Winter Haven Homes For Sale & Real Estate - 922 homes

Remarks: Welcome to this stunning Bradley floorplan, located in the highly sought-after community of Willowbrook near a beautiful golf course in Winter Haven, FL. This spacious 4-bedroom, 2-bath home offers 1,625 square feet of living space, and provides excellent curb appeal in it's elevation. Inside, you'll 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. This home is ideally situated just minutes from the scenic Port 27 and downtown Winter Haven, making it convenient for shopping, dining, and entertainment. Additionally, it's only a short drive to Highway 27 and about 20 minutes to I-4, providing easy access to nearby cities and attractions. Don’t miss the chance to own this beautiful home in a prime location—schedule your tour today!

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

Listing Agent: Nancy Pruitt, Pa (352-552-7574)

Remarks: MULBERRY model is located in the highly sought-after community of Willowbrook near a beautiful golf course in Winter Haven, FL. This spacious 4-bedroom, 2 and a half-bath home offers 1,938 square feet of living space, and provides excellent curb appeal in it's elevation. Inside, you'll find gorgeous gray cabinets complemented by sleek quartz countertops in the kitchen, creating a modern, bright atmosphere. The open layout is perfect for family gatherings and entertaining guests. The sample photos included are of the model home and are meant to showcase the craftsmanship and design quality.

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

Listing Agent: Nancy Pruitt, Pa (352-552-7574)

Remarks: Beautiful, well-cared-for 2BR/2BA villa in a maintenance-free 55+ community — ready for a new owner. Single-level, move-in ready home with a bright, open floorplan, remodeled kitchen and stainless steel appliances. Durable LVP flooring (2021) throughout the main living areas and new carpet in the bedrooms. Laundry includes washer/dryer 2021; refrigerator 2025. Security system installed. Major recent system and structural upgrades for worry-free ownership: HVAC 2023; 40-gal water heater 2023; PEX water lines 2024; new carport roof 2024; new power panel & upgraded wiring 2021; attic insulation & interior paint 2021. Ease of living: Enjoy true low-maintenance, single-level living with HOA exterior care, easy parking under the new carport roof, and modern systems that minimize upkeep and unexpected expenses. The thoughtful updates and security system provide peace of mind and allow you to spend more time enjoying community amenities, nearby lakes, dining, and shopping rather than home maintenance. Location and lifestyle: Conveniently close to Publix, dining, and scenic lakes — ideal for active adults seeking convenience and leisure.

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

Listing Agent: Holly Patterson (717-668-9598)

Remarks: Welcome to this well-maintained 2-bedroom, 2-bath home located in the desirable community of Oakwood Estates in Winter Haven. This home offers a peaceful, well-kept neighborhood with a welcoming atmosphere and a beautiful lake view to enjoy. Recent updates include new kitchen and bathroom flooring, new windows, and new interior and exterior doors, along with a roof that is approximately 5 years old, offering added value and peace of mind. No lot rent—ownership includes the land, with only a low monthly HOA fee. Oakwood Estates is a gated 55+ community offering resort-style amenities including clubhouses, heated pools, fitness center, shuffleboard, tennis courts, and a full calendar of activities. Conveniently located near shopping, dining, medical facilities, and major roadways. Schedule your private showing today and experience easy living in this vibrant community.

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

Listing Agent: Jody Pagan (863-604-2367)

Remarks: Big Price Drops and Price to sell. Turn Key House on the North Chain of Lakes. 2023 Roof, 2022 POOL! Welcome to this pristine, beautifully maintained home in the quiet and highly desirable Island Lakes community—where there’s no through traffic and peaceful living comes naturally. This property features a newer roof put on in 2023, a newer in-ground pool put in 2022, and a large backyard shed, offering the perfect blend of comfort, storage, and outdoor enjoyment. Step outside and you’ll fall in love with the vinyl-planked dock that gives you direct access to the Chain of Lakes, making it ideal for boating, fishing, and sunset cruises. Whether you prefer relaxing in the screened-in outdoor area or lounging by the sparkling pool, this home is designed for anyone who loves outdoor living. Inside, the home is in immaculate condition. It offers three bedrooms, including a spacious master suite complete with a walk-in tub for easy washing and added convenience. Every room feels well cared for, move-in ready, and prepared for its next owner to enjoy. This stunning property truly has it all—comfort, water access, serenity, and style. It’s ready and waiting for the next buyer who wants to fully embrace lakeside living.

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

Listing Agent: Keith St. Onge (863-651-1397)

Remarks: Another Great Listing brought to you by Paul Jacques, P.A. EveryThing Real Estate. Gated Community, Like New. Open floor plan. minutes from downtown Winter Haven. Low HOA, you’ll enjoy neighborhood security and amenities without the extra cost. Commuters will love the quick access to Hwy 27, providing an easy drive to area beaches, Orlando’s theme parks, and more. Price To Sell.

