Windsor Cay Homes with Pool

Windsor Cay Homes with Pool

Welcome to Windsor Cay, a picturesque subdivision nestled in the heart of Clermont, Florida, in beautiful Lake County. This charming community offers a perfect blend of modern living and serene surroundings, making it an ideal choice for families, retirees, and anyone looking to enjoy the Florida lifestyle.

Windsor Cay is known for its stunning homes, many of which feature private pools, allowing residents to bask in the sun and enjoy refreshing dips right in their backyards. Imagine starting your day with a swim or unwinding after a long day in your own personal oasis. The homes in this community are designed with comfort and style in mind, boasting spacious layouts, modern amenities, and beautiful finishes that cater to every taste.

Beyond the inviting homes, Windsor Cay offers a friendly neighborhood atmosphere where community spirit thrives. Residents can enjoy leisurely strolls along tree-lined streets, engage with neighbors at community events, or take advantage of nearby parks and recreational facilities. With easy access to shopping, dining, and entertainment options, everything you need is just minutes away.

Living in Windsor Cay means embracing the best of Florida living, where sunny days and warm evenings are an everyday occurrence. Whether you’re lounging by your pool, exploring the vibrant Clermont area, or simply enjoying the tranquility of your new home, Windsor Cay offers a lifestyle that is both charming and fulfilling. Discover your dream home in Windsor Cay today, and experience the joys of living in this delightful community!

Newest Windsor Cay Homes with Pool

$1,299,000
10 Beds ⋅ 8 Baths ⋅ O6425429 MLS
Experience the perfect blend of luxury, flexibility, and investment potential in this exceptional 10-bedroom, 8-bath residence offering over 4,300 square feet of thoughtfully designed living space. Built in 2024, this expansive two-story floor plan is ideal for large families, multigenerational living, or maximizing short-term rental opportunities. The open-concept design creates a seamless flow between the chef-inspired kitchen, spacious gathering areas, and outdoor living space, while generously sized bedrooms and multiple private suites provide comfort and privacy for every guest. Located within the highly sought-after Windsor Cay Resort, residents and guests enjoy an outstanding collection of resort-style amenities, including a spectacular clubhouse, resort pool with lazy river, fitness center, mini golf, sports courts, playgrounds, arcade, and gated security—creating a true vacation lifestyle just outside your front door. Positioned in the heart of Central Florida’s premier vacation corridor, this home offers unparalleled convenience with easy access to Walt Disney World, Universal Orlando, world-class golf courses, shopping, dining, and major highways including US-192, SR-429, and I-4. Whether you’re searching for a luxury vacation retreat, a high-performing investment property, or a spacious primary residence, this remarkable home delivers an exceptional combination of location, lifestyle, and long-term value.

16276 Saint Martin Street, Clermont
$775,000
5 Beds ⋅ 6 Baths ⋅ S5153317 MLS
Florida Contemporary, beautifully decorated vacation home located in the desirable Windsor Cay Resort. From the moment you enter, you are welcomed into an open-concept living, dining, and kitchen space with expansive views of the private pool through oversized sliding glass doors. The screened outdoor living area is oversized and thoughtfully designed, with convenient access to a nearby half bath—perfect for pool days without tracking through the home. Inside, the living room features a custom decorative accent wall with a 75-inch Samsung curved TV, built-in storage, and a cozy fireplace. The kitchen is fully equipped and ideally laid out for cooking and entertaining, complete with a generously sized pantry. The garage has been masterfully repurposed into a game room that is sure to provide hours of entertainment. The first floor also offers a spacious primary suite with sliding glass door access to the pool, along with a discreet yet easily accessible utility room. Upstairs, you’ll find a meticulously decorated media room featuring a built-in TV, surround sound, and an electric fireplace. The adjacent dry bar, complete with wine refrigerator and LED lighting, sets the stage for unforgettable movie nights. Each of the four bedrooms upstairs is privately situated at its own corner of the home and includes an en-suite bathroom. Windsor Cay is one of Central Florida’s premier short-term rental communities, offering a 24-hour staffed gated entrance and resort-style amenities including a zero-entry pool, water slides, lazy river, hot tub, poolside cabanas, fitness center, on-site dining, sundry marketplace, arcade, mini putt-putt golf, cornhole, sand volleyball court, and daily family activities. The owner spared no expense with upgrades and furnishings, making this property truly turnkey. As an active vacation rental, showings may require flexibility—but once you experience the home, you’ll quickly see it is well worth the wait. Ideally located near Central Florida’s world-famous attractions: approximately 14 miles to Walt Disney World® Resort and Disney Springs®, 18 miles to SeaWorld®, 22 miles to Universal Studios®, and 30 miles to Orlando International Airport. HOA covers community amenities, along with yard, irrigation and trash.

