Winter Haven Homes For Sale & Real Estate - 805 homes

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)

Remarks: Move right into this beautifully remodeled home. The open living area features an awesome kitchen with all a huge bar/work space. This home is perfect for entertaining, or just sit out on the open front porch and watch the world go by. There is no carpeting in this home, it is a vinyl plank throughout the home. The windows are a double pane insulated window adding to the energy efficiency of the home. The stackable washer and dryer is located in the shed. The side porch offers lots of room for storage, plus there is a shed out back. The shingled roof was installed in 2024 and the air conditioner was installed in 2020. There is also a water softener. The home comes furnished with what you see in the home as you are viewing it. Oakwood Estates, a 55+ community, offers many amenities such as shuffleboard, 2 pools and 2 clubhouses, tennis courts, miniature golf and much, much more.

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

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

Remarks: Spacious is the best word to describe this home. The home has 1440 sf plus a side porch for additional entertaining space. The home has two living areas and a wonderfully functional kitchen. The primary bedroom and bath allow for lots of space with two closets for his and hers clothes. The main bathroom is directly off the guest bedroom, making it convenient for guests. The hot water heater was replaced in 2024, roof in 2020 and HVAC in 2015. So this home is ready for it's new owners. The windows are a newer double pane for energy efficiency and the sliding patio door is also newer. The furnishings you see when you view the home will remain in the home. Oakwood Estates, a 55+ community, offers many opportunities and amenities. You can be as busy as you want, or just sit back and watch the world go by. Check this home out today!!

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

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

Remarks: Walk right into this open and spacious home. The kitchen is perfect for entertaining with newer cabinets and cooktop. The cathedral ceilings in the living room give the feel of lots of space. The floorplan offers 2 living areas. The guest bedroom has the main bathroom attached which is perfect for those overnight guests. The primary bedroom is spacious with two separate closets for him and her with a nice sized shower stall in the primary bathroom. The shingle roof was installed in 2021. The vapor barrier was replaced in 2023 and the home has new skirting. The side porch offers more living space and is backed with a great workshop area. The laundry is inside the home. If all that isn't enough there is an EV charging port installed. This home is located in Oakwood Estates, a 55+ community offering many activities or just sit back and enjoy the peaceful community. Make your appointment today!! This home will be sold unfurnished with appliances only.

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

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

Remarks: Check out the improvements recently completed!! The home is move in ready!! The flooring has all been replaced with new plush carpet and vinyl plank. The subfloor has been reinforced throughout the home. The home has a fresh coat of paint in soothing colors. The main bathroom has new wallboard to complement the updated vanity. The primary bathroom has a new wall cabinet installed. If you saw the home early in it's listing you must see the improvements. The air conditioner was replaced in 2022 and the roof is a roof over adding extra insulation value. The home is conveniently laid out with a very functional kitchen. The living room offers good space plus the front porch has a window air conditioner increasing the usable square footage. The primary bedroom has a nice sized walk in closet. Oakwood Estates has two pools, two clubhouses, shuffleboard, tennis courts and much, much more. You can be as involved as you would like or just sit back and enjoy the peaceful community. Make your appointment today!!

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

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

Remarks: Check out this wonderfully maintained home located in Oakwood Estates, a 55+ community. The HVAC has just been replaced and the roof is 3 years old. The living room is spacious and comfortable. Both bedrooms have walk in closets with lots of storage. The side and front porches provide additional living space. The home will be sold furnished less personal items with everything you will need to move right in. The amenities at Oakwood Estates include two clubhouses, two pools, a fishing pier, shuffleboard, tennis courts, miniature golf, and much more. You can join in of the many activities offered or just sit back and enjoy the peaceful community. Call today for your appointment to see this amazing home.

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

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