Winding Cypress Houses Sold

Q: How much are the maintenance fees (HOA) in Winding Cypress?

The current monthly maintenance fee at Winding Cypress is ~0.24 per unit SqFt.

Q: What is included in the Winding Cypress monthly association dues?

The single_family_home dues at Winding Cypress cover: Insurance, Irrigation Water, Lawn/Land Maintenance, Legal/Accounting, Manager, Master Assn. Fee Included, Pest Control Exterior, Rec Facilities, Repairs, Reserve, Street Lights, Street Maintenance, Irrigation Water, Cable, Internet/Wi Fi Access, Security, Trash Removal, Lawn/Land Maintenance, , Sewer.

Q: What are the interior features of the residences?

Winding Cypress Interior features include: French Doors, Pantry, Smoke Detectors, Tray Ceiling(s), Laundry Tub, Window Coverings, Laundry Tub, Volume Ceiling, Built-In Cabinets, French Doors, Foyer, Walk-In Closet(s), Bar, Closet Cabinets, Closet Cabinets, Coffered Ceiling(s), Pull Down Stairs, Wired for Sound, Zero/Corner Door Sliders, Built-In Cabinets, Pantry, Foyer

Q: What are the available unit views from Winding Cypress?

Winding Cypress unit views: Landscaped Area, Preserve, Trees/Woods, Lake, Water, Privacy Wall, Landscaped Area, Preserve

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Sold - Feb 27, 2026

Winding Cypress, 6779 Winding Cypress Dr, Naples, Florida 34114, image 1

$910,000

3 Beds
2 Baths
2,003 SqFt
$454/SqFt

House sold in Winding Cypress6779 Winding Cypress Dr, Naples, FL 34114

This summerwood floorplan is situated on a gorgeous lake and features 3 bedrooms, a den, 2 bathrooms, a gas heated pool and spa, and an extended 2-car garage. The home includes valuable storm-ready features such as a whole-home generator, impact-resistant windows and doors, and electric hurricane screens for added protection. Inside, the home is loaded with upgrades such as a custom built-in bar, tv stand and vanity, custom cabinetry in the primary closet, pantry, and laundry room, crown molding, tray ceiling, and a modern curated accent wall. Upgraded kitchen appliances and abundant storage complete the space. Embrace the florida lifestyle with the open-concept layout seamlessly connecting indoor and outdoor living spaces. The pool deck features a spacious covered lanai overlooking the lake with a highly desirable southwest exposure, along with an outdoor kitchen and a custom saltwater pool and spa complete with a sun ledge. No detail has been spared in the garage as well, it features a mini split, insulated door, and an extra 4 feet of length, allowing room for tools, bikes and more! Winding cypress is a natural gas community with resort-style amenities! Dine at shady palm, the onsite restaurant, or enjoy pickleball, bocce, tennis, a state-of-the-art fitness center, a resort-style pool, a community garden, and even 2 dog parks for your furry friend. This pet-friendly community allows rentals, has low fees, and boasts a prime location—convenient to marco island, 5th avenue, and i-75.

Sold - Feb 10, 2026

Winding Cypress, 6699 Pennyroyal Dr, Naples, Florida 34114, image 1

$850,000

3 Beds
2 Baths
2,094 SqFt
$406/SqFt

House sold in Winding Cypress6699 Pennyroyal Dr, Naples, FL 34114

Perfection is the only way to describe this home! It shows like a model as it has been rarely lived in since built barely three years ago. Welcome to the desirable pulte/divosta mystique model located in the popular amenity rich community of winding cypress. This waterfront property sits on a dead-end cul-de-sac and is loaded with owner and builder upgrades. It's impeccably decorated and furnished and could come turnkey providing the new owner with everything you'll ever need to begin living in paradise! The mystique’s footprint, a 3 bed, 2 bath plus optional den offers the sought after open kitchen, great room, and dining area concept with split bedrooms to ensure comfort and privacy. All the bedrooms are large with the primary suite being expansive. This home's upgrades include a whole-house generator, a hurricane impact zero-corner sliding glass door that provides a spectacular indoor/outdoor living area combining an expansive great room to the under roof lanai dining and and separate sitting section. That's just part of the lighted lanai. There's an extended paver area for you to soak in the sun while you admire the custom pool with a soothing water feature. Looking out over the beautiful lake is made easy with the option "picture window" lanai screen. Electric stormsmart metal shutters enclose the lanai providing additional peace of mind, safety and security. Additional enhancements include a chef's kitchen layout with quartz counters, a natural gas cooktop and range, upgraded cabinets with above and under lighting, expansive island with an overhang to sit three, an upgraded backsplash and a large walk-in pantry. This home also boasts upgraded tile plank flooring, custom 8' doors throughout, high-end interior plantation shutters on all windows, an expanded laundry area with cabinets, counters, a utility sink, and extra storage. The 2 car garage has an insulated overhead door. Winding cypress is optimally located just 15 minutes to olde naples, 10 minutes to both marco island and i75, and 30 minutes to rsw airport. For this price point, the amenities at winding cypress are second to none. A resident's only full service restaurant, resort pool with spa that rivals a las vegas hotel, pickleball, tennis, and bocce courts, the best fitness center around, an vibrant community center with onsite management and activities director, a dog park, community garden, and a boardwalk nature trail are just a few of the things that make winding cypress so special. With only 766 single-family homes spread out over 1250 total acres that includes 850+ acres of spectacular preserve and lakes, enjoy the peace, serenity and beautiful wildlife that few communities are able to offer.

Sold - Feb 3, 2026

Winding Cypress, 7716 Winding Cypress Dr, Naples, Florida 34114, image 1

$1,150,000

3 Beds
3¹/₂ Baths
2,923 SqFt
$393/SqFt

House sold in Winding Cypress7716 Winding Cypress Dr, Naples, FL 34114

This home is an amazing value for winding cypress!! Once you compare, you'll agree. The stonewater model is the largest one floor living within the community. The sought after "open area concept" footprint boasts 3 expansive bedrooms including a most impressive owner's suite, 3 full baths plus and additional pool bath , a large den-flex room with glass french doors, desirable 3 car garage with additional storage racks overhead. Upgrades include an executive waterfront and private preserve view lot, pool with integral spa.

Sold - Jan 27, 2026

Winding Cypress, 7659 Jacaranda Ln, Naples, Florida 34114, image 1

$575,000

2 Beds
2 Baths
1,544 SqFt
$372/SqFt

Villa sold in Winding Cypress7659 Jacaranda Ln, Naples, FL 34114

Welcome to this charming 2-bedroom plus den, 2-bath beautiful villa in the highly desirable community of winding cypress. Built in 2017, this residence offers 1, 544 square feet of thoughtfully designed living space. The interior is light and bright, featuring easy-care tile floors in the main living areas, a breakfast bar for casual dining, and carpet in the bedrooms for added comfort. The den with french doors provides the perfect space for a home office or flex room, while the primary suite offers a private retreat with dual sinks and a walk-in shower. For added peace of mind, the home is equipped with a built-in taexx pest control system. Step outside to your private backyard oasis, complete with a sparkling inground pool — new pentair 1.5 hp superflo variable speed pool pump installed september 2025 — perfect for relaxing or entertaining guests year-round. Winding cypress is known for its resort-style amenities, including a large clubhouse, community pool with cabanas, fitness center, tennis, pickleball, and bocce courts, plus walking and biking trails surrounded by natural preserves. Ideally located in east naples, you’re just a short drive from marco island, downtown naples, shopping, dining, and world-famous gulf beaches. This home is the perfect combination of comfort, convenience, and community living.

Sold - Jan 27, 2026

Winding Cypress, 7815 Jacaranda Ln, Naples, Florida 34114, image 1

$620,000

2 Beds
2 Baths
1,574 SqFt
$394/SqFt

Villa sold in Winding Cypress7815 Jacaranda Ln, Naples, FL 34114

Priced to sell!! This beautiful cressida model villa in highly sought-after winding cypress is move-in-ready. Freshly painted inside and out. Roof and all pavers have been power washed and sealed this beautiful villa offers two bedrooms, two baths plus a den along with a two-car air-conditioned garage. The den can be easily converted into a third bedroom. Step onto your lanai with the largest pool and hot tub available in a villa. Couple that with a spectacular long lake view and you truly have a one-of-a-kind home. Winding cypress offers resort-style living with a large amenity center, gym, exercise room, library, internet cafe, event room and restaurant. The resort-style pool has a lap lane and waterfall. Other amenities include pickleball, tennis, bocce, community garden and dog park. The community boardwalk allows you to walk deep into the preserve. Winding cypress boasts 800 acres of untouched preserve surrounding our one-of-a-kind community.

