Winter Haven Homes For Sale & Real Estate - 1041 homes

Remarks: Move-in ready and thoughtfully maintained, this home checks every box a new A/C (2025), newer water heater (2021), and a newer tile roof so you can buy with confidence. Step outside to a private, lushly landscaped backyard garden, the perfect setting for morning coffee or evening unwinding, complemented by a bright, spacious Florida room overlooking tranquil lake views. Set in a highly desirable, 24-hour guard-gated community, this 3-bedroom, 2.5-bath home puts resort-style living at your doorstep. From a stunning clubhouse and lakeside pool and spa to tennis courts and a community boat ramp. Whether you crave quiet relaxation or an active, amenity-rich lifestyle, this community delivers it all.

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

Listing Agent: Christopher Gallon, Pa (407-967-9363)

Remarks: Seller is offering a $5,000 Buyer credit. Discover modern living in this stunning newly built 3-bedroom, 2-bath home, where style meets comfort. Bright, spacious bedrooms provides the perfect retreat, while sleek, thoughtfully designed bathrooms add a touch of luxury. The open-concept layout flows effortlessly from the kitchen to the living and dining areas, ideal for entertaining or relaxing. A generous walk-in closet keeps everything organized in style. Step outside to your private, pet-friendly backyard, perfect for play, lounging, or weekend barbecues. With high-end finishes, abundant natural light, and a warm, welcoming vibe, this move-in-ready home is everything you’ve been looking for.

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

Listing Agent: Christopher Gallon, Pa (407-967-9363)

Remarks: Virtually Staged. NEW ROOF in 2024! Beautiful 4-bedroom, 2-bath, two-story home offering just over 1,900 square feet of generous living space. Step inside to discover a freshly painted interior complemented by new flooring throughout. The spacious floor plan features a welcoming living room with a dining area, and a large family room off the kitchen—perfect for both everyday living and entertaining. The kitchen boasts ample counter space, lovely cabinetry, and plenty of storage space. The primary suite is conveniently located on the main floor and includes a private en-suite bathroom with a dual sink vanity, a relaxing garden tub, and a separate walk-in shower. Two additional bedrooms are also located downstairs, while the fourth bedroom can be found upstairs, great for guests. Relax with your morning coffee or host family and friends on the screened rear porch overlooking the fully fenced backyard, providing both privacy and space to enjoy the outdoors. Don't miss the opportunity to make this wonderful home yours—schedule your private showing today!

Listing is courtesy of: ASSOCIATE REALTY (863-618-4000)

Listing Agent: Chrissi Jasso (863-618-4000)

Remarks: Virtually Staged. Welcome to this stunning, nearly new 3-bedroom, 2-bathroom home built in 2023, offering 1,880 total square feet of thoughtfully designed living space in a desirable Winter Haven community. From the moment you arrive, you'll appreciate the fresh landscaping that creates outstanding curb appeal. Step inside to discover a bright, open-concept floor plan featuring tile flooring throughout the main living and high-traffic areas, with luxury vinyl plank flooring providing warmth and durability in each bedroom. The heart of the home is the modern kitchen, complete with solid surface countertops, a spacious center island, stainless steel appliances, and abundant cabinet and prep space—perfect for entertaining or everyday living. Upgraded lighting and contemporary fixtures add a custom touch throughout, while large windows fill the gathering spaces with an abundance of natural light. Whether you're a first-time homebuyer, growing family, or someone looking for a nearly new home without the wait of new construction, this property offers the perfect blend of comfort, style, and convenience. Ideally located in the heart of Winter Haven, you'll enjoy easy access to the city's renowned Chain of Lakes, shopping, dining, parks, medical facilities, and major roadways, all while experiencing the welcoming charm that has made Winter Haven one of Central Florida's most desirable places to call home. Don't miss your opportunity to own this beautifully updated, move-in-ready home—schedule your private showing today!

