Winter Haven Homes For Sale & Real Estate - 824 homes

Remarks: One or more photo(s) has been virtually staged. Welcome to this charming 3-bedroom, 3-bath home located in one of Winter Haven’s most established and sought-after neighborhoods. Situated on a spacious 0.26-acre lot, this property offers timeless character, mature surroundings, and a location rich in local history. A standout feature of the home is the private suite with its own entrance and full bathroom, ideal for guests, extended family, or a flexible work-from-home space. The layout provides both privacy and functionality, making it a rare find in this area. Recent updates include a newer roof (approx. 1 year old), updated electrical, a new water heater, and a newer A/C unit (2018), offering peace of mind on major systems. Enjoy the unique setting with nearby views of Lake Elbert to the north and Lake Otis to the south, surrounded by well-established homes and nearby lakefront properties. The home offers great bones and classic charm, presenting an excellent opportunity for buyers to update and personalize while investing in a premier location. Conveniently located near downtown Winter Haven, shopping, dining, and more.

Listing is courtesy of: REAL BROKER, LLC (855-450-0442)

Listing Agent: Dave Westphal (863-287-3302)

Remarks: Welcome to this fully upgraded 4-bedroom, 2.5 bath Winter Haven home! This home offers modern living, featuring new flooring, appliances, new windows with pull-out panes for easy access and cleaning along with new Plantation Shutters on all windows! You will also enjoy the stylish bathroom/kitchen renovations featuring in the kitchen beautiful backsplash and new pantry door, new tile in guest bath and new shower in primary bathroom! Centrally located near Legoland, shopping, and all your medical facilities, the property includes a new fenced back yard and new storage shed, HOA/City approved. Sellers are highly motivated!

Listing is courtesy of: STACEY TOWNS REALTY LLC (863-422-1585)

Listing Agent: Cathy Stripling (863-422-1585)

Remarks: DON'T MISS THIS 3 BEDROOM 2.5 BATH HOME CENTRALLY LOCATED IN WINTER HAVEN, FL ON AN OVERSIZED (.39 ACRE) LOT WITH NO HOA!!! Featuring nearly 2,000 SqFt. of heated and cooled living space, this 2-owner home was constructed of BLOCK AND BRICK! The OPEN-CONCEPT, SPLIT BEDROOM PLAN, and CENTRALLY LOCATED KITCHEN share both privacy and convenience. There is plenty of natural light in the main living area and especially through the glass sliders leading to the back yard. In the event more privacy is preferred, just hit the remote button for the MOTORIZED BLINDS, which are also INCLUDED IN THE SALE. For those looking for an OVERSIED GARAGE, this one plenty of workspace for several different hobbies. There is no shortage of parking whatsoever on this HUGE CORNER LOT! Opportunity awaits at this lovely residence, which is located in close proximity to LEGOLAND, FL, medical, shopping, dining, schools, and the many freshwater lakes Winter Haven features. Winter Haven is also located between ORANDO INTERNATIONAL and TAMPA INTERNATIONAL AIRPORT, and the most recently added AVELO AIRLINE in LAKELAND, FL!!!

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

Listing Agent: Wanda Dicks (863-287-7846)

Remarks: Welcome to this beautiful fully renovated 3-bedroom, 2-bath home offering 1,485 square feet of stylish, move-in-ready living in the heart of Winter Haven, Florida. Every detail has been thoughtfully updated to deliver modern comfort and peace of mind. Enjoy brand-new doors and windows that fill the home with natural light, along with a completely new kitchen featuring contemporary finishes and new appliances—perfect for everyday living and entertaining. Both bathrooms have been fully renovated, offering fresh, modern design and functionality. New flooring throughout ties the home together with a clean, cohesive look. Adding even more value, a brand-new roof has been installed, providing long-term durability and confidence for the next homeowner. AC Replaced in 2020, Whole Home re-pipe with PEX and PVC/CPVC in 2020. Conveniently located near shopping, dining, schools, and Winter Haven’s renowned lakes, this turnkey property blends modern upgrades with Florida charm. Don’t miss the opportunity to own a fully updated home ready for immediate enjoyment.

