Winter Haven Homes For Sale & Real Estate - 1041 homes

Remarks: WATERFRONT! ON THE CANAL TO THE CHAIN OF LAKES!! This townhouse is low-maintenance and offers a tranquil setting right in the middle of town, great location!. Primary bedroom with ensuite and screened-in balcony, one car garage and open concrete patio. The screened patio is perfect for enjoying views of boaters and paddle boarders passing between the lakes. Focusing on recreation, this home is in the perfect spot for a multitude of outdoor activities. Community features include a sparkling pool . Fish from your backyard at the bank of Lake Lulu! This residence is convenient to Great restaurants, medical, shopping, entertainment, and LEGOLAND! Check us out today to see what Florida waterfront living is all about!

Listing is courtesy of: CROSBY & ASSOCIATES, INC. (863-293-5600)

Listing Agent: Rick Hemenway (863-289-5657)

Remarks: Seller motivated. Welcome to your home in Winter Haven—just minutes from Legoland, shopping, medical facilities, and Highway 27 for easy commuting! Originally a 3-bedroom, 2-bath layout, this home has been converted into a spacious 5-bedroom, 2-bath residence, offering incredible versatility for growing families, multigenerational living, or those needing extra space for a home office or hobby rooms. It will need some TLC due to tenant being in property. With five true bedrooms, everyone in the family can have their own retreat while still enjoying generous shared living spaces. Outside, you’ll find a property ideally situated for convenience—whether you’re heading to Legoland for weekend fun, accessing everyday amenities just minutes away, or commuting via Highway 27. This home offers the perfect blend of location, and space in one of Winter Haven’s most desirable areas.

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

Listing Agent: Brandy Duncan (863-585-6849)

Remarks: Under Construction. 2-story new construction townhome with 1,604 square feet, 3 bedrooms, and a covered lanai, located in the brand-new Harbor of Lake Henry community. Downstairs, enjoy an open layout(optional first floor layout with den)and a gourmet kitchen with, shaker-style wood cabinets, Samsung stainless steel appliances, including a pantry. The spacious gathering room opens to your covered lanai. The entire lower level and upstairs baths are finished with luxury vinyl plank flooring, with stain-resistant carpet in the bedrooms. Upstairs, you'll find three spacious bedrooms including your owner's suite complete with a walk-in wardrobe, linen closet, and a private en-suite bath with dual vanities and a tiled shower. Additional features for your convenience include a half bath downstairs, upstairs hall bath for the secondary bedrooms, energy-efficient insulation and windows, and a full builder warranty.

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

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

Remarks: Welcome to TRADITIONS, an active 55+ gated community located in the heart of the state on Lake Ruby. From swimming laps in the olympic size pool, casting a line at the lake, swinging a pickleball racquet or utilizing the fitness room and scheduled classes, there is plenty to do to stay in shape. If you prefer a more relaxed day, the clubhouse provides plenty of social spaces for card games, crafting, puzzles and reading a book. The community has planned monthly activities, they even plan a yearly community cruise if that's your vibe. You don't need to leave the community to find something to do, however; Disney and Universal Studios are nearby and you can reach either coast in less than two hours. The community is close to shopping (Publix coming soon), medical facilities, Legoland and the quaint downtown area of Winter Haven with boutique shops and local restaurants. This community is truly the ultimate 55+ lifestyle. The monthly dues include: community amenities, Spectrum cable and internet, lawn maintenance, common area maintenance, and exterior paining every 8 years. Now for the house: This is a Kennedy model floorplan, one of the most sought after in this community. It is a SHOW STOPPER from top to bottom and these Sellers have executed great care during their ownership. You will appreciate some of the additions they have made such as the extended rear screened lanai with Coolaroo shades and a motorized hurricane shutter. They also extended a paver BBQ area for those who like to grill. They added overhead storage racks in the garage and if you are an angler you will appreciate the storage system for the fishing poles! They have also added a motorized screen door for the days that you want to tinker in the garage and keep the bugs out. The exterior was just painted in 2025. The lawn is manicured with professional landscape edged flower beds and best of all the grass is maintained by the HOA. Step inside the front door to be instantly impressed with the high ceilings. The space is open enough for great entertaining but also offers space to spread out when needed. Ceramic tile in all the wet areas and living spaces with 5 inch baseboards and crown molding give the feeling of luxury. Recessed lighting, pendant lights as well as good window placement bring good lighting into the space. The kitchen is spectacular. 42 inch upper cabinets, quartz counters, walk in pantry and preparation island make the space functional for the chef and easy to entertain in. There are three dining space choices: formal dining area, breakfast nook and a breakfast bar providing with plenty of seating. The living room flows perfectly from the triple sliding door onto the lanai. The wall mounted TV's convey. The floorplan also offers a triple split bedroom plan. The primary bedroom offers an ensuite and the walk in closet has custom built in shelving. The ensuite has dual sinks, private commode room, linen closet and soaking tub. The walk in shower has no step and has nice glass doors. The 2nd and 3rd bedrooms share a guest bath with dual sinks and the 4th bedroom has a private ensuite. You truly have to see this home to appreciate its flow, style, tidiness and all the features that make this place a HOME! If 55+ living in Florida is what you have been dreaming of, you just found it! Come make some new Traditions!