16205 Saint Kitts Circle, Clermont
$649,900
5 Beds ⋅ 5 Baths ⋅ O6416356 MLS ⋅ 1280 BLDG.
Beautiful and fully turnkey five-bedroom, 4.5-bath vacation townhome in the sought-after Windsor Cay Resort! Built in 2024, this property is professionally decorated with themed rooms and is being sold fully furnished, making it ready for immediate short-term rental operations. Features include a private screened pool, spacious open-concept living area and modern finishes throughout. Ideal opportunity for investors seeking a proven vacation rental property just minutes from Orlando's world-famous attractions. Approximately 15 minutes from Disney, with easy access to shopping, dining, golf courses and major highways. Eligible for Airbnb, Vrbo and other short-term rental platforms. Resort amenities offer excellent guest appeal and strong rental potential.

1280 Blue Island Drive, Clermont
$649,900
5 Beds ⋅ 5 Baths ⋅ O6413860 MLS ⋅ 1284 BLDG.
Welcome to your fully furnished dream vacation home in the heart of Central Florida! This stunning two-story residence features five spacious bedrooms, four full baths and one half bath, offering the ideal combination of comfort, style and investment potential. Professionally decorated and turnkey ready, this home is ideal as a vacation retreat, second home or potential income-producing short-term rental property. Enjoy your private screened pool, ideal for relaxing after a day at the theme parks or entertaining family and guests. The open-concept layout provides generous living and dining spaces, while the beautifully appointed interiors create an inviting resort-style atmosphere throughout the home. In a premier resort community, residents and guests enjoy access to world-class amenities, including a spectacular clubhouse, resort-style swimming pool, lazy river, water slides, fitness center, volleyball courts and numerous recreational activities designed for all ages.

1284 Blue Island Drive, Clermont
$685,000
5 Beds ⋅ 5 Baths ⋅ S5149536 MLS ⋅ Na BLDG.
Beautiful furnished and decorated home at Windsor Cay Resort. With 5 bedrooms, 4 full bathrooms and 1 half bathroom, this property offers comfort, style and functionality in every detail. The master suite is located upstairs, ensuring privacy and convenience, while the other tastefully decorated bedrooms welcome the whole family or guests with charm and comfort. Upstairs, a wonderfully decorated loft in a home theater style offers the perfect space to relax and enjoy moments of entertainment with the whole family. The outdoor area is a true invitation to leisure: a private covered gourmet-style pool, with a balcony and outdoor barbecue – ideal for unforgettable moments with friends and family. The open-concept design integrates the kitchen, dining room and living room, promoting a modern and welcoming environment. The kitchen is equipped with stainless steel appliances, a large countertop and custom wooden cabinets. The laundry room is also equipped and ready for use. The Windsor Cay Resort offers a complete infrastructure, with a resort-style pool, gym, sports courts, barbecue areas and much more. Perfect for short-term rentals or for those who want to live as if they were on vacation all year round! Prime location, close to everything you need and just minutes from Disney parks. Don't miss this opportunity! Schedule your visit now and come see your new home or dream investment

