Winter Haven Homes with Gated Community - No Guard Community Features

Winter Haven Homes with Gated Community - No Guard Community Features

Welcome to Winter Haven, Florida, a charming city nestled in the heart of Polk County, renowned for its picturesque lakes, vibrant community, and a lifestyle that effortlessly blends relaxation and recreation. With its rich history and a wealth of outdoor activities, Winter Haven is a hidden gem in Central Florida, making it an ideal destination for families, retirees, and everyone in between.

One of the standout features of Winter Haven is its collection of beautiful homes within gated communities. These neighborhoods offer a unique blend of security and serenity, allowing residents to enjoy the peace of mind that comes with living in a gated environment. Notably, many of these communities are designed without guard services, providing a more relaxed atmosphere while still ensuring privacy and exclusivity.

Imagine waking up to the gentle sounds of nature, with lush landscaping and well-maintained amenities at your doorstep. Residents of these gated communities often enjoy access to a variety of features, including sparkling swimming pools, serene walking trails, and recreational facilities that promote an active lifestyle.

Additionally, Winter Haven's strategic location means you're just a short drive away from Orlando's world-famous attractions, yet far enough to enjoy a tranquil suburban lifestyle. Whether you're looking for a cozy family home or a spacious retreat, the homes in Winter Haven's gated communities offer a perfect blend of comfort, style, and community spirit. Discover your dream home in this enchanting city, where every day feels like a vacation!

Newest Winter Haven Homes with Gated Community - No Guard Community Features

$369,900
3 Beds ⋅ 2 Baths ⋅ Hartridge Hills SubDv. ⋅ 33881 Zip Code
Move-In Ready Custom Home in a Gated Community Near the Airport Ideally located for aviation professionals seeking convenient access to the airport or for families looking for a safe, gated community, this beautifully updated custom home offers the perfect blend of comfort, style, and convenience. Built in 1988, this spacious home features an open floor plan with soaring ceilings, stunning exposed wood beams, solid wood doors, and matching wood baseboards that create warmth and character throughout. The split-bedroom layout provides privacy, while the attached two-car garage adds everyday convenience. The recently remodeled interior showcases numerous upgrades, including luxury vinyl plank flooring, fresh interior paint, and updated lighting throughout. The beautifully renovated kitchen features custom wood cabinetry, granite countertops, and a full suite of matching Whirlpool appliances. Both bathrooms have been tastefully updated with new wood vanities, Delta fixtures, Kohler toilets, and stylish tile finishes. The primary bedroom offers the comfort of new carpeting, and the home features smooth ceilings throughout—no popcorn ceilings. Additional highlights include generous laundry room storage, fresh exterior paint, and numerous major improvements for peace of mind. A new roof was installed in March 2026, along with new double-insulated windows, new irrigation, and professional landscaping. Every major update has been completed—simply move in and enjoy. The HOA fee is just $150 per month and includes lawn mowing and fertilization, making it easy to maintain a beautiful yard year-round.

218 Lake Hartridge Drive Nw, Winter Haven
$198,900
2 Beds ⋅ 2 Baths ⋅ Vienna Square SubDv. ⋅ 33884 Zip Code
Short Sale. CLOSE IN 60 DAYS OR LESS! QUICK and easy HECM Short Sale on this 2 bedroom 2 bath Vienna Square Villa with pond and wooded view. Located next door to the clubhouse! The charming kitchen has upgraded ivory cabinets, and quartz counter tops. The oak floors flow from the kitchen, and great room giving a warm quality finish. The roof was replaced in 2022. Sold strictly AS-IS. No renting for the 1st 2 years of ownership in this charming 55+ community. 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. Vienna Square is a beautifully maintained, amenity-rich community designed for easy living. Monthly fees include exterior paint, roof replacement, irrigation water, basic yard maintenance, and a Spectrum Internet/TV package. Residents enjoy access to a community pool, fitness center, billiards, movie nights, tennis and pickleball courts, and an active social calendar. Step inside, fall in love. Make it yours!

