Winter Haven Homes For Sale & Real Estate - 978 homes

Remarks: Under Construction. BELOW MARKET INTEREST RATES with use of Seller's Preferred Lender. Indigo - Check out the Indigo, a spacious two-story, 5-bedroom, 3-bathroom, 2-car garage home perfect for growing families or hosting guests. Enter the impressive foyer with soaring ceilings that creates an immediate sense of openness. From the foyer, the home effortlessly flows into the main living areas and kitchen. With quartz countertops throughout, stainless-steel appliances and a smart thermostat for energy efficient climate control, the Indigo brings all the things that matter together. The downstairs guest suite and bathroom are tucked away for added seclusion, while the open concept living space is perfect for entertaining. Upstairs, you'll find a generously sized recreation space, ideal for family time or unwinding. The owner's suite is a true sanctuary, featuring a walk-in shower, double vanities, and a spacious walk-in closet. A laundry room with a new washer and dryer is just off the owner’s suite, conveniently located near the 3 additional bedrooms and full bathroom. The Indigo is as functional as it is stylish, providing the perfect balance of comfort and modern living. Close to it all, Villa Mar places you near the natural beauty of the Winter Haven Chain of Lakes, the charm of downtown Winter Haven, and family fun at LEGOLAND® Florida Resort. Back at home, residents enjoy community amenities including a pool, dog park, playground, and walking trails. Images shown are for illustrative purposes only and may differ from actual home. Completion date subject to change. Contact or make an appointment for more details on interest rates.

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

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

Remarks: Under contract-accepting backup offers. •Motivated seller! Seller will contribute $10,000 at closing to be used at buyers' discretion for a permanent or temporary interest rate buy-down or closing fee. Move-In Ready 5 Bedroom Home with Resort-Style Amenities in Villamar This beautifully maintained 5 bedroom, 3 bathroom, 2,616 sq ft home is located in the desirable Villamar community. The home features both a living room and a family room that opens to the kitchen. The open-concept floor plan includes a spacious gathering room that flows into the dining area and a well-appointed kitchen complete with stainless steel appliances, shaker-style cabinets, a breakfast bar, and a walk-in pantry. The private owner’s suite offers a large walk-in closet, dual sinks, and a private water closet. Luxury vinyl plank flooring enhances the interior. A versatile downstairs bedroom and full bath provide flexible living options, ideal for a home office, guest suite, or multigenerational accommodations. Enjoy outdoor living on the covered lanai and large screened porch overlooking the preserve, along with beautifully maintained, Florida-friendly landscaping with irrigation. The community resort-style pool is perfect for relaxing in the Florida sun.

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

Listing Agent: Irene Bryan (863-289-6789)

Remarks: This is a beautiful condo located in the heart of Downtown Winter Haven, FL. The sunsets over Lake Howard are unbelievably gorgeous and can be enjoyed sitting on either patio overlooking the waterfront. This is an end unit that comes with 2 covered parking spaces located directly underneath the space. A must see.

Listing is courtesy of: COLLANY PROPERTIES (863-295-9886)

Listing Agent: Christopher Collany (863-412-2170)

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 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. Luxury vinyl floors throughout the entire home . Kitchen is two tone with off white and sage green on lowers with Calacatta gold with large veining on 6ft island and up the backsplash detailed with precision, large pantry and extra closet on first floor and ceiling fans throughout entire home!

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

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

Remarks: Welcome to modern comfort in the heart of Winter Haven! This meticulously maintained 4-bedroom, 2-bathroom home is a move-in-ready living space. The residence features a bright, open-concept floor plan with a seamless flow between the kitchen and living areas, complemented by durable tile and laminate flooring. Enjoy outside living in your private fenced in backyard or sit on the enclosed patio and enjoy the outdoors. Florida living at its best!

Listing is courtesy of: SPANN & ASSOCIATES REAL ESTATE (407-468-7512)

Listing Agent: Kal Scarvers (863-617-5236)

