Winter Haven Homes For Sale & Real Estate - 1006 homes

Remarks: Under contract-accepting backup offers. UPDATED condo. NEW Bathroom Vanity & fresh Paint throughout. Price Improvement & Great opportunity to add your personal style to this 2 bedroom 2 full bath condo in Park Lake. Located on the 2nd floor close to the elevator with tremendous rental returns. Luxury Vinyl flooring in main living area & primary bedroom. Gas range & Water Heater. Ceiling fans throughout...Roof 2021...Washer/Dryer included with private laundry closet. NEW Dishwasher & Gas Stove just installed. NEW 5T 14 Seer AC just installed. Wet Bar...Terrific view from the back of the newly renovated baseball complex. Walking distance to restaurants & NEWLY RENOVATED BASEBALL COMPLEX. View of Lake Lulu with lake access for fishing off the dock. Primary bedroom offers a walk-in closet & natural light. This building offers an elevator & stairs as well as 1 dedicated parking space. Priced to sell & Perfect for Snowbird or Investor!

Listing is courtesy of: FOLIO REALTY LLC (407-917-0241)

Listing Agent: Dora Siler (407-493-4959)

Remarks: Welcome to this beautiful and well-maintained home in the desirable Julius Estates community of Winter Haven! This spacious residence offers a modern open-concept layout, perfect for both everyday living and entertaining. The kitchen features ample cabinet space, a large island, and overlooks the living and dining areas, creating a bright and inviting atmosphere. The primary suite provides a private retreat with a spacious walk-in closet and an en-suite bathroom. Additional bedrooms offer flexibility for family, guests, or a home office. Enjoy the convenience of a two-car garage, indoor laundry room, and energy-efficient features throughout. Step outside to a generous backyard with plenty of space for outdoor gatherings, pets, or future enhancements. Conveniently located near shopping, dining, schools, medical facilities, and major highways, this home offers the perfect combination of comfort, convenience, and value. Whether you're a first-time homebuyer, growing family, or investor, this is an exceptional opportunity to own a move-in-ready home in one of Winter Haven's growing communities. Schedule your private showing today!

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

Listing Agent: Ane Bertol Bertol (407-577-5607)

Remarks: Welcome home to this charming 1 bedroom condo. Enjoy a lifestyle that blends comfort and convience, with everything you need cloSse by-shopping, parks, dining and commuting routes. Inside, you'll find a bright and functional layout with a spacious living area and cozy bedroom. Whether you're a first time homebuyer, downsizing or investor. Schedule your showing today.

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

Listing Agent: Marquita Smith (863-289-3343)

Remarks: Welcome to 3357 Timberline Rd W, located in the charming city of Winter Haven, FL. This exquisite house, a wonderful opportunity to experience comfortable living in a desirable location. The home boasts a timeless design, showcasing a welcoming exterior that hints at the warmth found within. As you step inside, you'll be greeted by well-appointed spaces that cater to both relaxation and entertainment. The layout of this property is thoughtfully designed to provide functionality and style. Experience the convenience of living in a home that meets your needs, whether you're relaxing in your favorite space or hosting gatherings with loved ones. The exterior of the property complements the interior, offering a harmonious balance of indoor and outdoor living. Enjoy all that this beautiful home has to accord in the heart of Winter Haven.

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

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

Remarks: Short Sale. This home is located in Villamar Subdivision in Southeast Winter Haven. It was built in 2022, and it features a nice open concept with split bedroom plan, inside laundry room, and an open kitchen with a large island. The home has ceramic tile and wood flooring throughout for ease of living. The kitchen features stainless steel appliances package with granite countertops. Other features of this home include a two-car garage, vinyl fencing, and beautiful landscaping. The community features a community pool and playground to enjoy!

