Winter Haven Homes for Sale

Winter Haven Homes for Sale

Welcome to Winter Haven, Florida—a charming city nestled in the heart of Polk County, known for its stunning lakes, vibrant community, and a rich tapestry of recreational activities. With its picturesque landscapes and friendly atmosphere, Winter Haven offers an inviting blend of small-town charm and modern conveniences, making it an ideal place to call home.

Winter Haven is famously known as the "Chain of Lakes City," boasting over 50 sparkling lakes that provide ample opportunities for boating, fishing, and enjoying the great outdoors. The city's beautiful parks and walking trails enhance its appeal, offering residents numerous options for outdoor activities and family fun. Whether you're looking to explore the scenic beauty of Lake Howard or indulge in a leisurely stroll through the historic downtown, Winter Haven has something for everyone.

For those considering a move, the real estate market in Winter Haven is thriving, with a diverse array of homes for sale that cater to various lifestyles and budgets. From charming single-family homes nestled in quiet neighborhoods to modern townhouses and spacious waterfront properties, you'll find a perfect fit for your needs. The city's affordable housing options make it an attractive choice for first-time buyers, growing families, and retirees alike.

With a strong sense of community, excellent schools, and a variety of local amenities, Winter Haven is not just a place to live—it's a place to thrive. Discover the beauty and warmth of Winter Haven, and let it be the backdrop for your next chapter. Explore our listings today and find your dream home in this delightful Florida gem!

Newest Winter Haven Homes for Sale

$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
$315,000
4 Beds ⋅ 3 Baths ⋅ Villamar Ph 2 SubDv. ⋅ 33884 Zip Code
Designed around connected gathering spaces and an easy single-story layout, this 1,988-square-foot home offers a comfortable balance of openness and separation throughout. The kitchen sits at the center of the home, where granite counters, a large island with seating, stainless-steel appliances, and a walk-in pantry create a practical workspace while keeping the kitchen connected to the dining area and great room. Sliding glass doors extend the main living space toward the backyard, bringing in natural light and making it easy to move between indoor and outdoor areas. The four-bedroom, three-bath layout provides flexibility without sacrificing privacy, with the primary suite positioned toward the rear of the home and complemented by a walk-in closet and en suite bath with dual sinks and a glass-enclosed shower. Ceramic tile runs through the main living spaces, while carpet adds a softer finish to the bedrooms. An interior laundry room, attached two-car garage, paver driveway, irrigation system, and backyard add to the home’s everyday functionality. Built in 2021 and maintained with its original finishes, the home offers a functional, well-connected layout with room for the next owner to make it their own. Beyond the home, VillaMar offers a community pool, playground, sidewalks, and recreational common areas, giving residents additional ways to enjoy time outside close to home. Its Winter Haven location also keeps shopping, dining, major roadways, and area attractions within convenient reach.

1166 Yumuri Street, Winter Haven
$450,000
3 Beds ⋅ 3 Baths ⋅ Lake Thomas Woods Eighth Add SubDv. ⋅ 33880 Zip Code
**Listed $5,000 below Appraisal Value** Welcome to this spacious 3-bedroom, 2.5-bath home offering 2,352 square feet of living space on a generous .33-acre lot tucked away on a quiet cul-de-sac. Designed for both comfortable everyday living and entertaining, this home offers plenty of space inside and out. One of the standout features is the massive bonus room with its own private entrance and an impressive feature wall complete with a waterfall—perfect for a game room, home office, media room, entertaining space, or whatever fits your lifestyle. The kitchen features solid wood cabinetry, granite countertops and plenty of workspace, while the separate dining room provides the perfect setting for meals and gatherings. A large living room, tray ceilings and tile flooring throughout add to the home's spacious feel. The primary suite includes a cedar-lined walk-in closet and an ensuite bath with a walk-in shower. Two additional bedrooms and 1.5 additional baths provide plenty of room for family and guests. Step outside and you'll quickly see why the backyard may become your favorite part of the home! Enjoy the recently resurfaced saltwater pool, expansive lanai and covered 14' x 14' pavilion—ideal for grilling, entertaining or simply relaxing by the pool. Paved walkways and decking surround the property, creating multiple outdoor spaces to enjoy. With over a third of an acre, a cul-de-sac location, a saltwater pool, incredible bonus room and more than 2,350 square feet of living space, this home offers a combination of space, character and indoor/outdoor living that's ready for its next owner.

205 Thomas Court, Winter Haven
$260,000
3 Beds ⋅ 2 Baths ⋅ Lakes/Lucerne Park Ph 4 SubDv. ⋅ 33881 Zip Code
Virtually Staged. Short Sale. Welcome to 573 Lucerne Blvd, a well-maintained single-story home offering 4 bedrooms and 2 bathrooms with a comfortable layout designed for everyday living. Recent improvements provide added peace of mind, including an HVAC system installed in 2018, updated flooring in the main living areas in 2018, interior paint completed in 2019, and exterior paint refreshed in 2024. The single-level floor plan offers flexibility and convenience, making this home a great opportunity for a variety of buyers. This is a short sale and is not lender approved. All terms and conditions of the sale, including the final purchase price, are subject to lender approval. Buyer and buyer’s agent are responsible for conducting their own due diligence.

573 Lucerne Boulevard, Winter Haven
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