Winter Garden Homes with Gated Amenities

Winter Garden Homes with Gated Amenities

Welcome to Winter Garden, Florida – a charming city nestled in the heart of Orange County. Known for its vibrant community spirit and picturesque landscapes, Winter Garden offers a perfect blend of small-town charm and modern conveniences. With its historic downtown area, lined with quaint shops, delightful restaurants, and lush parks, residents enjoy a lively atmosphere filled with seasonal events and cultural activities.

Winter Garden is not just a beautiful place to live; it also boasts a variety of housing options, including homes with gated amenities that provide an added layer of security and exclusivity. These gated communities are designed to enhance your lifestyle, offering peace of mind while fostering a sense of belonging. Imagine living in a serene neighborhood where children can play safely, and neighbors become friends.

Many of these exquisite homes feature luxurious finishes, spacious layouts, and access to resort-style amenities such as swimming pools, fitness centers, and scenic walking trails. Whether you’re looking for a cozy family home or a stunning estate, Winter Garden's gated communities cater to diverse tastes and preferences.

With its proximity to major highways, residents can easily access the attractions of Orlando, including theme parks, shopping, and entertainment, while still enjoying the tranquility of suburban living. Embrace the best of both worlds in Winter Garden, where your dream home awaits in a community that feels like family. Explore the possibilities today and discover why Winter Garden is the ideal place to call home!

Newest Winter Garden Homes with Gated Amenities

$525,000
3 Beds ⋅ 2 Baths ⋅ Lift Station/Cobblestone/Winte SubDv. ⋅ 34787 Zip Code
Bright, open living meets a polished, move-in-ready feel in Winter Garden. A flowing tile-floor plan creates an effortless backdrop for daily living and entertaining, anchored by a standout kitchen with crisp white cabinetry, stainless steel appliances, dramatic stone countertops and backsplash, recessed lighting, and an oversized waterfall island with seating. The generous primary retreat offers a large walk-in closet and an en-suite bath with dual sinks, a soaking tub, and a separate tiled shower. Well-proportioned secondary bedrooms offer versatile space, while the interior laundry room and two-car garage add everyday convenience. Sliding glass doors open to a covered, screened lanai, an inviting spot for morning coffee, outdoor dining, or relaxing with views of the expansive backyard. The home’s welcoming curb appeal is enhanced by an arched entry, shutters, and established landscaping. Enjoy the best of Winter Garden living, with Historic Downtown Winter Garden’s boutiques, dining, farmers market, and community events, plus the beloved West Orange Trail for walking, biking, and exploring.

356 Black Springs Lane, Winter Garden
$219,000
3 Beds ⋅ 3 Baths ⋅ Grove Residence & Spa Hotel Condo Li SubDv. ⋅ 34787 Zip Code
**Spacious 3-bedroom, 3-bathroom fully-furnished condo located on the fourth floor of the beautiful Grove Resort and Water Park! This condo has a full kitchen, full washer and dryer, large primary bedroom with sitting area, large primary bathroom with dual sinks and separate shower and tub, a second bedroom with its own ensuite bathroom, and a third bedroom and bathroom. The screened-in balcony overlooks the central fountain area, so the location is only a short stroll away from any amenities! You have the Surfari water park with a large heated pool, lazy river, water slides, splash area, and the Flowrider surfing experience! The Longboard Bar and Grill is located inside the water park for delicious meals, snacks and drinks! Or visit the Springs Pools area which has three further pools, and the relaxing hot tub! Located next to the Valencia Restaurant, the outdoor bar is also located there, and the 24/7 gym! Take a stroll down to Lake Austin and try your hand at fishing, kayaking, or paddle a swan boat!! For indoor fun visit Flip Flops, the 6000 sf games arcade with glow-in-the-dark mini golf!! For your convenience for food, gifts and sundries, we have the Marketplace, located at the Front Desk area. A free daily shuttle to the Disney parks is also provided for owners and guests. Enjoy ownership of a vacation condo, while having the onsite management company place bookings in your unit while you are not there! It is a completely hands-free experience! Call now for more details!!**

14501 Grove Resort Avenue Unit 3401, Winter Garden
$265,000
2 Beds ⋅ 2 Baths ⋅ Southern Pines Condo SubDv. ⋅ 34787 Zip Code
Welcome to this beautifully maintained 2-bedroom, 2-bath first-floor unit with a 1-car garage, located in the highly desirable gated community of Southern Pines in the heart of Winter Garden. Offering the perfect combination of comfort, convenience, and resort-style living, this home is ideal for first-time buyers, downsizers, investors, or anyone seeking a low-maintenance lifestyle. The thoughtfully designed floor plan features spacious living areas, two generously sized bedrooms, and two full bathrooms, all conveniently situated on the first floor for easy access. Enjoy the added value of water, internet, and cable included in the monthly Condo fee, making everyday living both simple and budget-friendly. Southern Pines is known for its outstanding amenities, offering residents a true resort-style experience. Spend your days relaxing by the sparkling pool and hot tub, entertain friends at the BBQ grills and outdoor kitchen, or enjoy the beautifully appointed clubhouse featuring a movie theater, business center, and billiards room. Stay active with the fully equipped fitness center, indoor basketball and racquetball courts, tennis courts, beach volleyball court, and a covered outdoor playground. Additional conveniences include a car wash station and beautifully maintained grounds throughout the community. Ideally located just minutes from Historic Downtown Winter Garden, Winter Garden Village, major highways including SR-429 and the Florida Turnpike, shopping, dining, entertainment, and world-renowned theme parks, this condo offers an unbeatable location with exceptional amenities. Don't miss your opportunity to own a piece of one of Central Florida's most sought-after communities!

