Winding Cypress Homes

/50
Est $922,747 Not Listed For Sale
- 2 Beds
- 2.5 Baths
- 2,105 Sq Ft
6830 Greenbriar Ct, Naples, FL 34114

6830 Greenbriar Ct, Naples, FL 34114

/27
$539,000
- 2 Beds
- 2 Baths
- 1,574 Sq Ft
7666 Jacaranda Ln, Naples, FL 34114

The finest in resort style living! You do not want to miss this opportunity to own a find like this in the community of Winding Cypress. This beautifully updated 2+den/2 bath jem has 9'4" ceilings with a two car garage is move-in ready and it has everything you need to call the sought after Villa your home. Newer refrigerator + hot water tank, pavers, plantation shutters and much more. Almost 2/3

Angela Plante RE Florida Homes

7666 Jacaranda Ln, Naples, FL 34114
/50
$1,255,000 Sold Jul 24, 2025
- 2,496 Sq Ft
- $503/SF
- 161 Days On Market
- 3 Beds
- 3 Baths
- Built 2020
7675 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

Taylor Smith Premier Sotheby's Int'l Realty

7675 Winding Cypress Dr, Naples, FL 34114

/48
Est $916,767 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,107 Sq Ft
6846 Greenbriar Ct, Naples, FL 34114

6846 Greenbriar Ct, Naples, FL 34114

/37
$1,188,000 Open Sun 1PM - 4PM
- 3 Beds
- 2 Baths
- 2,166 Sq Ft
7457 Winding Cypress Dr, Naples, FL 34114

The Martin Ray Floor Plan is PRIVACY-PRIVACY-PRIVACY.An exceptional model styled home on a premium lot withrare, unobstructed views of the lake and the Preserve. This residence offers unmatched privacy and outdoor living, with twostandout features: an expansive screened lanai with custom accent lighting, saltwater, heatedpool, plus an outdoor dry bar with refrigerator and

Beth M Abraham Gulf Coast International Prop

7457 Winding Cypress Dr, Naples, FL 34114
/11
$510,000 Sold Jul 16, 2025
- 1,579 Sq Ft
- $323/SF
- 61 Days On Market
- 2 Beds
- 2 Baths
- Built 2018
7650 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

Theresa Bocka William Raveis Real Estate

7650 Jacaranda Ln, Naples, FL 34114

/34
Est $903,920 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,094 Sq Ft
6723 Pennyroyal Dr, Naples, FL 34114

6723 Pennyroyal Dr, Naples, FL 34114

/45
$649,900
- 2 Beds
- 2 Baths
- 1,685 Sq Ft
7248 Live Oak Dr, Naples, FL 34114

Ready for New Owners to Enjoy -Welcome home to this charming Abbeyville model featuring its inviting open-floor concept where natural light streams through the windows. The kitchen boasts granite counters, stainless appliances and a center island with pendant lights and extra storage for everyday use and easy entertaining. The pantry closet has plenty of space for all of your staple goods. Low

Theresa Bocka William Raveis Real Estate

7248 Live Oak Dr, Naples, FL 34114
/42
$855,000 Sold Jul 11, 2025
- 2,124 Sq Ft
- $403/SF
- 103 Days On Market
- 3 Beds
- 3 Baths
- Built 2022
6906 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

Terry Trombetti Berkshire Hathaway FL Realty

6906 Winding Cypress Dr, Naples, FL 34114

/29
Est $1,389,114 Not Listed For Sale
- 3 Beds
- 3.5 Baths
- 2,952 Sq Ft
6962 Winding Cypress Dr, Naples, FL 34114

6962 Winding Cypress Dr, Naples, FL 34114

/37
$1,695,000
- 4 Beds
- 4 Baths
- 3,656 Sq Ft
7412 Winding Cypress Dr, Naples, FL 34114

Luxurious Lakeside Living in Winding Cypress – Rare One Owner Pinnacle Model! Welcome to this stunning lake view home offering 3,656 sq. ft. of modern elegance in the prestigious, amenity-rich community of Winding Cypress. With 4 bedrooms, 4 bathrooms, a den, bonus room, and 2,5-car garage, this home is thoughtfully designed for both everyday living and entertaining on a grand