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

Listing Agent: Jason Stone (863-838-8972)

Remarks: Welcome home to this beautifully updated 3-bedroom, 2-bath residence situated on a spacious corner lot in an established neighborhood with NO HOA! Blending timeless charm with modern upgrades, this move-in-ready home offers comfort, style, and exceptional value. Recent improvements include a new roof, new central heating and air conditioning system, updated flooring, fresh interior and exterior paint, new lighting fixtures, and updated appliances, giving the home a fresh, modern feel from top to bottom. Inside, you’ll find bright and inviting living spaces designed for comfortable everyday living. A heated and air-conditioned sunroom with a full bath provides incredible flexibility and can serve as a second living area, home office, hobby room, guest space, or entertaining area. The home also features a convenient indoor laundry room under central heat and air, adding comfort and functionality. Situated on a generous corner lot, the property offers plenty of outdoor space with a private irrigation well, making it easy to maintain a beautiful lawn and garden while keeping watering costs down. There’s ample room for outdoor entertaining, pets, or future additions. Conveniently located near shopping, dining, schools, and everyday amenities, this beautifully refreshed home combines the character of an established neighborhood with the peace of mind that comes from extensive recent updates. Don’t miss your opportunity to own this move-in-ready gem with space, flexibility, and modern improvements throughout!

Listing is courtesy of: CENTURY 21 MYERS REALTY (863-875-5656)

Listing Agent: Donna Keath (863-838-9389)

Remarks: Welcome home to this beautiful 4-bedroom, 2.5-bath residence offering over 1,900 square feet of thoughtfully designed living space. From the moment you arrive, you'll appreciate the fresh interior and exterior paint completed in July 2025, giving the home a clean, modern look. Inside, you'll find a spacious and inviting floor plan featuring shutters throughout and brand-new bedroom flooring installed in July 2025. The kitchen has been tastefully updated with all-new appliances (2025), including a refrigerator, oven, microwave, dishwasher, and a built-in wine fridge—perfect for everyday living and entertaining. Step outside to enjoy the fully fenced backyard, completed in 2024, offering privacy and plenty of space for pets, play, or gatherings. The enclosed back porch (2024) provides additional year-round living space, ideal for relaxing with your morning coffee or hosting guests. A sprinkler system helps keep the lawn lush and easy to maintain, while newly installed gutters (2025) add to the home's value and functionality. Additional highlights include a spacious two-car garage, generous living areas, and numerous recent upgrades that make this home truly move-in ready. With modern improvements, timeless finishes, and plenty of space for family and friends, this exceptional property is ready to welcome you home.

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

Listing Agent: Curtis Yopp (863-661-2732)

Remarks: Welcome to the Eagle Landing community in Winter Haven, FL. This well-maintained single-family home is move-in ready and waiting for its new owner(s). The open-floor concept creates a comfortable flow throughout the main living areas, while the split floor plan provides added privacy for the primary bedroom and bath with spacious walk-in closet. The kitchen features stainless steel appliances and granite countertops, offering both style and functionality. Additional conveniences include a laundry room, two car garage and low HOA dues, making this home an affordable and practical choice. Experience the charm of small-town living while enjoying the growth and expansion happening throughout Winter Haven. Conveniently located just minutes from Legoland, shopping, dining, and entertainment, and centrally positioned between Tampa and Orlando for easy travel in either direction. Solar panels will be paid off at closing, providing the new owner with the benefit of low electricity bills. The spacious backyard offers room to relax or entertain.