Listing is courtesy of: DOWNTOWN REALTY (407-989-8881)

Listing Agent: Mark Rankin (407-989-8881)

Remarks: One or more photo(s) has been virtually staged. Welcome to this stunning Winston floorplan, located in the highly sought-after community of Willowbrook near a beautiful golf course in Winter Haven, FL. This spacious 5-bedroom, 3-bath home offers 2,531 square feet of living space and provides excellent curb appeal in its elevation. Inside, you'll find gorgeous White cabinets complemented by sleek quartz countertops in the kitchen, creating a modern, bright atmosphere. Tile flooring runs throughout the wet and common areas, offering durability and easy maintenance. The open layout is perfect for family gatherings and entertaining guests.

Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)

Listing Agent: Cindy Sapp (352-516-2843)

Remarks: Perfect BLOCK home for the first time home buyer, investor or seasonal owner - and a prime investment property for consideration as well. Located in a wonderful mature neighborhood zoned as a MIXED USE area; so there is potential to convert this Residential home into an Office or a Business! Offering quick access to every amenity imaginable and close to the Heart of Winter Haven. Currently a 2 bedroom home with a bonus room, could be 3 or 4 bedrooms with conversion of the bonus room and/or the garage. The large lot is between 1/4 & 1/2 Acre size with a fenced backyard. Roofing and electrical was recently updated. A great piece of real estate with lots of opportunity!

Listing is courtesy of: NUWAVE REALTY (386-473-9765)

Listing Agent: Penny Miller (386-473-9765)

Remarks: OPPORTUNITY KNOCKS ON THIS SPACIOUS & AFFORDABLE 3 Bedroom/2 Bath Home in the heart of SE Winter Haven located in Lake Daisy Estates is ready for you & your family!!! NO HOA or CDD in this established neighborhood that is within 3 miles of LEGOLAND and close to multiple restaurants, shopping, & parks. The natural light fills each room of the home. Open floor plan with split bedrooms. You'll love the large open backyard that is fully fenced. Newer roof (2023). Schedule a tour today!!!

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

Listing Agent: Cheryl Brewer (863-224-0045)

Remarks: Under contract-accepting backup offers. Buyer defaulted, check out this great value. The property you are inquiring about is located in Winter Haven, FL, in the Orchid Springs area of East Polk County. This is a 2nd-floor unit in Orchid Springs that is ready to move into NOW! The home has fresh paint throughout and brand new carpet. This is a one-bedroom, open floor plan with most of all utilities bundled in the HOA fees - to include - community pool, gas, exterior maintenance, maintenance grounds, water, sewer, trash. It has an approximate of 1,078 square feet of living, a dedicated parking space, and a common laundry area. Great with overlooking the preserve of nature's own form and the extremely quiet area of the Orchid Springs compound. Text, call, or email for viewing. *Agents, please read MLS remarks.*

Listing is courtesy of: BROKERS REALTY OF CENTRAL FLOR (863-294-6773)

Listing Agent: Renee Butler (863-294-6773)

Remarks: Under contract-accepting backup offers. Property is under contract with contingencies and a kick-out clause. Seller will consider backup offers. Lakefront home on the prestigious Chain of Lakes, directly on Lake Eloise, set on 1.87 acres. This three-story estate offers 6 bedrooms, 5.5 bathrooms, and a private in-law suite on the lower level, providing exceptional privacy, generous scale, and a setting designed to embrace the lake. The primary suite is thoughtfully positioned to capture sweeping lake views and serves as a true retreat, featuring a large walk-in closet and a spa-style bath with oversized shower and jacuzzi tub. Additional living spaces flow effortlessly, anchored by a chef’s kitchen with granite countertops, cherry cabinetry, and double ovens, opening to both formal and casual gathering areas ideal for entertaining. Designed for elevated living and hosting, the home includes a private movie room for a true theater experience and a spacious game and gathering room located just off the pool, creating a seamless indoor-outdoor connection. Outdoor living is a focal point of the property, highlighted by a large infinity pool within a screened enclosure overlooking the lake—an ideal setting for entertaining, relaxing, and enjoying sunset views. A private boat dock extends the lakefront lifestyle. Additional highlights include a grand circular driveway, mature shade trees, a four-car garage with space for recreational vehicles, a whole-home Generac system, and low HOA.

