Winter Garden/Oakland Homes with Gated Amenities

Winter Garden/Oakland Homes with Gated Amenities

Welcome to Winter Garden and Oakland, Florida, where charm meets convenience in the heart of Orange County! Nestled just a stone's throw from the vibrant city of Orlando, this picturesque area boasts a delightful blend of small-town warmth and modern amenities. With its lush landscapes, historic downtown, and an array of recreational opportunities, Winter Garden and Oakland are perfect for families, retirees, and anyone seeking a serene lifestyle amidst the hustle and bustle of city life.

One of the standout features of this region is the availability of homes with gated amenities. These exclusive communities not only offer a sense of security but also foster a tight-knit neighborhood atmosphere. Imagine living in a beautifully designed home surrounded by manicured landscapes, where you can enjoy community pools, fitness centers, and walking trails, all within the comfort of your own gated enclave. Many of these homes feature modern designs with spacious layouts, gourmet kitchens, and luxurious master suites, making them ideal for those who appreciate the finer things in life.

The Winter Garden and Oakland area is also known for its top-rated schools, diverse dining options, and vibrant shopping districts, ensuring that residents have everything they need right at their fingertips. With easy access to major highways and the stunning natural beauty of nearby parks and lakes, this region truly offers the best of both worlds.

Whether you're looking to buy your first home, upgrade to a larger space, or find a peaceful retreat, Winter Garden and Oakland's gated communities provide an exceptional lifestyle that you won't want to miss. Come discover your dream home in this enchanting part of Florida!

Newest Winter Garden/Oakland Homes with Gated Amenities

$635,000
4 Beds ⋅ 3 Baths ⋅ Stoneybrook West SubDv. ⋅ 34787 Zip Code
Virtually Staged. Welcome to this beautifully renovated golf-front home in the gated community of Stoneybrook West. Offering over 2,800 square feet of living space, this home combines a spacious and flexible floor plan with a fantastic setting overlooking the 6th hole and no rear neighbors. Recent improvements include a newer roof and A/C, fresh exterior and interior paint, renovated kitchen, bathrooms, and flooring. The main level offers multiple living and dining spaces, while the kitchen features stone countertops, stainless steel appliances and abundant cabinetry. Upstairs, the spacious primary suite includes a tray ceiling, walk-in closet and private bath with dual vanities and a beautifully remodeled walk-in shower. The oversized loft provides plenty of flexibility for a second living area, media room, playroom or home office. Step outside to a large backyard with expansive golf course views and plenty of room to enjoy the outdoor living. Stoneybrook West offers an impressive collection of amenities, including a community pool, golf, clubhouse, tennis and basketball courts, playgrounds and walking paths. Ideally located near Winter Garden Village, historic Downtown Winter Garden, shopping, dining and major roadways, this home offers a great combination of space, improvements, amenities and community.

15081 Masthead Landing Circle, Winter Garden
$340,000
3 Beds ⋅ 3 Baths ⋅ Grove Residence & Spa Hotel Condo Ii SubDv. ⋅ 34787 Zip Code
Welcome to The Grove Resort & Water Park Orlando, a premier vacation resort just minutes from Walt Disney World. This spacious 3-bedroom, 3-bath condominium is located on the 3rd floor of Building 2, offering exceptional convenience to the main lobby and resort amenities. Designed for vacation enjoyment and investment potential, the residence features a spacious open floor plan, well-appointed kitchen, comfortable living and dining areas, and three bedrooms and baths providing plenty of room for family and guests. Enjoy your own Orlando vacation retreat and take advantage of rental income . The Grove offers an impressive resort experience with Surfari Water Park, multiple pools, a lazy river, FlowRider surf simulator, restaurants and bars, fitness center, spa, arcade, Lake Austin activities, and complimentary transportation to Walt Disney World. Whether your goal is creating memorable Florida vacations, generating rental income, or enjoying the best of both, this Building 2 location offers convenience, flexibility, and investment potential in one of Orlando’s most popular vacation destinations. Vacation when you want. Earn rental income when you don’t.

