Winter Garden Homes with Gated Amenities

Winter Garden Homes with Gated Amenities

Welcome to Winter Garden, Florida—a hidden gem nestled in the heart of Orange County. This picturesque city is renowned for its charming downtown area, vibrant community, and lush landscapes that provide an idyllic backdrop for both relaxation and recreation. With its rich history dating back to the early 1900s, Winter Garden seamlessly blends old-world charm with modern conveniences, making it a perfect place to call home.

One of the standout features of Winter Garden is its exceptional residential offerings, particularly homes with gated amenities. These exclusive properties not only provide a sense of security and privacy but also foster a close-knit community atmosphere. Imagine living in a beautifully designed home surrounded by meticulously landscaped grounds, where neighbors become friends and outdoor gatherings are a regular delight.

Gated communities in Winter Garden often come equipped with a variety of luxurious amenities, including resort-style pools, state-of-the-art fitness centers, tennis courts, and scenic walking trails. Many of these neighborhoods are strategically located near top-rated schools, shopping centers, and recreational parks, ensuring that everything you need is just a stone's throw away.

Moreover, Winter Garden is known for its outdoor activities, with the West Orange Trail winding through the city, offering miles of scenic paths for walking, biking, and jogging. The local farmer’s market, held weekly in the charming downtown area, showcases the best of local produce and artisanal goods, making it a beloved community event.

Whether you’re seeking a serene retreat or a vibrant community lifestyle, Winter Garden's gated homes offer the perfect blend of luxury, comfort, and convenience. Come explore this enchanting city and discover your dream home today!

Newest Winter Garden Homes with Gated Amenities

2004 Lake Roberts Landing Drive, Winter Garden
$640,000
4 Beds ⋅ 3 Baths ⋅ Lake Roberts Landing SubDv. ⋅ 34787 Zip Code
Welcome to 2004 Lake Roberts Landing Drive, an exclusive gated community in the heart of Winter Garden. This spacious single-story home has 4 bedrooms, 2.5 bathrooms, and a beautiful pond view. The split-bedroom floor plan gives everyone their own space. The primary suite sits apart from the secondary bedrooms for added privacy. Generous living and dining areas make it easy to entertain or relax with family. At the heart of the home, the kitchen has a breakfast bar, plenty of counter space, and a pantry. It opens to the family room, so you can cook and still be part of the conversation. The primary suite is a peaceful retreat, with a spacious bedroom, dual vanities, a garden tub, and a separate shower. Step out to the covered lanai and enjoy the views. It's an ideal spot for morning coffee, dinner outdoors, or unwinding at the end of the day. Lake Roberts Landing offers the privacy of a gated neighborhood. It's close to shopping, dining, and entertainment in Winter Garden, with easy access to SR 429. Don't miss this chance to own a lakefront home in one of Winter Garden's most desirable gated communities. Schedule your private showing today.

2004 Lake Roberts Landing Drive, Winter Garden
14501 Grove Resort Avenue Unit 1516, Winter Garden
$283,800
3 Beds ⋅ 2 Baths ⋅ Grove Resort And Spa Hotel SubDv. ⋅ 34787 Zip Code
GREAT NEW LISTING: PRICE $283,800.00. MOTIVATED SELLER. WELCOME TO THE GROVE RESORT & WATERPARK, A CONDO HOTEL LOCATED CLOSE TO DISNEY AND ALL THE ORLANDO ATTRACTIONS. THIS BEAUTIFUL LUXURY FULLY FURNISHED 3 BEDROOM/2 BATHROOM JASMINE DESIGN CONDO HAS GREAT WATER VIEWS FROM THE SCREENED BALCONY ON THE 5TH FLOOR. YOU CAN OWN A BEAUTIFUL VACATION CONDO AT THE GROVE RESORT THAT OFFERS PROFESSIONAL ON SITE PROPERTY MANAGEMENT SERVICES TO OWNERS AND THEIR GUESTS. THE GROVE RESORT HAS MANY AMENITIES INCLUDING: WATERPARK, LAZY RIVER, SWIMMING POOLS, WATER SLIDES, SPA, INDOOR & OUTDOOR DINING, FITNESS CENTER, LAKE AUSTIN FOR FISHING AND PADDLE BOATING, SHOPPING AND MUCH MORE.

