Winter Haven Homes For Sale & Real Estate - 1036 homes

Remarks: Virtually Staged. Welcome to easy Florida living in the sought-after Orchid Springs 55+ community! This beautifully maintained 2-bedroom, 2-bath condominium is located in the desirable San Miguel Building and offers a peaceful second-floor setting with lovely views of the lush, landscaped grounds below. Step inside to find a spacious and comfortable floor plan designed for both everyday living and entertaining. The bright Florida room provides the perfect spot to enjoy your morning coffee, read a book, or simply relax while taking in the serene garden views. The primary suite offers a private retreat featuring an oversized walk-in closet and an updated bathroom with modern finishes, creating a comfortable and inviting space to start and end each day. One of the biggest advantages of this home is the exceptional value offered through the monthly HOA fee, which includes gas, water, sewer, trash, community pool, clubhouse, amenities, exterior maintenance, and grounds maintenance—allowing you to spend more time enjoying life and less time worrying about upkeep. Ideally located at 400 El Camino Drive, Unit 202, you’ll enjoy convenient access to shopping, dining, medical facilities, downtown Winter Haven, and the area’s many lakes and recreational opportunities. Whether you’re looking for a year-round residence, a winter getaway, or a low-maintenance lifestyle, this inviting condo offers the perfect combination of comfort, convenience, and affordability in one of Winter Haven’s most established 55+ communities. Come discover why so many residents love calling Orchid Springs home!

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

Listing Agent: Jessica Willaford (863-662-8549)

Remarks: Virtually Staged. Don't miss this charming 1-story home featuring 3 bedrooms, 1 bathroom, and a 1-car carport. The functional floor plan offers comfortable living spaces with plenty of natural light and room for everyday living. The kitchen provides ample cabinet and counter space, while the bedrooms offer flexibility for family, guests, or a home office. Enjoy the spacious yard with plenty of room for outdoor activities, gardening, or entertaining. Conveniently designed for easy living, this property presents a great opportunity to make it your own. One or more photo(s) has been virtually staged, AI generated, or rendered.

Listing is courtesy of: MAINSTAY BROKERAGE LLC (800-583-2914)

Listing Agent: Raquel Littlejohn (470-279-6333)

Remarks: Come see 2953 Whispering Trails Dr, a residence showcasing recent fresh interior paint and fresh exterior paint for a clean, cohesive appearance. The kitchen is equipped with all stainless steel appliances, and the primary bathroom provides practical double sinks. Outside, a welcoming patio leads to a fully fenced in backyard. This move-in ready property blends comfort and recent updates seamlessly. Included 100-Day Home Warranty with buyer activation

Listing is courtesy of: OPENDOOR BROKERAGE LLC (480-462-5392)

Listing Agent: Karen Albright (480-462-5392)

Remarks: Come see 1100 Carefree Cove Dr, recently improved with a new roof, fresh exterior paint, and fresh interior paint, presenting a comprehensively refreshed presentation. Partial flooring replacement further updates the interior living spaces, while a fenced in backyard provides practical outdoor areas. This property embodies a fresh approach to comfortable living. Included 100-Day Home Warranty with buyer activation

Listing is courtesy of: OPENDOOR BROKERAGE LLC (480-462-5392)

Listing Agent: Karen Albright (480-462-5392)

Remarks: Under contract-accepting backup offers. Winter Haven home near Chain of Lakes featuring 5 bedrooms, 3 bathrooms, and 2 flexible bonus rooms offering exceptional convenience and a lifestyle close to everything Central Florida buyers love. This move in ready property provides effortless access to major commuter routes, grocery stores, shopping, dining, scenic walking trails, LEGOLAND Florida Resort, and Florida’s beautiful beaches just about 90 minutes away. Step into your own private outdoor sanctuary designed for both relaxation and entertainment. The caged saltwater pool includes a 6×10 sun shelf perfect for in water lounging along with a 3 to 6 foot depth range ideal for both play and leisurely floating. Enjoy the luxury of a heated spa with priority Jacuzzi jet action creating the perfect setting for evening unwinding, stress relief, muscle relaxation, or hosting friends for cozy nights under the stars. The spacious gazebo offers a shaded retreat for outdoor dining, socializing, or simply enjoying the Florida breeze. Practical upgrades elevate this property as it is equipped to support a home generator, has a warrantied water softener for supreme taste, two 5-ft gates that create a wide 10-ft entry to the backyard and a on-site shed adding valuable extra storage keeping everything tidy and easy to access. Inside, the home feels bright, modern, and truly move in ready. The open concept layout creates an inviting flow throughout, and the generous kitchen is perfectly suited for gatherings, meal prep, and everyday connection. With its flexible floor plan, this home easily accommodates large families, multi generational living, or hosting guests with comfort and privacy. A standout property offering both lifestyle and practicality. This home is a must see!

