Winter Haven Homes For Sale & Real Estate - 927 homes

Remarks: Welcome to this stunning 4-bedroom, 3-bath split floor plan home with tile flooring throughout. The open kitchen features a breakfast bar, brand-new stainless steel appliances, and plenty of storage. You’ll love the formal living room and a dedicated laundry room. Sliders from both the master suite and living room lead to a peaceful lanai. The master bath boasts dual sinks, a garden tub, and a separate shower. Plus, one of the bathrooms conveniently opens to the lanai. The lanai floor and garage floor was recently painted for that added style. The home is located in Winter Haven in between Orlando and Tampa close to all of the amenities you would need. Don’t miss this gem!

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

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

Remarks: Great investment opportunity! Tenant-occupied property in a central location with strong rental demand. Short sale subject to lender approval. Sold as-is, no repairs. Do not disturb tenants. No seller/creative financing.

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

Listing Agent: Miraya Lane, Pa (407-969-5204)

Remarks: One or more photo(s) has been virtually staged. One or more photos have been virtually staged. Charming 1920s home for sale in Winter Haven, offering a rare blend of historic character and functional living space in a highly desirable Central Florida location. This move-in ready home welcomes you with a bright tiled foyer, featuring a spacious coat closet and direct access to a front bedroom, ideal for a home office, guest room, or flex space. The main living and dining areas showcase original hardwood flooring and provide an open, inviting layout perfect for both everyday living and entertaining. The kitchen comes fully equipped with refrigerator, range, microwave, and dishwasher, delivering convenience and efficiency for modern living. This split-bedroom floor plan enhances privacy, with the primary suite positioned separately from the secondary bedroom. Just outside the primary bedroom, a versatile bonus area offers flexibility for a home office, nursery, gym, or creative workspace. A rear Florida room adds valuable additional living space and provides direct access to the driveway, creating an ideal setting for relaxing, entertaining, or enjoying Florida’s indoor-outdoor lifestyle. Situated on an R-3 zoned property, this home presents potential opportunities for investors, developers, or buyers seeking flexibility. Buyers are encouraged to verify all zoning and future use possibilities with the City of Winter Haven. Located near shopping, dining, parks, and the renowned Chain of Lakes, this property offers convenient access to boating, recreation, and everything that makes Winter Haven real estate so desirable. Schedule your showing today and explore the potential of this unique Florida home.

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

Listing Agent: Michael Hochadel (863-604-0018)

Remarks: Under contract-accepting backup offers. Lovely 3-bedroom, 2-bath home with a 2-car garage located in the gated golf course community of Lake Bess Country Club in sunny Winter Haven, FL! Perfectly situated on the 9th fairway, this home offers breathtaking golf course views with no rear neighbors—providing both privacy and a serene backdrop. From the moment you arrive, you’ll appreciate the upgraded builder features, including a beautiful tile roof, separate garage entries, and lush, mature landscaping. Just a few doors down from the clubhouse and community pool, the location within the community is ideal. Step inside to cheerful, light-filled interiors with a welcoming open view straight through to the backyard. The thoughtfully designed floor plan includes a formal dining room, a spacious living area with vaulted ceilings, and a separate kitchen dinette complete with a built-in hutch. The screened lanai is the perfect place to enjoy Florida living year-round while taking in the peaceful golf course scenery. The oversized primary suite is privately located and features its own sitting area or study, creating a true retreat. The en suite bathroom offers a soaking tub, separate shower, water closet, and dual sinks in one large vanity, along with a spacious walk-in closet with ample storage. Elegant molding details throughout the home add a touch of sophistication. The kitchen is a chef’s dream, showcasing warm wood cabinetry, tile countertops, a coordinating backsplash, stainless steel appliances, and a built-in wine rack for added charm and functionality. On the opposite side of the home, you’ll find two spacious guest bedrooms and a well-appointed guest bathroom full of character. The indoor laundry room is conveniently located just off the kitchen and leads to the garage, which features a separate single garage door for added convenience. Additional updates include a new HVAC system (2024), and the washer and dryer are included with the sale. Monthly fees cover lawn maintenance (mowing, shrub trimming, fertilization, and weed control), access to the community pool and clubhouse, plus unlimited golf and use of the driving range—offering exceptional value and a true resort-style lifestyle. Conveniently located just minutes from Legoland, the interstate, Tampa and Orlando airports, Disney attractions, shopping, dining, medical facilities, and the Chain of Lakes—perfect for boating, fishing, or simply relaxing. This well loved home offers comfort, convenience, and incredible views—schedule your private showing today!

