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Winding Cypress Houses For Sale

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Ultra Luxury — Above $1,000 per SqFt
High-End — $650 - $1,000 per SqFt
Mid-Tier — $400 - $650 per SqFt
Premium — $300 - $400 per SqFt
Entry-Level — Below $300 per SqFt
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Building with 1- 4 floors
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Results 12 of 12
Winding Cypress, 6825 Greenbriar Ct, Naples, Florida 34114, image 1
$965,000
  • 4 Beds
  • 3 Baths
  • 3,036 SqFt
  • $318/SqFt
Premium
House for sale in Winding Cypress
6825 Greenbriar Ct, Naples, FL 34114
Preserve views on a quiet cul-de-sac street define this two-story mystique residence in winding cypress, where a saltwater pool with spillover spa, expansive outdoor living and flexible interior spaces create a home designed for relaxation and entertaining. With four bedrooms, a den, an upstairs flex room, three baths and a two-car garage, the floor plan offers exceptional versatility while maintaining an open, connected feel throughout the main living areas. A whole-house generator is on-site, providing added peace of mind during storm-related power outages. A brick paver driveway, tile roof and professional landscaping establish a polished arrival. Inside, wood-look tile flooring, recessed lighting and white plantation shutters carry a clean, cohesive aesthetic throughout the home. The living room is filled with natural light from five windows and anchored by a modern ceiling fan, while the adjacent dining area draws additional light through its windows and sliding glass door, creating an easy transition between indoor and outdoor spaces. Open to the living and dining areas, the kitchen serves as the center of the main level with white shaker-style cabinetry, quartz countertops and a designer marble tile backsplash. A three-seat island provides a natural gathering place, complemented by stainless steel gas cooking appliances and a pantry. Positioned just off the kitchen, the primary suite offers a private retreat with a tray ceiling, walk-in closet and well-appointed en-suite bath. A dual-sink white vanity provides generous preparation space, while the floor-to-ceiling tiled walk-in shower features a built-in bench. A dedicated linen closet adds further storage. Additional guest bedrooms and baths provide comfortable accommodations, while a downstairs den with french doors creates a quiet setting for work or study. Upstairs, the carpeted flex room expands the home’s versatility and can readily serve as a media room, fitness space, office, playroom or secondary lounge. The upstairs bedroom and full bath create a private retreat that is especially well suited for extended family or out-of-town guests, offering added separation and privacy from the main living areas. Outdoors, a covered living area with paver flooring overlooks the screened saltwater pool and spillover spa, both framed by brick pavers. Beyond the pool enclosure, the home backs to a preserve and small creek, providing a natural backdrop and an added sense of privacy. Residents of winding cypress enjoy access to a private clubhouse with year-round gatherings, live music, holiday events and community activities. Ideally between downtown naples and beaches of marco island, this residence combines preserve-side privacy, substantial indoor-outdoor living, flexible accommodations and the added security of a whole-house generator in one of southwest florida’s well-established communities.
Winding Cypress, 7666 Jacaranda Ln, Naples, Florida 34114, image 1
$575,000
  • 2 Beds
  • 2 Baths
  • 1,574 SqFt
  • $365/SqFt
Premium
Villa for sale in Winding Cypress
7666 Jacaranda Ln, Naples, FL 34114
Experience elevated resort-style living in the highly desirable community of winding cypress. This impeccably maintained and tastefully updated 2-bedroom plus den, 2-bath villa offers soaring 9’4” ceilings and an attached two-car garage, delivering both comfort and functionality in a truly move-in-ready residence. Thoughtful upgrades include a newer refrigerator and hot water heater, upgraded pavers, plantation shutters, and additional enhancements that add both style and peace of mind. The flexible den provides the perfect space for a home office, guest retreat, or additional lounge area. Winding cypress is designed for those who value lifestyle. Nearly two-thirds of the community is preserved as tranquil natural landscape and wooded conservation, creating a serene, private atmosphere rarely found this close to everything. Ideally located just 8 miles from downtown naples and 9 miles from marco island, you are moments from world-class dining, shopping, and gulf beaches. Residents enjoy an impressive amenity package featuring pickleball, bocce, clubhouse, resort-style pool and spa, community park, social rooms, and more. Opportunities like this are rare. Schedule your private showing today.
Winding Cypress, 7602 Jacaranda Ln, Naples, Florida 34114, image 1
$579,000
  • 2 Beds
  • 2 Baths
  • 1,554 SqFt
  • $373/SqFt
Premium
Villa for sale in Winding Cypress
7602 Jacaranda Ln, Naples, FL 34114
