Winter Haven Homes For Sale & Real Estate - 1041 homes

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

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

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

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

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

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

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

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

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

Remarks: Welcome home to Brenton Manor! This move-in ready 3-bedroom, 2-bathroom split-plan home checks every box — and then some. The open-concept kitchen flows seamlessly into the great room, creating the perfect space for entertaining or relaxing after a long day. Step outside to your private, fully fenced backyard with no rear neighbors — your own Florida oasis. Big-ticket updates have already been done for you: brand-new 2026 HVAC with UV ray lights and professionally cleaned ductwork, 2026 whole-home water softener system, 2025 tankless water heater, 2025 fresh exterior paint, 2025 gutters, and a 2023 roof. Both bathrooms feature updated showers, so all you need to do is move in and enjoy. Conveniently located near top medical facilities, BayCare Winter Haven Hospital just minutes away, and the nationally recognized Lakeland Regional Health nearby. Everyday conveniences are just as close, with shopping, dining, and retail options all within a short drive. Ideally located for commuters and travelers, this community offers. Ideally located for commuters and travelers, this community offers quick access to Interstate 4, the Polk Parkway (SR-570), and US-27—placing Tampa and Orlando approximately 30 to 40 minutes away and the world-famous theme parks just 35 miles away. Schedule your private showing today!

Listing is courtesy of: COLDWELL BANKER REALTY (407-696-8000)

Listing Agent: Cynthia Davis (407-619-2937)

Remarks: Fully Occupied Income Property | 3 Units | $4,300/mo Gross Rent | No Vacancy | Winter Haven Rare turnkey income property generating $4,300/month in gross rent — fully occupied with zero vacancy. This versatile multi-income single-family property features two interior apartments plus a separate rear cabin, each independently rented with established tenants in place. Landlord expenses are minimal: owner covers water (~$25/mo) and basic WiFi ($50/mo). Tenants handle electricity, lawn maintenance, and all other utilities — maximizing net cash flow from day one. 4 bedrooms | 2 bathrooms | 1,680 sq ft | Built 1965 | Polk County | Minutes from US-27, downtown Winter Haven, and Legoland Florida. Ideal for the buy-and-hold investor seeking immediate cash flow with low management overhead. Current leases transfer at closing. All financing welcome: Conventional | DSCR Loan | Cash.

Listing is courtesy of: CAISSA REALTY INVESTMENT INC (407-364-3056)

Listing Agent: Elizabeth Rodriguez (407-480-8829)

Remarks: Welcome to this stunning 4-bedroom, 2-bath home located in a vibrant and growing neighborhood. Built in 2020, this modern residence offers the perfect blend of style, comfort, and functionality—ideal for today’s lifestyle. Step inside to discover a bright and spacious open-concept floor plan, perfect for both everyday living and entertaining. The gourmet kitchen is a true centerpiece, featuring rich espresso cabinetry, gleaming granite countertops, stainless-steel appliances, and a massive center island with sink—ideal for hosting gatherings or preparing family meals. Retreat to the primary suite, complete with a generous walk-in closet, dual vanities and a walk-in shower. Three additional bedrooms provide ample space for family, guests, or a home office. Enjoy Florida living at its best on the covered patio, overlooking a large, fully fenced backyard—perfect for summer barbecues, pets, play, and relaxing evenings under the stars. With modern finishes, thoughtful design, and move-in-ready condition, this home is a must-see. Don’t miss your opportunity to own this exceptional property—schedule your private showing today!

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

Listing Agent: Humberto Cuevas (407-725-9971)

Remarks: Don’t miss this incredible opportunity to own a villa in one of Winter Haven’s most sought-after gated golf communities — at an unbeatable price! This 2-bedroom, 2-bathroom villa offers 1,278 sq ft of comfortable Florida living with a peaceful pond view backdrop. The open floor plan flows effortlessly, and the private enclosed Florida room is perfect for year-round entertaining. The generous primary suite features a walk-in shower, and the guest bath includes a tub/shower combo. Why this is a steal: Priced well below comparable properties in the community, Resort-style amenities INCLUDED — 18-hole golf course, tennis, pickleball, pool, fitness center, clubhouse & restaurant, 24-hour manned gate for peace of mind, Pets welcome, Flexible for investors — 6-month minimum lease allowed. Whether you’re looking for your Florida dream home, a seasonal getaway, or a smart rental investment, this property checks every box at a price that won’t last long. Act fast — opportunities like this don’t stay on the market!

