Winter Haven Homes with Pool Community Features

Winter Haven Homes with Pool Community Features

Winter Haven, located in Polk County, Florida, is a charming city known for its beautiful lakes and warm climate. Situated in the heart of the state, Winter Haven offers residents a perfect blend of natural beauty and urban amenities.

One of the key features of Winter Haven is its Homes with Pool communities. If you're someone who enjoys the luxury of having a pool right at your doorstep, Winter Haven is the place for you. These communities offer residents the opportunity to relax and unwind in their own private oasis. Whether you prefer to take a refreshing dip in the pool after a long day or host poolside gatherings with friends and family, these communities provide the perfect setting.

Living in a Homes with Pool community in Winter Haven also means enjoying a range of additional amenities. Many of these communities offer well-maintained common areas, such as clubhouse facilities, fitness centers, and tennis courts. These amenities provide residents with opportunities for socializing and staying active without ever having to leave the neighborhood.

In addition to the poolside lifestyle, Winter Haven boasts a vibrant downtown area, with a variety of shops, restaurants, and entertainment options. The city is also home to the famous Legoland Florida Resort, which attracts visitors from all over the world.

With its picturesque lakes, warm weather, and Homes with Pool communities, Winter Haven is a city that offers residents a truly exceptional quality of life. Whether you're looking for a vacation home or a permanent residence, Winter Haven has something to offer everyone.

Newest Winter Haven Homes with Pool Community Features

$194,900
3 Beds ⋅ 2 Baths ⋅ Orchid Springs Village SubDv. ⋅ 33884 Zip Code
A MUST SEE! Beautifully renovated first-floor unit located in the well-kept 55+ Granada Building in Orchid Springs! This spacious condo spans over 1,500 square feet of living space, featuring an open floor plan with 3 bedrooms and 2 bathrooms. Updates include a new modernized kitchen and bathrooms, stunning granite countertops, new stainless steel appliances, gorgeous luxury vinyl flooring throughout, and a freshly painted tan interior radiating classic warmth and timeless style. The laundry closet offers maximum convenience, complete with a washer and dryer. The monthly HOA fee includes the use of the clubhouse and community pool, gas, water, trash, cable, internet, pest control, and exterior & grounds maintenance. Designed for ultimate relaxation, the Florida room boasts lovely views of the lagoon. Don't miss your chance to transition into effortless comfort with low-maintenance living in a peaceful setting. Call us today!

100 El Camino Dr Unit 104, Winter Haven
$150,000
2 Beds ⋅ 2 Baths ⋅ Village Park SubDv. ⋅ 33880 Zip Code
Welcome to easy, affordable Florida living! This well-maintained 2-bedroom, 2-bath manufactured home is nestled in Village Park, a desirable 55+ community in Winter Haven and offers the perfect blend of comfort, convenience, and an active lifestyle. With a low HOA and NO LOT FEES, you'll enjoy affordable, low-maintenance living. Inside, you'll find a bright and inviting floor plan featuring a spacious living room, a designated dining area, and a functional kitchen complete with a breakfast bar—perfect for casual meals or entertaining guests. The primary suite serves as a private retreat with a walk-in closet and an en suite bathroom. One of the home's standout features is the generously sized screened-in porch overlooking the peaceful community pond, providing the perfect place to enjoy your morning coffee or unwind while taking in the tranquil water views. Situated at the end of a quiet street with no through traffic, this home offers added privacy and a serene setting. A covered carport provides convenient parking. Residents of this welcoming 55+ community have access to fantastic amenities, including a sparkling community pool, clubhouse, shuffleboard courts, and a full calendar of social activities designed to keep you active and connected with your neighbors. Conveniently located just minutes from shopping, restaurants, medical facilities, parks, and everyday conveniences, this move-in-ready home is vacant and easy to show. Whether you're looking for a full-time residence or the perfect Florida getaway, this charming home offers the relaxed lifestyle you've been searching for.

489 Village Circle Sw, Winter Haven
$399,990
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
$325,990
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
$749,000
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
$396,140
4 Beds ⋅ 3 Baths ⋅ Villamar SubDv. ⋅ 33884 Zip Code
Under Construction. Brand new, energy-efficient home available by Aug 2026! An open floorplan that makes entertaining easy in the open kitchen, dining, and great room that flow to the patio. The primary suite is tucked in the rear of the home offering plenty of privacy and features a spacious walk-in closet and 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.

3757 Giorgio Drive, Winter Haven
$296,630
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
$125,000
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
$70,000
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
$165,000
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
$319,990
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
$274,990
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
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