Sold - Jan 16, 2026

Winding Cypress, 6856 Winding Cypress Dr, Naples, Florida 34114, image 1

$858,500

3 Beds
2 Baths
2,084 SqFt
$412/SqFt

House sold in Winding Cypress6856 Winding Cypress Dr, Naples, FL 34114

Sense the comfort and beauty of this magnificent home the minute you enter the foyer and see the view out to the inviting pool and spa. This 3 bedroom, plus separate den, great room floor-plan is perfect for entertaining or just a lovely place to call home. These original owners have impeccably maintained the home making it feel brand new. Built in 2021 it boasts a chef's delight kitchen with stainless steel appliances, center island and breakfast bar, natural gas cooktop/range, pull-out drawers, quartz counter-tops, recessed and pendant lighting, and more! The cook of the house will love it! The great room and dining area are adjacent to the kitchen. An extra plus is the den with double raised paneled doors and a window for natural light. The main bedroom is approx 14' x 16' and sits on its own separate wing from the other bedrooms. You will love the main bathroom with its 9' x 3'3" tiled shower with multiple shower heads, dual sinks, quartz counter-tops, walk-in closet and separate toilet closet. It is very spacious! Another plus to this home is the zero corner doors off the great room extending your great room out to your covered lanai. The extended lanai is all plumbed for the outdoor kitchen of your liking. Enjoy the florida sunshine in your pool and spa in the privacy of your own backyard which backs up to a preserve. Some of the other features of this lovely home are a 9' x 7' laundry room with cabinets, folding counters, sink, and storage closet, 2 car garage with a 4 foot extension and epoxy flooring, and impact resistant windows and sliders. The home boasts beautiful tile and light colors throughout. The white plantation shutters in many of the rooms add to the character of the home. Winding cypress is a newer, well maintained community offering an abundance of amenities. You will find a resort-style pool and separate spa, cabanas, shady palm cafe, pickleball, bocce, tennis, state-of-the-art fitness center, community garden and a dog park for your fur babies. Winding cypress sits in a great location in collier county, less than 30 minutes from beautiful 5th avenue in naples, and the white sand beaches of marco island. This home is a must see!

Sold - Dec 15, 2025

Winding Cypress, 7355 Mockingbird Ct, Naples, Florida 34114, image 1

$875,000

3 Beds
2 Baths
2,198 SqFt
$398/SqFt

House sold in Winding Cypress7355 Mockingbird Ct, Naples, FL 34114

This extended summerwood floorplan is situated on a private street and features 3 bedrooms, a den, 2 bathrooms, a gas heated pool and spa, and an extended 2-car garage. The home includes valuable storm-ready features such as a whole-home generator, impact-resistant windows and doors, and electric hurricane screens for added protection. The open-concept layout seamlessly connects indoor and outdoor living spaces. The pool deck features a large covered lanai ideal for enjoying sunset views over the lake and preplumb of electric, gas, and water providing the option to add a built-in outdoor kitchen. Additional upgrades include tile flooring throughout, plantation shutters, trey ceiling, custom screened entryway, widened walkway & driveway and generous storage space. Turnkey furnishings are available with the sale, some exclusions. Winding cypress is a natural gas community with resort-style amenities! Dine at shady palm, the onsite restaurant, or enjoy pickleball, bocce, tennis, a state-of-the-art fitness center, a resort-style pool, a community garden, and even 2 dog parks for your furry friend. This pet-friendly community allows rentals, has low fees, and boasts a prime location—convenient to marco island, 5th avenue, and i-75.

Sold - Dec 5, 2025

Winding Cypress, 7370 Mockingbird Ct, Naples, Florida 34114, image 1

$645,000

2 Beds
2 Baths
1,805 SqFt
$357/SqFt

House sold in Winding Cypress7370 Mockingbird Ct, Naples, FL 34114

Welcome to your dream home at 7370 mockingbird court in beautiful naples, fl! This charming 2-bedroom, 2-bathroom residence, with a versatile den that can easily be converted into a third bedroom, offers a spacious 1, 805 square feet of living space, perfectly nestled on an 8, 276 square foot lot. Step inside to discover a welcoming interior featuring both carpet and tile floors, ideal for comfort and style. The open living area is enhanced by new ceiling fans and pendant lighting, creating a bright and airy atmosphere. The kitchen is a chef's delight with brand new quartz countertops, a new sink and faucet, and a suite of new appliances including a dishwasher, refrigerator, and garbage disposal. The master suite offers a serene retreat with a new toilet in the master bath, ensuring modern convenience. Enjoy the luxury of central ac and gas heat throughout the home. The attached garage, equipped with a new garage door opener, provides ample space for parking and storage. Outdoor enthusiasts will appreciate the common outdoor space, private outdoor areas, and stunning lakefront views. The community amenities are second to none, featuring a pool, hot tub, gym, tennis court, and pickleball facilities. For those who love the water, the property is waterfront with lake views, perfect for tranquil evenings. Plus, there is room to add a pool, allowing you to customize your outdoor oasis. Additional features include a new gas hot water heater, added landscape lights, and a recently cleaned roof. Plus, enjoy the convenience of laundry in the building and a washer/dryer in the unit. Conveniently situated just minutes from shopping, dining, and all the attractions naples has to offer, this home combines tranquility with exceptional lifestyle opportunities. This home is a true gem, offering a blend of comfort, style, and community amenities that make it a perfect place to call home. Don't miss the opportunity to make it yours!

Sold - Nov 21, 2025

Winding Cypress, 6839 Winding Cypress Dr, Naples, Florida 34114, image 1

$1,260,000

3 Beds
3 Baths
2,515 SqFt
$501/SqFt

House sold in Winding Cypress6839 Winding Cypress Dr, Naples, FL 34114

This pinnacle floorplan is situated on the largest lake in the neighborhood and features 3 bedrooms, a den, 3 bathrooms, a pool and spa, and a 3-car garage. The open-concept layout includes a dramatic zero-corner slider that seamlessly connects indoor and outdoor living spaces. Peace of mind comes with a whole-home generator and impact-resistant windows and doors. Inside, you'll find extensive upgrades throughout. The kitchen boasts built-in appliances and a spacious island—perfect for entertaining. Additional highlights include soaring tray ceilings, crown molding in the den and entry, and tile flooring throughout. The air-conditioned 3-car (extended by 4 ft) garage offers ample storage with custom shelving and a built-in workbench. Outdoors, the heated pool and spa are powered by both gas and solar, a smart, energy-efficient combination. The expansive outdoor kitchen, hurricane screens for added protection, and generous deck space create an ideal setting for sunset views. Other exterior features include lush landscaping with low-voltage lighting, an extra-wide driveway (recently sealed), a custom designed screened-in entryway, and panoramic wide lake views. Winding cypress is a natural gas community with resort-style amenities! Dine at shady palm, the onsite restaurant, or enjoy pickleball, bocce, tennis, a state-of-the-art fitness center, a resort-style pool, a community garden, and even 2 dog parks for your furry friend. This pet-friendly community allows rentals, has low fees, and boasts a prime location—convenient to marco island, 5th avenue, and i-75.

Sold - Nov 17, 2025

Winding Cypress, 6767 Pennyroyal Dr, Naples, Florida 34114, image 1

$990,000

3 Beds
2 Baths
2,185 SqFt
$453/SqFt

House sold in Winding Cypress6767 Pennyroyal Dr, Naples, FL 34114

Wow! This beautifully designed and meticulously maintained home checks all the right boxes. Featuring the highly desirable summerwood floor plan with great room extension, it is perfect for entertaining or simply relaxing at home after a nice day out in beautiful naples, fl. The kitchen features upgraded appliances, quartz countertops, an oversized island and walk-in pantry. The two guest bedrooms provide enough room for guests. The office/den can easily serve as a 4th bedroom if desired. Other interior features include high-grade porcelain tile throughout, a laundry/utility room with plenty of storage and natural gas for cooking, heated water and clothes drying. Exterior upgrades abound with a one-of-a-kind extended lanai with custom pavers and a built-in outdoor kitchen. There is plenty of space for outdoor gatherings, cookouts, an afternoon nap, a dip in the pool or just taking in some florida sunshine. Looking through the huge portrait "no-see" lanai screen is one of the very best long water views in the entire community. The view is simply gorgeous, inspiring "wows" from all. The driveway and side walkway are extended. There is over $100k in upgrades to this magnificent home. Just pack your bags and head on down to enjoy our very special slice of tropical paradise. Worried about maintenance and insurance costs, and/or storms? Newer construction (2021) negates a large future roof replacement cost for some time. And a newer a/c system should provide many more years of solid service. Hurricane impact doors and windows are throughout providing for great energy efficiency and home protection. Also, the lot of this property is elevated. It is not in a mandatory flood insurance zone. And there is a whole home gas generator too should the need ever arise. All aforementioned should assist in obtaining lower insurance premiums and keep maintenance costs down. This home offers easy peasy and worry-free living by any measure. To top it all off, this sensational home resides in the highly prized community of winding cypress. An onsite restaurant, modern fitness center, community pool and a full calendar of social gatherings with some of the best naples residents around are a nice walk, bike or golf cart ride away. Also, located conveniently between downtown naples and marco island, opportunities to visit some of our finest beaches, shopping and dining locations are just minutes away. Great home. (check.) great view. (check.) great community. (check.) great location. (check.) this property checks all the right boxes for the time of your life in beautiful naples, fl.

