Winter Haven Homes with HOA Yes/No

Winter Haven Homes with HOA Yes/No

Welcome to Winter Haven, a charming city located in Polk County, Florida. Known for its picturesque lakes and vibrant community, Winter Haven offers a perfect blend of natural beauty and modern amenities.

For those looking to settle down in Winter Haven, you'll find a variety of housing options to suit your needs. Whether you prefer a home with an HOA or without, Winter Haven has something for everyone.

Homes with HOA provide residents with added benefits such as community maintenance, amenities like pools or gyms, and a sense of community. On the other hand, if you prefer more independence and flexibility with your property, there are plenty of homes available without an HOA in Winter Haven.

No matter your preference, Winter Haven offers a high quality of life with access to top-rated schools, beautiful parks, and a thriving downtown area. With a rich history and a strong sense of community, Winter Haven is the perfect place to call home.

Discover the beauty and charm of Winter Haven and find your dream home in this wonderful city in Central Florida.

Newest Winter Haven Homes with HOA Yes/No

$330,900
4 Beds ⋅ 4 Baths ⋅ Villamar SubDv. ⋅ 33884 Zip Code
Under Construction. New construction home with 2227 square feet on two-story including 4 bedrooms with loft, 3.5 baths, and an open living area. Enjoy an open kitchen with Quartz countertops, Samsung stainless steel appliances, a walk-in pantry, and a spacious island, fully open to the dining café and gathering room. The living area, laundry room, and baths include luxury wood vinyl plank flooring, with stain-resistant carpet in the bedrooms. Your owner's suite is complete with a walk-in wardrobe and a private en-suite bath with dual vanities, and a tiled shower. Bedrooms 2 and 3 share a jack-and-Jill bathroom. Plus, enjoy a covered lanai, 2-car garage, custom-fit window blinds, architectural shingles, energy-efficient insulation and windows, and a full builder warranty. “Please note, virtual tour/photos showcases the home layout; colors and design options in actual home for sale may differ. Furnishings and decor do not convey."

4498 Rapallo Avenue E, Winter Haven
$749,000
3 Beds ⋅ 4 Baths ⋅ Cypresswood Palma Ceia SubDv. ⋅ 33884 Zip Code
Meticulously maintained and beautifully remodeled, this exceptional Palma Ceia residence in Cypresswood offers pond frontage, three private en-suite bedrooms, a dedicated office, a heated swimming pool, and incredible golf course views. The pavered driveway and walkways, manicured flower gardens, and a 2022 black metal roof set the stage for the impressive interior. Elevated ceilings, crown molding, waterproof Pergo flooring, stone counters, and plantation shutters are just a few of the home’s stunning features. At the heart of the home is a spacious great room featuring a natural gas fireplace with shiplap façade. Triple sliding glass doors, with new screens, create a seamless indoor-outdoor flow to the covered lanai and pool area while showcasing the outdoor views. The updated kitchen features quartz counters, an island with a prep sink and filtered water, a Kohler workstation sink, breakfast bar, stainless appliances, double ovens, gas range, Bosch dishwasher, and a spacious dinette overlooking the pool. A private office provides the perfect setting for working from home. Designed to give everyone their own space, the home offers three bedrooms with en-suite bathrooms. The primary suite includes pool access, a tray ceiling, two walk-in closets with built-in shelving, and a gorgeous remodeled bathroom featuring a six-foot freestanding soaking tub, glass-enclosed walk-in shower, dual vanities, and a water closet. The second bedroom includes an equally impressive en-suite bath with custom tile flooring, a granite counter, tub, and separate walk-in shower. Located at the rear of the home, the third en-suite bedroom is ideal for visiting guests and can be closed off with a pocket door for added privacy. Its bathroom offers a granite counter with dual sinks, a tub and shower combo, and a linen closet. An additional linen closet is located in the guest-wing hallway. The interior laundry room provides a closet pantry, storage closet, and convenient half bathroom. Florida living takes center stage outdoors with a screen-enclosed heated pool, expansive covered lanai, and a separate screened area for sunning. The peaceful setting overlooks the pond and third hole of the golf course, where a variety of birds and wildlife can be enjoyed daily. Meticulously designed gardens, window planter boxes and a pavered sitting area near the pond—ideal for a fire pit—complete this private outdoor oasis. The two-car garage features an epoxy floor, utility sink, storage closets, and overhead storage racks. Additional improvements and features include a 2026 installed gas water heater, a 26-gauge standing seam metal roof (2022) with a 40-year warranty, dual-zone air conditioning (2020), irrigation on separate meter, plantation shutters throughout, remote-controlled lanai lighting, pool safety fence, Ring cameras, rain gutters, and more. Located within the guarded Cypresswood community, this remarkable home combines thoughtful updates, exceptional care, abundant privacy, and a truly beautiful golf course and waterfront setting. Cypresswood Golf & Country Club features an 18-hole championship golf course, driving range, pro shop, jr. olympic pool, tennis & pickleball courts, an event venue, a sports pub and more. Located just minutes from shopping, medical facilities and downtown Winter Haven. Centrally located between Tampa and Orlando with easy commutes to airports and beaches. Come see what this magnificent home and community in Central FL has to offer!

