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 stunning chain of lakes, vibrant community, and a lifestyle that perfectly blends relaxation and recreation. With its picturesque landscapes, Winter Haven offers a unique blend of small-town charm and modern conveniences, making it an ideal destination for families, retirees, and anyone seeking a peaceful yet engaging environment.

One of the standout features of Winter Haven is its collection of gated communities, providing residents with both security and a sense of exclusivity. These gated neighborhoods, while lacking a guard at the entrance, boast beautifully maintained landscapes and a welcoming atmosphere. Residents enjoy the peace of mind that comes with living in a secured environment, where community bonds are strong and neighbors become friends.

Homes in these gated communities are thoughtfully designed, offering a range of styles and sizes to suit diverse lifestyles. From spacious single-family homes to cozy villas, each property reflects the warmth and charm of the area. Many homes feature modern amenities, private backyards, and access to community parks, walking trails, and recreational facilities.

Living in Winter Haven means embracing an active lifestyle. Residents can indulge in boating, fishing, and picnicking along the serene lakes, or explore the local shops, restaurants, and cultural attractions that make this city so vibrant. Whether you're enjoying a leisurely day at Legoland Florida or taking in the natural beauty of the local parks, Winter Haven truly offers something for everyone. Discover your dream home in this beautiful city and experience the perfect blend of community, comfort, and Florida sunshine!

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

$125,000
2 Beds ⋅ 2 Baths ⋅ Lakeridge Condo SubDv. ⋅ 33881 Zip Code
Virtually Staged. Virtually staged bedroom. CENTRAL FLORIDA LAKE VIEW CONDO- THIS IS THE ONLY GATED 55+ CONDOMINIUM COMPLEX IN WINTER HAVEN. (Slightly younger buyer could possibly get approved.) NEW ENERGY-EFFICIENT WINDOWS IN THIS IMMACULATE, MOVE-IN READY 2 BEDROOM 2 BATH CONDO. WATER HEATER is 2025 & CENTRAL AIR CONDITIONER is a 2020. The kitchen is larger than most condo kitchens & the unit has a total of 1,347 sq. ft. of living area. MONTHLY FEE INCLUDES-WATER, SEWER, CABLE, FIBER OPTIC INTERNET, TRASH REMOVAL, CONDO RESERVES & use of recreational facilities- HEATED POOL, tennis, shuffleboard, community room, gated entrances & covered assigned parking space. All appliances & washer/dryer are included. The 26'x14' great room adjoins the additional FL/bonus room with large storage closet. The 16X14 foot master bedroom easily accommodates a king-size bed & has a walk-in closet & en-suite bathroom with walk-in shower. The 2nd bedroom includes a space-saving drop-down Murphy bed. The 2nd bathroom has a tub/shower combination. The linen closet is near the washer & dryer for convenience. Lakeridge is close to shopping, places of worship, groceries, restaurants, medical offices & hospital. Extra assigned storage on the same floor. Social activities available, if you wish to participate. Lakeridge is well-maintained, well-managed & passed inspections & studies with flying colors. Electric car charger on site for owners use. YOU ONLY HAVE TO PAY FOR YOUR ELECTRICITY HERE, AS EVERYTHING ELSE IS INCLUDED IN THE MONTHLY FEE. ONE SMALL PET MAY BE APPROVED. NON SMOKING PROPERTY. Quick Closing is available. Information believed to be accurate but not guaranteed. Measurements are approximate.

1776 6th Street Nw Unit 409, Winter Haven
$360,000
4 Beds ⋅ 2 Baths ⋅ Terranova Ph Iv SubDv. ⋅ 33884 Zip Code
Virtually Staged. This Winter Haven one-story home offers a two-car garage. Included 100-Day Home Warranty with buyer activation

