Winter Haven Homes For Sale & Real Estate - 927 homes

Remarks: Land, flexibility, and future income potential set this property apart. This well-maintained three-bedroom, two-bath home with bonus room and half bath sits on a spacious .93-acre lot, offering privacy and room to grow. The split-bedroom floor plan provides functional living, while the open living and dining areas create an inviting space for everyday life and entertaining. The kitchen offers abundant cabinet storage, and the primary suite features a walk-in closet and relaxing soaking tub. Polk County Building Division has approved the property for a secondary accessory dwelling unit up to 1,000 square feet, creating opportunity for multigenerational living, guest space, rental income, or a private office or studio. Enjoy nearly an acre of usable land with space for a garden, workshop, recreational vehicles, or outdoor entertaining. Conveniently located just minutes from the Chain of Lakes, LEGOLAND, parks, dining, shopping, and with easy access to both Tampa and Orlando. Buyer and buyer’s agent to verify all measurements and ADU requirements.

Listing is courtesy of: S & D REAL ESTATE SERVICE LLC (863-824-7169)

Listing Agent: Tiffani Kline (863-450-0207)

Remarks: Discover your serene retreat at Winter Haven Harbour Condos—a charming 55+ community featuring this delightful third-floor, two-bedroom, one-and-a-half-bath residence. Recently refreshed 3 years ago with a brand-new roof, fresh paint, and plush new carpeting in both bedrooms and the living space, this home is move-in ready. The kitchen is bright and functional, with plenty of cabinetry that extends into the dining area and ceramic tile flows seamlessly through the kitchen and baths. Enjoy a screened front porch, perfect for morning coffee. The community offers a large heated pool, a clubhouse, shuffleboard, and a grilling area—ideal for gatherings. Conveniently located near shopping, medical centers, and with easy access to both Tampa and Orlando, this is a rare opportunity. Schedule your private tour today!

Listing is courtesy of: HARPER REALTY FL, LLC (863-687-8020)

Listing Agent: Annie Wood (321-229-1913)

Remarks: Under contract-accepting backup offers. MOTIVATED SELLERS...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: One or more photo(s) has been virtually staged. Fully refreshed and move-in ready, this Ruby Lake home delivers space, thoughtful upgrades, and a layout that stands out from the rest. Offering high ceilings and a well-designed flow from the L-shaped formal living room that transitions into the formal dining area, creating a defined yet open feel. The kitchen sits at the center with a dinette overlooking the family room. A standout feature is the seamless connection to the outdoor space, with three separate access points to the 33x10 screened-in lanai, from the dinette, formal dining area, and primary suite—creating true indoor-outdoor living. The kitchen has been tastefully updated with brand new granite countertops, new range, and new microwave, along with ample cabinetry, a closet pantry, and breakfast bar. The primary suite is generously sized and opens into an en-suite featuring dual walk-in closets, split vanities, a garden tub, walk-in tile shower, and a private water closet. The split-bedroom floor plan offers privacy, while all bedrooms include walk-in closets. Recent improvements make this one stand out from others in the neighborhood, including brand new carpet throughout, fresh interior paint, and a new water heater, giving buyers peace of mind from day one. Located in the gated Ruby Lake community in Southeast Winter Haven, just minutes from convenient access to shopping, dining, Publix, Walmart, Legoland, and Hwy 27 for an easy commute.

Listing is courtesy of: STAR REALTY OF WINTER HAVEN (863-299-7827)

Listing Agent: Carlee Marchetti (863-258-3338)

Remarks: Under contract-accepting backup offers. Spacious and well-maintained 4-bedroom, 2-bath home with a private pool, offering 2,160 square feet of living space on an oversized 0.24-acre lot. Inside, vaulted ceilings create an open, airy feel throughout the main living areas, enhancing both natural light and functionality. The home also features a brand new HVAC system for added peace of mind. Step outside to a generous backyard with plenty of space beyond the pool to relax, entertain, or customize to your needs. Located in Winter Haven, this property offers convenient access to major roadways, shopping, dining, and the area’s well-known chain of lakes, making it easy to enjoy both everyday living and weekend recreation.

