Location: Winding Bay Ph 1B, Winter Garden
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15324 GILLIGAN CT, WINTER GARDEN, FL 34787
$950,00010 Days on yellowkey MLS ID: O6393498
Bed: 4 Bath: 3.5 Liv Area Sq Ft: 2794 Built: 2020Monthly Fee: $102 Tax: $641 (2025)Community: Winding Bay Ph 1BSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$641
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Winter Garden’s finest — a spacious 4-bedroom, 3.5-bathroom home with a 3-car garage, pool, outdoor kitchen, and breathtaking pond views. This exceptional home is filled with custom upgrades throughout, including custom beams, a striking stone entry wall, built-in dining seating, an expanded drop zone with additional cabinetry, and a custom bar area complete with a wine refrigerator. The gourmet kitchen features 42-inch white cabinets, stainless steel appliances, a large farmhouse sink, and an oversized pantry/storage area. A first-floor den/office offers the perfect flex space for work or relaxation. Upstairs, the primary suite is a true retreat with a custom-designed bath, wood-trimmed tray ceiling, private balcony overlooking the pond, and custom built-ins in the walk-in closet. The adjacent bedroom has been transformed into a dream walk-in closet with shoe storage and a lighted vanity, but can easily be converted back into a bedroom upon request. Two additional bedrooms complete the second floor, including one with its own private ensuite, while the open loft with custom beams creates the perfect setting for a cozy movie night. A second-floor laundry room adds everyday convenience. Step outside into your private resort-style oasis, featuring stunning pond views, a tongue-and-groove stained ceiling, built-in seating, and a fully equipped outdoor kitchen with sink, grill, pizza oven, refrigerator, and stainless hood. The heated UV-filtered pool, connected to the home’s water softener system, is enhanced by a beautiful stone waterfall. A sauna and cold plunge complete this extraordinary outdoor retreat — truly an at-home resort experience. Lush landscaping surrounds the patio and pool area, creating a tropical and private escape, complemented by thoughtfully added rock garden beds and light paver stone walkways along the side of the home that enhance both beauty and functionality. Beyond the pond, a wooded area owned by Disney provides a protected natural backdrop that will never be developed, preserving both privacy and tranquility. The 3-car garage is equally impressive with custom built-ins, overhead storage racks, and a metallic epoxy floor. New exterior painting is currently in progress. Life here extends beyond the home. Morning walks along tree-lined sidewalks, friendly neighbors, nearby parks, and resort-style community amenities create a rhythm that feels both relaxed and vibrant. Residents enjoy access to a resort-style pool, oversized cabana, sports fields, playground, sidewalks, and two dog parks. Located in an area known for top-rated schools, with convenient access to shopping and dining, and just minutes from Walt Disney World Resort, this home perfectly blends Central Florida convenience with the feeling of being tucked into something truly special. More than a house — this is a place to settle in, build memories, and truly feel at home in Winter Garden.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Gretchen Carlson, Pa (407-484-0005)
15432 GILLIGAN CT, WINTER GARDEN, FL 34787
$831,00015 Days on yellowkey MLS ID: O6392254
1 Days Off yellowkey (back on 3/23/2026)
Bed: 5 Bath: 4.5 Liv Area Sq Ft: 3267 Built: 2021Community: Winding Bay Ph 1BSingle Family
Taxes:
Tax Year:
Remarks: Under contract-accepting backup offers. This home is in one of Winter Garden’s most sought after neighborhoods, offering a chance to own a modern house that combines a great location, a quality lot, and true resort style outdoor living, all just minutes from Walt Disney World and Central Florida’s main attractions. Built only five years ago, it has five bedrooms and four and a half bathrooms, with over 3,200 square feet of thoughtfully planned space that meets today’s needs for comfort, function, and style. When you walk in, the open layout, high ceilings, and natural light create a warm and inviting feel, connecting the main living areas smoothly. The kitchen is the heart of the home, featuring quartz countertops, a large island, and a design that works well for daily use and hosting guests. The way the kitchen flows into the dining and living areas adds to the spacious yet practical feel of the home. The house sits on one of the best lots in the community, offering extra privacy since there’s no neighbor on one side and a peaceful green space with walking trails nearby. Lots like this are getting harder to find in newer communities and contribute a lot to both lifestyle and long-term value. Outside is where this home really stands out. The custom pool offers a clean and modern look, complete with a sun shelf for lounging in the water and a built-in spa for relaxing. The large paver deck gives plenty of room for entertaining or enjoying quiet time outdoors, creating a private backyard that feels like a resort. Other upsides include fully paid solar panels that help save on energy and a whole home water filtration system, both adding practical benefits and long-term value. From a market perspective, houses in Winter Garden with newer construction, great lot placement, and top tier outdoor living keep attracting strong demand. With easy access to Hamlin, Winter Garden Village, main roads, dining, and entertainment, this area remains one of Central Florida’s most appealing and stable markets. This isn’t just a house it’s a lifestyle built on location, design, and lasting value.