Listing is courtesy of: DREAM REALTY GROUP (863-450-7973)

Listing Agent: Christie Weeks (863-450-7973)

Remarks: Valhalla - A GATED subdivision with pool, club house and more! 3-bedroom, 2-bath villa home with a connecting property but considered a single family home. This special villa has a functional layout with updated features throughout. A screened entry with leaded glass doors opens to vaulted ceilings and custom architectural touches. The open concept kitchen includes granite countertops, custom cabinetry, a center island with breakfast bar, Bosch dishwasher, stainless oven and range, walk-in pantry, and a passthrough to the living area for open flow. Wood plank flooring runs throughout the main spaces. The living room features large windows and an adjacent flex space for dining, office, or den use. The primary suite includes an ensuite bathroom with slate tile, jacuzzi tub, glass shower, dual sinks, and the laundry room is part of the primary. The guest room features a window seat and recessed lighting. A third room functions well as an office or additional guest space. HOA covers lawn care, water, trash, basic cable, pool, and tennis access.

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

Listing Agent: Karen Myers (863-651-4636)

Remarks: Cozy 3-Bed, 3-Bath Home Near Downtown Winter Haven Welcome to your next chapter in the heart of Winter Haven. This warm and inviting 3-bedroom, 3-bathroom home offers the perfect blend of comfort, convenience, and Florida charm. Just minutes from downtown, you’ll enjoy easy access to local shops, dining, parks, and community events while still coming home to a peaceful, cozy retreat. Step inside to discover a spacious layout designed for both relaxation and connection. Whether you’re hosting gatherings or enjoying quiet evenings in, this home offers plenty of room for your family to grow and make memories. One of the standout perks of this location is the proximity to beautiful Lake Silver. Spend your weekends enjoying water sports, lakeside strolls, or taking in the festive fireworks that light up the sky throughout the year. It’s a lifestyle that blends everyday comfort with a touch of lakeside magic. This home is ready to welcome its new family with open arms—and plenty of space.

Listing is courtesy of: COLDWELL BANKER REALTY (407-333-8088)

Listing Agent: Vanessa Marshall (321-377-3606)

Remarks: Minutes from Legoland and Peppa Pig Theme Park, this 5-bedroom, 3-bath home offers comfort and functionality in a quiet cul-de-sac. The open-concept layout features a spacious kitchen, main-floor den, and a first-floor guest suite with full bath. Upstairs includes a versatile loft and a primary suite with walk-in closet and dual vanity. Additional highlights include second-floor laundry, tile in wet areas, a 2-car garage, and a large backyard ideal for entertaining. Conveniently located near shopping and dining. Low HOA—perfect for first-time buyers or investors. (Tenant Occupied - Lease ends October 2026)