**motivated sellers!! This freshly painted, light-filled attached villa in winding cypress features two bedrooms plus a den with easy conversion to a third bedroom, two full bathrooms, and a two-car garage. An open floor plan, bright kitchen with stainless-steel whirlpool appliances, granite counters and an in-residence laundry room with a newer washer and dryer make everyday living comfortable. A newly screened lanai overlooks a very private backyard, creating a relaxing setting.Winding cypress offers an exceptional collection of resort amenities, including a resort-style pool and spa, poolside restaurant, attended fitness center, yoga lawn, outdoor fireplace, five tennis courts, eight pickleball courts, and four bocce courts. Explore the nature boardwalk and walking paths, community garden, visit the covered dog park, or enjoy an active calendar of social events. This home has 100% hurricane coverage. Conveniently located between downtown naples and marco island, this home provides easy access to white-sand beaches, fifth avenue shopping and dining, and i-75. Make the southwest florida lifestyle your own. Furnishings negotiable!
Winding Cypress, 7156 Live Oak Dr, Naples, Florida 34114, image 1
$590,000$10K
  • 3 Beds
  • 2 Baths
  • 1,554 SqFt
  • $380/SqFt
Premium
Villa for sale in Winding Cypress
7156 Live Oak Dr, Naples, FL 34114
Price alert- this is the lowest true 3-bedroom complete with your own private pool located in the amenity rich community of winding cypress!!! The ultimate blend of luxury, comfort, and effortless living is turnkey ready for your immediate enjoyment. The 2-car attached garage—complete with convenient overhead storage racks and additional utility sink—offer great convenience. Discover a bright, open-concept living space featuring seamless tile flooring throughout. The spacious great room flows effortlessly into your own private outdoor oasis. The enlarged screened lanai offers you enjoyment of a private pool and outdoor grill kitchen, located on a exceptionally private lot that offers a serene, peaceful retreat for relaxation or entertaining. The owner’s suite serves as a tranquil escape, boasting elegant tray ceilings and an ensuite bath complete with a dual-sink vanity, a walk-in shower, a linen closet, and a generous walk-in closet. Two additional bedrooms provide ample space and privacy for visitors and guests. Key upgrades and features include: new hvac unit for year-round comfort and energy efficiency. Storm smart electric storm shutters on the rear lanai. Accordion shutters on all exterior windows for ultimate peace of mind and storm protection. Winding cypress is renowned for its world-class amenities, including a resort-style pool, a resident-only restaurant, pickleball, tennis, bocce, a state-of-the-art fitness center, two dog parks, and a vibrant social calendar. Perfectly positioned just minutes from the award-winning beaches of both naples and marco island, as well as shopping, dining, and entertainment, this property is an ideal choice for a full-time residence, a seasonal retreat, or a savvy investment option. Don't miss this rare opportunity to live the florida dream!
Winding Cypress, 7670 Jacaranda Ln, Naples, Florida 34114, image 1
$625,000
  • 3 Beds
  • 2 Baths
  • 1,594 SqFt
  • $392/SqFt
Premium
Villa for sale in Winding Cypress
7670 Jacaranda Ln, Naples, FL 34114
Escape cookie-cutter living at 7670 jacaranda, where custom millwork, extensive built-ins and thoughtful upgrades give this 2018-built home a character all its own. The open kitchen anchors the main living area with upgraded samsung smart appliances, natural gas range, custom built-in coffee bar, sleek cabinetry and quartz counters, flowing naturally into the dining and living spaces. High ceilings with crown molding and transom windows create a light and bright interior with the utmost in privacy. The living room features a custom entertainment wall with fireplace and built-in cabinetry for a striking focal point. The attention to detail continues into the primary suite, where a dramatic ceiling treatment adds architectural interest and a spacious bath with dual vanities and an oversized glass-enclosed shower. The custom walk-in closet is beautifully finished with extensive cabinetry, drawers, shelving and hanging space. Additional bedrooms are sunny and inviting, while a dedicated laundry room adds excellent storage and everyday functionality. Handcrafted storage options have been thoughtfully tucked in throughout the residence, allowing the square footage to live large. Outside, the home shifts seamlessly into florida living. The expansive screened lanai surrounds a sparkling gas-heated saltwater pool with a cascading water feature and generous space for lounging and entertaining, while the covered outdoor living area with built-in outdoor kitchen creates a true extension of the interior. Beyond the enclosure, find a lush and private yard with mature landscaping for additional green space and privacy. The attached two car-garage is fully insulated with built-in shelving and an expanded attic space for even more storage, plus two 15-amp circuits, making it a breeze to add ev charging. Winding cypress is a unique guarded and gated community with an emphasis on natural spaces, thanks to over 800 acres of natural preserves alongside 80 acres of lakes, all adjacent to the picayune strand state forest. The community's wooden boardwalk is perfect for morning walks and birdwatching or visit the extensive amenities center anchoring the neighborhood. There you'll find a resort-style pool and spa, state-of-the-art fitness center, tennis, pickleball and bocce courts, dog park, walking and biking opportunities and the popular shady palm cafe for casual dining and drinks close to home. An active social calendar and inviting gathering spaces create plenty of opportunities to connect, while the community’s preserve setting gives it a peaceful, distinctly florida feel. Thoughtfully customized, impeccably maintained and surrounded by the natural beauty of winding cypress, 7670 jacaranda offers a distinctly different take on naples living.
