Winter Haven / Cypress Gardens Homes with Special Community Restrictions Community Features

Winter Haven / Cypress Gardens Homes with Special Community Restrictions Community Features

Welcome to Winter Haven, a picturesque gem nestled in the heart of Polk County, Florida. Known for its stunning chain of lakes, this vibrant city is a delightful blend of natural beauty, rich history, and modern amenities. Winter Haven is renowned for its family-friendly atmosphere and an array of recreational opportunities, making it an ideal place to call home.

One of the highlights of this region is the iconic Cypress Gardens, a historic attraction that showcases Florida's lush landscapes and botanical wonders. Although the original theme park has transformed over the years, the legacy of Cypress Gardens continues to thrive, with beautiful parks and gardens that invite exploration and relaxation. Residents enjoy access to a variety of outdoor activities, from boating and fishing to hiking along scenic trails.

If you're considering making Winter Haven your home, you’ll find a diverse selection of properties, including those with special community restrictions. These homes often come with unique community features designed to enhance your lifestyle. Expect well-maintained neighborhoods with amenities such as community pools, clubhouses, and recreational areas, fostering a strong sense of community among residents.

Living in a community with special restrictions often means adhering to guidelines that maintain the aesthetic and integrity of the neighborhood, ensuring a peaceful and harmonious environment. Whether you’re seeking a cozy family home or a luxurious lakeside retreat, Winter Haven offers something for everyone. Embrace the charm of this wonderful city, where every day feels like a vacation!

Newest Winter Haven / Cypress Gardens Homes with Special Community Restrictions Community Features

1321 Oakmont Drive, Winter Haven
$434,700
3 Beds ⋅ 2 Baths ⋅ P4940018 MLS
** CDD Debt Balance PAID IN FULL, saving you thousands! **A new four-season Sunroom was completed in April 2026. It is glass-enclosed with a separate HVAC mini-split and has beautiful new flooring. This home offers amazing curb appeal, with new landscaping on every side of the house, including lush privacy plantings in the back. The St. Marks floor plan has 3 Bedrooms and 2 Baths, plus a Den, spacious Laundry Room and a Double-car Garage with designated Golf Cart Entry. With 2,069 sq.ft. living area in the original house PLUS an additional 243 sq.ft. living area in the Sunroom, this OPEN and SPACIOUS home is ideal for entertaining friends and family. The tile plank flooring that appears "wood like" flows thru the LR, Formal Dining, Foyer, Kitchen, Dinette, Den, Sunroom and Laundry Rooms -- adding a touch of class to this truly charming home! The voluminous ceilings are enhanced with the 8ft. door openings in the home. The kitchen is enhanced with Granite countertops, soft close drawers and cabinets with newer hardware, stainless steel appliances, tiled backsplash, step-up breakfast bar with pendant lights, and abundant countertop space for food prep and display. The Dinette area, which is adjacent to the kitchen, is accessible from the Sunroom and the Den. The spacious Owners Suite occupies the left wing of the home and is a private retreat featuring His/Her walk-in closets and its very own En-Suite bath area. The Primary Bath offers His/Her comfort height vanities with Granite countertop and Newer Cabinet Hardware, a Walk-in shower w/glass door enclosure and Large soaking tub. The triple glass block allows an abundance of natural light into the space. A "Barn-Like" door on a smooth track system separates the Primary Suite from the Primary Bath. It's stylish and practical. On the right side of this Split Floor Plan home are Bedrooms 2 and 3 and the Guest Bath. The Guest Bath has a comfort height vanity, Shower/tub combo and Newer Hardware on the Cabs. It's perfectly positioned between the Guest Bedrooms. The laundry room is well designed and is the passage from the garage into the home. The laundry room has additional shelving for your storage needs. Hosting a Game Night or Want to Cozy Up with a Good Book? The brand-new SUNROOM would be the ideal place! It's accessible thru the TRIPLE SLIDERS in the LR & DOUBLE SLIDERS in the Dinette. ADDITIONAL UPGRADES: Whole House Gutter System, Automatic Screen (Skeeter Beeter) on the Garage Door, Storm Door on the front door, Pull Down Attic Ladder, new window dressings throughout the home, Six-Filter Reverse Osmosis Water System added to the Kitchen sink, Updated Painting in Several Rooms and Cabinet Handles in the Kitchen and Bathrooms. Lake Ashton has (2) clubhouses, (2) Golf Courses, Planned Activities and Resort Style Amenities. Residents enjoy 2 Swimming Pools (one Indoor & one Outdoor), Movie Theater, Bowling Lanes, Card, Craft and Billiard Rooms, Fitness Rooms, Media Rooms, Indoor Racquetball, Indoor 1/2 Court Basketball, Pickle Ball Courts, Tennis Courts, Shuffleboard Courts, Eagles Nest (an Eatery), a Pro Shop and MORE! Lake Ashton is a beautiful 55 Plus Community in Florida closely located to Shopping, Restaurants, Entertainment and Medical Facilities. MAKE AN APPOINTMENT TODAY TOUR THIS BEAUTIFUL HOME.