Manuela Schinagl Manuela Realty

7412 Winding Cypress Dr, Naples, FL 34114
/17
$975,000 Sold Jun 20, 2025
- 2,496 Sq Ft
- $391/SF
- 41 Days On Market
- 3 Beds
- 3 Baths
- Built 2018
7530 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

Theresa Bocka William Raveis Real Estate

7530 Geranium Way, Naples, FL 34114

/50
Est $1,445,630 Not Listed For Sale
- 4 Beds
- 4 Baths
- 3,656 Sq Ft
6903 Cocoplum St, Naples, FL 34114

6903 Cocoplum St, Naples, FL 34114

/45
$599,900
- 2 Beds
- 2 Baths
- 1,544 Sq Ft
7659 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

Stanley Whitcomb III Premiere Plus Realty Company

7659 Jacaranda Ln, Naples, FL 34114
/46
$453,000 Sold Jun 20, 2025
- 1,574 Sq Ft
- $288/SF
- 100 Days On Market
- 2 Beds
- 2 Baths
- Built 2018
7686 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

Kendra Hoefs Realty One Group MVP

7686 Jacaranda Ln, Naples, FL 34114

/43
Est $930,322 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,884 Sq Ft
6762 Pennyroyal Dr, Naples, FL 34114

6762 Pennyroyal Dr, Naples, FL 34114

/41
$749,900
- 3 Beds
- 2 Baths
- 1,594 Sq Ft
7670 Jacaranda Ln, Naples, FL 34114

Discover refined living with this beautifully appointed villa in Winding Cypress, where luxury and comfort meet in perfect balance. Designed for those who appreciate both elegance and ease, this home offers an unparalleled lifestyle inside and out.Arriving fully furnished and enhanced by the sellers’ two-seater Club Car golf cart, this property delivers a true move-in ready experience. Every

Sean Smuk Coldwell Banker Realty

7670 Jacaranda Ln, Naples, FL 34114
/27
$530,000 Sold Jun 20, 2025
- 1,554 Sq Ft
- $341/SF
- 271 Days On Market
- 2 Beds
- 2 Baths
- Built 2019
7702 Jacaranda Ln, Naples, FL 34114

Absolutely the best deal on a 2 bedroom plus den with French doors, 2 baths, 2 car garage attached villa with your own POOL in Winding Cypress. You better Hurry. Furniture negotiable too, move right in for season, nicely furnished.What's Special: *Open floor plan *Epoxy garage floor *Granite countertops*3 ft. bathroom countertops *Remote controlled garage screen*Remote controlled

Mike Miller Berkshire Hathaway FL Realty

7702 Jacaranda Ln, Naples, FL 34114

/47
Est $930,863 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,673 Sq Ft
7454 Winding Cypress Dr, Naples, FL 34114

7454 Winding Cypress Dr, Naples, FL 34114

/44
$639,000
- 2 Beds
- 2 Baths
- 1,554 Sq Ft
7690 Jacaranda Ln, Naples, FL 34114

Set against private garden views with tranquil eastern exposure, this beautifully appointed villa in Winding Cypress offers a peaceful retreat and effortless indoor-outdoor living. Featuring two bedrooms plus a den, two baths, and a two-car garage, this thoughtfully designed residence combines quiet luxury with meticulous updates in one of Naples' most dynamic lifestyle communities. The screened

Michelle Thomas Premier Sotheby's International Realty

7690 Jacaranda Ln, Naples, FL 34114
/27
$675,000 Sold May 30, 2025
- 1,554 Sq Ft
- $434/SF
- 47 Days On Market
- 2 Beds
- 2 Baths
- Built 2019
7742 Jacaranda Ln, Naples, FL 34114

This move in ready furnished Winding Cypress Serenity 2 bedroom plus den Attached Villa with POOL & SPA is a unique quality find. This Serenity floor plan with the kitchen conveniently tucked away behind peninsula island allows for optimal entertaining space. Kitchen features Quartz countertops, natural gas range & SS appliances. Other high quality highlights include, plantation shutters, crown

Bob Bailey R L Bailey Realty Inc.