Winding Cypress, 7247 Clamshell Ln, Naples, Florida 34114, image 1
$1,549,000
  • 4 Beds
  • 4 Baths
  • 3,656 SqFt
  • $424/SqFt
Premium
House for sale in Winding Cypress
7247 Clamshell Ln, Naples, FL 34114
A must-see home in a must see community extensive upgrades and designer elements elevate this home, based on an award winning model. Gorgeous water/preserve views are seen both back and front. This quiet, lush green street is just a short walk to the recreation center where several activities, amenities and social events can be enjoyed. Winding cypress has low hoa fees, numerous inclusions and is full of natural beauty. Motivated seller. All of which make this a must-see home and community. Inside, beautiful design blends elegance with functionality. The roomy open floor plan is ideal for easy mingling but has plenty of private spaces for everyday life. Enter a spacious foyer leading to the great room. Here, defined living and dining areas border a showpiece kitchen with a huge 10-foot island, gas cooking and a walk-in pantry, enhanced by several upgrades such as premium cabinetry and appliances, quartz countertops, generous crown molding and wainscoting, upgraded porcelain tile flooring, custom lighting and other designer finishes. Zero-corner doors enable fabulous indoor-outdoor entertaining, opening up the house to a beautiful lanai which has uncommon, high-impact, structural upgrades. It is oversized/extended to create a wide open feel and multiple spaces for relaxing and entertaining. The pool with spa and baja shelf is also oversized for daytime full family fun and a dramatic lit atmosphere at night. The picture-frame screen enclosure is yet another upgrade for best showcasing the stunning views of water, preserve and large flocks of birds in winter. The ground floor primary suite offers a private retreat with a poolside bedroom, spa-like bathroom, coastal design enhancements and large walk-in closet. This floor also has two more bedrooms, each with a walk-in closet, and a den that can be used as a study, sitting room, tv room, or flex space. Upstairs is a large bedroom that comfortably sleeps up to 6 people; a full bath and a huge 34x21 loft that can be used as a quiet home office, fitness room, media room or play area for example. The floor plan has lots of storage and works well for a variety of lifestyles/needs like hosting large family gatherings, working from home, or multigenerational living. Other upgrades include full impact glass, an oversized, shelved, three vehicle garage with epoxy flooring. This home is situated on one of the most desirable, tranquil lots and is a one owner home. Winding cypress has a guard-gate, all landscaping and a wow amenity center included in the low hoa, as are pickleball, tennis, bocce, fitness center, resort-style pool, on-site restaurant and bar, dog park, scenic walking trails and a full schedule of entertainment and social activities—providing a resort style country club lifestyle without country club fees. It is just minutes to marco island, downtown naples, beaches, boating, golf, shopping, restaurants, hospitals, i-75.
Winding Cypress, 7700 Winding Cypress Dr, Naples, Florida 34114, image 1
$1,250,000
  • 5 Beds
  • 3 Baths
  • 2,950 SqFt
  • $424/SqFt
Premium
House for sale in Winding Cypress
7700 Winding Cypress Dr, Naples, FL 34114
Beautiful and meticulously maintained 5 bedroom, 3 bath home in divosta’s gated winding cypress community, one of naples most desirable locations, convenient to downtown naples, marco island’s pristine beaches as well as nearby shopping and restaurants, this summerwood floorplan features a master on main living floor with large bath and walk-in closet, a large loft space upstairs with a separate bedroom and full bath, and 3 other bedrooms and bath on the main living level. Numerous upgrades include oversized pool and spa, extended lanai and garage, zero corner sliding doors leading to lanai, framed drop soffit in master, floor outlet, decorative glass front door, oversized kitchen island, outdoor kitchen with built-in grill and cooler, tankless water heater, and custom cabinetry and tile. Winding cypress features a gated entrance with guard, dog park, community garden, tennis, pickleball, beautiful clubhouse with bar and grill, large resort pool and decks…truly a gem in south naples! And no flood insurance required!!
Winding Cypress, 7072 Live Oak Dr, Naples, Florida 34114, image 1
$1,450,000
  • 4 Beds
  • 4 Baths
  • 3,350 SqFt
  • $433/SqFt
Premium
House for sale in Winding Cypress
7072 Live Oak Dr, Naples, FL 34114
