Homes For Sale in Winter Haven 33881 - 308 homes

Remarks: Photos are preoccupancy. Turnkey, Renovated and Occupied Duplex 6.2 miles to Legoland – Make Money From Day 1-Investor Ready! Don't miss this income-producing duplex in a prime Winter Haven location. It is just 15 minutes from Legoland Florida and local shopping plazas. This is the perfect turnkey investment or an excellent opportunity for owner-occupancy with built-in rental income. Enjoy hassle-free ownership with a new roof, new flooring and new, efficient multi mini-split AC systems in both units. Each unit is equipped with new appliances and features modern updates throughout. The property offers a highly desirable configuration: Unit A is a spacious 3 Bed/1 Bath, and Unit B is a comfortable 2 Bed/1 Bath. That is a total of five bedrooms and two bathrooms across two separate units. Located in a high-demand rental market near major employment and amenities, this duplex is ready to generate income from day one. Invest smarter—act now before it's gone!

Listing is courtesy of: SPANN & ASSOCIATES REAL ESTATE (407-468-7512)

Listing Agent: Kal Scarvers (863-617-5236)

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

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

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

Remarks: Welcome to this beautifully renovated 3-bedroom, 2-bath home located in the heart of Winter Haven. Thoughtfully updated with modern finishes while maintaining its charm, this spacious property offers flexible living areas and plenty of room to spread out. Recent renovations provide a fresh, move-in-ready feel throughout the home. Previous owners added extra rooms and expanded living spaces, offering versatility for a home office, guest space, or bonus room. Square footage to be confirmed by buyer, as additions may not reflect current public records. Conveniently located near shopping, dining, schools, and all that Winter Haven has to offer, this property is a fantastic opportunity for homeowners or investors alike.

Listing is courtesy of: MARK SPAIN REAL ESTATE (855-299-7653)

Listing Agent: Patrick Massey (931-337-1678)

Remarks: One or more photo(s) has been virtually staged. $15,000 deduction on 5/8! 2500 sq ft for $310,000! Step into comfort, space, and opportunity in this move-in ready 4-bedroom, 2.5-bath home located in the established Forest Ridge community of Winter Haven—with no CDD. From the moment you arrive, the inviting covered front porch and mature landscaping set the tone for what’s inside. The thoughtfully designed layout offers the perfect balance of everyday comfort and flexible living. The main level features an open kitchen and living area, a versatile bonus room near the entry—ideal for a home office, playroom, or creative space—and a convenient half bath for guests. At the center of the home, the open-concept kitchen is built for connection, featuring a center island, black and stainless steel appliances, and seamless flow into the dining and living areas—perfect for entertaining or simply enjoying day-to-day life. Recently upgraded dishwasher and garbage disposal. Durable tile flooring and recently upgraded carpet throughout all the main living spaces and upstairs bedrooms adds a clean, modern feel and abundant natural light creates a bright, welcoming atmosphere. Upstairs, you’ll find all four bedrooms, including a spacious primary suite designed for relaxation, along with two full bathrooms and a conveniently located laundry area equipped with a smart washer and dryer. Each space is designed with comfort and functionality in mind. Step outside to a generously sized backyard ready for your vision—whether it’s a future pool, outdoor kitchen, garden, or play space, the possibilities are endless. Set within the peaceful surroundings of Forest Ridge, you’ll enjoy quiet streets while being just minutes from Highway 27 and a short drive to I-4, giving you easy access to shopping, dining, schools, and everything Central Florida has to offer. This home checks all the boxes—space, flexibility, location, and value. Schedule your private showing today and see the potential for yourself!

Listing is courtesy of: KELLER WILLIAMS SUBURBAN TAMPA (813-684-9500)

Listing Agent: Daniel Henzler (813-293-3603)

Remarks: Welcome home to this inviting upstairs condo located in the peaceful Lake Buckeye Condo community, where tranquil lake views and relaxed living come together. Step inside to find laminate and ceramic tile flooring throughout, offering both durability and easy maintenance. The open living and dining area is light and welcoming, seamlessly extending to a private 3x7 balcony, the perfect place to enjoy your morning coffee or unwind at the end of the day. Just beyond, the well-appointed kitchen comes complete with all appliances, granite countertops, and an adjacent utility room with washer/dryer hookups and extra cabinet storage. The split-bedroom floor plan provides excellent privacy. The primary suite features a walk-in closet and a private en-suite bathroom with a walk-in tile shower, while the second bedroom is conveniently located near the hall bath, ideal for guests or a home office. Residents enjoy access to community amenities, including a sparkling pool overlooking beautiful Lake Buckeye and community docks, perfect for lakeside relaxation and peaceful views. This condo offers a wonderful blend of comfort, convenience, and serene surroundings—an opportunity you won’t want to miss!