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

Listing Agent: Andrea Friedmann (863-661-6535)

Remarks: Pre-Construction. To be built. Your opportunity to build a brand-new home and personalize it to your style is here! This to-be-built residence in the growing Winter Haven area offers the rare chance to enjoy new construction while selecting many of your own interior and exterior finishes to truly make it your own. Designed with modern living in mind, this thoughtfully planned home will feature an open-concept layout, stylish finishes, energy-efficient construction, and the peace of mind that comes with owning a brand-new home. Buyers will have the opportunity to choose colors and select finishes, creating a space that reflects their personal taste and lifestyle. Located in one of Winter Haven's rapidly expanding areas, you'll enjoy convenient access to shopping, dining, parks, lakes, and major roadways while still appreciating the charm and relaxed atmosphere that Winter Haven is known for. An added bonus: FHA construction loans are accepted, creating an excellent opportunity for first-time buyers and those looking to build their dream home with flexible financing options. Secure your future home early and take advantage of the ability to customize it from the start. Photos are for demonstration purposes only and may depict upgrades, finishes, and features that vary from the completed home. Contact us today for available floor plans, customization options, and estimated build timelines.

Listing is courtesy of: MIHARA & ASSOCIATES INC. (813-960-2300)

Listing Agent: Heather Spinosa (813-506-1800)

Remarks: Move-in Ready and Income Potential in the Heart of Winter Haven! Imagine starting your day with a cup of coffee on the screened porch, taking a short stroll to nearby lakes, and enjoying the convenience of being just minutes from Winter Haven Hospital, Polk State College, Lake Martha, and Lake Elbert. This charming 2-bedroom, 2-bath home offers the perfect blend of comfort, convenience, and opportunity. Thoughtfully updated with a new roof, electrical, and plumbing in 2024, this home is ready for its next owner to move in and enjoy. Inside, you'll find a warm and welcoming floor plan featuring separate living and dining spaces, an inside laundry room, and generously sized bedrooms with large walk-in closets. The primary suite offers a private en-suite bath, creating a comfortable retreat at the end of the day. Outdoor living is just as inviting, with both a welcoming front porch and a screened back porch perfect for relaxing, entertaining, or enjoying Florida's beautiful weather year-round. A storage shed provides additional space for tools, hobbies, or outdoor equipment. What truly sets this property apart is the detached unfinished ADU. Already equipped with a newer roof and updated electrical service, it's ready for your vision. Create a guest suite, home office, art studio, workshop, or future income-producing rental. Whether you're a first-time buyer, downsizing, investing, or simply looking for a home with room to grow, this property offers endless possibilities in a location you'll love. Don't miss this unique opportunity to own a home with both charm and future potential in the heart of Winter Haven.

Listing is courtesy of: PALMANO GROUP RE BROKERAGE LLC (321-214-1211)

Listing Agent: Denise Pohlmann (407-701-3346)

Remarks: Under Construction. Brand new, energy-efficient home available by Jul 2026! Configure the flex room in the front of the home to an at home office space or hobby space. Past the foyer, the open kitchen flows to the dining space, great room and outside patio. Private primary suite offers a spacious area to relax. Visit Villamar and explore new single-family homes for sale in Winter Haven, FL. Residents will have access to two resort-style amenity centers featuring a clubhouse, pool, and playground. Winter Haven is known for its beautiful chain of lakes with lakeside restaurants and its award-winning community theater. Nearby attractions include Legoland Florida and Peppa Pig Theme Park. A brand-new model and new phase are coming soon. Each of our homes is built with innovative, energy-efficient features designed to help you enjoy more savings, better health, real comfort and peace of mind.