4040 Palma Ceia Circle, Winter Haven
$396,140
4 Beds ⋅ 3 Baths ⋅ Villamar SubDv. ⋅ 33884 Zip Code
Under Construction. Brand new, energy-efficient home available by Aug 2026! An open floorplan that makes entertaining easy in the open kitchen, dining, and great room that flow to the patio. The primary suite is tucked in the rear of the home offering plenty of privacy and features a spacious walk-in closet and shower. Visit Villamar and explore new single-family homes for sale in Winter Haven, FL. Residents will have access to two resort-style amenity centers featuring a clubhouse, pool, and playground. Winter Haven is known for its beautiful chain of lakes with lakeside restaurants and its award-winning community theater. Nearby attractions include Legoland Florida and Peppa Pig Theme Park. A brand-new model and new phase are coming soon. Each of our homes is built with innovative, energy-efficient features designed to help you enjoy more savings, better health, real comfort and peace of mind.

3757 Giorgio Drive, Winter Haven
$296,630
3 Beds ⋅ 2 Baths ⋅ Villamar SubDv. ⋅ 33884 Zip Code
Under Construction. Brand new, energy-efficient home available by Aug 2026! Prepare dinner while catching up on the days events from this homes chef-inspired kitchen which overlooks a great room and dining area. Well appointed primary suite provides a restful retreat at the end of the day and has a spacious walk-in closet. Visit Villamar and explore new single-family homes for sale in Winter Haven, FL. Residents will have access to two resort-style amenity centers featuring a clubhouse, pool, and playground. Winter Haven is known for its beautiful chain of lakes with lakeside restaurants and its award-winning community theater. Nearby attractions include Legoland Florida and Peppa Pig Theme Park. A brand-new model and new phase are coming soon. Each of our homes is built with innovative, energy-efficient features designed to help you enjoy more savings, better health, real comfort and peace of mind.

3968 Giorgio Drive, Winter Haven
$125,000
2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv. ⋅ 33880 Zip Code
A Home That's Ready When You Are — Oakwood Estates, Winter Haven Some of life's best decisions are also the simplest ones. This lovingly maintained, fully furnished manufactured home in Oakwood Estates invites you to skip the hassle and step straight into the lifestyle you've been looking forward to — because everything has already been taken care of, and everything stays. Fresh interiors, thoughtful updates, and a warm, welcoming layout make this one of the most effortless purchases you'll make. Step inside and you're immediately greeted by natural light pouring through double-pane windows, setting a bright, airy tone throughout. The kitchen shines with stainless steel appliances, wood-look countertops, a newer sink, and crisp white cabinetry — and yes, everything stays, right down to the air fryer. The dining area features beautiful built-in cabinetry and shelving, flowing seamlessly into a spacious living room complete with an electric reclining sofa, flat screen TV, and comfortable seating. Luxury vinyl plank flooring runs throughout, tying it all together with style and ease of maintenance. Both bedrooms are generously sized and fully furnished. The primary suite features a walk-in closet, electric reclining bed, and a quality foam mattress. The Florida room offers updated ceiling fans, a brand-new AC unit, and convenient access to the in-home washer and dryer hookups — a true bonus in this community. Slide open the door to the enclosed lanai and enjoy your morning coffee overlooking lush, manicured landscaping — your own quiet corner of Florida. Additional highlights include hurricane shutters, vinyl siding, a 2017 roof, an irrigation system, and an updated electrical panel for peace of mind. Then there's the community. Oakwood Estates is a gated, beautifully maintained 55+ resident-owned community in the heart of Winter Haven — one of Polk County's most desirable areas. Residents enjoy two heated pools, two clubhouses, tennis and pickleball courts, shuffleboard, bocce ball, a miniature golf course, horseshoes, a fishing lake with pier, RV and boat storage, a library and activities center, pool tables, and a vibrant, active activities committee that keeps the social calendar full year-round. Lighted streets, underground utilities, and security cameras throughout the common areas reflect a community that takes pride in where it lives. This is Florida living, fully loaded and ready to go.

