Winter Haven Homes for Sale

Winter Haven Homes for Sale

Welcome to Winter Haven, Florida – a hidden gem nestled in Polk County that perfectly blends small-town charm with modern conveniences. Known for its stunning chain of lakes, Winter Haven boasts a picturesque setting that offers endless opportunities for outdoor adventures, from fishing and boating to hiking and biking along scenic trails. The city’s warm climate and sunny skies make it an ideal locale for year-round enjoyment.

Winter Haven is also rich in history and culture. With its vibrant downtown area filled with unique shops, delightful cafes, and a thriving arts scene, residents can immerse themselves in the community spirit. The city is home to the renowned LEGOLAND Florida Resort, making it a prime destination for families and thrill-seekers alike.

For those seeking a place to call home, Winter Haven has an impressive array of homes for sale. Whether you’re looking for a cozy bungalow, a spacious family home, or a luxurious waterfront property, the real estate market here offers something for everyone. With affordable prices and a variety of architectural styles, you’ll find the perfect fit for your lifestyle and budget.

The welcoming community, excellent schools, and abundant recreational opportunities make Winter Haven an ideal choice for families, retirees, and everyone in between. Explore the homes for sale in this enchanting city and discover why Winter Haven is not just a place to live, but a place to thrive. Embrace the Florida lifestyle and make Winter Haven your new home today!

Newest Winter Haven Homes for Sale

$385,000
4 Beds ⋅ 2 Baths ⋅ Hamilton West Ph 02 SubDv. ⋅ 33881 Zip Code
Welcome to **107 Sanderling Drive**, a spacious and inviting **4-bedroom, 2-bathroom single-family home** in the desirable Hamilton West community of Winter Haven. Offering approximately **2,567 square feet of living space**, this one-story home provides plenty of room for comfortable everyday living, entertaining, and creating lasting memories. Step inside to a welcoming floor plan featuring spacious living and dining areas, an eat-in kitchen, vaulted ceilings, crown molding, and a combination of wood and tile flooring. The kitchen offers generous cabinet and counter space and opens toward the breakfast area and family room, creating a great gathering space for family and friends. The split-bedroom layout provides privacy for the primary suite, which features **two walk-in closets, dual sinks, a garden tub, and a separate walk-in shower**. Recent and important property improvements include a **new roof installed in 2024 with architectural shingles**, providing added peace of mind for years to come. The home features an **HVAC system with dual-purpose natural gas heating and cooling**, along with a **natural gas water heater**. A **well irrigation system services the sprinkler system**, helping maintain the landscaping while providing an efficient source for irrigation. Additional features include a **two-car attached garage**, ceiling fans, window treatments, and a spacious **0.26-acre lot** with approximately **11,326 square feet of land**, providing plenty of room to enjoy Florida's outdoor lifestyle. Located in the heart of Winter Haven's famous **Chain of Lakes region**, residents can enjoy boating, fishing, kayaking, water sports, and beautiful waterfront recreation. Nearby **Lake Howard** and the surrounding lakes provide numerous opportunities for outdoor adventures and relaxation. Enjoy the shops, restaurants, entertainment, and community events of **downtown Winter Haven**, or spend the day exploring local parks and nature areas. Family-friendly attractions and activities are also nearby, including **LEGOLAND Florida Resort**, golf courses, walking and biking trails, and numerous recreational facilities throughout the Winter Haven area. Conveniently located with easy access to major roadways, this home provides a great balance of peaceful residential living and proximity to shopping, dining, recreation, medical facilities, and Central Florida attractions. With its spacious floor plan, **2024 architectural shingle roof**, natural gas HVAC and water heater, well irrigation system, and desirable Winter Haven location, **107 Sanderling Drive** is an excellent opportunity to enjoy the Central Florida lifestyle. **Come see all this wonderful home has to offer!**

107 Sanderling Drive, Winter Haven
$325,000
3 Beds ⋅ 2 Baths ⋅ Jan Phyl Village Un #16 SubDv. ⋅ 33880 Zip Code
Enjoy Florida living with your own private pool and plenty of space to spread out in this recently remodeled 3-bedroom, 2-bathroom Winter Haven home. Inside, the spacious floor plan offers an open main living area where the family room, dining space, and kitchen flow together, creating a comfortable setting for both everyday living and entertaining. Recent updates throughout give the home a fresh, updated feel, including new flooring throughout. The updated kitchen features brand-new cabinets and countertops, stainless steel appliances, and a large island that provides generous prep space and additional seating. One of the home's standout features is the additional flex room, giving you even more room to make the home work for your lifestyle. Use it as a second living area, game room, home office, playroom, or entertainment space. Sliding glass doors fill the room with natural light and open directly to the covered patio, extending the living space outdoors. The primary bedroom features its own private bathroom and closet, while two additional bedrooms and a second full bathroom provide flexibility for family, guests, or a home office. The neutral interior and open layout make the home feel bright and inviting while offering plenty of possibilities for personalizing each space. Step outside to your own private backyard retreat featuring a remodeled pool with new tile and a freshly painted pool deck, perfect for relaxing, entertaining, or enjoying Florida's beautiful weather. The covered patio extends the living space outdoors and provides a great spot for dining or unwinding by the pool. With plenty of surrounding backyard space, there's room to enjoy sunny afternoons by the water or relax beneath the covered patio. With a recently remodeled interior, updated kitchen, new flooring, remodeled pool, multiple living spaces, a flexible floor plan, and indoor-outdoor living, this Winter Haven home brings together the space and features that make everyday Florida living easy to enjoy.