Welcome to this beautifully appointed 4-bedroom, 4-bath residence offering approximately 3, 350 square feet and a custom, one-of-a-kind floor plan not found elsewhere in the community. Designed for effortless florida living, the spacious interior features multiple living and dining areas, a private office, elegant architectural details and an impressive kitchen with white cabinetry, a large island and abundant workspace. A built-in wine bar adds the perfect touch for entertaining. Expansive sliders open to a screened lanai with an outdoor kitchen, private pool and spa, fire pit and peaceful water views. Additional highlights include generously sized bedrooms, well-appointed baths, a walk-in closet, separate laundry room and attached garage. Located in a sought-after natural gas community with beautiful surroundings and resort-style amenities, this exceptional home combines custom design, comfort and the indoor-outdoor lifestyle southwest florida is known for.
Winding Cypress, 7564 Winding Cypress Dr, Naples, Florida 34114, image 1
$1,030,000$30K
  • 4 Beds
  • 2 Baths
  • 2,230 SqFt
  • $462/SqFt
Premium
House for sale in Winding Cypress
7564 Winding Cypress Dr, Naples, FL 34114
Most lake lots give you water. This one gives you the sunset. The western exposure at 7564 winding cypress drive turns the back of the house into the best seat in the community every evening, and the extended lanai is built with no-see-um mesh in picture-window construction, so the horizon comes through without a frame across it. Behind that view is a one-owner 2018 divosta summerwood, offered for the first time since it was built and expanded well past the standard plan: 2, 230 square feet, four bedrooms, ten-foot ceilings, eight-foot doors, and an extended great room under a coffered ceiling with crown molding carried through every room. Arched openings, plantation shutters on every window, and porcelain plank floors give the interior a finished, architectural quality that reads as both coastal and modern. The kitchen was renovated after purchase and it shows: white shaker cabinetry, salt-and-pepper granite, a counter-to-ceiling white subway backsplash, an externally vented stainless chimney hood over a natural gas range, under-cabinet lighting, a wine fridge, a walk-in pantry, and an extended island with seating under glass pendants. The dining area sits beneath its own cluster chandelier, and the great room holds a full sectional, a game table, and a bar cabinet with room to spare. Outside, the lanai is a true second living room. A resort-style saltwater pool with an in-water sundeck, a spa placed on the sight line so the water reads as one composition from inside the house, a silver river travertine deck, and a covered section deep enough for an outdoor sectional and a six-seat dining table. Natural gas outdoor is included as well. Foxtail and christmas palms frame the lake beyond. New pool motor in 2024. Then the part that separates a florida house from a florida headache. Impact windows, custom window treatments and impact doors are installed throughout. Stormsmart electric screens on the lanai and front vestibule. A whole-house and pool generac generator. A flat concrete tile roof, tankless water heater, and centrally wired alarm. Close the house in may, fly north, and stop watching the tropics. The extended garage has its own split-system a/c; the attic has pull-down stairs and added insulation. The owner's suite carries a california closets build-out, and every closet in the house has extra shelving. Dimmer switches throughout. The designer furnishings shown, indoors and out, are available under separate negotiation. Bring a suitcase if you like. Winding cypress is a gated, natural-gas community of 766 homes set inside 800 acres of protected preserve and 80 acres of lakes. Residents have an on-site restaurant and bar, resort and lap pools with a spa and fire pit, an oversized fitness center, tennis, pickleball, bocce, two dog parks, a full activities calendar, and miles of boardwalk and preserve trail. Lawn care is included in the dues. Marco island's beaches are ten minutes out; fifth avenue south is about fifteen.
Winding Cypress, 7230 Live Oak Dr, Naples, Florida 34114, image 1
$1,195,000
  • 3 Beds
  • 3 Baths
  • 2,500 SqFt
  • $478/SqFt
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House for sale in Winding Cypress
7230 Live Oak Dr, Naples, FL 34114
Beautiful home inside and out pinnacle style home in winding cypress. This home features 3 generous size bedrooms, 3 full bath , 2 car plus golf cart garage . Custom oversized salt water heated pool with stairs , sunshelf, 3 waterfall features and oversized hot tub all surrounded by beautiful landscaping on an oversized lot with plenty of privacy. All impact resistance doors and windows, zero corner slider and a transfer switch with portable generator which handles lights, refrigerator and tv. Located close to the amenity center , dog park etc and all that winding cypress community offers, the shady palm restaurant, resort pool and spa, incredible gym and motion room for active classes, library , event room . Winding cypress can be as active as you wish to be or to chill , either way you will fall in love with this community
Winding Cypress, 7478 Winding Cypress Dr, Naples, Florida 34114, image 1
$1,349,500
  • 3 Beds
  • 3 Baths
  • 2,634 SqFt
  • $512/SqFt
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House for sale in Winding Cypress
7478 Winding Cypress Dr, Naples, FL 34114