Listing is courtesy of: HUMAN TOUCH REAL ESTATE FIRM (863-651-8236)

Listing Agent: Susan Human (863-651-8236)

Remarks: Under contract-accepting backup offers. Short Sale. MAKE AN OFFER ON This better than new construction stunning 4-bedroom, 3-bathroom home is just 2 years young and beautifully maintained—ready for you to move right in! Step into a bright and spacious open-concept layout featuring luxury vinyl flooring throughout, soaring high ceilings, and a seamless flow between the living room and kitchen. The kitchen boasts elegant cabinetry, sleek countertops, and modern finishes. Energy-efficient solar panels help keep utility costs low, and the property is fully enclosed with a new vinyl fence for added privacy. The master suite offers a spacious walk-in closet and a spa-like bathroom complete with an extended walk-in shower, dual sink vanity, and a dedicated towel closet. A second bedroom features its own private ensuite, while a third full bathroom is ideal for guests or inlaws. Relax in your fenced in back patio and enjoy the peace and privacy of your surroundings. Conveniently located near shopping where more stores are being built like a new Target, dining, hospitals, schools and top Central Florida attractions—Legoland is 15 minutes away--this home has it all and more. Don’t miss the opportunity to make it yours!

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

Listing Agent: Marisol Rivera (407-607-5201)

Remarks: Welcome to SPRING LAKE TOWERS, a premier 55+ community in Winter Haven, Florida offering a relaxed lakefront lifestyle with this well-maintained 2-bedroom, 2-bath condo featuring an open floor plan with stunning lake views, a 12' x 22' great room connected to the kitchen via convenient pass-through, spacious 12' x 18' Primary suite with private bathroom and walk-in closet, 10' x 13' second bedroom adjacent to guest bathroom with tub/shower, and a versatile 7' x 23' Florida room perfect for home office, hobbies, or relaxation. The all-inclusive condo fee covers cable TV, internet, water, sewer, trash removal, building maintenance (exterior, roof, insurance), reserve funds, common area upkeep, on-site management, and access to all community amenities including swimming pool, exercise room, recreation room with kitchen, library, game area, shuffleboard, laundry facilities, and active social calendar with enhanced security features. Situated on the "Chain of Lakes" for fishing, boating, and water activities with boat slips available for a reasonable fee (verify with management), this property boasts a rare assigned covered parking space in close proximity to the unit and is adjacent to Northgate shopping plaza featuring Publix, restaurants, and services, minutes from medical facilities, Winter Haven Hospital, places of worship, and downtown. No pets or smoking permitted. This perfect full-time residence or seasonal retreat (measurements approximate, information believed accurate but not guaranteed).

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

Listing Agent: Kevin Tison (863-206-5755)

Remarks: SPACIOUS & AFFORDALE IN SOUTHEAST WINTER HAVEN, THIS 3BR/2BATH home features newer vinyl plank flooring throughout, brand new dishwasher just installed and newer kitchen cabinets! The great room has beautiful dark beams on the ceiling that give the room so much more character. Sliding glass doors open to the 10x23 screened-in patio and partially fenced & spacious rear yard for pets. Adjacent to the kitchen is an extra room, could be great for an office/den space for those who work from home. On the other side of the living area, you'll find 3 bedrooms and a guest bath with tub/shower. The primary bedroom has a walk-in closet with an en-suite bath with walk-in tiled shower. There is an oversized 1-car garage with workshop area and plenty of shelving. Located near the Lake Ned public boat ramp with kid's playground & basketball court! Great location with quick in-town access!!

Listing is courtesy of: THE K TEAM REAL ESTATE SERVICES LLC (863-604-1601)

Listing Agent: Cathy Kluytenaar (863-604-6220)

Remarks: Short Sale. Bank approved price! Welcome to this beautifully updated 4-bedroom, 1.5-bath single-family home located in Winter Haven with NO HOA! This solid block construction home offers peace of mind with a new roof and AC installed in 2024. Inside, you’ll find newer flooring throughout along with a recently renovated kitchen and bathrooms, giving the home a fresh, modern feel. The kitchen features quartz countertops, stainless steel appliances, and updated cabinetry, perfect for both everyday living and entertaining. The functional layout includes four spacious bedrooms, a full bathroom, and an additional half bath for added convenience. Enjoy outdoor living in the fully fenced backyard, ideal for pets, gatherings, or simply relaxing in your private space. The home also includes a 1-car garage for storage and parking. Ideally situated near Lake Conine, part of Winter Haven’s famous Chain of Lakes, this property offers easy access to boating, fishing, and outdoor recreation. Conveniently located near major roadways, providing a quick commute to Orlando, Tampa, and world-renowned attractions like Disney. This move-in ready home combines modern updates, a great location, and no HOA restrictions—don’t miss your opportunity to make it yours!