1321 Oakmont Drive, Winter Haven

5281 Pebble Beach Boulevard, Winter Haven
$279,900
3 Beds ⋅ 2 Baths ⋅ P4939964 MLS
Begin the next exciting chapter of your life in Lake Ashton, Central Florida’s premier 55+ active-adult community, where this beautifully maintained and tastefully updated 2-bedroom, 2-bath home with den offers the perfect combination of comfort, convenience, and Florida lifestyle living. Ideally situated on a desirable corner lot with a generously sized yard, this inviting home welcomes you with its attractive curb appeal and continues to impress with thoughtful updates and quality features throughout. The kitchen offers 42-inch upper cabinets and solid-surface countertops, while beautiful wood flooring flows through the living room and den, creating a warm and inviting setting for relaxing or entertaining. The bedrooms feature newer carpeting for added comfort, and important major improvements provide exceptional peace of mind, including a new air-conditioning system and electric water heater in 2018, a new roof in 2023, and exterior painting completed last year for a fresh, crisp appearance and added weather durability. The washer & dryer are newer. Best of all, this exceptional home is being sold turnkey, including the furniture, electronics, furnishings, golf cart, and charger, making it possible to move in and immediately begin enjoying the Florida lifestyle without the hassle of furnishing a new home. Adding even more value, the seller is offering a $4,500 credit at closing toward new kitchen appliances. Beyond your front door, Lake Ashton delivers an extraordinary resort-style lifestyle with two 18-hole championship golf courses, a 26,000-square-foot clubhouse, a state-of-the-art health and fitness center, indoor and outdoor swimming pools, pickleball courts, a bowling alley, and an impressive calendar of clubs, activities, social events, and opportunities to make new friends. With its desirable corner-lot setting, spacious yard, numerous updates, turnkey convenience, golf cart, and access to one of Central Florida’s most sought-after active-adult lifestyles, this is a home that deserves to be experienced in person. Schedule your private showing today and discover how enjoyable your next chapter could be at Lake Ashton.

5281 Pebble Beach Boulevard, Winter Haven

4075 Bedford Avenue, Winter Haven
$349,001
2 Beds ⋅ 2 Baths ⋅ P4939922 MLS
Welcome to Traditions, a premier 55+ maintenance-free gated community, where resort-style living meets everyday comfort and convenience! This wonderful 2-bedroom, 2-bath home with a den offers Eco Smart construction and an exceptional location just steps from the community clubhouse and directly across the street from the boat ramp. A charming screened-in front entry welcomes you into this beautifully appointed home. Step inside to the spacious Great Room, featuring elegant crown molding and porcelain plank flooring. Oversized glass sliding doors provide an abundance of natural light and open seamlessly to the screened-in lanai, creating an effortless flow between indoor and outdoor living. The gourmet kitchen is truly a chef’s delight, showcasing timeless white shaker cabinetry accented with crown molding and brushed-nickel hardware, complemented by a beautiful glass-tile backsplash. The center island features luxurious quartz countertops and pendant lighting, creating both a stylish focal point and functional workspace. A walk-in pantry and stainless-steel appliance package provide additional convenience and storage. The charming breakfast nook offers the perfect spot for casual dining. Designed for entertaining, the open-concept floor plan allows the formal Dining Room to flow naturally into the Great Room. The versatile Den is an inviting retreat with beautiful views overlooking Lake Ruby, making it an ideal home office, reading room, or additional living space. The Primary Bedroom Suite offers a peaceful retreat, featuring a tray ceiling, wall-to-wall carpeting, and a generously sized walk-in closet. The luxurious Primary Bath features a comfort-height vanity with dual sinks, quartz countertops, private water closet, and a handicapped-accessible tiled shower beautifully finished with decorative Listello tile and glass enclosure. Throughout the home, crown molding and graceful arched entryways add architectural detail and timeless elegance. Step outside to the generously sized screened-in lanai, beautifully finished with pavers and offering a peaceful space to relax, entertain, and enjoy the Florida lifestyle. Additional features include a Laundry Room with cabinetry, washer and dryer, keyless smart-lock entry, smart thermostat, double-pane Low-E windows, AO Smith hybrid water heater, screened front entry, exterior carriage lighting, architectural shingle roof, radiant heat barrier, gutters, exterior stone facade, and paved walkway & driveway. The two-car garage features a garage door opener for added convenience. Traditions offers an exceptional active-adult lifestyle with an impressive array of amenities and planned activities. Residents enjoy a lakefront clubhouse, dock and boat ramp, heated swimming pool and spa, ballroom, billiards, meeting room, library, computer room, craft room, dog park, tennis courts, basketball court, bocce, shuffleboard, fitness center, aerobics studio, and so much more. The monthly HOA fee includes lawn service, cable, internet, and exterior house painting, providing added value and making maintenance-free living truly effortless. With its coveted location near the clubhouse and boat ramp, Lake Ruby views, this property offers the perfect combination of resort-style amenities, beautiful surroundings, and everyday convenience.

