Winter Haven Homes For Sale & Real Estate - 1003 homes

Remarks: 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.

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

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

Remarks: Welcome to this charming home in the desirable Lake Dexter Woods community of Southeast Winter Haven. This well-maintained residence offers comfortable living with an open and inviting layout, spacious living areas, and abundant natural light throughout. The kitchen provides ample cabinet and counter space, while the primary suite features a private bath and generous closet storage. Enjoy Florida living year-round from the enclosed Florida room, perfect for relaxing or entertaining. The property also features a fenced backyard with mature landscaping and low-maintenance outdoor spaces. Residents of Lake Dexter Woods enjoy access to community amenities including a pool, boat ramp, and dock with access to Lake Dexter. Conveniently located near shopping, dining, medical facilities, and major roadways, this home offers both comfort and convenience in a sought-after location. This home has lots of updates! lighting, electrical panel and outlets, plumbing, 2021 Water heater, 2024 Roof, 2025 HVAC.

Listing is courtesy of: DILIGENCE LLC (727-400-5063)

Listing Agent: Malachi Gaddis (941-875-2111)

Remarks: PRICE REDUCTION!!! MOTIVATED SELLER!!! Discover this exceptional income-producing property perfectly situated on a spacious 0.48-acre lot in the heart of Winter Haven. This versatile property features two separate living spaces, one currently rented—providing immediate income and excellent long-term investment potential. The main home which is now vacant and ready for it's new owners or tenants offers 3 bedrooms and 2 bathrooms, including a generous master suite with an en-suite bath. The open and functional layout makes it ideal for families or long-term tenants. Attached to the main residence is a 484 sq. ft. in-law suite currently rented, complete with a full kitchen, bedroom, bathroom, and private entrance. This flexible space can serve as an additional rental unit, private guest quarters, or be seamlessly integrated into the main living area for multi-generational living. This home was recently appraised above the asking price, giving buyers instant equity and outstanding value. Whether you’re an investor seeking steady cash flow or a homeowner looking for flexibility, this property is a rare find. Take advantage of strong rental demand, potential appreciation, and the benefits of owning in one of Florida’s fastest-growing counties, consistently rated among the best places to live. Don’t miss your chance to own this unique multi-unit property—schedule your private showing today!

Listing is courtesy of: BRIGHT REALTY (941-552-6036)

Listing Agent: Jen Victor (941-587-2787)

Remarks: Why buy new when this is BETTER than NEW? This immaculate and spacious home features 5 bedrooms, 3 baths, 2 car garage, a fenced backyard and a water view! What more could you ask for? It’s the perfect blend of comfort and affordability with a modern style. The home features an open concept living room, dining room and kitchen. Perfect for entertaining! The sellers have removed the standard Formica countertops in the kitchen and bathrooms and replaced them with a beautiful white Quartz! But that's not all, they also replaced the carpet on the stairs with a beautiful Red Oak wood, fenced in the backyard, updated the faucets, fixtures, and hardware throughout. They also added a shiplap accent wall in the upstairs loft and laundry room. There is one bedroom and one full bathroom located on the main floor ideal for guests or someone that can't climb stairs. Upstairs, you'll notice the versatile loft space that is currently being used as a home office but would also work as a playroom or 2nd living area. The generous primary suite with a huge walk in closet and en-suite bathroom, along with 3 additional bedrooms, a bathroom and the laundry room are also located upstairs. The fully fenced backyard provides privacy and is the perfect place to unwind and relax. Located in a desirable and quiet community close to dining, shopping, schools, entertainment, and major highways. Don't miss out on this beauty!

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

Listing Agent: Mindy Russo (863-812-1294)

Remarks: This Azure floor plan offers a welcoming formal entry and hallway. A spacious great room with kitchen is open to dining and family entertainment area that leads to a covered patio. Also included is a great sized primary bedroom with a primary bath and walk-in closet. Included features: 9"4' ceilings and 8' doors, 42' cabinets and white quartz counter tops in kitchen, ceramic tile throughout the wet and main living areas of the home. All bedrooms, family room, and covered lanai are prewired for ceiling fans. *Take advantage of special financing on quick move-in homes OR buy a to-be-built home and enjoy up to $20,000 in Flex Funds toward homes that can close in a timely manner! Options may vary by community, and offers are available on select homes on a first-come, first-served basis. Contact builder for more information!