Listing is courtesy of: KELLER WILLIAMS REALTY SMART (863-577-1234)

Listing Agent: Garrett Robinson (863-838-5210)

Remarks: ENJOY THIS WELL KEPT FURNISHED MANUFACTURED HOME IN GATED 55 AND OVER COMMUNITY. THIS PROPERTY IS IN A CO-OP. OUTSIDE OF HOME RECENTLY PAINTED 2026. THE AIR CONDITIONER IS NEW IN 2025. KING AND QUEEN SIZE BEDS WITH MATCHING DRESSERS, SOFA BED, 70 IN TV, LEATHER COUCH AND ROCKING RECLINERS. SUN ROOM HAS TV WITH LARGE BAR WITH STOOLS. LAMINATE FLOORS IN ALL ROOMS EXCEPT BEDROOMS HAVE CARPET. BRING YOUR TOOTHBRUSH, EVERYTHING ELSE IS READY FOR YOU TO MOVE IN. ENJOY SCHEDULED ACTIVITIES COMMUNITY HEATED POOL, LIBRARY, SHUFFLEBOARD, HORSESHOES, BILLIARDS, AND MORE. TRAILER STORAGE AREA AND LAUNDRY. SELF CONTAINED WATER AND SEWER SYSTEM WITH BACKUP GENERATORS. NO PETS EXCEPT SERVICE ANIMALS. NO MOTORCYCLES. THE $11,000 SHARE IS INCLUDED IN SALES PRICE. LAKE HENRY IS AN 810 ACRE PRIVATE LAKE.

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

Listing Agent: Jean Murphy (863-412-8751)

Remarks: Under Construction. New construction home with 1715 square feet on one-story including 4 bedrooms, 2 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, a tiled shower, and a closeted toilet. 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 décor do not convey!

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

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

Remarks: Under contract-accepting backup offers. Fall in love with this expansive 5-bedroom, 3-bath, 3-car garage home situated on a quarter-acre of land, where luxury, functionality, and energy efficiency come together. Explore every corner of this stunning property right now through a 3D interactive walkthrough or a full video tour. Designed with an open layout and split bedrooms for privacy, the home feels massive yet efficient. The heart of the home is a wide-open living area and a huge kitchen featuring a gigantic island, 42-inch upper cabinets, a spacious pantry, and top-of-the-line stainless steel appliances. Whether you are relaxing, hosting, or cooking, the home provides boundless space to move and mingle. High-quality finishes are found throughout, including granite countertops in the bathrooms, luxury vinyl plank flooring in the main areas, and premium carpeting in the bedrooms. This isn't just a home; it’s an investment featuring $30,000 in upgrades available for your review! One of the standout benefits of this property is the incredible energy efficiency. Powered by solar panels plus a solar-powered attic fan, the home’s energy costs are cut in half compared to neighboring homes that have much smaller living areas. The solar panel lease is a manageable $180 a month, which keeps the actual electric bill payable to TECO energy as low as $5 to $20 a month. For added convenience, the home also includes a paid security system and a water softener system paired with reverse osmosis in the kitchen. The outdoor space is just as impressive, featuring a large, private backyard on a quarter-acre lot fully enclosed by a vinyl fence. You can enjoy the Florida weather from the comfort of a huge, screened-in lanai, surrounded by custom pavers that wrap seamlessly around the sides and back of the home. The meticulous landscaping is easily maintained by a full irrigation system. Located in a quiet, peaceful community in Polk County, you are perfectly positioned near Highway 27 for an easy drive to Disney and the Orlando Airport. Best of all, there are no CDD fees and a low HOA of only $725 a year. This home is being sold AS IS and is ready for you to move in. Schedule your showing today!

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

Listing Agent: Mary Sorrell (765-434-1802)

Remarks: Under Construction. Brand new, energy-efficient home available by Feb 2026! Prepare dinner while catching up on the days events from this home's open kitchen which overlooks a spacious great room and dining area. Retreat to your primary suite that is conveniently situated in the back of the home for plenty of privacy. 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: Welcome to your next home in the heart of Winter Haven! Located on a peaceful cul-de-sac, this charming property at 1210 Zambrana Ct offers the perfect blend of comfort, space, and convenience. Featuring a bright and open layout, this home is designed for both relaxing and entertaining. Enjoy spacious living areas filled with natural light, a functional kitchen with plenty of storage, and well-sized bedrooms that provide comfort for the whole family. The outdoor space offers the perfect setting to unwind or host gatherings, while the location places you just minutes from shopping, dining, and everyday essentials. Whether you're looking for your primary residence or a great investment opportunity, this home checks all the boxes.