1307 Innsbruck Ct, Winter Haven
$114,995
2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv. ⋅ 33880 Zip Code
Welcome to 4063 Rolling Oaks in Winter Haven, located in Oakwood Estates, a desirable co-op 55+ community. This well-maintained 2 bedroom, 2 bathroom home offers a spacious and versatile floor plan featuring a bonus room and a Florida room, providing plenty of space for relaxing, entertaining, hobbies or a home office. Laminate flooring flows throughout the main living areas and bedrooms, while the Florida room features tile flooring. The dining room includes a built-in buffet with display cabinets and additional storage, creating the perfect space for showcasing your favorite pieces and hosting family and friends. The kitchen offers a convenient closet pantry for added storage, and both bedrooms feature generous walk-in closets. Exterior features include window awnings and an attached carport. A BRAND NEW ROOF was put on (08/2026). Oakwood Estates offers an affordable Florida lifestyle with low HOA fees that include water and trash service. Residents can also enjoy many amenities of this lakefront community including; two clubhouses, two swimming pools, an activity center with a pool table, tennis & pickleball courts, a mini golf course and a lake with fishing dock. Don’t miss this opportunity to own a home in a welcoming community conveniently located near shopping, dining, and all the great amenities and attractions Winter Haven is known for.

4063 Rolling Oaks Drive, Winter Haven
$209,900
Osprey Estates SubDv. ⋅ 33884 Zip Code
OSPREY ESTATES IS A SMALL, GATED COMMUNITY LOCATED IN BEAUTIFUL SE WINTER HAVEN, FLORIDA. THE COMMUNITY HAS A TOTAL OF FOUR LOTS--THREE HAVE UPSCALE RESIDENCES AND THIS IS THE LAST ONE AVAILABLE. THE LOT IS .75 ACRE. THIS LOCATION IS CLOSE TO SHOPPING, MULTIPLE RESTAURANTS, LEGOLAND AND BOTH TAMPA AND ORLANDO. HOA REQUIRES A MINIMUM 3,500 SQ FEET OF LIVING AND A MAXIMUM 5,500 SQ FEET OF LIVING--ALSO THE NEW BUILD MUST HAVE A THREE-CAR GARAGE. THERE IS A WELL ON THE PROPERTY FOR IRRIGATION.

Eloise Loop Road, Winter Haven
$495,000
4 Beds ⋅ 3 Baths ⋅ Hart Lake Hills Ph 01 SubDv. ⋅ 33884 Zip Code
Welcome to this beautifully maintained 4-bedroom, 3-bath pool home located in the highly sought-after gated community of Hart Lake Hills. Offering the perfect blend of comfort, efficiency, and Florida living, this home is designed for both everyday enjoyment and effortless entertaining.Step inside to an open and inviting floor plan featuring a spacious kitchen with stainless steel appliances, a gas range, abundant cabinetry, and plenty of counter space overlooking the main living areas. The generous primary suite provides a relaxing retreat with a well-appointed ensuite bath, while the split-bedroom layout offers added privacy for family and guests. Outside, enjoy the screen-enclosed saltwater pool and expansive lanai overlooking the large, fully fenced backyard. The outdoor space has also been thoughtfully updated with pavers installed on the back deck in 2019, the pool remarcited in 2019, and a new pool pump and salt cells added in 2024. Additional updates and features include a roof installed in 2017, A/C installed in 2019, fresh interior paint in 2020, a whole-home Generac generator, gas hot water heater, and solar panels for added energy efficiency and peace of mind. Perfectly situated near schools, shopping, dining, LEGOLAND Florida Resort, and Highway 27, this home offers convenient access to everything Central Florida has to give while tucked away in one of the area's desirable gated communities. Schedule your private showing today! Solar panel loan must be assumed by buyer.

651 Hart Lake Drive, Winter Haven
$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
$340,000
3 Beds ⋅ 2 Baths ⋅ Village/Crystal Beach SubDv. ⋅ 33880 Zip Code
Welcome to 1041 Brooks Way. Step inside to an open, thoughtfully designed floor plan that’s ideal for both relaxing and entertaining. The split-bedroom layout provides added privacy, while the spacious living areas flow seamlessly into the kitchen and dining space, creating the heart of the home. The primary suite offers a peaceful retreat with an en-suite bath and generous closet space. Outside, you’ll enjoy a large backyard with plenty of room to create your own outdoor oasis, whether you envision a patio, garden, play area, or future pool. Conveniently located near shopping, dining, schools, and everything Winter Haven has to offer. beautifully designed single-story home built in 2023, offering the perfect blend of modern comfort and everyday functionality. Featuring 3 bedrooms, 2 bathrooms, and 1,863 square feet of living space, this home sits on a spacious 0.24-acre lot in The Grove at Crystal Beach community. Don’t miss your opportunity to make this beautiful home yours. Schedule your private showing today!