Sold - Nov 17, 2025

Winding Cypress, 7642 Jacaranda Ln, Naples, Florida 34114, image 1

$455,000

2 Beds
2 Baths
1,554 SqFt
$293/SqFt

Villa sold in Winding Cypress7642 Jacaranda Ln, Naples, FL 34114

Tucked away treasure in winding cypress- step into a slice of serenity with this charming attached villa, nestled in one of the most peaceful corners of naples. Unlike the typical coastal designs so common in the area, this home offers a more rustic warmth—perfect for those who appreciate natural textures, cozy finishes, and a relaxed, grounded lifestyle. With 2 bedrooms, a versatile den, 2 full bathrooms, and a 2-car garage, this villa checks all the boxes for comfort and functionality. The open layout is inviting yet intimate, ideal for both quiet evenings and casual entertaining. The kitchen is equipped with natural gas—a rare find that’s perfect for those who love to cook and value energy efficiency. Step outside to the screened-in lanai where mornings are best spent with coffee in hand, surrounded by the sounds of nature and a view of your private backyard oasis. An extended outdoor patio provides the perfect space to unwind under the stars. Located within the gated, master-planned community of winding cypress, this home offers so much more than just a beautiful space—it’s part of a vibrant lifestyle. Developed by divosta homes and surrounded by over 800 acres of natural preserves and 80 acres of lakes, winding cypress is a nature lover’s dream, tucked beside the picayune strand forest. Residents enjoy top-tier amenities including the shady palm café, a stunning resort-style waterfall pool, clubhouse, fitness center, tennis, bocce, and pickleball courts, and scenic walking trails. Plus, you’re just minutes from shopping and dining at tamiami crossing and freedom square. If you’ve been waiting for a home that feels like a true escape—but still close to it all—7642 jacaranda ln is calling.

Sold - Nov 14, 2025

Winding Cypress, 7049 Live Oak Dr, Naples, Florida 34114, image 1

$800,000

3 Beds
2 Baths
2,230 SqFt
$359/SqFt

House sold in Winding Cypress7049 Live Oak Dr, Naples, FL 34114

Enjoy resort-style living in this winding cypress community near 5th avenue and marco island. This home features a private pool, sunroom and the community’s largest covered lanai. Designed for year-round comfort, it offers a new air-conditioning system with additional cooling in the primary suite, impact glass throughout, and natural gas for efficiency and gourmet cooking. Inside, the oversized primary shower, upgraded tile and premium counters elevate everyday living. Set on a quiet street just a short distance to the club at winding cypress, you’ll have dining, pickleball, tennis, bocce and a resort pool at your fingertips. Mature landscaping and preserve views ensure privacy while the open layout makes entertaining effortless. With nearly 2, 300 square feet of living space, this residence blends comfort, convenience and the best of the florida lifestyle with resort living just around the corner.

Sold - Nov 6, 2025

Winding Cypress, 6787 Winding Cypress Dr, Naples, Florida 34114, image 1

$710,000

2 Beds
2 Baths
1,654 SqFt
$429/SqFt

House sold in Winding Cypress6787 Winding Cypress Dr, Naples, FL 34114

Step inside through a welcoming entryway and discover an open-concept floor plan. The heart of the home is the great room with tray ceiling and crown moldings, the modern kitchen, beautifully appointed with granite countertops, sleek stainless-steel appliances, and a generous center island suited for both everyday living and effortless entertaining. The primary suite offers a peaceful retreat with a walk-in closet, double vanity, walk-in shower. This beautifully cared-for home offers a rare opportunity to enjoy an elevated lifestyle in a sought-after winding cypress community—

Sold - Oct 30, 2025

Winding Cypress, 7235 W Clamshell Ln, Naples, Florida 34114, image 1

$1,000,000

3 Beds
3 Baths
2,512 SqFt
$398/SqFt

House sold in Winding Cypress7235 W Clamshell Ln, Naples, FL 34114

Location, location! This meticulously maintained and decorated pinnacle model located on a corner lot with privacy on both sides including a lake and wooded area view is unique! Conveniently located within walking distance to clubhouse! The home features 3 bedrooms plus a den, 3 full baths and 3 car garage in this highly sought after natural gas community of winding cypress! This large lanai features a custom gas outdoor kitchen and a beautiful custom pool and spa! A must see to be appreciated! Home protection includes impact windows, sliders and electric shutters winding cypress offers a beautiful clubhouse, resort style pool and spa and waterfall feature! In addition to pickleball, tennis, bocce, state of the art fitness center and on-site director for classes! A dog park, community garden and plenty of biking and walking trails to enjoy!

Sold - Oct 9, 2025

Winding Cypress, 6870 Winding Cypress Dr, Naples, Florida 34114, image 1

$860,000

3 Beds
2 Baths
2,084 SqFt
$413/SqFt

House sold in Winding Cypress6870 Winding Cypress Dr, Naples, FL 34114

This turnkey furnished mystique home feels like a model — impeccably maintained, thoughtfully laid out, and filled with cozy, stylish touches throughout! The floorplan features 3 bedrooms + den, 2 baths, pool and spa, and an oversized car garage. The open-concept layout features a dramatic zero-corner slider, seamlessly connecting indoor and outdoor spaces, while the whole home generator, exterior cameras, and impact windows and doors provide peace of mind. Inside, extensive upgrades are everywhere. The kitchen boasts a spacious island with upgraded appliances, perfect for entertaining. Additional highlights include tray ceilings, crown molding, tile flooring throughout, upgraded showers in both bathrooms, and an upgraded washer and dryer. You will have tons of storage space in the air conditioned and insulated garage with an extra 4 feet of space. Outside, the pool and spa is heated by gas and hurricane screens add a second layer of protection. There are plenty of seating areas, and a picture window lanai screen to enhance the quiet, private preserve view. Winding cypress is a natural gas community with resort-style amenities! Dine at shady palm, the onsite restaurant, or enjoy pickleball, bocce, tennis, a state-of-the-art fitness center, a resort-style pool, a community garden, and even a dog park for your furry friend. This pet-friendly community allows rentals, has low fees, and boasts a prime location, central to marco island, 5th avenue, and i- 75.

Sold - Sep 29, 2025

Winding Cypress, 7773 Jacaranda Ln, Naples, Florida 34114, image 1

$635,000

2 Beds
2 Baths
1,554 SqFt
$409/SqFt

Villa sold in Winding Cypress7773 Jacaranda Ln, Naples, FL 34114

On a premium oversized lot, this beautifully upgraded villa offers one of the most stunning sunset water views in all of winding cypress. The extended screened lanai features a panoramic no-see-um screen, heated saltwater pool, and a fully equipped outdoor kitchen with a five-burner bull grill, stainless steel sink, premium refrigerator, and a 42-inch lighted vent hood, an entertainer’s dream and the ultimate space to relax and take in the view. Hurricane-impact windows and doors throughout the home provide peace of mind, while a stylish glass entry door, two ceiling-mounted garage storage racks, and attic access in the garage and primary closet add smart functionality. Inside, the open floor plan is elegant and inviting with diagonal tile flooring, plantation shutters and upgraded led recessed lighting. The home includes two furnished bedrooms plus a flexible den with 8-foot french doors and a new murphy bed, ideal for guests or a home office. The gourmet kitchen features granite countertops, a tasteful tiled backsplash, staggered cabinetry with under- and over-cabinet lighting, and bar seating. California closets have been added to the primary suite and kitchen pantry for optimal organization. This smart home includes a nest thermostat, video doorbell, cameras at garage and lanai, nest protect smoke and co2 detectors and leviton wi-fi lighting switches. Gently lived in as a pet-free, smoke-free seasonal home, it shows like new. Winding cypress offers over 800 acres of natural preserves, a resort-style clubhouse with a heated pool, restaurant, fitness center, white sand beach, tennis and pickleball courts, dog park and scenic nature trails. With low hoa fees and a natural gas community, all just 25 minutes to 5th avenue, 20 minutes to marco island and five minutes to major shopping, this home blends luxury, peace of mind and lifestyle in one incredible package.

