Winter Haven Homes with Pool Community Features

Winter Haven Homes with Pool Community Features

Welcome to Winter Haven, Florida, a charming city nestled in Polk County that perfectly embodies the essence of Central Florida living. Known for its picturesque lakes and vibrant community, Winter Haven offers an idyllic setting for families, retirees, and everyone in between. With its rich history, delightful parks, and a plethora of recreational activities, this city is not just a place to live; it’s a place to thrive.

One of the standout features of Winter Haven is its exceptional homes with pool community offerings. Imagine coming home to a serene oasis where you can unwind in your own private pool, perfect for those warm Florida days. These communities are designed with your lifestyle in mind, featuring beautifully landscaped surroundings, state-of-the-art amenities, and a strong sense of community. Whether you’re looking for a cozy single-family home or a spacious townhouse, there are plenty of options that cater to your preferences.

In addition to the allure of poolside living, Winter Haven boasts a variety of outdoor activities. With over 50 lakes, you can enjoy fishing, boating, and kayaking, or simply bask in the sun on one of the many scenic shorelines. The city is also home to the famous Legoland Florida Resort, making it an ideal spot for family fun.

With its delightful blend of relaxation and recreation, Winter Haven is not just a destination; it’s a community that welcomes you with open arms. Discover your dream home with a pool and experience the vibrant lifestyle that Winter Haven has to offer!

Newest Winter Haven Homes with Pool Community Features

no property photo
$275,000
3 Beds ⋅ 2 Baths ⋅ Villamar SubDv. ⋅ 33884 Zip Code
Under Construction. Brand new, energy-efficient home available by Jan 2027! Open floor plan with a lot of flexibility. Retreat to your primary suite that is conveniently situated in the back of the home for plenty of privacy and offers a huge walk-in closet and bathroom with dual sink vanity and standalone 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.

3941 Giorgio Drive, Winter Haven
150 El Dorado Unit 305, Winter Haven
$129,900
2 Beds ⋅ 2 Baths ⋅ The Hawaiian A Condominium Cond Bk 4 Pgs 29/32 Lyi SubDv. ⋅ 33884 Zip Code
Discover the perfect blend of comfort, convenience, and relaxed Florida living in this inviting 55+ community! Tucked away in a secluded setting, this beautifully updated third-floor corner condo offers privacy, welcoming spaces, and charming courtyard views. Ideally located near the elevators, this spacious 2-bedroom, 2-bathroom residence features an open-concept dining and living area, oversized bedrooms with walk-in closets, and a Florida room seamlessly opened to the family room—creating the perfect space to relax or entertain while enjoying the tranquil views below. The primary bedroom offers the convenience of an ensuite bathroom, while the second bathroom features a tub/shower combination. The updated interior boasts stainless steel appliances, including a gas range, and recessed lighting, adding a fresh, modern touch. Enjoy the convenience of assigned parking, including one covered space. Community laundry facilities are located on the second floor, with the option to install a washer and dryer in the primary bedroom closet, subject to HOA approval. Even better, the condo fees include water, sewer, trash, gas, internet, and cable, making budgeting that much easier! Offered furnished, this condo is move-in ready and makes an ideal vacation getaway or second home! Simply bring your suitcase and start enjoying the Florida lifestyle. Come discover the comfort, value, and convenience that make this condo a wonderful place to call home!

150 El Dorado Unit 305, Winter Haven
3946 Bedford Avenue, Winter Haven
$367,500
3 Beds ⋅ 2 Baths ⋅ Traditions Ph 02 SubDv. ⋅ 33884 Zip Code
Welcome to 3946 Bedford Avenue, located in Traditions at Lake Ruby, one of Winter Haven's premier gated 55+ communities! Built in 2018, this beautifully maintained home offers 3 bedrooms, 2 bathrooms, a spacious den/flex room, and an impressive three-car garage. Designed with both comfort and entertaining in mind, the home features an inviting open-concept floor plan with a generous great room that flows seamlessly onto an oversized screened patio overlooking the beautifully landscaped backyard. This expansive outdoor living space is perfect for relaxing, entertaining guests, or simply enjoying Florida living. The well-appointed kitchen features 42-inch white shaker cabinetry, quartz countertops, stainless steel appliances, and a large center island with seating. Whether hosting a dinner party or enjoying a casual meal, you'll appreciate the flexibility of the formal dining room, breakfast nook, and island seating. The spacious primary suite offers a large walk-in closet and an ensuite bathroom complete with dual vanities, an oversized walk-in shower, and a private water closet. Two additional bedrooms and a generously sized den provide plenty of room for guests, hobbies, or a home office. The dedicated laundry room features additional cabinetry for convenient storage. Additional highlights include beautiful plantation shutters throughout the home, a whole-house water softener, tile flooring throughout the main living areas, carpeting in the bedrooms, and an interior that was freshly painted just one year ago. The oversized three-car garage features an attractive epoxy floor finish, and plenty of room for vehicles, storage, or a workshop. The garage also has a retractable screen door. One of the greatest advantages of living in Traditions at Lake Ruby is the low-maintenance lifestyle! The HOA takes care of lawn maintenance and exterior house painting while also providing cable TV and Wi-Fi. Residents enjoy access to an extensive collection of community amenities, making it easy to stay active, socialize, or simply relax and enjoy the Florida lifestyle.