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

Listing Agent: Stephanie Morales, Llc (407-399-2055)

Remarks: Love the idea of living near the water without paying waterfront prices? This long-time family home, cherished since 1973, offers a rare opportunity to own a sprawling 3-bedroom bedroom 1.5 bathroom home in Northwest Winter Haven. Enjoy being just a block from a public park and only minutes from a neighborhood boat ramp providing access to Lake Howard and the famous Chain of Lakes. With over 1,600 square feet, bonus spaces, and a large yard, the possibilities are endless. Cash or Renovation Loan financing makes this a fantastic opportunity for buyers looking to add their personal touch and create a home to enjoy for generations.

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

Listing Agent: Kimberly Davis (850-625-8855)

Remarks: One or more photo(s) has been virtually staged. Welcome to this stunning Winston floorplan, located in the highly sought-after community of Willowbrook near a beautiful golf course in Winter Haven, FL. This spacious 5-bedroom, 3-bath home offers 2,531 square feet of living space, and providing excellent curb appeal in it's elevation. Inside, you'll find gorgeous White cabinets complemented by sleek quartz counter tops 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: Welcome to your own private backyard retreat in the heart of Winter Haven! This beautifully maintained 3-bedroom, 2-bath pool home sits on a spacious .31-acre lot with NO HOA and offers the perfect blend of comfort, convenience, and Florida living. The true showstopper is the incredible approximately *983-square-foot covered lanai*, creating an expansive outdoor living space rarely found in homes of this size. Perfect for entertaining, relaxing, outdoor dining, or even a home gym, this massive covered retreat overlooks the sports-style pool, oversized fenced backyard, custom playground, firepit, raised irrigated garden beds, and turf-and-tile entertaining area. Best of all, enjoy spectacular *LEGOLAND fireworks* views right from your own backyard. Inside, you'll find a bright and inviting floor plan with generous living spaces, comfortable bedrooms, and a well-appointed kitchen that flows seamlessly into the living and dining areas. Recent updates provide peace of mind, including a New Roof (2023), New Covered Lanai (2023), whole-home re-plumbing (2024), reverse osmosis system in the kitchen (2024), stainless steel dishwasher (2021), gas water heater (2021), irrigation system for yard (2023), updated light fixtures throughout, Ring security system with automatic flood lights, and added recessed lighting in the living room and kitchen. The outdoor space was thoughtfully enhanced in 2024 with stained fencing, rocked and irrigated landscape borders, a fully sealed playground, and beautifully designed gathering spaces that make this property ideal for everyday living and entertaining alike. Conveniently located just minutes from Downtown Winter Haven, LEGOLAND Florida Resort, major hospitals, shopping, dining, and everyday conveniences, this move-in-ready home offers the perfect combination of location, lifestyle, and value. Don't miss this rare opportunity to own a beautifully updated pool home with an extraordinary outdoor living experience. Schedule your private showing today!

Listing is courtesy of: LIVE FLORIDA REALTY (863-868-8905)

Listing Agent: Jenna Henderson (850-524-3843)

Remarks: One or more photo(s) has been virtually staged. Welcome to Peace Creek Reserve! Built in 2024, this move-in ready home offers the benefits of newer construction without the wait. Featuring 4 bedrooms, 3 full bathrooms, and a private in-law suite complete with its own kitchen and full bath, this flexible floor plan is ideal for multigenerational living, extended family, guests, or a private home office setup. The spacious main kitchen serves as the heart of the home, showcasing a center island with sink, abundant cabinetry, and an open-concept design that flows seamlessly into the living areas. Tile flooring extends throughout the main living spaces, while the bedrooms provide the comfort of carpeting. The primary suite offers a generous bedroom, walk-in closet, and private bath with dual vanities. Three additional bedrooms and two full baths provide plenty of room for family and guests. Step outside to the covered rear lanai and backyard, perfect for relaxing or entertaining. Conveniently located in Peace Creek Reserve, residents enjoy onsite pool and playground as well as easy access to shopping, dining, medical facilities, schools, and major commuter routes. Why wait months for new construction when you can move into this nearly new home today?

