Winter Garden Homes with Gated Community - Guard Community Features

Winter Garden Homes with Gated Community - Guard Community Features

Welcome to Winter Garden, Florida, a charming city nestled in the heart of Orange County that beautifully blends small-town warmth with modern conveniences. Known for its picturesque landscapes, historic downtown, and vibrant community spirit, Winter Garden offers an ideal setting for families, retirees, and everyone in between. With its proximity to Orlando, residents enjoy easy access to world-renowned attractions, shopping, and dining, while still being able to retreat to the serene ambiance of their hometown.

One of the standout features of Winter Garden is its selection of gated communities, offering an added layer of security and exclusivity. These guard-gated neighborhoods provide peace of mind for homeowners, allowing you to relax and enjoy the beautiful surroundings without worry. Many of these communities boast stunning architecture, meticulously landscaped grounds, and a variety of amenities designed to enhance your lifestyle.

Imagine coming home to a beautifully designed residence, where neighbors become friends and the community thrives on connection. In Winter Garden’s gated communities, you’ll find luxurious homes equipped with modern finishes, spacious floor plans, and outdoor spaces perfect for entertaining. Residents can enjoy amenities such as clubhouses, swimming pools, fitness centers, and walking trails, all within a secure environment.

Living in a gated community in Winter Garden means embracing a lifestyle marked by tranquility, community engagement, and unparalleled access to the natural beauty of Florida. Whether you’re sipping coffee on your porch or taking a leisurely stroll through the neighborhood, Winter Garden invites you to experience the best of Florida living. Welcome home!

Newest Winter Garden Homes with Gated Community - Guard Community Features

$219,000
3 Beds ⋅ 2 Baths ⋅ Grove Residence & Spa Hotel Condo Ii SubDv. ⋅ 34787 Zip Code
**Beautiful 3-bedroom/2-bathroom Jasmine floorplan available for sale at The Grove Resort and Water Park! This first floor apartment is fully-furnished and has everything you need for a wonderful vacation condo! This spacious unit has 14-foot ceilings in the main living space, giving a light, airy feel, and opens to an enclosed balcony where you can enjoy views of gardens and pond. Full kitchen has everything you need for cooking breakfasts, to family dinners, with a full washer and dryer in a room just off the kitchen. The living room also has a sleeper sofa for extra guests if needed. A short stroll brings you to either the central front desk area where you will find The Marketplace, the well-stocked convenience store, and the gift shop and concierge desk, or to the Springs Pools area where you can choose from three beautiful pools and the hot tub. The Valencia Restaurant, with additional outside seating, is open for breakfast, lunch, and dinner, 7 days a week, and is next to the 24/7 gym. Take a walk down to Lake Austin and try some fishing, or paddle a swan boat! From there you can visit the Surfari water park with its large pool, lazy river, water slides, and splash area! Try out the Flowrider surfing experience, or just watch while enjoying food and drinks from the Longboard Bar and Grill! Flip Flops is the 6000sf games arcade with glow-in-the-dark mini golf, so don't miss that! Free daily shuttles to the Disney parks are available for all owners and guests! This truly is a great place to own a vacation condo while the onsite management company rent out your unit when you are not there! Call for more details!!**

14501 Grove Resort Avenue Unit 2119, Winter Garden
$179,000
2 Beds ⋅ 2 Baths ⋅ Grove Residence & Spa Hotel Condo 3 SubDv. ⋅ 34787 Zip Code
**Beautiful Palm model 2-bedroom/2-bathroom condo for sale at The Grove Resort and Water Park! This fully-furnished unit has a lovely view over the central fountain and is bright and airy. This floorplan has the desirable two double beds in the second bedroom, providing extra sleeping accommodation for owners and guests. A sleeper sofa in the living room gives extra sleeping space if required. A full kitchen provides all you need for cooking a quick breakfast, or family dinner, and a laundry room is also conveniently situated just off the kitchen. The dining area and living room give plenty of seating for guests, or enjoy a quiet coffee out on the screened balcony. The unit is central to the resort, so all amenities are just a few minutes stroll away. You can enjoy the Surfari water park with its large pool, lazy river, water slides, and splash zone! The Longboard Bar and Grill are also inside the water park, along with the Flowrider surfing experience!! Don't forget to visit Flip Flops, the 6000sf games arcade, with glow-in-the-dark mini golf, or go down to the Springs Pools where you have your choice of three further pools, or relax in the hot tub! You can enjoy a meal at the Valencia Restaurant, or at the outdoor bar, or walk down to Lake Austin and try your hand at fishing, kayaking, or paddling a swan boat! The Front Desk is where you will find the Marketplace convenience store and gift shop, and the concierge for all your theme park tickets or excursions! The Grove Resort also provides FREE daily transportation to the Disney theme parks. Don't miss out on owning a wonderful vacation condo at The Grove, where you can enjoy your vacations, then let the onsite management company rent out your unit for income when you are not using it. Call for more details!!**

