Winding Cypress Homes

/50
$943,000 Open Sun 1PM - 4PM
- 3 Beds
- 3 Baths
- 2,150 Sq Ft
6698 Pennyroyal Dr, Naples, FL 34114

Discover resort-style living in this rare three-bedroom plus den, three-bath natural gas home in the highly sought-after community of Winding Cypress. Designed for privacy and effortless indoor–outdoor living, it features an oversized fully custom pool with integrated seamless spa and a panoramic barless screen lanai, integrated home theater sound, all overlooking lush, tranquil landscaping. The

Taylor Smith Premier Sotheby's Int'l Realty

6698 Pennyroyal Dr, Naples, FL 34114
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/50
$858,000 Sold Jan 16, 2026

6856 Winding Cypress Dr, Naples, FL 34114
- 3 Beds
- 2 Baths
- 2,076 Sq Ft
- Built 2021
Last Sold Summary
- 5% Below List Price
- $413/SF
- 81 Days On Market
Last Listing Agent Brian Stolliker BERKSHIRE HATHAWAY HOMESERVICES FLORIDA REALTY

6856 Winding Cypress Dr, Naples, FL 34114

/41
Est $1,354,680 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,515 Sq Ft
6880 Cocoplum St, Naples, FL 34114

6880 Cocoplum St, Naples, FL 34114

/48
$600,000
- 3 Beds
- 2 Baths
- 1,554 Sq Ft
7167 Live Oak Dr, Naples, FL 34114

Rare villa opportunity in Winding Cypress! This turnkey, fully furnished villa sits on an extra-large, ultra-private lot with exceptional spacing between neighbors, creating a peaceful and open feel that is hard to find. The backyard is a retreat, featuring a saltwater private pool framed by mature cypress trees, colorful landscaping and wide natural preserve views. Inside, the home offers

Taylor Smith Premier Sotheby's Int'l Realty

7167 Live Oak Dr, Naples, FL 34114
/48
$860,000 Sold Oct 09, 2025

6870 Winding Cypress Dr, Naples, FL 34114
- 3 Beds
- 2 Baths
- 2,084 Sq Ft
- Built 2021
Last Sold Summary
- 7% Below List Price
- $413/SF
- 75 Days On Market
Current Estimated Value $858,714

Last Listing Agent Kendra Hoefs Realty One Group MVP

6870 Winding Cypress Dr, Naples, FL 34114

/22
Est $907,281 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,152 Sq Ft
6801 Greenbriar Ct, Naples, FL 34114

6801 Greenbriar Ct, Naples, FL 34114

/36
$925,000
- 3 Beds
- 2 Baths
- 2,084 Sq Ft
6902 Winding Cypress Dr, Naples, FL 34114

Stunning 3-Bedroom + Den Home in Sought-After Winding Cypress – Welcome to your dream home in the prestigious, resort-style community of Winding Cypress in Naples, FL. Built in 2022, this impeccably maintained 3-bedroom + den, 2-bathroom residence blends modern design with everyday comfort. Step inside to find an open-concept floor plan featuring, abundant natural light, and contemporary finishes

Elliot Barton Waterfront Realty Group Inc

6902 Winding Cypress Dr, Naples, FL 34114
/33
$750,000 Sold Sep 10, 2025

7128 Lily Way, Naples, FL 34114
- 2 Beds
- 2 Baths
- 1,685 Sq Ft
- Built 2015
Last Sold Summary
- 17% Below List Price
- $445/SF
- 143 Days On Market
Current Estimated Value $731,793

Last Listing Agent Kate Pentelow Premiere Plus Realty Company

7128 Lily Way, Naples, FL 34114

/50
Est $937,014 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

/39
$550,000
- 3 Beds
- 2 Baths
- 1,554 Sq Ft
7176 Live Oak Dr, Naples, FL 34114

Welcome to effortless, refined living in the highly desirable Winding Cypress community. Set on the largest homesite in the neighborhood, this impeccably upgraded 3-bedroom, 2-bath villa offers exceptional privacy, expansive outdoor space, and a true lock-and-leave lifestyle. Furnishings are negotiable, making this a flexible opportunity for both full-time and seasonal residents. Designed for

David Burke John R Wood Properties

7176 Live Oak Dr, Naples, FL 34114
/42
$455,000 Sold Nov 17, 2025

7642 Jacaranda Ln, Naples, FL 34114
- 2 Beds
- 2 Baths
- 1,554 Sq Ft
- Built 2017
Last Sold Summary
- 15% Below List Price
- $293/SF
- 172 Days On Market
Last Listing Agent Scott Bertha Downing Frye Realty Inc.