Listing is courtesy of: SOUTH CEDAR REAL ESTATE, INC (813-374-7907)

Listing Agent: Caylee Robles, Llc (920-639-2241)

Remarks: Under contract-accepting backup offers. Welcome to 3108 Buckeye Point Dr — where comfort meets convenience in the heart of Winter Haven. From the moment you arrive, this home invites you in with a layout designed for the way you truly live. With 4 bedrooms and 2 full bath and a brand new A/C system the living spaces feel open yet connected, creating an easy flow for both everyday routines and weekend gatherings. Natural light enhances the home’s warmth, while thoughtful design elements make each space feel intentional and livable. The kitchen serves as the hub of the home, seamlessly connecting to the main living areas — ideal for hosting, relaxing, or simply enjoying a quiet night in. The primary suite offers a private retreat, while additional rooms provide flexibility for guests, work-from-home needs, or hobbies. Step outside and imagine morning coffee, evening unwinding, and effortless Florida living in your own outdoor space. Located in a desirable Winter Haven community, you’ll appreciate the convenience to shopping, dining, medical facilities, schools, and major roadways — all while enjoying the feel of a tucked-away neighborhood setting. Homes that combine layout, location, and livability like this don’t stay available for long. Schedule your private showing and experience 3108 Buckeye Point Dr for yourself.

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

Listing Agent: Jp Phillips (863-670-7923)

Remarks: NO HOA | NO CDD | Move-in ready! Hi there! - I’m 2519 Avenue E SW, but you can call me home. I’m a new construction block home with 3 bedrooms, 2 bathrooms, and 2,063 sq ft of thoughtfully designed living space — plus a 2-car garage and NO HOA or CDD, giving you more freedom and affordability. I was built with comfort and style in mind. My high ceilings and large windows fill every room with natural light, creating a bright and welcoming atmosphere. My open-concept layout makes it easy to gather, entertain, and enjoy everyday living. My kitchen is one of my favorite features — a beautiful island space with granite countertops, stainless steel appliances, and plenty of cabinet storage, perfect for cooking, hosting, and making memories. When it’s time to unwind, my primary suite offers a peaceful retreat with a spacious bathroom, double vanity, elegant finishes, and a walk-in closet ready for you to make your own. I also have a dedicated laundry room, ceiling fans, and wood flooring throughout for added comfort and convenience. I’m located in a growing area of Winter Haven, just minutes from shopping, dining, parks, and major highways, making everyday living easy and connected. I’m move-in ready and excited to meet my new owners. Come take a look — I think we might be the perfect fi!

Listing is courtesy of: SIVEN PREMIER REAL ESTATE (813-419-7009)

Listing Agent: Fanta Traore (863-282-9602)

Remarks: Enjoy this clean 2 bedroom, 2 bath villa in the community of Mayfair Place. Step into a spacious great room with soaring ceilings and all ceramic tile floors throughout, offering both style and ease of maintenance. The open kitchen includes plenty of counterspace, gas range/stove, and breakfast bar. The primary suite features sliding glass doors leading to a peaceful back patio, the perfect spot for morning coffee or winding down in the evening. Inside utility room with extra cabinet and counter space, plus an additional storage closet for even more convenience. Just minutes from downtown, this villa provides easy access to local dining, shopping, and medical facilities.