4075 Bedford Avenue, Winter Haven

3541 Raleigh Drive, Winter Haven
$350,000
3 Beds ⋅ 3 Baths ⋅ P4939900 MLS
Discover exceptional Florida living in this fabulous Eco Smart 3-bedroom, 3-bath home with a den, ideally situated in the premier gated active-adult community of Traditions at Lake Ruby. Designed with comfort, efficiency, and entertaining in mind, this beautifully appointed home offers an impressive array of upgrades and thoughtful features. The desirable split-bedroom floor plan provides privacy and versatility, including a spacious Junior Bedroom Suite with its own ensuite bath—perfect for visiting family or guests. The well-equipped kitchen is a chef’s delight, featuring a center island with pendant lighting, fingerprint-resistant stainless-steel appliance package, recessed lighting, and 42-inch white upper cabinetry enhanced with crown molding, soft-close hinges, and brush nickel hardware. A generous walk-in pantry provides additional storage, while the pull-out cabinet organizers keep everyday items conveniently within reach. The spacious Living Room features wood laminate flooring and triple glass sliding doors that open to the extended lanai, seamlessly blending indoor and outdoor living. The open-concept design also incorporates a dedicated Dining Room and cheerful breakfast nook, providing plenty of space for family gatherings and entertaining. The generously sized Primary Bedroom Suite is enhanced with laminate flooring and dual walk-in closets featuring deluxe closet organizer systems. The luxurious Primary Bath offers a handicapped-accessible tiled shower with glass enclosure, comfort-height vanity with dual sinks, and linen closet for additional storage. Outdoor entertaining is effortless in the oversized screened lanai, featuring decorative stamped-concrete flooring, retractable solar screens and a built-in buffet and BBQ Grill—perfect for enjoying Florida’s year-round outdoor lifestyle. Additional amenities include a versatile Den/Office, Laundry Room with cabinetry, washer and dryer, ceiling fans with remote controls, and extensive storage throughout. Energy-efficient features include solar panels with a monthly solar expense of approximately $209, a 15-SEER HVAC system, AO Smith hybrid water heater, Low-E windows, radiant heat barrier, and architectural shingle roof installed in 2026. A stone facade, decorative stone curbing, and paved driveway add to the home’s impressive curb appeal. Additional upgrades include smart-lock entry, whole-house generator, retractable garage screen, keyless garage entry pad, and a two-car garage equipped with three overhead storage racks, workbench with matching cabinetry, and an overhead solar skylight. Traditions at Lake Ruby offers an exceptional active-adult lifestyle with an impressive selection of amenities and planned community activities. Residents enjoy a lakefront clubhouse, dock and boat ramp, heated swimming pool and spa, ballroom, billiards, meeting room, library, computer room, craft room, dog park, tennis courts, basketball court, bocce, shuffleboard, fitness center, aerobics studio, and so much more. Conveniently located near shopping, medical facilities, and major transportation routes, Traditions at Lake Ruby offers the perfect combination of resort-style amenities, energy-efficient living, and everyday convenience. HOME CAN BE PURCHASED FURNISHED