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

Listing Agent: Carla Miro (786-897-4081)

Remarks: Under contract-accepting backup offers. **Price Enhancement** Needs some TLC. Spacious condo with 1 bedroom, laundry inside, bonus patio area and on 1st level. Easy to maintain so you have the flexibility to travel and relax. The kitchen is white and bright and living room/dining combo offers an open floor plan. This home feels comfortable and cozy. This condo comes with an assigned parking spot. Close to restaurants, shopping lakes and a variety of activities. Newer A/C installed in 2022. Note: only stove, microwave & dishwasher convey. Home does not have washer/dryer or refrigerator. There is a laundry room available real close. Needs some TLC. Condo is currently at max 20% capacity to use as a rental property. **HOA is $208.62 + $29.47 = $238.09 until December 31, 2026 due to gas line repay reserve assessment 6/1 - 12/31.**

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

Listing Agent: Tina Mcdonald (989-385-5757)

Remarks: Discover lakeside living at its finest in this spacious 4-bedroom, 2-bath home located in the highly desirable 55+ community of Golf & Lake Estates in Winter Haven. Here, you own both the home and the land—a rare find in this area. Perfectly positioned with Lake Henry as your backyard, this home offers stunning water views from the large living area, where expansive windows fill the space with natural light and frame the peaceful scenery. This well-maintained community features outstanding amenities, including a marina, pool, spa, clubhouse, and a storage lot for RVs or boats. Whether you love fishing, boating, or simply relaxing by the water, this property provides the ideal setting. Enjoy the serenity of lakeside living with the convenience of an active, friendly neighborhood. Don’t miss the chance to call this beautiful lakefront property home!

Listing is courtesy of: GREEN STAR REALTY, INC. (813-598-6841)

Listing Agent: Samantha Conley (813-300-7753)

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

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

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

Remarks: Welcome home to this charming pool home nestled in the heart of Winter Haven! Offering plenty of space for everyone, this home features a versatile bonus room perfect for a home office, playroom, media room, or additional living space to fit your needs. Step outside and dive into your own private in-ground pool, the perfect place to cool off and beat the Florida heat while entertaining family and friends. Conveniently located just minutes from shopping, dining, medical facilities, schools, and everything Winter Haven has to offer, you'll love the combination of comfort and convenience this property provides. Whether you're relaxing poolside, enjoying the flexible interior spaces, or taking advantage of the nearby amenities, this home offers the Florida lifestyle you've been looking for. Don't miss your opportunity to make this beautiful property your own—schedule your private showing today!

Listing is courtesy of: NONA LEGACY POWERED BY LA ROSA (407-270-6841)

Listing Agent: Sara Jones (863-632-2615)

Remarks: Welcome to a home that makes everyday living simple and enjoyable. Located in the established Country Club community, this property offers a practical layout, comfortable spaces, and a setting that supports an easy Florida lifestyle. Inside, you’ll find well-proportioned living areas with plenty of natural light, creating an open and functional feel. The kitchen connects seamlessly to the main living space, ideal for daily routines and casual gatherings. Bedrooms are arranged for privacy, with a primary suite that provides a comfortable place to recharge. The interior bedrooms also feature NEW CARPETS and a double primary bedroom closet space for his and hers. Outdoors, enjoy an above-ground pool with a screened enclosure—perfect for Florida afternoons, weekend gatherings, or low-maintenance relaxation year-round. The yard still offers space for outdoor seating, play, or gardening without excessive upkeep. Conveniently located near shopping, dining, medical facilities, and major roadways, this home offers easy access to everything Winter Haven has to offer, including local lakes and recreation. A solid choice for buyers seeking comfort, convenience, and value in a well-located neighborhood.

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

Listing Agent: Jeremy Ortiz (863-944-5754)

Remarks: Located on a spacious corner lot in the heart of Winter Haven, this income-producing duplex offers an unbeatable combination of location, and long-term potential. One unit is currently rented for $1,300 on a month to month lease. The other unit is currently vacant. Featuring a brand-new roof and easy access to Winter Haven’s famous Chain of Lakes, including Lake Howard and Lake Cannon. Residents can enjoy boating, fishing, and waterfront dining. Ideally situated only about 8 minutes from Downtown Winter Haven, residents can also enjoy local restaurants, shops, entertainment, and community events while still having quick access to major roadways for an easy commute throughout Polk County. The property also offers convenient access to nearby schools, including Inwood Elementary just 2 minutes away, Westwood Middle approximately 4 minutes away, and Winter Haven Senior High around 8 minutes away. Whether you’re looking to expand your investment portfolio or secure a property in one of Central Florida’s fastest-growing lakefront communities, This property has exceptional value with its prime location, recent improvements, and proximity to Winter Haven’s iconic lakes and downtown district.