3946 Bedford Avenue, Winter Haven
807 Eagle Pond Drive Unit 807, Winter Haven
$159,000
2 Beds ⋅ 2 Baths ⋅ Eagle Pond Condo SubDv. ⋅ 33884 Zip Code
Enjoy peaceful pond views from this beautifully situated second story condo in Winter Haven! This inviting unit features wood-look tile flooring, granite kitchen countertops, indoor laundry, and a 2017 HVAC system. Step outside and take in relaxing water views, or enjoy the community amenities that include: A swimming pool, 24-hour guarded security, fitness center, and tennis courts. Centrally located in the heart of Florida, between Tampa and Orlando, this condo offers convenient access to shopping, dining, entertainment, and major attractions. Whether you're looking for a full-time residence, seasonal getaway, or investment opportunity, this condo offers comfortable living and convenient community amenities in a desirable Winter Haven location!

807 Eagle Pond Drive Unit 807, Winter Haven
3123 Laurel Oak Ln, Winter Haven
$315,000
4 Beds ⋅ 2 Baths ⋅ Villamar Ph 6 & Ph 6d SubDv. ⋅ 33884 Zip Code
Short Sale. A Must-See! Beautifully designed 4-bedroom, 2-bathroom home with a 2-car garage, presenting 1,983 square feet of living space with a bright and airy open floor plan and high ceilings. Perfect for families or anyone who loves to entertain, this home seamlessly blends style, comfort, and functionality. The kitchen boasts ample counter space, a breakfast bar, stainless steel appliances, solid wood cabinets, and even a pantry. Strategically located just off the kitchen, the laundry room offers additional storage space. Enjoy gorgeous, durable vinyl flooring throughout the main living areas and cozy carpet in the bedrooms for ultimate comfort. The expansive primary bedroom highlights a walk-in closet and en suite bathroom complete with a double vanity and large step-in shower. The welcoming, screened-in front porch and lovely landscaping provide great curb appeal. Step out back through sliding glass doors to a second screened porch overlooking the fenced-in backyard, great for relaxing, weekend gatherings, or enjoying your morning coffee. Located in Villamar! Low annual HOA fee; the amenities include a community pool at the main entrance of the neighborhood on Cunningham Dr., along with a playground. This pristine home is ready to welcome its next owners. Don't miss the opportunity to make this beautiful home yours!

3123 Laurel Oak Ln, Winter Haven
3099 Captain Jax Way, Winter Haven
$205,090
3 Beds ⋅ 3 Baths ⋅ Serenity At Peace Creek Th SubDv. ⋅ 33884 Zip Code
Under Construction. This new two-story townhome offers ample space to live and grow with a total of three bedrooms. The first level features a spacious and flexible open-concept layout shared between the kitchen, dining room and family room, maximizing the interior living space. Two secondary bedrooms and a lavish owner’s suite featuring a full bathroom comprise the second floor. Serenity at Peace Creek Reserve is a masterplan community of new townhomes with a beautiful natural creek. Winter Haven is the chain of lakes city, with over 26 linked together by a canal. There are lots of shops, restaurants, and bike paths. Peace Creek Reserve is what you have been looking for. A safe small town feel with convenience, the perfect place to raise a family.

3099 Captain Jax Way, Winter Haven
188 Morning Dew Court, Winter Haven
$295,000
3 Beds ⋅ 2 Baths ⋅ Morningside Ph 02 SubDv. ⋅ 33884 Zip Code
Virtually Staged. Welcome to 188 Morning Dew Court, where comfort, style, and the Florida lifestyle come together in the gated Winterset community! Nestled on a quiet cul-de-sac, this Mediterranean-style home offers 3 spacious bedrooms, 2 bathrooms, a 2-car garage, and 1,730 square feet of thoughtfully designed living space. Step inside to discover an inviting open-concept floor plan featuring soaring vaulted ceilings, beautiful oak wood flooring, and abundant natural light. The spacious living area flows seamlessly into the kitchen, complete with granite countertops, ample cabinetry, and a charming breakfast nook. A separate dining area provides additional space for entertaining. The desirable split-bedroom layout offers added privacy, with a generous primary suite featuring a walk-in closet, dual vanities, a relaxing jacuzzi garden tub, and a separate walk-in shower. Two additional bedrooms provide flexibility for guests, a home office, or hobbies. Enjoy Florida's beautiful weather from your enclosed rear lanai. But the lifestyle doesn't stop at your front door! Morningside at Winterset offers outstanding community amenities, including a clubhouse with lounge, swimming pool, hot tub, tennis courts, pickleball courts, and shuffleboard. Love the water? Residents enjoy a private community boat ramp and fishing pier on Lake Winterset, providing access to Winter Haven's renowned Chain of Lakes. Whether boating, fishing, relaxing poolside, or enjoying a friendly game of pickleball, there's something for everyone! Conveniently located near shopping, dining, entertainment, and LEGOLAND Florida Resort, this home offers a wonderful combination of tranquility and convenience. Why settle for just a home when you can enjoy an entire resort lifestyle? Schedule your private showing today!