14501 Grove Resort Avenue Unit 3406, Winter Garden
$295,000
2 Beds ⋅ 2 Baths ⋅ Grove Residence & Spa Hotel Condo Ii SubDv. ⋅ 34787 Zip Code
NEWEST TOWER | TOP FLOOR | FOUNTAIN VIEW This is resort-style living at its absolute finest. This Fountain View Palm Unit in Tower 2 — the newest and most beautifully appointed tower in the community — offers the perfect blend of luxury, lifestyle, and income-generating opportunity. Step into a world-class destination that rivals the finest resorts anywhere in the world. With stunning superior views, the most updated and designer-curated décor in the entire property, and access to an unparalleled collection of amenities, this is more than a home — it's a five-star experience every single day. When you're not enjoying it yourself, let your investment work for you. This property sits within a prestigious hotel-managed rental program, meaning a professional, on-site operator handles everything — from bookings and guest services to housekeeping and maintenance. Completely hands-off ownership with income flowing in while the resort does all the heavy lifting. Owners enjoy access to resort amenities including pools, restaurants, spa, fitness facilities, and more — all maintained to the highest hospitality standards. Whether you're seeking a personal escape, a vacation retreat, or a smart investment vehicle, this unit checks every box. Newest tower. Most updated finishes. Superior views. World-class amenities. Professionally managed income potential. Financials available. Opportunities like this are rare — and they don't stay on the market long.

14501 Grove Resort Avenue Unit 2703, Winter Garden
$190,000
2 Beds ⋅ 2 Baths ⋅ Grove Resort SubDv. ⋅ 34787 Zip Code
TOWER 3 LOCATION CLOSEST TO THE WATERPARK! Exceptional opportunity to own at The Grove Resort & Water Park, one of Central Florida’s premier vacation ownership destinations just minutes from Walt Disney World. This condo is a beautifully furnished Birch Plan residence offering a comfortable, turnkey layout designed for personal enjoyment and income-producing vacation rental use. The open living area, full kitchen, private bedrooms, and resort-style finishes create an inviting retreat for Owners and guests alike. The Grove offers an impressive amenity package including a water park, multiple pools, lazy river, restaurants, bars, spa, fitness center, lake activities, arcade, onsite market, and full-service onsite management. Owners may enjoy generous personal use while the onsite management team handles guest services, reservations, maintenance, and day-to-day rental operations. With its strong location, established resort setting, and continued appeal to Orlando visitors, this Birch Plan condo is a compelling choice for Buyers seeking lifestyle, convenience, and long-term Central Florida vacation ownership.

14501 Grove Resort Avenue Unit 3231, Winter Garden
$899,000
5 Beds ⋅ 4 Baths ⋅ Oxford Chase SubDv. ⋅ 34787 Zip Code
Virtually Staged. Welcome to 14779 McClane Road! Set behind the gates of Oxford Chase, this one of a kind Mattamy home stands apart from anything else in the community. Five bedrooms, four baths, and 3,118 square feet of genuinely upgraded living on a lot that simply cannot be replicated. At the heart of it is a custom designed kitchen any chef would love to call their own. A dramatic waterfall edge stone island seats four beneath designer glass pendants, surrounded by crisp white cabinetry, a deep stainless farmhouse apron sink, a gas cooktop beneath a vented stainless chimney hood, and a full stainless double wall oven. It opens directly into the great room and flows to a formal dining room crowned by a tray ceiling, bay window, and cascading crystal chandelier. Large stone look tile runs continuously through every common area with no transitions and no compromises. The attention to detail carries throughout. Every bathroom features tile taken floor to ceiling in the shower surrounds, accented by a custom glass mosaic inlay band. The first floor primary offers privacy and generous proportions, while a main floor laundry room adds a deep storage closet, the kind of everyday storage that makes a home genuinely functional. Upstairs is where this floor plan gets extremely special. A spacious loft paired with its own full bathroom creates a genuine second living quarters, not a bonus room with a powder bath down the hall. Aging parents get real independence. Young adults returning home get privacy and dignity. An au pair, a long term guest, or a live in caregiver has a complete suite of their own. It is the kind of true multi generational layout families search for and rarely find. An oversized 3 car garage with an extra deep bay handles the vehicles, the workshop, and everything in between. Step outside and the setting speaks for itself. An oversized covered lanai opens onto a wide, open lawn with no rear neighbors and no homes across the way. The protected retention area means that openness is permanent, not a temporary view waiting to be built out. The yard is already pre wired for a pool, so your private resort is ready whenever you are. A walking trail sits just a short stroll from your door. And nearly every night, you can finish dinner on the lanai and watch Disney's fireworks light up the sky, visible from multiple vantage points throughout the home. The location may be the quietest luxury of all. SunRidge Elementary and SunRidge Middle are an easy walk from your front door. AdventHealth Winter Garden sits roughly five minutes away. Minutes in the other direction, the new $31 million Tucker Ranch wellness complex is bringing a teaching farm, botanical gardens, retreat center, and fitness trail system, joining the existing 200 acre nature preserve on Johns Lake with its kayak launch and miles of trails. Plant Street's restaurants and award winning Farmers Market, Winter Garden Village, and quick access to the 429 are all close at hand, with Orlando International Airport about 30 minutes out. Homes in Oxford Chase rarely come available, and lots like this one almost never do. Seller offering a $1,000 paint allowance and a $500 cleaning allowance to buyer at closing. Schedule your private showing today!

