Winter Haven Homes with Gated Amenities

Winter Haven Homes with Gated Amenities

Welcome to Winter Haven, Florida, a charming city nestled in the heart of Polk County, renowned for its stunning lakes and vibrant community. Known as the "Chain of Lakes," Winter Haven boasts over 50 lakes, providing residents with endless opportunities for boating, fishing, and enjoying the great outdoors. The city is also home to Legoland Florida, making it a family-friendly destination that attracts visitors from near and far.

As you explore Winter Haven, you'll discover a variety of neighborhoods, but none quite as appealing as those featuring gated amenities. These exclusive communities offer an added layer of security and privacy, allowing residents to enjoy their homes in peace. Gated homes in Winter Haven often come equipped with luxurious features such as pools, clubhouses, fitness centers, and beautifully landscaped parks. The sense of community is palpable, as neighbors gather for events and enjoy the shared amenities.

Living in a gated community in Winter Haven means you can relish the tranquility of suburban life while still being just a stone's throw away from the vibrant downtown area, where you'll find delightful shops, restaurants, and cultural attractions. With a warm climate year-round, Winter Haven is perfect for outdoor enthusiasts and those who appreciate a laid-back lifestyle.

Whether you’re looking for a cozy family home or a luxurious retreat, Winter Haven’s gated communities provide the perfect blend of security, comfort, and convenience. Come and discover your dream home in this picturesque city where the sun shines bright and the community spirit runs deep!

Newest Winter Haven Homes with Gated Amenities

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 ⋅ 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

2 Beds ⋅ 2 Baths ⋅ Cypresswood Tennis Villas SubDv. ⋅ 33884 Zip Code

Virtually Staged. Welcome to effortless Florida living in the highly sought-after gated Cypress Wood Golf & Country Club! Perfectly positioned on the beautifully maintained 10th hole, this 2-bedroom, 2-bath villa offers over 1,100 square feet of comfortable living with no close rear neighbors—just breathtaking views of lush fairways, mature oak trees, and Florida wildlife. Inside, you’ll find a bright, open floor plan complete with a spacious Florida room, the perfect place to enjoy your morning coffee or unwind while taking in the peaceful golf course scenery. Offered fully furnished with quick occupancy available, this home is truly move-in ready. Beyond the entrance, experience the exceptional lifestyle that makes Cypress Wood one of Central Florida’s most desirable golf communities. Enter through a 24-hour guard gate and enjoy a scenic drive along beautifully landscaped, tree-lined streets surrounded by meticulously maintained grounds and natural beauty. Residents have access to outstanding amenities including an 18-hole championship golf course, clubhouse, restaurant, community pool, tennis courts, pickleball courts, and a vibrant social atmosphere. The HOA provides lawn maintenance and exterior upkeep, allowing you to spend more time enjoying everything this resort-style community has to offer. Conveniently located just minutes from LEGOLAND Florida Resort, shopping, dining, and everyday conveniences, with easy access to Highway 27 and I-4, offering an easy commute to both Orlando and Tampa. Whether you’re searching for a full-time residence, winter retreat, or investment opportunity, this villa offers the perfect blend of comfort, convenience, and carefree Florida living. Schedule your private showing today !

665 Broadmoor Circle, Winter Haven

2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv. ⋅ 33880 Zip Code

Move right into this furnished home located in Oakwood Estates, a 55+ community. The carpet throughout the home is in excellent condition. The rooms are very spacious and inviting. The home has been very well maintained. The dishwasher was installed in 2018, the washer and dryer 2020, and the refrigerator in 2024. Enjoy the bonus room on the front of the home or sit and watch the world go by on the comfortable lanai. Oakwood Estates offers many activities and amenities. If you are looking for exercise, you can join in with the pool or indoor aerobics. Chair Yoga is offered twice a week, or play some pool volleyball. The tennis court has recently been refinished and there is a pickle ball group that meets three times a week. During the winter months, there are several exciting dances as well as many activities. If food is your thing, Oakwood offers potluck dinners, ice cream socials, and weekly coffee and donuts. If you are looking for full time or just part time, this is your opportunity to move into a wonderful community, conveniently priced.