188 Morning Dew Court, Winter Haven
2097 Whispering Trails Boulevard, Winter Haven
$410,000
4 Beds ⋅ 3 Baths ⋅ Whispering Trails Ph 01 SubDv. ⋅ 33884 Zip Code
Discover your ideal Florida retreat in this beautifully maintained, gated Winter Haven neighborhood! Perfectly situated close to shopping centers for effortless errands, just 10 minutes from the exciting attractions of Legoland, and less than an hour from the Walt Disney World. Tampa is also within a convenient 1-hour drive, offering additional entertainment and amenities. This charming home comes move-in ready, including all essential appliances such as a range, refrigerator, microwave, garbage disposal. The secure, gated community offers peace of mind and added privacy, making it an ideal place to call home. Whether you're looking for a primary residence, vacation home, or investment property, this residence offers comfort, convenience, and easy access to some of Florida’s top attractions. Don’t miss your chance to own this fantastic 4 bed 3 full bath pool home in the fast-growing City of Winter Haven!

2097 Whispering Trails Boulevard, Winter Haven
4000 Giorgio Drive, Winter Haven
$325,000
4 Beds ⋅ 3 Baths ⋅ Villamar SubDv. ⋅ 33884 Zip Code
Brand new, energy-efficient home available by Dec 2026! First-floor primary suite ensures everyone has their own private space. Second floor offers a spacious loft that can be used to best fit your family's needs. Enjoy preparing meals with your family in the open kitchen with spacious work island. 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.

4000 Giorgio Drive, Winter Haven
1550 11th Street Ne Unit C5, Winter Haven
$115,000
2 Beds ⋅ 2 Baths ⋅ Lake Buckeye Condo SubDv. ⋅ 33881 Zip Code
This updated unit has 1,148 sq ft of living space, with new flooring, new countertops and plenty of natural light throughout. The kitchen has a large pantry, and the washer and dryer are in the unit. Step out onto the balcony for direct views over Lake Buckeye. Both bedrooms are a good size with large closets, and the primary bedroom has its own private bathroom. Residents can use the community pool. The unit is currently leased at $1,150 a month, and the lease continues after closing, so the buyer takes over an existing tenancy and income from day one. Showings are by appointment only, with notice to the tenant. Information is deemed reliable but not guaranteed. Buyer to verify square footage, lease terms, HOA fees and rules, and all other details.

1550 11th Street Ne Unit C5, Winter Haven
4157 Rolling Oaks Drive, Winter Haven
$118,000
2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv. ⋅ 33880 Zip Code
Welcome to this well-maintained 2-bedroom, 2-bath home located in the desirable community of Oakwood Estates in Winter Haven. This home offers a peaceful, well-kept neighborhood. The roof is approximately 5 years old, offering added value and peace of mind. No lot rent—ownership includes the land, with only a low monthly HOA fee. Oakwood Estates is a gated 55+ community offering resort-style amenities including clubhouses, heated pools, fitness center, shuffleboard, tennis courts, and a full calendar of activities. Conveniently located near shopping, dining, medical facilities, and major roadways. Schedule your private showing today and experience easy living in this vibrant community.

4157 Rolling Oaks Drive, Winter Haven
3403 Julius Estates Boulevard, Winter Haven
$349,000
4 Beds ⋅ 3 Baths ⋅ Lake Smart Estates SubDv. ⋅ 33881 Zip Code
Enjoy comfortable living in this spacious home offering just under 2,400 square feet of living space in a convenient North Winter Haven location. Situated directly across from the community swimming pool, newly replaced AC this home offers easy access to neighborhood amenities, including a fishing pier. The backyard features a peaceful view overlooking a small pond, creating a relaxing setting to enjoy your outdoor space. The thoughtfully designed floor plan features an open and inviting downstairs living area with the living room, kitchen, and family room, while all bedrooms are conveniently located upstairs, providing added privacy. The kitchen is appointed with granite countertops, and the home also features a two-car garage and the added convenience of an upstairs laundry area with washer and dryer included. With quick access to Highway 27, getting around Winter Haven and the surrounding areas is a breeze. Enjoy the combination of spacious living, community amenities, peaceful water views, and a convenient location in this inviting home!

3403 Julius Estates Boulevard, Winter Haven
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