Listing is courtesy of: REDFIN CORPORATION (617-458-2883)

Listing Agent: Amy Long (863-712-9827)

Remarks: Welcome to 3097 Buckeye Pointe Drive, a fully updated pool home in Winter Haven, Florida, offering the space, flexibility, and upgrades today's buyers are searching for in Polk County. If you've been looking for a move-in ready home with a private pool, screened spa, modern finishes, and no rental restrictions, this property deserves a spot at the top of your list.Located in the established Buckeye Pointe community, this spacious two-story home features 5 bedrooms, 2.5 bathrooms, and more than 2,500 square feet of living space. The versatile floor plan includes a first-floor bedroom, making it ideal for multigenerational living, visiting guests, a private home office, or a fitness room.From the moment you step inside, you'll notice the extensive updates throughout. The entire first floor showcases oversized 24x36 porcelain tile, creating a clean, modern look that is both stylish and easy to maintain. The renovated kitchen serves as the heart of the home with updated cabinetry, a large center island, upgraded lighting, and newer appliances including the refrigerator and dishwasher. Every bathroom has been remodeled, while fresh interior and exterior paint give the home a bright, updated feel throughout.Step outside and enjoy the Florida lifestyle year-round. The screened and heated pool and spa create the perfect setting for relaxing after work, entertaining family and friends, or enjoying weekend gatherings. The vinyl fenced backyard offers privacy, while mature fruit trees provide character and charm that are increasingly difficult to find. Major improvements include a newer 2023 roof and a 2020 water heater, giving buyers added confidence and helping reduce future maintenance concerns. One of the most attractive features of this property is the absence of rental restrictions. Buyers searching for an Airbnb-friendly home in Winter Haven, a Florida vacation home, a second home near Orlando attractions, or an income-producing investment property will appreciate the flexibility this community offers. Conveniently located near shopping, restaurants, medical facilities, schools, and major transportation routes, this home provides easy access to everything Central Florida has to offer. Whether you're commuting to Orlando, exploring nearby lakes, visiting world-famous attractions, or simply enjoying the growing Winter Haven lifestyle, this location puts you close to it all.Buyers frequently searching for "homes with pools in Winter Haven," "5-bedroom homes in Polk County," "updated homes near Orlando," "Airbnb investment properties in Central Florida," "homes with no rental restrictions," or "move-in ready Florida homes with a pool" will find everything they're looking for at 3097 Buckeye Pointe Drive. This is more than just a house. It's a move-in ready Florida lifestyle with room to grow, space to entertain, and the flexibility to fit your future plans.

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

Listing Agent: Desiree Carlson (541-743-1985)

Remarks: Welcome to refined Florida living in the serene, gated, 55+ community of Preserve at Lakeside Landings. This community designed with enjoying your Florida lifestyle, is home to 44 residences, 2 pools, a playground, and sidewalks to keep you active. HOA includes lawn maintenance which allows you to relax in your stunning new home! Thoughtfully designed with a triple-split floorplan, this residence offers exceptional privacy and versatility—ideal for multi-generational living. Manicured tropical landscaping and pristine sidewalks lead you inside, where the first split features two guest bedrooms and a shared bathroom. Continuing into the main corridor, you’ll find the third bedroom or office along with the conveniently located laundry room.The home then opens into a bright, airy living space with 9-foot ceilings and tile flooring. An elegant dining area overlooks the pool, while the beautifully appointed kitchen showcases solid wood cabinetry, granite countertops, stainless steel appliances, and a generous island perfect for entertaining. The primary suite serves as a peaceful retreat with updated flooring, a walk-in closet, and a spa-inspired bath complete with dual sinks, granite, and a glass walk-in shower. Outdoors, the property transforms into a true tropical sanctuary. A stunning saltwater pool with a cascading waterfall is framed by lush landscaping that is home to several citrus trees. This secluded, spa-like atmosphere is ideal for relaxation or entertaining. With a tranquil natural backdrop and effortless indoor-outdoor flow, this home blends elegance, comfort, and resort-style appeal. Fresh interior paint, an immaculate garage, energy-efficient insulation, and lawn care included in the HOA make this home truly move-in ready—offering a lifestyle of ease, beauty, and authentic Florida living. Upgrades include kitchen appliances 2025, new disposal, Pentair salt system is 4 years old. Pool deck was sealed one year ago. Don't hesitate, opportunities like this are rare, so make your appointment today!