14501 Grove Resort Avenue Unit 2342, Winter Garden
$999,270
4 Beds ⋅ 4 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 on large homesites without a CDD. Residents enjoy all the proximity to shopping, dining, and entertainment this area is known for. Discover the perfect blend of luxury, comfort, and convenience in this stunning Mahogany Grand home. Thoughtfully designed for both everyday living and entertaining, this exceptional two-story residence offers 4 bedrooms, 3 full bathrooms, a convenient first-floor powder room, an enclosed flex room, and a spacious 3-car garage. The open-concept living area seamlessly connects the gourmet kitchen, café, and gathering room, creating an expansive and inviting space. Soaring ceilings and an elegant tray ceiling enhance the sense of openness, while a large pocket sliding glass door extends the living space onto the covered lanai, filling the home with natural light and creating the perfect blend of indoor and outdoor living. At the heart of the home, the gourmet kitchen showcases stacked soft-close cabinetry, quartz countertops, a decorative tile backsplash, farmhouse sink, and built-in Whirlpool stainless steel appliances, including a natural gas cooktop, range hood, and 48-inch side-by-side refrigerator. Whether preparing everyday meals or hosting special gatherings, this kitchen is designed to impress. Privately situated in the back corner of the home, the spacious owner's suite offers a peaceful retreat and features an owner's suite extension, providing additional space for a sitting area, fitness nook, workspace, or whatever best suits your lifestyle. The spa-inspired en suite bath includes a walk-in closet, linen closet, walk-in shower with a rain shower head, and a private enclosed water closet. The enclosed flex room at the front of the home adds valuable versatility and can easily function as a home office, fitness room, playroom, or creative studio. Two additional first-floor bedrooms located in the opposite back corner of the owner’s suite provide comfort and privacy for everyone. A conveniently located powder room further enhances the home's thoughtful design. Upstairs, enjoy an additional 884 square feet of flexible living space, complete with a generous loft, private fourth bedroom, and full bathroom, making it ideal for a media room, guest suite, home office, or multigenerational living. Completing the home is a spacious 3-car garage with ample room for vehicles, storage, and hobbies. Don't miss the opportunity to tour this exceptional home and experience everything it has to offer.

289 Crystal Wood Drive, Winter Garden
$895,260
5 Beds ⋅ 4 Baths ⋅ Winter Grove SubDv. ⋅ 34787 Zip Code
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 on large homesites without a CDD. Residents enjoy all the proximity to shopping, dining, and entertainment this area is known for. Step into the Imperial, where luxury and convenience seamlessly combine to create a truly elevated living experience. This remarkable 5-bedroom, 3.5-bathroom home with a 2-car garage situated on a conservation view homesite offers unparalleled craftsmanship and thoughtful design throughout. The open-concept layout flows effortlessly, creating an expansive, airy feel that exudes both sophistication and comfort. On the first floor, discover a private en suite bedroom with a walk-in closet and elegant quartz countertops—a perfect retreat for guests. At the heart of the home, the chef-inspired kitchen is a true masterpiece, featuring Winstead White stacked cabinetry, striking quartz countertops and a decorative tile backsplash. Built-in Whirlpool stainless steel appliances, including a refrigerator and natural gas cooktop, make cooking a pleasure. The kitchen seamlessly connects to the café and gathering room, where a sliding glass door opens to the covered lanai, featuring pre-plumbing for an outdoor kitchen to enhance indoor-outdoor living, all overlooking tranquil conservation views. The first floor also offers a convenient powder room, perfect for guests, as well as a bedroom with an attached bathroom. Upstairs, the luxurious owner’s suite is a private sanctuary, featuring a spacious walk-in closet and a spa-like en suite bathroom with quartz-topped dual vanity sinks and a frameless glass enclosed shower. The loft area provides the perfect space to unwind, while three additional bedrooms and another bathroom complete the upper level. For added convenience, a thoughtfully located upstairs laundry room simplifies everyday tasks. Beautiful wood-look tile flooring is found throughout the first floor, laundry room, and bathrooms, while plush, stain-resistant carpet complements the loft and bedrooms. Designer-curated finishes elevate every corner of this home, including thoughtfully placed brushed nickel plumbing fixtures and hardware, comfort height toilets, Whirlpool washer and dryer, 2” faux wood blinds, and wood treads and risers at the staircase. This home is equipped with a smart thermostat, video doorbell, and LED down lights ensuring your home is as connected as it is beautiful. This home offers the perfect combination of luxury, convenience, and modern design—an ideal place to live and relax. Schedule a tour today!

