Skysail Homes with Pickleball Amenities

Welcome to Skysail, a premier subdivision located in the heart of Naples, Collier County, Florida. Known for its luxurious homes and upscale amenities, Skysail offers residents a sophisticated and vibrant community to call home.

One of the standout features of Skysail is its dedication to providing top-notch recreational facilities, including homes with pickleball amenities. Whether you're a seasoned pro or a beginner looking to pick up a new hobby, you'll love having access to pickleball courts just steps away from your front door. Stay active, socialize with neighbors, and enjoy the beautiful Florida weather all year round with this fantastic amenity.

Living in Skysail means enjoying a high quality of life in a picturesque setting. From well-maintained streets to lush landscaping, every detail is designed to enhance your living experience. The community is conveniently located near shopping, dining, entertainment, and top-rated schools, making it an ideal choice for families, retirees, and everyone in between.

If you're looking for a place to call home that offers both luxury and leisure, look no further than Skysail in Naples, Florida. Come experience the best of Florida living in this charming and upscale subdivision.

Newest Skysail Homes with Pickleball Amenities

$649,000

3 Beds ⋅ 2.5 Baths ⋅ 226026261 MLS

This Beautiful nearly new FURNISHED 3 bedroom 3 bath home offers tile throughout, a gorgeous chef's kitchen with 42" cabinetry, quartz counters, stainless steel appliances including double oven & GAS cooktop. Beautiful views of the lake from the great room and lanai.You will love the breath taking sunrises and sunsets from your own private oasis! Naples newest gated community Skysail afford you the active Florida lifestyle you've been dreaming of! Resort amenities for all ages with 2 pools..spa..fitness center... lake front Clubhouse... fire pit.. pickleball..tennis.. fishing pier.. walking and biking trails.

4003 Pegasus WAY, Naples

$345,525

3 Beds ⋅ 2.5 Baths ⋅ 226025064 MLS ⋅ Skysail BLDG.

Welcome home to the Winslow at Skysail, a stunning townhome designed for comfort, style and modern living and is READY NOW! This beautifully upgraded residence features 3 spacious bedrooms, 2.1 baths, and a 1 car garage - perfect for today’s lifestyle. Inside enjoy quartz countertops, soft closing cabinetry, a designer selected backsplash and under cabinet LED lighting that elevates the kitchen’s look and feel. GE stainless steel appliances, including a washer dryer, make every day living effortless. Step outside and experience the best of the SkySail community offering resort-style amenities including a clubhouse, tennis and pickleball courts, walking trails with fitness stations, two pools, a fitness room, outdoor gaming area, fishing pier and a cozy fire pit. Pet lovers will appreciate two dedicated dog parks and the convenience of a natural gas community adds even more value. This is more than a home. It’s a lifestyle. Come discovery SkySail today. The images are not an exact representation of this feature home and the feature home will not be sold furnished. This unit is built on homesite 2904

5034 Draco CIR, Naples

$581,106

4 Beds ⋅ 2.5 Baths ⋅ 226025055 MLS

New HERITAGE Single Family Home by Neal Communities in SKYSAIL is Ready Now! This single-family home is a 4-bedroom plus loft, 2.1 bath, 2 car garage home. UPGRADES THROUGHOUT! Gourmet kitchen package, quartz counters, upgraded 42"cabinets, stainless steel appliances, IMPACT WINDOWS/DOORS, 8-ft doors and a beautiful lanai. SkySail is beautiful community offering a clubhouse, tennis and pickleball courts, walking stations and work out stations, 2 pools, a fitness room, outdoor gaming area, fishing pier and fire pit. There are two dog parks. Skysail is a natural gas community! This home is built on lot 415. *Photos are of Heritage Model * Not of actual home. Images are not an exact representation of this feature home and the feature home will no be sold furnished.

