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, renowned for its stunning chain of lakes and vibrant community spirit. With its warm climate, rich history, and abundance of recreational activities, Winter Haven is an idyllic place to call home. Whether you’re drawn to the picturesque landscapes or the friendly neighborhoods, this city offers a perfect blend of relaxation and excitement.

One of the most sought-after features in Winter Haven’s real estate market is homes with pool amenities. Imagine stepping into your own backyard oasis, where you can unwind under the sun, host family gatherings, or enjoy a refreshing swim on a warm Florida day. These homes not only provide a private retreat but also enhance your lifestyle, allowing you to embrace the outdoor living that Florida is famous for.

Many properties in Winter Haven boast beautifully designed pools, complete with landscaped gardens, outdoor kitchens, and spacious patios—ideal for entertaining friends and family. Whether you prefer a cozy, intimate setting or a grand space for entertaining, there is a diverse selection of homes to meet your needs.

Living in Winter Haven means you’ll have access to a wealth of amenities, including parks, shopping, dining, and a variety of water sports. With its friendly atmosphere and community events, Winter Haven is not just a place to live, but a place to thrive. Explore the possibilities and discover your dream home with a pool in this delightful Florida city!

Newest Winter Haven Homes with Pool Amenities

$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
$174,900
2 Beds ⋅ 2 Baths ⋅ Garden Grove Oaks SubDv. ⋅ 33884 Zip Code
Just bring your personal belongings for this fully furnished home. Officially it is 2 bedrooms, 2 bath home however the front room could be converted to a 3 bedroom just add a closet. Wonderful club house, a inground community pool and a pond stocked with fish with a low monthly fee of $65.00/month. 55 plus age requirement of one of the buyers in this community of Garden Grove Oaks. You own your land and you can file homestead making your taxes very low. Kitchen is very user friendly with updated appliances. In fact, the dishwasher and refrigerator are still under warranty. All the carpet was replaced with laminate. This home has a workshop/hobby room in the shed with another storage area and a private back yard screened porch with vinyl windows. Conveniently located to medical facilities, shopping, restaurants and major highways leading to Lake Wales, Haines City, Orlando and Tampa.

6086 Southern Oaks Drive, Winter Haven
$114,995
2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv. ⋅ 33880 Zip Code
Welcome to 4063 Rolling Oaks in Winter Haven, located in Oakwood Estates, a desirable co-op 55+ community. This well-maintained 2 bedroom, 2 bathroom home offers a spacious and versatile floor plan featuring a bonus room and a Florida room, providing plenty of space for relaxing, entertaining, hobbies or a home office. Laminate flooring flows throughout the main living areas and bedrooms, while the Florida room features tile flooring. The dining room includes a built-in buffet with display cabinets and additional storage, creating the perfect space for showcasing your favorite pieces and hosting family and friends. The kitchen offers a convenient closet pantry for added storage, and both bedrooms feature generous walk-in closets. Exterior features include window awnings and an attached carport. A BRAND NEW ROOF was put on (08/2026). Oakwood Estates offers an affordable Florida lifestyle with low HOA fees that include water and trash service. Residents can also enjoy many amenities of this lakefront community including; two clubhouses, two swimming pools, an activity center with a pool table, tennis & pickleball courts, a mini golf course and a lake with fishing dock. Don’t miss this opportunity to own a home in a welcoming community conveniently located near shopping, dining, and all the great amenities and attractions Winter Haven is known for.

4063 Rolling Oaks Drive, Winter Haven
$299,990
4 Beds ⋅ 2 Baths ⋅ Willowbrook North SubDv. ⋅ 33881 Zip Code
Welcome to this beautifully designed home featuring a traditional exterior and inviting covered front porch. Inside you'll find a gracious foyer that leads into an open-concept living space, where the island kitchen flows seamlessly into the café and family room—creating a comfortable setting for everyday living and entertaining. The private garage provides convenient access to the interior hallway, which leads to three secondary bedrooms and a full bathroom with a dual-sink vanity. The spacious primary suite offers a relaxing retreat with a large walk-in closet and an ensuite bathroom featuring a walk-in shower and private water closet. Thoughtfully designed for both comfort and functionality, this home offers a well-balanced layout with inviting shared spaces and private bedroom accommodations.