7642 Jacaranda Ln, Naples, FL 34114

/48
Est $949,148 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,107 Sq Ft
6846 Greenbriar Ct, Naples, FL 34114

6846 Greenbriar Ct, Naples, FL 34114

/48
$1,160,000 Open Sun 1PM - 4PM
- 3 Beds
- 3 Baths
- 2,496 Sq Ft
7520 Blackberry Dr, Naples, FL 34114

Introducing a luxury estate with landscaped privacy corner lot home in Winding Cypress with pool and spa. Step into elegance with this stunning Pinnacle model estate home, set in the prestigious, gated community of Winding Cypress. This home stands out with its soaring raised tray ceilings, rare privacy and spacious yard, impact glass for peace of mind, and an expansive open layout filled with

Taylor Smith Premier Sotheby's Int'l Realty

7520 Blackberry Dr, Naples, FL 34114
/50
$635,000 Sold Apr 08, 2025

7199 Live Oak Dr, Naples, FL 34114
- 2 Beds
- 2 Baths
- 1,554 Sq Ft
- Built 2015
Last Sold Summary
- 4% Below List Price
- $409/SF
- 40 Days On Market
Current Estimated Value $616,551

Last Listing Agent Taylor Smith Premier Sotheby's Int'l Realty

7199 Live Oak Dr, Naples, FL 34114

/34
Est $930,996 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,094 Sq Ft
6723 Pennyroyal Dr, Naples, FL 34114

6723 Pennyroyal Dr, Naples, FL 34114

/41
$739,900
- 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
/48
$900,000 Sold Aug 07, 2025

6848 Winding Cypress Dr, Naples, FL 34114
- 2 Beds
- 2 Baths
- 1,901 Sq Ft
- Built 2021
Last Sold Summary
- $473/SF
- 23 Days On Market
Current Estimated Value $878,155

Last Listing Agent Kendra Hoefs Realty One Group MVP

6848 Winding Cypress Dr, Naples, FL 34114

/29
Est $1,334,482 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

/50
$925,000 Pending
- 3 Beds
- 2 Baths
- 2,003 Sq Ft
6779 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,

Kendra Hoefs Realty One Group MVP

6779 Winding Cypress Dr, Naples, FL 34114
/27
$530,000 Sold Jun 20, 2025

7702 Jacaranda Ln, Naples, FL 34114
- 2 Beds
- 2 Baths
- 1,554 Sq Ft
- Built 2019
Last Sold Summary
- 24% Below List Price
- $341/SF
- 271 Days On Market
Current Estimated Value $537,833

Last Listing Agent Mike Miller Berkshire Hathaway FL Realty

7702 Jacaranda Ln, Naples, FL 34114

/50
Est $1,481,253 Not Listed For Sale
- 4 Beds
- 4 Baths
- 3,656 Sq Ft
6903 Cocoplum St, Naples, FL 34114

6903 Cocoplum St, Naples, FL 34114

/16
$529,000 Open Sun 1PM - 4PM
- 2 Beds
- 2 Baths
- 1,554 Sq Ft
7602 Jacaranda Ln, Naples, FL 34114

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 entertaining guests and hosting

Taylor Miller Coldwell Banker Realty

7602 Jacaranda Ln, Naples, FL 34114
/3
$710,000 Sold Nov 06, 2025

6787 Winding Cypress Dr, Naples, FL 34114
- 2 Beds
- 2 Baths
- 1,654 Sq Ft
- Built 2021
Last Sold Summary
- 1% Below List Price
- $429/SF
- 108 Days On Market
Last Listing Agent Theresa Bocka William Raveis Real Estate

6787 Winding Cypress Dr, Naples, FL 34114

/43
Est $930,755 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,884 Sq Ft
6762 Pennyroyal Dr, Naples, FL 34114

6762 Pennyroyal Dr, Naples, FL 34114

/35
$1,155,000 Open House 2/08
- 3 Beds
- 2 Baths
- 2,166 Sq Ft
7457 Winding Cypress Dr, Naples, FL 34114

The Martin Ray floor plan is uniquely positioned on the community’s only homesite offering a truly PRIVATE, SERENE VIEW. This exceptional setting provides a rare sense of seclusion and tranquility, creating an authentic Florida paradise lifestyle.This residence offers unmatched privacy and outdoor living, with twostandout features: an expansive screened lanai with custom accent lighting,