4519 Centaurus CIR, Naples

$525,000

3 Beds ⋅ 2 Baths ⋅ 226024186 MLS

Refined Lakeside Living in SkySail - Discover beautifully upgraded living in the sought-after SkySail community, where refined design meets the tranquility of lakeside living. Surrounded by 246 acres of sparkling lakes and lush natural landscaping, this exceptional residence offers the perfect blend of comfort, style, and everyday functionality while providing access to an unmatched resort-inspired lifestyle. From the moment you arrive, the home's quality craftsmanship is evident. A striking multi-lite impact glass entry door welcomes you into a bright, open great room highlighted by elegant single-step coffered ceilings that continue into the spacious primary suite. A pocket sliding glass door creates a seamless transition to the expansive covered lanai, extending your living space outdoors for effortless entertaining or peaceful mornings overlooking the spacious backyard. With plenty of room to design your own private pool, the outdoor space offers endless possibilities. At the heart of the home, the thoughtfully designed kitchen combines beauty with everyday practicality. Upgraded cabinetry with crown molding, pot-and-pan drawers, a coordinating center island, quartz countertops, a timeless herringbone backsplash, stainless steel appliances including a gas range, and a Moen Genta faucet with an undermount sink create a space equally suited for casual meals or entertaining family and friends. The adjacent utility room adds exceptional functionality with additional cabinetry, a Corian countertop, and a deep laundry sink. The primary and guest bathrooms have been beautifully appointed with upgraded cabinetry, quartz countertops, oversized wall tile, decorative accents, brushed nickel fixtures, and custom shower niches, creating spa-inspired retreats. Throughout the main living areas, durable wood-look tile flooring offers warmth and elegance, while the bedrooms feature upgraded carpeting with premium padding for enhanced comfort. Additional features include impact-resistant windows, upgraded lighting throughout, ceiling fan prewiring, a versatile den with double doors ideal for a home office and an extended two-foot garage complete with a LiftMaster opener, keyless entry, and professionally finished speckled flooring. Beyond your front door, SkySail delivers an exceptional lifestyle. Residents enjoy two resort-style pools, a dedicated lap pool and spa, a lakehouse and wellness center, eight pickleball courts, two tennis courts, event lawns, playgrounds, dog parks, and a scenic three-mile walking and biking trail. A fishing pier and kayak launch provide the perfect opportunity to enjoy the community's beautiful lakes and Southwest Florida's outdoor lifestyle. This is more than just a home, it's an opportunity to enjoy thoughtfully designed living in one of Naples' most exciting newer communities. **Please Note:** Several photographs were professionally taken when the home was furnished to help illustrate its design potential.

3980 Pegasus WAY, Naples

$739,900

3 Beds ⋅ 2.5 Baths ⋅ 226023130 MLS

One or more photo(s) has been virtually staged, AI generated or rendered. Welcome to this RARELY AVAILABLE 3-bed plus den, New Construction, 2.5 bath BRIGHT MEADOW floorplan! This spacious open concept model stuns with expansive views from the screened-in lanai. This property features upgrades galore including designer kitchen finishes with quartz countertops, stainless appliances, 3-car garage, upgraded electrical and plumbing options, and all exterior windows and doors are impact-rated. All electrical for future pool construction is complete as well as pool architectural plans. The den offers flexibility for a home office, extra guests, or a quiet reading space. SkySail is a serene home neighborhood located among 246 acres of sparkling lakes. This beautiful lakeside community offers a variety of resort amenities perfect for connecting with neighbors through outdoor relaxation or exciting activities.Neighborhood features include the lake, tennis, pickleball, trails, fishing pier, dog parks, pickleball, basketball court, fitness center, community pools, lap pool, spa, bocce, playgrounds, and a state-of-the-art community wellness and gathering center. Check out the Virtual Amenities Tour to see this wonderful neighborhood. One or more photo(s) has been virtually staged, AI generated or rendered.