Remarks: One or more photo(s) has been virtually staged. Welcome to 441 McKenna Dr, a well-maintained 4-bedroom, 2.5-bath home in the Lucerne Park Reserve community, where modern design, energy efficiency, and everyday functionality come together in a comfortable Winter Haven setting. From the moment you enter, the home feels bright and open, featuring a clean, neutral palette and durable tile flooring throughout the main living areas. The open-concept layout seamlessly connects the kitchen, dining, and living spaces, creating an ideal environment for both daily living and entertaining. Here is a clean, MLS-appropriate disclaimer you can use: --- All information provided is deemed reliable but is not guaranteed and should be independently verified by buyers and their agents. Room dimensions are approximate and should be measured for accuracy. HOA fees, rules, and restrictions are subject to change and must be confirmed directly with the association. Information regarding the solar system, roof, utilities, and other property features is based on seller representations and has not been independently verified. Listing broker and seller make no warranties, expressed or implied, as to the accuracy of the information provided. The kitchen serves as the heart of the home, showcasing white cabinetry, stainless steel appliances, quartz countertops, ample prep space, and a central island that naturally brings everyone together. The living area is enhanced by a decorative feature wall with a fireplace focal point, adding character and visual interest beyond standard finishes. Large sliding glass doors invite in natural light and provide direct access to the fenced backyard, offering a versatile outdoor space for relaxing, entertaining, or pets. The primary suite features a spacious bathroom with dual sinks, quartz countertops, a glass-enclosed shower, and built-in shelving for added storage and convenience. Additional bedrooms offer flexibility for guests, a home office, or hobbies, while the half bath provides added convenience for visitors. A dedicated laundry room further enhances the home's functionality. This home also includes smart outlet features compatible with Alexa, allowing for convenient voice-controlled functionality and adding a modern smart-home element that enhances everyday living. One of the standout features is the seller-reported solar panel system, designed to produce 100% of the home’s energy consumption. According to the seller, the electric bill is typically around $40 or less per month, reflecting primarily the grid connection charge. The seller will also pay for the solar transfer, adding significant long-term value. Additionally, the seller reports a new roof installed in 2024. Located in Lucerne Park Reserve, residents enjoy access to community amenities including a pool, playground/tot lot, and scenic lakes. The Winter Haven location offers convenient access to shopping, dining, healthcare, schools, and local attractions including LEGOLAND Florida Resort. This property offers a compelling combination of modern features, energy efficiency, and community living—making it an excellent opportunity for buyers seeking both comfort and long-term value. One or more photo(s) has been virtually staged.

Listing is courtesy of: NEXTHOME MY WAY (407-544-4545)

Listing Agent: Angel Pabon (407-544-4545)

Remarks: Under contract-accepting backup offers. Charming and efficient 1-bedroom, 1-bath home in Winter Haven, perfect for simple living or an investment opportunity. With 480 sq ft, this home offers a functional layout that makes the most of the space, including a cozy living area, kitchen, and private bedroom. The property sits on a spacious lot, giving you room to expand, add outdoor features, or simply enjoy extra space — a rare find for a home this size. Conveniently located near shopping, dining, and major roads, this home is ideal for buyers looking for an affordable option or investors seeking rental potential. Great opportunity with plenty of possibilities—schedule your showing today.

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

Listing Agent: Malak Hassani Benbachir (863-624-7266)

Remarks: Under contract-accepting backup offers. Welcome to 333 Lake Howard Dr NW, Unit 313A — a beautifully updated 2-bedroom, 2-bath condo located on the top (3rd) floor of a well-maintained 55+ community. The building offers elevator access and is wheelchair accessible, providing both comfort and convenience. This move-in ready unit features large windows in the living room overlooking the community pool, filling the space with natural light and offering peaceful views. Recent updates include all new kitchen cabinets and countertops, a new lanai cabinet, upgraded bathrooms, a new walk-in shower, new carpet throughout, fresh interior paint, new light fixtures, and new vent covers. The roof has also been replaced, adding additional value and peace of mind. Residents enjoy a variety of amenities including a community pool, fitness center, and direct lake access to Lake Howard. The private dock and boat parking make it easy to enjoy fishing, relaxing by the water, or docking your boat — all included in the HOA dues. Additional features include assigned covered carport parking and a 4x4x4 extra storage space located on the 2nd floor. Enjoy low-maintenance living with resort-style amenities in a prime location.

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

Listing Agent: Brian Cox (863-559-3627)

Remarks: One or more photo(s) has been virtually staged. Motivated Seller!! *Welcome to this spacious Move-in-ready 4 bedroom, 2.5 bathroom home tucked away in the heart of Royal Hills, Winter Haven. The Home has recent upgrades including freshly painted Exterior in 2025, Roof 2024. The entire upper level has been revitalized with well-maintained carpeting while the ground floor showcases ceramic tile throughout. The kitchen contains Sleek granite countertops for that touch of sophistication,Stainless-steel appliances along with bright light fixtures.The home also has a BONUS Room on the ground level - perfect for a Home office or Media Room and a HUGE Fenced backyard. Conveniently situated near US-27, this property offers quick access to interstate travel and shopping centers. Don't let the opportunity slip by to make this beautiful house your next family home