14501 Grove Resort Avenue Unit 1516, Winter Garden
14501 Grove Resort Avenue Unit 3618, Winter Garden
$430,000
3 Beds ⋅ 3 Baths ⋅ Grove Resort And Spa Hotel SubDv. ⋅ 34787 Zip Code
WELCOME TO THE GROVE RESORT & WATERPARK, WINTER GARDENS, ORLANDO FLORIDA. THIS BEAUTIFUL FULLY FURNISHED SABLE DESIGN CONDO IS IN AN EXCELLENT LOCATION WITH GREAT VIEWS OF WATER PARK AND MUCH MORE. THIS BEAUTIFUL SABLE DESIGN CONDO IS ON THE 6TH FLOOR WITH 3 LUXURY BEDROOMS AND 3 GREAT BATHROOMS. AND GREAT VIEWS FROM SCREENED BALCONY. YOU CAN OWN THIS BEAUTIFUL VACATION CONDO AT THE GROVE RESORT THAT OFFERS PROFESSIONAL ON SITE PROPERTY MANAGEMENT SERVICES TO ALL OWNERS AND THEIR GUESTS. THE GROVE RESORT HAS MANY AMENITIES INCLUDING BUT NOT LIMITED TO A GREAT WATER PARK, LAZY RIVER, SWIMMING POOLS , WATER SLIDES, SPA, INDOOR & OUTDOOR DINING, FITNESS CENTER, LAKE AUSTION FOR FISHING AND PADDLE BOATING, SHOPPING AND MUCH MORE

14501 Grove Resort Avenue Unit 3618, Winter Garden
13846 Fresh Ivy Street, Winter Garden
$699,000
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 capital contribution fee PLUS six months of HOA dues!** 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
14501 Grove Resort Avenue Unit 3239, Winter Garden
$165,000
2 Beds ⋅ 2 Baths ⋅ Grove Resort And Spa Hotel Condominium SubDv. ⋅ 34787 Zip Code
***Amazing opportunity to own a vacation condo at the beautiful Grove Resort and Water Park in Orlando! Ideal for SNOWBIRDS, you can stay in your unit up to 179 nights per year! Onsite rental management company rents out your unit on your behalf when you are not using it, yet when you stay you have full access to all the wonderful amenities at The Grove Resort! This 2-bedroom, 2-bathroom fully-furnished condo has a full kitchen, full washer and dryer, spacious living room with sleeper sofa, and screened-in balcony, with a pleasant view over the gardens. A short walk takes you to the Springs Pools area, with three heated pools, hot tub, the 24/7 gym, and the Valencia Restaurant. Just a few minutes stroll also takes you to the Surfari Water Park, with heated large pool and lazy river, water slides, splash area, the Flowrider surfing experience, and the Longboard Bar and Grill!! For further entertainment you have the 6000sf Flip Flops games arcade, with 9-hole mini-golf! A free shuttle goes daily to the Disney these parks, right outside the Marketplace convenience store and gift shop! Call now for more details!!***

14501 Grove Resort Avenue Unit 3239, Winter Garden
13055 Sandcastle Drive, Winter Garden
$863,700
3 Beds ⋅ 4 Baths ⋅ Del Webb Oasis SubDv. ⋅ 34787 Zip Code
Step into the Renown, a new construction, single-story home situated within walking distance of the amenity center offering 3 spacious bedrooms, 3 beautifully appointed full bathrooms, a powder room, and an enclosed flex room. The open-concept layout seamlessly connects the gourmet kitchen, café, and gathering room, creating an airy atmosphere. The many windows and sliding glass door leading to the covered lanai bathe the entire space in natural light, elevating the overall feeling of openness. The heart of the home is the chef-inspired kitchen, where soft-close cabinetry with clear glass uppers meets luxurious quartz countertops and a decorative tile backsplash. Thoughtfully designed features like easy-reach corner cabinets, double roll-out trays, and a waste basket drawer make the kitchen as functional as it is beautiful. Whirlpool stainless steel appliances—including double ovens and a built-in natural gas cooktop—ensure you have everything you need for both everyday meals and special occasions. The kitchen flows effortlessly into the café and gathering room, where a sliding glass door leads to the covered lanai, making this home ideal for seamless indoor-outdoor living. Retreat to the luxurious owner’s suite, a serene sanctuary with two spacious walk-in closets and a spa-like en suite bathroom. Dual vanity sinks, a walk-in shower with a built-in bench and rain shower head, an enclosed toilet, and a linen closet complete the tranquil space. For added convenience, one of the walk-in closets connects to the laundry room which is outfitted with built-in cabinetry, a utility sink trimmed in quartz, and a storage closet. The two additional spare bedrooms, each with their own attached bathroom and walk-in closets, along with the open flex room and powder room, provide ample space for family and guests. Designer-curated finishes elevate every corner of this home, including pendant pre-wire and under cabinet lighting in the kitchen, matte black hardware and plumbing fixtures, and 8’ Cheyenne style interior doors. Enjoy the convenience of modern living with a smart thermostat and doorbell, and LED downlighting. Schedule a tour today!