Listing is courtesy of: BROKERS REALTY OF CENTRAL FLOR (863-294-6773)

Listing Agent: Renee Butler (863-294-6773)

Remarks: Spacious 3-Bedroom Home with Investment Potential Welcome to this beautifully maintained home featuring three generously sized bedrooms, including a primary suite with a walk-in closet, offering ample storage and comfort. The two additional bedrooms each feature built-in closets, perfect for family, guests, or tenants. Enjoy the convenience of two full bathrooms, a bright and open floor plan, and expansive living and dining areas that create the perfect space for entertaining or relaxing. The modern kitchen is both stylish and functional, ready for daily cooking or hosting gatherings. Additional highlights include a 2-car attached garage for secure parking and storage, and ceiling fans in all bedrooms and the living room, ensuring comfort and energy efficiency year-round. The home is also equipped with seamless gutters around the entire house, offering long-term durability and low maintenance. Whether you're looking for a primary residence or a smart investment property, this home checks all the boxes. With its spacious layout, attractive features, and low-maintenance upgrades, it’s a fantastic opportunity for investors seeking long-term value and strong rental appeal. Don't miss out—schedule your showing today and discover the potential this property offers!

Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)

Listing Agent: Debora Ataide (321-946-6727)

Remarks: Virtually Staged. Welcome to this beautifully renovated, MOVE-IN-READY gem nestled on a spacious nearly quarter-acre lot in the heart of Winter Haven! Perfectly situated on a quiet residential street, this stunning 3-bedroom, 2-bathroom home combines MODERN UPGRADES, functional living spaces, and exceptional outdoor privacy with the freedom of NO HOA RESTRICTIONS. From the moment you arrive, you'll appreciate the inviting curb appeal, long concrete driveway, classic brick accents, and convenient one-car carport. The OVERSIZED HOMESITE provides AMPLE PARKING and plenty of room for additional outdoor storage, recreational vehicles, trailers, or future enhancements. Step inside to discover a bright, open-concept floor plan showcasing gorgeous luxury vinyl flooring, fresh interior finishes, stylish NEW LIGHTING, updated ceiling fans, and an abundance of natural light that creates a warm and welcoming atmosphere throughout the home. The thoughtfully designed layout offers comfortable everyday living while providing the perfect space for entertaining family and friends. At the center of the home is a completely redesigned kitchen that is sure to impress. Featuring elegant quartz countertops, NEW SHAKER CABINETRY, a FARMHOUSE SINK, BRAND-NEW STAINLESS STEEL WHIRLPOOL APPLIANCES, and a breakfast bar, this kitchen delivers the modern finishes maintaining excellent functionality and storage. The thoughtfully designed split bedroom floorplan provides privacy and comfort. The spacious primary suite serves as a relaxing retreat with a beautifully updated ensuite bathroom featuring a stand-up shower, quartz countertops, and a stylish vanity. Two additional bedrooms offer flexibility for guests, family members, a home office, fitness room, or hobby space. The secondary bathroom has also been tastefully renovated with contemporary finishes. Convenience continues with a SEPARATE INDOOR LAUNDRY ROOM offering direct access from both the kitchen and carport, making everyday tasks effortless. French doors open to an EXPANSIVE SCREENED PATIO that serves as an extension of the living space, providing the ideal setting for outdoor dining, weekend gatherings, or simply enjoying Florida's year-round sunshine. Beyond the porch, the FULLY FENCED BACKYARD with PREMIUM VINYL FENCING offers outstanding privacy. Whether you envision a future pool, playground, garden, outdoor kitchen, firepit area, or additional storage building, there's plenty of room to make it your own. Additional updates and features including a roof less than 10 years old, a SEPTIC SYSTEM LESS THAN FIVE YEARS OLD, a BRAND-NEW 2026 WATER HEATER, public water service, and a 2011 HVAC system. The extensive renovations mean less maintenance. Location is everything, and this property delivers. Conveniently located near shopping centers, restaurants, healthcare facilities, schools, parks, and everyday conveniences, you'll also be just MINUTES FROM WINTER HAVEN CHAIN OF LAKES, Downtown Winter Haven, Legoland Florida Resort, Lake Hartridge, and numerous public boat ramps, fishing opportunities, and recreational amenities. Easy access to major highways makes commuting to Lakeland, Orlando, and Tampa a breeze. COMPLETELY RENOVATED, packed with MODERN UPGRADES, situated on a LARGE FENCED LOT, and offering the increasingly rare benefit of NO HOA, this exceptional Winter Haven property presents a unique opportunity seeking a turnkey home in one of Central Florida's most desirable and rapidly growing areas.