Listing is courtesy of: MILLENNIUM REALTY CENTER LLC (407-843-8996)

Listing Agent: Phabie Terzier (407-692-7452)

Remarks: HUGE PRICE ADJUSTMENT — MOTIVATED SELLER! Welcome to this beautifully, open-concept Sebastian model FULLY FURNISHED and TURNKEY, allowing you to settle in and start enjoying the Lake Ashton lifestyle from day one. Grand, high ceilings immediately draw your eyes to the serene 17th-hole golf view, offering a peaceful backdrop perfect for relaxed living. The living room is anchored by a stunning wood entertainment center with glass display, complemented by plush leather recliners ideal for unwinding or hosting friends. Recessed lighting, neutral tones, and crown molding create a warm, inviting ambiance throughout the home. This home features tile flooring throughout the main living areas, thoughtfully selected furnishings in every room, and a second bedroom equipped with a medical bed for guests or caregiving needs. The gourmet kitchen includes 42" wood cabinetry with crown molding, granite countertops, a stylish backsplash, pendant lighting, Whirlpool stainless steel appliances, and under- and over-cabinet lighting. A washer and dryer are also included for easy, everyday living. The primary suite offers a peaceful retreat with a walk-in closet, dual granite vanities, and a walk-in shower with a corner seat. Triple sliders open to an extended screened veranda, perfect for morning coffee, evening breezes, or simply enjoying the tranquil golf course setting. The Garage is equipped with storage, a golf cart, a leisure bike, and a garage privacy screen, making it easy to embrace the active lifestyle of Lake Ashton. Just unpack and begin enjoying the community, offering two gated entrances with 24/7 guard service and access to two clubhouses featuring a grand ballroom, movie theater, bowling lanes, and on-site dining at Charm City and Eagle Nest. Stay active with amenities including indoor and outdoor pools, fitness centers, racquetball, tennis, pickleball, bocce, shuffleboard, and more.

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

Listing Agent: Candra Alston (407-257-5204)

Remarks: Turnkey Villa in Stonebridge — Low Maintenance Living, Prime Location Step into easy Florida living with this move-in ready 2-bedroom, 2-bath villa in the highly desirable Stonebridge community. With vaulted ceilings, abundant natural light, and an open-concept layout, the home feels bright, spacious, and immediately inviting. The thoughtfully designed split-bedroom floor plan offers ideal privacy for guests, roommates, or a dedicated home office. The primary suite provides a relaxing retreat with a walk-in closet and a spacious walk-in shower. The kitchen is both functional and welcoming, featuring generous counter space, ample cabinetry, and a breakfast bar that flows seamlessly into the main living area—perfect for everyday living or casual entertaining. Major systems—including the roof, HVAC, and water heater—are all approximately 3 years old, giving buyers peace of mind from day one. Step outside and enjoy one of the home’s standout features: direct proximity to the community pool—just steps away for effortless relaxation. Conveniently located near downtown Winter Haven, Legoland, Disney, and major roadways with access to Florida’s beaches, this home is ideal for full-time living, a seasonal retreat, or an investment opportunity. Opportunities like this don’t last—schedule your private showing today.

Listing is courtesy of: VIVA ORLANDO REALTY INC. (407-861-0000)

Listing Agent: Larry King (404-441-5050)

Remarks: Under contract-accepting backup offers. Experience comfort, style, and thoughtful updates in this spacious 5-bedroom, 3-bath home featuring inviting architectural details and functional living spaces throughout. The welcoming entry showcases six stained-glass side windows surrounding the front door, complemented by a large display window above that fills the foyer with natural light. The open-concept kitchen offers abundant space for gathering and entertaining, complete with a walk-in pantry and seamless flow into the main living areas. A separate dining room provides additional flexibility for formal meals, celebrations, or everyday use. All bathrooms have been tastefully remodeled and updated with modern finishes. The primary suite includes a private en suite bath with a separate water closet for added convenience and privacy. Sliding glass doors lead to a generously sized backyard enclosed with durable vinyl fencing—ideal for outdoor enjoyment, recreation, or entertaining. The outdoor space is further enhanced by mature fruit and ornamental trees, including 2 cherry trees, 1 orange tree, 1 lime tree, and 1 fig tree, creating a beautiful and functional backyard setting. Additional features include a 2-car attached garage and spacious accommodations throughout the home. Don’t miss the opportunity to make this beautifully updated property your next home—schedule your private showing today!