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

Listing Agent: Corey Ayala (618-638-3273)

Remarks: BACK ON MARKET!! Welcome to the lakefront community of Edgewater Manor! Come see this awesome custom built 2017 4 bed 3 bath corner lot (1/3 ac.) home with fenced backyard! Located just off Cypress Gardens Blvd., this bright, open floorplan includes combo living and dining area, an office, and a spacious kitchen with white wood cabinets and grey granite counter tops, stainless steel appliances, gas stove, and eat-in area. There is a large family room off the kitchen, crown molding throughout the home, vinyl fencing, and much more, including: gas tankless WH, vinyl planking floor everywhere but bedrooms, plantation shutters, double pane low E windows, a screened lanai. There is even a plug for an electric car built into garage wall, and a shallow well for lawn irrigation. Plus, close to Legoland, restaurants, shopping, and the chain of lakes. A great find!

Listing is courtesy of: STORMS REALTY (813-293-4652)

Listing Agent: Steve Storms (813-293-4652)

Remarks: Under contract-accepting backup offers. Virtually Staged. Introducing a beautifully renovated 2-bedroom, 2-bath condo located on the lakefront of Lake Howard in Winter Haven. This top-floor unit is truly turnkey, offering updated flooring, fresh paint, new drywall, new interior doors, updated kitchen cabinets, and modern appliances. Recent upgrades include energy-efficient double-hung windows, a newer A/C system, and a stackable washer and dryer. The top-floor location provides added privacy with no neighbors above, while elevator access makes daily living easy and convenient. Enjoy relaxing lake breezes and beautiful Lake Howard views within this community in addition to the peaceful pool view from the unit. Community amenities include a pool, shuffleboard, and organized activities. Covered parking and onsite storage lockers are also included. This mint-condition condo offers comfort, convenience, and lakefront living with a low condo association fee in a 55 and older setting. A rare opportunity in a desirable Winter Haven location.

Listing is courtesy of: VILLAGE REALTY OF WINTER HAVEN (863-299-6767)

Listing Agent: Joshua Taylor (863-651-5471)

Remarks: Short Sale. SHORT SALE OPPORTUNITY PRICED TO SELL! This is a great opportunity to walk into equity in a newer home. Needs some minor TLC. Lucerne Park Reserve is located in historic Winter Haven only one mile from US-27 providing easy access to major employment centers. The home is located closely to town centers with plenty of restaurant and retail options. Meritage Home is Known for their energy efficient features. Low HOA of $200/year includes community pool and park

Listing is courtesy of: FOUNDATION REALTY GROUP (813-729-6000)

Listing Agent: Dana Cates (813-729-6000)

Remarks: Beautiful lake-view condo in Winterset! This ground-floor 2-bedroom, 2-bath residence offers amazing views of Lake Winterset, part of the renowned Winter Haven Chain of Lakes. The spacious great room features tile flooring, sliding glass doors to the screened porch, and stunning lakefront vistas. Just off the kitchen is a comfortable dining area, creating an inviting space for everyday living and entertaining. The kitchen is beautifully appointed with custom Kraft Maid wood cabinetry, granite countertops, a breakfast bar, and a complete appliance package. The primary bedroom enjoys peaceful lake views and includes plush carpeting with a gel pad, a large 11' X 7' walk-in closet, a ceiling fan, sliding doors to the patio, and an en-suite bath featuring dual sinks, quartz countertops, and an oversized walk-in shower with a seamless glass door. The guest bedroom is generously sized at 13' x 10', offering ample closet space and convenient access to the guest bathroom, which features quartz countertops and tile flooring. The screened porch is the perfect place to relax and enjoy breathtaking lakefront views and spectacular sunsets. Residents enjoy true resort-style living with access to a community clubhouse, pool, spa, shuffleboard courts, tennis & Pickleball courts. The highly desirable location offers close proximity to shopping, dining, schools, medical facilities, and LEGOLAND Florida Resort. Additional features include a private storage room off the patio, inside laundry, a tile roof, air conditioning, 24-hour security, meticulously maintained grounds, assigned parking, and ample guest parking. This is Florida lakefront living at its finest.