Listing is courtesy of: STAR REALTY OF WINTER HAVEN (863-299-7827)

Listing Agent: Carlee Marchetti (863-258-3338)

Remarks: Welcome to your dream oasis—a stunning craftsman-style 3-bedroom, 2-bath saltwater pool home nestled on just over a quarter acre. This charming property features a large front porch, perfect for relaxing with your morning coffee or enjoying beautiful sunsets. Step inside to find a warm and inviting interior with classic crown molding throughout. The formal dining room offers an elegant space for entertaining, and it can easily double as a home office or flexible bonus room to suit your needs. A cozy dinette off the kitchen provides an additional casual setting for family meals. The backyard is a true retreat, boasting a huge fenced area that provides privacy and security. Dive into the sparkling pool, or unwind on the screened back porch, where you can enjoy the tranquility of your outdoor space. This stunning home also includes a 2-car carport, a long driveway for additional parking, and convenient boat parking—ideal for those who love life on the water. Located near the Lake Howard public boat dock, you’ll enjoy easy access to Winter Haven's sought-after chain of lakes. Additional features include a Generac generator for peace of mind, propane tanks for efficient energy use, and a storage shed for all your gardening tools and equipment. This home perfectly combines comfort, style, and functionality in a picturesque setting. Don’t miss your chance to make it yours!

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

Listing Agent: Michelle Howard (863-944-9920)

Remarks: Wow! Another huge price improvement!! Beautifully updated 4BR/3BA pool home with TWO master suites, NO HOA, and just steps from Chain of Lakes access! This modern, move-in-ready home features luxury vinyl plank flooring, a spacious great room overlooking the private backyard oasis, and a fully remodeled chef’s kitchen with custom soft-close cabinetry, quartz counters, stainless appliances, and a Ruvati workstation sink. The oversized primary suite offers a tray ceiling, walk-in closet, soaking tub, double vanity, and a large tiled shower. A second master/in-law suite creates ideal flexibility for guests or multi-generational living. Enjoy outdoor living on the 33’ screened lanai and the heated 30x15 in-ground pool surrounded by a fully fenced yard and a powered SmithBuilt workshop/shed. Recent updates include: roof (2019), replumbing (2019), AC handler (2019), kitchen remodel (2021), flooring (2021), pool heater (2022), variable-speed pool pump (2024), irrigation (2024), and guest bath remodel (2025). Located less than a 2-minute walk to the Lake Summit boat ramp with full access to the Winter Haven Chain of Lakes—perfect for boating, skiing, and fishing. Close to Legoland, shopping, dining, medical facilities, and convenient to both Tampa and Orlando. Stunning home in a highly desirable SE Winter Haven neighborhood with no HOA and endless possibilities! Seller may offer concessions with acceptable offer!

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

Listing Agent: Christina Loesch (347-977-0962)

Remarks: This move-in ready 3-bedroom Winter Haven pool home offers a fantastic combination of comfort, upgrades, and true Florida living on an oversized lot with no HOA. The home features a brand-new roof, new HVAC system and thermostat, new water heater, new pool pump and chlorinator, new laundry units, new exterior front doors, and an expanded driveway with ample parking. Inside, you’ll find a functional layout with generous living space and fresh improvements throughout. The private in-ground pool creates a relaxing backyard setting, while the large lot provides room for outdoor entertaining, storage, or future additions. Located minutes from the Winter Haven Chain of Lakes, Gene’s Lakeside Marina, LEGOLAND Florida Resort, golf courses, shopping, dining, and local parks, this property sits in one of Central Florida’s most desirable and fast-growing areas. With major updates already completed and convenient access to boating, recreation, and upcoming community development, this home is an excellent opportunity for first-time buyers, families, or investors.

