Winter Haven Homes For Sale & Real Estate - 829 homes

Remarks: One or more photo(s) has been virtually staged. Under Construction. BELOW MARKET INTEREST RATES with use of Seller's Preferred Lender. Check out the Indigo, a spacious two-story, 5-bedroom, 3-bathroom, 2-car garage home perfect for growing families or hosting guests. Enter the impressive foyer with soaring ceilings that creates an immediate sense of openness. From the foyer, the home effortlessly flows into the main living areas and kitchen. With quartz countertops throughout, stainless-steel appliances and a smart thermostat for energy efficient climate control, the Indigo brings all the things that matter together. The downstairs guest suite and bathroom are tucked away for added seclusion, while the open concept living space is perfect for entertaining. Upstairs, you'll find a generously sized recreation space, ideal for family time or unwinding. The owner's suite is a true sanctuary, featuring a walk-in shower, double vanities, and a spacious walk-in closet. A laundry room with a new washer and dryer is just off the owner’s suite, conveniently located near the 3 additional bedrooms and full bathroom. The Indigo is as functional as it is stylish, providing the perfect balance of comfort and modern living. Just off US-27 with quick access to I-17, Villa Mar puts you close to local hotspots, and everything that makes Central Florida shine. Discover Winter Haven’s Chain of Lakes, explore the historic downtown district, or enjoy a fun-filled day with the family at LEGOLAND® Florida Resort. At Villa Mar, you’ll enjoy a fresh approach to relaxed living, with everyday essentials and local favorites right around the corner. Images shown are for illustrative purposes only and may differ from actual home. Completion date subject to change. Contact or make an appointment for more details on interest rates.

Listing is courtesy of: CASA FRESCA REALTY (813-343-4383)

Listing Agent: Michael Human (813-343-4383)

Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Welcome home to this beautifully maintained move-in ready 3-bedroom, 2-bathroom home with a screened-in porch located in Winter Haven, Florida. As you step inside, you are greeted by elegant French doors and a stunning bay window that fills the living room with an abundance of natural light. The primary suite is privately located on one side of the home and offers its own en-suite bathroom and walk in closet, creating a peaceful retreat at the end of the day. On the opposite side of the home, you will find two additional bedrooms and a second full bathroom. The kitchen features a practical layout and opens to the dining room, creating a comfortable space for daily living and hosting guests. An interior laundry closet adds convenience and makes household tasks simple and accessible. Step outside to enjoy the spacious screened-in back porch, ideal for relaxing or hosting family gatherings. The fully fenced backyard and additional side patio offers a great space for grilling and spending time with friends and loved ones. A one car garage provides secure parking along with additional storage space. This home is conveniently located in the Whisper Lake Community off Highway 17 with quick access to the Polk Parkway, making commutes to Orlando and Tampa simple and efficient. Located just minutes from LEGOLAND Florida Resort, as well as shopping, dining, and everyday amenities. The 3rd bedroom is currently not fully enclosed, but can easily be completed to create a fully private third bedroom, home office, or flex space. It is currently left open behind the dinning room to create a larger space. This delightful home is ready for you, schedule your private showing today.

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

Listing Agent: Ashley Lopez (863-585-0585)

Remarks: Under contract-accepting backup offers. ***More Pictures Coming Soon*** Experience refined living in the heart of Downtown Winter Haven with this architecturally significant residence just moments from the city’s vibrant lakeside lifestyle. Perfectly positioned within walking distance of local restaurants, boutiques, parks, and entertainment, this exceptional residence places you at the center of one of Central Florida’s most charming downtown districts. Residents will also enjoy quick access to LEGOLAND® Florida Resort, the renowned Chain of Lakes, and nearby tennis and recreation facilities. Originally designed by celebrated architect Gene Leedy, a pioneer of the Sarasota School of Architecture, this residence showcases the timeless elegance of Florida modernism. Clean architectural lines, open living spaces, and distinctive exposed concrete elements reflect Leedy’s philosophy of blending structural beauty with functional design. Expansive interiors allow natural light to flow throughout the home, creating a seamless connection between indoor comfort and the surrounding Florida landscape. Inside, the thoughtfully designed floor plan offers 2 spacious bedrooms, 2 full bathrooms, and a convenient half bath, with 1,408 square feet of living space that balances openness with privacy. The residence provides a comfortable setting for professionals, couples, or small families seeking both style and convenience in one of Winter Haven’s most desirable walkable locations. With its architectural pedigree, prime downtown setting, and close proximity to the lakes, recreation, and major attractions, 503 Avenue B NW #503 offers a rare opportunity to enjoy living in the heart of Winter Haven.

