Winter Garden Homes with Gated Community - No Guard Community Features

Winter Garden Homes with Gated Community - No Guard Community Features

Welcome to Winter Garden, Florida—a charming city that beautifully blends small-town warmth with modern conveniences. Nestled just a short drive from the vibrant attractions of Orlando, Winter Garden is known for its picturesque landscapes, historic downtown, and a strong sense of community. With its lush parks, scenic lakes, and a thriving arts scene, this city offers a lifestyle that is both relaxed and enriching.

One of the standout features of Winter Garden is its array of gated communities, providing residents with an added layer of privacy and security. Among these, homes in no-guard gated communities offer a unique appeal. These communities are designed to foster a sense of camaraderie among neighbors while ensuring a peaceful living environment. Imagine coming home to a beautifully manicured neighborhood, where children can play freely, and evening strolls are a daily delight.

The homes in these no-guard gated communities boast a variety of architectural styles, from charming single-family residences to luxurious modern designs. Many properties feature spacious layouts, private backyards, and access to community amenities such as swimming pools, playgrounds, and walking trails. Living here means having the freedom to enjoy your home and community without the hustle and bustle of constant security checks.

With its excellent schools, thriving local businesses, and a calendar filled with community events, Winter Garden is more than just a place to live—it's a place to call home. Discover the charm of Winter Garden and experience the comfort and security of a no-guard gated community today!

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

580 First Cape Coral Drive, Winter Garden
$675,000
4 Beds ⋅ 3 Baths ⋅ Black Lake Park Ph 01 SubDv. ⋅ 34787 Zip Code
Virtually Staged. Welcome to Black Lake Park, one of Winter Garden's sought-after gated communities, where spacious family living, fantastic amenities and an enviable location come together to create the perfect Florida lifestyle! Offering 4 SPACIOUS BEDROOMS, 2 1/2 BATHROOMS, AND HUGE LOFT AREA, this beautiful home provides the ideal combination of comfort, space and functionality. The welcoming open-plan layout creates an easy flow between living spaces, making everyday family life effortless, and entertaining a pleasure. With NO CARPETS THROUGHOUT, NEWLY PAINTED INTERIOR and a NEW ROOF – INSTALLED DECEMBER 2024, this home offers even more appeal and peace of mind, with a clean, practical and easy-to-maintain living environment. Whether hosting friends, enjoying family time or simply relaxing at home, with 2834 sq ft there's room for everyone. It does not stop there. Step outside and discover what Florida living is all about! Your private fully fenced backyard retreat, features a NEW FABULOUS SALTWATER SWIMMING POOL AND SPA – INSTALLED DECEMBER 2025! Imagine soaking up the sunshine, cooling off on warm afternoons or unwinding in the spa after a busy day. With plenty of room for lounging, outdoor dining and entertaining this is an outdoor space you'll love coming home to! Life in Black Lake Park is something special! This FABULOUS, GATED, FAMILY-FRIENDLY COMMUNITY offers an outstanding range of recreational facilities, making it a wonderful place for families and those who enjoy an active outdoor lifestyle. Amenities include TENNIS COURTS, BASKETBALL COURTS, BASEBALL FIELDS, A COMMUNITY SWIMMING POOL AND PLAYGROUND, along with lovely walking paths, and COMMUNITY DOCK AND BOAT RAMP. Whether enjoying a family game, taking a leisurely stroll, spending time at the park or heading out onto the water, there's something for everyone to enjoy. It's a community where outdoor living, family fun and a wonderful neighborhood atmosphere come together. This LOCATION is hard to beat. Simply wonderful! Just minutes from the charm of Historic Downtown Winter Garden, where you'll find an abundance of restaurants, cafés, boutique shopping and the much-loved Winter Garden Farmers Market. Winter Garden Village is also close by, offering an excellent choice of shopping, grocery stores and everyday conveniences. For commuters and those who love to explore, easy access to the 429, Florida Turnpike and Highway 50 makes traveling around Central Florida very convenient. Walt Disney World and the area's world-famous attractions are also within easy reach, making this a fantastic location for enjoying everything that is available in Central Florida. Whether you're searching for your next family home, the perfect place to entertain or simply somewhere to enjoy everything the Florida sunshine has, this is an opportunity not to be missed. THIS HOME IS MOVE IN READY! COME AND DISCOVER THE LIFESTYLE WAITING FOR YOU IN BLACK LAKE PARK.