1256 Blue Paradise Drive, Clermont
$799,000
6 Beds ⋅ 5 Baths ⋅ O6399028 MLS ⋅ Pulte BLDG.
Exceptional turnkey investment opportunity in one of Central Florida’s most desirable short-term rental and vacation home communities, Windsor Cay Resort. This stunning fully furnished 6-bedroom vacation home is ideal for investors seeking high rental income potential, strong occupancy rates, and excellent cash flow opportunity. Professionally designed with an incredible interior layout and stylish décor, this home offers spacious open-concept living areas, beautifully appointed bedrooms, and a layout that perfectly accommodates large families and vacation guests. Ideal for Airbnb, VRBO, and short-term rental use, this property is truly move-in ready and income-producing, with all furniture, décor, and contents included. Located near Walt Disney World, Universal Orlando, shopping, dining, golf, and major Central Florida attractions, this home is highly attractive to both domestic and international travelers year-round. Whether you are looking for a vacation rental investment, second home, or income-producing property, this exceptional residence offers everything today’s buyers are searching for: location, luxury, rental performance, and turnkey convenience.

1293 Emerald Row Street, Clermont
$1,495,000
10 Beds ⋅ 8 Baths ⋅ O6381858 MLS
Exceptional opportunity to own a fully furnished, income-producing vacation home in the highly desirable Windsor Cay Resort community. Built in 2024, this impressive 10-bedroom, 8-bathroom residence offers more than 4,300 square feet of beautifully designed living and entertainment space, thoughtfully created to accommodate large groups and deliver an unforgettable guest experience. The home features a spacious open-concept layout, an elegant living and dining area, and a modern kitchen with stainless steel appliances, abundant cabinetry, and an oversized island—perfect for gathering and entertaining. Professionally designed themed bedrooms add personality and excitement, while multiple ensuite accommodations provide comfort and privacy for guests. Every detail has been planned to maximize enjoyment and rental appeal. Guests can experience a private home theater, an immersive game room, and an incredible custom indoor slide that makes this property truly stand out among competing vacation homes. Outside, the screened-in pool and spa create a private resort-style retreat, complete with a covered lanai and child safety fence—ideal for relaxing, dining, and enjoying the Florida lifestyle year-round. More than a beautiful vacation residence, this is a proven short-term rental property with strong guest demand and an active booking schedule. The home’s consistent occupancy demonstrates its appeal and income-producing potential, while Windsor Cay’s resort amenities and convenient location near Central Florida’s world-famous attractions, shopping, dining, and golf make it an outstanding addition to an investment portfolio. The property is being offered fully furnished and ready to continue operating as a vacation rental. Showings are limited due to frequent guest occupancy and must be scheduled around existing reservations. **Please request the property presentation, booking information, and financial details for additional investment information.**

16000 Sandy Cliffs Drive, Clermont
$885,000
7 Beds ⋅ 6 Baths ⋅ O6376027 MLS
BRAND-NEW FEEL • FULLY FURNISHED • TURN-KEY VACATION HOME in Windsor Cay Resort. Your chance to own a spacious 7-bed / 5.5-bath home built for unforgettable stays and a high-guest-demand resort, featuring a private screened-in pool and a layout that comfortably accommodates larger groups. Themed rooms for a special vacation in the Orlando parks. The lifestyle is the headline: you’re approximately a 4-minute walk to the Reef Club clubhouse, where guests enjoy a zero-entry resort pool, lazy river, water slides, splash pad, mini-golf, fitness center, and on-site dining—all inside a gated, vacation-focused community. Location seals it. Windsor Cay sits in one of the strongest vacation corridors near the parks, about 8.1 miles to Walt Disney World and within convenient reach of Universal Studios and other major Orlando attractions, making this an ideal second-home-and-income-property combination. Schedule your private showing and secure a fully furnished, like-new resort home that’s ready to perform from day one.

1261 Emerald Row Street, Clermont
Start Your Search