405 Southern Pecan Circle Unit 108, Winter Garden
$610,000
4 Beds ⋅ 3 Baths ⋅ Lakeview Preserve Rep SubDv. ⋅ 34787 Zip Code
Space, style, and a true lake-community lifestyle come together in this thoughtfully designed home in the gated community of Lakeview Preserve. With a flexible floor plan, generous living spaces, and room to grow both inside and out, this home offers the perfect blend of comfort, functionality, and Florida living. The open-concept layout is designed for both entertaining and everyday living. At the heart of the home, the kitchen features white shaker cabinetry, quartz countertops, stainless steel appliances, a walk-in pantry, and an oversized island with seating for four. It flows seamlessly into the dining area and spacious living room, creating a welcoming space for everything from weeknight dinners to holiday gatherings. French doors off the foyer lead to a dedicated office, providing flexibility for working from home, a playroom, hobby space, or a quiet retreat. Tucked away on the first floor, the private primary suite features dual vanities, a soaking tub, glass-enclosed shower, and a generous walk-in closet. Upstairs, the expansive bonus room offers endless possibilities as a media room, game room, playroom, or second living area. The additional bedrooms provide comfortable accommodations for family and guests, giving everyone space to spread out. Step outside to the covered brick-paver lanai overlooking the fully fenced backyard, where there's plenty of room for outdoor entertaining, pets, play, gardening, or even a future pool. Whether you're enjoying a quiet morning or hosting friends for a weekend barbecue, the outdoor space is ready to fit your lifestyle. Life in Lakeview Preserve is about more than just the home. Set along the shores of Johns Lake, this gated community embraces an active Florida lifestyle with amenities designed for all ages. Residents enjoy a resort-style pool, splash pad, fitness center, clubhouse and community cabana, playground, community dock, and kayak launch with direct access to Johns Lake for boating, fishing, and paddling. Conservation areas woven throughout the neighborhood enhance the natural beauty, creating a peaceful setting while keeping you close to everything Winter Garden has to offer. Conveniently located just minutes from SR 429, Winter Garden Village, historic Downtown Winter Garden, shopping, dining, parks, and everyday conveniences, this home offers the ideal balance of space, convenience, and community. Whether you're looking for room to grow, space to entertain, or a neighborhood built around an active Florida lifestyle, this home offers the flexibility to fit your lifestyle while creating lasting memories.

3247 Buoy Circle, Winter Garden
$335,000
3 Beds ⋅ 3 Baths ⋅ Tucker Oaks SubDv. ⋅ 34787 Zip Code
Virtually Staged. Welcome to this beautifully maintained end-unit townhome located in the desirable gated community of Tucker Oaks in Winter Garden, offering extra privacy, abundant natural light, and a premium pond-view lot with additional backyard space. Conveniently situated right next to the community amenities, this home combines comfort, style, and an exceptional location. Step inside to an inviting open-concept floor plan featuring a spacious living room, dining area, and kitchen that flow seamlessly together, making it perfect for both everyday living and entertaining. The kitchen is beautifully appointed with tall cabinetry, granite countertops, stainless steel appliances, and a large walk-in pantry, while a versatile flex room offers the perfect space for a home office, formal dining room, playroom, or additional living area. A beautifully renovated half bathroom and an indoor laundry room add convenience to the first floor. Upstairs, you'll find like-new carpet (2020) throughout, two spacious guest bedrooms, a full guest bathroom, and a relaxing primary suite featuring an elegant tray ceiling and tranquil pond views. The en-suite bathroom offers a double-sink vanity, a garden tub/shower combination, and a generous walk-in closet. Additional features include a new air conditioning system (2026), new roof (2024), new water heater (2024) and a large garage with tall ceilings, providing excellent storage space. Enjoy peaceful mornings overlooking the pond and all the benefits of living in a gated community with nearby amenities including a pool and dog park. This move-in-ready home offers the perfect combination of thoughtful upgrades, functional living space, and an unbeatable location.