4807 Plumwood Street, Winter Haven

3 Beds ⋅ 2 Baths ⋅ Traditions Ph 01 SubDv. ⋅ 33884 Zip Code

Welcome to 2820 Traditions Blvd S, located in the desirable 55+ gated community of Traditions at Lake Ruby in Winter Haven. This well-maintained Augusta model offers 3 bedrooms, 2 bathrooms, a spacious 2-car garage, and a peaceful pond-front setting. This home is perfect for Florida living! The open and comfortable floor plan provides beautiful pond views from the kitchen, dining area, living room, primary suite, and enclosed patio, allowing you to enjoy the tranquil Florida surroundings throughout the home. The kitchen offers ample cabinetry and workspace, while the spacious living areas create an inviting environment for both everyday living and entertaining. The split bedroom layout provides privacy for owners and guests alike. The enclosed patio is a wonderful space to relax, enjoy your morning coffee, or unwind while taking in the water views. Just outside your door, enjoy all that Traditions at Lake Ruby community provides, including a clubhouse, resort-style amenities, pool, fitness facilities, and recreational opportunities designed for an active adult lifestyle. Conveniently located in Winter Haven with easy access to shopping, dining, medical facilities, golf, and Central Florida attractions. Whether you are looking for a full-time residence or a seasonal retreat, this home offers comfort, convenience, and the opportunity to enjoy the relaxed lifestyle of Traditions at Lake Ruby.

2820 Traditions Boulevard S, Winter Haven

4 Beds ⋅ 3 Baths ⋅ Traditions Ph 02 SubDv. ⋅ 33884 Zip Code

Welcome to this beautifully maintained, energy-efficient 4-bedroom, 3-bath home in the highly desirable Traditions at Ruby Lake, a premier 55+ gated community offering the very best of Florida resort-style living. Situated on an oversized lot, this exceptional home features a desirable split floor plan Jack and Jill bathroom w/ walk-in tub and soaring high ceilings that create a bright, open, and spacious feel throughout. Thoughtfully upgraded for both comfort and efficiency, the home offers a spacious, expanded screened lanai with brick pavers—the perfect outdoor retreat for entertaining or enjoying a quiet evening—enhanced by customizable LED lighting to create the ideal ambiance. Energy-saving features include foam-core insulation in the concrete block walls, new Andersen windows, and a freshly painted exterior. Inside, you'll find hardwood flooring in the primary bedroom and front bedroom, which also makes an ideal home office. The kitchen is beautifully appointed with custom cabinetry, granite countertops, slate stainless steel appliances, and abundant storage. Custom maple shelving in the pantry, laundry room, and both linen closets adds both elegance and functionality. The primary bath also features granite countertops, completing the home's high-quality finishes. Designed for comfortable everyday living and effortless entertaining, this home offers generous living spaces that provide both privacy and flexibility for family and guests. HOA dues provide exceptional value and include weekly lawn and landscape maintenance, Spectrum TV service, and exterior house painting every seven years. Residents also enjoy full access to the community's impressive lakefront clubhouse, featuring a resort-style pool and spa, sauna, showers, a fully equipped fitness center, staffed front desk, library, business center, billiards room, craft room, and a spacious ballroom that hosts meetings, dances, entertainment, guest speakers, clubs, and social events. Outdoor amenities are equally impressive and include tennis, basketball, bocce ball, shuffleboard, pickleball, three community boat docks, a picturesque lakeside gazebo, and a paved walking path along the lake—perfect for morning strolls or evening exercise. If you're looking for a move-in-ready home with exceptional upgrades, low-maintenance living, and an active, resort-style lifestyle, this is the one you won't want to miss!

4132 Martindale Loop, Winter Haven

3 Beds ⋅ 2 Baths ⋅ Lake Ashton West Ph I SubDv. ⋅ 33884 Zip Code

HOME FOR SALE IN LAKE ASHTON! Is 4052 Phoenician Way, Winter Haven, Florida YOUR next address? This 3 Bedroom, 2 Bath home with Golf Cart Entry is located on a large premium lot that abuts to the 13th Fairway of Lake Ashton's West Golf Course. The view from the wrap around covered and screened lanai includes a large pond that borders the 13th Hole with a farm pasture beyond. Home Highlights: CDD Debt Balance Paid in Full; Roof Replaced 2022; Water Heater Replaced 2022; A/C Heat Pump Replaced 2019. This home offers excellent curb appeal with a Widened Drive Way, Poured Curbing, Well Maintained Mature Landscape with Landscape Rock, Quoined Corners, Bay Window on the Front Bedroom, and arched Screened Entry. A paver walkway on the right side of the home connects the access door of the golf cart garage to the rear lanai. The interior of this home is warm and inviting with an Open and Spacious Living area. The Foyer, Dining, LR and Kitchen flow seamlessly together making entertaining a "breeze" in this home. The beautiful Bruce interlocking Engineered natural oak floors and the Plantation Shutters on the Side Lights of the Front Entry Door, Double Sliding Glass Doors in the Living Room, Bedroom 2 and Primary Bedroom accent the interior of this home- adding a touch of class. Crown molding gives definition to the Open Living area. The kitchen upgrades include: Granite counter tops, Maple Cabinets with raised panels, 3 banks of drawers, crown molding and a pantry. The refrigerator, microwave and disposal were replaced in 2026 and the range was replaced in 2023. A breakfast bar/snack bar and Dining areas are perfect for entertaining friends and family. Enter thru the 8' Front entry door with Eyebrow window above. To the left of the foyer are Bedrooms 2 and 3, a Linen Closet in the Hallway and a Guest Bathroom with shower/tub combo, accent window and comfort height vanity. A pocket door provides privacy to the Guest Bedroom area. The EXTENDED Primary Suite is located on the back on the home. It's the perfect place to relax after a long day in the sun. The Primary Suite offers a spacious sitting area and En-Suite with His/Her Walk in Closets, His/Her Separate Vanities, a large corner Soaking tub, a separate water room with a walk in shower with glass doors and linen closet. The laundry room is easily accessible from the garage and kitchen. It has cabinets for storage, a wash tub and the washer/dryer will be included in the sale of the home. The double car garage has hang down storage racks, attic access, storage cabinets, and an access door to the outside. There is a motorized screen on the garage door and a separate entry for the golf cart. The outdoor living space is a destination location in this home. The view is peaceful and the space is cozy with paver floor, ceiling fans and TV hook up. Make an appointment to tour this home today! 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!

