE U NE, THIS PROPERTY OFFERS INCREDIBLE POTENTIAL FOR RENTAL INCOME OR FUTURE DEVELOPMENT. WITH A SPACIOUS LOT AND SOLID STRUCTURE, IT'S PERFECT FOR INVESTORS LOOKING TO RENOVATE, RENT, OR FLIP. CONVENIENTLY SITUATED NEAR DOWNTOWN WINTER HAVEN, SCHOOLS, SHOPPING, AND MEDICAL FACILITIES, THIS LOCATION IS IDEAL FOR LONG-TERM TENANTS OR RESALE VALUE. BENEATH THE EXISTING CARPETING, YOU WILL FIND WELL-PRESERVED HARDWOOD FLOORING READY TO BE DISCOVERED AND ENJOYED. DO NOT MISS YOUR CHANCE TO OWN A PIECE OF RAPIDLY GROWING WINTER HAVEN-OPPORTUNITIES LIKE THIS DO NOT LAST LONG!

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

Listing Agent: Brian Reeves (877-366-2213)

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

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

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

Remarks: Under contract-accepting backup offers. Property is tenant/owner occupied. Strictly by appointment only with at least 24-hour notice. To schedule a showing, please text the Listing Agent with your name, brokerage, and requested time. Please do not disturb the occupants. Thank you for showing!"

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

Listing Agent: Abigail Gomez (863-288-4055)

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: 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: 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)