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

Listing Agent: Paul Jacques (561-441-9695)

Remarks: S.E. WINTER HAVEN, FLORIDA**HERE YOU OWN YOUR OWN LAND, SO NO LOT RENT**THIS LOVELY 2 BEDROOM 2BATH HOME IS LOCATED IN THE WELL-MAINTAINED GARDEN GROVE OAKS COMMUNITY WITH A LOW $65 MONTHLY ASSOCIATION FEE- **NEW ROOF IN 2022**, **NEW AC IN 2022**, **REPLUMBED IN 2019**, NEW WASHING MACHINE IN 2019, DOUBLE WIDE CARPORT/DRIVEWAY & STORAGE/TOOL ROOM & LARGE LOT. The light and bright kitchen with a breakfast bar & plenty of counter space is open to the living room & dining room. French doors exit from the living room to a side screened patio with vinyl windows. The primary bedroom includes a walk-in closet and an en-suit bathroom. Bedroom #2 has a walk in closet and is convenient to the hall bathroom. Garden Groves Oaks amenities include use of clubhouse, pool, spa, shuffleboard, library, cookout room, & optional RV/boat parking when available. If you wish to participate, the Clubhouse activities can include birthday and anniversary celebrations, dances, water aerobics, billiards & cards. With the low monthly association fee, 2022 roof, 2022 AC and 2019 plumbing pipes, this home is sure to sell soon, so make your appointment to view TODAY!

Listing is courtesy of: JUDY B CLEAVES PROPERTIES INC (863-299-5878)

Listing Agent: Chris Goode (863-287-5454)

Remarks: Under Construction. Discover this stunning brand-new construction 3-bedroom, 2-bath home with an open living space and a convenient 2-car garage, this move-in-ready gem boasts elegant granite countertops in the kitchen for a touch of luxury and everyday functionality. The bright, airy layout offers three spacious bedrooms, two full baths, and a peaceful setting perfect for relaxing or family life—ideal for first-time buyers or those seeking fresh, contemporary Florida living. Minutes from shopping, dining, parks, and the Chain of Lakes, this serene location combines tranquility with easy access to everything Central Florida offers. Don't miss this pristine new build—schedule your private tour today! All measurements and sizes are deemed to be accurate but not guaranteed; any information contained here that is critical to buyers' purchasing decisions must be verified by the buyers. Private financing is available to qualified buyers.

Listing is courtesy of: DALTON WADE INC (888-668-8283)

Listing Agent: Juan Carrion (863-581-6028)

Remarks: Under Construction. Discover this stunning brand-new construction 3-bedroom, 2-bath home with an open living space and a convenient 2-car garage, this move-in-ready gem boasts elegant granite countertops in the kitchen for a touch of luxury and everyday functionality. The bright, airy layout offers three spacious bedrooms, two full baths, and a peaceful setting perfect for relaxing or family life—ideal for first-time buyers or those seeking fresh, contemporary Florida living. Minutes from shopping, dining, parks, and the Chain of Lakes, this serene location combines tranquility with easy access to everything Central Florida offers. Don't miss this pristine new build—schedule your private tour today! All measurements and sizes are deemed to be accurate but not guaranteed; any information contained here that is critical to buyers' purchasing decisions must be verified by the buyers. Private financing is available to qualified buyers.

Listing is courtesy of: DALTON WADE INC (888-668-8283)

Listing Agent: Juan Carrion (863-581-6028)