14779 Mcclane Road, Winter Garden
$260,000
3 Beds ⋅ 2 Baths ⋅ Grove Resort And Spa Hotel Condominium SubDv. ⋅ 34787 Zip Code
** WOW** A rare opportunity to purchase a 7th (top) floor condo at the beautiful Grove Resort and Water Park! This 3-bedroom, 2-bathroom, with sleeper sofa, comes fully furnished and ready to go! Onsite management does all the work for you by obtaining bookings through major websites and travel companies, and whenever you want to stay just let them know and you can stay in your unit for up to 179 nights per year. Everything you need is in the unit, full kitchen, washer and dryer, dishes, linens, TV's in all rooms, screened-in balcony, and gorgeous view over the pond and Lake Austin! The Grove Resort has three pools located at The Springs Pools area, where the large hot tub is also situated! Nearby is the full service Valencia restaurant, and the 24/7 gym. A short walk down to Lake Austin brings you to a fishing dock, and you can also rent a swan paddle boat, or kayak!! The Surfari Water Park is a must for owners and guests! A large pool is central to the amenity, and there is a lazy river, water slides, a splash zone, the Flowrider surfing experience, and you can enjoy a meal or beverage at the Longboard Bar and Grill! For added fun pay a visit to Flip Flops games arcade which has over 6000 sf of games and a black light mini golf course!! If you need snacks or quick essentials, the Marketplace has food, drinks, Starbucks, and gifts!! The concierge located at the front desk area sells all park tickets and can arrange transportation to all the theme parks!!! The Grove Resort is a Disney Good Neighbor Hotel, so transportation is FREE every day to the Disney theme parks also!! Don't miss this one!!****

14501 Grove Resort Avenue Unit 1728, Winter Garden
$230,000
3 Beds ⋅ 2 Baths ⋅ The Grove Resort SubDv. ⋅ 34787 Zip Code
The Jasmine model is the MOST SPACIOUS condo in the sought after Grove Resort & Water Park. The condo 2233 is FULLY FURNISHED, DECORATED and equipped with everything you need and is located in NEWEST STERLING TOWER-II. Featuring an open concept living & dining area with a screened balcony overlooking lush gardens. The modern kitchen has quartz countertops, stainless steel appliances, and attached laundry room with full size washer and dryer. YOUR PERFECT VACATION HOME IS AT THE GROVE RESORT where you will enjoy privacy and convenience, including a concierge, multiple bars, restaurant, convenience store, spa, elaborate game room, stunning water park oasis, breathtaking 22-acre activity lake all professionally managed with turnkey hotel rental programs to help offset costs. The property is JUST 6 MILES FROM WALT DISNEY WORLD and close to all Central Florida’s attractions, shops, restaurants and major highways.