Listing is courtesy of: NEWBERRY REALTY & DEV GRP INC. (321-607-2354)

Listing Agent: Gylwerd Sevilla Oviedo (305-989-7853)

Remarks: Discover this gem in the heart of Winter Haven! This spacious home with 5 bedrooms and 3 full bathrooms combines comfort and style. Imagine natural light flooding every space, a modern kitchen, and generous areas for the whole family. Plus, you’ll

Listing is courtesy of: LA ROSA REALTY KISSIMMEE (407-930-3530)

Listing Agent: Maria Medina Fontes (210-480-9397)

Remarks: Welcome to your own slice of paradise on the private shores of Lake Lewis located in the highly sought-after gated community of Orchid Springs Estates! This stunning Mediterranean-style estate offers the perfect blend of luxury, comfort, and timeless elegance. Boasting 4 spacious bedrooms and 4 full baths, this custom-designed home features a beautifully appointed kitchen ideal for entertaining, a dedicated pool bath for added convenience, and multiple living spaces filled with natural light. Step outside to your private screened-in pool oasis, where tranquil lake views and tropical landscaping create the ultimate Florida lifestyle experience. Enjoy fishing, kayaking, or simply relaxing by the water in this serene, private lakefront setting. With premium finishes throughout and exceptional attention to detail, this home offers everything you need in one of the area's most distinguished neighborhoods. Don’t miss this rare opportunity—schedule your private tour today!

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

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

Remarks: Short Sale. Quaint 3/2 home perfect for 1st time homebuyers or could be a great rental property. Contract is contingent upon third party bank approval. Centrally located to major highways and shopping.

Listing is courtesy of: MILLSHIRE REALTY (863-815-8000)

Listing Agent: Robert Miller, Jr (863-899-9324)

Remarks: Move in ready and located on the Winter Haven Chain of Lakes! Welcome to the gated community of Casarena on the Lakes. This well-designed and meticulously maintained home is set up just right for indoor and outdoor living. The first floor is an open design with the fireplace separating the living and dining area. Enjoy granite countertops and updated appliances in the spacious kitchen that provides the perfect setting to create all of your favorite culinary delights. The living area is a versatile space with a cove for a hosting or exercise area. The main floor is also equipped with a half bath. Head upstairs to the loft that overlooks the living area and separates the two bedrooms. The primary bedroom leads to an open balcony on one side and an updated bathroom on the other. Both bedrooms are oversized with plenty of closet space. The new metal roof was installed in October 2023, The HVAC system has been well maintained, there is a new water heater and the home is also equipped with a whole home generator that is tested regularly. Enjoy the community pool, tennis or pickleball court and access to Lake Cannon, which is on the Winter Haven Chain of Lakes. Downtown Winter Haven is only 10 minutes away and you have quick access to Hwy 92 and 27. Call today for your private showing.

Listing is courtesy of: HOMETRUST REAL ESTATE & PTY MGT (863-450-0602)

Listing Agent: Kami Rickert (954-629-7828)

Remarks: Welcome to your new home, located in Dove's Rest, a 55+ community. This home features an open living area with a new refrigerator and stove. The Air Conditioner was installed in 2024 and the roof is 2021. The windows are a double pane window for added insulation value. The washer and dryer are located inside the home for convenience. This home will be sold mostly unfurnished with the bed in the second bedroom, bar stools, kitchen table, and mounted TV remaining. One dog under 20 lb is allowed. The community offers many activities and amenities including a clubhouse, pool, and shuffleboard. Join in with the many activities or just enjoy the peaceful community.