341 Meredith Boulevard, Winter Haven
$149,000
2 Beds ⋅ 2 Baths ⋅ Wellington Pt 01 Bldgs 01 02 & Wellington Pt 02 B SubDv. ⋅ 33880 Zip Code
This is 55+ living at its best! Fully renovated with high-end finishes, a spotless, move-in-ready interior, and a desirable lakeside setting on the world-famous Winter Haven Chain of Lakes. Welcome to 689 Lake Howard Drive, Unit 213, where thoughtful updates, generous living spaces, and an exceptional waterfront community come together at an attractive price point. Located in The Wellington on the shores of Lake Howard, this impressive 2 bedroom, 2 bath condo feels fresh, modern, and remarkably spacious. The expansive living and dining area features beautiful flooring, crown molding, updated lighting and ceiling fans, and plenty of room for comfortable everyday living and entertaining. Sliding glass doors open to a large enclosed Florida room overlooking the beautifully maintained community grounds, providing even more space to relax and enjoy the Florida lifestyle. The remodeled kitchen is a standout, featuring quartz countertops, abundant white soft-close cabinetry, a farmhouse-style sink, herringbone tile backsplash, under-cabinet lighting, and a complete stainless steel LG appliance package including refrigerator, range, microwave, and dishwasher. Both bathrooms have been beautifully remodeled with quartz-topped vanities and impressive custom tile work. Walk-in showers feature frameless glass enclosures, decorative tile accents, niches, and contemporary finishes. An exceptionally large walk-in closet provides outstanding storage, while an interior laundry closet with included washer and dryer and a large private exterior storage room add everyday convenience. The Wellington offers beautifully landscaped grounds, two pool areas including a heated pool for winter use, clubhouse, shuffleboard, community activities, and a private dock on Lake Howard with access to the Winter Haven Chain of Lakes—perfect for fishing and enjoying life on the water. The condo fee includes basic cable and internet, water, garbage pickup, exterior building maintenance, and grounds maintenance. A private covered parking space is also included. Conveniently located near medical facilities, shopping, restaurants, churches, grocery stores, and charming Downtown Winter Haven. Beautifully remodeled, incredibly spacious, and located in a Chain of Lakes waterfront community—this is 55+ living with the updates already done for you!

689 Lake Howard Drive Nw Unit 213, Winter Haven
$164,800
2 Beds ⋅ 2 Baths ⋅ Lakeside Ranch For Mobile Homes SubDv. ⋅ 33881 Zip Code
Meticulously Maintained, beautiful 2/2, move-in ready home in a quiet lake-front community. Pride of Ownership shows throughout! List of Updates attached and include finished walls, Plumbing, downspouts, Heat Pump with UV Light, Newer Appliance, Washer and Dryer (inside laundry), flooring, kitchen cabinets with soft-close, built-in pantry/storage in the Dining Room to name a few. Thoughtfully maintained, offering peace of mind and comfort from day one! BONUS=2024 Evolution C4PRO golf cart is included! The sales price includes the $11,000 share of ownership in this Co-op Community. The low $145/mo HOA fee includes water, sewer, and lawn mowing. Individual mailbox, community laundry and clothesline available. No pets. No motorcycles. Trucks ok. Located near shopping, entertainment, and health care!

628 Lakeside Ranch Lane, Winter Haven
$303,990
4 Beds ⋅ 2 Baths ⋅ Harmony On Lake Eloise Phase 4 SubDv. ⋅ 33884 Zip Code
Introducing the Harper floorplan at Harmony at Lake Eloise, 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 provide 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 Harmony at Lake Eloise, 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. *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.*

3117 Firebrush Lane, Winter Haven
$139,900
2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv. ⋅ 33880 Zip Code
Walk right into this beautiful home located in Oakwood Estates, a 55+ community. You will find the home nicely furnished which all conveys with the sale of the home. The open living area at the front of the home has a beautiful lake view. The kitchen is open to another living space or dining area. The primary bedroom at the rear of the home is nice sized and will accommodate a king sized bed. The guest bedroom is attached to the guest bathroom offering privacy and convenience to your guests. The Lanai which is also air conditioned (vent behind the couch) offers a wonderful area to sit and enjoy your morning coffee where you can watch the world go by. Oakwood Estates offers many activities and amenities including two pools, two clubhouses, tennis courts, shuffle board, miniature golf and much more. You can stay as busy as you like or just sit back and enjoy the peaceful community. The golf cart is included in the sale of the home. The Sellers have a home warranty in place and with a reasonable offer will pay for three month to continue the plan. Make your appointment today to see this beautiful home.