14501 Grove Resort Avenue Unit 2233, Winter Garden
$215,000
2 Beds ⋅ 2 Baths ⋅ Grove Residence & Spa Hotel Condo 3 SubDv. ⋅ 34787 Zip Code
Experience the ultimate vacation lifestyle and investment opportunity at Grove Resort & Spa Orlando! This beautifully appointed 2-bedroom, 2-bath condo-hotel offers approximately 1,265 square feet of thoughtfully designed living space with an open-concept layout, stone countertops, stainless steel appliances, walk-in closet, in-unit laundry, private balcony, and elevator access. Fully furnished and turnkey, this residence is ideal as a personal vacation retreat or income-producing property within one of Central Florida's premier resort destinations. Owners and guests enjoy world-class amenities including Surfari Water Park with FlowRider® surf simulator, lazy river, multiple resort pools, private cabanas, waterslides, fitness center, full-service spa, lake activities on Lake Austin, on-site restaurants and bars, arcade, concierge services, 24-hour gated security, and complimentary transportation to Walt Disney World®. Located just minutes from Disney, Flamingo Crossings, shopping, dining, golf, and Orlando's world-famous attractions, this exceptional resort property delivers the perfect blend of luxury, convenience, and unforgettable Florida living.

14501 Grove Resort Avenue Unit 3303, Winter Garden
$287,000
3 Beds ⋅ 2 Baths ⋅ Southern Pines Condo SubDv. ⋅ 34787 Zip Code
Beautiful 3-bedroom, 2-bath condominium located in the highly desirable gated community of Southern Pines in Winter Garden. This spacious unit offers 1,453 square feet of living space with an open floor plan, abundant natural light, and a comfortable layout perfect for both homeowners and investors. Residents enjoy resort-style amenities including a community pool, heated spa, fully equipped fitness center, indoor basketball court, tennis and racquetball courts, sand volleyball court, movie theater, game room, business center, and playground. The community is conveniently located near major highways, shopping, dining, entertainment, and historic downtown Winter Garden. Experience maintenance-free living in one of Central Florida's most sought-after communities. Schedule your private showing today.

1300 Eastern Pecan Place Unit 208, Winter Garden
$725,000
4 Beds ⋅ 4 Baths ⋅ Lakeview Preserve SubDv. ⋅ 34787 Zip Code
Experience elevated Florida living in this beautifully upgraded Lakeview Preserve home, where luxury, efficiency, and low-maintenance comfort come together seamlessly. Featuring a fully owned solar energy system complete with dedicated NEMA 14-50R for your EV, this thoughtfully enhanced residence offers exceptional value with no solar lease or financing to assume. Inside, an open-concept design welcomes you with upgraded flooring, elegant tray ceilings, custom feature walls, and abundant natural light. The spacious living area is highlighted by a stylish electric fireplace, creating a warm and inviting gathering space. The gourmet kitchen is designed for both everyday living and entertaining, featuring luxury stainless steel appliances, ample cabinetry, and seamless flow into the dining and family rooms. The private owner’s suite provides a relaxing retreat with a well-appointed ensuite bath, while the versatile floor plan offers flexibility for growing families, multi-generational living, remote work, or visiting guests. Step outside to your own backyard oasis featuring premium artificial turf for year-round beauty without the upkeep. A dedicated area is perfectly manicured for putt-putt, bocce, corn hole and other outdoor games while powered/motorized awnings and a lanai sunshade create the perfect setting for outdoor dining, entertaining, or relaxing evenings. Permanent exterior accent lighting adds curb appeal and convenience throughout the year. Additional highlights include an extended two-car garage, luxury appliance package, and numerous owner-selected upgrades throughout. Residents of Lakeview Preserve enjoy resort-style amenities including a community pool and cabana, splash pad, fitness center, playground, walking trails, and access to Johns Lake for kayaking, canoeing, and fishing. Conveniently located just minutes from Downtown Winter Garden, shopping, dining, top-rated schools, and SR-429, this home offers the perfect blend of tranquility and accessibility. Rarely does a home combine energy efficiency, premium upgrades, and an exceptional lifestyle in one of Winter Garden’s most desirable communities. Schedule your private showing today.

3447 Current, Winter Garden
$174,999
2 Beds ⋅ 2 Baths ⋅ The Grove Resort And Spa SubDv. ⋅ 34787 Zip Code
Experience the ultimate blend of vacation luxury and smart investing with this stunning 7th-floor condo at The Grove Resort and Spa (Unit 1726). This fully furnished 2-bedroom, 2-bathroom property offers an open, spacious layout designed for comfort, culminating in a private, screened-in balcony featuring serene water views. Whether you are looking for a magical vacation home for your family or a high-performing addition to your real estate portfolio, this turnkey unit offers the unique advantage of an on-site rental program to maximize passive income when you are away. Perfectly situated just minutes from Walt Disney World and other premier Central Florida attractions, the resort provides complimentary shuttle services alongside proximity to world-class dining, shopping, and entertainment. Owners and guests enjoy full access to premium, action-packed amenities, including the expansive Surfari Water Park—complete with a lazy river, dual water slides, and a FlowRider® surf simulator—as well as the tranquil Springs pools, a state-of-the-art fitness center, a full-service spa, glow-in-the-dark mini-golf, and multiple on-site restaurants and bars. Don't miss this exceptional opportunity to own a piece of Orlando's booming hospitality and real estate market!

