Winter Haven Homes with Pool Amenities

Winter Haven Homes with Pool Amenities

Welcome to Winter Haven, Florida—a charming city nestled in the heart of Polk County, known for its stunning lakes, vibrant community, and a plethora of recreational activities. With its picturesque landscapes and warm, sunny climate, Winter Haven is the perfect place to call home. The city is renowned for its beautiful chain of lakes, which offers residents endless opportunities for boating, fishing, and enjoying the great outdoors.

When it comes to real estate, Winter Haven boasts an impressive selection of homes, many of which come with delightful pool amenities. Imagine coming home after a long day to your own private oasis, where you can relax by the poolside, host summer barbecues, or enjoy a refreshing swim under the Florida sun. Homes with pool amenities in Winter Haven are designed for both comfort and entertainment, providing the perfect backdrop for creating lasting memories with family and friends.

In addition to its beautiful homes, Winter Haven is home to a thriving community with a rich cultural heritage. Residents enjoy access to excellent schools, parks, and a variety of shopping and dining options. With its friendly atmosphere and strong sense of community, Winter Haven is an ideal place for families, retirees, and everyone in between.

Whether you’re looking for a cozy single-family home or a spacious property with a stunning pool, Winter Haven has something to offer everyone. Discover the charm of this lovely city and make it your home today!

Newest Winter Haven Homes with Pool Amenities

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
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
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
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
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
5780 Lakeside Landings Boulevard, Winter Haven
$290,000
4 Beds ⋅ 3 Baths ⋅ Lakeside Landings Ph 01 SubDv. ⋅ 33881 Zip Code
Enjoy peaceful pond views and spacious living 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. 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 (part of the Chain of Lakes) off Lucern Park Rd, with easy access to Hwy 27, 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
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
353 Meredith Boulevard, Winter Haven
$344,990
4 Beds ⋅ 3 Baths ⋅ Willowbrook North SubDv. ⋅ 33881 Zip Code
Under Construction. Beautiful 2 Level, 2 Car Garage Home with Open Concept Living, Loft and 4 Bedrooms! The inviting front porch opens to a gracious foyer with adjacent powder room. The well-appointed, island kitchen is open to the adjoining cafe and spacious family room. The primary suite boasts an ensuite bathroom with dual sink vanity, shower, private water closet, and large walk-in closet. The 2nd level offers a spacious loft, 3 secondary bedrooms, each with walk-in closets, a full bathroom and a convenient laundry room.

353 Meredith Boulevard, Winter Haven
273 Mariposa Street, Winter Haven
$285,000
3 Beds ⋅ 2 Baths ⋅ Florida Highland Co SubDv. ⋅ 33884 Zip Code
Welcome to 273 Mariposa St. in the desirable Orchid Springs Patio Homes community in Winter Haven! This beautifully maintained 3-bedroom, 2-bathroom home has undergone MAJOR UPGRADES THROUGHOUT in 2022/2023, offering a wonderful combination of modern improvements, spacious living areas, and Florida charm! The versatile floor plan features a formal living room, dining room, and family room, with luxury vinyl plank flooring throughout much of the home and tile flooring in the family room. The inviting living room features vaulted ceilings accented by beautiful wood beams, adding warmth and character. The FULLY REMODELED KITCHEN is a standout feature, offering gorgeous granite countertops, updated cabinetry, a center island, stylish backsplash, and stainless steel appliances, including built-in ovens, cooktop, microwave, and dishwasher. The dining room is enhanced by classic wainscoting and sliding glass doors that fill the space with natural light and provide easy access to the family room and outdoor living areas. The bathrooms have received attractive updates! The guest bathroom features an updated vanity, toilet, tile, backsplash, and fresh paint. The spacious primary suite offers a private ensuite bathroom and generous closet space. The list of MAJOR IMPROVEMENTS continues with a COMPLETE HOME REPLUMBING, COMPLETE ELECTRICAL REWIRING WITH UPDATED OUTLETS THROUGHOUT, WINDOWS REPLACED with double-pane windows, updated baseboards, interior repainting, updated blinds, and a NEW WATER HEATER installed in September 2024. The home also features a well-maintained Trane A/C system, an attractive METAL ROOF and an attached 2-car garage with built-in storage cabinetry and a replaced garage door opener. Step outside and enjoy Florida living from the SCREEN-ENCLOSED PATIO or the additional open patio featuring a firepit, perfect for relaxing or entertaining! Situated on a desirable .14-acre CORNER LOT, the property showcases beautiful, mature oak and palm trees, along with thoughtfully maintained landscaping. Orchid Springs Patio Homes offers residents access to a COMMUNITY POOL and CLUBHOUSE, providing a wonderful opportunity to enjoy the Florida lifestyle. LOCATION IS ANOTHER GREAT FEATURE! Conveniently situated near restaurants, medical facilities, churches, and shopping, with a NEW PUBLIX just approximately 5 minutes away! The home also offers easy access to HIGHWAY 27 and is just a short drive from LEGOLAND FLORIDA RESORT, making it easy to enjoy everything Central Florida has to offer. With its extensive upgrades, generous living spaces, inviting outdoor areas, and convenient location, this home is a wonderful opportunity to enjoy Florida living. Schedule your private showing today!

