Skysail Homes under $500,000

Welcome to Skysail, a hidden gem nestled in the heart of Naples, Florida, where the sun-kissed beaches meet a vibrant community. This charming subdivision offers an inviting atmosphere, perfect for families, retirees, and everyone in between. With its picturesque palm-lined streets and lush landscaping, Skysail embodies the quintessential Florida lifestyle.

What sets Skysail apart is its unique blend of affordability and luxury. Here, you can discover a variety of beautiful homes priced under $500,000, making it an ideal choice for first-time buyers or those looking to downsize without compromising on quality. These thoughtfully designed residences feature open floor plans, modern amenities, and spacious backyards, perfect for entertaining or enjoying serene evenings under the stars.

Living in Skysail means embracing the best of Naples living. Residents have easy access to an array of recreational activities, from world-class golfing and pristine beaches to charming boutiques and delectable dining options. The nearby nature preserves and parks provide ample opportunities for outdoor adventures, whether you prefer hiking, biking, or simply soaking up the sun.

Moreover, Skysail is conveniently located near top-rated schools, healthcare facilities, and major highways, ensuring that everything you need is just a stone's throw away. Whether you're looking to invest in your first home or seeking a tranquil retreat in paradise, Skysail offers the perfect blend of community, affordability, and Florida charm. Come and explore your new home in Skysail, where your dream of coastal living becomes a reality!

Newest Skysail Homes under $500,000

$496,500

3 Beds ⋅ 2 Baths ⋅ 226034968 MLS

New Dream 2 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 426. *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.

4475 Centaurus CIR, Naples

$355,517

3 Beds ⋅ 2.5 Baths ⋅ 226034964 MLS ⋅ Skysail BLDG.

Welcome home to the SAWYER at Skysail, a stunning townhome designed for comfort, style and modern living. 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 2906.

5042 Draco CIR Unit 2906, Naples

$346,780

3 Beds ⋅ 2.5 Baths ⋅ 226034958 MLS ⋅ Skysail BLDG.

Welcome home to the Avery 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 0105.

5129 Draco CIR Unit 0105, Naples

$454,900

3 Beds ⋅ 2 Baths ⋅ 226033834 MLS

Welcome to Skysail, one of Naples' newest resort-style communities by Neal Communities. This beautiful Sandcastle villa features an open floor plan with spacious living areas, three bedrooms, two bathrooms, and a versatile den ideal for a home office, hobby room, or additional guest space. The modern kitchen offers quartz countertops, stainless steel appliances, and a large center island perfect for entertaining. The split-bedroom layout provides privacy for both owners and guests, while the screened lanai offers peaceful outdoor living overlooking the landscaped surroundings. Residents of Skysail enjoy outstanding amenities, including a resort-style pool, lap pool, fitness center, tennis and pickleball courts, lakehouse/clubhouse, walking and biking trails, a new amenities director will soon join the community. Conveniently located near shopping, dining beaches, and everything Naples has to offer. Enjoy the Florida lifestyle in this growing amenity-rich community with natural gas and low HOA Fees!

4636 Skysail DR, 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

$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

$439,900

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

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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.