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

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

Remarks: MOVE-IN READY! Welcome to your dream home in the sought-after Willowbrook North community! This stunning Ranch-style, one-story residence offers effortless living with 3 spacious bedrooms, 2 full bathrooms, and a versatile flex space—perfect for a home office, playroom, or additional living area. You'll fall in love with the modern open-concept layout, featuring quartz countertops throughout, soft-close cabinets and drawers, and smart home features designed for comfort and convenience. Enjoy peaceful mornings and relaxing evenings with serene pond views right outside your front door. Built with quality and style in mind, this home is the perfect blend of elegance and functionality—ready for you to move in and make it your own. Don't miss this opportunity to own a beautifully crafted home in a growing, vibrant community!

Listing is courtesy of: DRB GROUP REALTY, LLC (407-270-2747)

Listing Agent: Adam Schott (407-270-2747)

Remarks: NO CDD Fees • Low HOA • *Lower Taxes • Luxury Heated Pool • Resort-style backyard • Move-In Ready Home. Welcome to this beautifully maintained and gently lived-in upscale home situated on an oversized 70’ wide homesite in a desirable community offering low HOA fees and *lower property taxes. Designed for both comfort and entertaining, this expansive 4-bedroom, 3.5-bath, two-story home has approximately 2,894 sq. ft. of thoughtfully designed living space, including TWO primary suites — one conveniently located on the first floor with a luxury bath and spacious walk-in closet, and a second upstairs primary suite featuring its own full bath and walk-in closet. The first floor also includes a versatile enclosed flex room which can be used as a home office, guest room, or potential 5th bedroom. The second floor has three other bedrooms with walk-in closet and oversized loft about 21'x17'. Step outside into your private resort-style backyard featuring a heated, fully automated full-size pool and spa with premium PebbleTec finish, already prepped for expansion with a concrete footer for future screen enclosure installation, upgraded pavers, large covered lanai, gutters and downspouts for improved drainage, fully fenced yard and extended front porch — creating the perfect Florida outdoor living experience— for entertaining, relaxing, pets, and family gatherings. Inside, the open-concept kitchen is beautifully upgraded with: • premium color cabinets, • oversized island, • stylish backsplash, • single-bowl sink, • granite countertops, • pendant lighting, • and stainless-steel appliances. Additional interior highlights include: • recessed LED lighting throughout, • tile flooring in wet areas, kitchen, hallway, and gathering room, • exterior-vented microwave, • and abundant natural light throughout. This truly move-in-ready home includes: • first-floor family room sofa set with wall-mounted 75” TV, • upstairs loft recliner sofa set with wall-mounted 75” TV, • refrigerator, washer, dryer, and window blinds, • home alarm system, • outdoor security cameras, • video doorbell, • and remote thermostat. Additional peace of mind includes: • transferable Pulte Homes 5/10-year warranty, • and 1 year of complimentary pool maintenance. This home has the perfect blend of luxury, functionality, and convenience in a family-friendly community with a safe small-town feel while remaining close to shopping, dining, everyday amenities and just minutes away from Legoland. READY TO MOVE IN. *Some photos have been virtually rendered.

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

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

Remarks: Turnkey Airbnb opportunity in the heart of Winter Haven! This fully furnished 4-bedroom, 2-bath pool home is perfect for short-term rental income, multi-generational living, or your next investment property. Featuring a flexible multi-generational layout and a suite with its own entrance, the home includes a private in-law suite, creating the ideal setup for guests or extended family. Recent updates include a new roof installed in 2023 for added peace of mind. Inside, you'll find bright and spacious living areas, a functional kitchen with ample cabinet and counter space, and comfortable bedrooms designed for relaxing stays. Outside, enjoy a fully fenced backyard with a private in-ground pool, plenty of room to entertain, and space to unwind. The large driveway and oversized 2-car carport provide ample parking for guests, boats, or multiple vehicles. With no HOA and the property being sold fully furnished, this move-in-ready home offers incredible flexibility as a primary residence, vacation getaway, or income-producing Airbnb. Conveniently located near shopping, dining, schools, and area attractions.