7742 Jacaranda Ln, Naples, FL 34114

/38
Est $1,410,045 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,852 Sq Ft
6871 Cocoplum St, Naples, FL 34114

6871 Cocoplum St, Naples, FL 34114

/16
$539,000
- 2 Beds
- 2 Baths
- 1,554 Sq Ft
7602 Jacaranda Ln, Naples, FL 34114

Now being offered FURNISHED! Welcome to this meticulous light and bright two bedroom plus den, two bathroom property located in the preserve style, amenity rich community of Winding Cypress. Featuring stainless steel appliances, roomy kitchen, in residence laundry room with newer washer and dryer, screened in lanai, and open floor plan this home has multiple indoor and outdoor spaces for

Taylor Miller Coldwell Banker Realty

7602 Jacaranda Ln, Naples, FL 34114
/17
$925,000 Sold May 14, 2025
- 2,118 Sq Ft
- $437/SF
- 8 Days On Market
- 3 Beds
- 2 Baths
- Built 2020
6854 Greenbriar Ct, Naples, FL 34114

A MOST INCREDIBLE OFFERING MARTIN RAY. THIS HOME HAS IT ALL.HURRICANE IMPACT WINDOWS & SLIDING GLASS DOOR, HURRICANE IMPACT MAIN ENTRANCE DOOR WITH LEADED GLASS, CEILINGS WITH TRAYS, COFFERS, & WIDE MOLDINGS, EXTERIOR LIGHTING PACKAGE, KITCHEN CABINET PACKAGE INCLUDING SOFT CLOSE DOORS, QUARTZ COUNTERTOPS,2 CAR GARAGE WITH UTILITY SINK, EXTENDED DRIVEWAY & MAIN ENTRANCE PAVERS,

Theresa Bocka William Raveis Real Estate

6854 Greenbriar Ct, Naples, FL 34114

/51
Est $1,325,865 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,515 Sq Ft
6907 Cocoplum St, Naples, FL 34114

6907 Cocoplum St, Naples, FL 34114

/33
$579,900
- 3 Beds
- 2 Baths
- 1,554 Sq Ft
7176 Live Oak Dr, Naples, FL 34114

Sophisticated Villa Living in Winding Cypress – Priced to Sell/Fully Furnished. An extraordinary opportunity awaits in the highly sought-after Winding Cypress community—this impeccably upgraded 3-bedroom, 2-bathroom villa is set on the largest homesite in the neighborhood, offering both privacy and an expansive outdoor retreat. Thoughtfully enhanced with luxury upgrades and high-end finishes,

Samantha Kiffney Coldwell Banker Realty

7176 Live Oak Dr, Naples, FL 34114
/47
$760,000 Sold May 08, 2025
- 1,921 Sq Ft
- $396/SF
- 52 Days On Market
- 2 Beds
- 2 Baths
- Built 2021
6758 Pennyroyal Dr, Naples, FL 34114

This beautifully upgraded 2-bedroom plus den, 2-bath Mystique floorplan home in Winding Cypress offers the perfect blend of style, comfort, and functionality. The open-concept design features a zero-corner slider, seamlessly connecting indoor and outdoor spaces, while impact windows and doors provide security and energy efficiency. A whole-home generator ensures uninterrupted comfort and peace of

Kendra Hoefs Realty One Group MVP

6758 Pennyroyal Dr, Naples, FL 34114

/50
Est $931,848 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,152 Sq Ft
6818 Greenbriar Ct, Naples, FL 34114

6818 Greenbriar Ct, Naples, FL 34114

/41
$534,500
- 2 Beds
- 2 Baths
- 1,554 Sq Ft
7658 Jacaranda Ln, Naples, FL 34114

This beautiful Winding Cypress Serenity Villa home offers 1,554 sq. ft. of comfort with 2 bedroom plus den, 2 bathrooms, screened lanai, and a 2-car garage. It features multiple quality upgrades including stainless appliances with both gas and electric connectivity for the stove, 22" porcelain tile on the diagonal throughout, plantation shutters, Quartz countertops in kitchen and bathrooms, den

Bob Lashenka Downing Frye Realty Inc.