Listing is courtesy of: FLORIDA REAL ESTATE COMPANY (863-701-3487)

Listing Agent: Cyleste Goodson (863-701-3487)

Remarks: PRICE TO SELL!!!UP TO $5,000 IN BUYER INCENTIVES AVAILABLE! This property may qualify for up to $5,000 in closing cost credit when using the seller's preferred lender. Ask us how to qualify! Welcome to Sanctuary by the Lake — one of Winter Haven's most sought-after gated lakefront communities, built by Southern Homes along the stunning shores of Lake Rochelle, part of Florida's renowned Chain of Lakes. Whether you're looking for your forever home or a high-demand investment property, this one checks every box. This move-in ready, beautifully upgraded 3-bedroom, 2-bathroom home seamlessly blends modern design with relaxed lakeside living. Step inside to a spacious foyer that opens into a bright, open-concept living and dining area filled with natural light. Glass sliding doors lead to a generous, fully fenced backyard with room to add a pool — perfect for families and a future value-add for investors. The show-stopping kitchen is designed to impress, featuring stainless steel appliances, a mosaic tile backsplash, white shaker cabinets, a large center island with sink, and a full pantry. Designer touches throughout — bold accent walls, custom pendant lighting, and wood-look tile flooring — give this home a distinctive, upscale feel that stands out in any market. The primary suite is a true retreat with a walk-in closet and a spa-inspired en-suite bath complete with a soaking tub, walk-in glass shower, dual-sink vanity, and elegant tile finishes. Two additional bedrooms offer flexibility for family, guests, or a home office. A stylishly updated second bath rounds out the interior. Outside, enjoy a covered patio and lush backyard — your own private piece of Florida paradise. The 2-car garage adds convenience and storage. Community amenities include exclusive access to Lake Rochelle for kayaking and water sports, scenic walking trails, private docks, and a playground — all with low HOA fees and absolutely NO CDD. Ideally located near US-27, major shopping, dining, medical centers, and Central Florida's top destinations including LEGOLAND®, Walt Disney World®, and Universal Studios®. This is a limited opportunity — priced to sell and incentives won't last long. Call today to schedule your private showing!

Listing is courtesy of: REMAX PREMIER PROPERTIES (407-343-4245)

Listing Agent: Julio Salgado (407-791-0265)

Remarks: Estate-owned property being sold AS-IS for investor value. Seller inherited the home and has never occupied the property. Property requires significant renovation and is cash offers only; may not qualify for traditional financing. Seller will make no repairs or concessions. Buyer to perform all inspections and due diligence prior to closing.

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

Listing Agent: Kevin Tison (863-206-5755)

Remarks: Location! Location! Location! This beautiful fully furnished home in Oakwood Estates is located next to the pool, tennis courts, and smaller clubhouse. Walk into the lanai as you enter the home. Once inside the home you will find a cozy family room and an open and and appealing kitchen just perfect for entertaining. The living room beyond the kitchen is open and spacious. The refrigerator was new in 2025. The guest bedroom opens onto the guest bath giving your overnight guest their own bathroom. The primary bedroom is large enough for a king sized bed, plus lots of closet storage space. The laundry with new washer and dryer is located inside the home. The roof was done in 2019 and the air conditioner in 2024. And if that isn't enough, there is new carpet throughout the home. Oakwood Estates is a 55+ community offering many activities and amenities. You can stay as busy as you would like, or just sit back and watch the world go by.

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

Listing Agent: Kathy Devor (573-450-1679)

Remarks: Under contract-accepting backup offers. Short Sale. Don’t miss the opportunity to own this one-of-a-kind, 3-bedroom, 2-bathroom, 2-car garage custom home. Upon arriving at the property, you are greeted by an oversized lot and mature trees in a quiet, well-established neighborhood. Inside, the home offers an open and split floor plan, cathedral ceilings, and an indoor/outdoor pool that flows from the back patio into the living room, adding a unique feature to this property—perfect for entertaining and allowing you to take a dip in any weather. On the left side of the home are two spacious bedrooms with large closets and a shared bathroom featuring a single vanity and a shower/tub combo. Moving to the right side of the house, you’ll find the master suite, loft, and kitchen. The master suite offers ample space and direct access to the pool area. The en-suite bathroom includes a garden tub and walk-in shower. The loft overlooks the living room and pool area and also contains two large storage spaces on either side, making storage accessible while serving as a great spot to watch a show and unwind. The kitchen features tile countertops and a small bar for additional seating. Right out back, the pool is enclosed in a full-screen cage with a large deck. The yard also boasts a shed for storage and plenty of space for activities. This home has so much to offer. Don’t wait—schedule your private showing today!