3993 Perseus ST, Naples

$895,900

5 Beds ⋅ 5.5 Baths ⋅ 226017144 MLS

One or more photo(s) has been virtually staged, AI generated or rendered. PRICED TO SELL! This home would cost over ONE MILLION DOLLARS if purchased direct from the Builder. It is located on a SUPER PREMIUM lot size with stunning and expansive 180 degree lake views. With a fresh paint job throughout and only two years young, this looks and feels practically brand new! The community makes everyday life feel like an adventure—and every moment is designed for making memories. Nestled within Skysail by Neal Communities, one of Collier County’s newest and most exciting communities, this stunning lakeside residence offers the perfect blend of comfort, space, and connection. Surrounded by 246 acres of sparkling lakes, Skysail creates a peaceful, scenic setting where families can truly thrive. Step inside this beautifully upgraded two-story home featuring 5 spacious bedrooms and 4 full bathrooms, plus 2 half baths—thoughtfully designed with flexibility in mind. The main floor includes 3 bedrooms, including a luxurious primary suite, making everyday living easy and convenient. Upstairs, you’ll find 2 additional bedrooms and an expansive bonus room—perfect for a playroom, media space, friend gatherings, or guest retreat. The 2.5-car garage provides plenty of room for storage, bikes, or even your golf cart. Natural light fills the open-concept living space, where modern elegance meets comfortable living. From the plank tile flooring and tray ceilings to the custom lighting and refined finishes, every detail has been carefully selected. At the heart of the home, the chef’s kitchen is made for gathering—complete with quartz countertops, stainless steel appliances, gas cooking, a stylish tile backsplash, oversized pendant lighting, and a walk-in pantry. The primary suite offers a private escape, featuring dual vanities, a spacious walk-in shower, and a generous walk-in closet designed for both function and luxury. Step outside and experience your own backyard oasis. The screened lanai showcases a sparkling pool with a tranquil water feature, all overlooking a breathtaking lake view. Whether it’s morning coffee, afternoon swims, or sunset evenings with family, this space is designed to be enjoyed year-round. Life in Skysail extends far beyond your front door. The community is filled with amenities for every age and lifestyle—scenic walking and biking trails, a beautiful clubhouse and lakehouse, fitness center, tennis and pickleball courts, basketball, and a lap pool. Families will love the resort-style pool, playground, dog park, fishing pier, outdoor fire pit, and game room with a catering kitchen—perfect for celebrations and gatherings. This isn’t just a home—it’s a place where your family can grow, connect, and create lasting memories, and make new friends all set against the backdrop of one of Southwest Florida’s most beautiful lakefront communities. Don't delay!

3995 Pegasus WAY, Naples

$958,732

3 Beds ⋅ 2.5 Baths ⋅ 226017243 MLS

The Sea Mist plan offers a spacious, open-concept main living area that brings together the great room, dining area, and island kitchen for effortless everyday living and entertaining. The private primary suite features two walk-in closets just off the bedroom, which is highlighted by an elegant coffered ceiling. The primary bath is designed for comfort and convenience with dual sinks, a large walk-in shower, and a separate water closet. Additional features of the home include a dedicated office, a large laundry room, a generous covered lanai, a three-car garage, and a second full bath conveniently located between the two secondary bedrooms. The upgraded kitchen showcases quartz countertops, a center island, upgraded soft-close cabinetry with dovetail drawers, 42" upper cabinets, under-cabinet lighting, a designer-selected backsplash, and stainless steel GE appliances. Further enhancements include 8-foot interior doors, pocket sliding doors, recessed ceilings in the great room and primary bedroom, impact-resistant windows, and a screened-in lanai—adding both style and functionality throughout the home. The images are not an exact representation of this feature home and the feature home will not be sold furnished. This home is being built on Homesite 366.

4647 SkySail DR, Naples

$718,396

4 Beds ⋅ 3 Baths ⋅ 226017242 MLS

THE PRICE HAS BEEN REDUCED FOR MONTH OF JULY AND IS 50% OFF OF THE LOT PREMIUM, WHICH IS INCLUDED IN THE CURRENT LIST PRICE. New HARVEST 3 Single Family Home by Neal Communities in SKYSAIL. This single family home is a 3 bedroom, 3 bath, den, 3 car garage home and is being built. UPGRADES THROUGHOUT! Gourmet kitchen package, quartz counters, upgraded cabinets, coffered ceiling, stainless steel appliances, upgraded tile floors throughout, IMPACT WINDOWS/DOORS and 8-ft doors. Make your appointment to come see it today! Many benefits to living in this wonderful community is enjoying NATURAL GAS, LOW HOA FEES AND FULL OF AMENITIES! This home is built on lot 385. The images are not an exact representation of this feature home and the feature home will not be sold furnished.