1041 Brooks Way, 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
$229,900
2 Beds ⋅ 2 Baths ⋅ Winterset 01 A Condo 02 Amd SubDv. ⋅ 33884 Zip Code
Completely renovated ground-floor condo with beautiful lake views of Lake Winterset on the world-famous Winter Haven Chain of Lakes! Welcome to Winterset, where this stunning remodeled 2 bedroom, 2 bath condo 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 this unit is 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 expanded kitchen delivers the wow factor with elegant granite countertops, soft-close cabinetry with crown molding, black appliances including a gas range and dishwasher, a 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 primary suite offers beautiful lake views, a huge walk-in closet and a luxurious master bath with double vanity undermount sinks, granite countertop, sleek chrome 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. Stepping outside to the private screened porch you'll find the perfect spot to unwind while watching the water and the most amazing sunsets you have to see to believe. 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
$285,000
3 Beds ⋅ 2 Baths ⋅ Morningside SubDv. ⋅ 33884 Zip Code
Welcome to this beautifully maintained 3-bedroom, 2-bath home located in the highly desirable Morningside at Winterset, a 24/7 gated community offering comfort, security, and resort-style living. This spacious property features an inviting foyer that opens into a bright great room and dining area, enhanced by elegant plant shelves and sliding glass doors leading to a large all-weather screened porch with vinyl panels—perfect for relaxing year-round. The well-appointed kitchen offers abundant cabinetry, a breakfast bar, and a full appliance package including a smooth-top range, built-in microwave, dishwasher, and side-by-side refrigerator. The generous primary suite includes private porch access, a walk-in closet, and a luxurious bathroom with a jacuzzi tub. Additional highlights include a separate laundry room with washer, dryer, utility sink, and extra storage, plus a 2-car garage. The home features 16” ceramic tile throughout the main areas and neutral carpet in the bedrooms, creating a warm and comfortable feel. Residents of Winterset enjoy access to community amenities, including a clubhouse, pool, tennis courts, and beautifully maintained grounds. This home offers a wonderful blend of space, convenience, and community living in SE Winter Haven

140 Morning Glory Circle, Winter Haven
$309,000
3 Beds ⋅ 2 Baths ⋅ Traditions Ph 01 SubDv. ⋅ 33884 Zip Code
Every day feels like a vacation in this beautiful home located in Traditions, a sought-after 55+ gated lakefront community offering the best of Florida living. This move-in ready residence showcases pride of ownership from the moment you arrive, featuring a brick paver driveway and a meticulously cared-for interior. Inside, you’ll find updated stainless steel appliances, a water softener, and thoughtful upgrades throughout. The enclosed and cooled Florida room creates the perfect year-round retreat for relaxing or entertaining. Additional highlights include gutters, a painted garage floor, and a golf cart included for your convenience. Traditions offers an unmatched lifestyle with resort-style amenities, including community boat slips, a dock, and fishing pier with water access—perfect for lake lovers. Residents also enjoy a clubhouse, fitness center, heated resort-style pool, sauna, tennis and pickleball courts, dog park, and golf cart-friendly streets. Plus, you’re a minute from the new Publix, making everyday living effortless. If you’re ready to enjoy an active, low-maintenance lifestyle in a vibrant lake community, this home is a must-see.

4134 Bedford Avenue, Winter Haven
$619,000
5 Beds ⋅ 3 Baths ⋅ Hidden Creek SubDv. ⋅ 33880 Zip Code
Virtually Staged. Welcome to this stunning 5-bedroom, 3-bathroom pool residence located in the highly sought-after, gated Hidden Creek community of Winter Haven. Perfectly positioned just minutes from the Polk Parkway and LEGOLAND Florida Resort, and conveniently situated between Lakeland and Winter Haven, this home offers an ideal blend of comfort and unbeatable accessibility. Inside, you will find soaring ceilings, a smart split-floor plan, a dedicated office or bonus room, a large den, and a 2-car garage that delivers ultimate flexibility for modern living, complemented by brand-new carpet replaced in 2025. The beautiful kitchen features granite countertops and a convenient walk-in pantry, while the primary suite serves as a true private retreat featuring a deep soaking tub, separate walk-in shower, dual sinks, a vanity, and a massive walk-in closet. Situated on a generous 0.35-acre lot, the property offers rare privacy, as the home backs up to a preserve with peaceful natural views. The absolute crown jewel of the home is the expansive, screen-enclosed lanai and sparkling saltwater heated pool with a heated spa, creating an exceptional resort-style outdoor living space masterfully designed for effortless entertaining, relaxing weekend lounging, or simply enjoying the tranquil Florida breeze in total privacy. Schedule your private showing today and discover a rare gem in Winter Haven! NO CDD!

1020 Lena Run Court, Winter Haven
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