Listing is courtesy of: EXP REALTY LLC (407-706-5000)

Listing Agent: Daniel Betancourt (407-375-9142)

Remarks: This traditional 3-bedroom, 2-bathroom home is located in the established Queens Cove Ph 02 neighborhood. Designed with a functional and classic layout, this residence offers a comfortable living environment perfectly suited for a variety of lifestyles. The heart of the home features a traditional floor plan that provides a clear and smart separation of living spaces. The kitchen is beautifully updated with sleek quartz countertops and Stainless steel appliances, creating a modern and stylish space for meal preparation and entertaining. Situated in a prime location, this home is just minutes away from local essentials, including shopping, dining, and parks. Whether you are searching for a forever home or a smart investment opportunity, this property offers both convenience and potential. Schedule your private showing today!

Listing is courtesy of: ENTERA REALTY LLC (888-216-6364)

Listing Agent: Robert Salmons (888-216-6364)

Remarks: Spacious living plan and Luxurious Kitchen just updated for the top Chef status. As you come in through the covered carport you'll notice the Newly installed flooring that really shines. There are 2 Living Room areas one of which you could close off for a 3rd bedroom. Large Master Bedroom and Bath. Skirting around the home has just been replaced for a new look. Not to mention all of the amenities offered with the community swimming pool, pickleball, tennis courts and putt putt golf course. This property is located on the dog approved residence street, so Fido is in luck. New AC unit was replaced in 2026. You're in close proximity to all the Central Florida attractions. Hurricane/ Tie Down Straps Replaced 2023. Ceiling fans have been updated w/ remotes. UPDATE: New Linoleum flooring has just been professionally installed throughout the entire home to match the kitchen.

Listing is courtesy of: FLORIDA HOMES REALTY & MORTGAGE (904-996-9144)

Listing Agent: Karl Erickson (813-245-6181)

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. 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: LOCKHART & ASSOCIATES INC (863-293-1234)

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

Remarks: The two-story Atlanta Plan has the “WOW-Factor” with four bedrooms, two and a half baths, loft and a two-car garage. This exquisite home offers an open floor plan with great room, dining room, and kitchen with large island. The kitchen features ample counter space, and generous pantry. The casual dining area allows outdoor access to a covered lanai via sliding glass doors. The second floor includes an owner's retreat featuring an owner's bath with large walk-in shower, dual vanity, and spacious walk-in closet. Three additional bedrooms, a bathroom, a spacious loft, and laundry room finish off this beautiful home. This home comes fully equipped with Everything Included Features like new appliances, solid surface countertops throughout and oversized tile flooring in the wet areas. Peace Creek Reserve is a masterplan community of new single-family homes with a beautiful natural creek. Winter Haven is the chain of lakes city, with over 26 linked together by canal. There are lots of shops, restaurants, bike paths. Peace Creek Reserve is what you have been looking for. A safe small town feel with convenience, the perfect place to raise a family.

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

Listing Agent: Omar Andreasen (407-883-2989)

Remarks: Investor-friendly duplex opportunity in Winter Haven offering two separate rental units on a spacious 0.36-acre lot, approximately 15,794 sq ft. This income-producing property features 2,249 sq ft of heated space across two buildings, with a front 3-bedroom, 2-bath unit and a rear 2-bedroom, 1-bath unit. Both units are tenant occupied, creating immediate rental income potential from day one. The property has been previously refurbished and includes new roofs noted in the listing details, central air, electric heat, public water, septic, and washer/dryer plumbing for both units. The rear unit also features its own fenced backyard, offering added privacy and usability for tenants. Located in the established Inwood area of Winter Haven, this property is close to downtown shopping, entertainment, schools, medical facilities, major highways, and a nearby lake with a public park, jogging trail, and playground. With no HOA, two rental units, and a convenient Central Florida location, this duplex is a strong option for investors seeking cash flow, long-term rental potential, or a house-hacking opportunity.

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

Listing Agent: Tyler Gibson Llc (877-366-2213)

Remarks: Under Construction. This charming 4-bedroom, 2-bathroom new construction build features an open floor plan and 1,778 square feet of living space, all while sitting on a .73 acre lot. The spacious great room, with high vaulted ceilings is perfect for family movie nights in, with convenient access to the back patio. The large open kitchen caters to family living as well as entertaining with its lengthy seated bar for that delicious morning breakfast, and is located perfectly in between the great room and dining area. The ample primary bedroom is enhanced by its dual-sink vanity bathroom and walk-in closet featuring a linen closet within. Additionally, the spacious garage provides additional storage and leads directly into the home’s designated laundry space. This home is located in a quiet neighborhood off Winter Lake Rd, close to all of the amenities Lakeland or Winter Haven have to offer! With no HOA, there's room for your boat, RV, or other outdoor vehicles. USDA FINANCING AVAILABLE FOR ELIGIBLE BUYERS, WITH NO MONEY DOWN. CALL TODAY FOR MORE DETAILS.