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

Listing Agent: Daniela Zoppe (407-808-7350)

Remarks: Under contract-accepting backup offers. R E D U C E D - R E D U C E D ... DON'T WAIT TO OWN THIS 2BR-2BA MFG HOME ON THIS LARGE CORNER LOT IN SE COMMUNITY WITH LOW MONTHLY FEES, OWNING YOUR OWN LAND AND GREAT AMENITIES. CLUBHOUSE WITH LARGE ENTERTAINMENT ROOM, FULL KITCHEN, LIBRARY, BILLIARDS ROOM, SPA, OVERSIZED POOL OVERLOOKING WATERFRONT PEACE POND WITH COOKOUT ROOM OFF POOL AREA AND EVEN SHUFFLEBOARD, THIS COMMUNITY OFFERS SO MUCH FOR THEIR RESIDENTS. THE HOME IS MOVE IN READY AND HAS SOME FURNITURE LEFT FOR CONVENIENCE OF THE SELLER. OPEN LIVING ROOM DESIGN WITH SEPARATE DINING ROOM, LARGE KITCHEN HAS EAT IN COUNTER , SPLIT BEDROOM PLAN WITH 2 BATHS. PRIMARY BEDROOM AND BATH HAS STEP IN SHOWER AND GUEST BATH OFF 2ND BR HAS TUB. LAUNDRY ROOM WITH WASHER, DRYER & WORKSHOP WALL OFF THE 14X8 SCREEN ENCLOSED PORCH. 18X11 CARPORT WITH LONG DRIVEWAY WITH PLENTY OF PARKING SPACE FOR VISITING GUESTS. MATURE LANDSCAPING WITH 2 LARGE OAKS ON THIS CORNER LOT.

Listing is courtesy of: FLORIDA HOME CHOICE REALTY (863-412-2727)

Listing Agent: Glenda Pruitt (863-412-2727)

Remarks: Tucked away on the golf course in the highly sought after Cypresswood Golf and Country Club community of SE Winter Haven with serene pond views and lush natural foliage for privacy, this beautifully maintained single-family pool home offers the perfect blend of comfort, elegance, and resort-style living. A circular drive sets the tone as you arrive, leading into a thoughtfully designed split-bedroom floorplan ideal for both everyday living and hosting guests. The heart of the home features solid wood cabinetry and rich granite surfaces in the kitchen and baths, combining timeless style with durability. The primary suite is a true retreat, complete with an en suite bathroom and a spacious walk-in closet. Guests will appreciate the dedicated pool/guest bathroom, perfectly positioned for indoor-outdoor living. Step outside to the screen-enclosed pool deck and take in tranquil views of the golf course and pond—your own private oasis framed by mature landscaping. Whether enjoying a quiet morning coffee or entertaining at sunset, this outdoor space delivers year-round enjoyment. Located within a gated community with 24-hour guard service, residents enjoy access to an impressive array of amenities, including a community pool, tennis, pickleball and basketball courts, a clubhouse with restaurant, pro shop, and a fully equipped fitness center. This is more than a home—it’s a lifestyle.Tucked away on the golf course with serene pond views and lush natural foliage for privacy, this beautifully maintained single-family home offers the perfect blend of comfort, elegance, and resort-style living. A circular drive sets the tone as you arrive, leading into a thoughtfully designed split-bedroom floorplan ideal for both everyday living and hosting guests. The heart of the home features solid wood cabinetry and rich granite surfaces in the kitchen and baths, combining timeless style with durability. The primary suite is a true retreat, complete with an en suite bathroom and a spacious walk-in closet. Guests will appreciate the dedicated pool/guest bathroom, perfectly positioned for indoor-outdoor living. Step outside to the screen-enclosed pool deck and take in tranquil views of the golf course and pond—your own private oasis framed by mature landscaping. Whether enjoying a quiet morning coffee or entertaining at sunset, this outdoor space delivers year-round enjoyment. Located within a gated community with 24-hour guard service, residents enjoy access to an impressive array of amenities, including a community pool, tennis, pickleball and basketball courts, a clubhouse with restaurant, pro shop, and a fully equipped fitness center. This is more than a home—it’s a lifestyle. Whether you’re raising a family, welcoming visiting guests, or enjoying a seasonal escape, this home offers the space, setting, and lifestyle to fit every chapter. The Cypresswood community is minutes from Highway 27 and the I-4 corridor, Winter Haven's very own Legoland Florida Resort, the Polk Parkway, and in the center of a thriving community with many convenient grocery, restaurant, shopping, and commuting options for travel in less than an hour from Disney World and other Orlando attractions, the Orlando International Airport, and the gulf-side beaches of Tampa/St. Pete! Schedule your private showing today, and don't miss the opportunity to make this incredible home yours. AGENTS, please see remarks.