Listing is courtesy of: STAR REALTY OF WINTER HAVEN (863-299-7827)

Listing Agent: Carlee Marchetti (863-258-3338)

Remarks: One or more photo(s) has been virtually staged. PRICE IMPROVEMENT! SELLER MOTIVATED! Needs new carpet - giving buyers a clear opportunity to update the flooring to their own style and make it their own. 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 $20–$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 than 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: One or more photo(s) has been virtually staged. Discover the perfect blend of modern updates and serene living in this stunning 4-bedroom, 2-bathroom home. Located in the highly sought-after Country Club Estates, this residence offers the privacy you've been searching for with a screened-in back patio overlooking a peaceful pond-meaning no rear neighbors, just tranquil water views. Step inside to find a bright and airy open floor plan, freshly enhanced with new interior and exterior paint. The home is designed for both style and durability: Elegant luxury vinyl plank in all bedrooms and easy-to-maintain ceramic tile throughout the main living areas. Features timeless oak cabinetry, sleek granite countertops, and plenty of prep space. The popular split-bedroom floor plan ensures a private primary retreat, separate from the guest rooms.A dedicated inside laundry room and a spacious 2-car garage provide ultimate functionality. Location is everything! Enjoy the quiet atmosphere of an established community while being just moments away from modern conveniences. The brand-new Publix shopping center is right around the corner, making grocery runs and errands a breeze.Schedule your private showing today and experience Florida living at its finest!

Listing is courtesy of: ORLANDO REO PROF I INC (407-704-6924)

Listing Agent: Ronald Gentile (407-247-0849)

Remarks: Welcome to 3006 Elm Street in beautiful Winter Haven — a charming home full of potential and perfectly positioned for convenience! This 3-bedroom, 1.5-bath home also features a flexible office space that could easily serve as a 4th bedroom, playroom, hobby room, or home gym. Step inside to find new tile flooring, a remodeled bathroom, a newer roof, and updated ceilings that give the home a fresh and modern feel. The spacious kitchen offers plenty of room to cook, gather, and get creative with your dream design ideas. Outside, the backyard is a blank canvas ready for your personal touch — create the garden, outdoor kitchen, pool area, or entertaining space you've always wanted! Conveniently located near shopping, dining, attractions, and with easy access for commuting to both Tampa and Orlando, this property offers the perfect blend of comfort, opportunity, and location. Whether you're looking for your first home, investment property, or extra space to grow, this Winter Haven gem is ready to welcome you home!

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

Listing Agent: Michele Elchin (863-514-6880)

Remarks: Motivated Seller. Introducing a beautifully maintained home offering an excellent and functional layout. The first floor features a welcoming open concept with a half bathroom, living, dining, and kitchen areas, and a well-appointed kitchen with granite countertops, stylish backsplash, and elegant lighting fixtures. A sliding glass door brings in natural light and provides direct access to the backyard, enhancing the indoor-outdoor connection. The entire main level is finished with tile flooring, providing durability and easy maintenance. Upstairs, you will find three generously sized bedrooms and a versatile loft area, ideal for a playroom, home office, or study space. The primary suite offers a comfortable retreat with a barn door leading into the bathroom, which is also well-designed and spacious. The second and third bedrooms are well sized and highly versatile. This home has been very well cared for and is move-in ready. Enjoy a large backyard, perfect for entertaining, family gatherings, or simply relaxing outdoors. A great opportunity to own a home with space, comfort, and thoughtful design throughout. Schedule your private showing today.

Listing is courtesy of: HOMETRUST REALTY GROUP (813-444-5777)

Listing Agent: Barbara Prins (407-361-6061)

Remarks: ""SELLER MOTIVATED – PRICE IMPROVEMENT! BRING YOUR OFFER!"" Beautiful and well-maintained home featuring 4 spacious bedrooms and 2 bathrooms, offering plenty of space for comfortable family living and entertaining guests. Sliding glass doors lead to a covered patio and a private grassy backyard, perfect for relaxing and enjoying Florida’s outdoor lifestyle. The kitchen comes fully equipped with all appliances and features beautiful wood cabinetry and granite countertops, offering the perfect blend of style and functionality. The home also includes a 2-car garage and a fully equipped laundry room for added convenience. Located in a desirable community, this property offers comfort, practicality, and excellent investment potential. Conveniently located near LEGOLAND Florida Resort, Chain of Lakes Park, Downtown Winter Haven, shopping centers, restaurants, grocery stores, medical facilities, and provides easy access to Highway 27 for convenient travel to Orlando and Tampa. Winter Haven is also known for its beautiful Chain of Lakes, offering boating, fishing, and outdoor recreation opportunities. Currently tenant-occupied with a lease in place through November 2026 at $2,150 per month. After the lease term ends, the new owner may choose to renew or terminate the lease. Great opportunity for both investors and future homeowners.