4234 Rolling Oaks Drive, Winter Haven
$325,000
3 Beds ⋅ 2 Baths ⋅ Villamar Ph 6 SubDv. ⋅ 33884 Zip Code
Stunning VillaMar residence in Winter Haven, built in 2024, showcasing modern construction with a clean, contemporary design throughout. The interior features an inviting layout highlighted by a chef-style kitchen that opens seamlessly to a spacious great room, creating an ideal space for both everyday living and entertaining. This home includes a whole-house water filtration system, a screened front porch for comfortable outdoor relaxation, a fully fenced backyard for privacy, and enhanced landscaping with decorative stone accents and fresh plantings that elevate the exterior appeal. Conveniently located approximately 10 minutes from Legoland Florida and about one hour from Disney World, this property offers both comfort and an exceptional lifestyle location. Thoughtfully designed and move-in ready, it delivers style, quality, and lasting value. Schedule your private tour today! Errors, omissions, changes, withdrawal may occur. *Buyers are advised to independently verify square footage, permits, and property details.

4913 Kaia Avenue, Winter Haven
$309,990
3 Beds ⋅ 2 Baths ⋅ Harmony On Lake Eloise Phase 4 SubDv. ⋅ 33884 Zip Code
Under Construction. The Astor is one of our one-story floorplans featured in Harmony at Lake Eloise in Winter Haven, Florida. With 3 exteriors to choose from, the Astor is sure to turn heads. Inside this 3 bedroom, 2 bathroom home, you’ll find 1,565 square feet of comfortable living. This home offers a two-car garage and covered porch in the rear of the home. As you enter, you're greeted with a spacious living area, coat and linen storage closets and dedicated laundry room. The kitchen located in the center of the home features quartz countertops, an island, stainless steel appliances and a pantry. You’ll never be too far from the action with the living and dining area to the immediate left and right. The primary bedroom has an attached bathroom that features a walk-in closet, double sink vanity and all the space you need to get ready in the morning. Every bedroom features carpeted floors and a closet. Whether these rooms become bedrooms, office spaces, or other bonus rooms, there is sure to be comfort. Like all homes in Harmony at Lake Eloise, the Astor 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.*

1746 Hummingbird Road, Winter Haven
$149,500
2 Beds ⋅ 1 Baths ⋅ Haven The A Condo SubDv. ⋅ 33881 Zip Code
YOU WILL APPRECIATE THE CHARACTER AND HISTORIC CHARM AS YOU WALK UP THE STEPS TO ENTER THE LOBBY OF THE HISTORIC HAVEN. AN ELEVATOR IS AVAILABLE HOWEVER, DON'T HESITATE TO USE THE STAIRS. BE SURE TO TAKE IN ALL THE LOBBY AREA WITH THE FOUNTAIN AND THE SITTING AREA ON THE SECOND FLOOR BEFORE ENTERING THIS 2BR-1BA UNIT WITH A 30X14 BALCONY OVERLOOKING THE CITY LIGHTS OF DOWNTOWN. ONLY A COUPLE BLOCKS WALKING TO DOWNTOWN RESTAURANTS AND SHOPPING, ANTIQUES, LIBRARY, SPECIALTY SHOPS AND GREAT RESTAURANTS FROM PIZZA TO FINE DINING. YOU'LL ENJOY SITTING ON THIS BALCONY WITH YOUR MORNING COFFEE OR SPEND TIME ENTERTAINING ON THIS SPACIOUS BALCONY. ONCE YOU STEP INSIDE THE UNIT YOU OBSERVE THE UNIQUE COLUMN OF THE TIMES GONE BY. THIS UNIT HAS A GALLEY KITCHEN EQUIPPED WITH RANGE, REFRIGERATOR, AND DISHWASHER AND A CONVENIENT PASS THRU FROM THE KITCHEN. THE OPEN GREAT ROOM WITH HIGH CEILINGS , HAS PARQUET FLOORING THROUGHOUT AND DOUBLE GLASS DOORS LEADING TO THE BALCONY. THE HALL CLOSET HOLDS THE STACKABLE WASHER/DRYER FOR CONVENIENCE. 13 X 11 MASTER BEDROOM AND 12 X 11 GUEST BEDROOM WITH STORAGE UNIT FOR CONVENIENCE IF YOU WISH TO USE THIS AS A STUDY OR HOME OFFICE. YOU'LL APPRECIATE THE UPDATED BATH WITH A WALK IN SHOWER WHICH IS CONVENIENTLY LOCATED OFF THE MASTER BR. THE HAVEN OFFERS A COMMUNITY POOL AND ASSIGNED PARKING. WINTER HAVEN IS A DIAMOND IN THE ROUGH AND OFFERS SO MUCH TO OUR COMMUNITY WITH THE CHAIN OF LAKES, RESTAURANTS ON THE WATER, OH YES, CYPRESS GARDENS SKI SHOW ON LAKE SILVER ONLY MINUTES AWAY AND OF COURSE WE ALSO HAVE LEGOLAND ONLY A SHORT DRIVE . WINTER HAVEN IS LOCATED IN CENTRAL FLORIDA WITH EASY ACCESS TO I-4 TAMPA OR ORLANDO/DISNEY. ADDITIONAL PHOTOS TO FOLLOW. --