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

Listing Agent: James Barris (863-258-6321)

Remarks: Under contract-accepting backup offers. This 2 BR, 2 BA home is located near Rotary Park and Kiwanis Park which is on Lake Martha, both public parks. Each park has room for games and family gatherings. Rotary Park has a baseball field with backstop and other outside activity areas. This home is located near schools, the Winter Haven downtown post office, the Winter Haven (Bay Care Hospital) and several doctors offices and medical clinics. The Winter Haven Public Library is also 6+/- blocks to the west of this property. The home has a metal roof which offers a long life and better storm protection than typical asphalt shingles. The windows have been replaced and the central A/c - Heat system has recently been inspected. A detached storage building provides room for lawn equipment or other items not needed inside the residence, but are more easily accessed than typical attic space provides.

Listing is courtesy of: TOWN & COUNTRY REAL ESTATE (863-293-1141)

Listing Agent: Timothy Irby (863-206-4464)

Remarks: Under contract-accepting backup offers. New price!!! Sellers are motivated. Move-In Ready 3-Bedroom Home on a Premium Lot in Villamar, Winter Haven! Welcome to 124 Emanuelle Dr, nestled in the sought-after Villamar community of Winter Haven! This beautifully maintained 3-bedroom, 2-bath home, built in 2021, sits on a premium lot and offers the perfect blend of comfort, style, and convenience. Step inside to discover a bright, open floor plan designed for modern living. The spacious living area flows seamlessly into a contemporary kitchen, making it ideal for entertaining family and friends. With move-in ready features, you can settle in and start enjoying your new home right away! Enjoy exclusive access to Villamar’s resort-style amenities, including a sparkling pool and a fun-filled playground—perfect for relaxing weekends or active afternoons. The premium lot provides extra space and privacy, setting this home apart from the rest. This home is ideal for families and first-time buyers seeking a welcoming community, modern comforts, and a low-maintenance lifestyle. Don’t miss your chance to own this exceptional property! Schedule your private tour today and make 124 Emanuelle Dr your new address.

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

Listing Agent: Jody Pagan (863-604-2367)

Remarks: Under contract-accepting backup offers. Short Sale. BANKRUPTCY SHORT SALE! Located In The Country Walk Community, This 2019 Built Home At 3180 Country Club Cir, Winter Haven, FL 33881 Features The Popular DR Horton Aria Floor Plan Offering 3 Bedrooms, 2 Bathrooms, & 1,672 Sq Ft Of Living Space. This Home Offers an Open Concept Layout With A Spacious Living Area, Split Bedroom Floor Plan, & a Functional Kitchen Overlooking The Main Living Space. Fenced Yard. Ideal For Everyday Living And Entertaining. Built In 2019, Conveniently Located Near Shopping, Dining, Schools, And Major Roadways With Easy Access Throughout Winter Haven. Bankruptcy Short Sale — Third-Party Approval Required. Property Sold As-Is. Great Opportunity For Owner-Occupants Or Investors Seeking Value In A Growing Area. Call Today For Details Or To Schedule A Private Showing.

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

Listing Agent: Jon Mccall, Pa (352-725-7206)

Remarks: Under contract-accepting backup offers. Welcome to this active 55+ waterfront community nestled along the peaceful canal between Lake Hamilton and Lake Henry, offering stunning lake views and private water access—perfect for boating and fishing. This charming 2-bedroom, 1-bath mobile home features a unique split-level layout that adds space and character. The main level offers a cozy living room and a private second bedroom. Upstairs, you'll find the primary suite, an eat-in kitchen and a spacious dining area—creating a comfortable and functional flow for everyday living. Enjoy a vibrant community lifestyle with a heated pool, nearby restrooms and changing facilities, well-kept shuffleboard courts, coin laundry, and secure RV/boat storage (available for an additional fee). The clubhouse hosts lively events like breakfasts, dinners, bingo, cards, billiards, ping pong, dances, shuffleboard, horseshoes, and more—all organized through a full community calendar. Gated entry ensures added privacy and peace of mind. The community operates on a 99-year land lease with a low $90/month HOA fee that includes water and sewer. Please note: no pets are allowed.