4332 Cherrywood Street, Winter Haven
$70,000
2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv. ⋅ 33880 Zip Code
New Carpet throughout most of the home. Plus many of the windows have been updated to thermal pane insulated windows. If that is not enough the TPO roof was installed in December 2023. The home has a nice layout with a huge primary bedroom with huge walk in closet. Location is convenient in Oakwood Estates, a 55+ community, right across from the office and close proximity to one of the pools. Enjoy the many amenities at Oakwood including two pool, two clubhouses, miniature golf, fishing pier, shuffleboard and much, much more. Join in on the many activities including weekly Koffee Klatch, potluck meals, and dances. The two heated pools offer many hours of relaxation. Or just sit out on the screened front porch and watch the world go by. This home is priced to sell. Check it out today!!

4027 Rolling Oaks Drive, Winter Haven
$619,000
5 Beds ⋅ 3 Baths ⋅ Hidden Creek SubDv. ⋅ 33880 Zip Code
Virtually Staged. Welcome to this stunning 5-bedroom, 3-bathroom pool residence located in the highly sought-after, gated Hidden Creek community of Winter Haven. Perfectly positioned just minutes from the Polk Parkway and LEGOLAND Florida Resort, and conveniently situated between Lakeland and Winter Haven, this home offers an ideal blend of comfort and unbeatable accessibility. Inside, you will find soaring ceilings, a smart split-floor plan, a dedicated office or bonus room, a large den, and a 2-car garage that delivers ultimate flexibility for modern living, complemented by brand-new carpet replaced in 2025. The beautiful kitchen features granite countertops and a convenient walk-in pantry, while the primary suite serves as a true private retreat featuring a deep soaking tub, separate walk-in shower, dual sinks, a vanity, and a massive walk-in closet. Situated on a generous 0.35-acre lot, the property offers rare privacy, as the home backs up to a preserve with peaceful natural views. The absolute crown jewel of the home is the expansive, screen-enclosed lanai and sparkling saltwater pool with a heated spa, creating an exceptional resort-style outdoor living space masterfully designed for effortless entertaining, relaxing weekend lounging, or simply enjoying the tranquil Florida breeze in total privacy. Schedule your private showing today and discover a rare gem in Winter Haven!

1020 Lena Run Court, Winter Haven
$292,900
3 Beds ⋅ 2 Baths ⋅ Villamar Phase 6 And Phase 6d SubDv. ⋅ 33884 Zip Code
Under Construction. *Photos are of similar model but not that of the exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability, and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

3740 Giorgio Drive, Winter Haven
$279,900
4 Beds ⋅ 2 Baths ⋅ Villamar Phase Iv SubDv. ⋅ 33884 Zip Code
Virtually Staged. Welcome to 2638 San Marco Way in Winter Haven, where modern style, functional design, and exceptional value come together in this beautifully appointed - built in 2023 - 4-bedroom, 2-bathroom home. Offering a spacious open-concept floor plan, this home, is designed for both everyday living and effortless entertaining. Step inside to find luxury vinyl plank flooring throughout the main living areas with comfortable carpet in the bedrooms. The heart of the home is the stunning kitchen, featuring solid surface countertops, stainless steel appliances, an oversized island, abundant cabinet space, and a large walk-in pantry—perfect for the home chef and those who love to entertain. Just off the kitchen, you'll appreciate the dedicated indoor laundry room complete with a convenient drop-zone counter to help keep everyday life organized. The spacious primary suite serves as a private retreat with a true en-suite bathroom offering dual vanities, a relaxing garden tub, separate walk-in shower, and an oversized walk-in closet. Upgraded lighting and ceiling fans throughout the home add a modern touch, while the attached two-car garage provides plenty of storage. With a low HOA, thoughtful layout, and move-in-ready finishes, this home offers incredible value in one of Winter Haven's growing communities. Conveniently located near shopping, dining, schools, and area attractions, this is the perfect opportunity to enjoy Florida living at its best.