Listing is courtesy of: COLDWELL BANKER REALTY (863-687-2233)

Listing Agent: John Manibusan (863-307-2792)

Remarks: Welcome to this stunning 3 bedroom, 3 bathroom lake front pool home offering gorgeous views of Lake Ruby. Set on a prime waterfront lot, the property includes an oversized 3-car garage and a private boat dock complete with an automated boat lift, making it ideal for boating and lakefront living. Designed with entertaining in mind, the open layout seamlessly blends indoor and outdoor spaces. Sliding glass pocket doors open to a spacious lanai with a screened-in pool and spa, while a remote-controlled awning provides extra shade for relaxing afternoons or gatherings with friends and family. The master suite is a true retreat, featuring a luxurious bathroom with dual sinks, stone countertops, a garden tub, and a walk-in shower. The kitchen is equally impressive with granite countertops, a breakfast bar, and newer appliances. Additional features throughout the home include vaulted ceilings, crown molding, custom window treatments, and blinds that add style and sophistication. This home combines comfort, elegance, and waterfront living all in one.

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

Listing Agent: Eric Chastain (863-224-2745)

Remarks: Located in the highly sought-after gated community of Lakewood, this beautifully maintained home offers 4 bedrooms and 3.5 bathrooms, set on a lush, manicured lot with mature trees and attractive landscaping. Inside, you’ll find rich wood flooring throughout the spacious living and dining areas, as well as the kitchen and family room—perfect for both everyday living and entertaining. A standout feature is the expansive 480 sq ft detached game room, included in the total living area, complete with a full bathroom and generous closet space—ideal for conversion into a private guest house, in-law suite, or home office. The primary suite boasts a recently renovated en-suite bathroom and direct access to the large screened lanai and pool area, creating a relaxing retreat. Major updates include a roof replacement in 2017. This exceptional property offers space, flexibility, and charm—don’t miss your opportunity to make it yours!

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

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

Remarks: Welcome to 5445 Chandler in Winter Haven—a great opportunity for buyers looking to add their own personal touch! This home offers generous square footage and plenty of living space, giving you room to spread out, entertain, or reimagine the layout to fit your needs. The property has already seen some key updates, including a brand-new roof and fresh interior paint, providing a solid foundation for future improvements. Inside, you’ll find a functional layout with large living areas and ample space, making it ideal for those seeking both comfort and potential. While the home could use some additional updates and TLC, it presents an excellent chance for homeowners or investors to build equity and truly make it their own. Conveniently located near shopping, dining, and Winter Haven’s beautiful lakes, this property offers both space and opportunity. If you’re looking for a home with room to grow and the ability to add value, this is one you won’t want to miss!

Listing is courtesy of: TRANSCEND REALTY (407-518-7653)

Listing Agent: Jacob Hara (407-933-5478)

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: Welcome to this well-maintained home located in the heart of Winter Haven! This property is in great condition and offers a comfortable, move-in ready opportunity for homeowners or investors alike. The home features a fully fenced yard, perfect for pets, outdoor gatherings, or added privacy. Enjoy a functional layout with plenty of natural light and a welcoming atmosphere throughout. Conveniently located near shopping, dining, schools, and major roadways, this property provides both comfort and accessibility. Whether you’re looking for a primary residence or an investment opportunity, this home is a must-see!

Listing is courtesy of: STACEY TOWNS REALTY LLC (863-422-1585)

Listing Agent: Carmen Montes (863-242-3698)

Remarks: This well-maintained 4-bedroom, 3-bathroom pool home is located in the sought-after gated community of Tuscany at Winterset, offering both comfort and style in a prime setting. Inside, you’ll find an inviting layout highlighted by solid surface countertops, elegant tray ceilings, and detailed crown molding that adds a refined touch throughout the living spaces. Major updates provide peace of mind, including new windows (2025), a newer roof (2021), kitchen remodel (2023) and an updated HVAC system (2023). Step outside to enjoy the brick-paved driveway and your own private pool (2020)—perfect for relaxing or entertaining. The property also features a dedicated well for irrigation, helping maintain the landscaping efficiently. This home combines thoughtful upgrades, functional features, and a desirable location—an excellent opportunity in one of the area’s most desirable gated communities.