313 Terranova Boulevard, Winter Haven
$239,900
3 Beds ⋅ 2 Baths ⋅ Winterset 03 A Condo Ph 01 SubDv. ⋅ 33884 Zip Code
3 bedroom, 2 bath ground-floor end-unit condo home with gorgeous views of Lake Winterset and a private 1 car garage—the perfect combination in one of Winter Haven’s most desirable gated communities. Welcome to 701 Magnolia Place, a spacious lakeview residence designed for easy single-level living with approximately 1,180 square feet, durable luxury vinyl plank flooring, and a comfortable, open layout. The living room is anchored by a fireplace and flows naturally into the dining area, creating an inviting space for everyday living and entertaining. The kitchen features white cabinetry, soft close drawers, newer stainless steel appliances, generous counter space, and an adjoining breakfast nook. The primary suite is spacious, measuring approximately 11x16, with lake views, a private bath with walk-in shower, generous closet space and direct access to the back patio. Two additional bedrooms provide flexibility for guests, a home office, hobby room, or den—a combination that makes this 3-bedroom floor plan especially hard to find in Winterset. A second full bath with tub and shower combo completes the interior. Step outside to the private screened porch, where wide-open green space and beautiful Lake Winterset views create the perfect place to enjoy your morning coffee, unwind at the end of the day, and watch sunsets you truly have to see to believe. As an end unit, the home enjoys an added sense of openness and privacy, while the attached one-car garage provides valuable parking and storage. Beyond the residence, the community of Winterset delivers on the Florida lifestyle. 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. Ground-floor living, an end-unit location, three bedrooms, private garage, screened porch, Chain of Lakes access, resort-style amenities, and gorgeous Lake Winterset views—701 Magnolia Place offers a combination that is difficult to find.

701 Magnolia Place, Winter Haven
$655,000
4 Beds ⋅ 3 Baths ⋅ Eloise Pointe Ests Phase Two SubDv. ⋅ 33884 Zip Code
Welcome to Eloise Pointe Estates, an established gated community near the shores of Lake Eloise and the Winter Haven Chain of Lakes, just minutes from LEGOLAND Florida Resort. Tucked away at the end of a quiet cul-de-sac, this beautifully maintained 4-bedroom, 3-bathroom home offers 3,001 square feet of living space and an exceptional combination of privacy, comfort, and upgrades. Inside, the spacious kitchen features granite countertops, stainless steel appliances, custom solid-wood cabinetry, and beautiful flooring, with generous living and entertaining spaces throughout the home. The family room is equipped with built-in surround sound, and any mounted televisions will convey. The true showpiece is the private backyard retreat, featuring a heated pool surrounded by lush landscaping—perfect for relaxing, entertaining, or enjoying Florida living year-round. Major improvements include a newer roof, A/C system, carpet and padding, and updated pool equipment, providing added peace of mind for the next owner. The home is also equipped with a buried propane tank serving the indoor fireplace, on-demand hot water heater, gas stove, and outdoor grill connection—adding both comfort and efficiency. With its desirable cul-de-sac location, private pool, spacious floor plan, extensive upgrades, and proximity to shopping, dining, recreation, and Central Florida attractions, this Eloise Pointe Estates home is truly a standout. Schedule your private showing today and experience everything this exceptional property has to offer.

2428 Wildwood Court, Winter Haven
$337,900
3 Beds ⋅ 2 Baths ⋅ Lakeside Landings Ph 01 SubDv. ⋅ 33881 Zip Code
Welcome to your new sanctuary in Lakeside Landings, a 55+ resort style, low maintenance existence awaits!! This isn't just a 4-bedroom, 2-bathroom, 2-car garage house. It is an exclusive VIP pass to resort-style living in a gated community with only 44 other neighbors. Before you even step inside, stop and look up. Are those... yes, those are RAIN GUTTERS and a NEW ROOF!! In Central Florida, finding a house with both is like finding a unicorn, but this beauty has them! Step inside and experience the magic of a triple-split floor plan. It is perfect for maximum privacy when you need a break. Even better? The indoor laundry room is centrally located. The open-concept living area features a kitchen with stone countertops and stainless steel appliances. But the real showstopper is the view! Breathtaking conservation backdrop sets the stage while local birds put on a daily, free nature documentary. Screened-in and bug-free, sip coffee without swatting mosquitoes! Fenced, lushly landscaped, and fully optimized for your pet safety, the fenced back yard is well maintained for your pet! The owner's suite is an absolute fortress of comfort. It boasts dual closets and a massive walk-in shower. In fact, this bathroom is so huge you might actually mistake it for a ballroom dance floor. Need to escape your paradise? You are right off Highway 27 and I-4, minutes from Legoland and Central Florida attractions. Championship golf courses and world-class fishing. Shopping, restaurants, and places of worship. This home has everything the Florida lifestyle demands. Grab your sunglasses and give me a call before someone else beats you to it!

5852 Marsh Landing Drive, Winter Haven
$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
$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
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