Sold - Sep 22, 2025

Winding Cypress, 7597 Blackberry Dr, Naples, Florida 34114, image 1

$1,175,000

3 Beds
3 Baths
2,496 SqFt
$471/SqFt

House sold in Winding Cypress7597 Blackberry Dr, Naples, FL 34114

Excepional in design and setting, this pinnacle model commands southwest-facing lake and preserve views from one of the most private parcels within winding cypress. The residence is enhanced by an extended, climate-controlled 3 car garage with a high-performance polymer finish—offering utility and esthetic. Interior features include 12’ ceilings, tray ceilings, tile flooring throughout, plantation shutters, and custom millwork. The open-concept floor plan includes a great room with electric sliding doors leading to the lanai. The kitchen is equipped with quartz countertops, a large island with built-in wine cooler, kitchenaid and whirlpool appliances, and a natural gas cooktop. The primary suite includes custom closets and an en-suite bath. The home is equipped with a whole-house generac generator, whole-house water purification with reverse osmosis, and a built-in surround sound system in the great room, primary bedroom, and lanai. A full home security system is also installed. Outdoor living space features an extended lanai with a custom aragon pool and spa and an upgraded outdoor kitchen great for entertaining... Winding cypress amenities include a clubhouse, fitness center, resort-style pool, tennis courts, pickleball, bocce, dog park, and nature trails.

Winding Cypress, 7128 Lily Way, Naples, Florida 34114, image 1

$750,000$150K

2 Beds
2 Baths
1,685 SqFt
$445/SqFt

House for sale in Winding Cypress7128 Lily Way, Naples, FL 34114

Thoughtful price improvements, upgraded finishes throughout, an expanded kitchen island & a rare 4-foot extension in the garage sets this home apart - topped off by a stunning private pool overlooking the lake. This property offers exceptional appeal. This is a stunning abbeyville home in winding cypress, a move-in ready! This immaculate residence is a must-see, featuring a fresh neutral palette, offering a spacious open split-bedroom floor plan with 2 bedrooms, a flex/den & 2 full bathrooms. Entertainment is elevated with flat-screen tvs mounted in both bedrooms & living area. Soaring ceilings enhanced by elegant molding, tray & coffered details, along with extra recessed lighting. Plantation shutters in the front bedroom, flex/den & over the kitchen sink add both privacy & style. Enjoy matching tile flooring throughout the main areas, with warm wooden plank flooring accentuating the flex/den room. A new hvac unit, installed in december 2021 & serviced bi-annually ensures year-round comfort. The gourmet kitchen is a chef’s delight with upgraded white shaker cabinets, quartz countertops, a stylish subway tile backsplash & stainless steel appliances including a gas range & hood, dishwasher, built-in microwave, & a stainless steel sink with in-sink disposal. Exquisite cabinet lighting brightens the space, while a large extended kitchen island with additional cabinets provides ample storage. The primary suite features a luxurious walk-in shower with a glass enclosure, dual vanities with a quartz countertop, leading onto a fabulous walk-in closet with built-in organizers. The guest bathroom similarly boasts upgraded features with a tub & shower/glass enclosure, quartz countertop & spacious linen closet. The convenient laundry room is outfitted with upgraded front-load washer & dryer along with built-in cabinets & organizers. Outside, the stunning outdoor oasis beckons with a crystal-clear kidney-shaped pool offering serene lake views. Privacy hedges frame the pool cage, which features both covered & uncovered lanai areas - the perfect balance for year-round enjoyment. Upgrades include new pool cage screens & a pool heater (december 2022). Additional features include built-in easy-to-slide high-end accordion hurricane shutters & an extended 2-car garage with epoxy flooring. Located in the premier winding cypress community - a highly sought-after natural gas community set among 800 acres of natural preserves & 80 acres of lakes - this home offers resort-style amenities including a lap pool with spa, screened-in outdoor bar & grill (the shady palm), fire pits, fireplace, two dog parks, a community garden, tennis, bocce & pickleball courts, a state-of-the-art clubhouse with a fitness center plus event rooms. Ideally situated just minutes from downtown naples, several beaches, marco island & us-41/i-75, this property blends luxury & convenience effortlessly. Don’t miss out on this incredible opportunity!

Winding Cypress, 7788 Winding Cypress Dr, Naples, Florida 34114, image 1

$975,000$575K

3 Beds
3 Baths
2,496 SqFt
$391/SqFt

House for sale in Winding Cypress7788 Winding Cypress Dr, Naples, FL 34114

Nestled within an exclusive gated community and surrounded by a serene nature preserve, this elegant 3-bedroom, 3-bathroom home with a spacious den/office is the epitome of refined florida living. The open, airy floor plan flows seamlessly, with high ceilings and large windows that capture abundant natural light and offer unobstructed views of the lush preserve behind the home. This home has natural gas, generator, upgraded oversized garage, sentricon system, central vac system, and many more upgrades. Step into the gourmet kitchen, complete with premium appliances, custom cabinetry, and an expansive island that's perfect for entertaining or family gatherings. Each bedroom is generously sized, featuring high-end finishes and ample storage, while the den/office provides an ideal, private space for working from home or additional relaxation. The master suite is a tranquil retreat with a luxurious en-suite bathroom featuring dual vanities, and a walk-in shower. Outdoors, your private paradise awaits, with a sparkling gas heated salt water pool and spa surrounded by a spacious patio, perfect for sunbathing, al fresco dining, or evening cocktails under the stars. The 3-car garage offers plenty of room for vehicles, storage, and hobbies. Living in this community comes with exceptional amenities that rival a luxury resort. Enjoy an on-site restaurant, a spectacular resort-style pool, tennis courts, pickleball, bocce, and a dog park, all thoughtfully designed to elevate your lifestyle. The well-appointed fitness center, internet café, and an engaging calendar of year-round social events ensure that there's always something to do. Centrally located between the pristine beaches of marco island and naples, this home places you just moments away from world-class shopping, dining, and entertainment, yet offers a peaceful, nature-filled escape in your own backyard. Don't miss the opportunity to make this luxurious haven yours!

Winding Cypress, 7445 Winding Cypress Dr, Naples, Florida 34114, image 1

$674,000$125K

3 Beds
2 Baths
2,198 SqFt
$307/SqFt

House for sale in Winding Cypress7445 Winding Cypress Dr, Naples, FL 34114

Welcome to this beautifully appointed 3-bedroom, 2-bathroom + den home in the vibrant and sought-after community of winding cypress in naples. Perfectly positioned on a prime lakefront lot, this residence offers serene, long water views that extend to the untouched beauty of the preserve beyond. Thoughtfully designed for both comfort and style, this home features tall interior doorways, an extended screened-in lanai, a fully equipped outdoor kitchen—ideal for entertaining or enjoying peaceful evenings overlooking the lake, and enjoy the convenience of an extended garage — perfect for extra storage, a workshop space, or oversized vehicles.. Storm shutters provide added security and peace of mind, while the open and versatile layout includes a den perfect for a home office or flex space. The well-appointed kitchen boasts a gas range, catering to culinary enthusiasts, and a natural gas whole-home generator ensures uninterrupted comfort during any weather event. Additional conveniences include an hoa that covers landscaping and irrigation water, allowing for low-maintenance living. Winding cypress is a gated, resort-style community offering an exceptional array of amenities. Residents enjoy a luxurious clubhouse, a tropical pool with waterfall features, a soothing spa, and a state-of-the-art fitness center. Recreational and social opportunities abound with pickleball, tennis, bocce, and a full calendar of community events. The shady palm café serves delicious food and drinks poolside, while a scenic boardwalk winds through the community’s pristine natural surroundings. A spacious, secure dog park makes this neighborhood perfect for pet lovers as well. Conveniently located just off us-41, winding cypress offers easy access to world-class dining, shopping, entertainment, and the white-sand beaches that define naples living. Experience the perfect blend of privacy, luxury, and vibrant community life in this exceptional home.