Listing is courtesy of: EPIQUE REALTY, INC. (888-893-3537)

Listing Agent: Rob Bermes (630-915-2686)

Remarks: One or more photo(s) has been virtually staged. Welcome to a place where everyday life feels like a getaway. Set along the peaceful shores of Lake Jessie, part of Winter Haven’s renowned Chain of Lakes, this lakefront retreat is more than just a home, it’s a lifestyle defined by water, sunshine, & unforgettable experiences. Start your mornings with breathtaking sunrises shimmering across the lake, coffee in hand from your private dock or patio. Spend your days exactly how you choose, cruising the Chain of Lakes by boat, casting a line in some of Central Florida’s best freshwater fishing, or enjoying world-class watersports like skiing, wakeboarding, and paddleboarding right from your backyard. With nearby slalom courses and open water, this is truly a paradise for water enthusiasts. Lake Jessie is especially cherished for its tranquil atmosphere, offering a rare sense of calm while still being full of life. One of its most unique features is the seaplane activity, where you can watch planes gracefully land and take off across the water, an experience that never gets old and adds to the charm of lakeside living. Nature lovers will also appreciate the frequent sightings of all kinds of birds and other beautiful wildlife. The home itself offers a thoughtfully designed single-story layout with over 1,800 square feet, featuring 3 bedrooms and 3 bathrooms. An open-concept living space is filled with natural light and showcases stunning lake views, while a split-bedroom design provides comfort and privacy. A private in-law suite with its own entrance adds flexibility for guests, multi-generational living, or additional income potential. This residence offers plenty of parking space with it's oversized driveway and an additional carport providing covered parking as well. The home has been updated with modern finishes and includes a metal roof installed in 2019. This home would make a perfect full time residence, investment property or second home. Beyond the water, the location is just as appealing. You’re right around the corner from a brand new Publix store and minutes from the heart of Winter Haven, where you’ll find charming local restaurants, shops, parks, and community events. Legoland Florida Resort is just a short drive away and there is convenient access to both Tampa and Orlando, so world-class attractions, dining, and entertainment are always within reach. Whether you're seeking adventure, relaxation, or a smart investment, this Lake Jessie property delivers it all, offering the rare opportunity to live, play, and unwind in one of Florida’s most iconic lakefront settings. Book your showing today!

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

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

Remarks: Welcome to Vienna Square, a beautifully maintained 55+ gated community offering resort-style amenities and a peaceful, low-maintenance lifestyle. This 2-bedroom, 2-bath villa features 1,231 sq ft of comfortable living space with an open-concept layout and an inviting Florida Room equipped with its own portable A/C unit—perfect for year-round enjoyment. Inside, the home offers a bright living and dining area, a well-appointed kitchen, and a split bedroom layout for privacy. The Florida Room adds valuable extra space for relaxing, hobbies, or entertaining. Located in a quiet, established neighborhood, residents enjoy access to a clubhouse, tennis courts, community pool, hot tub, movie room, billiards room, fitness center, and a full calendar of weekly social activities. The HOA provides exceptional convenience with yard maintenance included, plus exterior paint every 10 years and roof replacement every 15 years. Just minutes from the brand-new Publix, dining, medical facilities, and all that Winter Haven has to offer, this villa combines comfort, convenience, and an active lifestyle in one of the area’s most desirable 55+ communities. New Roof and Exterior Paint just 2 years ago.

Listing is courtesy of: RE/MAX PRIME PROPERTIES (407-347-4512)

Listing Agent: Tina Bircher (321-228-4267)

Remarks: Discover this stunning 2023-built home in the growing Lucerne Park area of Winter Haven, offering the perfect blend of space, comfort, and modern design. Situated on an oversized lot, this 4-bedroom, 3-bath home with a 3-car garage features over 3,000 square feet of living space with an open and functional floor plan ideal for entertaining and everyday living. The large kitchen overlooks the main living area, creating a bright and welcoming space for gatherings. The spacious primary suite features a walk-in closet and private bathroom, while the additional bedrooms provides flexibility for family, guests, or a home office. Enjoy the oversized backyard with plenty of room to relax, entertain, or create your dream outdoor oasis. Conveniently located near shopping, dining, schools, and just minutes from LEGOLAND Florida Resort, this move-in ready home is a fantastic opportunity in one of Winter Haven’s growing communities.