Listing is courtesy of: LPT REALTY LLC (386-388-7877)

Listing Agent: Trent Shackelford (941-518-7875)

Remarks: Feature highlight — The home features a newly installed roof (May 2026), ensuring durability and reduced maintenance for the next owner! 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: Welcome to 814 Sunset Cove Drive in Winter Haven! This move-in ready 4-bedroom, 2-bathroom home offers the perfect combination of comfort, style, and convenience. Nestled in a wonderful neighborhood, this well-maintained property features a spacious and functional floor plan designed for both everyday living and entertaining. Step outside to your own private retreat and enjoy the beautiful pool area, perfect for relaxing on sunny Florida days, hosting family gatherings, or creating lasting memories with friends. The backyard provides an inviting outdoor space to enjoy year-round. Inside, you’ll find generously sized bedrooms, comfortable living spaces, and a layout that makes you feel at home the moment you walk through the door. Whether you’re looking for your first home, a place to grow, or simply a move-in ready property with an exceptional outdoor living area, this home checks all the boxes. Don’t miss the opportunity to make this beautiful Winter Haven home your own!

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

Listing Agent: Ricky Catanzano, Jr (352-359-8991)

Remarks: Welcome to this beautifully maintained 4-bedroom, 2-bathroom home located in the desirable gated community of Terranova in Winter Haven. Offering approximately 1,960 square feet of living space, this residence features an open and functional floor plan designed for comfortable everyday living and entertaining. The spacious kitchen flows seamlessly into the main living areas, creating the perfect gathering space for family and friends. The primary suite provides a private retreat, while the screened lanai with a private spa offers the ideal place to relax and enjoy Florida living year-round. The beautifully landscaped backyard provides additional outdoor space for entertaining or unwinding. Conveniently located just 5 minutes from LEGOLAND Florida Resort and close to shopping, dining, hospitals, schools, and major roadways, this home offers the perfect combination of comfort, convenience, and location. The property is equipped with leased solar panels, which will be transferred to the buyer at closing, subject to the solar company's approval and transfer requirements. Schedule your private showing today and discover everything this exceptional home has

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

Listing Agent: Rosa Nieves (407-870-3125)

Remarks: Prime mixed-use redevelopment opportunity in one of Winter Haven’s most strategic growth corridors. Situated directly across from Winter Haven Hospital, this property offers exceptional potential for investors, builders, and developers seeking to capitalize on a location positioned for long-term growth and redevelopment. The property is located within a Mixed-Use (MU) district that allows up to four residential dwelling units per lot and building heights of up to four stories, creating significant flexibility for residential, mixed-use, or income-producing projects. Its highly desirable location near major employment centers, medical services, retail, dining, and downtown Winter Haven further enhances its development appeal. An exceptional opportunity exists to assemble a larger development footprint through the acquisition of the adjacent parcel at 203 Ave C NE (see separate MLS#O6414107), as well as 209 Ave C NE (coming soon), offering the potential for a multi-parcel redevelopment project in a high-demand area. Opportunities of this scale and location are increasingly rare in Winter Haven. Whether acquired individually or as part of a larger assemblage, this property presents a compelling investment opportunity for developers seeking density, flexibility, and a premier location directly across from one of the area’s largest healthcare campuses.

Listing is courtesy of: MBA REALTY GROUP, INC (407-291-4665)

Listing Agent: Paola Arias (407-969-9211)

Remarks: Welcome to Mandolin! Fall in love with this 4-bedroom, 2-bathroom SALT WATER POOL home PLUS a flex room/office offering an impressive 2,506 square feet of living space in a highly desirable gated community. You’ll appreciate the exceptional curb appeal, extended driveway, detailed custom trim work, Luxury Vinyl Plank and tastefully added upgrades throughout the home. Discover a spacious split floor plan featuring elegant accents that welcome you in. The kitchen features granite countertops, solid wood cabinets, NEWER appliances and a large pantry.The oversized indoor laundry room makes your life easy! The flexible office/den space is perfect for working from home, a playroom, fitness area, or additional guest space. The spacious primary suite is privately tucked away and features oversized his-and-her walk-in closets along with a beautifully remodeled primary bathroom complete with an enlarged walk-in shower, stylish new tile and backsplash, and a relaxing separate garden tub. Three additional generously sized bedrooms provide plenty of room for family and guests. Step outside to your own private backyard retreat and enjoy days of fun in the sun featuring a newly added heated saltwater pool and pool cage, screened porch, patio paver deck, and fully fenced backyard with double gate—perfect for entertaining, relaxing, and enjoying the Florida lifestyle year-round. You can also store your boat or outdoor toys! Additional features include termite bait system, regular pest control maintenance, and much more! Conveniently located near Legoland, the Chain of lakes, schools, shopping, medical facilities, restaurants, an all Winter Haven has to offer. Easy commute to all Central Florida Attractions and Florida Beaches! Call today for your showing!

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

Listing Agent: Tina Heim, Pa (863-370-1786)