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

Listing Agent: Kristin Kellin (863-409-5649)

Remarks: Some homes are built. Others are crafted. Tucked away in a quiet Winter Haven neighborhood, 4599 Reynosa Drive is a rare, cedar-constructed residence that blends artisan craftsmanship with modern efficiency. From the moment you arrive, the home sets itself apart fully fenced with new vinyl fencing, enhanced exterior lighting, and a brand-new Trex front porch designed for relaxed mornings and long evenings. Inside, the warmth is immediate. Cedar wood wraps the interior, creating a natural, timeless atmosphere rarely found in Florida homes. The craftsmanship was completed by a skilled wood artisan, and the attention to detail is felt throughout custom wood features, soaring character, and a layout that feels both grounded and inviting. Tile flooring spans the entire downstairs, while all bathrooms are finished floor-to-ceiling in tile, offering durability and a clean, elevated aesthetic. The home has been thoughtfully upgraded for comfort and longevity, including brand-new hurricane-impact, double-pane windows with architectural tint reflecting up to 90% of heat, a new AC unit, new attic fan, insect-repellent insulation, and a fully sealed roof coated with heat-reflective, hurricane-rated paint. Even in peak summer, electric bills remain impressively low under $150 with no solar required. The kitchen and bathrooms feature newer plumbing, modern appliances (all just a few years old), and a standout stone-wrapped Jacuzzi tub, creating a spa-like retreat within the home. Side sliders bring in natural light and connect indoor living with outdoor space, while the garage includes sensor lighting, Hardie backer walls, full electrical, and AC, making it ideal for a workshop, studio, or flex space. The property is being offered fully furnished, including custom handcrafted wood furnishings (excluding beds and sofas), making it a true turnkey opportunity for a buyer who values character, quality, and immediate livability. Regular termite and pest control servicing adds peace of mind to this cedar-built, naturally insect-resistant home. Centrally located between Orlando and Tampa, with convenient access to major highways, shopping, and daily essentials, this home delivers both lifestyle and location. This is not a cookie-cutter property. This is a home with a story built to last, designed to feel different, and ready for its next chapter.

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

Listing Agent: Jason Prieto (877-366-2213)

Remarks: Spotless and beautifully updated, this ground-floor condo is located in the highly desirable Sandy Cove community on the Winter Haven Chain of Lakes. Move-in ready and thoughtfully improved, this 2 bedroom, 1 bath residence offers low-maintenance living that’s perfect for full-time enjoyment, a seasonal retreat, or a smart investment opportunity. Recent updates include attractive laminate hardwood flooring, quartz kitchen countertops, freshly painted interiors, new six-panel interior doors, double-pane windows, three-inch faux wood blinds throughout, and custom vertical blinds on the sliding doors. Major system improvements provide added peace of mind, including a newer A/C unit (2017) and a water heater replaced in 2021. The kitchen has been upgraded with stainless steel appliances, including a refrigerator and range (2018) and a microwave (2023). The inviting great room offers a comfortable and relaxed living space that flows seamlessly into the casual dining area, ideal for everyday living or gathering with family and friends. The updated kitchen features tile flooring, quartz countertops, stainless steel appliances, and a convenient stackable washer and dryer tucked neatly into the space for added efficiency. Both bedrooms are well sized at approximately 12x10 and offer generous closet space, with the primary bedroom featuring a full walk-in closet. The bathroom includes a tub and shower combination and is accessible from either bedroom, providing excellent functionality and convenience. Enjoy outdoor living with both front and rear lounging areas, including an enclosed back porch with screens and vinyl windows—perfect for relaxing or entertaining year-round. This ground-floor unit is ideally positioned just steps from the community clubhouse, grill area, and the heated pool maintained at approximately 85 degrees for year-round enjoyment. Sandy Cove also offers a community dock on Lake Lulu, part of the renowned Winter Haven Chain of Lakes, providing a peaceful setting to unwind, enjoy waterfront views, and take in beautiful Florida sunsets. Centrally located in Winter Haven, Sandy Cove delivers affordable condo living with easy access to shopping, dining, medical facilities, and all that Central Florida has to offer.

Listing is courtesy of: THE STONES REAL ESTATE FIRM (863-412-2080)

Listing Agent: Michael Stone (863-412-9733)

Remarks: Under contract-accepting backup offers. Move-in ready single-story home with NO HOA! This 3-bedroom, 2-bathroom gem features low-maintenance tile flooring throughout the entire home—no carpet here! The kitchen is stylishly appointed with stainless steel appliances and crisp painted cabinets. Enjoy outdoor privacy in the fully fenced backyard, perfect for relaxing or entertaining. Complete with a 1-car garage. A fantastic opportunity for easy living!