580 First Cape Coral Drive, Winter Garden

12922 Canopy Woods Way, Winter Garden
$1,525,000
5 Beds ⋅ 5 Baths ⋅ Canopy Oaks Ph 1 SubDv. ⋅ 34787 Zip Code
EXQUISITE MODEL SHOW HOME | 5 BEDROOMS | 4.5 BATHROOMS | TWO PRIMARY SUITES | POOL | 3-CAR GARAGE | GATED COMMUNITY Welcome to an exceptional residence where timeless Mediterranean architecture meets refined Florida living. Located within the exclusive gated community of Canopy Oaks, an intimate enclave of only 49 residences, this stunning former model show home represents the finest in architectural design, craftsmanship, and luxurious indoor-outdoor living. From the impressive grand entrance, this residence immediately makes a statement. The thoughtfully designed floor plan features 5 bedrooms, 4.5 full bathrooms, a private first-floor primary suite with wet bar, and a spectacular second-floor primary retreat, offering an unparalleled level of flexibility and privacy. The heart of the home is an impressive chef's kitchen, beautifully appointed with premium KitchenAid appliances, a 5-burner natural gas cooktop, abundant cabinetry, generous workspace, and an oversized walk-in pantry. The kitchen opens seamlessly to the expansive living, dining and custom wine cellar, creating an ideal setting for intimate dinners or entertaining. The first floor also features a dedicated den/office, elegant dining area, wine cellar, laundry room, and convenient half-bath powder room. A beautiful wood staircase leads to the second level, where luxury and entertainment continue. The expansive gathering room provides an inviting space for family and guests, while the fully equipped theater room creates an exceptional private cinema experience, complete with its own private beverage station. The upstairs primary suite is a private sanctuary, featuring a beautiful garden tub, private balcony, and its own refreshment bar—an indulgent retreat designed for comfort and relaxation. Three additional upstairs bedrooms provide generous accommodations, including one bedroom with its own adjacent full bathroom and two bedrooms connected by a convenient Jack-and-Jill bath. The home's extraordinary outdoor living spaces are equally impressive. The expansive screened-in lanai features custom wood ceilings, creating a beautiful extension of the interior living space. Beyond the lanai, a sparkling private pool is surrounded by elegant travertine decking and complemented by a spectacular custom summer kitchen, creating the ultimate setting for Florida entertaining, dining, and relaxation. Additional features include a Rampart security system, Generac Generator, Central vacuum, exceptional storage, and the quality and attention to detail expected of a showcase model residence. The Canopy Oaks models were recognized with three awards in the Parade of Homes, highlighting the exceptional design and craftsmanship found throughout this exclusive community. Perfectly positioned just minutes from Winter Garden Village and Historic Downtown Winter Garden, this home also offers convenient access to the Florida Turnpike, SR 429, and SR 408, providing an easy connection throughout Central Florida. 12922 Canopy Woods Way is more than a home—it is a statement of refined living. With its timeless Mediterranean architecture, two extraordinary primary suites, resort-style pool and outdoor living, premium entertaining spaces, and exclusive gated setting, this is a truly remarkable opportunity to own one of Winter Garden's exceptional residences. Call today to schedule your showing and experience its distinctive luxury and elegance firsthand.