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

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

Remarks: Welcome to this meticulously maintained 3-bedroom, 2-bath pool home located in the highly sought-after 24-hour guard-gated Cypresswood Golf and Country Club community of Winter Haven. Thoughtfully designed with a desirable split-bedroom floorplan, this residence offers both privacy and functionality for everyday living and entertaining. Plus, seller is currently in the process of installing a NEW ROOF! Step inside to find beautiful hardwood and tile flooring throughout, creating a warm yet low-maintenance living environment. The spacious primary suite serves as a private retreat, complete with direct access to the screen-enclosed pool deck — perfect for enjoying your morning coffee or an evening swim under the stars. The heart of the home flows seamlessly into a dedicated dining area, with an exciting bonus room just beyond featuring a fun wet bar — ideal for hosting gatherings, game nights, or creating your own lounge space. Two additional bedrooms are situated on the opposite side of the home, providing comfort and privacy for family or guests. Outdoors, the screened pool deck offers the perfect space for relaxing or entertaining year-round. The garage includes a dedicated workshop area, making it ideal for hobbyists, DIY enthusiasts, or extra storage needs. Beyond the home itself, residents enjoy an exceptional lifestyle within this premier community, featuring a championship 18-hole golf course, community pool, fitness center, clubhouse, on-site restaurant, and pro shop. Exciting new amenities are on the way, including lighted tennis courts, pickleball, and basketball courts — offering something for everyone. Whether you’re raising a family, welcoming visiting guests, or enjoying a seasonal escape, this home offers the space, setting, and lifestyle to fit every chapter. The Cypresswood community is minutes from Highway 27 and the I-4 corridor, Winter Haven's very own Legoland Florida Resort, the Polk Parkway, and in the center of a thriving community with many convenient grocery, restaurant, shopping, and commuting options for travel in less than an hour from Disney World and other Orlando attractions, the Orlando and Tampa International Airports, and the gulf-side beaches of Tampa/St. Pete! This is more than just a home — it’s a lifestyle. Schedule your private showing today!

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

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

Remarks: HUGE PRICE DROP! Completely renovated home with new pool on Cannon Lake! Welcome to your dream lakeside retreat on a sprawling lot with 120 feet of pristine lakefront on Lake Cannon. This completely renovated three-bedroom, two-bathroom home boasts an open floor plan with high ceilings and a desirable split-bedroom layout. The stunning kitchen features granite countertops, a counter-height breakfast bar, and brand-new Samsung bespoke appliances, including an induction stove, perfect for culinary enthusiasts. The expansive primary suite offers a luxurious en suite bath with a large shower equipped with multiple showerheads, including a rain showerhead, and sliding glass doors that lead to an impressive outdoor entertaining space. The screened-in patio, perfect for hosting gatherings, overlooks the brand-new saltwater, heated pool and spa, completed in 2025, creating an idyllic setting for relaxation and fun. Additionally, the home features a new roof and new windows, ensuring peace of mind for years to come. Enjoy unobstructed views of the lake from your large outdoor area, ideal for summer barbecues or evening stargazing. Conveniently located near shopping, restaurants, and entertainment, this home truly offers the best of lakeside living on the chain of lakes.

