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

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
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
2212 Starboard Unit 2212, Winter Haven
$229,900
2 Beds ⋅ 2 Baths ⋅ Hartridge Landing SubDv. ⋅ 33881 Zip Code
Enjoy Florida Living in this updated 2BR/2BA home located in the lakefront 55+ community on Lake Hartridge. Only 42 units in Hartridge Harbors condo situated on the beautiful Winter Haven Chain-of-Lakes. Well maintained complex with affordable HOA fees. This home features a 2 car garage, inside laundry, new appliances, Large master suite, and large guest room. Screened and private patio at the rear of the house affords space for outdoor kitchen, spa, or garden area. Location is ideal-close to shopping, restaurants, medical, etc. Community amenities include a clubhouse and pool while offering low maintenance living. Call today for your private showing.

2212 Starboard Unit 2212, Winter Haven
3969 Cypress Landing W, Winter Haven
$250,000
2 Beds ⋅ 2 Baths ⋅ Cypress Landing Ph 02 SubDv. ⋅ 33884 Zip Code
**More PhotosComing** Comfortable, Simple Living in Cypress Landing on Lake Dexter. This 2 Bedroom, 2 Bath Home Has a Vaulted Ceiling Over the Living and Dining Area, and It Makes the Whole Space Feel Open the Minute You Walk In. The Kitchen Has Light-Bright Cabinets, Tile Floors, a Stainless Refrigerator and Dishwasher, a Built In Oven, Cooktop and Microwave, with Sliders Out to the Screened Lanai. The Primary Bedroom Has a Walk In Closet and a Walk In Shower in the Bath. Need More Room? The Enclosed Lanai Gives You Extra Space for a Den, Hobby Room or Home Office. Crown Molding and Ceiling Fans Throughout, a Two Car Attached Garage with Opener and Storage Cabinets, and a Fenced Backyard with Low Maintenance Rock Landscaping. Home Electrical is Generator Ready. The Home Includes Hurricane Shutters - Easy Up And Down Installation. Cypress Landing Offers a Clubhouse, Community Pool, Tennis and Pickleball Courts, Boat Storage, a Private Boat Ramp and a Dock on the Lake. Minutes from Legoland, Shopping and Dining. Schedule Your Showing Today! All Sizes Approximate. Buyer to Verify.

3969 Cypress Landing W, Winter Haven
3952 Giorgio Drive, Winter Haven
$285,000
3 Beds ⋅ 2 Baths ⋅ Villamar SubDv. ⋅ 33884 Zip Code
Under Construction. Brand new, energy-efficient home available by Nov 2026! Configure the flex room in the front of the home to an at home office space or hobby space for the kids. Past the foyer, the open kitchen flows to the dining space, great room and outside patio. Private primary suite offers a spacious area to relax. 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.

3952 Giorgio Drive, 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
3437 Grenville Drive, Winter Haven
$223,000
2 Beds ⋅ 2 Baths ⋅ Traditions Ph 01 SubDv. ⋅ 33884 Zip Code
Discover this 2-bedroom, 2-bath home filled with potential and ready for its next owner. Located in Traditions at Lake Ruby, a maintenance-free, gated 55+ community, this thoughtfully designed home combines comfort, functionality, and style for relaxed Florida living. The kitchen features maple wood cabinetry, an updated microwave, reverse osmosis at the kitchen sink, and a convenient closet pantry. The dining area is highlighted by vaulted ceilings and a decorative arched pass-through to the kitchen, adding character and charm. The open-concept floor plan offers a spacious living room with a decorative planter shelf and triple sliding glass doors leading to the Florida room, where tranquil garden views create a peaceful setting. The primary bedroom suite offers serene backyard views and a walk-in closet. The en-suite primary bathroom is designed for comfort, featuring a comfort-height vanity, tile flooring, and a walk-in shower with a glass door. Enjoy outdoor living even during inclement weather from the Florida room, while the low-maintenance courtyard, enhanced with pavers and Florida-friendly landscaping, provides a private and inviting outdoor retreat. The fenced backyard with mature plantings offers additional outdoor space. Additional features include a laundry pantry with washer and dryer, architectural shingle roof (2020), HVAC system (2017), exterior lighting, water softener system, gutters, a glass entry storm door, and a two-car garage. A paved driveway and walkway further enhance the home's curb appeal. Traditions at Lake Ruby offers an impressive array of amenities, including a lakefront clubhouse, dock and boat ramp, heated swimming pool and spa, ballroom, billiards, meeting rooms, library, computer room, craft room, dog park, tennis and basketball courts, bocce, shuffleboard, fitness center, and aerobics studio. Residents can also enjoy a variety of planned community activities. Monthly HOA fees cover front-yard lawn service, cable tv, internet, exterior house painting, and community clubhouse amenities helping provide a convenient, low-maintenance lifestyle. Ideally located near shopping, restaurants, medical facilities, Legoland, and major routes, this home offers a wonderful combination of comfort, convenience, and vibrant community living.