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

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

Remarks: Under contract-accepting backup offers. Welcome home to this beautifully updated 4-bedroom, 3-bath, two-story residence that’s truly move-in ready. The open-concept floor plan is ideal for everyday living and entertaining, enhanced by brand-new laminate flooring throughout the first floor for a fresh, modern look. The updated kitchen shines with new quartz countertops, freshly painted cabinetry, a new range hood, and new blinds—perfect for cooking and gathering. The home has been freshly painted inside and out and features new landscaping that delivers instant curb appeal. Upstairs, you’ll find new carpet throughout, along with a spacious primary suite complete with a walk-in closet and private bath—your own relaxing retreat. Three additional bedrooms provide flexible space for family, guests, or a home office. Step outside to a large backyard overlooking a tranquil pond, ideal for morning coffee, evening sunsets, or weekend barbecues. With a low HOA, a new roof and 2 x A/C in 2025, and all the major updates already completed, this home offers comfort, style, and exceptional value all in one.

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

Listing Agent: Beverly Amerman (609-381-2153)

Remarks: Short Sale. Charming, move-in ready 3-bed, 2-bath home in a peaceful Winter Haven community. Features an open living/dining layout, updated kitchen with modern finishes, and spacious bedrooms. Enjoy plenty of natural light, a private backyard perfect for gatherings and outdoor living, and an attached 2-car garage. Well-maintained and thoughtfully updated, this home offers both comfort and convenience. Monthly HOA of just $50 includes community maintenance for worry-free living. Close to shopping, dining, schools, and major roadways for easy commuting. Don’t miss this opportunity to own in a quiet, established neighborhood — schedule your showing today!

Listing is courtesy of: WORLD PROPERTIES GROUP (407-574-5920)

Listing Agent: Mona Cherkaoui (407-947-5736)

Remarks: Welcome to this spacious 3-bedroom, 2-bath manufactured home in the heart of Winter Haven! You'll love the layout, with a comfortable living room, a cozy den for extra hangout space, and a kitchen that opens up to a dining area—perfect for family meals or hosting friends. The master bedroom comes with its own en suite bathroom for extra privacy. Just off the kitchen, step into the screened patio that leads to a large garage that’s been converted into a handy workspace—ideal for hobbies, projects, or extra storage. Sitting on an oversized lot, there’s plenty of room to garden, play, or just enjoy the outdoors. Come check it out and imagine the possibilities!

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

Listing Agent: Ben Becton (863-617-0232)

Remarks: Live the lifestyle you’ve been dreaming about in Lake Ashton, Winter Haven’s premier 55+ gated community. This beautifully cared-for Ashton floor plan offers 3 bedrooms, 2 baths, a den, and 2,512 sq ft of thoughtfully designed space — but it’s the feeling of this home that truly stands out. From the manicured landscaping to the elegant leaded-glass French front doors, every detail reflects pride of ownership. Inside, natural light pours through plantation shutters and a full wall of 8’ sliding glass doors that draw your eye straight to your private backyard retreat. The kitchen is both stylish and welcoming, featuring Seacrest Birch cabinetry with soft-close drawers, designer Silestone countertops, and elevated details that make everyday living feel special. The primary suite is a peaceful escape with custom his-and-her closets and granite makeup vanity. The flexible den space is perfect for hobbies, guests, or a home office. As a certified Green Home by Environments for Living, you’ll enjoy energy efficiency and long-term savings. Step outside and this home truly shines. The oversized screened veranda with custom flooring, a beautifully designed outdoor kitchen, and a heated saltwater pool creates the perfect setting for quiet mornings, sunset swims, or entertaining friends year-round. The extended garage offers room for longer vehicles and even a golf cart, complete with epoxy floors and screened doors. And beyond your front door? Lake Ashton delivers resort-style living with golf, fitness center, clubhouse, pickle ball, tennis, dining, and endless activities — all in a vibrant, active community. This isn’t just a home. It’s the next chapter. Washer and dryer and front flag pole do not convey.Schedule your private showing today — you’re going to love it here.