4679 SkySail DR, Naples

$489,000

3 Beds ⋅ 2 Baths ⋅ 226009672 MLS

Built in 2023 and better than new, this 3-bedroom, 2-bath single-family home in gated Skysail offers upgraded finishes, impact windows and doors, natural gas, and move-in-ready convenience without the builder wait. Inside, the open great-room floor plan features high-end wood-look luxury vinyl flooring throughout the main living areas and an upgraded kitchen with quartz countertops, tile backsplash, under-cabinet lighting, stainless steel appliances, natural gas stove, pantry, and peninsula—perfect for entertaining. Additional owner upgrades include wood-look plantation shutters, remote-controlled rear blinds, whole-home air purifier integrated into the HVAC system, a water softener and filtration system, and upgraded lighting. The screened lanai overlooks a fenced backyard with western exposure—ideal for sunset evenings—and offers room for a future pool. Impact-resistant windows and doors provide peace of mind. Concrete block construction. 2-car garage. Smart home features. Skysail residents enjoy resort-style amenities including clubhouse, fitness center, community pool and lap pool, pickleball, tennis, basketball, fishing pier, kayak/canoe launch, bike/jog paths, and a dog park—all within a gated lake-centered community in one of Naples’ fastest-growing corridors.

4653 Centaurus CIR, Naples

$369,970

3 Beds ⋅ 2.5 Baths ⋅ 226004819 MLS ⋅ Skysail BLDG.

Morgan Townhome - End Unit - Water View! Unit 3001 Come home to the Morgan - a new townhome design by award winning Neal Communities. This 2 story home includes 3 bedrooms, 2.1 baths and an attached 1 car garage. Features include a large living room with a well appointed kitchen and dining space leading out to the covered lanai. The kitchen boasts stainless appliances, Quartz counters and a designer selected backsplash. A powder room, storage closet on the lanai and access to the garage area also on the first floor. The second floor offers the primary suite, along with two nicely sized bedrooms. Photos are of the plan model - these are not actual photos of the home. This home is unit 3001.

5046 Draco CIR, Naples

$790,000

3 Beds ⋅ 2 Baths ⋅ 226003064 MLS

LUXURY. LIFESTYLE. ZERO WAIT. Welcome to one of the most extensively upgraded and beautifully appointed homes in Skysail—a better-than-new lakefront masterpiece where every detail has already been perfected. Why spend months building and thousands more on upgrades when this stunning, fully furnished residence is ready to exceed every expectation from the moment you walk through the door? Built in 2023 and meticulously enhanced far beyond builder standards, this home offers the effortless elegance today’s luxury buyers demand. Soaring ceilings, impact windows and doors, designer lighting, plantation shutters, custom finishes, and an open-concept layout create a bright, sophisticated atmosphere that perfectly blends everyday comfort with refined living. At the heart of the home, the chef-inspired kitchen was designed to impress, featuring premium cabinetry, natural gas cooking, an oversized island, abundant storage, and seamless flow into the expansive great room and dining area—all framed by breathtaking long lake views. Then… step outside and discover what truly sets this property apart. Your private resort begins here. Lounge beside the spectacular heated saltwater pool featuring a sun shelf, elegant waterfall, deck jets, shimmering glass tile, and luxurious Carrara marble decking. Entertain under the panoramic screened lanai complete with a fully equipped natural gas outdoor kitchen, professionally designed tropical landscaping, and your own private putting green. Whether you’re hosting sunset dinners, weekend gatherings, or simply enjoying your morning coffee overlooking the sparkling lake, every day feels like you’re living at a five-star resort. The owner’s suite is a peaceful sanctuary with tranquil water views, spa-inspired finishes, and generous walk-in closets, while the additional bedrooms offer exceptional comfort for family and guests. Luxury extends beyond what you can see with whole-house water filtration, reverse osmosis, premium appliances, countless builder upgrades, and thoughtful custom enhancements throughout—making this home truly move-in ready with nothing left to do. Located within Naples’ exciting Skysail community, residents enjoy an unmatched resort lifestyle featuring a spectacular clubhouse, resort-style pool and spa, state-of-the-art fitness center, pickleball, tennis, walking trails, dog park, social events, and beautifully maintained grounds—all just a short drive from Naples’ white-sand beaches, championship golf courses, upscale shopping, fine dining, and everything that makes Southwest Florida one of the most desirable places to live. This is more than a home—it’s a lifestyle. A lifestyle where weekends feel like vacations, entertaining comes naturally, luxury surrounds you at every turn, and every sunset reminds you why you chose Naples. Opportunities like this don’t last. Skip the construction delays, skip the costly upgrades, and start living the luxury lifestyle you’ve earned today....

3967 Pegasus WAY, Naples

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