7658 Jacaranda Ln, Naples, FL 34114
/13
$860,000 Sold May 02, 2025
- 2,208 Sq Ft
- $389/SF
- 66 Days On Market
- 3 Beds
- 2 Baths
- Built 2020
6763 Pennyroyal Dr, Naples, FL 34114

Don't miss out on this stunning impeccably maintained Summerwood model in the highly coveted Winding Cypress community. This beautifully designed home offers 3 bedrooms, plus a dedicated home office, perfect for today’s lifestyle. The charming front porch, an inviting space to unwind with your morning coffee, and be greeted by a designer glass entry door. Inside, you’ll find a bright and open

Theresa Bocka William Raveis Real Estate

6763 Pennyroyal Dr, Naples, FL 34114

/43
Est $958,116 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,148 Sq Ft
6695 Pennyroyal Dr, Naples, FL 34114

6695 Pennyroyal Dr, Naples, FL 34114

/32
$640,000
- 2 Beds
- 2 Baths
- 1,574 Sq Ft
7815 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

Kati Bepko Coldwell Banker Realty

7815 Jacaranda Ln, Naples, FL 34114
/20
$537,000 Sold May 01, 2025
- 1,554 Sq Ft
- $346/SF
- 26 Days On Market
- 2 Beds
- 2 Baths
- Built 2016
7591 Jacaranda Ln, Naples, FL 34114

Price Negotiable! Seller is highly motivated!! Discover your slice of paradise in this stunning 2-bedroom plus den villa, located in the resort-style community of Winding Cypress. With exquisite builder-installed upgrades, this home features a sleek open floor plan, granite countertops, and elegant porcelain tile throughout. The kitchen is outfitted with stainless appliances and gas stove

william Romano Keller Williams Marco Realty

7591 Jacaranda Ln, Naples, FL 34114

/50
Est $625,875 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,544 Sq Ft
7611 Jacaranda Ln, Naples, FL 34114

7611 Jacaranda Ln, Naples, FL 34114

/28
$665,000
- 2 Beds
- 2 Baths
- 1,805 Sq Ft
7370 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

Joseph Scott Compass Florida LLC

7370 Mockingbird Ct, Naples, FL 34114
/50
$992,500 Sold Apr 17, 2025
- 2,062 Sq Ft
- $481/SF
- 115 Days On Market
- 2 Beds
- 2 Baths
- Built 2016
7404 Winding Cypress Dr, Naples, FL 34114

The most private homesite in Winding Cypress Resort community, this exceptional home offers views abundant with trees and lake, bordered by a lush preserve and expansive buffer zones. Breathtaking southwestern water views provide the ideal backdrop, rivaling the most stunning beach sunsets. Step outside to the largest covered lanai in the community, complete with a sparkling pool and spa,

Taylor Smith Premier Sotheby's Int'l Realty

7404 Winding Cypress Dr, Naples, FL 34114

/35
Est $875,144 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,080 Sq Ft
6742 Pennyroyal Dr, Naples, FL 34114

6742 Pennyroyal Dr, Naples, FL 34114

/10
$720,000 Pending
- 2 Beds
- 2 Baths
- 1,654 Sq Ft
6787 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

Theresa Bocka William Raveis Real Estate

6787 Winding Cypress Dr, Naples, FL 34114
/50
$635,000 Sold Apr 08, 2025
- 1,554 Sq Ft
- $409/SF
- 40 Days On Market
- 2 Beds
- 2 Baths
- Built 2015
7199 Live Oak Dr, Naples, FL 34114

Rare villa opportunity in Winding Cypress! For the first time in over a year, a villa with a private pool and spa on an extra-large lot is available. Enjoy unmatched privacy with huge space between neighbors and serene ultra-private preserve views. This turnkey, fully furnished home features impact windows, 8-foot doors, new bedroom flooring, fresh landscaping and more. This natural gas community

Taylor Smith Premier Sotheby's Int'l Realty

7199 Live Oak Dr, Naples, FL 34114

/38
Est $893,649 Not Listed For Sale
- 2 Beds
- 2.5 Baths
- 2,117 Sq Ft
6898 Winding Cypress Dr, Naples, FL 34114

6898 Winding Cypress Dr, Naples, FL 34114

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