Beth M Abraham Gulf Coast International Prop

7457 Winding Cypress Dr, Naples, FL 34114
/17
$975,000 Sold Jun 20, 2025

7530 Geranium Way, Naples, FL 34114
- 3 Beds
- 3 Baths
- 2,496 Sq Ft
- Built 2018
Last Sold Summary
- 17% Below List Price
- $391/SF
- 41 Days On Market
Current Estimated Value $967,545

Last Listing Agent Theresa Bocka William Raveis Real Estate

7530 Geranium Way, Naples, FL 34114

/50
Est $901,317 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,158 Sq Ft
6754 Pennyroyal Dr, Naples, FL 34114

6754 Pennyroyal Dr, Naples, FL 34114

/45
$599,900 Pending
- 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 Premiere Plus Realty Company

7659 Jacaranda Ln, Naples, FL 34114
/47
$935,000 Sold Apr 01, 2025

7683 Winding Cypress Dr, Naples, FL 34114
- 3 Beds
- 2 Baths
- 2,018 Sq Ft
- Built 2018
Last Sold Summary
- 6% Below List Price
- $463/SF
- 146 Days On Market
Current Estimated Value $891,270

Last Listing Agent Kimberly Alvord John R Wood Properties

7683 Winding Cypress Dr, Naples, FL 34114

/47
Est $926,436 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
$610,000 Open Sun 1PM - 3PM
- 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
/46
$453,000 Sold Jun 20, 2025

7686 Jacaranda Ln, Naples, FL 34114
- 2 Beds
- 2 Baths
- 1,574 Sq Ft
- Built 2018
Last Sold Summary
- 21% Below List Price
- $288/SF
- 100 Days On Market
Current Estimated Value $479,307

Last Listing Agent Kendra Hoefs Realty One Group MVP

7686 Jacaranda Ln, Naples, FL 34114

/38
Est $1,377,373 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,852 Sq Ft
6871 Cocoplum St, Naples, FL 34114

6871 Cocoplum St, Naples, FL 34114

/37
$825,000
- 3 Beds
- 3 Baths
- 2,128 Sq Ft
6770 Pennyroyal Dr, Naples, FL 34114

Discover your dream home in the prestigious Winding Cypress community! This newly constructed, pet-friendly residence boasts 3 spacious bedrooms plus a versatile den, perfect for guests or a home office. Designed for seamless entertaining, the open-concept floor plan flows effortlessly, with zero-corner sliders merging the indoor living area with a stylish outdoor kitchen and bar—ideal for

Ryan Buchalter William Raveis Real Estate

6770 Pennyroyal Dr, Naples, FL 34114
/50
$850,000 Sold Feb 27, 2025

7073 Live Oak Dr, Naples, FL 34114
- 3 Beds
- 3 Baths
- 2,867 Sq Ft
- Built 2016
Last Sold Summary
- 8% Below List Price
- $296/SF
- 23 Days On Market
Current Estimated Value $815,933

Last Listing Agent Taylor Smith Premier Sotheby's Int'l Realty

7073 Live Oak Dr, Naples, FL 34114

/51
Est $1,341,630 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,515 Sq Ft
6907 Cocoplum St, Naples, FL 34114

6907 Cocoplum St, Naples, FL 34114

/11
$719,900 Open Sun 1PM - 3PM
- 2 Beds
- 2 Baths
- 1,659 Sq Ft
7255 Live Oak Dr, Naples, FL 34114

This home has just been freshly painted inside and out. professionally painted kitchen and bath cabinets, nice private south west waterview , screened lanai able to enlarge or even add a pool. Previous owner had a great workshop in garage with 8 overhead lights, charging station for a Tesla , framed peg boards for hanging tools , custom storage cabinets and a pull down staircase for added

Linda Covino Royal Shell Real Estate, Inc.

7255 Live Oak Dr, Naples, FL 34114
/50
$1,255,000 Sold Jul 24, 2025

7675 Winding Cypress Dr, Naples, FL 34114
- 3 Beds
- 3 Baths
- 2,496 Sq Ft
- Built 2020
Last Sold Summary
- 16% Below List Price
- $503/SF
- 161 Days On Market
Current Estimated Value $1,232,091

Last Listing Agent Taylor Smith Premier Sotheby's Int'l Realty

7675 Winding Cypress Dr, Naples, FL 34114

/50
Est $978,601 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,152 Sq Ft
6818 Greenbriar Ct, Naples, FL 34114

6818 Greenbriar Ct, Naples, FL 34114

/32
$693,000 Pending
- 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

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