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

Listing Agent: Anita Lowe (863-269-6461)

Remarks: Welcome to easy, carefree Florida living in the wonderful 55+ community of Oakwood Estates. This warm and welcoming neighborhood offers the perfect blend of relaxation and connection, with amenities designed to make every day feel like a getaway. Enjoy sunny afternoons at the community pool, friendly matches on the tennis courts, quiet moments in the library, or peaceful evenings fishing from the pier. This comfortable and spacious home features 2 bedrooms and 2 bathrooms, giving you plenty of room to relax and enjoy your surroundings. Start your mornings with coffee on the inviting front porch/lanai, or start a project on the side patio. Inside, the dining area showcases beautiful built-ins that add charm and character, while a convenient desk space near the kitchen provides the perfect spot for organizing recipes, paying bills, or planning your next adventure. Even better, a brand-new roof will be included with a full-price offer, giving you added peace of mind. Located in the dog-friendly section of Oakwood Estates, this home allows up to two pets (20 lbs each), so your furry companions can enjoy the lifestyle too. If you’ve been dreaming of a friendly community, warm sunshine, and a relaxed Florida lifestyle, this home is ready to welcome you. Schedule your showing today and start enjoying the retirement lifestyle you deserve.

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

Listing Agent: Kelly Fain (863-617-0074)

Remarks: Under contract-accepting backup offers. Luxury New Construction in Cypresswoods! MAJOR PRICE REDUCTION! Discover the perfect blend of modern design and upscale living in this brand-new 3-bedroom, 3-bath home with a bonus room and over 2,450 sq. ft. of heated space. Crafted with attention to detail, this residence showcases soaring ceilings, designer tile floors, granite countertops, and a sleek open-concept layout. The heart of the home flows effortlessly to the expansive lanai, ideal for indoor-outdoor entertaining or enjoying Florida’s year-round sunshine.Nestled in the sought-after Cypresswoods community, residents enjoy a lifestyle of comfort and convenience with resort-style amenities nearby, all while being just a short drive to world-famous Orlando attractions, Tampa entertainment, shopping, and dining. This home combines style, function, and location—a rare find ready to welcome its first owner!

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

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

Remarks: Pack your bags and move right into this fully furnished home. This home has many updates!! Although the bedrooms have updated carpets there is nice wood laminate flooring throughout the main living areas with plywood subfloor. The baths and front porch area have updated tile flooring. The kitchen has newer appliances, a beautiful mosaic backsplash and updated counter tops. All the windows are updated with double pane, thermal, tilt in windows. The updated entry door has blinds between the half glass that you can open for the light or close for privacy. Both bathrooms have updated vanities. Enjoy the updated and modern light fixtures. You get all this, plus the golf cart with new batteries is included in the sale of the home. The HVAC was installed in July 2023. The roof is a roof over adding extra insulation value to the home. Oakwood Estates is an active 55+ communities offering many amenities as well as activities. You can be as busy as you would like or just sit back and enjoy the peacefulness of the community.

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

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

Remarks: Move right into this very well maintained home. This home features some new vinyl flooring and newer windows. The hall bathroom has been upgraded with a new vanity and flooring. The home has had new plumbing installed in 2025 including a new water heater and washing machine. Just pack your bags and move right into this fully furnished home. Oakwood Estates, a 55+ community offers many amenities and activities. You can be as busy and join all the activities or just sit back and enjoy the peaceful community.

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

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

Remarks: Move right into this very well maintained home. This home comes furnished with most of what you see including dishes, pots and pans, and silverware. There is laminate flooring throughout the entire home. The roof was installed in 2010 and the air conditioner in 2011. The open living space makes the home very comfortable and appealing. The front porch area is incorporated into the living area and is perfect for entertaining. The washer and dryer are just 3 years old. If that isn't enough the golf cart is included. This home is located in Oakwood Estates, a 55+ community offering many amenities and activities. You can be as busy as you want or just sit back and watch the world go by!!

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

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

Remarks: What an amazing home just waiting for it's new owner!! The kitchen has been completely updated with new cabinets and flooring. The home offers two additional living spaces. The lanai on the side of the home is vented with the central ac and is included in the total square footage. or you can escape to the front porch which is also vented increasing the square footage by an additional 200 sf bringing the total living area to 1216 sf. The primary bathroom has an updated vanity. The laundry is located behind the side lanai so you don't have to go outside. The air conditioner is brand new in December 2025. This home is located in Oakwood Estates, a 55+ community which offers many amenities and activities. You can stay as busy as you like, or just sit back and enjoy the peaceful community.

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

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