Winter Haven Homes with Community Pool type

Winter Haven Homes with Community Pool type

Welcome to Winter Haven, Florida—a charming city nestled in the heart of Polk County, known for its picturesque lakes and vibrant community spirit. With a rich history dating back to the early 1900s, Winter Haven has blossomed into a thriving hub for families, retirees, and everyone in between. The city is renowned for its stunning chain of lakes, offering endless opportunities for fishing, boating, and enjoying the great outdoors.

Winter Haven is also home to a variety of amenities, including shopping centers, delicious dining options, and recreational parks, ensuring that residents have everything they need right at their fingertips. The city’s warm climate allows for year-round outdoor activities, making it a perfect place for those who love sunshine and fresh air.

One of the standout features of Winter Haven’s real estate market is the availability of homes with community pools. Imagine relaxing on a sunny afternoon, surrounded by friendly neighbors, with the shimmering water inviting you to take a refreshing dip. These homes not only provide a perfect retreat for families and friends but also foster a sense of community and connection among residents.

Whether you're looking for a cozy single-family home or a spacious townhouse, Winter Haven offers a variety of options with access to beautiful community pools. Dive into the lifestyle you’ve always dreamed of in Winter Haven, where comfort meets community, and every day feels like a vacation. Come explore the possibilities and make this delightful city your new home!

Newest Winter Haven Homes with Community Pool type

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
2747 San Marco Way, Winter Haven
$289,990
3 Beds ⋅ 2 Baths ⋅ Villamar Ph 5 SubDv. ⋅ 33884 Zip Code
The Vista is a thoughtfully designed single-story home in the sought-after Villamar community, featuring three bedrooms, two full bathrooms, and an inviting open-concept layout that blends modern style with everyday functionality. From the moment you step inside, the well-planned interior and carefully selected finishes create a welcoming feel throughout. At the heart of the home, the spacious kitchen showcases quartz countertops, a full line of stainless steel appliances, including an eSTAR® side-by-side refrigerator, and an oversized island that provides additional seating and workspace. The kitchen flows seamlessly into the dining area and expansive Great Room, creating an open, connected living space. Just off the Great Room, a covered lanai extends the living area outdoors, providing a comfortable setting to enjoy the surrounding views. The private owner's suite is tucked away at the rear of the home and features a generous walk-in closet and an en-suite bathroom with dual vanities and a beautifully tiled shower with glass enclosure. Two additional bedrooms are positioned at the front of the home, along with a full bathroom and convenient linen closet. A dedicated laundry room, complete with an already installed washer and dryer, adds another thoughtful touch. Ceramic tile flows throughout the main living areas, while carpeting adds comfort in all three bedrooms. Smart home technology includes a Ring Video Doorbell, Smart Thermostat, Keyless Entry Smart Door Lock, and DEAKO Smart Switches. Additional features include lush landscaping, a front irrigation system, architectural shingles, insulated windows, and a two-car garage, all backed by a full builder warranty. Villamar is one of the area's premier communities, featuring an impressive collection of amenities, including a resort-style swimming pool with a dedicated lap lane, expansive pool deck with shaded seating, stylish clubhouse, playground and park area, dog park, walking paths, and beautifully maintained green spaces. Tranquil ponds, wetlands, and waterfront and conservation homesites further enhance the community's natural surroundings. Move-in ready and thoughtfully appointed throughout, The Vista brings together an appealing open layout, stylish finishes, smart home technology, and desirable community amenities. Schedule your private showing today! We can’t wait to welcome you home!

2747 San Marco Way, Winter Haven
2332 Salzburg Loop, Winter Haven
$244,900
2 Beds ⋅ 2 Baths ⋅ Vienna Square SubDv. ⋅ 33884 Zip Code
PICTURE PERFECT! Imagine settling into this ideal low-maintenance home tailored for comfort and easy living. This 2 bedroom, 2 bathproperty is clean, move-in ready, and designed to let you spend less time on chores and more time enjoying your time.Highlights include: - Spacious Eat-In Kitchen: Features lovely granite countertops, a travertine backsplash, and an attractive black appliance package. - Bright & Open Layout: An easy floor plan with modern, low-maintenance luxury vinyl plank floors throughout the main living areasand bedrooms, plus an extra-large laundry room. - Private Outdoor Space: Enjoy a screened patio complete with slate tile floors, a ceiling fan, and roller shades for quiet privacy. - Peace of Mind: Relax knowing key big-ticket items—the roof, AC, and hot water tank—were all updated in 2025 and 2026.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. ViennaSquare is a beautifully maintained, amenity-rich community designed for easy living. Monthly fees includes lawn mowing, and a Spectrum Internet/TV package. Residents enjoy access to a communitypool, fitness center, billiards, movie theater, tennis and pickleball courts, and an active social calendar. Step inside, fall in love. Make it yours!