3437 Grenville Drive, Winter Haven
251 Greenfield Road, Winter Haven
$224,900
2 Beds ⋅ 2 Baths ⋅ Cypresswood SubDv. ⋅ 33884 Zip Code
VACANT AND PRICED TO SELL! NEW ROOF 2025! 2 BED 2 BATH CONCRETE BLOCK STUCCO (CBS) HOME IN GUARD GATED CYPRESSWOOD GOLF AND COUNTRY CLUB, WINTER HAVEN FL 33884. Vacant single story home on a 0.44 acre lot with an attached garage, central air, and no CDD. Roof replaced 2025 and water heater 2017. The home needs some work and is priced for its condition. Seller is open to making repairs needed for FHA or conventional loan approval. Cypresswood is a golf cart friendly golf course community with a 24 hour guard gate, 18 hole championship golf course, clubhouse, community pool, and tennis. Located in Polk County near Legoland Florida, Cypress Gardens, the Chain of Lakes, shopping, dining, US 27, and the I-4 corridor between Orlando and Tampa. FHA, VA, conventional, and cash welcome. Sold as is.

251 Greenfield Road, Winter Haven
6240 Pinehurst Loop, Winter Haven
$399,000
3 Beds ⋅ 2 Baths ⋅ Lake Ashton West Phase Ii North SubDv. ⋅ 33884 Zip Code
Virtually Staged. Welcome to your dream retirement home located at 6240 Pinehurst Loop Winter Haven, Fl. 33884, designed with 3 Bedrooms and 2 full bathrooms. This delightful Sebastian home in the highly sought after Lake Ashton, a 55 plus community in Central Florida, was BUILT in 2022. It features a spacious living area with Trey Ceiling and abundant Natural light thru the Glass Front Entry Door with Privacy Tint, Triple Sliders in the LR and Double Glass Window in the Dinette area; Plantation Shutters in the Bedrooms, an Upgraded Kitchen with Stainless Steel Appliances, Under Cabinet Lighting, Breakfast Bar, Walk in Pantry, Cabinet Pantry with Pull Out Drawers and Granite countertop. The inviting living and dining areas blend seamlessly together with carpet flooring, while the open-concept layout is beautifully enhanced by tile flooring in the kitchen, laundry, guest bathroom/hall, entry and Primary Suite bath. Two spacious guest bedrooms and a full bath are located near the front entry; a pocket door provides privacy and a Linen Closet provides storage. The guest bath has a comfort height vanity with Granite counter top, and glass block window is above the tiled shower/tub combo. The Primary Suite is a private retreat on the back of the home, complete with a generously sized bathroom with separate comfort height vanities, a tiled corner shower with glass block accent above and a separate walk in closet. Step outside and enjoy the screened and covered lanai that overlooks the seasonal pond, perfect for entertaining. Plumbing was added to the privacy wall at the time of build, should you desire to have a summer kitchen. The laundry room with wash sink is spacious and is accessible from the garage and kitchen. The exterior of the home has been well maintained with landscaped flower beds and the double car garage with separate golf cart entry is a bonus. A water filtration system is located in the garage. Don't miss the opportunity to explore this wonderful property! Lake Ashton is a Florida Retirement Community that offers a Florida Retirement Lifestyle with resort style amenities and activities for 55+ in Florida. The main clubhouse offers a movie theater, bowling lanes, grand ballroom, card, craft and billiards, outdoor temperature controlled swimming pool, Bocce Courts, tennis courts, 1/2 court basketball, shuffleboard courts and MORE. The Health and Fitness Center has a large indoor temperature controlled pool, fitness center, indoor 1/2 court basketball, indoor racquetball, large multi-purpose room, card, craft, billiards, pickle ball courts and tennis courts. 2 -18 hole golf courses are located in Lake Ashton (memberships are optional). Tour this well maintained home today! You'll be glad you did!

6240 Pinehurst Loop, Winter Haven
4235 Cedarwood Street, Winter Haven
$109,000
2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv. ⋅ 33880 Zip Code
Walk right into this beautifully maintained home located in Oakwood Estates, a 55+ community. The metal roof is only 6 years old. The home has newer windows and a new vapor barrier. The lanai has all new windows. The home also has a water filtration system. The furnishings you see will stay with the home. The living and dining room give a very open and inviting feel. The kitchen bar offers additional eating space for when the whole family comes to visit. The ample kitchen cabinetry has been updated. The only carpet remaining in the home is in the guest bedroom, but it is in very good condition. Sit on the front porch or side lanai for your morning coffee. Enjoy the peaceful community or join in to the many activities available year round. The community offers two pools, two clubhouses, shuffleboard, tennis courts, bocci ball, miniature golf, and much, much more. Make your appointment today.

4235 Cedarwood Street, Winter Haven
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