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

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

Remarks: Come to see this move-in-ready, 4-bedroom 2-bath home located in the Beautiful Community of Emily Estates!! Featuring shiny new stainless steel appliances, fresh interior and exterior paint, and brand new plumbing fixtures, this home feels like it was just built! You will love everything about this house, but especially its light and bright floorplan, showering sunlight on the wide open living areas, a kitchen with plenty of cabinet and counter space, and a breakfast bar, ceramic tile throughout for easy maintenance, a beautiful backyard with tons of room to run and play or relax and soak up some sun. Located in a great neighborhood close to shopping, dining, and right down the road from Legoland!

Listing is courtesy of: RE/MAX ACTION FIRST OF FLORIDA (727-531-2006)

Listing Agent: Octavia Cheveresan (727-403-8948)

Remarks: Welcome to maintenance-free living in the heart of Winter Haven! This darling 2-bedroom, 2-bath villa is perfectly located in the desirable Imperial Villas a 55+ residential community, sitting within a short walking distance to beautiful Lake Howard. Inside, you’ll find updated flooring throughout and both bathrooms tastefully renovated, giving the home a fresh, move-in-ready feel. The open layout flows seamlessly to a peaceful sitting lanai overlooking the heated community pool—the perfect spot to enjoy your morning coffee or unwind in the evenings. Major updates add peace of mind, including a resurfaced roof with a 15-year warranty, a tankless hot water heater, and an updated electrical system. The low HOA fee of just $270/month covers water, high-speed internet, cable, gas, and all grounds maintenance—you only pay for electric! The property includes 2 assigned parking spaces, with one under a carport, and the community has ample visitor parking. Enjoy easy access to shopping, dining, and downtown Winter Haven events, all while embracing a relaxed, low-maintenance lifestyle close to the lake. Whether you’re downsizing, snowbirding, or looking for carefree Florida living, this villa checks all the boxes. Property is eligible for FHA Financing! Move in, relax, and enjoy the best of Winter Haven living!

Listing is courtesy of: DALTON WADE INC (888-668-8283)

Listing Agent: Michele Elchin (863-514-6880)

Remarks: Hidden gem with upgrades you won’t expect! First-floor condo for easy access and numerous updates throughout. The kitchen features a new backsplash, new sink and faucet, freshly painted cabinets, and newer appliances, including the refrigerator and dishwasher. A new water heater adds additional peace of mind. Both bathrooms have been updated with new vanities, faucets, and tile backsplashes. Custom wood shelving has been installed throughout the home—no wire shelving—along with custom closet organizers in both bedrooms. The spacious primary bedroom features beautiful plantation shutters. Stylish barn doors enclose the laundry area with a washer and dryer, and the hall closet. Covered parking included. Situated on scenic Lake Howard, part of the famous Winter Haven Chain of Lakes, this community offers boat dock access. Residents also enjoy a sparkling pool, gazebo with grilling area, shuffleboard courts, and a quiet, secure atmosphere. Even better, the HOA covers cable, internet, water, sewer, trash, exterior maintenance, and lawn care—you only pay for electricity. Truly affordable, maintenance-free Florida living.

Listing is courtesy of: VILLAGE REALTY OF WINTER HAVEN (863-299-6767)

Listing Agent: Nancy Cini (727-612-0375)

Remarks: One or more photo(s) has been virtually staged. This 3 bedroom, 2 bathroom home is located in Idylwild Heights a charming residential subdivision nestled in Winter Haven, Florida. Winter Haven is a picturesque city celebrated for its chain of lakes and friendly community atmosphere. Known for its welcoming ambiance and established neighborhood feel, Idylwild Heights offers residents an appealing blend of suburban tranquility and convenient urban access.