Listing is courtesy of: THE URBAN GROUP, INC. (954-522-6226)

Listing Agent: Ashlee Morrell (941-740-9134)

Remarks: Under contract-accepting backup offers. Now's your chance! Buyer fall out of contract and this home is ready for you! Experience the perfect blend of "Old Florida" soul and modern peace of mind in the heart of the desirable NE downtown grid! This enchanting 1937 vintage gem at 624 Avenue A NE has undergone a comprehensive mechanical evolution over the last 6 months, making it one of the most insurance-friendly historic homes on the market. Major 2025/2026 Upgrades Include: NEW ROOF (6 months old) NEW AC SYSTEM for maximum efficiency ELECTRICAL UPDATES including a brand-new panel PLUMBING UPDATES with modernized piping throughout Inside, you’ll find stunning original hardwood floors and character-rich details. The true "X-factor" is the detached in-law suite—a blank canvas ready for your finishing touches. This versatile space is the ultimate flex-asset: perfect for an income-producing Airbnb, a secluded home office/studio, a private "man cave/she-shed," or a comfortable space for multi-generational living. Located in the premier NE downtown district, you are just steps from the walking trails of Lake Martha and the vibrant dining, boutiques, and breweries of revitalized Downtown Winter Haven. Enjoy a walkable, "park-to-pub" lifestyle with NO HOA and mature oak-canopy streets. With all the major "heavy lifting" already completed, this historic treasure is ready for its next chapter. Schedule your showing today!

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

Listing Agent: Veronica Bard (863-670-7526)

Remarks: The property you are inquiring about is located in Winter Haven, FL, in the Cypresswood area of Polk County. This is a price induced-to-sell home, located in a gated, guarded, golfing community. This is on the fairway so no backyard neighbors, and in a private, peaceful setting. This is a 2-bedrrom, 2-bath, 1,571 sq.ft. home with an open area concept. This house is looking for new owners to make it their own. Divided bedrooms, country-dine in kitchen, plus a gathering room for desired use. Additional enclosed lanai for added space, plus an oversized 2-car garage. Easy to view - call, text, email, and see it today! *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: BEAUTIFUL home built in 2025, featuring 3 bedrooms, 2 baths, and an open living area. The kitchen boasts an open and airy design, with a spacious center island perfect for entertaining, complemented by new stainless-steel appliances,and a walk-in pantry. The dining room is perfectly placed near the kitchen, providing the ideal setting for meals and celebrations of any kind. The family room serves as the natural gathering space of the home, perfect for entertaining friends and family or relaxing with a favorite book or movie. The living area, laundry room, and baths texture luxury wood vinyl plank flooring, with stain-resistant carpet in the bedrooms. The owner's suite includes a walk-in wardrobe and a private en-suite bath with dual vanities, a tiled shower, and a closeted toilet. 2-car garage, architectural shingles. Peace Creek Reserve is a Masterplan community of new single-family homes with a beautiful natural creek. Winter Haven is the chain of lakes city, with over 26 linked together by canal. There are lots of shops, restaurants, bike paths. Peace Creek Reserve is what you have been looking for. safe small town feel with convenience, the perfect place to raise a family.

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

Listing Agent: Marian Capriles Garcia (407-738-2301)

Remarks: Under contract-accepting backup offers. Welcome to a rare blend of space, flexibility, and opportunity at 525 7th St NE in the heart of Winter Haven. Set on a desirable corner lot with NO HOA, this property invites you in with a bright, open-concept design that feels both airy and welcoming from the moment you arrive. The main living area is thoughtfully designed for everyday comfort and effortless entertaining, featuring three spacious bedrooms and three full bathrooms. The kitchen serves as the centerpiece of the home, showcasing elegant stone (quartz) countertops, stainless steel appliances, updated cabinetry with under-cabinet lighting, and a generous dining area perfect for gathering with family and friends. A standout feature of this property is the private in-law suite, complete with its own entrance, bedroom, bathroom, and built-in kitchenette. Whether you're hosting guests, accommodating multigenerational living, or seeking rental income, this space offers exceptional versatility. Currently leased to a reliable tenant through April 30, 2026 with potential to extend. It provides immediate income potential for investors or future flexibility for homeowners. Significant upgrades add both value and peace of mind, including a new roof (2023), updated HVAC system (2022), smart garage door (2022), and approximately $60,000 in renovations completed between 2022–2023. Additional highlights include new flooring throughout, fresh carpet in key areas, and a custom built-in entertainment center with a Murphy bed for added functionality. Step outside to enjoy a fully fenced yard designed for relaxation and enjoyment. The welcoming front porch sets the tone, while the backyard offers a lush collection of fruit and plantings. You can find in the backyard mango, cherry, banana, lemon, and aloe vera creating your own private oasis. Conveniently located near Lake Elbert, Downtown Winter Haven, Polk State College, and a wide range of shopping, dining, parks, and medical facilities, this home delivers on both lifestyle and location. Whether you're searching for a primary residence, an income-producing property, or a home with flexible living options, this one truly has it all. Schedule a tour today.