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

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

Remarks: Under contract-accepting backup offers. Welcome to this well-located single-family home situated on a quiet cul-de-sac in Winter Haven, offering a comfortable layout and enjoyable outdoor space. This home features 3 bedrooms and 2 bathrooms with a practical floor plan that supports everyday living. 2 car garage and a large driveway. Newer Shingle Roof 2023. Inside, the living area provides a straightforward, open flow into the dining space and kitchen, making it easy to stay connected whether you’re relaxing at home or hosting guests. The bedrooms are nicely sized, and the two full bathrooms add convenience and functionality. Out back, you’ll find a fully fenced backyard that offers privacy and room to enjoy the outdoors. The covered lanai is a great spot for casual outdoor seating, weekend barbecues, or simply spending time outside regardless of the weather. Whether you’re searching for a place to make your own or an investment opportunity, this home is worth a look. Schedule your showing today.

Listing is courtesy of: FLORIDA SPIRIT HOMES (407-396-4441)

Listing Agent: Gabriel Silva Andrada (321-666-0301)

Remarks: This meticulously maintained 3-bedroom, 3-bath home showcases eco-smart features and true pride of ownership, all within the sought-after 55+ gated community of Traditions. Thoughtfully designed and beautifully upgraded, this residence offers comfort, efficiency, and a relaxed Florida lifestyle. Upon arrival, you’re greeted by Florida-friendly landscaping accented with stone curb edging and a decorative paved walkway. The welcoming foyer features a transom window and a convenient coat closet. The spacious living and dining areas offer an open-concept layout enhanced with tile flooring—ideal for entertaining. Oversized sliding glass doors open to an extended screened-in lanai, seamlessly expanding the living space outdoors. The well-equipped kitchen features 42" upper cabinetry trimmed with crown molding, a stainless steel appliance package, and a walk-in pantry to meet all your culinary needs. A center island adorned with quartz countertops perfectly complements the glass tile backsplash, adding both function and style. The generously sized primary bedroom suite is a luxurious retreat, offering wall-to-wall carpeting and dual walk-in closets. The primary bath impresses with a handicap-accessible tiled shower featuring decorative listello tile, a comfort-height double-sink vanity, and a linen closet. A junior bedroom suite includes a private en-suite bath with a comfort-height vanity and quartz countertop—ideal for guests or extended stays. Step outside to your private oasis, where the paved screened lanai provides a peaceful setting for outdoor entertaining. This premium lot with no rear neighbors enhances privacy and tranquility. Additional Features & Upgrades Screened-in front entrance with paved walkway, Smart thermostat and smart home technology, Hybrid water heater, Low-E double-pane windows, Ring doorbell and MyQ garage door opener, Laundry room with washer and dryer, In-wall pest control system and termite bait traps, Exterior carriage lighting, Gutters, Two-car garage with epoxy finished floor. The picturesque Community of Traditions offers Planned Community Activities and an array of amenities such as a Lake Front Clubhouse, Dock & Boat Ramp, Heated Swimming Pool and Spa, Ballroom, Billiards, Meeting Room, Library, Computer Room, Craft Room, Dog Park, Tennis Courts, Basketball Court, Bocce, Shuffleboard, Fitness Center, and Aerobics Studio. Conveniently located near Shopping, Restaurants, Legoland and Major Routes, this home offers the perfect combination of luxury, comfort, and convenience.

Listing is courtesy of: CENTURY 21 MYERS REALTY LAKE WALES (863-676-4448)

Listing Agent: Eileen Belanger (863-221-0229)

Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Welcome home to easy Florida living in the beautiful, gated golf community of Cypresswood/Oak Grove! Tucked away on a quiet street, this 3-bedroom, 2-bath home offers the perfect blend of comfort, space, and relaxed lifestyle — plus major updates for peace of mind. From the moment you walk in, you’ll notice the soaring ceilings and natural light that make the home feel open and inviting. The layout flows effortlessly, with a formal dining space for holiday meals and special gatherings, along with a spacious eat-in kitchen featuring a breakfast bar that opens right into the family room — keeping everyone connected whether you’re entertaining or enjoying a cozy night in. The family room showcases tray ceilings and sliding glass doors leading to the enclosed patio — the perfect place for morning coffee, evening relaxation, or casual weekend get-togethers. It’s a wonderful extension of your living space and ideal for enjoying Florida’s year-round sunshine. The primary suite offers a peaceful retreat at the end of the day, while the additional bedrooms provide flexibility for guests, a home office, or hobbies. Even better, big-ticket items have already been taken care of — the roof was replaced in 2021, the water heater was replaced in 2023, home was freshly painted in 2022, and the A/C unit was replaced in 2018, giving you added confidence and long-term value. Living in Cypresswood means more than just owning a home — it’s about embracing the lifestyle. Residents enjoy a 24-hour manned gate, championship golf course, community pool, tennis courts, fitness center, and clubhouse. Spend your mornings on the course, afternoons by the pool, and evenings strolling through this beautifully maintained neighborhood. Conveniently located near shopping, dining, medical facilities, and major roadways, you’re close to everything while still enjoying the privacy and charm of a gated community. If you’ve been looking for comfort, community, smart updates, and a relaxed Florida lifestyle — this is it. Schedule your showing today!

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

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

Remarks: LOCATION, LOCATION! 17 minutes from Cypress Gardens! 8.2 miles away from LEGOLAND! 6 mins from Winter Haven Airport! 11 miles from I-4 east Ramp! 5 mins from Publix and many local restaurants, parks, lakeside views and much more. Located on a quiet road, the newly built 1550 sq ft modern home includes continuous luxury vinyl flooring on both floors, luxury quartz countertops with matching backsplash, two tone kitchen cabinets, neutral paint throughout , high ceilings. Ceiling fans throughout, with glass front door accent. Two tone exterior with ambient lighting and black and gold accents throughout the home. Kitchen includes Calacatta quartz countertop on 6 ft island and backsplash with off white uppers and oak lowers, half bathroom downstairs includes a black and gold designer vanity, upstairs guest bathroom has a pop of black and white arched mosaic detail in the shower included in the vanity mirror as well as the vanity. Master bathroom includes a double fluted wood vanity with drawers and shelves, LED light up mirror and large format black and white Calacatta porcelain tile in entire shower. Chic exterior with a pop of sage green on the front door. Chrome and brush nickel finishings, matching interior lower cabinets and all bathroom vanities are with a pop of color modern finishing included throughout such as LED lights, curved mirrors and matching bathroom tiles.

Listing is courtesy of: UNITED REAL ESTATE PREFERRED (407-243-8840)

Listing Agent: Lajuan Chambers (321-477-8805)

Remarks: Check out this well maintained home located in Oakwood Estates, a 55+ community, located in Sunny central Florida. The home features a very open and inviting kitchen, perfect for entertaining. The cooktop and built in oven have been updated. Step into the primary bedroom to find plenty of space for a king size bed, then step into the remodeled and updated primary bathroom. The split bedroom floor plan offers privacy to guests with a bathroom conveniently located outside the door. All the flooring is a laminate with no carpeting in the home. Enjoy the peaceful screened side porch. The home is located on a corner lot with a Florida room giving views of both streets, a great place for your morning coffee. The double pane windows and window AC offers additional living space when guests arrive. Oakwood Estates offers many amenities and activities. You can be as busy as you would like or enjoy the peaceful community and watch the world go by.