Listing is courtesy of: PAK HOME REALTY (909-351-5105)

Listing Agent: Ivanna Mendoza Heredia (417-335-1572)

Remarks: Under contract-accepting backup offers. SPLISH SPLASH--THE SOUND OF SUMMER--WELCOME TO 3407 FOX RIDGE ST WINTER HAVEN FL--THREE BEDROOM TWO BATH POOL HOME IS WAITING FOR NEW OWNER-- MANY UPGRADES IN 2025 INCLUDE NEW KITCHEN CABINETS,NEW KITCHEN COUNTER TOPS, NEW APPLIANCES, NEW AC SYSTEM, NEW POOL MARCITE, NEW POOL SYSTEM, NEW BLINDS AND CEILING FANS, NEW PAINT INSIDE AND OUT. THE NEW UPGRADES FOR 2026 INCLUDE NEW ROOF AND NEW GAS HOT WATER HEATER. THIS HOME IS MOVE IN READY SO DONT HESITATE TAKE THE PLONGE AND MAKE APPOINTMENT TO SEE TODAY---CONVENIENT TO SHOPPING AND LEGO LAND

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

Listing Agent: Esther Skipper (863-712-7632)

Remarks: Short Sale. $50,000 PRICE REDUCTION! Welcome to your perfect retreat in this exclusive gated community, where tranquility meets convenience! Enjoy easy access to shopping, dining, and the exciting attractions of Winter Haven, including Legoland Theme Park, all just minutes away. This charming three-bedroom, two-bathroom home features a modern open-concept layout and a split bedroom design for added privacy. You'll love the luxury vinyl flooring throughout the living areas, with cozy carpet in the bedrooms. Step outside to your large, fully fenced backyard—perfect for relaxation without any rear neighbors. Unwind in your spacious screened-in lanai, ideal for enjoying the outdoors year-round! Additional highlights include an 8 x 5 fireproof storage closet in the garage, providing peace of mind for your valuables, as well as a well-maintained irrigation system and beautiful landscaping that enhances the curb appeal. With quick access to the Polk Parkway and Interstate 4, Central Florida adventures are at your fingertips. Don’t miss out on this fantastic opportunity—schedule your showing today!

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

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

Remarks: Short Sale. Short Sale. Looking for a nice home with amazing potential and opportunity to gain equity? This one may be IT for you! Welcome to this 3-bedroom, 2-bath move-in ready home located in the peaceful and sought-after SE Winter Haven area! Situated on an OVERSIZED corner lot, this home features a fully fenced backyard, high ceilings, and ceramic tile flooring throughout the main living spaces. You’ll love the screened-in lanai and Private Pool—perfect for relaxing or entertaining year-round. The kitchen boasts custom cabinetry, a cozy dinette with wraparound windows, and direct access to an oversized garage. The spacious master bedroom features a walk-in closet, while the additional bedrooms are ideal for family or guests. This home has AMAZING POTENTIAL and nestled in a quiet, well-kept neighborhood, just minutes from Legoland and all of Central Florida’s top attractions. Call today to schedule your private showing—this home is priced to sell and won’t last long!

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

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

Remarks: Spacious Single-Story Block Home with Endless Potential! Nestled in a quiet, established neighborhood close to Polk State College with no HOA, this solid single-story block home immediately catches the eye with its charming blend of stucco and natural multi-colored stone accents. Boasting 1,678 square feet of comfortable living space (2,527 square feet total), the interior features a generously sized layout including three spacious bedrooms and two bathrooms. The primary suite is a true retreat, complete with a walk-in closet for ample storage. At the heart of the home, a large kitchen and dining area provides the perfect setup for family gatherings and entertaining. Step outside onto the oversized 0.26-acre lot, where the backyard offers a private oasis featuring mature, producing fruit trees, a handy detached storage shed, and a solid privacy fence running across the rear property line. Perfectly situated in a desirable community zoned for great local schools, this property has incredible bones and just needs some updating and TLC to truly shine. The seller is highly motivated and ready to see your offers—bring your design ideas and schedule your private showing today to unlock this home's immense potential!

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

Listing Agent: Twanna Dewdney (863-207-1634)