Remarks: Pre-Construction. To be built. Welcome to Ashton Covey in Winter Haven! Discover the ultimate Florida lifestyle in this stunning community. Perfectly situated just off US Highway 27, your new home offers seamless access to work, outdoor recreation, shopping, dining, and more. Imagine being less than 15 minutes from Downtown Winter Haven, where charming local shops and restaurants await your exploration. Plus, you're just 5 miles from public lake access at Lake Daisy, ideal for a day of boating, paddle boarding, and enjoying the water. The Sandalwood single-family home sets the standard for main level luxury. A convenient family entry welcomes you inside to unmatched space and style. A full bath sits between 2 bedrooms, while a guest suite with full bath is found off the 3-car garage. Use the versatile flex space as a home office. The gourmet kitchen includes a large island overlooking dining space and the family room, ideal for gathering with family and friends. Your luxurious owner’s suite features a double vanity bath and massive walk-in closet, plus private access to the rear lanai. You’ll be stunned by The Sandalwood. 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: Under contract-accepting backup offers. Welcome to resort-style living in the pristine and highly sought-after 55+ gated community of Traditions in Winter Haven, Florida. This beautifully maintained 3-bedroom, 2-bath residence offers the perfect blend of comfort, security, and the Florida lifestyle. From the moment you arrive, the oversized paver driveway and inviting curb appeal set the tone for what awaits inside. The thoughtfully designed floor plan is filled with natural light and features welcoming living spaces ideal for both everyday living and entertaining. The spacious living room is enhanced by a triple sliding glass door that opens seamlessly to the enclosed patio, creating effortless indoor-outdoor flow and allowing natural light to pour into the heart of the home. The private primary suite is a true retreat, offering two generous walk-in closets and a well-appointed en suite bath complete with a relaxing soaker tub, separate shower, and dual vanities. Peace of mind comes standard with a buried propane tank that powers a Generac whole-home generator — ensuring uninterrupted comfort even when others are without power. The roof was replaced in 2025, the exterior was freshly painted in 2024, and the home is equipped with a Carrier HVAC system installed in 2021, enhanced by an Aprilaire electric air cleaner for advanced whole-home air purification. A true highlight of the property is the expansive 26x9 enclosed porch spanning the entire rear of the home. Surrounded by walls of windows that flood the space with natural light and offer peaceful views of the lush greenery beyond, this bright and inviting retreat feels like an extension of the living area. With access from the living room, dinette and the primary suite, it is the perfect place to enjoy your morning coffee, unwind with a book, or host friends while taking in Florida’s beautiful weather year-round — all from the comfort of your own private sunroom. Traditions is more than a neighborhood — it’s a lifestyle. The community offers a true resort-style experience designed for both activity and relaxation. At the heart of the community is a beautifully appointed clubhouse featuring a grand ballroom for events and celebrations, a billiards room, library, fitness center, and a vibrant calendar of social activities that keep residents engaged year-round. Outdoors, residents enjoy a sparkling resort-style pool overlooking the lake, creating a stunning waterfront backdrop for relaxation, along with tennis courts and beautifully maintained grounds that enhance the community’s active yet serene atmosphere.

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

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

Remarks: This beautifully updated move-in-ready home sits in a quiet, established community on Lake Dexter, one of Winter Haven’s pristine spring-fed lakes. The neighborhood offers an exceptional lifestyle with private access to a residents-only boat ramp, a sparkling saltwater community pool, and a serene waterfront park complete with a fishing dock, gazebo, playground, and shady green space to enjoy year-round. It’s a rare setting—peaceful, well-maintained, and so close to everything that you can even walk to Legoland. Inside, the home feels bright, airy, and inviting, thanks to thoughtful updates and fresh finishes throughout. The layout is comfortable and functional, featuring a spacious primary suite, two additional bedrooms, and two full bathrooms. The third office or bedroom sits just off the kitchen and is framed by French doors, making it the perfect space for a home office, guest room, or flex space to fit your lifestyle. The seller has invested in quality improvements, including a brand-new roof, fresh interior and exterior paint, a new electric water heater, a full water-softening system, updated light fixtures and hardware, refreshed landscaping, a newly rescreened back patio, and recent servicing of both the AC and irrigation systems. The main living areas feature attractive luxury laminate flooring, adding warmth and style, while the screened back porch provides a quiet, private place to relax overlooking the neatly manicured yard. Winter Haven’s central location between Tampa and Orlando puts major attractions, beaches, airports, and dining just a short drive away, making this an ideal full-time residence or a low-maintenance Florida getaway. This charming home truly checks all the boxes for comfort, convenience, and easy Florida living. All measurements are approximate and should be verified by the buyer or buyer’s agent.

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

Listing Agent: Emily Ward (863-632-1865)

Remarks: Under contract-accepting backup offers. Under Construction. UNDER CONSTRUCTION:Welcome to the Residences at Winter Haven, a new single-family community focused on high-quality construction and modern design. This Key West model features a spacious three-bedroom, two-bathroom layout, centered around an open-concept living area. The interior is highlighted by premium finishes, including vinyl flooring and kitchen island with a fullwaterfall countertop. Large glass sliders lead out to a covered lanai, extending the living space and emphasizing a bright and functional environment.

Listing is courtesy of: KELLER WILLIAMS REALTY AT THE LAKES (407-566-1800)

Listing Agent: Rodrigo Gomes De Almeida (407-837-8173)

Remarks: One or more photo(s) has been virtually staged. PRICE IMPROVEMENT! SELLER MOTIVATED! Completed in 2020 and ready for immediate occupancy, this property blends modern construction with thoughtful recent upgrades. Notable features include a brand-new roof installed in 2023, fully paid solar panels, a freshly painted interior, and professionally serviced and cleaned air ducts, all contributing to energy efficiency and average utility costs of approximately $85–$100 a month. The home is equipped with smart home technology and constructed with concrete block on both the first and second floors, offering added durability and peace of mind. Inside, the kitchen opens naturally to the main living spaces, creating an inviting layout for everyday living and entertaining. A future flooring update provides an easy opportunity to personalize the space. Bedrooms are generously sized, with the primary suite located upstairs, and a fully fenced backyard enhances privacy and functionality. Ideally positioned within the community, the home is just a short walk to the mailbox, pool, and playground, with convenient access to shopping, dining, grocery stores, major roadways, just a short drive to LEGOLAND® and less then one hour from Walt Disney World.

