Winter Haven Homes with Clubhouse Amenities

Winter Haven Homes with Clubhouse Amenities

Welcome to Winter Haven, Florida—a charming city nestled in the heart of Polk County, renowned for its stunning lakes and vibrant community spirit. With a rich history and a wealth of recreational opportunities, Winter Haven is the perfect blend of small-town charm and modern living. Known as the "Chain of Lakes" city, it boasts over 50 lakes, making it a paradise for water enthusiasts, whether you enjoy fishing, boating, or simply soaking up the sun.

One of the standout features of Winter Haven is its array of homes that come with clubhouse amenities. Imagine waking up each day to a lifestyle that includes access to beautifully designed clubhouses, where you can socialize with neighbors, host gatherings, or simply unwind. These communities often feature sparkling swimming pools, fitness centers, and recreational facilities, all designed to enhance your living experience.

Living in Winter Haven means more than just having a roof over your head; it’s about embracing a vibrant lifestyle. The local parks, shops, and dining options create a warm and inviting atmosphere, perfect for families and retirees alike. Whether you’re exploring the scenic trails of the nearby parks or enjoying a day at the renowned Legoland Florida Resort, there’s always something exciting to do.

With its welcoming neighborhoods and a strong sense of community, Winter Haven is not just a place to live; it’s a place to thrive. Discover your dream home today and experience the joys of living in a city that truly has it all!

Newest Winter Haven Homes with Clubhouse Amenities

$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
$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
$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
$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
$355,000
3 Beds ⋅ 2 Baths ⋅ Lake Ashton West Ph Ii South SubDv. ⋅ 33884 Zip Code
1124 Sawgrass Drive Winter Haven, Fl. 33884 is located in Lake Ashton, an Exclusive Florida Retirement Community offering tailored activities and amenities to those seeking an Active 55 Plus lifestyle. Built in 2022 with 1,917 sq. ft. living area, this ST. MARKS floor plan home is MOVE IN READY and is located on the 10th Fairway of the West Golf Course in Lake Ashton. When you enter this home you have a direct view of the golf course thru the Triple Sliders that separate the LR from the Lanai. This Split Floor Plan offers: Formal and Casual Dining areas, a Living Room, Laundry Room, Primary Suite, 2 Bedrooms and a Flex Room with Built In Shelves. The living room is at the center of the this home with the Kitchen, Formal Dining, Primary Suite and Dinette areas flowing into the LR area. The Kitchen is spacious and offers a Breakfast Bar, SS Appliances, Recessed Lighting, Pull Out Drawers, Ample 42" Cabinetry and Granite Countertops. The Dinette area is easily accessible to the kitchen and Flex Room and Double Sliders provide direct access to the Covered and Screened Lanai. The Open and Spacious Floor Plan makes entertaining a BREEZE! The comfortable and spacious Primary Suite offers His/Her Walk in Closets, an attractive Primary Bath area with His/Her separate vanities, large soaking tub, walk in shower, separate water closet and linen closet. Glass Block accents the Primary Bath and provides an abundance of natural light into the room. Bedroom 2 and Bedroom 3 are separated by the Guest Bathroom with shower/tub combo and comfort height vanity. Each Bedroom has a built in Closet. The laundry room (washer/dryer included in the sale of the home) is sizable and is the passage from the garage to the kitchen. The garage has a separate golf cart entry and the golf cart is included with the sale of the home. Grab a great book and a cup of coffee and relax on the screened and covered lanai. Lake Ashton is a gated and guarded Florida Active Community with resort style amenities (2 Clubhouses with Movie Theater, Restaurant, Outdoor/Indoor Pools, Fitness Centers and More! Residents enjoy activities like Karaoke, Trivia, Dances, Entertainment Series, Holiday Events and so much more. You can stay busy living the Florida Retirement Dream every single day. For those that love the game of golf, there are (2) 18-Hole Golf Courses, a Pro Shop, Driving Range, Putting Green and the Eagles Nest (Hole 19). Don't wait to tour this home; tour it today!

1124 Sawgrass Drive, 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
$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
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
$115,000
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
$185,000
2 Beds ⋅ 1 Baths ⋅ Parkland Village SubDv. ⋅ 33880 Zip Code
Welcome home to this well-maintained 2-bedroom, 1-bath patio home located in the 55+ community of Parkland Village. This move-in-ready home offers numerous recent updates, including a new roof (December 2025), new windows (2024–2025), new A/C (2022), and a new refrigerator and stove (2026), providing comfort and peace of mind for years to come. Inside, you'll find thoughtful features such as vertical blinds, mirrored closet doors, and storm doors and shutters. The home also includes a private courtyard, perfect for relaxing or entertaining, along with a 1-car carport and a storage closet with a washer and dryer. Residents enjoy access to a recreation building and shuffleboard courts, while the low monthly HOA fee of just $110 includes grounds maintenance, making for easy, low-maintenance living. Conveniently located near shopping, banks, and restaurants, this home offers the perfect combination of comfort, convenience, and affordability. Don't miss this opportunity—schedule your private showing today!

790 Avenue Q Se, Winter Haven
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