427 Winter Grove Boulevard, Winter Garden
$710,000
4 Beds ⋅ 3 Baths ⋅ Stoneybrook West SubDv. ⋅ 34787 Zip Code
*Some photos are virtually staged. Video tour available.* This home has a full-home SOLAR PACKAGE that is included in the sales price and generates enough energy to produce a $0 ELECTRIC BILL! The only power utility payment is a $55 monthly connectivity to Duke. That’s it! You’ll be welcomed by the inviting FRONT PORCH, fresh landscaping and EXTENDED PAVER DRIVEWAY. The spacious entry is surrounded by wood floors and upgrading lighting in the formal living and dining rooms. The tall ceiling in the family room makes the already large space feel even more grand as it opens to the kitchen and breakfast nook. This kitchen has a walk-in pantry, ample counter space, a NEW MICROWAVE and 2 NEW REFRIGERATORS, one of which is in the EXTRA-LARGE LAUNDRY ROOM. There is a full guest/pool bath downstairs with direct access to the SCREENED PATIO that runs the length of the house. Outside you’ll find a large backyard with a PRIVATE VINYL FENCE, raised GARDEN BEDS and a FIRE PIT. Two sets of sliding doors lead back to both the family room and the primary suite. The downstairs primary suite has nice natural lighting, a WALK-IN CLOSET with built-in storage, a garden tub, separate shower, and water and linen closets. Upstairs you’ll find a BARRE DANCE STUDIO, a full wall of mirrors and a fan to keep your dancers cool. This is also a versatile space if you don’t have a dancer in the family. There is also an open loft, 3 secondary bedrooms and a hall bath. Additional upgrades include TWO NEW AC SYSTEMS (2026), NEWER ROOF (2022), epoxy flooring in the garage, all appliances convey, and ceiling fans throughout! The HOA INCLUDES lightning speed fiber optic SPECTRUM INTERNET AND CABLE, access to the Olympic-sized COMMUNITY POOL, splash pad, clubhouse with FITNESS CENTER, basketball, pickleball and tennis COURTS, a community BOAT RAMP with LIMITED BOAT STORAGE and a FISHING PIER. Stoneybrook West is situated amongst great schools, restaurants, shopping, is near the 429, Turnpike, 408, historical downtown Winter Garden and of course the theme parks.

13527 Fox Glove Street, Winter Garden
$949,000
3 Beds ⋅ 4 Baths ⋅ Del Webb Oasis SubDv. ⋅ 34787 Zip Code
Welcome to this **better-than-new Renown model by Del Webb**, beautifully maintained and only used seasonally. Located on a premium wooded conservation homesite with open green space, this exceptional home offers privacy, breathtaking nature views, and magical nightly Disney fireworks. This spacious home features 3 bedrooms, 3 full baths, a powder room, flex room, and a 3-car garage with abundant storage. The open-concept floor plan is perfect for entertaining, showcasing a gourmet kitchen, white and gray cabinets with Kitchenaid Stainless Steel appliances including NATURAL GAS stove top, DOUBLE Convection ovens, built-in microwave, refrigerator, wine refrigerator, oversized island, 42" soft-close cabinetry, Lyra quartz countertops, mosaic tile backsplash, and walk-in pantry. The gathering room opens through dramatic zero-corner sliding glass doors to an extended covered paver lanai with panoramic screen enclosure and outdoor kitchen plumbing, creating seamless indoor/outdoor living. You'll be spending lots of time enjoying this gorgeous view! The private Owner's Suite features oversized walk-in closets, dual quartz vanities, linen closet, and an upgraded Super Shower. Two additional guest suites each include walk-in closets and private en-suite baths. Luxury upgrades include Plantation shutters, top-down/bottom-up cellular shades, solar shades, designer lighting, upgraded interior doors, luxury vinyl plank flooring, porcelain tile baths, Smart Thermostat, HVAC air quality package, utility sink in the garage, full rain gutters, and LG pedestal washer and gas dryer included, Tankless Natural Gas Water Heater. Enjoy the award-winning Del Webb Oasis 55+ lifestyle with a 12,000+ sq. ft. clubhouse, resort-style pool, fitness center, pickleball and tennis courts, walking trails, coffee bar, wine room, arts & crafts studio, social clubs, and a full-time Lifestyle Director. HOA includes lawn maintenance, landscaping, gated entry, and high-speed fiber internet with streaming TV. Ideally located in Horizon West, just 6-8 miles from Walt Disney World®, 2.4 miles to AdventHealth ER, and minutes to Flamingo Crossings shopping, dining, and entertainment. Move-in ready and truly better than new, experience luxury, comfort, and resort-style living at its finest!