205 Fern Road, Winter Haven
$1,100,000
2 Beds ⋅ 3 Baths ⋅ Lake Eloise Sub SubDv. ⋅ 33884 Zip Code
Welcome to an exceptional and truly distinctive lakefront estate with a private pool, defined by architectural artistry, refined character, and timeless Spanish-Mediterranean elegance. This 2-bedroom, 3-bath residence offers more than 3,700 square feet under roof, providing expansive, thoughtfully designed interiors ideal for both entertaining and serene everyday living. From the moment you enter, you are welcomed by an atmosphere of bespoke craftsmanship and enduring design. Exquisite brick archways, rich warm wood detailing, and three elegant wood-burning fireplaces establish a setting that is both inviting and unmistakably unique. The kitchen continues this elevated architectural story, showcasing custom extensive cabinetry, stone countertops, premium stainless steel appliances, and a dramatic brick-arched passage that serves as a striking focal point. Thoughtfully designed to capture the essence of the Florida lifestyle, the home opens to a private resort-style swimming pool set against a peaceful lakefront backdrop, creating an extraordinary environment for relaxation, refined entertaining, and sweeping waterfront views. Seamless indoor-outdoor transitions enhance the sense of openness throughout, making the residence equally suited as a distinguished full-time home or an exclusive private lakefront retreat. With its authentic Spanish-Mediterranean influence, handcrafted brick detailing, multiple fireplaces, resort-style pool, and premier waterfront location, a rare opportunity to own a residence of true individuality and lasting appeal—one that cannot be replicated. Schedule your private showing and experience the elegance and exclusivity of this remarkable lakefront offering.

Winter Haven
$140,000
2 Beds ⋅ 2 Baths ⋅ Imperial Villas SubDv. ⋅ 33880 Zip Code
Welcome to easy Florida living in desirable Imperial Villas! This well maintained 2 bedroom, 2 bath villa offers a bright, open layout with a comfortable flow. Roof Replaced 2020. The spacious primary suite includes a walkin closet and private bath, and the screened lanai is perfect for morning coffee or relaxing in the evening. Enjoy the heated community pool and a low maintenance lifestyle, with the HOA covering water, sewer, trash, and exterior maintenance. Conveniently located near Lake Howard, shopping, dining, and downtown Winter Haven, this home blends comfort and convenience. Schedule your private showing today.

345 24th Street Nw Unit 1, Winter Haven
$369,900
3 Beds ⋅ 2 Baths ⋅ Hartridge Hills SubDv. ⋅ 33881 Zip Code
Move-In Ready Custom Home in a Gated Community Near the Airport Ideally located for aviation professionals seeking convenient access to the airport or for families looking for a safe, gated community, this beautifully updated custom home offers the perfect blend of comfort, style, and convenience. Built in 1988, this spacious home features an open floor plan with soaring ceilings, stunning exposed wood beams, solid wood doors, and matching wood baseboards that create warmth and character throughout. The split-bedroom layout provides privacy, while the attached two-car garage adds everyday convenience. The recently remodeled interior showcases numerous upgrades, including luxury vinyl plank flooring, fresh interior paint, and updated lighting throughout. The beautifully renovated kitchen features custom wood cabinetry, granite countertops, and a full suite of matching Whirlpool appliances. Both bathrooms have been tastefully updated with new wood vanities, Delta fixtures, Kohler toilets, and stylish tile finishes. The primary bedroom offers the comfort of new carpeting, and the home features smooth ceilings throughout—no popcorn ceilings. Additional highlights include generous laundry room storage, fresh exterior paint, and numerous major improvements for peace of mind. A new roof was installed in March 2026, along with new double-insulated windows, new irrigation, and professional landscaping. Every major update has been completed—simply move in and enjoy. The HOA fee is just $150 per month and includes lawn mowing and fertilization, making it easy to maintain a beautiful yard year-round.