Bring offers! Welcome to this highly upgraded infinity model, a rare offering in the prestigious winding cypress community of naples. Built by renowned divosta builders, this residence is one of only three infinity models within a community of more than 750 homes, making it an exceptionally unique opportunity. Featuring an extra-wide three-car garage with a dedicated third bay ideal for a golf cart, hobby vehicle, or additional storage, this home has been significantly enhanced with premium upgrades throughout and offers a level of quality rarely found in today's market. Designed for both luxury and everyday comfort, the expansive open-concept floor plan showcases soaring tray ceilings exceeding 11 feet, custom faux painting, extensive crown molding, and elegant designer finishes throughout. The spacious great room seamlessly connects to the gourmet kitchen, highlighted by a six-burner thermador gas range and cooktop, premium liebherr refrigerator, custom cabinetry, and a massive leather-finished quartzite island perfect for entertaining. The seller's extensive investment in upgrades is evident in every detail. Designer window treatments, custom bed coverlets, built-in features, and custom closets throughout create a refined, move-in-ready environment. The completely remodeled primary bath offers a spa-inspired retreat featuring a curbless walk-in shower, floating vanity, premium fixtures, designer tilework, and stunning 48-inch porcelain tile flooring throughout. Outdoor living is equally impressive. The expansive lanai with desirable western exposure captures spectacular naples sunsets and provides ample space for a custom pool, spa, and additional outdoor living areas. Pool plans and contractor quotes are available, making it easy for the next owner to create their ideal backyard oasis. The fully equipped outdoor kitchen provides the perfect setting for entertaining family and friends while enjoying the privacy and tropical surroundings. Additional upgrades include hurricane-impact windows and doors, a dramatic zero-corner sliding glass door, whole-house generator, tankless water heater, kinetico water filtration system, sonos surround sound system, epoxy-coated garage floors, insulated garage doors, built-in garage storage, and a dedicated air-conditioning system for the garage. As one of naples' premier natural gas communities, winding cypress offers an unmatched lifestyle with a residents-only restaurant, resort-style pool and spa, fitness center, pickleball, tennis and bocce courts, and over 800 acres of protected preserve. Ideally located just 10 minutes from marco island's white sand beaches and approximately 15 minutes from olde naples, this exceptional residence combines rarity, luxury, and location in one extraordinary offering. This is more than a home—it's a statement of quality, craftsmanship, and lifestyle. One or more photos have been virtually staged, ai-generated, or rendered.
Winding Cypress, 6907 Cocoplum St, Naples, Florida 34114, image 1
$1,295,000
  • 3 Beds
  • 3 Baths
  • 2,515 SqFt
  • $515/SqFt
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House for sale in Winding Cypress
6907 Cocoplum St, Naples, FL 34114
Priced to sell! Discover exceptional value in one of naples’ most desirable lifestyle communities, winding cypress. Ideally situated on an oversized preserve lot with peaceful pond views, this beautifully maintained pinnacle floor plan offers over 2, 500 square feet of living space with 3 spacious bedrooms, 3 full bathrooms, and a versatile den. Built in 2020, this move-in-ready residence combines elegant finishes, thoughtful upgrades, and outstanding indoor-outdoor living. The expansive outdoor area features a large picture-window screened lanai, gas-heated saltwater pool and spa, custom outdoor kitchen, and generous brick-paver lanai with a covered entertaining area—perfect for enjoying the naples lifestyle year-round. A newly installed electric hurricane screen provides additional protection and convenience. The home is equipped with whole-house hurricane shutters, a whole-house generator capable of supporting the pool and spa, and an oversized 3-car garage with epoxy flooring and hurricane-rated, insulated garage doors. Additional attic insulation and a separate garage a/c system provide the option for climate-controlled storage or workspace. The beautifully appointed kitchen features white quartz countertops, premium stainless steel appliances, a gas cooktop, and a beverage refrigerator. The spacious primary suite offers exceptional organization with a custom california closets design, while the custom pantry provides additional storage and functionality. Beyond the residence, winding cypress offers an exceptional resort-style lifestyle. The impressive clubhouse features a heated resort pool and spa, poolside dining at the shady palm, state-of-the-art fitness center, library, and elegant gathering rooms. Residents also enjoy tennis and pickleball courts, bocce, dog parks, a community garden, and scenic walking and nature trails. Beautifully maintained grounds and a welcoming atmosphere create a true sense of community, all while being conveniently located near the best of naples. Located in an x flood zone, with no flood insurance required, this exceptional home offers the perfect combination of luxury, privacy, recreation, and peace of mind. Priced to sell and offering tremendous value, this is an opportunity to own a beautifully upgraded home in one of naples’ premier communities.