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

Listing Agent: Chip Fortenberry, Iii (863-673-9368)

Remarks: Under Construction. Turquesa BELOW MARKET INTEREST RATES with use of Seller's Preferred Lender. The Turquesa is the ultimate family haven, a two-story home featuring 4 bedrooms, 2.5 bathrooms and a private 2-car garage. This home offers an open concept living space designed for both relaxation and entertainment. The half bathroom off the foyer ensures every guest feels at home while the extended foyer opens to the main living and dining area. Featuring luxury vinyl plank flooring and convenient indoor-outdoor living with a lanai through sliding glass doors, it’s a haven of comfort and style perfect for gatherings. The kitchen includes stunning quartz countertops and sleek stainless-steel appliances. Enjoy the spacious upstairs recreation room and the convenience of a laundry room just steps away from the bedrooms. Did we mention the brand-new washer and dryer? The owner's suite is a secluded retreat with oversized his-and-her walk-in closets, dual vanity and a walk-in shower. Completing this expansive home is the smart thermostat with voice control and professionally designed landscaping, this is truly the epitome of family-friendly luxury! 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. WELCOME HOME to effortless Florida living with a view you'll never tire of! From the moment you step through the front door, your eyes are immediately drawn to the breathtaking, million-dollar view overlooking the well maintained fairways of the private golf course. Combined with mature tropical landscaping, exceptional curb appeal, and a charming covered front porch that's perfect for enjoying your morning coffee, this home offers an unforgettable first impression. Nestled within the gated community of Lake Bess Country Club, this beautifully maintained 3-bedroom, 2-bath residence offers the perfect blend of elegance, comfort, and carefree living. Soaring ceilings and abundant natural light create a warm, inviting atmosphere, while the expansive Florida Room seamlessly extends the living space, making it ideal for entertaining or relaxing year-round. During the cooler fall and spring months, the wall of windows opens completely, welcoming refreshing cross breezes creating the perfect indoor-outdoor Florida lifestyle. The spacious primary suite is a true private retreat, entered through elegant double doors and thoughtfully appointed with plantation shutters, two walk-in closets, a dedicated linen closet, dual vanities, and a beautifully tiled walk-in shower, offering both comfort and functionality. The eat-in kitchen provides generous cabinet space, all appliances, and a functional layout that keeps you connected to the main living areas. Off the kitchen is a spacious laundry room with full sink and cabinetry. Additional features include a NEW A/C system, durable tile roof, whole house generator that comes on the second power goes out, private irrigation well, and a screened lanai where you can unwind while taking in peaceful golf course views and Florida's beautiful weather. Life at Lake Bess Country Club is about more than just owning a home—it's embracing a lifestyle. Enjoy unlimited access to the immaculately maintained executive golf course, relax by the heated community pool, gather with neighbors at the clubhouse, or simply enjoy the gentle breeze while watching golfers pass by from the comfort of your own backyard. The monthly HOA fee of $500 includes lawn care, shrub maintenance, the heated community pool, and clubhouse access, as well as, unlimited golf on the beautifully maintained executive course—an outstanding value for those who love the game. Being offered fully furnished, this exceptional golf course home is truly move-in ready. If you've been searching for spectacular views, a peaceful setting, and maintenance-free Florida living in a secure gated community, this is the one. Schedule your private showing today!

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

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

Remarks: Investment opportunity. Stable tenant with opportunity.

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

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