Listing is courtesy of: PORCHLIGHT HOMES LLC (863-529-3369)

Listing Agent: Angie Reynolds (863-838-1090)

Remarks: Under contract-accepting backup offers. LAKEFRONT LIVING FOR UNDER $200K, MOTIVATED SELLERS SAY BRING US AN OFFER!! Why pay lot rent when you can enjoy the charm and tranquility in this beautifully renovated, Fully Furnished 2 Bedroom/2 Bath 2006 home in Winter Haven! Nestled in the serene, gated 55+ Lakeside Ranch community on Lake Henry. This home is move-in ready and offers a host of modern updates, including New HVAC (2025) and New Roof and All New Windows both replaced in 2024. The home features a spacious living room, a primary bedroom with an ensuite bathroom and walk-in shower, an indoor utility room with laundry and extra storage, and a screened-in porch perfect for relaxing or enjoying breathtaking sunset views. The kitchen is designed for convenience featuring an Island with Breakfast Bar and ample storage. The carport doubles as additional seating or parking space. Lakeside Ranch is a co-op community where the price includes an $11,000 share in the corporation—meaning no lot rent. The LOW MONTHLY HOA Fee that includes Water, Sewer & Garbage. This vibrant community offers an array of amenities, including a clubhouse, heated swimming pool, library, shuffleboard courts, horseshoe area, billiards, a boat launch, and docks on Lake Henry. Residents can also take advantage of scheduled holiday events, arts and crafts classes, exercise programs, card games, and more. For added convenience, the community has a trailer storage area, self-contained water and sewer systems with backup generators. Perfect for year-round residents or snowbirds. Lakeside Ranch Community offers the flexibility to be as active or as relaxed as you desire. With its idyllic location near shopping, dining, and amusement parks, this home offers the best of Florida living. Call today for a private showing and start enjoying the security, serenity, and vibrant lifestyle of this remarkable Lakeside Community!!

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

Listing Agent: Cheryl Brewer (863-224-0045)

Remarks: Short Sale. – PRICED TO SELL! Welcome to this 2022-built 3-bedroom, 2-bathroom home located in the growing Lucerne Park Reserve community of Winter Haven. This newer construction single-story home features a desirable open-concept floor plan, perfect for comfortable everyday living and easy entertaining. The spacious kitchen overlooks the living and dining areas, creating a bright and inviting central gathering space. The primary suite offers a private bathroom and generous closet space, while two additional bedrooms provide flexibility for guests, family, or a home office. Home includes solar panels, offering potential energy efficiency benefits for the new owner. Conveniently located near shopping, dining, schools, and major highways with easy access to Lakeland, Orlando, and surrounding Central Florida areas. Ideal opportunity for first-time buyers, investors, or anyone looking to add value in a rapidly growing area. Short Sale – subject to lender approval. Property sold as-is. MOTIVATED SELLERS!!!

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

Listing Agent: Mariel Espinal (407-921-5868)

Remarks: Under contract-accepting backup offers. Under Contract. Winter Haven Single Family Residential home, 3B/1ba offers a well landscaped Corner Lot. The Interior accommodates Electric AC & natural gas heat. This home still boasts original well maintained kitchen cabinets, eat-in kitchen & gas oven appliances. The Exterior features are Concrete Block Detached storage/workshop 20x14’, covered carport 20x12’, exterior lighting,pvc plumbing, irrigation well/pump, pole barn for RV parking 28x20’, carport, brand new hot water heater, enclosed concrete outside laundry room. This home offers updated plumbing and abundant parking. Pride of Ownership. A must see!

Listing is courtesy of: WATSON & WATSON INC REALTORS (863-294-4149)

Listing Agent: Wendy Gibbs (863-557-5249)

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)