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

Listing Agent: Veronica Figueroa (407-519-3980)

Remarks: Enjoy true Florida lakefront living in this spacious 2-bedroom, 2-bath home offering almost 1800 square feet of heated living space, perfectly positioned on a waterfront lot with your own private dock, ideal for relaxing, fishing, or simply taking in the peaceful views of Lake Henry. Inside, the home features a large kitchen with a center island, stainless steel appliances including a built-in oven and cooktop, and plenty of cabinet space for storage and functionality. The oversized family room offers some of the most beautiful lake views in the home, creating a bright and welcoming gathering space. French doors lead into the additional Florida room under air and heat, where the panoramic water views continue and provide a perfect year-round retreat. Both bedrooms are generously sized, with the primary suite featuring a large ensuite bathroom complete with a walk-in closet, double sinks, a shower, and a garden tub. The guest bathroom has been updated, offering a fresh and modern feel. Additional interior features include an entry foyer, inside laundry room, and ample storage space including a dedicated storage room. Outdoor living is just as impressive, with oversized parking, a carport, a large screened room, a paved open patio, and an additional storage shed. The combination of covered and open spaces makes it easy to enjoy the Florida lifestyle throughout the year. Major updates include a new roof in 2025, updated windows, and updated plumbing for added peace of mind. Located in Lake n Golf Estates, a desirable lakefront, LAND-OWNED 55+ community, residents enjoy access to amenities including a pool, spa, clubhouse, shuffleboard, and community boat ramp and dock, with boat slips available subject to availability. Conveniently situated near Hwy 27, medical facilities, shopping, and dining, the community also offers low HOA fees of $550 per year, adding to its overall appeal. Schedule your private showing today, lakefront homes at this price point do not last long.

Listing is courtesy of: RE/MAX HERITAGE PROFESSIONALS (863-256-2188)

Listing Agent: Patricia De Graaff, Llc (863-307-0061)

Remarks: Beautifully maintained and move-in ready 2BR/2BA home in desirable SE Winter Haven, located in Lake Dexter Moorings with low HOA and access to a community pool, private boat ramp, and dock on Lake Dexter. Major updates include a brand new roof installed February 2026 and fresh exterior paint, showcasing true pride of ownership. This well-cared-for home features a split bedroom plan with the primary suite in the rear and guest bedroom in the front. Spacious living/dining room combo flows into a bright kitchen with breakfast nook and ceiling fan. New laminate flooring throughout (tile in entry). Enjoy the large Florida room with sliding door access—perfect for entertaining. The primary suite offers a walk-in closet and en suite bath with a walk-in shower, and skylight. Guest bath is also updated with a skylight. Additional highlights include a fenced backyard, custom tile patio, and a 2-car garage with washer/dryer hookups, utility sink, and screened sliding door. A truly well-maintained home you don’t want to miss!