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

Listing Agent: Anderson Siqueira, Sr (407-912-4688)

Remarks: Welcome to a home that offers more than just space — it delivers lifestyle, efficiency, and long-term value. Situated on a premium oversized corner lot, this 5-bedroom, 3-bathroom residence in Winter Haven is designed for those who appreciate both comfort and smart living. From the moment you enter, the clean, elegant tile flooring sets the tone for a modern and refined experience. The kitchen serves as the heart of the home, featuring soft-close cabinetry and elevated finishes — perfect for both everyday living and hosting guests. Step outside and envision your custom outdoor oasis. With hot and cold water lines already installed, your future outdoor kitchen is ready to come to life — ideal for entertaining and enjoying Florida living at its finest. But what truly sets this home apart is its fully paid-off solar panel system at closing — giving you immediate energy savings and a significant financial advantage from day one. Homes that combine space, upgrades, and built-in efficiency like this are rare. If you're looking for a move-in-ready property that delivers both lifestyle and smart investment value, this is one you don’t want to miss.

Listing is courtesy of: MY REALTY GROUP, LLC. (786-847-7421)

Listing Agent: Oscar Allende Melendez (787-409-2175)

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: Opportunities like this are nearly extinct. Just minutes from Winter Haven Country Club, this remarkable estate offers 10.98 acres of privacy, natural beauty, and flexibility in one of Winter Haven’s most coveted and tightly held locations—where land, space, and convenience rarely coexist. The 3,800 sq ft main residence has been completely remodeled with a refined, modern vision that blends luxury with everyday livability. Designed for both entertaining and comfortable living, the open-concept layout showcases luxury vinyl plank flooring throughout, expansive living areas, and a beautifully upgraded chef’s kitchen that serves as the heart of the home. With 4 bedrooms and 4 full bathrooms, the residence provides generous space for family and guests alike. Outdoors, a private pool invites relaxation while remaining surrounded by peaceful, natural views. Adding exceptional value and versatility, the property includes a 1,300 sq ft detached guest house featuring 2 bedrooms and 2 bathrooms, along with an upgraded kitchen and bath—ideal for extended family, long-term guests, or a private work-from-home or creative space. The land itself is what truly sets this property apart. The nearly 11-acre setting offers a thoughtful balance of open usable acreage, mature landscaping, and a scenic private pond, creating a sense of separation and tranquility that enhances both privacy and lifestyle. Multiple outbuildings, including a barn/garage and lean-to structure, provide ample room for storage, hobbies, equipment, or future expansion. In a market where acreage is disappearing and privacy is priceless, properties offering this scale of land, level of renovation, and proximity to town are exceptionally rare. This is not just a home—it’s a private retreat, a long-term asset, and an opportunity to own something truly irreplaceable.

Listing is courtesy of: THE MARKET REALTY COMPANY (863-999-4643)

Listing Agent: Brock Jennings (863-990-5846)

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: One or more photo(s) has been virtually staged. Welcome to this beautifully maintained 2018-built single-family home located at 1327 Salisbury Drive in Winter Haven. Offering approximately 2,300 square feet of living space, this spacious residence features 5 bedrooms, 3.5 bathrooms, and a two-car garage. The primary suite is conveniently located on the first floor, providing privacy and comfort, while the upstairs bedrooms are carpeted for a warm, cozy feel. The interior has been freshly painted, creating a bright and move-in-ready atmosphere throughout. Enjoy Florida living year-round from the screened-in back patio, perfect for relaxing or entertaining. It is conveniently located just minutes from downtown Winter Haven and close to the area’s picturesque lakes, shopping, dining, and major roadways. This home combines modern construction, generous space, and an excellent location. Schedule your private showing today!

Listing is courtesy of: TAH FLORIDA LLC (844-874-2661)

Listing Agent: Joshua Nogowski (754-234-9626)

Remarks: HUGE price reduction! Lakefront Living in Hamilton Point! Discover this spacious 5-bedroom, 3-bath home located in the upscale Hamilton Point community, within the city limits of Winter Haven. Situated on just under one acre, this rare lakefront property offers space, privacy, and the perfect setting for enjoying Florida’s outdoor lifestyle. Start your summer right with direct access to Lake Hamilton, a beautiful 2,142-acre lake known as one of Central Florida’s premier fishing destinations. Whether you enjoy waterskiing, jet skiing, fishing, or relaxing boat rides, this lake has something for everyone. Even better, this property offers true chain access to two additional lakes, expanding your boating adventures. Take a short ride across the water to two of the area’s favorite spots—Port 27 for waterfront dining or the local favorite Floridino's Italian Kitchen, known for serving some of the best pizza around. You might even spend an afternoon simply relaxing on the water while watching seaplanes land and take off. Surrounded by mature vegetation and located in a quiet, well-established community, this home truly has so much to offer. Properties like this are a rare find—especially on true lakefront acreage in such a desirable location.