Listing is courtesy of: CRAIG BURKE REAL ESTATE GROUP, LLC (863-899-5010)

Listing Agent: Tony Insua Jr. (863-221-0656)

Remarks: Welcome to 814 Turner Lane, a beautifully upgraded Hayden model by D.R. Horton located in the heart of Winter Haven! ?? This spacious two-story home offers 5 bedrooms, 3 full bathrooms, and over 2,500 sq. ft. of living space, making it the perfect choice for families or anyone seeking extra room to spread out. Built with quality craftsmanship and thoughtful design, the Hayden model is known for its open-concept layout, versatile bonus spaces, and modern finishes. Step inside to find a bright and inviting interior featuring luxury upgrades throughout, including stylish flooring, designer light fixtures, and premium finishes. The chef’s kitchen boasts granite countertops, stainless steel appliances, a large center island, and an expansive walk-in pantry, seamlessly connecting to the dining and living areas for effortless entertaining. A convenient downstairs bedroom and full bath are perfect for guests, while the second floor offers a private owner’s suite with an en-suite bathroom and a spacious walk-in closet. Upstairs, you’ll also find a versatile loft, perfect for a home office, playroom, or media space, plus three additional bedrooms and a full bath. Outside, enjoy your private backyard, ideal for relaxing or creating your own outdoor oasis. The home is in a growing community with easy access to major highways, shopping, dining, schools, and local attractions. Whether you’re upsizing, investing, or looking for a move-in-ready home with modern upgrades, this Hayden model is a rare find! Don’t miss your chance to own a like-new, thoughtfully upgraded home in beautiful Winter Haven,schedule your private showing today!

Listing is courtesy of: KELLER WILLIAMS LEGACY REALTY (407-855-2222)

Listing Agent: Rafael Ortiz Pena (407-371-8773)

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: Under contract-accepting backup offers. ****PRICE IMPROVEMENT**** This home presents an exceptional opportunity to own in one of Winter Haven’s most desirable 55+ communities. This beautifully maintained 2-bedroom, 2-bath home offers the perfect blend of comfort, privacy, and effortless Florida living. Step inside to a bright, open-concept layout where the living and dining areas flow seamlessly into the kitchen—creating an inviting space ideal for both everyday living and entertaining. Large windows flood the home with natural light, highlighting the clean, well-kept finishes throughout. What truly sets this property apart is the oversized fenced backyard and extended pavered screened-in porch—a rare find in the community. This private outdoor retreat provides unmatched space and flexibility. Whether you have pets, enjoy gardening, or simply value extra room to unwind, this backyard delivers both privacy and possibility. The expanded screened porch feels like a true extension of the home—perfect for outdoor dining, hosting guests, or enjoying peaceful mornings and relaxing evenings in comfort. The primary suite offers a tranquil escape, complete with a walk-in closet and glass-enclosed shower. A spacious secondary bedroom provides versatility for guests, a home office, or hobby space. Thoughtfully designed and move-in ready, this home allows for low-maintenance living so you can fully enjoy the lifestyle you deserve. Residents of Traditions at Lake Ruby enjoy resort-style amenities including a 19,000-square-foot clubhouse, heated pool and spa, fitness center, tennis and pickleball courts, scenic walking trails, and private lake access to Lake Ruby—all just minutes from shopping, dining, and medical facilities. With its recent price improvement, exceptional outdoor space, and prime location, this home stands out as one of the best values in the community. Schedule your private showing today before this opportunity is gone.

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

Listing Agent: James Barris (863-258-6321)

Remarks: Quick Move-in! Introducing Villa Mar in Winter Haven, Florida. Master-planned amenities including a pool with cabana that is walking distance from your home, a playground, and shaded seating area. Highway 27, less than 10 minutes away, has everything you are looking for. Grocery stores, movie theaters, shopping centers, golf courses, restaurants, and so much more. The Windermere single-family home is where you want to be. Step in from the 2-car garage and enjoy the good life. Find it in the large family room, where smiling faces greet you and delicious smells fill the gourmet kitchen. Share stories around the island or outside on the lanai. The 1st floor also features a study. Upstairs, 3 bedrooms and a full bath provide privacy while a loft adds extra entertaining space. Your deluxe owner’s suite includes double vanities, a seated shower and a walk-in closet, making The Windermere can’t-miss. All Ryan Homes now include WIFI-enabled garage opener and Ecobee thermostat. **Closing cost assistance is available with use of Builder’s affiliated lender**. DISCLAIMER: Prices, financing, promotion, and offers subject to change without notice. Offer valid on new sales only. See Community Sales and Marketing Representative for details. Promotions cannot be combined with any other offer. All uploaded photos are stock photos of this floor plan. Actual home may differ from photos.

Listing is courtesy of: MALTBIE REALTY GROUP (813-819-5255)

Listing Agent: Bill Maltbie (813-819-5255)

Remarks: What a find! Cute as a button, historic charm with some nice updates. From the welcoming front porch to the massive fenced back yard, complete with dog washing station, this is a cozy spot to call home! Love the original hardwood floors, open bright kitchen, and character such as built ins. Roof is less than 10 years old, and the sellers have updated the HVAC including adding a mini split to the main bedroom for those who like it extra cold at night. Plenty of parking and extra storage outside as well...check this one before it gets away!