2638 San Marco Way, Winter Haven
$294,990
4 Beds ⋅ 2 Baths ⋅ Villamar Phase 6 And Phase 6d SubDv. ⋅ 33884 Zip Code
Pre-Construction. To be built. Introducing the Harper floorplan at Villamar, where every square foot is put to use with sophistication and comfort. Inside this 4 bedroom, 2 bathroom home, you’ll find 1,665 square feet of comfortable living. This meticulously designed residence combines modern convenience with timeless elegance, showcasing granite and tile floors throughout. As you step inside, you are greeted by an inviting foyer that leads you into the heart of the home. The open-concept layout seamlessly connects the living room, dining area, and kitchen, creating a perfect space for entertaining family and friends. The spacious living room features abundant natural light, thanks to large windows that provide picturesque views of the surrounding landscape. With ample room for seating, it's an ideal spot for relaxation and gatherings. The chef's kitchen is a true highlight, boasting granite countertops, sleek stainless steel appliances, and an oversized island with a breakfast bar. Whether you're preparing a casual meal or hosting a formal dinner, this kitchen is well-equipped to meet your culinary needs. The four generously sized bedrooms have flexibility for various lifestyles. The primary suite is a tranquil retreat, featuring a private ensuite bathroom with dual sinks, a separate shower, and a walk-in closet. The remaining three bedrooms share one well-appointed bathroom, making morning routines a breeze. Like all homes in Villamar, the Harper includes all concrete block and also smart home technology, which allows you to control your home anytime with your smart device while near or away. Whether you're seeking a peaceful family retreat or a stylish place to call your own, this home is sure to meet your every need. Contact us today and find your home at Villamar. *Photos are of similar model but not that of the exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability, and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

4053 Giorgio Drive, Winter Haven
$275,900
3 Beds ⋅ 2 Baths ⋅ Villamar Phase 6 And Phase 6d SubDv. ⋅ 33884 Zip Code
Under Construction. The Allex II is one of our one-story floorplans featured in Villamar in Winter Haven, Florida. With 2 exteriors to choose from, the Allex is sure to turn heads. Inside this 3-bedroom, 2-bathroom home, you’ll find 1,504 square feet of comfortable living. The living area is an open concept, where your kitchen, living, and dining areas blend seamlessly into a space perfect for everyday living and entertaining. Relax on the covered lanai looking out to your backyard. The kitchen features quartz countertops, stainless-steel appliances and a walk-in pantry which are sure to both turn heads and make meal prep easy. You’ll never be too far from the action with the living and dining area right there. In every bedroom you’ll have carpeted floors and a closet in each room. Whether these rooms become bedrooms, office spaces, or other bonus rooms, there is sure to be comfort. The primary bedroom located in the rear of the home has its own attached bathroom that features a walk-in closet and all the space you need to get ready in the morning. Sharing a sink isn’t a worry with the double vanity. Like all homes in Villamar, the Allex II includes all concrete block and also smart home technology, which allows you to control your home anytime with your smart device while near or away. *Photos are of similar model but not that of the exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability, and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

4052 Giorgio Drive, Winter Haven
$283,900
3 Beds ⋅ 2 Baths ⋅ Villamar Phase 6 And Phase 6d SubDv. ⋅ 33884 Zip Code
Pre-Construction. To be built. The Allex II is one of our one-story floorplans featured in Villamar in Winter Haven, Florida. With 2 exteriors to choose from, the Allex is sure to turn heads. Inside this 3-bedroom, 2-bathroom home, you’ll find 1,504 square feet of comfortable living. The living area is an open concept, where your kitchen, living, and dining areas blend seamlessly into a space perfect for everyday living and entertaining. Relax on the covered lanai looking out to your backyard. The kitchen features quartz countertops, stainless-steel appliances and a walk-in pantry which are sure to both turn heads and make meal prep easy. You’ll never be too far from the action with the living and dining area right there. In every bedroom you’ll have carpeted floors and a closet in each room. Whether these rooms become bedrooms, office spaces, or other bonus rooms, there is sure to be comfort. The primary bedroom located in the rear of the home has its own attached bathroom that features a walk-in closet and all the space you need to get ready in the morning. Sharing a sink isn’t a worry with the double vanity. Like all homes in Villamar, the Allex II includes all concrete block and also smart home technology, which allows you to control your home anytime with your smart device while near or away. *Photos are of similar model but not that of the exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability, and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

4811 Khloe Court, Winter Haven
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