Listing is courtesy of: MERITAGE HOMES OF FL REALTY (813-703-8860)

Listing Agent: Bryan Sumner (813-336-5895)

Remarks: Located in a desirable gated community on a oversized corner lot, paved driveway and low HOA fee and convenient access to everything Central Florida has to offer. This spacious and well-maintained home offers flexibility, comfort, and thoughtful upgrades throughout. Step inside to discover a bright and airy floor plan featuring a spacious living room with soaring vaulted ceilings and an open-concept design perfect for both everyday living and entertaining. The kitchen overlooks the main living area, creating a seamless flow, and features solid wood cabinetry, ample counter space, and plenty of storage. The versatile office can easily be converted into a fourth bedroom, providing additional space for family, guests, or a home office. The spacious primary suite is a true retreat, complete with elegant tray ceilings and a luxurious en-suite bathroom featuring dual vanities, a relaxing garden tub, walk-in shower, and a large walk-in closet. Additional highlights include a roof replaced in 2022, two AC units for enhanced comfort and efficiency, a large rear lanai perfect for outdoor relaxation, and a storage shed offering extra space for tools and equipment. Ideally situated in Winter Haven, you'll enjoy easy access to excellent shopping, dining, and entertainment options. Popular destinations include the vibrant downtown Winter Haven district, numerous waterfront restaurants along the Chain of Lakes, and shopping at nearby centers featuring national retailers and local boutiques. Outdoor enthusiasts will appreciate the area's beautiful lakes, parks, boating opportunities, and recreational amenities. Families and visitors alike will enjoy being just a short drive from LEGOLAND Florida Resort, one of Central Florida's premier attractions. Whether you're looking for a growing family home, extra space for remote work, or simply a peaceful gated community lifestyle, this exceptional property offers the perfect combination of location, value, and functionality. Schedule your private showing today!

Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (863-701-2350)

Listing Agent: Andrew Fearn (863-812-1755)

Remarks: HUGE $45,000 PRICE DROP! Welcome to one of the largest homes in the desirable Harmony Lake Eloise community! This spacious 5-bedroom, 3-bathroom residence offers a versatile and thoughtfully designed layout perfect for modern living. A generously sized flex room—currently used as a dining area—can easily be converted into a 6th bedroom, home office, or bonus space to suit your needs. The spacious kitchen is a true centerpiece, featuring quartz countertops, beautiful cabinetry, recessed lighting, stainless steel appliances, a large kitchen island, and a walk-in pantry. The interior paint throughout the home offers a soft, inviting color palette that’s easy on the eyes. The first floor showcases beautiful tile flooring throughout, along with a large bedroom and full bathroom—ideal for guests or multigenerational living. You’ll also find an additional sitting area or playroom, providing even more functional living space. Upstairs, all bedrooms are upgraded with luxury vinyl flooring, offering both style and durability. The conveniently located upstairs laundry room adds everyday ease. The expansive primary suite boasts his-and-her closets, dual vanities, and a walk-in shower —your own private retreat. With tons of storage throughout and one of the largest floor plans in the community, this home combines space, comfort, and flexibility. Enjoy a low monthly HOA fee and access to a beautiful community pool. Ideally located just minutes from Lake Eloise, Legoland Florida Resort, shopping, dining, schools, and major roadways, with easy access to Orlando, Tampa, and Walt Disney World. This is a must-see property in Winter Haven!

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

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

Remarks: Discover this must-see Tourmaline home. Included features: an inviting covered entry; an expansive great room; a well-appointed kitchen offering 42" cabinets, quartz countertops, a roomy pantry, a center island and an adjacent dining area; a beautiful primary suite showcasing an immense walk-in closet and a private bath; a convenient laundry; an airy loft; a storage area and a covered patio. This home also offers ceiling fan prewiring in select rooms.