218 Lake Hartridge Drive Nw, Winter Haven
$259,000
3 Beds ⋅ 2 Baths ⋅ Forest Ridge SubDv. ⋅ 33881 Zip Code
Welcome to this beautifully maintained 3-bedroom, 2-bath home in Forest Ridge, offering a great floor plan that feels bright and spacious! The split-bedroom layout provides privacy and flexibility, while the inviting kitchen features an eat-in area and breakfast bar, making it perfect for everyday living and entertaining. A separate laundry room adds convenience, and the home also features ceiling fans throughout. Step outside to the screened lanai overlooking a large, private, fully fenced backyard—an ideal space for relaxing, entertaining, or enjoying the outdoors. The home also features a new roof installed in 2025 and custom-fitted hurricane shutters for each window, designed for easy installation when needed for storm protection. Enjoy the best of both worlds in Forest Ridge—a quiet neighborhood setting with convenient access to Highway 27 and I-4. Shopping, dining, schools, and the many attractions of Central Florida are all within easy reach. Add in the spacious layout and large private backyard, and you have a home that offers both comfort and convenience. This home is move in ready and waiting for the new owner.

5621 Forest Ridge Drive, Winter Haven
$299,000
3 Beds ⋅ 2 Baths ⋅ Saxon Myers Rep Ph 2 SubDv. ⋅ 33881 Zip Code
Affordable pool home with NO HOA in the heart of Winter Haven! Welcome to 133 Rebecca Drive NE, a move-in-ready 3 bedroom, 2 bath home offering a private screened saltwater pool, important updates, comfortable living spaces, and an impressive combination of features and value. If you've been searching for an affordable Central Florida home where you can enjoy the Florida pool lifestyle right in your own backyard, this one deserves a closer look. Inside, the spacious main living area features attractive porcelain tile flooring, a vaulted ceiling, and a gas fireplace, creating a comfortable gathering space for everyday living and entertaining. The adjoining dining area provides direct access to the pool and outdoor living area, while the kitchen features clean white cabinetry, beautiful granite countertops, plenty of storage, and a full suite of included appliances. The desirable split-bedroom layout includes two comfortably sized guest bedrooms and a spacious primary suite with an en-suite bath and generously sized walk-in closet. Both bathrooms have been updated, including a beautifully renovated primary bath with a custom walk-in shower. Step outside and imagine weekends filled with pool time, grilling on the back deck, entertaining friends and family, and enjoying the Florida sunshine. The large screened outdoor living area features a private saltwater pool, plenty of deck space for lounging, dining, and grilling, plus a covered area where you can relax in the shade. Start the morning with coffee by the pool, spend a sunny afternoon in the water, then fire up the grill for dinner and enjoy a warm Florida evening at home. This is the kind of outdoor space that makes it easy to enjoy everything the Florida lifestyle is all about. Beyond the pool enclosure, the fully fenced backyard provides additional usable yard space with plenty of potential for landscaping, a vegetable garden, or your own collection of Florida fruit trees. An included storage shed provides convenient space for lawn and gardening equipment while keeping the two-car garage free for vehicles and additional storage. Major improvements include a NEW A/C system in 2025, all new double-pane windows and sliding glass door in 2021, a 2017 roof, newer front door, rain gutters and low utility bills. Best of all, there is NO HOA! Located in the heart of Winter Haven, you're convenient to downtown Winter Haven, Polk State College, shopping, dining, medical facilities, and recreation. Winter Haven's central location between Tampa and Orlando also puts theme parks, international airports, beaches, professional sports, and some of Central Florida's best entertainment within reach.

133 Rebecca Drive Ne, Winter Haven
$369,900
4 Beds ⋅ 3 Baths ⋅ Buckeye Pointe SubDv. ⋅ 33881 Zip Code
Welcome to 3035 Buckeye Point Drive, a beautifully refreshed pool home located in the desirable Buckeye Pointe community of Winter Haven. Offering 4 bedrooms, 3 bathrooms, and approximately 2,070 square feet of living space, this spacious home combines a functional layout, modern updates, and the Florida lifestyle buyers are looking for. The home has been freshly repainted inside and out, featuring a modern light gray exterior with crisp trim and a refreshed interior with light gray walls and bright trim throughout. The fresh finishes create a clean, updated, and move-in-ready feel from the moment you arrive. Inside, you'll find high ceilings and a spacious floor plan with plenty of room for everyday living, entertaining, family, and guests. Step outside to your private screened-in pool and enjoy your own backyard retreat—perfect for relaxing, entertaining, or enjoying Florida weather year-round. Located in Winter Haven, Buckeye Pointe offers convenient access to shopping, dining, schools, medical facilities, recreation, and major roadways connecting you throughout Central Florida. Whether you're looking for a primary residence, vacation home, or investment opportunity, this updated 4-bedroom, 3-bath pool home offers an excellent combination of space, comfort, location, and value. Don't miss the opportunity to make 3035 Buckeye Point Drive your own!