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

Listing Agent: Jessica Delgado (407-520-0159)

Remarks: Under Construction. This two-story Georgia will definitely be on your mind… This beauty highlights a modern open layout, seamlessly integrating a first-floor kitchen with a central island, a dining room and a welcoming family room with patio access. On the same level is a private owner's suite with an attached bathroom. Situated upstairs is a versatile loft for additional shared living space and four secondary bedrooms to provide restful retreats to family members and guests alike. Villa Mar is a masterplan community of new single-family homes. Near Historic downtown Winter Haven. There are lots of shops, restaurants, bike paths, and easy access to nearby highways. Close to Legoland and Bok Tower Gardens. The much anticipated “Villar Mar” community is what you have been looking for. A safe small town feel with convenience.

Listing is courtesy of: LENNAR REALTY (800-229-0611)

Listing Agent: Ben Goldstein (407-310-7677)

Remarks: Owner motivated and ready to negotiate — WOW! This BEAUTIFUL 931 SF 1BR/1BA FIRST-FLOOR condo in Orchid Springs offers stunning lagoon views! Located in the 55+ Granada Building, where at least one occupant must be 55+. IMMEDIATELY AVAILABLE and MOVE-IN READY! Step into an open, airy floor plan with tile throughout, creating a bright and spacious feel. The dining area, living room, and bonus room flow seamlessly together, all overlooking the tranquil lagoon. As an end unit, the living room and bedroom enjoy extra windows with peaceful courtyard views. The bedroom features a walk-in closet plus an additional hallway closet, providing excellent storage. The bathroom includes a custom vanity and a tub/shower combo. A washer and dryer are included, offering added convenience. Additional highlights include assigned parking directly in front of the unit. Perfect for year-round living or a seasonal retreat in a serene, well-maintained community.

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

Listing Agent: Sharon Gastelbondo (863-800-4655)

Remarks: Owner motivated and ready to negotiate — WOW! This BEAUTIFUL 1361SF 2BR/2BA FIRST-FLOOR condo in Orchid Springs offers stunning lagoon/pond views! Located in the 55+ Granada Building, where at least one occupant must be 55+. IMMEDIATELY AVAILABLE and MOVE-IN READY! Step into an open, airy floor plan with tile throughout, creating a bright and spacious feel. The dining area, living room, and bonus room flow seamlessly together, all overlooking the tranquil lagoon. As an end unit, the living room and bedrooms enjoy extra windows with peaceful courtyard views. The primary bedroom features a walk-in closet plus an additional hallway closet, providing excellent storage. Both bathrooms are well-appointed, with one offering a custom vanity and a tub/shower combo. Additional highlights include assigned parking directly in front of the unit. Perfect for year-round living or a seasonal retreat in a serene, well-maintained community.

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

Listing Agent: Sharon Gastelbondo (863-800-4655)

Remarks: Winter Haven near the scenic Chain of Lakes, this 5 Bedroom 3 Bathroom home with two Flex Rooms is move in ready and close to everything loved like easy commuting, Grocery Stores, Shopping, Dining, Boat Ramps, Scenic Walking Trails, Legoland Florida Resort, and Beaches just an hour and a half away! Step outside to your private oasis featuring a Caged Saltwater Pool with a Safety Alarm System, perfect for peace of mind. The spacious Gazebo adds a relaxing shaded retreat for outdoor dining, lounging, or entertaining. Unique Bonus Room with a Sound Proofing wall, ideal for Recording Studios, Podcasters, Musicians, Content Creators or any Work from home professionals needing their quiet space. This home shows like new with Fresh interior paint, New Luxury Laminate flooring, Carrara porcelain tile for a sleek modern finish, Bright open concept living spaces and a Spacious Kitchen perfect for gatherings. With this home offering flexibility for Large Families, Multi Generational living or hosting guests comfortably, it is a must see! Schedule your showing soon!

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

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

Remarks: Completely renovated and move in-ready Large 4 bedroom, 2 bathroom house awaits your family! On a desirable corner lot, in a quiet neighborhood. New Roof, New Paint, New Flooring all through the house, New Stainless Steel Appliances, New Kitchen Faucet, Like a New Home!! Master Bath has a walk in closet and Garden Tub and Seperate Shower with a Seat. This home offeres a Separate Dining area and a Office or Playroom. Close to the new Polk Parkway extension, so travel to schools, shopping, restaurants and entertainment is super convenient. Great school district and priced to sell quickly. Call today for a showing!

Listing is courtesy of: AVERY PROPERTIES INC. (863-682-1902)

Listing Agent: Anne Greenhow (863-698-4562)