Listing is courtesy of: KELLER WILLIAMS ADVANTAGE REALTY (407-977-7600)

Listing Agent: Kristin Duncan (407-274-5911)

Remarks: Under contract-accepting backup offers. 7167 Summit Dr, Winter Haven, FL 33884 is a beautifully updated 3-bedroom, 2-bath home located in a peaceful Winter Haven neighborhood. Features include ceramic tile in the main living areas, with a renovated kitchen with granite countertops, spacious light-filled bedrooms, and a flexible den/family room. Recent updates include a new in-ground screened pool and Central AC installed in April 2024, new water heater, and a paid-off solar panel system installed in 2021, offering added energy efficiency and long-term savings. The home has also been freshly painted inside and out, including the fence and garage floor. The fenced backyard and 2-car garage add to the home’s appeal. Conveniently located near shopping, restaurants, hospitals, schools, and major routes to Orlando and Tampa. Low HOA of only $260 per year. Showings by appointment only.

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

Listing Agent: Lorena Alvarez Cordero (863-412-9288)

Remarks: FIXER-UPPER OR INVESTORS. Priced accordingly. 2 Bedroom 1 bath- Excellent for rental property. Attached carport and large back yard. NO HOA! Located close to schools, churches, and shopping. Cash offers only with buyer paying title insurance and doc stamps.

Listing is courtesy of: CENTURY 21 WATSON & MYERS REALTY (863-324-1000)

Listing Agent: Sharon Watson (863-557-4800)

Remarks: Rare opportunity to own a spacious two-story home in the highly sought-after Villamar community—homes like this don’t last long. Designed with an open-concept layout perfect for today’s lifestyle, this home offers a seamless flow from the kitchen—featuring quartz countertops, modern appliances, refrigerator, and breakfast nook—into a large, inviting great room ideal for entertaining. Upstairs, retreat to a private primary suite with walk-in closet and en-suite bath complete with dual vanity and tiled shower, along with three additional bedrooms, a full bath, and the convenience of second-floor laundry with washer and dryer included. Enjoy modern living with built-in smart-home features including a Ring Video Doorbell, smart thermostat, keyless entry, and DEAKO switches. Located in Villamar, residents enjoy access to resort-style amenities including a pool, clubhouse, playground, dog park, scenic walking paths, ponds, and lush green spaces. Additional highlights include professional landscaping, a covered entry porch, architectural shingles, and a builder warranty for added peace of mind.

Listing is courtesy of: UNITED REALTY GROUP INC (954-450-2000)

Listing Agent: Keisha Weir (754-204-5431)

Remarks: This charming 2-bedroom, 2-bath condo offers the perfect blend of comfort and convenience with a layout designed for effortless living. Enjoy a spacious living area, light-filled interiors, and a private outdoor space perfect for morning coffee or evening wind-downs. Located just minutes from Winter Haven’s famous Chain of Lakes, local dining, shopping, and everyday essentials, this is the ideal spot for year-round living, a seasonal retreat, or a smart investment. Low maintenance. Prime location. Relaxed lifestyle. *This home can be purchased with NO INCOME VERIFICATION*

Listing is courtesy of: ENGEL & VOELKERS LAKELAND (863-412-6633)

Listing Agent: Donna Fiore (904-228-0198)

Remarks: Welcome To Hartridge Hills!! This Gorgeous Gated Community is one of Polk County's Hidden Treasures. An established and well maintained community of charming custom homes, each one uniquely it's own. Nestled between Lake Pansy and Lake Hartridge, this community offers boat lovers their own private boat ramp with access to the Chain of Lakes. This community also has been home to many pilots over the years and is conveniently located beside the Winter Haven Airport and only minutes to Publix and all major medical facilities making this community a perfect location. Situated on a corner lot, this well built home by Ernie White is a split plan offering 3 bedrooms & 2 baths plus a den or office space. The dining room, living area and bedrooms have new luxury vinyl. There is High ceilings throughout, crown molding, updated granite in the kitchen and bathrooms. The roof was replaced in 2017. HOA fee's include lawn care and the irrigation system is on a small well, saving you money on your water bill! Grab your favorite beverage & Relax and Enjoy the water views on your enclosed back lanai. Come check out this beautiful property, You'll love being a part of this quaint community!!

Listing is courtesy of: PREMIER HOMES AND REAL ESTATE (863-937-8942)

Listing Agent: Christy Smith (863-409-8709)

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)