3035 Buckeye Pointe Drive, Winter Haven
$289,900
3 Beds ⋅ 2 Baths ⋅ Eloise Woods Lake Roy Unit SubDv. ⋅ 33884 Zip Code
Virtually Staged. Welcome to 112 Terrace Dr. in Winter Haven! Offering 2,091 square feet under roof, this beautifully refreshed three-bedroom, two-bathroom home is move-in ready and packed with updates throughout. From the moment you arrive, you’ll notice the upgraded landscaping, freshly painted exterior, new metal roof, and convenient covered carport. Step inside to a bright, welcoming interior featuring fresh paint, new flooring and baseboards throughout, new blinds, and upgraded lighting for a clean, modern finish. The kitchen is ready for everyday living and entertaining with solid-surface countertops, new appliances, and plenty of functionality, while the indoor laundry room located just off the kitchen adds extra convenience. The spacious primary bedroom features a true private en suite, while both bathrooms have been refreshed with updated finishes. Two additional bedrooms provide plenty of flexibility for family, guests, or a home office. Out back, the fully fenced yard offers plenty of room to spread out, entertain, grill, or create your own outdoor retreat. Whether hosting friends and family or simply enjoying a quiet Florida evening, there’s plenty of space to make it your own. With a NEW ROOF, updated interior and exterior finishes, new appliances, covered parking, and a spacious fenced backyard, 112 Terrace Dr. delivers an impressive combination of updates, space, and value. Schedule your private showing today and come see everything this Winter Haven home has to offer!

112 Terrace Drive, Winter Haven
$198,900
2 Beds ⋅ 2 Baths ⋅ Vienna Square SubDv. ⋅ 33884 Zip Code
Short Sale. CLOSE IN 60 DAYS OR LESS! QUICK and easy HECM Short Sale on this 2 bedroom 2 bath Vienna Square Villa with pond and wooded view. Located next door to the clubhouse! The charming kitchen has upgraded ivory cabinets, and quartz counter tops. The oak floors flow from the kitchen, and great room giving a warm quality finish. The roof was replaced in 2022. Sold strictly AS-IS. No renting for the 1st 2 years of ownership in this charming 55+ community. This home is conveniently located within 10 minutes of restaurants, banks, shopping and Legoland. Vienna Square offers a low-maintenance lifestyle with reasonable fees, in a welcoming setting. Vienna Square is a beautifully maintained, amenity-rich community designed for easy living. Monthly fees include exterior paint, roof replacement, irrigation water, basic yard maintenance, and a Spectrum Internet/TV package. Residents enjoy access to a community pool, fitness center, billiards, movie nights, tennis and pickleball courts, and an active social calendar. Step inside, fall in love. Make it yours!

1307 Innsbruck Ct, Winter Haven
$510,000
6 Beds ⋅ 4 Baths ⋅ Harrington A B Subdiviosion SubDv. ⋅ 33881 Zip Code
Newly Built Duplex in Winter Haven! This beautiful duplex features two spacious units, each offering 3 bedrooms and 2 bathrooms. Brand-new construction with modern finishes and a functional layout. The fully paved driveway maximizes parking for both units, providing ample space and convenience for residents and guests. Great opportunity for investors or owner-occupants seeking rental income. Conveniently located with easy access to shopping, dining, schools, and major roadways.

302 Avenue P Nw, Winter Haven
$249,000
3 Beds ⋅ 2 Baths ⋅ Florida Highland Co SubDv. ⋅ 33884 Zip Code
Welcome to your Home Sweet Home in Winter Haven, Florida! This 3-bedroom, 2-bath gem sits in the desirable Orchid Springs community, offering 1,571 sq. ft. of living space that's freshly painted inside and ready to move into. You'll notice the difference the moment you walk in. Bright, clean walls throughout give the whole home a crisp, updated feel. The layout flows easily between the living room, dining area, and kitchen, so you're never far from the action whether you're cooking, entertaining, or just hanging out. The kitchen has plenty of cabinet space and all the appliances you need, and the living room offers plenty of room to spread out and relax. The primary suite offers its own private retreat with an attached bath. Here's a bonus: there's an enclosed bonus space in the back of the home that works great as a 4th bedroom, home office, or flex room, giving you extra square footage you can make your own. Out back, you've got a patio surrounded by its own wall and enclosed with a screen, so you get real privacy while you enjoy your morning coffee or unwind after work. No nosy neighbors, no bugs, just your own outdoor space. Add in the 2-car garage for parking and storage, and this home checks a lot of boxes. Living in Orchid Springs also means access to the community pool and clubhouse, and the HOA even covers your lawncare, so you can enjoy a well-kept yard without lifting a finger. You're also close to shopping, dining, medical offices, Cypress Gardens Blvd, and US-27, so everything you need is within easy reach. Ready to call this your home? Reach out today to schedule your private tour!

271 Mariposa, Winter Haven
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