4052 Phoenician Way, Winter Haven

2 Beds ⋅ 2 Baths ⋅ Cypresswood Eagle Pond Condominium SubDv. ⋅ 33884 Zip Code

Don't miss the opportunity to own this lovely GROUND FLOOR Eagle Pond condominium in the highly sought-after gated community of Cypresswood Golf and Country Club that is PRICED TO SELL! Virtually maintenance-free Florida living doesn't get any better. Be greeted by 10-foot high ceilings, complimenting the open concept living area complete with expansive living and dining areas, including a kitchen breakfast bar. Walk-in closets in both bedrooms offer an abundance of space for organizing your belongings, and an en suite bathroom in the main bedroom for privacy and convenience. Enjoy the open-concept living area for entertaining friends and family and a private patio further compliment this delightful property. Immerse yourself in the outdoors on your private patio or take a walk, run, or bike ride to enjoy the natural scenery that abounds in this community. Cypresswood Golf and Country Club features a 24-hour manned guard gate, 18-hole championship golf course, junior Olympic-sized community pool, lighted tennis/pickleball/basketball courts, clubhouse, restaurant, pro-shop, event space, and so much more. The low monthly HOA fee includes all exterior and grounds maintenance, pest control, trash collection, and use of the pool and tennis amenities. Residents also enjoy a discount on daily golf and annual membership! 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!

1502 Eagle Pond Drive Unit 15, Winter Haven

3 Beds ⋅ 2 Baths ⋅ Village/Spirit Lake Ph 01 SubDv. ⋅ 33880 Zip Code

Saltwater pool. Boat parking. Private community boat ramp. Welcome to 315 Lanceolate Drive, a beautifully updated 4-bedroom, 2-bath home located in the gated community of The Village at Spirit Lake. Inside, you'll find a completely renovated kitchen and beautifully remodeled bathrooms, creating a fresh, modern feel while maintaining a comfortable and functional layout. Step outside to your own private retreat featuring a sparkling saltwater pool, screened lanai, and a fully fenced backyard—perfect for relaxing, entertaining, or enjoying Florida's year-round sunshine. The second bathroom provides direct access to the pool area, adding convenience for family and guests. Need extra space? The garage has been converted into two air-conditioned bonus rooms, offering incredible flexibility for a home office, gym, hobby room, playroom, or additional storage to fit your needs. The extended driveway provides the perfect place to park your boat, and residents of The Village at Spirit Lake enjoy exclusive access to a private community boat ramp on Spirit Lake. The neighborhood also features a brand-new playground, pickleball courts, a basketball court, clubhouse, gated entrance, and a very reasonable HOA. Ideally located just minutes from the Polk Parkway, commuting to Lakeland, Tampa, or Orlando is a breeze. The home is also located in unincorporated Polk County, allowing you to enjoy the benefit of county taxes only. Conveniently close to shopping, dining, schools, and Legoland Florida Resort, this move-in-ready home offers the perfect blend of updated finishes, flexible living space, and the Florida lifestyle you've been looking for. Schedule your private showing today and discover everything this exceptional home has to offer.

315 Lanceolate Drive, Winter Haven

2 Beds ⋅ 2 Baths ⋅ Lakeridge Condo SubDv. ⋅ 33881 Zip Code

NEW LISTING IN CENTRAL FLORIDA. CONDO IN 55+ Gated Community. This condominium provides 1.347 SF of living area 2 bedrooms, 2 baths, Bonus room with views of Spring Lake & is located in the beautiful City of Winter Haven. Lakeridge Condominiums offers a maintenance free lifestyle with heated pool, tennis, shuffleboard, community room, gated secured entrances and covered assigned parking space. Water, sewer, cable, internet, trash removal and use of recreational facilities are included in the monthly fee. This well appointed move in ready condo has a large bright kitchen with lots of cabinets, great counter space, appliances and pantry closet. The kitchen overlooks the great room that also adjoins the additional bonus area and storage closet. The primary bedroom has a walk in closet & bathroom with a walk in shower. Beautiful views of Spring Lake can be enjoyed from the Primary bedroom & living areas. Washer/Dryer are included. Convenient to shopping, groceries & restaurants. Extra assigned storage bin on same floor. Lakeridge Condominiums is an age restricted, well maintained & well managed community.