12922 Canopy Woods Way, Winter Garden

3249 Sailing Pier Avenue, Winter Garden
$675,000
4 Beds ⋅ 4 Baths ⋅ Lakeview Preserve SubDv. ⋅ 34787 Zip Code
Virtually Staged. WELCOME HOME to the highly sought-after GATED COMMUNITY OF LAKEVIEW PRESERVE in Winter Garden! Featuring $125,000 IN UPGRADES AND IMPROVEMENTS, this beautifully maintained home offers 4 BR, 3.5 BA, 2,964 SFT, a 2-car garage, and an exceptional floor plan! Impressive curb appeal begins with an upgraded stone elevation, designer glass and wrought-iron front door, extended paver driveway, and freshly painted exterior (2025). Inside, a spacious formal living room with French doors makes an ideal home office or den, while the OPEN-CONCEPT GREAT ROOM flows seamlessly into the beautifully appointed kitchen featuring white cabinetry, matte black hardware, QUARTZ COUNTERTOPS, and generous entertaining space. Extensive upgrades include HIGH-END PORCELAIN TILE FLOORING throughout the downstairs and bathrooms, upgraded wood stair treads with wrought-iron balusters, plantation shutters, and quartz countertops throughout. The spacious FIRST-FLOOR PRIMARY SUITE features a stylish barn door leading to a luxurious bath with soaking tub, oversized glass-enclosed shower, dual vanities, and a large walk-in closet with custom built-ins. A convenient half bath and laundry room with extensive cabinetry and sink complete the first floor. Upstairs offers a LARGE BONUS ROOM with luxury vinyl plank flooring, a spacious SECOND ENSUITE BEDROOM with private full bath, and two additional bedrooms sharing a full hallway bath. Additional improvements include upgraded carpeting, custom cabinetry and storage, enhanced lighting and electrical features, professionally coated garage floor, and an EXTENDED 10' x 26' SCREENED LANAI perfect for relaxing or entertaining. Residents enjoy RESORT-STYLE AMENITIES including a clubhouse, fitness center, zero-entry pool, splash pad, playground, walking trails, picnic areas, and KAYAK LAUNCH WITH ACCESS TO JOHNS LAKE for kayaking, canoeing, and fishing. LOW HOA OF JUST $152/MONTH AND NO CDD FEE! Ideally located minutes from SR 429, Downtown Winter Garden, Winter Garden Village, Clermont, shopping, dining, entertainment, and major Central Florida highways. This exceptional home combines extensive upgrades, flexible living spaces, and an outstanding location in one of Winter Garden's most desirable gated communities. Schedule your private showing today!

3249 Sailing Pier Avenue, Winter Garden

13846 Fresh Ivy Street, Winter Garden
$679,000
2 Beds ⋅ 3 Baths ⋅ Del Webb Oasis Ph 3 SubDv. ⋅ 34787 Zip Code
Beautifully appointed and thoughtfully designed, this home offers an exceptional opportunity to enjoy the Del Webb Oasis lifestyle—with the **seller covering the buyer's HOA capital contribution fee!** From the moment you enter, you'll appreciate the attention to detail, sophisticated finishes, and inviting open-concept design. The beautifully appointed kitchen is a standout, featuring crisp white cabinetry, quartz countertops, stainless steel appliances, a gas cooktop, designer lighting, and an expansive center island with seating. The soft, coastal-inspired color palette, beautiful flooring, and thoughtfully selected finishes create a home that feels both elegant and comfortable. The kitchen flows effortlessly into the dining and living areas, making it equally suited for everyday living and entertaining. A dedicated private office or flex space offers additional versatility. Beyond the home itself, **Del Webb Oasis offers an exceptional 55+ lifestyle** with amenities designed for recreation, relaxation, and connection. At the heart of the community is a beautiful 12,000-square-foot clubhouse featuring an indoor/outdoor bar and tavern, coffee lounge, fitness center with Technogym equipment, yoga and movement studio, arts and crafts room, billiards, and gathering spaces. The on-site restaurant offers lunch and dinner on Wednesdays and Fridays, making it easy to meet friends and enjoy an evening out without leaving the neighborhood. Outdoors, residents enjoy a resort-style zero-entry pool with lap lanes, spa, poolside cabanas, pickleball and tennis courts, bocce ball, walking paths, and inviting social spaces. A full-time lifestyle director coordinates a vibrant calendar of neighborhood activities, clubs, fitness classes, trivia nights, social gatherings, and special events. Whether you want to stay active, explore new interests, or simply enjoy time with neighbors, there's always something happening. Ideally situated in Winter Garden, just minutes from Walt Disney World, shopping, dining, and major roadways, Del Webb Oasis offers the perfect combination of resort-style living and everyday convenience. **A beautifully finished home, an engaging community, and valuable seller-paid incentives—your next chapter starts here!**