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

$0.24 / Sq.Ft.

Monthly ownership cost
↑41%above peers
↓17%below city avg
This Community
$0.24
Comparable Mid-Tier Avg
$0.17
Naples, FL Avg
$0.29
$0.00
$0.18
$0.35
Higher than peers, lower than the city average
Peer Set · 52 comparable communities
See Cost Context

Frequently Asked Questions

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Matched by price tier, HOA, and lifestyle
Results 3 of 26
Azure At Hacienda Lakes, 9209 N Cayman Dr, Naples, Florida 34114, image 1
$565,000$34K
Villa for sale in Azure At Hacienda Lakes
9209 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 Lakes
9225 Cayman Dr, Naples, FL 34114
Valencia Trails, 12445 Dahlia Ct, Naples, Florida 34120, image 1
$709,000
House for sale in Valencia Trails
12445 Dahlia Ct, Naples, FL 34120
1 - 3 of 26 Results

Preconstruction in Naples

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3300 Gulf Shore Naples
3300 Gulf Shore Naples
3300 Gulf Shore Naples
Condos
  • 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
  • Starts at
    $3.6M
  • Units
    15
  • Stories
    3
Details
Epique At Pelican Bay
Epique At Pelican Bay
Epique At Pelican Bay
Condos
  • 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
Olana Naples Residences
Olana Naples Residences
Condos
  • 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
Palazzo At Bayfront
Palazzo At Bayfront
Condos
  • 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.

Details
Park Place On Gulf Shore
Park Place On Gulf Shore
Park Place On Gulf Shore
Condos
  • 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.

Details
Rosewood Residences Naples
Rosewood Residences Naples
Rosewood Residences Naples
Condos
  • 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 Halcyon Residences & Marina
The Halcyon Residences & Marina
The Halcyon Residences & Marina
Condos
  • Starts at
    $3M
  • Units
    66
  • Stories
    6

Welcome to The Halcyon

The Halcyon Residences and Marina presents a rare collection of just 66 estate-scale homes, set on over eight acres of prime waterfront along the Gordon River in Naples, Florida.