Winding Cypress, 6763 Winding Cypress Dr, Naples, Florida 34114, image 1

$880,000$90K

3 Beds
2 Baths
2,107 SqFt
$418/SqFt

House for sale in Winding Cypress6763 Winding Cypress Dr, Naples, FL 34114

This exquisite 2021 residence showcases the meticulous care of its single owner and boasts numerous upgrades throughout. It features a heated pool, three bedrooms, two bathrooms, and a den, providing ample space for living and entertaining. Situated on a picturesque lake in the serene winding cypress community. The heart of the home is a spacious, light-filled living area and a large kitchen with a generous island for seating. Culinary enthusiasts will appreciate the five-burner gas stove and the convenience of a butler's pantry. The exquisite quartz coutertops complete the perfect setting for entertaining and everyday living. The home is adorned with impact window and sliders, allowing natural light to flood in, and is accented with 8-foot doors and custom crown molding in the primary bedroom. The large primary bathroom features a walk-in shower, dual sinks, a dedicated toilet room, and access to the large walk-in closet with built in shelves, and enough room for a small crafts station. Additional highlights include two spacious guest bedrooms, elegant tile flooring throughout, and a two-car garage with a durable epoxy finish. Relax in your well-placed den with views of the natural preserve across the street or convert the space into a spacious home office. Outdoors, you can unwind in your private pool and enjoy the exquisite under-truss patio area. The electric roll-down screens and remote-controlled awning provide a perfect spot to relax poolside, savor the shade, and take in the tranquil lake views. The paver driveway has been widened and extended, while the pool deck pavers have recently been power washed and sealed for added appeal. The pie shaped lot is an added bonus giving you a large front yard and plenty of room between you and your neighbors. The conveniently situated lot location is not far from the resident's entrance, providing easy access in and out of the community. Winding cypress is conveniently located near shopping and dining options and is enveloped by 800 acres of natural preserve and 80 acres of stunning lakes. Winding cypress enhances the community experience with a wonderful dog park making it an ideal place for pet lovers this dedicated space allows residents and their furry friends to enjoy the outdoors socialize and stay active. Residents can avail themselves of various amenities, including the shady palm café, a resort-style pool and spa, a fitness center, social programs, and sports facilities such as pickleball, tennis courts, and bocce ball. There is also a walking trail for those who love to explore nature. This home exemplifies the essence of southwest florida living at its finest. Schedule a showing today. Be sure to click the full virtual tour links for details!

Winding Cypress, 7544 Winding Cypress Dr, Naples, Florida 34114, image 1

$830,000$320K

3 Beds
3 Baths
2,532 SqFt
$328/SqFt

House for sale in Winding Cypress7544 Winding Cypress Dr, Naples, FL 34114

Welcome to a beautiful pinnacle model in the desirable, amenity rich community of winding cypress. This waterfront home. Original owner care is apparent throughout. Builder and owner upgrades include; chef's kitchen with upgraded appliances, sink & faucet, soft close pull out cabinets including under-side lighting, custom quartz countertops, custom plank tile flooring, hurricane impact windows, slider, and entry door, upgraded & expansive lanai outdoor living area with storm smart kevlar screen enclosure & ready for you to design your own outdoor kitchen.

Winding Cypress, 7451 Blackberry Dr, Naples, Florida 34114, image 1

$885,000$64K

3 Beds
2 Baths
2,188 SqFt
$404/SqFt

House for sale in Winding Cypress7451 Blackberry Dr, Naples, FL 34114

Located in the highly sought-after community of winding cypress, this beautifully updated 3-bedroom, 2-bath home offers a perfect blend of luxury, comfort, and breathtaking lake views. Surrounded by 800 acres of natural preserve and 80 acres of serene lakes, this home provides a tranquil lifestyle immersed in nature, with access to all the incredible amenities this community has to offer. Inside, the open-concept layout features coffered ceilings in the living room, adding architectural elegance and a sense of spaciousness. Plantation shutters throughout enhance the light-filled spaces, creating an inviting and sophisticated atmosphere. The chef-inspired kitchen is equipped with a large walk-in pantry, perfect for all your storage needs, and flows seamlessly into the extended great room—ideal for both casual living and entertaining. The home also boasts a den with elegant french doors, providing a private and versatile space for an office, study, or cozy retreat. The large laundry room adds practicality and convenience, while the epoxy floor in the garage combines style and durability, creating a clean and functional space. Step outside to your own private oasis with an outdoor kitchen perfect for grilling and entertaining. The sparkling pool and hot tub, surrounded by a "no-see-um" screened enclosure, offer the perfect retreat with panoramic lake views. The lanai is equipped with hurricane storm screens for added peace of mind, and a whole-house generator ensures you’ll never be without power, even during the most unpredictable weather. Winding cypress is more than just a neighborhood; it’s a lifestyle. Residents enjoy access to the shady palm café, a spacious clubhouse, and luxurious resort-style amenities such as a pool and spa, fitness center, social programs, pickleball, tennis courts, bocce, and a scenic boardwalk walking trail. Surrounded by top-tier restaurants and grocery stores, and just a short drive to downtown naples, this community offers everything you need for both relaxation and convenience. Don’t miss your chance to own this exceptional home in one of the most desirable communities in the area.

Winding Cypress, 6848 Winding Cypress Dr, Naples, Florida 34114, image 1

$900,000

2 Beds
2 Baths
1,901 SqFt
$473/SqFt

House for sale in Winding Cypress6848 Winding Cypress Dr, Naples, FL 34114

The perfect move in ready home for sale! This summerwood floorplan features 2 bedrooms, 2 baths+den, saltwater pool and spa, and a 2+car garage offering a blend of style, comfort, and functionality. The open-concept layout features a dramatic zero-corner slider, seamlessly connecting indoor and outdoor spaces, while the whole home generator, exterior cameras, and impact windows and doors provide peace of mind. Inside, extensive upgrades are everywhere. The kitchen boasts built-in appliances and a spacious island, perfect for entertaining. Additional highlights include built-in sonos speakers, crown molding, hard flooring throughout, custom primary closet, and a murphy bed in the den—ideal for guests or a home office. The thoughtful laundry room has an upgraded washer and dryer and custom cabinets with a dedicated spot for charging your vacuum. You will have tons of storage space in the air conditioned tandem garage which can accommodate up to three cars. Outside, the saltwater pool and spa are heated by both gas and solar (a smart money-saving combo), expansive outdoor kitchen, hurricane screens for a second layer of protection, privacy lanai screening, plenty of seating areas, gorgeous lush landscaping, and areas for storage. This home has been meticulously maintained, most recently the duct work was cleaned and pavers sealed. Winding cypress is a natural gas community with resort-style amenities! Dine at shady palm, the onsite restaurant, or enjoy pickleball, bocce, tennis, a state-of-the-art fitness center, a resort-style pool, a community garden, and even a dog park for your furry friend. This pet-friendly community allows rentals, has low fees, and boasts a prime location—central to marco island, 5th avenue, and i- 75.

Winding Cypress, 7675 Winding Cypress Dr, Naples, Florida 34114, image 1

$1,255,000$244K

3 Beds
3 Baths
2,496 SqFt
$503/SqFt

House for sale in Winding Cypress7675 Winding Cypress Dr, Naples, FL 34114

Discover luxury living in this breathtaking pinnacle estate home, situated on one of the most coveted lakefront sites in the south naples resort community of winding cypress. Step inside to an open and spacious floor plan, enhanced by soaring tray ceilings, architecturally stunning alcoves and graceful arches. The home’s designer kitchen serves as the centerpiece, featuring every upgrade possible — soft-close cabinetry, quartz countertops, a fully vented natural gas range and hood and an all-premium kitchenaid appliance package with pull-outs in all lower cabinets. Adjacent is a large pantry complete with a water filter system for added convenience. The primary suite is a private oasis with towering ceilings and full walk-in shower and massive walk-in closet, while guest quarters include an expansive bay window en suite, ensuring comfort and privacy for family and friends. Additional living spaces include a versatile den or hobby room with upgraded french glass doors and foyer layout. Outdoor living is equally impressive. Relax by the saltwater pool and spa while enjoying serene wide-open lake views. Host gatherings with ease, thanks to a fully equipped outdoor kitchen featuring an integrated hood, all set within an expansive lanai with an upgraded oversized pocket slider door. The screened front porch, extended paver paths and custom landscaping further enhance the home’s curb appeal. Practical features include a 4-foot garage extension with custom flooring for three cars, all-impact glass windows, storm smart kevlar shutters and energy-efficient led lighting throughout. Additional upgrades include raised tray with crown-trimmed ceilings, a heated fireplace with customizable colors and custom state-of-the-art lighting systems that add a touch of sophistication to every room. Located in the resort-style community of winding cypress, residents enjoy exclusive access to a wealth of amenities, including a restaurant and bar, state-of-the-art fitness center, resort-style and lap pools, a spa and sports facilities for bocce, pickleball and tennis. The community also boasts a fire pit, bird-watching overlooks, a nature boardwalk and a picnic pavilion. Perfectly positioned between downtown naples and marco island, this home offers the ultimate in luxurious florida living. From its high-end finishes to its extraordinary location, it’s a property that truly has it all.