14501 Grove Resort Avenue Unit 1726, Winter Garden
$699,000
2 Beds ⋅ 2 Baths ⋅ Del Webb Oasis Phase 2 SubDv. ⋅ 34787 Zip Code
Welcome to this ELEGANTLY UPGRADED and nearly new 2-bedroom, 2-bath residence in the highly sought-after Del Webb Oasis of Winter Garden, a GUARD-GATED 55+ community where resort-style living meets everyday sophistication. Perfectly situated on one of ONLY TWO PREMIUM HOMESITES of its kind within the community, this exceptional property enjoys a truly rare distinction: an EXCLUSIVE SIDE EASEMENT that creates exceptional privacy, expanded green space, and a level of openness rarely found in community living, with no immediate neighbor on one side and convenient proximity to the clubhouse area. From the moment you arrive, the home impresses with its REFINED CURB APPEAL, lush landscaping, and a spacious 2-car garage enhanced with CUSTOM STORAGE SOLUTIONS. Inside, a bright OPEN-CONCEPT LAYOUT welcomes you with abundant natural light and meticulous attention to detail throughout every space. The Kitchen is a TRUE SHOWPIECE, equipped with premium stainless steel appliances, a GAS COOKTOP, BUILT-IN OVEN, a CUSTOM BUILT-IN PANTRY WITH PULL-OUT DRAWERS, generous cabinetry, and stone countertops, all seamlessly flowing into the living and dining areas. The Living Room has been elevated with an INTEGRATED SURROUND SOUND SYSTEM, creating the perfect setting for daily enjoyment and entertaining. The Primary Suite is a private retreat featuring a CUSTOM-DESIGNED WALK-IN CLOSET SYSTEM and a well-appointed en-suite bath with dual vanities, generous storage, and a walk-in shower. An additional SECONDARY BEDROOM provides comfortable accommodations for family or guests, while the DEDICATED DEN, enhanced with UPGRADED HIGH BASEBOARDS and RECESSED LIGHTING, offers the flexibility of a home office, hobby room, or formal sitting area. CUSTOM CLOSET SYSTEMS throughout ensure every space is as functional as it is beautiful. Step outside to where this property truly STANDS APART. The expansive SCREENED-IN LANAI opens to an EXTENDED OUTDOOR DECK and a fully appointed BUILT-IN OUTDOOR KITCHEN (BBQ Area), all framed by CUSTOM OUTDOOR LIGHTING, creating an exceptional outdoor retreat designed for year-round Florida living. Additional highlights include a WHOLE-HOME WATER FILTRATION AND SOFTENER SYSTEM, FRESH INTERIOR PAINT throughout, and additional RECESSED LIGHTING both inside and outside that elevates the home's ambiance day and night. Residents of Del Webb Oasis enjoy RESORT-STYLE AMENITIES, including a 12,000 SF clubhouse with coffee bar, lounge, and wine lockers, a sparkling pool, state-of-the-art fitness center, tennis courts, and a vibrant social calendar, along with included cable and internet, fostering the active and connected lifestyle that Del Webb is famous for. IDEALLY LOCATED in Winter Garden, you are just minutes from the charm of HISTORIC DOWNTOWN WINTER GARDEN, known for boutique shops, dining, and a weekly farmers market. Enjoy outdoor recreation along the WEST ORANGE TRAIL, or take a short drive to WORLD-CLASS ATTRACTIONS including Walt Disney World Resort and Universal Studios. Convenient access to FL-429 and major roadways makes it easy to enjoy the very best of Central Florida. This exceptional residence offers a RARE OPPORTUNITY to enjoy elevated, low-maintenance living on one of the community's most coveted homesites, where every upgrade has been thoughtfully chosen and every detail meticulously executed. Homes of this caliber and setting are a TRUE RARITY in Del Webb Oasis. Now is the time, don't miss your chance to call this home.

15139 Canopy Cover Drive, Winter Garden
Start Your Search