3541 Raleigh Drive, Winter Haven

6136 Pebble Beach Boulevard, Winter Haven
$549,999
3 Beds ⋅ 3 Baths ⋅ P4939770 MLS
Virtually Staged. *GOLF COURSE and WATER VIEWS*** Located behind the secure gates of the coveted 55 + community of Lake Ashton, the water views from the covered and screened lanai are superb! Built in 2019, this home offers TWO SUITES, ONE GUEST BEDROOM and THREE BATHS. This split floor plan home offers great curb appeal with a FRESH NEW EXTERIOR COAT OF PAINT, Paver Driveway and Well Maintained Landscape. The lawn is "watered" by an irrigation system. As you enter thru the double glass doors of this home you are greeted by a large open floor plan offering expansive views of the golf course and lake beyond. The water views from this coveted lot location are spectacular! The living room, formal dining area and kitchen flow seamlessly together in this modified ASHTON Floor plan home, making entertaining easy and fun! The spacious Living Room has a tray ceiling, floor outlets, ceiling fan and triple sliders that stack and open to the covered and screened lanai. A formal dining area is located to the left of the front entry and the arched double windows add a touch of class! The Kitchen features 42" wood cabinetry, breakfast bar, pendant lighting, granite countertops, SS appliances (microwave replaced Sept. 2026) and ample counter top space for food prep and food display. The Dinette area is conveniently located off of the kitchen and the double windows provide an abundance of natural light into the home. Double sliders provide access to the lanai from the dinette area. The spacious and oversized Primary Suite with double door entry makes up the right wing of the home. It showcases two large walk-in closets, a separate water closet with window, a linen closet, a large, tiled walk in shower with grab bars and a tiled bench to sit on. The vanity with double sinks compliments the bathroom area. The Primary Suite with trey ceiling and ceiling fans can accommodate a separate sitting area for relaxation or larger bedroom furniture. The 2nd Suite with double door entry is on the left side of the home. It's accessible from the dinette area and from the hallway that leads to the 3rd Bedroom/3 Bath. The 2nd Suite has a private bath and built in closet. The 2nd Suite Bath features a comfort height vanity, walk in shower with glass enclosure, grab bars, foot rest and comfort height toilet. Overnight Guests will enjoy their own bedroom and bath with shower/tub combo and comfort height vanity. The Laundry Room (FLEX ROOM) is spacious and well designed with a wash tub and portable storage units for your personal items. The washer/dryer are included in the sale of this home. The outdoor living space offers a delightful place for entertaining. There are two OPTIONS: You can enjoy the covered portion of the lanai or the extended/uncovered screened lanai with direct views of the golf course and lake. The double car garage is sizeable and there is a separate golf cart entrance. The home also has a WHOLE HOUSE GENERAC- this is a huge bonus! ADDITIONAL IMPROVEMENTS to this home include: NEW INTERIOR PAINT and NEW LUXURY VINYL FLOORING. The community of Lake Ashton is a hidden treasure with an aura of peace and tranquility, and offers 2 golf courses, tennis courts, 2 pools (one indoor and one outdoor) movie theater, bowling lanes, card, craft and billiard rooms, fitness centers, pickleball courts, indoor basketball, indoor racquetball, numerous recreational activities, and restaurants. Make an appointment today to TOUR THIS HOME!

6136 Pebble Beach Boulevard, Winter Haven

3023 Caneel Street, Winter Haven
$235,000
2 Beds ⋅ 2 Baths ⋅ TB8504638 MLS ⋅ Na BLDG.
Welcome to the vibrant lifestyle of Traditions, one of Winter Haven’s most desirable gated 55+ communities! Built in 2020, this impeccably maintained villa offers 2 bedrooms, 2 bathrooms, and 1,385 sq. ft. of beautifully designed living space that perfectly blends comfort, elegance, and low-maintenance Florida living. Step inside to an inviting open-concept floor plan filled with natural light, high ceilings, and stylish ceramic tile flooring throughout the main living areas. The spacious living and dining areas are ideal for entertaining guests or simply relaxing in comfort. The modern kitchen is a standout feature, showcasing solid wood cabinetry, granite countertops, stainless steel appliances, and generous prep space for everyday living and special gatherings alike. The spacious primary suite offers a large walk-in closet and a private en-suite bath designed for comfort and convenience. Sliding glass doors lead to a screened-in porch where you can unwind and enjoy Florida’s beautiful weather year-round. Living in Traditions means enjoying an exceptional array of resort-style amenities, including a lakeside heated pool, elegant clubhouse, fitness center, tennis, pickleball, and shuffleboard courts, plus private access to Lake Ruby with a community boat ramp and dock. Even better, the HOA covers exterior maintenance, lawn care, and high-speed internet, allowing you to truly enjoy a carefree lifestyle. Ideally located near shopping, dining, hospitals, and Legoland, this stunning villa offers the perfect opportunity to enjoy the best of Central Florida living. Don’t miss your chance to own a beautiful home in one of Winter Haven’s premier active adult communities!

