Winter Garden/Oakland Homes with Lobby Key Required Amenities

Winter Garden/Oakland Homes with Lobby Key Required Amenities

Welcome to the enchanting region of Winter Garden and Oakland, nestled in the heart of Orange County, Florida. This vibrant community is a harmonious blend of charming small-town vibes and modern conveniences, making it a sought-after destination for families, retirees, and everyone in between. With its picturesque landscapes, rich history, and an array of outdoor activities, Winter Garden and Oakland offer a lifestyle that is as delightful as it is diverse.

The area is renowned for its beautiful parks, scenic trails, and the stunning West Orange Trail, perfect for walking, biking, and enjoying the great outdoors. The historic downtown Winter Garden is a treasure trove of boutique shops, delightful eateries, and a thriving farmers market, ensuring there’s always something to explore. With easy access to major highways and proximity to Orlando’s attractions, residents enjoy the best of both worlds—tranquility and adventure.

For those considering a home in this idyllic region, properties with lobby key-required amenities are particularly appealing. These residences often feature exclusive access to luxurious facilities, including resort-style pools, fitness centers, and beautifully landscaped common areas. Such amenities not only enhance your living experience but also foster a sense of community among residents.

Whether you're looking for a cozy single-family home or a modern townhouse, Winter Garden and Oakland have options to suit every taste and lifestyle. Embrace the charm and convenience of this vibrant area, where your dream home awaits amidst the beauty of Florida’s natural landscape!

Newest Winter Garden/Oakland Homes with Lobby Key Required Amenities

3 Beds ⋅ 4 Baths ⋅ Watermark Ph 1b SubDv. ⋅ 34787 Zip Code

WELCOME HOME to this spacious 3 bedroom / 2 full & 2 half bathroom property, located in the desirable Horizon West area of Winter Garden. Conveniently located within the Watermark community, just one mile east of the 429 and a short drive to all major theme parks, shopping and dining. Built in 2016 by Meritage Homes, this Alcott model offers over 2500sqft with a large bonus room / half bath as well as an oversized living room. Expansive backyard that contains a covered outdoor space, complete with summer kitchen and hot tub, under warranty until Feb/2027. Step into the fully fenced backyard onto the private putting green with tropical landscaping. SunPower 2KW 6-Panel solar system that is owned outright. Large 2-car garage with sealed floor, overhead storage and 50 Amp Heavy Duty EV Charging Port. Original owner who has meticulously cared for this low maintenance and energy efficient property. A/C unit replaced in Sept/2024 with 10 Year warranty. Screen enclosure structure and roof under 10 Year warranty. This property is a move-in ready gem, and will not last long. Schedule your showing today!

14681 Seton Creek Boulevard, Winter Garden

3 Beds ⋅ 2 Baths ⋅ Grove Resort And Spa Hote Condominium 3 SubDv. ⋅ 34787 Zip Code

One or more photo(s) has been virtually staged. One or more photo(s) has been virtually staged. Turn-Key, Fully Furnished 3-Bedroom Condo at The Grove Resort & Water Park!Welcome to your personal slice of paradise at The Grove Resort & Water Park, one of Orlando’s most sought-after vacation destinations just 10 minutes from Walt Disney World! This beautifully appointed 3-bedroom, 2-bathroom model offers 1,396 sq ft of spacious living, located on a high floor with tranquil views from your private screened balcony—the perfect spot to unwind after a day of adventure.Inside, you’ll find a fully equipped kitchen with quartz countertops and stainless steel appliances, seamlessly connecting to an open-concept living and dining area designed for comfort and entertaining. The primary suite features a king-size bed, luxurious en-suite bathroom with double vanity, soaking tub, and separate glass shower. Two additional bedrooms with queen-size beds and a second full bathroom ensure privacy and comfort for family and guests alike.Indulge in resort-style living with world-class amenities, including Surfari Water Park with dual water slides, a FlowRider® double surf simulator, lazy river, multiple pools, spa, fitness center, arcade, mini golf, and Lake Austin access for fishing, paddle boating, and lakeside relaxation. The resort offers on-site dining, alfresco market, and complimentary shuttle service to Disney,making your vacation effortless and unforgettable.The Grove’s professional management team can handle everything, from maintenance to short-term rentals, ensuring your investment works for you even when you’re away. HOA fees cover all utilities, including electricity, water, cable, and high-speed internet.Whether you're seeking a luxurious vacation home or a high-demand investment property, this turn-key condo offers the ultimate Florida lifestyle.