15031 Canopy Cover Drive, Winter Garden
$290,500
3 Beds ⋅ 2 Baths ⋅ Southern Pines Condo SubDv. ⋅ 34787 Zip Code
Welcome to Southern Pines, one of Winter Garden's most desirable gated condominium communities. This spacious second floor 3 bedroom, 2 bathroom condo offers approximately 1,453 square feet of comfortable living space with an open, functional layout that is perfect for everyday living, working from home, or entertaining family and friends. The unit offers luxury vinyl flooring, the kitchen overlooks the living and dining areas, creating a bright and inviting gathering space, while the split bedroom floor plan provides added privacy for the primary suite. The generous primary bedroom features a walk in closet, and the two additional bedrooms offer excellent space for guests, family, or a home office. Southern Pines is known for its outstanding amenities, including a resort style pool and spa, clubhouse with a gaming area and a movie room, fitness center, indoor basketball and racquetball courts, tennis courts, playground, picnic and barbecue area, and beautifully maintained grounds. The monthly condominium fee also covers valuable services including water, sewer, trash, cable, internet, exterior maintenance, grounds maintenance, and security, making ownership both convenient and low maintenance. Ideally located just minutes from Historic Downtown Winter Garden, Winter Garden Village, major shopping and dining, the West Orange Trail, SR 429, the Florida Turnpike, Highway 50, and world famous attractions such as #Disney and #Universal, this home offers an exceptional combination of location, lifestyle, and value. Whether you are looking for your primary residence, a second home, or an investment opportunity, this move in ready condo is one you will not want to miss. Schedule your private showing today and discover everything Southern Pines has to offer.