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

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

Remarks: Welcome to Carefree Country Club - one of Winter Haven't best kept secrets! Tucked away off of Cypress Gardens Boulevard, when you approach the GATED community, you know you're entering a really special place. Driving through, you're encompassed by the community's 9-hole golf course. Continuing on, you'll pass a stunning two-story clubhouse, plus all of the amenities (large thermal heated swimming pool; bocce ball courts; tennis and pickle ball courts; boat docks and boat launch). And finally, you'll pass by Lake Bess, which the community has over 3,000 private feet of shoreline on! This home sits just a few homes up from the lake, and there is no need to worry about flooding, as the home pitches down toward the lake! Believe it or not, this is actually a single wide home with a large addition! Entering through the sliding glass doors, you'll find yourself in the open living space, where the kitchen, dining area, and living room flow together. You get great views of the lake through the windows as well! The original structure also has a guest bathroom (with a shower / tub combo) and guest bedroom. The addition has the primary suite, with a nice sized closet, and ensuite bathroom with a walk-in shower. In here you will also find the washer. Out back is a storage shed that can fit a golf cart (as you will see one currently in there), as well as the dryer. The home was re-piped, so no need to worry about polybutylene (grey) pipes! The monthly fees include the following: lawn care; internet access in the clubhouse and golf center; garbage disposal and recycling; all of the amenities! This is a great home in a great community; schedule your showing today!

Listing is courtesy of: THREE MOUNTAINS REALTY (407-674-0220)

Listing Agent: Kathryn Valentine (407-674-0220)

Remarks: Welcome to the next exciting chapter of your life in Lake Ashton, Central Florida’s premier 55+ active-adult community, where this immaculately maintained three-bedroom, two-bath home with a den offers exceptional comfort and elegance, including a beautiful primary suite with its own relaxing sitting room and a sparkling 7½' x 36' bromine pool awaiting your enjoyment. From the striking stone front elevation and bronze screened front entry to the expansive 51' x 13' bronze screened veranda, this home impresses at every turn. Perfectly positioned on a large pond with a nature preserve beyond, it provides delightful sunrise views and frequent sightings of the abundant wildlife that makes Lake Ashton so special. Step inside through the elegant double glass doors and immediately notice the clean, crisp, and welcoming feel that creates the ideal setting for both relaxed everyday living and gracious entertaining. The interior showcases stunning terraced crown molding, coffered ceilings in both the living room and primary bedroom, and five solar tubes that fill the home with abundant natural light. The kitchen is beautifully appointed with gorgeous cabinetry featuring two glass-front cabinets, a wine rack, and rich black granite countertops, complemented by a large walk-in pantry offering generous storage space. Both bathrooms include walk-in showers and granite counters, adding style and convenience. One of the home’s most remarkable highlights is the expansive screened enclosure with pool at the rear of the property, where the views of the pond, wildlife, and nature preserve are among the finest along Hogan Lane. Additional peace of mind comes from an updated air conditioning system and a roof that is only three years old. Residents of Lake Ashton enjoy unmatched amenities including two championship 18-hole golf courses, a 26,000-square-foot clubhouse, a state-of-the-art health and fitness center, theater, pickleball courts, bowling alley, and so much more, creating an active and fulfilling lifestyle. This exceptional property offers the perfect blend of comfort, convenience, and community—schedule your private showing today and experience the very best of Florida living.

Listing is courtesy of: GLOBAL LIFESTYLE LLC (727-455-2709)

Listing Agent: Brad Kirwan (863-280-0390)

Remarks: OWN YOUR LAND! This home is located in Garden Grove Oaks, a community close to everything! A Clubhouse, pool, shuffleboard courts, and screened in hot tub to enjoy in the friendly 55+ community. An open front porch to enjoy the beautiful weather is enhanced by the front yard garden under the mighty oak! (Tree has been maintained/trimmed regularly) Light and bright, with laminate flooring throughout. The floor plan is open with the living room and dining room upon entering. The kitchen provides space for a bistro table, has a pantry, and great cabinet space. New Ceiling fans, faucets, regularly maintained AC, with 25 yr shingles from 2015. Inside laundry also has a utility sink! Both bedrooms are well sized and have walk-in closets. Primary bedroom has an en suite bathroom. Average total utilities are $150/month...water, sewer, electric! The owner has provided a copy of their 4-Point report just done in March for their insurance company. No grey pipe!

Listing is courtesy of: GOOD COMPANY REALTY INC. (863-585-9610)

Listing Agent: Sanda Andrews (863-585-9610)