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 that perfectly blends small-town warmth with vibrant community spirit. Known for its stunning lakes and lush landscapes, Winter Haven is often referred to as the "Chain of Lakes" due to its impressive network of interconnected waterways. This picturesque locale offers residents a plethora of recreational activities, from boating and fishing to scenic parks and nature trails. With a rich history and a thriving cultural scene, Winter Haven is not just a place to live, but a place to truly call home.

One of the most coveted features of homes in Winter Haven is the pool amenity. Imagine stepping out into your backyard oasis, where a sparkling pool awaits you, offering a refreshing escape from the Florida sun. Whether you’re hosting summer barbecues, enjoying quiet evenings under the stars, or simply lounging with a good book, a home with a pool transforms your outdoor space into a personal retreat.

In Winter Haven, you’ll find a variety of properties that cater to your lifestyle, from cozy single-family homes to luxurious estates, all equipped with inviting pool areas. These homes not only provide a perfect spot for relaxation but also enhance your entertaining capabilities, allowing you to create unforgettable memories with family and friends.

With its friendly atmosphere, excellent schools, and convenient access to major highways, Winter Haven is an ideal location for families, retirees, and anyone looking to enjoy the best of Florida living. Discover your dream home with a pool in this delightful city, and embrace the lifestyle you’ve always wanted!

Newest Winter Haven Homes with Pool Amenities

4 Beds ⋅ 3 Baths ⋅ Willowbrook North SubDv. ⋅ 33881 Zip Code

Under Construction. CASTAWAY MULTI-GEN: Beautiful 1 Level, 2 Car Garage Home with Open Concept Living and 3 Bedrooms! Featuring a Private Retreat: these thoughtfully designed homes provide flexibility without added monthly costs. Designed for flexibility, the Castaway Retreat offers the ideal solution without added monthly costs. This thoughtfully designed multi-gen layout includes a private retreat with its own kitchenette, living area, bedroom, and full bath, plus both interior access to the main home and a private exterior entrance. An optional washer/dryer hookup adds even more convenience.

819 Andrew Street, Winter Haven

5 Beds ⋅ 3 Baths ⋅ Villamar Phase 7 SubDv. ⋅ 33884 Zip Code

The Robie is a two-story floorplan featured in Villamar in Winter Haven, Florida. With 2 exteriors to choose from, the Robie is sure to turn heads. Inside this inviting 5-bedroom, 3-bathroom home, you’ll find 2,447 square feet of comfortable living. This impressive all concrete block construction, two-story plan features a versatile floorplan to fit your needs. A spacious open-concept first floor which includes a well-appointed kitchen with sleek stainless-steel appliances overlooking the living and dining area. Just off the living room you will find the singular downstairs bedroom and full bathroom. As you move upstairs you are greeted with a spacious living and foyer space to utilize for work or play. The primary bedroom one is located just off the loft space and features a spacious walk-in closet as well as ensuite bathroom with double vanity and all the space you need to get ready in the morning. Three additional bedrooms share a second upstairs bathroom and linen closet for extra storage. Your laundry room is located on the second floor as well as extra storage closets. Like all homes in Villamar, the Robie includes 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.*

5568 Taverna Loop, Winter Haven

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

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

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

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

2 Beds ⋅ 2 Baths ⋅ Eagle Pond Condo SubDv. ⋅ 33884 Zip Code

Additional photos coming soon! Welcome to maintenance-free living nestled in the thriving community of Cypresswood Golf and Country Club that offers an unparalleled lifestyle and peace of mind with a 24-hour guard at the gated entrance, perfect for year-round living or a worry-free seasonal getaway. This second-floor condo boasts a world of comfort and convenience with 10' high ceilings, tons of storage in generously-sized walk-in closets that both bedrooms offer as well as additional linen storage in the hallway and primary bedroom that will keep your space organized and clutter-free effortlessly. Dive into relaxation and fun at the community pool or host gatherings, socialize with neighbors, or simply unwind in the inviting communal spaces of the clubhouse. The on-site restaurant offers convenient and flavorful dining options, perfect after a tennis or pickleball match on the community's courts or day of golf on Cypresswood's 18-hole championship course. The low monthly HOA fee includes all exterior maintenance, landscaping, pest control, trash collection, and the pool and tennis amenities. Residents also enjoy a discount on daily golf and annual memberships! Minutes from Highway 27 and the I-4 corridor, Winter Haven's very own Legoland Florida Resort, the Polk Parkway, and in the center of a thriving community with many convenient grocery, restaurant, shopping, and commuting options. Schedule your private showing today, and make this lovely condominium yours.