Winding Cypress, 7650 Jacaranda Ln, Naples, Florida 34114, image 1

$510,000$39K

2 Beds
2 Baths
1,579 SqFt
$323/SqFt

Villa for sale in Winding Cypress7650 Jacaranda Ln, Naples, FL 34114

Welcome to your dream home in the heart of one of naples' most sought-after communities! This stunning front entrance cressida villa offers the perfect blend of comfort, style, and convenience. Featuring two spacious bedrooms, two full baths, and a versatile den/flex room that can be used as an in-home office or guest area. The open concept living/dining space includes a custom-built dry bar/coffee station, light tile flooring, and sliders that open to a private screened lanai. The covered lanai area is plumbed for an outdoor kitchen, allowing you to create the perfect space for entertaining. Winding cypress offers a plethora of activities to enjoy the florida lifestyle.

Winding Cypress, 6906 Winding Cypress Dr, Naples, Florida 34114, image 1

$855,000$140K

3 Beds
3 Baths
2,124 SqFt
$403/SqFt

House for sale in Winding Cypress6906 Winding Cypress Dr, Naples, FL 34114

Built in 2022, this 2, 124-square-foot mystique model by divosta offers a rare turnkey opportunity, fully furnished with over $100, 000 in luxury personal property, including indoor and outdoor furniture, artwork, decor, cookware, bedding, and more. Virtually everything photographed is included, ensuring effortless move-in-ready elegance. The residence blends sophisticated design with functionality, featuring porcelain tile flooring, premium finishes, and custom furnishings throughout. The chef’s kitchen, a centerpiece, showcases two-tone cabinetry, a quartz island, and stainless-steel appliances, ideal for culinary enthusiasts. The open-concept living area flows to a screened lanai, where a heated saltwater pool and paver deck are framed by serene wilderness preserve views, perfect for relaxation or entertaining. The primary suite offers a spa-inspired bathroom with dual vanities and an expansive walk-in closet. Practical features include hurricane storm protection, a spacious laundry room with built-in storage, and a two-car garage. Dramatic landscape lighting adds vibrant depth to the exterior, enhancing curb appeal and creating a refined nighttime ambiance. This meticulously crafted home elevates modern luxury with timeless comfort. This 3-bedroom, 3-bathroom residence, complete with a den, balances elegance and practicality. The two guest bedrooms, each with full bathroom access, ensure privacy and comfort. The den, ideal as a home office, features built-in shelving and natural light. The great room, with 10-foot ceilings and large windows, frames tranquil preserve views. Smart-home technology, including automated lighting and climate control, enhances efficiency. The heated saltwater pool, with a sun shelf and lighting, and the paver deck with manicured landscaping, create a refined outdoor retreat. Upgraded fixtures, such as rainfall showerheads in the primary bathroom and recessed lighting throughout, elevate the home’s sophisticated aesthetic. The exterior features low-maintenance tropical landscaping, complementing the preserve backdrop. Nestled in the gated winding cypress community in southeast naples, this home is part of a prestigious enclave of 766 residences. Spanning 800 acres of preserves and 80 acres of lakes, winding cypress blends natural beauty with luxury. Residents enjoy low hoa fees and amenities, including a resort-style pool with cabanas, a fitness center with modern equipment, and courts for pickleball, bocce, and tennis. The clubhouse, a social hub, offers an internet café, event spaces, and a catering kitchen. A dog park, community garden, and trails through lush preserves cater to diverse lifestyles. Located minutes from marco island’s beaches, naples’ vibrant 5th avenue, and i-75, this home ensures access to fine dining, shopping, and cultural attractions. Winding cypress offers a close-knit community, making this turnkey home a standout in naples luxury living.

Winding Cypress, 7686 Jacaranda Ln, Naples, Florida 34114, image 1

$453,000$122K

2 Beds
2 Baths
1,574 SqFt
$288/SqFt

Villa for sale in Winding Cypress7686 Jacaranda Ln, Naples, FL 34114

Don’t miss this exceptional opportunity to own an upgraded cressida villa in the sought-after community of winding cypress! This front-entry home lives like a single-family residence, offering 2 bedrooms + den, 2 bathrooms, a 2-car garage, and a stunning expanded patio with extra covered space—more than most villas. Inside, enjoy luxury upgrades including white cabinetry, quartz countertops, crown molding, and more. The outdoor space is equally impressive, featuring a built-in hood for effortless grilling and gorgeous mature landscaping. Winding cypress is a natural gas community with resort-style amenities! Dine at shady palm, the onsite restaurant, or enjoy pickleball, bocce, tennis, a state-of-the-art fitness center, a resort-style pool, a community garden, and even a dog park for your furry friend. This pet-friendly community allows rentals, has low fees, and boasts a prime location—central to marco island, 5th avenue, and i-75.

Winding Cypress, 7530 Geranium Way, Naples, Florida 34114, image 1

$975,000$200K

3 Beds
3 Baths
2,496 SqFt
$391/SqFt

House for sale in Winding Cypress7530 Geranium Way, Naples, FL 34114

This home is an amazing value for winding cypress!! Once you compare, you'll agree. The pinnacle model is clearly the most popular floorplan in the community. The sought after "open area concept" footprint boasts 3 expansive bedrooms including a most impressive owner's suite, 3 full baths, a large den, desirable 3 car garage, and 2496 square feet of indoor living space under air. Builder and owner upgrades include an executive waterfront premium lot, kitchen appliance package, pool with new heater integral spa, quartz counters, upgraded cabinet package, den/office, zero corner sliding glass doors, plank tile flooring, plumbed for a summer kitchen, inviting lead glass front entry door.

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2 – 4 BR

Bedrooms

2018

Year Build

Total Floors

Subdivision Amenities

Bike And Jog Path

Bocce Court

Business Center

Cabana

Clubhouse

Community Room

Dog Park

Fitness Center

Hobby Room

Internet Access

Library

Park

Pickleball

Play Area

Pool

Private Membership

Restaurant

Shuffleboard Court

Sidewalk

Spa/Hot Tub

Streetlight

Tennis Court(s)

Underground Utility

Barbecue

Bike And Jog Path

Bocce Court

Clubhouse

HOA Cost Benchmark

This Community

$0.24

Comparable Mid-Tier Avg

$0.16

Naples, FL Avg

$0.29

$0.00

$0.18

$0.35

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Azure At Hacienda Lakes, 9209 N Cayman Dr, Naples, Florida 34114, image 1

$565,000$34K

Villa for sale in Azure At Hacienda Lakes9209 N Cayman Dr, Naples, FL 34114

Azure At Hacienda Lakes, 9225 Cayman Dr, Naples, Florida 34114, image 1

$599,900

Villa for sale in Azure At Hacienda Lakes9225 Cayman Dr, Naples, FL 34114

Azure At Hacienda Lakes, 8966 Saint Lucia Dr, Naples, Florida 34114, image 1

$529,000$60K

Villa for sale in Azure At Hacienda Lakes8966 Saint Lucia Dr, Naples, FL 34114

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3300 Gulf Shore Naples

Condos in Naples, FL 34103

Starts at
$3M
Units
51
Stories
8

3300 GULF SHORE NAPLES' MOST Anticipated Waterfront Address

Perfectly positioned between the Gulf of Mexico and Outer Doctors Bay, these exclusive residences redefine coastal luxury with dual water views, private boat docks, and effortless access to downtown Naples. Each residence captures the essence of Gulf Shore Blvd living; serene, sophisticated, and distinctly Naples.

Crafted for discerning homeowners seeking both refinement and ease, 3300 Gulf Shore offers expansive floor plans, modern architecture, and world-class design. Every detail from panoramic glass walls to designer finishes celebrates waterfront tranquility. Enjoy private lobbies, concierge services, and exclusive marina access just steps away.

Located minutes from 5th Avenue and 3rd Street South, 3300 Gulf Shore connects residents to Naples’ finest dining, culture, and boutiques while maintaining the calm of a private coastal retreat. Enjoy the best of both worlds, sophisticated downtown proximity and the peaceful rhythm of the bay. Discover the rare opportunity to own along Gulf Shore Blvd. Complete the form below to request floor plans, availability, and exclusive details about Naples’ premier new waterfront condominium community.