13846 Fresh Ivy Street, Winter Garden

234 Woodfall Lane, Winter Garden
$1,219,170
5 Beds ⋅ 5 Baths ⋅ Winter Grove SubDv. ⋅ 34787 Zip Code
Under Construction. Welcome to Winter Grove in the charming city of Winter Garden. Located 1 mile from Winter Garden Village and 3 miles from historic downtown Winter Garden. This intimate gated new community features single-family homes without a CDD. Residents enjoy all the proximity to shopping, dining, and entertainment this area is known for. The new two-story Roseland home combines modern elegance with practical living, offering 5 bedrooms, an enclosed flex room, 4 full bathrooms, a powder room, and a 3-car garage. As you step through the double entry glass doors, you are immediately greeted by a striking foyer that rises to the second floor, setting the tone for the entire home. To one side, a spare bedroom en suite offers privacy for guests and loved ones on the first floor, while the formal dining room invites effortless entertaining. From there, you enter the heart of the home—a chef-inspired gourmet kitchen. Equipped with built-in KitchenAid stainless steel appliances, including double ovens, the kitchen is a dream for culinary enthusiasts. Soft-close cabinetry with clear glass uppers is paired with exquisite quartz countertops, creating a timeless and sophisticated look, while a spacious walk-in pantry ensures ample storage. The open-concept design effortlessly connects the kitchen to the gathering room and cafe, where soaring ceilings create an airy, light-filled space, perfect for both intimate gatherings and larger celebrations. The covered lanai offers a seamless transition to the outdoors, ideal for year-round entertaining. Also located on the first floor, is a “Multi-Gen Suite” offering a spacious bedroom with its own linen closet, walk-in closet, and attached bathroom complete with a glass enclosed shower and quartz countertops. Upstairs, the private owner’s suite spans one side of the home, creating a peaceful retreat. The owner’s retreat area, ideal for reading or unwinding, leads into the spa-inspired owner’s bath, where luxury knows no bounds. A frameless glass-enclosed shower, free standing tub, enclosed toilet, and double walk-in closets create a sanctuary of relaxation. The second floor also offers two additional spacious bedrooms connected by a Jack and Jill bathroom, ensuring both privacy and convenience, while a third bedroom enjoys its own en suite bath, providing an added level of comfort and luxury. The upstairs laundry room, with a utility sink and a brand new Whirlpool washer and dryer makes daily tasks a breeze. With an intelligently designed layout and meticulously curated finishes, this home offers the perfect balance of form, function, and style. It's the epitome of luxury living in a highly sought-after location, blending convenience, sophistication, and thoughtful design into a living experience like no other. Schedule a tour today!

234 Woodfall Lane, Winter Garden

13537 Splashing Isla Drive, Winter Garden
$430,000
3 Beds ⋅ 2 Baths ⋅ Del Webb Oasis Ph 2 SubDv. ⋅ 34787 Zip Code
Virtually Staged. Welcome home to carefree villa living in the beautiful 55+ community of Del Webb Oasis. Follow a delightful pavered walkway past lush landscaping to reach the covered front porch. Stepping inside reveals a generous foyer with plank tile flooring that extends throughout all living/wet areas right up to carpeted bedrooms. Inside the spectacular kitchen you will find 42" uppers, gorgeous quartz countertops, subway tile backsplash, tall crown cabinet molding, waste-basket pull out, soft close drawers, double roll-out trays, whirlpool appliances, an island with storage and electric, excellent lighting and attractive matte black hardware. Just off the kitchen is the cafe or dining area which then flows into the gathering room or living room. Three clerestory windows provide natural light into the living room which also has a floor outlet and LED downlights illuminating well the ebb and flow of life lived to the fullest. The split floor plan places the primary suite at one end of the home with two guest bedrooms and a guest bath at the other end. With a window view into the peaceful backyard, the spacious primary bedroom adjoins an en suite bathroom complete with a shower (note the built-in seat and glass shower door), dual sinks, water closet, linen closet and enormous walk-in closet. Two guest bedrooms can serve as office, den, library, craft room or hobby space in addition to providing a comfortable space for visiting guests. An attractive tile-surround for the tub/shower in the guest bathroom complements the single vanity and finishes perfectly. Near the door leading to the 2-car garage is the laundry room with pocket door, washer/dryer, ventilated shelves, CAT6 Telecom Data Port and a transom-style window. Triple sliders open to the covered and extended pavered lanai. Keyless entry for the garage. 2" faux wood blinds at all functional windows. A 5" Carbon Clean MERV 16 filter with Cabinet enhances the HVAC system. Adjacent to the home is a paved walking trail. Community amenities include an active, sprawling Clubhouse, resort-style pool as well as pickle ball and tennis courts. HOA fees also include exterior maintenance, landscaping, irrigation repairs, exterior painting and roof replacement. Schedule your visit to see all that this home has to offer today!