1105 Eagle Pond Drive Unit 1105, Winter Haven

4 Beds ⋅ 3 Baths ⋅ Willowbrook North SubDv. ⋅ 33881 Zip Code

Virtually Staged. Under Construction. Under Construction Sample Images: Ready by August 2026. No rear neighbors! 4 Bedrooms and 2 Baths!! The Poinciana is a spacious 2,110 Sq. Ft. floor plan, open concept, with a spacious covered lanai perfect for relaxation and/or entertaining. Sizable great room and two big his and hers walking closets in the master suite. Nice upgrades included like 42" cabinets, stone counters in the kitchen and all bathrooms, tile in wet and common areas, 9'4" ceiling height, and a lot more. One of our most popular floor plan that will fit any family needs.

1052 Luke Avenue, Winter Haven

3 Beds ⋅ 2 Baths ⋅ Willowbrook North SubDv. ⋅ 33881 Zip Code

Virtually Staged. Under Construction. Under construction. Sample Images Ready by August 2026 No rear neighbors! The Auburndale is just the perfect home that feels bigger than 1,407 Sq. Ft. Is an open concept floor plan. Nice-sized kitchen and a spacious master bedroom. Nice upgrades include stone counters in the kitchen and in all bathroom counters, tile in wet and common areas, 9'4" ceiling height, and a lot more.

1040 Luke Avenue, Winter Haven

4 Beds ⋅ 2 Baths ⋅ Willowbrook North SubDv. ⋅ 33881 Zip Code

Virtually Staged. Under Construction. Under construction. Sample Image Ready by August 2026 No rear neighbors! The Bradley looks and feels bigger than 1,625 Sq. Ft. Is an open concept floor plan: spacious master bathroom, dual vanity, and a nice-sized closet. Nice upgrades include stone counters in the kitchen and in all bathroom counters, tile in wet and common areas, 9'4" ceiling height and a lot more.

296 Meredith Boulevard, Winter Haven

2 Beds ⋅ 2 Baths ⋅ Orange Manor West Coop Inc SubDv. ⋅ 33884 Zip Code

Become a share holder in this highly sought after 55+ gated community. If you are looking for the perfect retirement home, this one is for you! Located in Orange Manor West, it is one of the most popular 55+ communities in Winter Haven and surrounding area with many amenities. Pool, shuffle board, putt putt, horse shoes, crochet, bingo, lake access and much more. Legoland is around one mile away which is great for visiting family. This is a 1368 Square ft. 2 bedroom 2 bath 1984 with an attached enclosed Florida room and an enclosed carport with ac. The king size master bedroom has a walk-in closet and a private bathroom with a tub shower. It has an inside utility room with washer & dryer. The monthly maintenance fee is $279.00 a month which includes cable, internet, trash pickup, and amenities. This house is fully furnished and ready to move in. This is also a pet free community. While it is a great winter home get away, it can also be a year round retirement home. Come see it today. This one won't last long. All measurements are approximate and should be verified by the buyer.

113 Lake Hazel Drive, Winter Haven

4 Beds ⋅ 3 Baths ⋅ Peace Creek Reserve 40'S SubDv. ⋅ 33884 Zip Code

Welcome to your dream home in the heart of Winter Haven's sought-after Peace Creek Reserve community! This stunning two-story Atlanta Plan offers 4 bedrooms, 2.5 bathrooms, and 1,933 square feet of thoughtfully designed living space that perfectly balances comfort with style with custom built-in blinds, custom closets in bedrooms & designer touches such as accent wall in living room with floating shelf that will be staying with the home! Step inside to discover an open floor plan that flows seamlessly from the great room to the dining area and into a chef's dream kitchen. The heart of the home features a large island complemented by quartz countertops, stainless steel appliances, and a generous pantry. The casual dining area opens to a lanai through sliding glass doors, creating an effortless indoor-outdoor living experience. Yard is fenced in with built in gazebo and kids playground that are staying with the home! Upstairs, the primary bedroom retreat awaits with a luxurious en-suite bathroom featuring a spacious walk-in shower, dual vanity, and a walk-in closet. Three additional bedrooms, a full bathroom, and a versatile loft provide plenty of space for family, guests, or that home office you've been dreaming about. The convenient second-floor laundry room means no more hauling baskets up and down stairs. Peace Creek Reserve offers the perfect blend of small-town charm and modern convenience, nestled near Winter Haven's famous chain of lakes connected by scenic canals. Publix within 5 minutes, 10 minutes to Legoland Florida, 10 minutes to Cypress Gardens plus easy access to US 27 where you will find tons of shopping, dining and theaters! Locaated an hour from Orlando and an hour from Tampa Bay for easy commute!

1325 Diego Terrace, Winter Haven

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