Listing is courtesy of: CENTURY 21 WOLF'S CROSSING REALTY (407-449-0000)

Listing Agent: Lucy Martinez (863-521-4156)

Remarks: Under contract-accepting backup offers. Beautiful 4-bedroom, 2-bath home in Magnolia Preserve with an open-concept layout, high ceilings, and a large backyard overlooking a pond with a fountain. The spacious great room features wood-look flooring, recessed lighting, and a ceiling fan, while the kitchen offers a large breakfast bar, ample cabinetry, stainless steel appliances, and generous counter space. The primary suite includes a walk-in closet and an en-suite bath with dual sinks, garden tub, and separate shower. Enjoy the covered rear patio, interior laundry room, and 2-car garage. Move-in ready and conveniently located near shopping, dining, and major roadways.

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

Listing Agent: Jeremy Harper, Pa (863-288-0886)

Remarks: This move-in-ready, three-bedroom, two-bathroom home is located in the sought-after Lake Dexter Woods community. The residence features a functional layout designed for modern comfort and style, highlighted by an attached one-car garage and low-maintenance tile flooring throughout the entire home. The updated kitchen serves as a stylish centerpiece, equipped with beautiful granite countertops and sleek stainless-steel appliances. Outside, you can relax and enjoy the fresh air from your private porch and patio, which overlooks a fully fenced-in backyard, providing a secure space for outdoor entertaining or pets. The location offers a perfect blend of comfort and convenience, situated near top-rated schools, multiple grocery stores, and popular local attractions. Residents can enjoy a resort-style lifestyle with access to premium community amenities, including sparkling pools, tennis/pickleball courts, and more.

Listing is courtesy of: ENTERA REALTY LLC (888-216-6364)

Listing Agent: Robert Salmons (888-216-6364)

Remarks: Under contract-accepting backup offers. Back on market, buyer financing fell through. Their loss, your gain! Stunning ranch modern transformation that will take your breath away! Welcome to this 2019 impeccably redesigned modern rustic 4 bed/2 bath retreat on fenced one-third acre lot on cul-de-sac with seamless indoor-outdoor entertaining. Homeownership pride from the front curb to the back fence! As you approach, you are greeted by a New sprawling 13’x46’ covered front porch with ample space for hosting gatherings while you enjoy the beautifully landscaped front yard with extended driveway that includes a tall RV cover. Step inside to the farmhouse chic living room that seamlessly flows through the sliding barn doors into the heart of the home, the custom designed kitchen, featuring wood beam tray ceiling with pendent lighting, white cabinets, butcher block counter, SS appliances including smart fridge w/tv & Alexa, large island with farm sink and breakfast bar, & barn door pantry with luxury vinyl plank flooring throughout and fresh interior paint. Adjacent to the kitchen on one side is the laundry room with built in cabinets that leads to the back yard, and the other side to the spacious family room, with every inch thoughtfully styled that create a warm, inviting atmosphere. Included is the entertainment center with the wide screen tv. The main bedroom has spacious on-suite bathroom that features beadboard panels & stone backsplash, dark matching accent trim, double sinks, garden tub, separate rain head shower with glass sliding door, and storage closet. The 2, 3 ,& 4th bedroom share a convenient 2nd bathroom with shower/tub. The property also includes a large storage shed with electric— perfect for tools, hobbies, or extra storage. Situated in a peaceful area of Winter Haven, this home offers the best of both worlds: quiet suburban living with easy access to shopping, dining, and major highways for commuting throughout Central Florida. Don’t miss your chance to own this move-in-ready home with modern updates, generous space, and outdoor charm — all with no HOA!

Listing is courtesy of: KELLER WILLIAMS HERITAGE REALTY (407-862-9700)

Listing Agent: Sheryl Manche (386-882-2121)