13055 Sandcastle Drive, Winter Garden
16773 Broadwater Avenue, Winter Garden
$2,575,000
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
14204 Creekbed Circle, Winter Garden
$812,000
4 Beds ⋅ 4 Baths ⋅ Bradford Creek SubDv. ⋅ 34787 Zip Code
Virtually Staged. SUPER PREMIUM LOT • CONSERVATION VIEW • NO REAR NEIGHBORS • HUGE FULLY-FENCED YARD • 3-CAR GARAGE • GATED COMMUNITY! Welcome to 14204 Creekbed Circle, a beautiful 4-bedroom, 3.5-bathroom home located in the desirable Bradford Creek community of Winter Garden. Set on an exceptional premium lot, this home offers a peaceful conservation view with no rear neighbors and an expansive, fully fenced backyard, providing wonderful privacy and plenty of outdoor space. Inside, you'll find solid hardwood flooring and tile, creating an elegant and timeless feel throughout the home. The highly sought-after 3-car garage provides generous space for vehicles, storage, or hobbies. For added value and peace of mind, both A/C units were replaced in January 2025. Enjoy the privacy and exclusivity of a gated community while being located in one of Winter Garden's most desirable areas. This property is a standout opportunity. Schedule your private showing and experience everything this exceptional Winter Garden home has to offer!

14204 Creekbed Circle, Winter Garden
15613 Boggy Oak Circle Unit 110A, Winter Garden
$279,000
2 Beds ⋅ 2 Baths ⋅ Tucker Oaks Condo SubDv. ⋅ 34787 Zip Code
OWNER MOTIVATED!!!! MAINTENANCE-FREE LIVING IN DESIRABLE TUCKER OAKS! Welcome home to this beautifully maintained 2-bedroom, 2-bathroom condo with an attached single car garage, ideally located in the sought-after Tucker Oaks community. Situated on a quiet, lightly traveled cul-de-sac-style road with a dog parkconveniently located directly across the street, this home offers comfort, convenience, and an easy Florida lifestyle.This is one of the newer-built models in the community and features an expanded kitchen layout with additional counter space and a convenient eat-in area. The kitchen is equipped with stainless steel appliances, including a French-door refrigerator, dishwasher, microwave, and range, alongwith upgraded counters, sink, and faucet. The appliances are approximately four years old. Additional kitchen conveniences include pull-out/roll-out cabinet shelving and upper and lower cabinet lighting.The spacious family room features a beautiful focal wall with a floating shelf, electric fireplace, and wall-mounted flat-screen TV, creating a warm and inviting space to relax or entertain. Step outside to the larger upper-level balcony, the perfect spot to enjoy your morning coffee or unwind at the end of the day.The second bathroom features a walk-in shower for added convenience. An interior laundry room includes installed shelving for additional storage.The attached garage offers storage shelving, a painted and sealed floor, and convenient attic storage for seasonal items and belongings.Tucker Oaks offers an array of amenities, including a community pool, basketball courts, playground, dog park, and picnic/BBQ area. Enjoy an unbeatable location close to Winter Garden Village, restaurants, shopping, the farmers market, and Central Florida’s world-famous attractions. Witheasy access to the Florida Turnpike, SR 429, SR 408, and Highway 50, getting around Central Florida is quick and convenient.Come enjoy low-maintenance living, wonderful community amenities, and an incredible location—all in one great condo!