13537 Splashing Isla Drive, Winter Garden

2139 Tillman Avenue, Winter Garden
$825,000
4 Beds ⋅ 4 Baths ⋅ Bronsons Landing SubDv. ⋅ 34787 Zip Code
STOP YOUR SCROLL!!! It's not everyday a GORGEOUS home inside the beautiful gated community of Bronson's Landing is available but this Pool Home offers SO MUCH! This 4 bedroom PLUS OFFICE and POSSIBLE 5th BEDROOM home has 4 FULL bathrooms with multiple living spaces, multiple dining areas as well as an extra large 3 car garage. At the heart of the home is the spacious kitchen with an island, perfectly positioned between the main living areas and designed for both everyday life and entertaining. You’ll find granite counter tops, a large center island, double ovens, plenty of cabinetry, and a pantry. One of the best features is that the primary suite and three additional bedrooms are all located on the main floor. The primary bedroom feels like its own private retreat on it's own side of the house with two walk-in closets, dual vanities, a soaking tub, and separate shower. Being a split floor plan, 2 bedrooms share a Jack-and-Jill bathroom that makes this home super functional. This home can easily handle generational living. Upstairs, the over-sized bonus room with its own full bathroom gives you even more possibilities. Use it as a game room, movie room, guest suite, home gym, second office, or even a possible 5th bedroom. There is plenty of flexibility to make the space work for your lifestyle. The backyard is where the Florida lifestyle really shines! Step outside to your own private oasis with a screened saltwater pool, covered lanai, paver deck, and convenient pool bath. The home backs to a beautiful tree-lined green space, giving you extra privacy and a peaceful setting with no home directly behind you. Imagine starting the morning with coffee by the pool, spending the afternoon soaking up the Florida sunshine, and ending the evening relaxing under the lanai. And YES! Location matters! Bronson’s Landing is a sought-after gated community in one of Winter Garden’s most desirable areas, with access to highly regarded schools and an amazing Central Florida location. You’re close to Winter Garden Village, shopping, dining, 429, and all the charm of Historic Downtown Winter Garden. ALSO! Walt Disney World is just a short drive away, making spontaneous trips to the parks, dinner at Disney Springs, or a night watching fireworks that much easier! This home gives you the space of a true family home, the privacy of a beautiful gated community, your own Florida pool, and easy access to everything that makes Winter Garden and the Disney area such a MAGICAL place to live. If you’ve been waiting for a home that offers space, flexibility, privacy with a pool, and a fantastic location, THIS IS THE ONE!