1668 Scarlet Oak Loop Unit C, Winter Garden
$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
$465,000
3 Beds ⋅ 3 Baths ⋅ Emerald Ridge SubDv. ⋅ 34787 Zip Code
*Walkthrough Video Available* Welcome to the gated Emerald Ridge neighborhood that is conveniently located near the 429, Turnpike, shopping and restaurants in Winter Garden, Horizon West and Windermere as well as the charming downtown Winter Garden Plant Street and all of the local activities it brings. Cool off in the COMMUNITY POOL and enjoy staying active on the sidewalks that run throughout the neighborhood. This home has an OPEN FLOOR PLAN that greets you as soon as you enter. The spacious living room has nice natural lighting and opens to the eat-in kitchen which was recently remodeled. You’ll find NEW CABINETRY with soft-close doors, a TILE BACKSPLASH and STAINLESS STEEL appliances. The WALK-IN PANTRY is a dream as it gives storage space for kitchen wares and laundry needs. Sliding doors open to the SCREENED PATIO so you can enjoy the evening breeze. There’s a SPACIOUS LOFT upstairs which makes for a fantastic 2nd living room, home office, play space, or home gym. The primary suite in this model is extra large giving room for a sitting area! The WALK-IN CLOSET offers plenty of space to keep your wardrobe organized and the en-suite bathroom has a garden tub and separate shower. The secondary bedrooms share a hall bathroom. The ROOF, AC, AND WATER HEATER WERE REPLACED IN 2018. Additional upgrades include CROWN MOLDING and canned lighting throughout the home.

1830 Morning Sky Drive, Winter Garden
$599,000
5 Beds ⋅ 4 Baths ⋅ Johns Landing Ph 01 44/47 SubDv. ⋅ 34787 Zip Code
Virtually Staged. BRAND NEW ROOF! This five-bedroom, three-and-a-half-bathroom residence sits in a gated community with a new roof and architectural shingles, offering security and peace of mind. The property combines thoughtful interior finishes with direct access to some of the area's most desirable outdoor recreation opportunities. Inside, the kitchen features stainless steel appliances and a custom tile backsplash above stone countertops, with a breakfast nook for casual dining. The primary suite includes a picture window and rich wood flooring, complemented by crown molding throughout the residence. The great room flows across ceramic tile and polished wood surfaces, while the formal dining room showcases gleaming wood floors. An upstairs loft with natural wood planks provides flexible space for an office, playroom, or media area. The laundry room features ceramic tile for easy maintenance and durability. A smart thermostat manages climate control efficiently throughout all living areas. The covered front porch creates an inviting entrance, and mature landscaping frames the property with established trees and plantings that provide natural privacy and curb appeal. The location offers exceptional convenience and recreation. You're minutes from Downtown Winter Garden, with easy connectivity to the Florida Turnpike for broader travel throughout Central Florida. The West Orange Trail is nearby for outdoor enthusiasts seeking biking and nearby paths, and the community boat ramp provides direct waterfront entry to John's Lake for boating and fishing. The Oakland Nature Preserve is close by, offering natural spaces to explore with nearby trails and wildlife viewing opportunities. Whether you're seeking waterfront recreation, trail connectivity, or proximity to local commerce and dining, this address delivers on multiple fronts. Schedule a showing today to experience this property and its neighborhood firsthand.

706 Strihal Loop, 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
$900,000
5 Beds ⋅ 4 Baths ⋅ Lake Forest Sec 10a SubDv. ⋅ 34787 Zip Code
Welcome to this beautifully designed 5-bedroom, 4-bath home located in a gated Winter Garden community, offering an exceptional blend of elegant finishes, functional living spaces, and resort-style outdoor living. With soaring ceilings and an inviting open entry, this home is filled with architectural details including crown molding, coffered and tray ceilings that add character throughout. Designed for both everyday living and entertaining, the thoughtfully crafted floor plan offers formal living and dining areas while maintaining an open flow between the kitchen and family room. Tile flooring extends through the main living areas and luxury vinyl in the primary suite and entire upstairs, providing both style and durability. The spacious kitchen serves as the heart of the home with granite countertops, abundant cabinetry, generous counter space, bar seating, a separate dinette, and seamless views into the family room. Expansive pocket sliding glass doors create a true indoor-outdoor living experience, opening the family room to the covered lanai and pool area—perfect for entertaining family and friends. The first-floor primary suite is a private retreat featuring abundant natural light, direct access to the lanai, dual walk-in closets, separate vanities, a walk-in shower, and a relaxing soaking tub. A dedicated office with built-in shelving and closet space provides an ideal work-from-home setup. Two additional bedrooms and bathrooms are also located downstairs, including a private en-suite with direct access to the pool. Upstairs offers exceptional flexibility with a spacious loft that can serve as a second living area, game room, or playroom, along with a fourth bedroom and full bath. A fifth bedroom is currently configured as a media room with surround sound and projector hookups, making it ready for movie nights or easily converted back to a bedroom. Step outside to your own backyard retreat featuring a sparkling pool with a natural rock waterfall, a unique swim-up table, and a spacious covered lanai. The fully fenced backyard provides both privacy and room to relax, play, or entertain. Additional highlights include a three-car garage and an ideal location just minutes from Winter Garden Village, offering shopping, grocery stores, restaurants, and healthcare. With convenient access to SR-429 and Historic Downtown Winter Garden, this home combines the comfort of a gated community with easy access to everything Central Florida has to offer.

13624 Larsen Lane, Winter Garden
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