1776 6th Street Nw Unit 807, Winter Haven

3 Beds ⋅ 3 Baths ⋅ Hartridge Hills SubDv. ⋅ 33881 Zip Code

ARE YOU AN AIRCRAFT OWNER, PILOT, FLYING ENTHUSIAST AND/OR LOOKING FOR ACCESS TO THE CHAIN OF LAKES? Relax and enjoy life in this attractive 2383 SF 3BR/2.5 Bath home with study located in Hartridge Hills, a gated community with boat ramp and dock on Lake Hartridge, adjacent to the Winter Haven airport and near Jack Brown Seaplane Base! The community features CUSTOM EXECUTIVE STYLE homes! When built, this amazing home won the following parade of Homes Awards: Home of the Year; Best Kitchen; Best Master Bath; Best Exterior; Best Overall Quality; and, Best Floor Plan! The home features an open floor plan with split bedrooms, crown molding, volume ceilings, interior laundry room and attractive tile flooring. The kitchen overlooks the dining area and offers granite countertops, wood cabinetry, stainless steel appliances and pantry closet. The primary suite has sliding glass doors leading to the covered lanai, two walk-in closets and en suite bathroom with separate vanities, garden tub, walk around shower and a water closet. Most recent updates include: new landscaping May 2026; new refrigerator June 2025; installation of irrigation well 2025; repainting interior walls, trim and doors 2022; and installation of New 30 year Architectural Shingle Roof April 2022. The Community Offers a BOAT RAMP & DOCK on LAKE HARTRIDGE providing residents access to the CHAIN OF LAKES! HOA fee maintains streets, common areas, lights, gate, boat ramp & dock and mowing and fertilization of yards!! Centrally located with easy access to shopping, restaurants, medical facilities and surrounding towns.

220 Hartridge Hills Dr, Winter Haven

3 Beds ⋅ 2 Baths ⋅ Morningside SubDv. ⋅ 33884 Zip Code

Every Detail Has Been Thoughtfully Designed. Every Upgrade Has Been Thoughtfully Completed. Welcome to a home where quality craftsmanship, modern style, and everyday comfort come together effortlessly. Nestled on a beautifully landscaped nearly half-acre homesite overlooking peaceful Garden Lake, this impeccably maintained 3-bedroom, 2-bath residence offers the perfect balance of privacy, sophistication, and smart-home convenience. A natural privacy hedge of mature hibiscus surrounds the backyard, creating a tranquil setting that is increasingly difficult to find. From the screened front entry to the spacious screened lanai, every space has been designed to embrace Florida living while showcasing the exceptional care invested throughout the home. Inside, the open-concept floor plan is warm, inviting, and filled with natural light. Smart-home technology allows you to control the lighting, electric fireplace, and garage door opener with ease, while tasteful finishes and thoughtful updates create a contemporary feel that is as functional as it is beautiful. The completely updated kitchen serves as the heart of the home, featuring granite countertops, a farmhouse sink, elegant 42-inch upper cabinetry, redesigned lower cabinetry, recessed lighting, stainless steel appliances, and a generous workspace. The open layout is ideal for entertaining while maintaining a warm, inviting atmosphere for everyday living. The attention to detail continues throughout with beautiful flooring, updated lighting, refreshed bathrooms with granite countertops and modern fixtures, energy-efficient Low-E replacement windows, and countless improvements that reflect exceptional ownership. Outdoor living is equally impressive. Relax year round on the newly screened lanai with its attractive epoxy floor and premium UV-protective screening provides the perfect place to relax while enjoying peaceful views of Garden Lake. This private outdoor retreat is sure to become a favorite gathering place. Significant improvements—including a Bryant HVAC system, water heater, energy-efficient Low-E windows, updated exterior paint, smart garage door opener, and numerous additional upgrades—offer the peace of mind every buyer is looking for. Completing the home is a long-lasting clay tile roof that adds timeless character and enhances the home’s exceptional curb appeal. Located within the highly sought-after gated community of Winterset, residents enjoy exceptional amenities including a heated pool and spa, clubhouse, tennis courts, beautifully maintained grounds, private boat ramp and dock on Lake Winterset, and access to the renowned Winter Haven Chain of Lakes—all with a low HOA. Thoughtfully updated. Beautifully maintained. Perfectly positioned. A home that feels brand new—without the wait.

120 Morning Glory Circle, Winter Haven

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