Listing is courtesy of: AXEN REALTY, LLC (480-399-1218)

Listing Agent: Stephanie Morales, Llc (407-399-2055)

Remarks: Discover this stunning Ruby home, ready for quick move-in! Included features: a welcoming covered entry; a smartly planned kitchen boasting white 42" cabinets, a center island, a large walk-in pantry, and an open dining area; an immense great room; a secluded primary suite showcasing a generous walk-in closet and a private bath; three secondary bedrooms; a shared hall bath; a central laundry; and a comfortable covered patio. *Take advantage of special financing on quick move-in homes OR buy a to-be-built home and enjoy up to $20,000 in Flex Funds toward homes that can close in a timely manner! Options may vary by community, and offers are available on select homes on a first-come, first-served basis. Contact builder for more information!

Listing is courtesy of: AXEN REALTY, LLC (480-399-1218)

Listing Agent: Stephanie Morales, Llc (407-399-2055)

Remarks: Updated 3 bedroom / 2 bathroom home located at 2018 Marilyn Ave, Winter Haven, FL 33881. This 1968-built home has been personally improved and maintained, with many major updates already completed. The property features a 50-year metal roof installed in 2017, Trane XL20i high-SEER 2-stage A/C system with humidity control, 3.5-ton air handler, digital thermostat, tankless water heater, and under-sink reverse osmosis drinking water system. The plumbing under the home has been redone with a resin-coated pipe system and includes a lifetime warranty. A 200-foot well is also located on the property and is not currently connected. Inside, the home features hardwood flooring in multiple areas, floating hardwood floors in the living room and hallway, tile in the kitchen/dining area, and generous closet space throughout. The kitchen includes wood cabinets, stainless appliances, breakfast bar seating, reverse osmosis drinking water, convection microwave/oven, and good cabinet space. All appliances stay with the home, along with the living room TV and sound bar. The guest bathroom has been upgraded with travertine tile, glass shower doors, black fixtures, recessed lighting, and a clean updated look. Both bathrooms include Govee lighting, and additional Govee lighting is available for the front exterior of the home. Outside, the property includes a fenced backyard, patio area, garage, laundry area, and travertine firepit setup. The firepit can be used as a traditional firepit or converted to gas, with a sleeve already run for future gas use. The yard provides space for outdoor seating, landscaping, gardening, and other outdoor improvements. Additional exterior improvements are planned, including driveway paint, back porch paint, garage floor coating with flakes, pressure washing of the fence and house, front landscaping, and sand around the firepit area. Conveniently located near Downtown Winter Haven, Polk State College, shopping, dining, lakes, parks, medical offices, and major Winter Haven attractions. This property is a strong option for anyone seeking an updated home with major systems already improved and room to personalize the finishing touches.

Listing is courtesy of: BEYCOME OF FLORIDA LLC (804-656-5007)

Listing Agent: Steven Koleno (804-656-5007)

Remarks: Welcome 55+ or investors! This well-maintained one-bedroom, one-bathroom condo with an additional bonus room is the perfect place to retire and take it easy, or a fantastic addition to your investment portfolio. Located in the heart of Winter Haven, this home is just a mile from Legoland, shopping, and dining. The community also features a sparkling pool for you to relax and enjoy year-round. Don't miss out on this prime opportunity!

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

Listing Agent: Angela Perkins (863-280-5396)

Remarks: Amazing investment opportunity with NO HOA on a fenced 0.35-acre lot! This 3BR/1BA traditional-style home features central A/C, luxury vinyl flooring, and a dedicated laundry room. The expansive property includes a workshop and multiple storage sheds, offering plenty of room to build, create, or store equipment. Bring your creative ideas to update this handyman special and build instant equity. The seller is highly motivated, willing to assist with closing costs, and offering Owner Financing with down payment. Property is being sold as-is. All measurements to be verified by buyer. Don't miss out on this high-potential Winter Haven property!