2332 Salzburg Loop, Winter Haven
2037 San Marcos Drive Se Unit 325, Winter Haven
$180,000
2 Beds ⋅ 2 Baths ⋅ Park Lake 02 SubDv. ⋅ 33880 Zip Code
Enjoy city convenience Living in this 2-bedroom, 2-bath in Winter Garden Chain of Lakes Condo. Relax on private dock, fish or swim in the community pool. This home blends style with comport. Low maintenance and ready for your personal touch. Easy access from top shopping , dining, and entertainment-- perfect as a week-end getaway, or year round home. Come check and see for the opportunity to own or investment possibilities. Must be sold. Seller may hold first mortgage with a good down payment.

2037 San Marcos Drive Se Unit 325, Winter Haven
5780 Lakeside Landings Boulevard, Winter Haven
$290,000
4 Beds ⋅ 3 Baths ⋅ Lakeside Landings Ph 01 SubDv. ⋅ 33881 Zip Code
Enjoy peaceful pond views, spacious living, and desirable community amenities in this 4-bedroom, 2.5-bathroom, two-story home in Winter Haven! Built in 2016, this 2,526-square-foot home offers plenty of room to spread out and enjoy comfortable everyday living. Step outside and take in the pond view from the backyard, providing a relaxing backdrop to unwind at the end of the day. Major updates include a roof replacement in late 2023 and exterior paint completed shortly afterward. The A/C has also been recently serviced for added peace of mind. Located in an established community of Lakeside Landings featuring sidewalks, a neighborhood pool, and a playground, there are plenty of opportunities to enjoy the outdoors. Conveniently situated near Lake Fannie, with easy access to I-4, shopping, dining, and other everyday conveniences, this home puts you within reach of all that Winter Haven and Central Florida have to offer. Don't miss the opportunity to make this spacious home your own!

5780 Lakeside Landings Boulevard, Winter Haven
3937 Giorgio Drive, Winter Haven
$334,000
4 Beds ⋅ 2 Baths ⋅ Villamar SubDv. ⋅ 33884 Zip Code
Brand new, energy-efficient home available by Oct 2026! Prepare dinner while catching up on the days events from this home's open kitchen which overlooks a spacious great room and dining area. Retreat to your primary suite that is conveniently situated in the back of the home for plenty of privacy. 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.

3937 Giorgio Drive, Winter Haven
3115 Captain Jax Way, Winter Haven
$204,790
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.

3115 Captain Jax Way, Winter Haven
1606 Eagle Pond Drive, Winter Haven
$155,000
2 Beds ⋅ 2 Baths ⋅ Eagle Pond Condo SubDv. ⋅ 33884 Zip Code
Step into an inviting opportunity and a genuine deal at this price in the desirable Cypresswood Golf & Country Club. Whether you’re seeking a comfortable full-time residence, a relaxing winter retreat, or a place to embrace an active Florida lifestyle, this second-floor 2-bedroom/2-bathroom condo delivers warmth, convenience, and a true sense of community.Enjoy the privacy of an upper-level location with a practical, easy-flow layout designed for comfortable living, plus a convenient storage room for extra belongings. Maintenance-free ownership means the HOA handles exterior and ground maintenance, community pool access, 24-hour security, common-area upkeep, trash service, exterior pest control, and private road maintenance—so you can simply enjoy your home.The convenient location, a short drive to Legoland Florida Resorts, and offers easy access to Hwy 27, making shopping, dining, medical facilities, and everyday errands quick and simple while still keeping you nestled in a peaceful community setting. Residents are welcomed into a lifestyle filled with amenities: a championship 18-hole golf course, on-site restaurant & clubhouse for dining & events, sparkling community swimming pool, tennis courts & pickleball courts, and fitness center. Perfectly positioned for those who value both relaxed living and an active community atmosphere, this condo offers exceptional value and an immediate sense of belonging in one of Winter Haven’s most appealing settings. Schedule your private showing today and experience the lifestyle for yourself. All buyers must provided a pre-approval letter or proof of funds. Buyers are responsible for verifying the accuracy of all information.

1606 Eagle Pond Drive, Winter Haven
824 Andrew Street, Winter Haven
$333,140
4 Beds ⋅ 3 Baths ⋅ Willowbrook North SubDv. ⋅ 33881 Zip Code
Under Construction. Beautiful 2 Level, 2 Car Garage Home with Open Concept Living and 4 Bedrooms! The inviting front porch opens to a gracious foyer with 2 adjacent secondary bedrooms and a full bathroom. The spacious family room is open to the dining area and adjacent kitchen. The primary suite boasts an en suite bathroom with dual sink vanity, shower, private water closet, and large walk-in closet. The 2nd level offers a spacious loft and 2 secondary bedrooms each with walk-in closets and a full bathroom.

824 Andrew Street, Winter Haven
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