14501 Grove Resort Avenue Unit 3737, Winter Garden

4 Beds ⋅ 3 Baths ⋅ Johns Lake Pointe A & S SubDv. ⋅ 34787 Zip Code

Back on Market due to buyer unable to secure funding. Their loss, your opportunity. Location! Location! Located just 10 minutes from historic downtown Winter Garden and adjacent to the John Lake Conservation Area, you'll also enjoy easy walking and biking access to Tucker Ranch, the future site of a holistic wellness center, teaching farm, playground and family activity hub. Welcome to your move-in ready haven in Winter Garden's highly desirable Johns Lake Pointe community! This expansive 2,626 sq. ft. home sits on a generous 0.25-acre corner lot. Enjoy the comfort of a newer A/C unit and handler installed in January 2025 and freshly painted interiors (2022) that create a crisp, modern ambiance. The spacious eat-in kitchen features a large island with seating for four, ample cabinetry, a custom pantry, and extensive counter space—perfect for gatherings or morning routines. The first floor features a flexible private bonus room that can easily serve as a home office, study, or a welcoming fifth bedroom for overnight guests. The primary suite includes a beautifully crafted walk-in closet, while the custom laundry room offers built-in cabinetry and a convenient hanging bar for added functionality. Just beyond the living space, the screened-in lanai invites you to relax and unwind. Situated on a prime corner lot, the property also boasts a generously sized yard with endless potential for outdoor enjoyment. The epoxy-coated two-car garage is both functional and stylish, freshly painted and equipped with motion-sensor lighting for your convenience. This Meritage home is solid construction with 6 panel doors throughout and spray foam insulation in the attic. Community amenities include a pool, clubhouse, fitness center, yoga studio, pickleball and tennis courts—everything you need for a vibrant, active lifestyle. With its thoughtful design, abundant amenities, and unbeatable location, this home offers the perfect blend of comfort, convenience, and community.

15058 Sawgrass Bluff Drive, Winter Garden

5 Beds ⋅ 3 Baths ⋅ Stoneybrook West Un 06 SubDv. ⋅ 34787 Zip Code

WOW!!! OVER $60,000 RECENT PRICE REDUCTION!! BRAND NEW AC SYSTEM INSTALLED LAST WEEK (7/2/26) Experience refined Florida living in this beautifully enhanced home located within a highly desirable golf course community. The property offers both style and peace of mind with a roof replaced just five years ago and a recently sealed and painted exterior. Inside, the home is designed for both comfort and entertainment, featuring an immersive surround sound system throughout the main level and an impressive dedicated theater/bonus space. Every detail has been curated to elevate everyday living. Step outside to your own private retreat—an exceptional backyard showcasing a custom pool and spa with a striking grotto feature, creating the perfect setting for relaxing or entertaining guests year-round. Residents enjoy access to an array of resort-style amenities, including a clubhouse with dining, fitness center, tennis and basketball courts, beach volleyball, playgrounds, and an expansive community pool. Ideally situated just minutes from world-renowned attractions like Walt Disney World, with convenient access to major expressways and premier shopping and dining destinations nearby, this home offers the perfect balance of luxury, location, and lifestyle. One or more photo(s) have been virtually staged. PLEASE REMOVE SHOES BEFORE ENTERING THE HOME!

13412 Fox Glove Street, Winter Garden

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