Listing is courtesy of: SUNSHINE INTERNATIONAL REALTY LLC (407-314-1827)

Listing Agent: Lizzie Zirillo (407-314-1827)

Remarks: One or more photo(s) has been virtually staged. NEW ROOF 2/9/2026 + $45,000 PRICE IMPROVEMENT! Lakefront living on the Chain of Lakes just became an incredible opportunity. Welcome to 4099 Island Lakes Dr — a well-maintained 3 bedroom, 2 bath block home offering breathtaking waterfront views and direct access to the Chain of Lakes. Major updates already handled with a brand new roof installed February 9, 2026, giving buyers peace of mind and potential insurance benefits. Combine that with a significant $40K price reduction, and this property stands out in today’s market. Inside, you’ll find a bright and open layout filled with natural light. The spacious living area flows seamlessly into the kitchen and dining space, ideal for entertaining or relaxing after a day on the water. The primary suite features beautiful lake views, a private bath, and generous closet space. Step outside to freshly installed sod and updated landscaping that enhances curb appeal and creates the perfect setting for outdoor gatherings. With direct lake access, enjoy boating, fishing, kayaking, and stunning sunset views right from your backyard. Whether you're searching for a full-time residence, seasonal escape, or lakefront investment, this Chain of Lakes home offers location, lifestyle, and value. Schedule your private showing today.

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

Listing Agent: Don Jerue (863-259-9550)

Remarks: Welcome to 4020 Carteret Dr in Winter Haven, a beautifully updated 4-bedroom, 3-bath home located in a desirable 55+ lakefront community with a 3-car garage offering comfort, convenience, and low-maintenance living in the heart of Central Florida. This thoughtfully designed home features stunning lake views, hardwood flooring, an updated kitchen with modern finishes, and stylish upgrades throughout. The spacious layout includes a mother-in-law suite, perfect for visiting family, guests, or additional privacy. Residents enjoy direct water access and a private community boat ramp, providing easy access to Winter Haven’s renowned Chain of Lakes, ideal for boating, fishing, and enjoying Florida’s outdoor lifestyle. The community also offers boat and water toy storage for a small fee, making it convenient to keep your boat or jet skis nearby and ready to use. One of the standout features of this home is the maintenance-free lifestyle. The HOA covers Cable, Internet, Exterior Home Maintenance including landscaping, mulch, and exterior painting, and More, allowing homeowners to enjoy their property without the typical upkeep responsibilities. Located just minutes from Cypress Gardens Boulevard, this home offers quick access to shopping, restaurants, grocery stores, golf courses, parks, and medical facilities. Residents are also close to LEGOLAND Florida Resort, and major roadways including US-27 and the Polk Parkway, making travel to Lakeland, Orlando, and Tampa convenient. If you’re searching for a Lake view home in Winter Haven, a low-maintenance home in a 55+ community, or a property with Ruby Lake access, 4020 Carteret Dr offers the perfect combination of location, lifestyle, and modern comfort in one of Polk County’s most established lake communities. Schedule a showing today!

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

Listing Agent: Sofia Lovinsky (407-376-1845)

Remarks: Welcome to this charming 2 bedroom, 2 bathroom home in Orchid Springs, a non–age-restricted community where all ages are welcome, located in SE Winter Haven. Thoughtfully updated, this home features new wood plank tile flooring. The open floor plan is highlighted by a spacious and light-filled great room with vaulted ceilings creating a warm and inviting space ideal for everyday living. Just off the great room is a beautiful atrium to fill with your favorite plants or enjoy the evenings outside in your private sanctuary. The primary suite includes built-in closets, sliding glass door open to the back courtyard and an en-suite bathroom with updated wood plank tile flooring, updated vanity and mirror the secondary bedroom is generously sized and located next to the guest bathroom, which features updated vanity and tile flooring. Additional highlights include a one-car garage with laundry area Outdoors, enjoy a paver patio courtyard ideal for BBQs and entertaining. There are plenty of private outdoor spaces for relaxing there is are front and rear screened porches as well as the outdoor courtyard. Orchid Springs is a well-established community offering a swimming pool and clubhouse, with lawn maintenance and amenities included for a low monthly fee. Conveniently located within minutes of shopping, dining, medical facilities, and LEGOLAND® Florida, and centrally positioned between Tampa and Orlando for easy access to theme parks and international airports. Call today to schedule your private showing.

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

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