2139 Tillman Avenue, Winter Garden

14656 Pylon Court, Winter Garden
$2,300,000
7 Beds ⋅ 7 Baths ⋅ Isles/Lk Hancock Ph Iii SubDv. ⋅ 34787 Zip Code
Welcome to this beautiful lake-view home in the desirable, gated Isles of Lake Hancock community in Horizon West / Winter Garden! This spacious 7-bedroom, 6.5-bathroom home offers approximately 4,634 square feet of living space on an oversized 0.43-acre lot, with beautiful lake views from both the front and back of the property. The first floor features a spacious primary suite with a sitting area and his-and-hers walk-in closets, three additional bedrooms with bathrooms, and a separate office perfect for working from home, and a formal dining area for family meals and entertaining.The split-bedroom floor plan offers added privacy and flexibility. Upstairs, you'll find three more bedrooms, two bathrooms, and a loft area, providing plenty of space for family and guests. The home also offers two separate garage spaces, with one currently enclosed and used as a gym that can be converted back into a garage if desired. Enjoy Florida living with a screened-in pool, summer kitchen, solar panels, and beautiful sunset views over the lake. Residents of this gated community enjoy tennis courts, playground and a private boat ramp. Lake Hancock is a nationally recognized water-skiing destination that hosts world-class tournaments. Located in the sought-after Horizon West / Winter Garden area, the community offers convenient access to Walt Disney World, shopping, dining, upscale golf courses, top-rated schools, and SR-429. With plenty of space, beautiful lake views, and a great location, this home has so much to enjoy. Schedule your private showing today!

14656 Pylon Court, Winter Garden

16773 Broadwater Avenue, Winter Garden
$2,435,000
7 Beds ⋅ 6 Baths ⋅ Waterside On Johns Lake SubDv. ⋅ 34787 Zip Code
Experience the ultimate in luxury lakefront living in this exceptional 7-bedroom Mansfield floor plan, offered for sale for the first time by its original owner. Perfectly positioned along nearly 100 feet of shoreline on the spectacular 2,600-acre Johns Lake, this remarkable residence offers approximately 6,300 heated square feet of thoughtfully designed living space, breathtaking panoramic water views, and a rare walkout basement ideal for multigenerational living. Impressive curb appeal and a welcoming courtyard entrance set the stage for soaring ceilings, expansive living areas, and unforgettable lake views from the moment you enter. The magnificent great room is flooded with natural Florida sunshine, featuring an electric fireplace and sweeping views of Johns Lake. The recently renovated gourmet kitchen is a showpiece, boasting an oversized center island, freestanding natural gas range, and separate full-size refrigerator and freezer. The main level features a luxurious owner's suite, dedicated home office, and additional ensuite bedroom. Upstairs, an expansive bonus room complements three generously sized bedrooms and two full bathrooms, providing exceptional flexibility for family and guests. What truly distinguishes this extraordinary lakefront estate is the enormous walkout basement, offering endless possibilities for a home theater, fitness center, entertainment lounge, game room, or custom bar. A SECOND OWNER'S SUITE provides an incredible opportunity for an in-law retreat, extended family accommodations, or private multigenerational living quarters. Thoughtful planning by the original owners includes future pool connections, natural gas stub-outs for additional coach lighting, preplumbing and gas connections for an outdoor summer kitchen, and numerous additional ceiling fan locations. Additional enhancements include plantation shutters, custom closets, and a whole-home natural gas backup generator. Step outside to an expansive backyard showcasing breathtaking 180-degree panoramic views of Johns Lake. Your private covered boat dock with low-maintenance composite decking and boat lift creates the ultimate waterfront lifestyle, with boating, fishing, watersports, and sunset cruises right from your backyard. Spanning Orange and Lake counties, Johns Lake is renowned for its expansive open waters, scenic shoreline, and exceptional fishing. Located within the gated community of Waterside on Johns Lake, residents enjoy resort-style amenities including a beautiful clubhouse, state-of-the-art fitness center, community swimming pool, and playground. This highly desirable Clermont and Winter Garden corridor offers access to sought-after K–12 schools & Foundation Academy, Montverde Academy, and Windermere Prep School. Ideally situated along Marsh Road, this exceptional location places you minutes from outstanding shopping, dining, and entertainment in both Clermont and Winter Garden. Enjoy convenient access to Walt Disney World, SR 429, SR 408, Florida's Turnpike, and Downtown Orlando. Historic Downtown Winter Garden is just minutes away, offering charming boutiques, acclaimed restaurants, the West Orange Trail, community festivals, and its famous Saturday Farmers Market. Combining extraordinary square footage, a rare walkout basement, dual owner's suites, private boating access, and nearly 100 feet of pristine Johns Lake frontage, this remarkable property delivers an unparalleled opportunity to embrace the Florida lakefront lifestyle.

16773 Broadwater Avenue, Winter Garden

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