273 Mariposa Street, Winter Haven
4446 Glenns Landing, Winter Haven
$279,900
3 Beds ⋅ 2 Baths ⋅ Cypress Landing Ph 03 SubDv. ⋅ 33884 Zip Code
LOCATION! LOCATION! LOCATION! SPRING-FED LAKE DEXTER WITH REMARKABLY CLEAR WATER! Welcome to CYPRESS LANDING, one of Winter Haven’s hidden gems, offering an incredible Florida lake lifestyle! Residents enjoy private community access to beautiful LAKE DEXTER, featuring a PRIVATE BOAT RAMP, BOAT STORAGE OPTIONS, COMMUNITY BOAT DOCK WITH BOAT SLIPS, WATERFRONT SWIMMING POOL, CLUBHOUSE, TENNIS COURTS, AND SCENIC LAKESIDE WALKING PATHS! Boat storage and boat slips are community amenities; availability, fees, and usage requirements are subject to HOA confirmation. Golf carts are also permitted, subject to community guidelines! Located at 4446 GLENNS LANDING, this inviting 3-BEDROOM, 2-BATHROOM HOME features a BRAND-NEW CENTRAL A/C SYSTEM! Inside, you’ll find CERAMIC TILE FLOORING THROUGHOUT, spacious living and dining areas, and a beautiful kitchen featuring GRANITE COUNTERTOPS AND STAINLESS STEEL APPLIANCES! Expansive rear sliding glass doors bring the outdoors in, seamlessly connecting the interior living space to the covered, screened porch and creating an inviting atmosphere for entertaining or simply enjoying Florida living. The primary suite offers a WALK-IN CLOSET AND PRIVATE BATHROOM WITH A WALK-IN SHOWER, while a skylight brings additional natural light into the home. An interior laundry room and attached garage provide everyday convenience. ENJOY FLORIDA LIVING WITH TWO COVERED, SCREENED PORCHES, both featuring ceramic tile flooring! An UPGRADED PAVER DRIVEWAY, lush St. Augustine lawn, mature shade trees, and attractive landscaping add to the home’s curb appeal. JUST MINUTES FROM LEGOLAND FLORIDA RESORT, shopping, dining, entertainment, and Winter Haven’s renowned CHAIN OF LAKES! Enjoy boating, fishing, kayaking, and waterfront recreation right within your community, with additional public boat ramps nearby. SPRING-FED LAKE DEXTER ACCESS, BRAND-NEW CENTRAL A/C, GRANITE COUNTERTOPS, STAINLESS STEEL APPLIANCES, TWO SCREENED PORCHES, AND EXCEPTIONAL COMMUNITY AMENITIES! Experience the benefits of lake community living without the waterfront price tag. SCHEDULE YOUR PRIVATE SHOWING TODAY!

4446 Glenns Landing, Winter Haven
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