Discover the art of coastal living at 3300 Gulf Shore, a boutique collection of waterfront condos in Naples, Florida. Each residence is designed with open-concept layouts, private outdoor terraces, and refined interior finishes that blend luxury and livability. Explore detailed floor plans to find your perfect retreat; from elegant two-bedroom residences to expansive Gulf-view penthouses.

RESIDENCE Features

Expansive 51 Two- to Five-Bedroom Residences
Residences from 2,000 to 7,500 sq. ft.
Seamless Indoor and Outdoor Living
Gracious Terraces with Panoramic Views
Residences Overlooking the Bay and Gulf
Outdoor Gas Grills with Dining Areas on Terraces
Ceiling Heights up to 11 ft. in Main Living Areas & Owner’s Suite
Sub-Zero and Wolf® Panel-Ready Appliance Suite
Oversized Kitchen Island with Cascading Stone Waterfall Edge
Custom Luxury European-Style Cabinetry
Dornbracht® Rainfall and Hand Shower with Built in Floating Bench
Spa-Inspired Baths with Soak Tubs and Toto® Neorest bidet toilets

At 3300 Gulf Shore, every detail has been curated for an effortless waterfront lifestyle. Residents enjoy a private marina on Outer Doctors Bay with 16 boat slips, a sunrise resort-style pool with lap lane, and direct access to paddleboarding and waterfront recreation.

3300 WELLNESS CLUB

A spa terrace with cold plunge and daybeds is complemented by a state-of-the-art fitness center, flexible training and yoga spaces, a multisensory experience shower, steam and sauna rooms, and a private treatment suite designed for restoration. Just steps away, a second resort-style pool awaits on the sunset terrace, surrounded by serene lounge seating.A spa terrace with cold plunge and daybeds is complemented by a state-of-the-art fitness center, flexible training and yoga spaces, a multisensory experience shower, steam and sauna rooms, and a private treatment suite designed for restoration. Just steps away, a second resort-style pool awaits on the sunset terrace, surrounded by serene lounge seating.

CONCIERGE & SERVICES

Designed for relaxation and connection, the marina-front lounge features outdoor trellis seating, summer kitchen, and private dining rooms with a chef’s catering kitchen. Residents can unwind in the exclusive club lounge and tasting bar or host gatherings overlooking Venetian Bay.

AMENITIES & Services

Private lobbies in each tower
On-site property management services
24-hour front desk concierge
Mail room and delivery services
Private marina on Outer Doctors Bay with 16 boat slips
Watersport launch for paddle boarding and waterfront activities
Sunrise resort-style pool with lap lane overlooking the marina
Marina front lounge and trellis for entertaining
Outdoor lounge with a summer kitchen, lounge & dining seating
Residents-only bar, club kitchen, and lounge with tasting table
Private dining or conference room with chef’s catering kitchen
Sports and gaming lounge with multi-sports simulator
Stylish and well-appointed game and card room
Hospitality station providing water and coffee daily

Details

Encore At Naples Square

Condos in Naples, FL 34102

Starts at
$3.6M
Units
15
Stories
3

Details

Epique At Pelican Bay

Condos in Naples, FL 34108

Starts at
$6.5M
Units
68
Stories
19

Celebrated as one of the most desirable residential communities in Florida, Pelican Bay, in Naples, is a sophisticated and cosmopolitan enclave lined by pristine sugar-sand beaches framed by the gentle currents of the Gulf of Mexico. Epique Pelican Bay is ideally positioned to offer the most spectacular waterfront and sunset views.

Epique Pelican Bay offers residents a rarified and all-encompassing lifestyle on the Gulf. Enjoy a host of sporting amenities including tennis, boating, paddleboarding, canoeing and biking surrounded by 88 acres of parks and recreation. As a resident of Pelican Bay, owners have access to chauffeured golf cart beach tram service and the opportunity to join Club Pelican Bay with 27 holes of championship golf.

Every service. Every amenity. Delivered to Epique owners flawlessly. From the Private Dining Club to the full floor of indoor and outdoor social and wellness amenities, Epique is dedicated to addressing the needs of every resident. The concierge oversees the wealth of benefits and opportunities available to the 68 owners, including 24/7 staffing and monitoring, greeting residents and guests, and offering a suite of conveniences.

The beautifully landscaped Pool Deck, surrounded by lush tropical foliage, is an inviting retreat for exercise or relaxation. Reinvigorate with laps or luxuriate on a chaise lounge. Enhance your rejuvenation with a private training session in the Health and Fitness Club or wind down in the adjacent steam room.

Stone and wood-paneled galleries, displaying a significant art collection, lead to an impressive array of thoughtful amenities. Business meetings and social gatherings can take place in the Board Room or Salon. The Club Room, Card Room/Solarium, state-of-the-art Private Screening Room, Golf Simulator and Game Room provide inviting escapes. The professionally equipped Health and Fitness Club overlooks the landscaped Pool Deck.

The Private Dining Club allows residents to entertain effortlessly. Exclusively reserved for Epique owners and their guests, the impressively designed indoor and outdoor spaces offer masterful mixology, inspired menus and a private room that can be reserved for intimate events.

Soaring 19 stories above Pelican Bay, Epique offers the best views in Naples. The striking façade is encased in floor-to-ceiling windows capturing the technicolor splendor of the sunsets over the Gulf.

The grandly scaled Estates, which range in size from 4,001+/- to 5,213+/- air conditioned square feet, offer a level of bespoke finishing and detailing that raises the benchmark in Naples. Estates feature 10’ ceiling heights and a SmartEstate™ integrated home technology system.

The four Penthouse residences will be the most prized and desired residences in Naples. Designed for expansive entertaining, the homes are richly appointed in millwork and the finest finishes with elevated 12-foot ceiling heights. Each Penthouse offers a private resort-style rooftop pool deck overlooking the Gulf.

Details

Olana Naples Residences

Condos in Naples, FL 34102

Starts at
$30M
Units
12
Stories
6

Olana introduces a limited collection of twelve estate scale residences on one of the most coveted stretches of Gulf Shore Boulevard in Naples. The property combines direct Gulf frontage, expansive architectural volume, and a private residential experience shaped for a discerning global audience. This is a place designed for long term significance, quiet sophistication, and a level of beachfront exclusivity rarely seen in Southwest Florida.

The design of Olana reflects a studied balance of modern coastal architecture and refined interior living. Every line, proportion, and material choice is shaped to enhance light, privacy, and the connection to the Gulf. The architectural and interior elements work together to create spaces that feel both contemporary and enduring, with scale and detail that support a true estate level living experience.

Olana’s residences offer the space and exclusive amenities to create the experience of life in a mansion, but beautifully suspended in the sky. Owners arrive via private elevator either from the lobby or from their individual parking garage. An expansive wellness suite with spa and fitness features brings well-being home.

CHEF KITCHENS INCLUDE PROFESSIONAL-GRADE STAINLESS STEEL CABINETRY AND COUNTERTOPS AS WELL AS SUB-ZERO® AND WOLF® APPLIANCE SUITE
CLIMATE-CONTROLLED WINE ROOM WITH GLASS-ENCLOSED DISPLAYS
CUSTOMIZED WET BAR WITH BUILT-IN UNDER-THE-COUNTER SUB-ZERO® BEVERAGE CENTER AND ICE MAKER FOR ELEGANT ENTERTAINING
GLASS-ENCLOSED FIREPLACE CONNECTING THE GREAT ROOM
FITNESS CENTER WITH CUSTOM RESISTANCE FLOORING DESIGNED FOR FITNESS EQUIPMENT, PERFECT FOR CORE, PILATES, AND WEIGHT TRAINING
WELLNESS CENTER WITH A FULL HYDROTHERAPY SUITE
OWNER’S SUITES INCLUDE DUAL WALK-IN CLOSETS AND LUXURIOUS SPA-LIKE RETREATS
THEATER ROOM FEATURING ACOUSTICALLY DESIGNED WALLS FOR SUPERIOR SURROUND SOUND
TECHNOLOGY-READY INFRASTRUCTURE FOR EASY-OWNER CUSTOMIZED HOME AUTOMATION

Details

Palazzo At Bayfront

Condos in Naples, FL 34102

Starts at
$1.7M

This is it – the rare opportunity to live where the pulse of downtown Naples meets the privilege of a waterfront community lifestyle. With only 35 luxury condominiums available, Palazzo Bayfront Naples is a rare opportunity to surround yourself with everything the most livable city in America has to offer, right here in Florida.

