Skysail Real Estate

Skysail Real Estate

Welcome to Skysail, a charming subdivision nestled in the heart of Naples, Florida, where coastal elegance meets suburban tranquility. This idyllic community is the perfect blend of modern living and natural beauty, offering residents a serene lifestyle just minutes away from the stunning beaches and vibrant culture of Naples.

Skysail is characterized by its thoughtfully designed homes that showcase contemporary architecture and lush landscaping, creating a picturesque environment for families and individuals alike. With a variety of floor plans available, prospective homeowners can find the perfect fit for their lifestyle, whether it’s a cozy retreat or a spacious family abode.

Residents of Skysail enjoy a wealth of amenities that enhance their quality of life. The community features beautifully maintained parks, walking trails, and recreational facilities, encouraging an active and social lifestyle. Families appreciate the proximity to top-rated schools, while nature enthusiasts can explore the nearby preserves and waterways, perfect for kayaking, fishing, and birdwatching.

Living in Skysail means embracing the Naples lifestyle, where fine dining, boutique shopping, and cultural attractions are just a short drive away. The renowned Naples Pier and stunning Gulf Coast beaches are within easy reach, allowing residents to bask in the sun or indulge in water sports at their leisure.

Discover the charm of Skysail, where community spirit thrives, and the beauty of Florida living is at your doorstep. Join us in this delightful neighborhood and experience the best that Naples has to offer!

Newest Listings in Skysail

$650,000
3 Beds ⋅ 3 Baths ⋅ 226031475 MLS
One or more photo(s) has been virtually staged, AI generated or rendered. Welcome to 3998 Perseus Street, an exceptional lakefront home in SkySail offering luxury finishes, extensive upgrades, and move-in-ready convenience. This beautifully upgraded Neal Communities Harvest 3 model features 3 bedrooms plus a den, 3 full bathrooms, and a spacious 3-car garage on a premium lakefront homesite with peaceful water views and beautiful Florida sunsets. Better than building new, the original owners invested more than $72,000 in builder upgrades plus thousands more in improvements after closing, bringing the total investment in upgrades and improvements to over $80,000. Inside, you'll find beautiful Buckingham Oak luxury vinyl plank flooring throughout most of the home, whole-house impact windows, upgraded lighting, premium finishes, and an open-concept layout designed for entertaining and everyday living. The chef-inspired kitchen is the centerpiece of the home and features premium quartz countertops, an oversized island, upgraded Aristokraft cabinetry with crown molding and soft-close features, designer hardware, under-cabinet lighting, a dramatic tile backsplash, stainless steel appliances, and a pull-out trash and recycling cabinet. All three bathrooms feature upgraded finishes including quartz countertops, premium cabinetry, designer tile, upgraded shower glass, plumbing fixtures, and luxury hardware. Additional upgrades include an outdoor kitchen rough-in, recessed lighting, additional electrical outlets, upgraded interior doors, trim and hardware, a garage utility sink, garage service door, designer lighting, ceiling fans throughout the home and covered lanai, custom Venetian blinds, blackout curtains, decorative curtain rods, Maytag washer, and Maytag gas dryer. Step outside to the screened and covered lanai overlooking the lake and enjoy a peaceful waterfront setting with an expansive backyard offering plenty of room for a future custom swimming pool. SkySail offers natural gas and an incredible resort-style lifestyle with a clubhouse, fitness center, resort-style pool, tennis and pickleball courts, fishing pier, walking and biking opportunities, and an active social calendar. The surrounding Randall Boulevard and Orangetree corridor continues to grow, bringing shopping, dining, healthcare, schools, and everyday conveniences closer to home, with easy access to Immokalee Road, Oil Well Road, I-75, Downtown Naples, Gulf beaches, and Southwest Florida International Airport. Why wait months to build and then spend thousands more after closing? With premium lake views, impact protection, a 3-car garage, over $80,000 in upgrades and improvements, and the finishing touches already completed, this SkySail home is ready to enjoy from day one.

3998 Perseus ST, Naples
$495,736
3 Beds ⋅ 2 Baths ⋅ 226031212 MLS
Introducing the brand new Imagination 2 style floor plan by Neal Communities now in SkySail. This stunning home offers impact resistant windows and doors, 3 bedrooms plus a den, 2 full bathrooms and a 2 car garage. There are a range of premium features including a smart home package, 8 foot doors, upgraded tile flooring, stainless steel appliances and quartz countertops. SkySail is a 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 Homesite 428. The images are not an exact representation of this home and the feature home will not be sold furnished nor is a pool included with this home.

4467 Centaurus CIR, Naples
$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
$551,106
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
$520,000
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. Extended warranty is available if desired. 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
$469,000
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
$777,000
3 Beds ⋅ 2 Baths ⋅ 226003064 MLS
Your lucky number just came up—$777,000 ( LOWEST -PRICED POOL HOME in the entire Skysail Community plus -Fully Furnished ) 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 TURNKEY 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. 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.… 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. 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
Start Your Search

The data relating to real estate for sale on this web site comes in part from the Broker Reciprocity Program (BR Program) of M.L.S. of Naples, Inc. Properties listed with brokerage firms other than this company are marked with the BR Program Icon or the BR House Icon and detailed information about them includes the name of the listing brokers. The properties displayed may not be all the properties available through the BR Program. The information provided is for consumers’ personal, non-commercial use and may not be used for any other purpose.

The data relating to real estate for sale on this web site comes in part from the Broker Reciprocity Program of the Regional Multiple Listing Service of Minnesota. Real estate listings held by brokerage firms other this firm are marked with the Broker Reciprocity logo. Information Deemed Reliable But Not Guaranteed. Property locations as displayed on any map are best approximations only and exact locations should be independently verified.

Listing data © 2026 Regional Multiple Listing Service of Minnesota. All rights reserved. By searching, you agree to the EULA.