Listing is courtesy of: GALLAGHER REALTY LLC (863-529-9883)

Listing Agent: Roxan Jarvis (863-698-5630)

Remarks: This sprawling two-story luxury pool residence showcases exceptional craftsmanship and timeless elegance, enhanced by extensive upgrades throughout and a Generac home generator. From the moment you enter, you'll be captivated by soaring tray and cathedral ceilings, rich crown molding, and refined architectural details that create an atmosphere of sophistication and grandeur. Designed to inspire culinary excellence, the chef’s kitchen is appointed with a professional-grade gas cooktop, custom solid wood cabinetry, a hidden walk-in pantry, farmhouse sink, and a picturesque window framing serene views of Lake Winterset. A convenient built-in workstation, located near the spacious laundry room and oversized three-car garage, provides added functionality for everyday living. The sumptuous primary suite serves as a private retreat, featuring beautiful custom built-ins, dual vanities, a chandelier-accented soaking tub, an expansive walk-in shower, and generous his-and-her custom closets. A tranquil sitting area offers the perfect space for reading and relaxation, while French doors provide direct access to the poolside lanai. Created for effortless entertaining, the grand great room seamlessly connects indoor and outdoor living through pocketing sliding glass doors that open to a spectacular pavered lanai complete with a summer kitchen, sparkling pool, and elegant water feature. Two additional en-suite bedrooms with walk-in closets are conveniently located on the main level, while a well-appointed powder bath serves guests. The upper level offers a private guest or in-law retreat featuring a spacious en-suite bedroom, full bath, media room, and a sizable studio or flex space overlooking the tranquil waters of Lake Winterset. Elegant formal living and dining rooms provide the perfect backdrop for memorable gatherings, enhanced by exquisite finishes and statement lighting. A distinguished library or executive home office, adorned with rich burled wood cabinetry and custom doors, delivers both privacy and sophistication.Situated on an oversized corner homesite, this exceptional residence is enveloped by lush, mature landscaping that creates a sense of privacy and exclusivity. Combining luxurious amenities, breathtaking lake views, and thoughtfully designed living spaces, this remarkable estate offers an unparalleled lifestyle in a truly spectacular setting.

Listing is courtesy of: RED BIRD REALTY (850-201-8810)

Listing Agent: Lisa Kleine (863-660-6787)

Remarks: Virtually Staged. Short Sale. Welcome home to Villa Mar, a vibrant and growing community in beautiful Winter Haven! Built in 2023 and occupied for just one year, this 5-bedroom, 3-bathroom home offers that “like-new” feel with thoughtful upgrades throughout. As you step inside, you’re greeted by an inviting open-concept layout designed for both comfort and connection. The kitchen shines with stainless steel appliances, an oversized pantry, and cabinets with updated fixtures, all opening to the main living area with NEW laminate flooring—creating a seamless space for gathering and entertaining. A bedroom and full bathroom on the main floor offer ideal flexibility for guests or multi-generational living. Upstairs, you’ll find four additional bedrooms, a loft that’s perfect for a home office or a cozy nook to unwind and recharge, and a conveniently located laundry room. The oversized primary suite features a large walk-in closet and an ensuite bathroom complete with a stand-alone shower, upgraded shower head, and linen closet for added convenience. Step outside to a fully fenced backyard, offering privacy and plenty of space to create your own outdoor retreat—whether that means adding a future pool, garden, or simply enjoying a quiet evening of relaxation. The oversized under-the-stairs storage and two-car garage add even more practicality, while the LOW HOA helps keep ownership easy and affordable. Perfectly situated just off US-27, residents enjoy proximity to dining, shopping, and grocery options, as well as easy access to I-17. Outdoor enthusiasts will love being near the Winter Haven Chain of Lakes, ideal for boating, kayaking, fishing, or simply soaking up the sunshine. Plus, the charming Downtown Winter Haven Historic District is nearby—home to local restaurants, boutiques, and community events like First Fridays, the Wine, Chocolate & Cheese Festival, and so many more! For a weekend of fun with the family and friends, LEGOLAND is only 3.5 miles away! This home beautifully blends modern comfort, functional space, and a convenient location—making it a must-see in the heart of Winter Haven. This is the one you've been waiting on. Schedule a showing today and make it yours!