142 Southern Pecan Circle Unit 204, Winter Garden
$1,499,997
6 Beds ⋅ 4 Baths ⋅ Brdford Crk Ph 2 SubDv. ⋅ 34787 Zip Code
WELCOME TO YOUR PRIVATE RESORT IN THE HEART OF WINTER GARDEN! Located behind the gates of the desirable Bradford Creek community, this exceptional 6-bedroom, 4-bath residence offers the space, flexibility, luxury, and unforgettable outdoor lifestyle today’s buyers are searching for. From the oversized driveway and 3-car garage to the breathtaking resort-style backyard overlooking the pond, this home was designed for elevated everyday living and exceptional entertaining. Step inside to a bright, expansive open floor plan featuring a formal dining room, private office or den, spacious living areas, and a highly desirable first-floor bedroom with a full bathroom—ideal for guests, multigenerational living, or a private work-from-home space. The impressive kitchen is the heart of the home and features stainless steel appliances, abundant cabinetry, a large pantry, a convenient butler’s pantry, and a seamless connection to the main living area. The first-floor laundry room adds everyday convenience, while the spacious second-floor loft offers flexible space for a media room, game room, fitness area, home office, or additional family lounge. The expansive primary suite provides a peaceful retreat with generous space and a large walk-in closet. Step outside and experience what truly sets this property apart. The fully fenced backyard has been transformed into a private resort-inspired oasis featuring a spectacular luxury pool with decorative fire features, a swim-up pool bar, and a relaxing spa. Entertain year-round from the summer kitchen and covered gazebo, unwind beside the Zen-inspired pond, gather around the dedicated fire-pit area with four loungers, or enjoy the beauty of the thoughtfully designed butterfly gardens. Low-maintenance artificial turf creates a polished outdoor setting, while peaceful pond views provide a beautiful backdrop for relaxing mornings and memorable evenings. FEATURES INCLUDE: Gated community; 6 bedrooms and 4 bathrooms; 3-car garage; oversized driveway; first-floor bedroom and full bathroom; private office or den; formal dining room; open-concept living; stainless steel appliances; large pantry; butler’s pantry; first-floor laundry; spacious loft; expansive primary suite with a large walk-in closet; resort-style pool; decorative fire features; swim-up pool bar; spa; summer kitchen; covered gazebo; pond views; Zen-inspired pond; fully fenced backyard; artificial turf; butterfly gardens; and a dedicated fire-pit lounge. Enjoy the highly sought-after Winter Garden lifestyle with convenient access to Historic Downtown Winter Garden, local restaurants, coffee shops, boutique shopping, entertainment, community events, and the popular farmers market. Explore the nearby West Orange Trail, area parks, lakes, fitness facilities, shopping centers, grocery stores, and everyday conveniences. The home also offers convenient access to major roadways, Central Florida attractions, employment centers, and the extensive shopping and dining options surrounding Winter Garden Village. This exceptional property combines the privacy of a gated community, the versatility of a 6-bedroom floor plan, and the lifestyle of a private resort in one of Central Florida’s most desirable locations. Homes offering this level of indoor space, outdoor luxury, pond views, and entertaining potential are rarely available. Schedule your private showing today and experience this extraordinary Winter Garden residence for yourself!

14384 Sunbridge Circle, Winter Garden
$615,000
4 Beds ⋅ 3 Baths ⋅ Stoneybrook West SubDv. ⋅ 34787 Zip Code
**Virtual staging in formal living and dining rooms. Video available.** Stoneybrook West is situated amongst great schools, restaurants, shopping, is near the 429, Turnpike, 408, historical downtown Winter Garden and of course the theme parks. The HOA INCLUDES lightning speed fiber optic SPECTRUM INTERNET AND CABLE, access to the Olympic-sized COMMUNITY POOL, splash pad, clubhouse with FITNESS CENTER, basketball, pickleball and tennis COURTS, a community BOAT RAMP with LIMITED BOAT STORAGE and a FISHING PIER. This home sits in the quiet Masthead Landing neighborhood with charming curb appeal. Upon entry you’ll be greeted by the spacious foyer and beautiful staircase. FRENCH DOORS lead to the PRIVATE OFFICE with abundant sunlight. There’s plenty of space for the family to relax and entertain between the formal living and dining rooms and the family room open to the kitchen. The PICTURE WINDOW provides an unobstructed POND VIEW with a distant golf course view. The eat-in kitchen has a WALK-IN PANTRY plus a closet pantry, GRANITE countertops, tile backsplash, and stainless-steel appliances. Convenience awaits in the spacious LAUNDRY ROOM with a utility sink, storage, dryer and NEW WASHING MACHINE (2025). The primary bedroom upstairs has the beautiful POND VIEW, laminate flooring, a walk-in closet with built-in shelving, a garden tub and RENOVATED SHOWER. The secondary bedrooms share the hall bathroom. Outside you’ll find a spacious SCREENED PATIO and a 2-car garage with storage racks. Interior features include a half bath downstairs, BUILT-IN SPEAKERS and MOTORIZED SHADES in the living room, touch-sensitive kitchen faucet, ceiling fans, fantastic storage, new closet doors in one bedroom, impact windows in the primary bedroom and new toilets throughout. Exterior features include LIGHTNING RODS and GUTTERS. NEW WINDOWS were installed in 2019/2022, the roof was replaced in 2017, and the water heater was replaced in 2018. This home is ready and waiting for you!

14827 Masthead Landing Circle, Winter Garden
$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
**Perfect for SNOWBIRDS!! Stay here all winter and let the onsite management company rent out your unit the rest of the year!! 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
$249,000
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
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