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

Listing Agent: Paula Shields (863-581-1498)

Remarks: Beautifully renovated property in an excellent and highly desirable location. This home features modern finishes throughout, including a stunning quartz kitchen countertop and brand-new appliances. Conveniently located near hospitals, medical offices, major avenues, schools, restaurants, and shopping centers. Its strategic location offers great versatility, making it ideal for both residential living and potential commercial use. A rare opportunity to own a fully updated property in a prime area.

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

Listing Agent: Graceshaly Collazo (939-441-3991)

Remarks: One or more photo(s) has been virtually staged. SEE THIS QUICKLY! This 3BR/2BA mfg home located in SE Winter Haven is in a NO HOA neighborhood with lake access, has a NEW ROOF in 2023, NEW HVAC 2024, and it has been REPIPED. This is an open floor plan with large bedrooms that all have walk in closets, vaulted ceilings, an inside laundry with included LG front load washer and dryer, a spacious kitchen, separate dining room and a huge great room! Accessibility improvements have been made with the remodeled master bathroom including a large shower, along with a comfort height toilet and grab bars which are in both bathrooms. Outside there is an access ramp, a carport for covered parking, two utility buildings and a fenced backyard. There is a good sized porch with plenty of room for a grill and to enjoy relaxing. Located on a cul-de-sac there is no thru traffic. SE Winter Haven is close to LEGOLAND, Highway 27, shopping, dining, medical, schools and more.

Listing is courtesy of: QUINN & COMPANY REALTORS, LLC (863-412-2287)

Listing Agent: Susan Rohlfing (863-557-7059)

Remarks: One or more photo(s) has been virtually staged. Welcome to this stunning Floorplan, located in the highly sought-after community of Willowbrook near a beautiful Golf Course in Winter Haven, FL. This spacious 4-bedroom, 3-bath home offers 2110 sq feet of living space and provides excellent curb appeal in its elevation. Inside, you will find gorgeous White cabinets complemented by sleek quartz countertops in the kitchen, creating a modern, bright atmosphere. Tile flooring runs throughout the wet and common areas, offering durability and easy maintenance. The open layout is perfect for family gatherings and entertaining guests.

Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)

Listing Agent: Cindy Sapp (352-516-2843)

Remarks: Welcome to this beautifully maintained two-bedroom, two-bathroom townhome with a versatile flex space, perfectly situated in one of Winter Haven's most desirable communities. As you step inside, you’ll be greeted by soaring 16-foot ceilings, an open floor plan filled with natural light, and tasteful finishes that create an inviting atmosphere. Just off the entry, a spacious guest bedroom with an attached full bath offers comfort and privacy, while the primary suite is tucked away at the back of the home, complete with serene views and an oversized 12’ x 5’ walk-in closet. A set of double pocket doors leads to the flexible bonus room, ideal as a third bedroom, home office, den, or even a formal dining room to fit your lifestyle. The kitchen and living areas flow seamlessly together, making entertaining easy and everyday living a joy. Step outside to enjoy the well-kept community, where a sparkling pool overlooks the lake, and a private fishing pier adds to the charm of the neighborhood. The HOA takes care of exterior building and roof maintenance, landscaping, cable, and internet, allowing for truly low-maintenance living. With recent updates including exterior paint in 2025, new appliances in 2021, plus the roof, HVAC, water heater, and bedroom flooring replaced in 2018, this home offers peace of mind and modern comfort. Conveniently located near world-class attractions, shopping, and dining, this townhome is the perfect blend of comfort, convenience, and lifestyle. Don’t miss the opportunity to make this exceptional property your new home in Central Florida.

Listing is courtesy of: KELLER WILLIAMS CLASSIC (407-292-5400)

Listing Agent: Nancy Lezotte (407-907-7671)

Remarks: Beautiful home featuring 3 spacious bedrooms and 2 full bathrooms, with a large backyard and no rear neighbors for added privacy. Located in the growing city of Winter Haven, this property is surrounded by new commercial development and is just minutes from schools and hospitals. Conveniently located only 5 minutes from US Hwy 27. Enjoy a low HOA of just $30/month and a community with no CDD fees. This home offers the perfect setting to create lasting memories, whether it’s weekend BBQs in the backyard, family gatherings, or simply relaxing evenings under the Florida sky. With plenty of space to entertain and unwind, this property is ideal for both everyday living and special moments with loved ones. Don’t miss the opportunity to own this wonderful home make it yours today!

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

Listing Agent: Zonybeth Gonzalez Rodriguez (863-242-5268)