3023 Caneel Street, Winter Haven

1108 Sawgrass Drive, Winter Haven
$422,999
2 Beds ⋅ 2 Baths ⋅ S5149437 MLS
This is a must see charming oasis located behind the secure gates of Lake Ashton, you don’t want to miss this opportunity of becoming an homeowner in this Exclusive 55+ community in Florida, comes with a upgraded custom13’6 x 28’ saltwater pool with propane heater and expanded screened enclosure that measures 44’ x 24’ tankless propane water heater, and gas hookup for an outdoor kitchen in Lake Ashton! If you are seeking a stunning 2-bedroom, 2-bath property this is the one it sits on the Lake Ashton West golf course and this environment for Living certified Green home features several builder upgrades PLUS extensive builder and owner upgrades Inside, you’ll find tile flooring throughout (no carpet), upgraded kitchen cabinetry with roll-out shelving, Calcatta Silestone countertops with beveled edge; custom kitchen pantry cabinet with roll-outs; under-cabinet lighting, custom closets in both bedrooms and laundry room plus a custom pantry storage. Additional features include custom closets, updated bathrooms with a walk-in shower and glass doors, remote-controlled blinds, upgraded lighting and fans, epoxy garage flooring, and enhanced landscaping Located in Lake Ashton, a premier 55+ community offering two 18-hole golf courses, a 26,000 + sq ft Health and Fitness Center, pickleball courts , a bowling alley, a restaurant and much more, activities are abundant in this exceptional community . Don’t miss this very special pool home. Schedule your showing today.

1108 Sawgrass Drive, Winter Haven

3890 Bedford Avenue, Winter Haven
$395,000
4 Beds ⋅ 3 Baths ⋅ L4961088 MLS
Welcome to TRADITIONS, an active 55+ gated community located in the heart of the state on Lake Ruby. From swimming laps in the olympic size pool, casting a line at the lake, swinging a pickleball racquet or utilizing the fitness room and scheduled classes, there is plenty to do to stay in shape. If you prefer a more relaxed day, the clubhouse provides plenty of social spaces for card games, crafting, puzzles and reading a book. The community has planned monthly activities, they even plan a yearly community cruise if that's your vibe. You don't need to leave the community to find something to do, however; Disney and Universal Studios are nearby and you can reach either coast in less than two hours. The community is close to shopping (Publix coming soon), medical facilities, Legoland and the quaint downtown area of Winter Haven with boutique shops and local restaurants. This community is truly the ultimate 55+ lifestyle. The monthly dues include: community amenities, Spectrum cable and internet, lawn maintenance, common area maintenance, and exterior paining every 8 years. Now for the house: This is a Kennedy model floorplan, one of the most sought after in this community. It is a SHOW STOPPER from top to bottom and these Sellers have executed great care during their ownership. You will appreciate some of the additions they have made such as the extended rear screened lanai with Coolaroo shades and a motorized hurricane shutter. They also extended a paver BBQ area for those who like to grill. They added overhead storage racks in the garage and if you are an angler you will appreciate the storage system for the fishing poles! They have also added a motorized screen door for the days that you want to tinker in the garage and keep the bugs out. The exterior was just painted in 2025. The lawn is manicured with professional landscape edged flower beds and best of all the grass is maintained by the HOA. Step inside the front door to be instantly impressed with the high ceilings. The space is open enough for great entertaining but also offers space to spread out when needed. Ceramic tile in all the wet areas and living spaces with 5 inch baseboards and crown molding give the feeling of luxury. Recessed lighting, pendant lights as well as good window placement bring good lighting into the space. The kitchen is spectacular. 42 inch upper cabinets, quartz counters, walk in pantry and preparation island make the space functional for the chef and easy to entertain in. There are three dining space choices: formal dining area, breakfast nook and a breakfast bar providing with plenty of seating. The living room flows perfectly from the triple sliding door onto the lanai. The wall mounted TV's convey. The floorplan also offers a triple split bedroom plan. The primary bedroom offers an ensuite and the walk in closet has custom built in shelving. The ensuite has dual sinks, private commode room, linen closet and soaking tub. The walk in shower has no step and has nice glass doors. The 2nd and 3rd bedrooms share a guest bath with dual sinks and the 4th bedroom has a private ensuite. You truly have to see this home to appreciate its flow, style, tidiness and all the features that make this place a HOME! If 55+ living in Florida is what you have been dreaming of, you just found it! Come make some new Traditions!

3890 Bedford Avenue, Winter Haven

Start Your Search