235 6th Street Nw Unit 205, Winter Haven
$229,900
2 Beds ⋅ 2 Baths ⋅ Winterset 01 A Condo 02 Amd SubDv. ⋅ 33884 Zip Code
Completely renovated, ground-floor condo with expansive lake views on the Winter Haven Chain of Lakes! Welcome to Winterset, where this beautifully reimagined 2-bedroom, 2-bath residence combines a spacious interior, private screened porch, exceptional water views, and the amenities of one of Winter Haven's most desirable gated communities. From top to bottom the home feels fresh, bright, and remarkably spacious. New flooring flows throughout, complemented by updated lighting, contemporary ceiling fans, modern fixtures, and a crisp neutral palette. The open living and dining areas provide plenty of room to relax and entertain, while large windows frame the expansive lawn and sparkling waters of Lake Winterset beyond. The redesigned kitchen has been expanded for greater functionality and features granite countertops, soft-close cabinetry with crown molding, black appliances, a gas range, dishwasher, generous breakfast bar, and abundant cabinet and counter space. Open to the dining and living areas, it creates an easy flow throughout the main living space. The oversized primary suite is one of the home's standout features, offering beautiful lake views and direct access to the private screened porch—a peaceful spot for morning coffee, an afternoon book, or simply enjoying the breeze and ever-changing colors of sunsets over the water. An exceptionally large walk-in closet provides impressive storage, while the completely renovated en-suite bath features a double vanity with undermount sinks and granite countertop, updated fixtures, and a frameless glass walk-in shower surrounded by custom tile. Positioned separately from the primary suite, the spacious second bedroom offers two closets and convenient access to the beautifully renovated guest bath, complete with granite-topped vanity and custom-tiled tub and shower. The thoughtful layout also includes an interior laundry area and additional storage. Beyond the residence, Winterset delivers the Florida lifestyle buyers come here to enjoy. Residents have access to a heated lakefront swimming pool and spa, clubhouse, tennis and pickleball courts, shuffleboard, and a private boat ramp with direct access to the Winter Haven Chain of Lakes—opening the door to boating, fishing, water skiing, sunset cruises, and waterfront dining. Shopping, restaurants, medical facilities, LEGOLAND Florida Resort, and downtown Winter Haven are all just minutes away, while convenient routes toward Tampa and Orlando make the location equally appealing for everyday living and weekend adventures. Beautifully renovated, ground-floor living, an unusually spacious primary suite, private screened porch, resort-style amenities, Chain of Lakes access, and a gorgeous water view right outside your windows—this is the kind of Winter Haven condo that's easy to fall in love with.

503 Sweet Bay Circle, Winter Haven
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