Palazzo Bayfront Naples stands at the gateway to the iconic 5th Avenue South. Stepping outside your door offers immediate access to world-class dining, designer shopping, captivating art galleries, and stunning natural beauty. Palazzo’s luxury condominiums also sit just steps away from the newly opened Gulfshore Playhouse.

Palazzo’s resort-style amenities provide exactly what residents need to enjoy a relaxed and walkable Naples lifestyle. From the tropical oasis of the pool deck to the intimate clubhouse space, every detail ensures a refined lifestyle that feels like an endless vacation.

Palazzo Bayfront Naples will feature 35 spacious condominiums highlighted by the latest innovations and exquisite finishes. Every residence features three bedrooms and extraordinary designer touches that exceed expectations. Private terraces invite residents to unwind and enjoy the indoor/outdoor Florida lifestyle in style.

Featuring four unique floor plans ranging from 2,100 to over 3,100 total square feet, this assortment of elegant residences combines waterfront living with downtown offerings like never before.

Each condominium has been designed with three bedrooms and three bathrooms and offers spa-like amenities, top-of-the-line finishes and convenient covered parking as you enjoy the shops, restaurants and entertainment steps from your front door.

Palazzo perfectly embodies the Naples Bay waterfront lifestyle with amenities designed for ultimate enjoyment. Residents of this pet-friendly community will relish the uniqueness of Palazzo’s location, within easy reach of Bayfront’s excitement, yet set in a more tranquil private setting. Here, every day feels like a vacation getaway.

The resort-style pool and spa are ideal for relaxing in true Florida fashion. Surrounded by inviting cabanas and comfortable loungers, this oasis is ideal for lounging or enjoying a good book. Outdoor barbecue areas invite residents to savor delicious meals with friends and family in a relaxed setting.

The poolside clubhouse serves as a sophisticated social hub for residents. With inviting lounging spaces, it’s the perfect place to celebrate sunset with friends before embarking on a memorable evening out. The indoor chef’s kitchen is ideal for entertaining and creating engaging experiences with neighbors.

The Fitness Room offers all the essentials to enhance your wellness journey from cardio workouts to strength or stretch training. Whether residents aim to build strength, boost endurance, or maintain an active lifestyle, this well-equipped space makes it effortless to prioritize health from the comfort of home.

Palazzo’s standout amenity is its unbeatable location, with everything you need just steps away. Bayfront Naples offers residents a vibrant selection of shopping, dining, and design services, all surrounded by its private marina lifestyle.

Boat slips for the on-site marina are available for Palazzo residents, providing direct access to Naples Bay and the Gulf of Mexico. Boating enthusiasts can join the Freedom Boat Club for easy boat reservations for sunset cruises, fishing trips, or day outings. Ready for something more invigorating, venture out on a kayak or paddle board to explore the local waterways.

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Park Place On Gulf Shore

Condos in Naples, FL 34102

Starts at
$7.5M
Units
15
Stories
4

Park Place On Gulf Shore
Luxury Condos With Beach-to-Bay Views in Naples, FL
Once described as "a beautiful little city on the west coast of Florida," Naples has emerged from a tiny fishing village home for esteemed winter residents to a modern coastal city alive with arts, culture, recreation and the best beaches in Southwest Florida. Park Place on Gulf Shore presents a rare opportunity to become part of the small enclave of luxury condominiums along the famed Gulf Shore Boulevard and the only one offering beach-to-bay "thru" views.

The Naples Lifestyle
Park Place on Gulf Shore is poised to present an unparalleled lifestyle amidst the captivating backdrop of Southwest Florida. Perfectly positioned along the tranquil bay, this enclave provides a haven for water enthusiasts with the added luxury of private boat slips.

Proximity to acclaimed dining and upscale boutique shopping destinations such as Venetian Village, Waterside Shops, Fifth Avenue South and Third Street South solidifies its status as one of the most exclusive developments in the area.

With a myriad of white sand beaches, just steps from these luxury condominiums, residents and their guests will certainly enjoy all the nearby tropical offerings Naples has become famous for.

A Sophisticated Resume
Led by prestigious developers Golub & Company and Barron Collier Companies, Park Place on Gulf Shore is expected to exceed all expectations for the luxury condominium market. Building upon their illustrious track record of past achievements, this development promises to set a new benchmark for excellence.

Crafted with meticulous attention to detail, Park Place on Gulf Shore will feature 15 exclusive residences, each with breathtaking views of the Gulf of America and Moorings Bay. Here, you will discover a luxury living experience in a location that stands unrivaled.

Park Place on Gulf Shore will boast two eye-catching mid-rises with luxurious amenities including a bayfront pool and pool deck, private boat slips, hospitality-inspired rooftop bar and seating areas, fire pit, under building parking, storage areas and much more.

For the utmost in elegance and privacy, Park Place on Gulf Shore’s luxury condominiums will feature six exceptional residences across three floors, in the west building, and in the east building, nine equally impressive residences, also across three floors. Each condominium will also have direct elevator access. With 10’ ceilings, luxury finishes and boat slips available, Park Place on Gulf Shore will indeed offer elegance from floor to ceiling.

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Rosewood Residences Naples

Condos in Naples, FL 34102

Starts at
$12.8M
Units
42
Stories
7

Rosewood Residences Naples is a luxurious destination that exudes sophistication and elegance. Our beachfront residences provide a premium luxury experience with refined interiors and abundant amenities surrounded by lush tropical foliage with direct access to pristine beaches. And with Naples’ internationally renowned golf courses, upscale designer shopping, world-class art galleries, exceptional culinary offerings, and enticing outdoor excursions to soak up the region’s natural beauty, there is always more to discover and experience.

Indulge in a wealth of luxurious amenities. Exceptional indoor and outdoor facilities offer the perfect blend of tranquility and entertainment, a hallmark of the Rosewood Enriched Living experience. All residents and their guests have exclusive access to a sun deck with resort-style pool, zero-edge lap pool, multiple spas and shaded areas, terrace, game rooms, lounges and more. At Rosewood Residences Naples superior accommodations, amenities and services are always within reach.

Created in collaboration with the esteemed and favored developer in Southwest Florida, Ronto Group, Rosewood Residences Naples is the epitome of beachfront living perfected. Surrounded by white sandy beaches, turquoise blue waters, lush vegetation and an oasis of premium resort-style amenities, every day is filled with luxurious possibilities.

At A Glance

42 private residences with unobstructed Gulf of Mexico views
Beachfront access at multiple entry points
Elegant and elevated interior design by Lillian Wu Studio, NYC
Spacious floor plans and private terraces
Lush landscaping throughout the property and amenities deck
Resort-level outdoor amenities deck plus stylish indoor lounges and social spaces
Exceptional feature and finishes selections

Arrival Experience

Porte cochère with valet services for residents and guests
Enchanting commissioned sculpture of polished steel
Graceful framing of lush coconut palms and fragrant wax jasmine upon entry
Grand staircase and custom chandelier in main lobby
Secure access to one private and one service elevator per residence

Building Features

Gated entry
Controlled perimeter access
24/7 security
Parking spaces with 40 amp power: two spaces for typical units, four spaces for penthouse units
Association-owned golf carts
Bicycle storage
Long term storage

Details

The Ritz-Carlton Residences Naples

Condos in Naples, FL 34108

Starts at
$4.8M
Units
128
Stories
12

A Once-In-A-Lifetime Address

From the very first moment you encounter The Ritz-Carlton Residences, Naples, it is clear this is a destination that transcends the typical coastal lifestyle. Here, the gulf is yours like never before with a prestigious marina-front location that also overlooks one of the most beautiful beaches on Florida’s west coast. This boutique collection of 128 residences is made all the more desirable by spacious layouts, captivating seaside and sunset views, a secluded park, and The Vanderbilt Club — a 28,000-square-foot residents’ retreat. It is a one-of-a-kind lifestyle made even more rewarding with the legendary service of The Ritz-Carlton.

Sophisticated Enjoyment in Every Moment

Welcome to a world where all you love is at your fingertips. A private library, upscale restaurant with water views, coffee lounge, theater room, golf simulator, billiards and game room, and business café are just a few of the many options available at the Clubroom. Outdoors, an elevated terrace, pool with sun shelf, jetted spa, cabanas, a putting green, covered grilling areas, a secluded neighborhood park, and full-service marina await. Special areas are devoted to children and teens, fitness, pets, and sensory relaxation. If it brings you joy, you’ll find it at The Ritz-Carlton Residences, Naples.

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