15613 Boggy Oak Circle Unit 110A, Winter Garden
1300 Eastern Pecan Place Unit 208, Winter Garden
$298,500
3 Beds ⋅ 2 Baths ⋅ Southern Pines Condo SubDv. ⋅ 34787 Zip Code
BUYER INCENTIVE! Seller offering $5,000 toward buyer closing costs PLUS an additional $1,000 through the preferred lender—for up to $6,000 in buyer benefits with accepted contract, at closing Plus, enjoy a 2-year warranty on NEW kitchen appliances(refrigerator,microwave and dishwasher). Priced under $299,000! Discover this beautifully updated, move-in-ready condo in the GATED Southern Pines community, just 7 minutes from Historic Downtown Winter Garden! This second-floor residence offers convenient first-floor entry with private keyless access and a welcoming coat closet. Upstairs, the bright, open-concept feature newer luxury plank vinyl flooring, abundant natural light, updated lighting and ceiling fans, and a dedicated office alcove with custom built-in shelving. Fresh paint throughout—including walls, ceilings, doors, baseboards, and trim—creates a clean, contemporary feel. The upgraded galley kitchen features neutral cabinetry, granite countertops, a pantry, and BRAND-NEW, NEVER-USED stainless-steel refrigerator, microwave, and dishwasher! Its efficient layout keeps cooking connected to the living areas, while the conveniently located laundry room makes everyday tasks easier. The desirable split-bedroom floor plan continues with luxury plank vinyl flooring and offers privacy for the spacious primary suite, complete with a walk-in closet, ceiling fan and en-suite bath featuring a large walk-in shower and granite-topped vanity. Two additional bedrooms on the opposite side of the common area both with generous walk-in closets and ceiling fans. The second full bath features an extended granite vanity with abundant storage and a tub/shower combination. Both bathrooms showcase BRAND-NEW MOEN faucets and shower/tub fixtures, updated lighting, framed/finished mirrors, and new cabinet hardware. All interior door hardware has also been replaced with lever handles and hinges in updated finish to match all the new fixtures and hardware throughout. Extra storage is a plus in the laundry-room (Washer and dryer are negotiable) and linen closet near the HVAC system, which has received seasonal servicing. Drapes do not convey. Resort-style amenities abound! Southern Pines residents enjoy a pool and spa, fitness center, tennis courts, indoor basketball court, volleyball court, playground, pet park, clubhouse with theater room, billiards room, computer center, BBQ area, and resident car wash station. Gated entry and on-site management add convenience. Enjoy easy access to Publix, Winter Garden Village, the West Orange Trail, Historic Downtown Winter Garden, shopping, dining, entertainment and medical facilities. The Florida Turnpike, SR 429, and I-4 provide convenient connections throughout Central Florida, including Orlando attractions and major employment centers. HOA dues include internet, basic cable, trash service, recreational amenities, and exterior lawn care and exterior maintenance. Enjoy the convenience of condo living, with exterior maintenance and roof replacement handled through the association in accordance with its governing documents and budget. EXTENSIVELY UPDATED. MOVE-IN READY. EXCEPTIONAL VALUE! Brand-new kitchen appliances, a 2-year appliance warranty, resort-style amenities managed professionally and up to $6,000 in buyer benefits make this a fantastic Winter Garden opportunity. Schedule your private showing today!

1300 Eastern Pecan Place Unit 208, Winter Garden
14501 Grove Resort Avenue Unit 2539, Winter Garden
$163,000
2 Beds ⋅ 2 Baths ⋅ Grove Resort And Spa Hotel Condominium 1 SubDv. ⋅ 34787 Zip Code
BEST-PRICED UNIT CURRENTLY AVAILABLE AT THE GROVE RESORT! This 5th-floor Birch residence is located in desirable Tower 2, the newest tower at The Grove and featuring the resort's most updated décor and finishes. Enjoy a peaceful garden view from this fully furnished resort residence just minutes from Walt Disney World. The Grove Resort & Water Park offers an exceptional combination of vacation ownership and resort amenities, including Surfari Water Park, multiple pools, restaurants and bars, fitness center, spa, arcade, Lake Austin activities, market and coffee shop, and on-site resort management. An outstanding opportunity for buyers looking for an entry point into one of Orlando's most established condo-hotel resorts at the best price currently offered. Financial information and ownership details available upon request.

14501 Grove Resort Avenue Unit 2539, Winter Garden
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