Skysail Real Estate

Skysail Real Estate

Welcome to Skysail, an exquisite subdivision nestled in the heart of Naples, Florida, within the picturesque Collier County. This charming community embodies the perfect blend of luxury and leisure, making it an ideal choice for families, retirees, and anyone seeking a vibrant Florida lifestyle.

Skysail is renowned for its stunning landscapes and thoughtfully designed homes that reflect the elegance of coastal living. The subdivision features a variety of architectural styles, catering to diverse tastes while maintaining a cohesive aesthetic that enhances the overall appeal of the community. Residents enjoy spacious lots, beautifully manicured lawns, and an abundance of natural light, creating an inviting atmosphere.

One of the highlights of living in Skysail is its proximity to Naples' pristine beaches, where residents can bask in the sun, take leisurely strolls along the shore, or indulge in water sports. The area is also celebrated for its world-class dining, shopping, and entertainment options. From upscale boutiques to gourmet restaurants, there’s something to satisfy every palate and preference.

For those who appreciate the great outdoors, Skysail offers easy access to nearby parks and recreational areas, perfect for hiking, biking, or simply enjoying the serene Florida weather. Additionally, the community fosters a strong sense of camaraderie, with friendly neighbors and social events that encourage connections and lasting friendships.

Discover your dream home in Skysail, where luxury meets lifestyle in one of Florida's most sought-after destinations. Experience the magic of Naples living today!

Newest Listings in Skysail

$649,000
3 Beds ⋅ 3 Baths ⋅ Skysail SubDv.
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 ⋅ 3 Baths ⋅ Skysail SubDv.
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 Circle, Naples
$581,106
4 Beds ⋅ 3 Baths ⋅ Skysail SubDv.
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 Circle, Naples
$506,023
3 Beds ⋅ 2 Baths ⋅ Skysail SubDv.
New Dream Single Family Home by Neal Communities in SKYSAIL is READY NOW!. This single family home is a 3 bedroom, Den, 2 bath and offers a 2 car garage home. UPGRADES THROUGHOUT! Gourmet kitchen package, quartz counters, upgraded cabinets, coffered ceiling, pocket sliding glass doors stainless steel appliances, upgraded tile floors throughout, IMPACT WINDOWS/DOORS, 8-ft doors, with a beautiful screened in lanai. 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 422. *Photos are of Dream Model * The images are not an exact representation of this feature home and the feature home will not be sold furnished.

4491 Centaurus Circle, Naples
$525,000
3 Beds ⋅ 2 Baths ⋅ Skysail SubDv.
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 ⋅ 3 Baths ⋅ Skysail SubDv.
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 Street, Naples
$424,900
3 Beds ⋅ 2 Baths ⋅ Skysail SubDv.
WELCOME TO SKYSAIL, ONE OF NAPLES' NEWEST RESORT-STYLE COMMUNITIES BY NEAL COMMUNITIES. THIS NEW SANDCASTLE MODEL/VILLA OFFERS AN OPEN-CONCEPT FLOOR PLAN WITH SPACIOUS LIVING AREAS, A MODERN KITCHEN FEATURING QUARTZ COUNTERTOPS, STAINLESS STEEL APPLIANCES, AND A LARGE ISLAND PERFECT FOR ENTERTAINING. THE SPLIT-BEDROOM DESIGN PROVIDES PRIVACY FOR OWNERS AND GUESTS, WHILE THE VERSATILE DEN CAN SERVE AS A HOME OFFICE, HOBBY ROOM, OR ADDITIONAL GUEST SPACE. ENJOY PEACEFUL OUTDOOR LIVING FROM THE SCREENED LANAI OVERLOOKING LANDSCAPED SURROUNDINGS. RESIDENTS OF SKYSAIL ENJOY EXCEPTIONAL AMENITIES, INCLUDING A RESORT-STYLE POOL, FITNESS CENTER, LAPPOO, LAKEHOUSE/CLUBHOUSE, TENNIS, WALKING TRAILS, AND A VIBRANT SOCIAL CALENDAR ALONG WITH AMENITIES DIRECTOR. CONVENIENTLY LOCATED NEAR SHOPPING, DINING, GOLF, BEACHES, AND ALL THAT NAPLES HAS TO OFFER. THIS IS AN EXCELLENT OPPORTUNITY TO ENJOY THE FLORIDA LIFESTYLE IN A GROWING, AMENITY-RICH COMMUNITY WITH NATURAL GAS AND LOW HOA FEES!

4580 Skysail Drive, Naples
$895,900
5 Beds ⋅ 6 Baths ⋅ Skysail SubDv.
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 ⋅ 3 Baths ⋅ Skysail SubDv.
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 Drive, Naples
$718,396
4 Beds ⋅ 3 Baths ⋅ Skysail SubDv.
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 Drive, Naples
$739,349
4 Beds ⋅ 3 Baths ⋅ Skysail SubDv.
The Lighthouse home design by Neal Communities offers an open layout for the common living areas. The beautifully-equipped kitchen comes with an island, corner walk in pantry and a cafe area. A spacious great room is open from the kitchen. In the primary bedroom suite you will find dual walk in closets and primary bath with walk in shower and private water closet. The second story features a loft and bonus bedroom with a Jack and Jill bath to maximize space and functionality of the home. 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 being built on Lot 278. The images are not an exact representation of this feature home and the feature home will not be sold furnished. A pool is not included with this home.

4235 Pegasus Way, Naples
$489,000
3 Beds ⋅ 2 Baths ⋅ Skysail SubDv.
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 Circle, Naples
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