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

Listing Agent: Lamanda Jones (863-557-3627)

Remarks: Seller motivated — great opportunity for investors or future homeowners! This beautiful corner lot home features 4 bedrooms and 2 bathrooms, offering comfort, space, and excellent income potential. The spacious kitchen comes fully equipped with all appliances, including a refrigerator, stove, microwave, and dishwasher, making it move-in ready from day one. The open-concept layout seamlessly connects the living and dining areas, creating the perfect space for entertaining guests or enjoying everyday family life. Sliding glass doors lead to a large backyard, ideal for outdoor activities, gatherings, or simply relaxing. Additional highlights include a 2-car garage, an already equipped laundry room, and a well-designed floor plan that offers both functionality and comfort. Located in the desirable Lake Lucerne community, residents enjoy great amenities, including a clubhouse, swimming pools, playground, and sidewalks for walking. Conveniently situated near Lake Alfred Elementary School, Daniel Jenkins Academy, Haines City Senior High School, as well as shopping, restaurants, and major roads with easy access to US-27, making commuting to Winter Haven, Davenport, and Orlando attractions even more convenient. Investor alert: The property is currently tenant-occupied with a lease in place through November 2026, generating $1,950/month in rental income. After the lease term ends, the new owner may choose to renew the lease or have the tenant vacate. Don’t miss this incredible opportunity!

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

Listing Agent: Anderson Siqueira, Sr (407-912-4688)

Remarks: Welcome to this Charming and newly remodeled home, located in the heart of Winter Haven! This inviting property offers comfortable living with a functional layout, perfect for both relaxing and entertaining. Whether you’re a first-time homebuyer, downsizing, or looking for an investment opportunity, this home is a must-see!

Listing is courtesy of: TCA REALTY, LLC (407-507-3982)

Listing Agent: Deidre Rios (407-433-6238)

Remarks: Under contract-accepting backup offers. Welcome to a home where comfort, convenience, and peace of mind come together in one of Winter Haven’s most desirable and evolving areas. Nestled just minutes from the shores of Lake Howard and the charm of Downtown Winter Haven, this property offers the lifestyle so many are seeking—close to it all, yet tucked away in a quiet, established neighborhood.From the moment you arrive, you’ll appreciate the care and updates that make this home truly move-in ready. Major systems have already been taken care of for you, including a brand-new hot water heater installed in 2026, roof and HVAC systems both replaced in 2018, giving confidence for years to come. Inside all-new windows bring in natural light while improving energy efficiency. The home continues to shine with newer cabinets and updated appliances. The interior tells a story of thoughtful updates and everyday functionality—spaces that feel welcoming whether you’re hosting friends, enjoying a quiet evening, or simply living life comfortably. Every improvement has been made with both style and practicality in mind, allowing you to settle in without the stress of immediate projects.Step outside and you’re just moments away from everything that makes Winter Haven special. Spend your weekends enjoying the Chain of Lakes lifestyle at Lake Howard, take in the growing dining and entertainment scene downtown, or simply enjoy the continued growth and investment happening throughout the area—making this not just a great home, but a smart move for the future.If you’ve been looking for a home that blends updated features, prime location, and long-term value, this one checks all the boxes.

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

Listing Agent: Chris Loschiavo (863-280-2201)

Remarks: Under contract-accepting backup offers. Welcome to 525 Winter Terrace in Winter Haven, an inviting, move-in-ready 2-bedroom, 2-bath, single-level townhouse in a maintenance-free family community with outstanding amenities. Step inside to find ceramic tile throughout the main living areas, spacious bedrooms, and a bright Florida room perfect for relaxing or entertaining. The heart of the home is the completely updated kitchen featuring nice appliances, wood cabinetry, and granite countertops, complemented by neutral interior paint and updated tile. Enjoy even more comfortable living space in the enclosed back room, offering additional air-conditioned square footage. The primary suite has sliding glass doors that lead to your own, private, enclosed porch. Community perks include a clubhouse, solar-heated pool, shuffleboard, and a private boat dock on beautiful Lake Smart. Schedule your showing today because this one won’t last long!

Listing is courtesy of: THE SIMON SIMAAN GROUP (407-558-1396)

Listing Agent: Oralis Perez (407-325-1045)