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

Listing Agent: Brianna Perez Montalvo (407-687-3837)

Remarks: Virtually Staged. Welcome Home!!! 4577 Back Nine Dr. Winter Haven, Fl. features 3 bedrooms and 2 full baths and is located in Lake Ashton, an Exclusive Florida Retirement 55+ community. This home has BRAND NEW EXTERIOR PAINT! The widened, paver driveway offers extra room for parking and the screened entry at the front door is an added bonus. The glass leaded front door with large eye brow window above leads you into a home that is warm, inviting and spacious. The open-concept kitchen showcases granite countertops, stainless steel appliances, Maple cabinets and a Pantry Cabinet with convenient pull-out shelving. You can seamlessly blend indoor and outdoor living by sliding open the living room and dinette area sliding glass doors to the screened, covered lanai with 8" aluminum border base. It's the perfect place for entertaining. The primary bedroom with En-Suite bath has been extended 4 ft. to provide additional living space. It's the perfect getaway and you'll enjoy the EXTRA SPACE in the primary suite. The primary bathroom has ample closet space with His/Her Walk In Closets with Organization System, a large walk in shower with double shower heads, a separate water closet and separate His and Her Vanities. Her vanity has an additional make up area. Guests will appreciate the separate bedrooms and bath behind a pocket door. Additional features include: an automatic screen on the garage door, a separate irrigation meter, 18" diagonal tile in home (Bed 2 and Bed 3 are excluded), crown moulding, New A/C modulator, cabinetry in laundry room, Plantation Shutters in the Bedrooms, Upgraded entry light fixture, surround sound in the living room, additional insulation in the attic, new interior paint in Bedroom 1 and Guest Bathroom, new interior paint in the formal dining and dinette areas. Lake Ashton, a Florida Retirement community, has a Clubhouse with large grand ballroom, Outdoor Community Heated Pool, Tennis Courts, Bocce Ball, Shuffleboard, Fitness Center, Movie Theater, Bowling Lanes, Restaurant (Charm City)and More! The Health and Fitness center has indoor basketball, indoor racquetball, indoor heated pool, pickle ball and tennis courts, media center, card, craft and billiard rooms. There are two golf courses located in Lake Ashton. Memberships are optional and not a requirement to reside in Lake Ashton. Residents enjoy the resort style amenities and activities offered in Lake Ashton, a premier Florida Retirement Community. Don't miss this opportunity to own your piece of paradise. Check out the photo gallery and make your appointment to tour this home.

Listing is courtesy of: LAKE ASHTON REALTY INC. (863-221-5970)

Listing Agent: Lori Raath (863-409-6899)

Remarks: Pre-Construction. To be built. Lot 4 - Crown Model - Build the home you've always envisioned in beautiful Winter Haven! This to-be-built new construction home offers a unique opportunity to personalize your future residence from the very beginning. Buyers will have the ability to select interior and exterior color schemes and finishes, creating a home that truly reflects their individual style and preferences. Designed with modern living in mind, this home will feature a thoughtfully planned layout, quality craftsmanship, energy-efficient construction, and all the benefits that come with owning a brand-new home. Conveniently located near Winter Haven's shopping, dining, schools, parks, and the area's renowned chain of lakes, you'll enjoy both everyday convenience and the charm of one of Central Florida's fastest-growing communities. FHA construction loans are accepted, making homeownership more attainable for buyers looking to build instead of buy resale. Secure your homesite now and take advantage of the opportunity to customize your new home before construction is complete. Photos are for demonstration purposes only and may include finishes, colors, and upgrades that vary from the final product. Contact us today for available plans, timelines, and customization options.

Listing is courtesy of: MIHARA & ASSOCIATES INC. (813-960-2300)

Listing Agent: Heather Spinosa (813-506-1800)

Remarks: Great investor or first time home buyer opportunity. This house has new windows, a new roof, updated electric panel and an renovated bathroom. The LVP throughout the home with 5-1/4 baseboard. This property has a huge back yard for your family to enjoy. Built in laundry with washer and dryer included. This property is move in ready and won't last long at this price. Schedule your showing today

Listing is courtesy of: XCELLENCE REALTY, INC (866-595-6025)

Listing Agent: Stephen Hubbell (863-559-5666)