This is a coastal enclave shaped by marina life, wellness, and exceptional living. Every detail is intentional and designed to support idyllic days with understated luxury.

Moments from Old Naples, yet removed from its pace, The Halcyon offers an exceptional balance: seamless access to the city’s dining, culture, and coastline, paired with the rarity of a true waterfront retreat.

Terraces open to the marina, amenity spaces flow naturally from pool to courts to gardens, and the Captain’s Club becomes a daily point of connection.

The Halcyon is for anyone who seeks the ease of condominium living, yet expects the proportions, comfort, and character of a true family home.

The Residences

With homes between 2,190 and 3,375 square feet offering two to four bedroom floor plans, The Halcyon offers a new standard of luxury lifestyle, all within walking distance of 5th Avenue South and Old Naples.

Each residence is accessed via a private elevator arrival, establishing a sense of privacy and ownership from the moment you enter. Ceiling heights approaching 11’ in principal rooms, with floor-to-ceiling glazing that fills each home with abundant natural light. Every residence benefits from multiple private terraces of up to 50’ long, all with gas outdoor kitchen grills ensuring each home enjoys open views across the marina, waterway, amenity, or sky decks, leading to a seamless connection between indoor and outdoor living. The terrace homes benefit additionally from extensive outdoor living spaces up to 30’ deep, creating their own private outdoor sanctuary.

Living and dining areas are beautifully proportioned to accommodate full-scale gatherings, generous seating arrangements, and unobstructed circulation. The primary kitchen is supported by a butler’s kitchen both of which benefit from extensive Wolf and Sub Zero premium appliances.

Double doors lead to the principal bedrooms, with dual walk-in closets and spa-like primary e n-suite bathrooms. Each and every space reflecting discrete, intelligent design.

Barefoot Luxury

There’s a reason people who know Florida, often choose the West Coast. Life here follows a different rhythm, less hurried, more grounded, and closely connected to the water and the outdoors.

At The Halcyon, luxury is defined by time and intention. It’s about choosing what to do with your time and spending it with the people who bring you joy.

It lives in the connections and the friendships, in conversations that stretch late under the stars. In an energizing smoothie after a morning stretch on the club terrace. In the thrill of a pickleball or padel match, or simply watching the game from the quiet comfort of your den.

It’s your time to live off the clock. This is barefoot luxury that feels confident, natural and entirely your own.

The Halcyon Club

With over 55,000 square feet of private amenity space, The Halcyon offers one of the most complete and thoughtfully curated lifestyle experiences in Naples.

Rather than concentrating activity into a single clubhouse, amenities are layered across the waterfront setting, designed to support energy, wellness, productivity, and enjoyment in equal measure, all accessible and managed via the exclusive residents app.

At the heart of the community sits the 120 slip private marina, seamlessly integrated into daily life and supported by concierge services for stress-free ownership.

Details
The Ritz-Carlton Residences Naples
The Ritz-Carlton Residences Naples
The Ritz-Carlton Residences Naples
Condos
  • 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.

Details

Comparable & Nearby Subdivisions

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Premium
Naples, FL 34114
For Sale (2)
$1.2M - $1.3M
For Rent (4)
$7K - $13K
Premium
Naples, FL 34114
For Sale (2)
$849K - $899K
For Rent (5)
$5K - $13K
Mid-Tier
Naples, FL 34120
For Sale (23)
$709K - $1.9M
For Rent (2)
$7K - $9K
Premium
Naples, FL 34114
For Sale (3)
$649K - $900K
For Rent (3)
$7K - $7K
Premium
Naples, FL 34112
For Sale (1)
$850K - $850K
For Rent (3)
$8K - $9K

Schools

Scores

Walk Score®
Car-Dependent. Almost all errands require a car
0

100
Bike Score®
Somewhat Bikeable. Minimal bike infrastructure
29

100
Sound Score®
Bearable noise
82

100
Airport Score
Close to airports. Noticeable airport activity
0

100
Traffic Score
Congested area. Frequent traffic delays
22

100
Local Score
Limited local amenities nearby
0

100

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