Listing is courtesy of: RE/MAX EXCLUSIVE COLLECTION (407-447-2829)
Listing Agent: Carmelo Nuccio (321-441-6951)
15456 GILLIGAN CT, WINTER GARDEN, FL 34787
$625,000 MLS ID: A4660262
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 2571 Built: 2020Community: Winding Bay Ph 1BSingle Family
Remarks: A Rare Owner-Occupied Opportunity Just 3.9 Miles from Disney — Fireworks Views Included Located in the highly sought-after Winding Bay community of Winter Garden, this pristine single-story 3-bedroom, 3.5-bath residence offers a lifestyle few homes can match: proximity to Disney without the noise, crowds, or short-term rental turnover. This home is ideal for owner-occupants, Disney professionals, or second-home buyers seeking a quiet, stable community with low HOA fees and thoughtfully designed amenities. Short-term rentals are not permitted, creating a neighborhood atmosphere centered on consistency, pride of ownership, and long-term value. From the moment you arrive, the home impresses with its brick-paved driveway, stone-accented façade, and welcoming curb appeal, leading into a bright, open layout designed for modern living. Inside, you’ll find a spacious and functional floor plan featuring a dedicated built-in desk area, an oversized mudroom with adjacent laundry and custom cabinetry, and generously sized guest suites ideal for visiting family and friends. The heart of the home is the chef-inspired eat-in kitchen, showcasing: 42” soft-close cabinetry Quartz countertops and designer backsplash Vented range hood and built-in microwave Massive walk-in pantry Oversized island with seating for up to eight, perfect for entertaining The open dining and family room are flooded with natural light and flow seamlessly to the custom-designed backyard, where you can unwind and enjoy direct views of Disney fireworks from your own home — a truly rare and magical feature. Winding Bay residents enjoy: Community pool Dog park Low HOA of just $102/month Proximity to top-rated schools, dining, and shopping This home is move-in ready, meticulously maintained, and positioned for buyers who value location, lifestyle, and long-term enjoyment over transient use. This is not a short-term rental opportunity. It is a rare chance to own a refined, owner-occupied home minutes from Disney in one of Winter Garden’s most desirable communities. Private showings available by appointment.
Listing is courtesy of: NEXTHOME CASA BELLA ELITE (813-726-5646)
Listing Agent: Loren Rosenthal (813-726-5646)
15372 GILLIGAN CT, WINTER GARDEN, FL 34787
$870,000 MLS ID: O6367059
Bed: 4 Bath: 3.5 Liv Area Sq Ft: 2781 Built: 2020Community: Winding Bay Ph 1BSingle Family
Remarks: Stunning One-Story Home in the Heart of Horizon West – Beautifully Renovated and Move-In Ready! This exceptional one-story residence offers an open-concept design with thoughtfully planned spaces and impressive upgrades throughout. Featuring 4 bedrooms and 3.5 bathrooms, the layout includes a convenient Jack-and-Jill suite with a shared full bathroom, providing comfort and privacy for both residents and guests. Over the past year, the owners have completed extensive upgrades: a fully remodeled bathroom, removal of all carpeting, custom built-in cabinetry, modern appliances (included), heated pool, high-end automatic shade, new landscaping, and a redesigned outdoor area, plus a stunning summer kitchen under a spacious covered lanai. The home also features curtains throughout and a whole-house water filtration system, offering additional convenience and comfort. Leased solar panels are also installed, providing long-term energy savings. The kitchen is a true highlight — the oversized island comfortably seats eight people, making it perfect for gatherings and seamlessly connecting to the expansive living room. Large windows offer a beautiful view of the outdoor space, where the covered lanai, shaded areas, and heated pool create the ideal setting for entertaining and relaxation. A charming front porch adds even more appeal. Additional features include a two-car garage with an electric vehicle charger, wood-accented walls, and a layout designed for easy maintenance and everyday comfort. Located in a beautiful and highly desirable neighborhood filled with families, walking trails, dog parks, multiple playgrounds, and a refreshing community pool, this home sits in the heart of Horizon West — close to top-rated schools and everything you need just minutes away. This is a rare opportunity to own a beautifully renovated, move-in-ready one-story home that truly stands out. Perfect for families of all ages and for anyone seeking a comfortable, elegant, and exceptionally well-maintained property. Schedule your visit to this dream home today.
Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)
Listing Agent: Caroline Nijenhuis De Santis (786-399-6148)
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