Winding Cypress Homes

/50
$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
/47
$935,000 Sold Apr 01, 2025
- 2,018 Sq Ft
- $463/SF
- 146 Days On Market
- 3 Beds
- 2 Baths
- Built 2018
7683 Winding Cypress Dr, Naples, FL 34114

Live the Vacation Lifestyle Every Day in Winding CypressWelcome to a home that feels like a never-ending vacation. This stunning Summerwood residence, nestled in the resort-style community of Winding Cypress, is more than a home—it’s a lifestyle.From the moment you step through the dramatic entry hall, you’re greeted by breathtaking lake views that set the tone for tranquility and

Kimberly Alvord John R Wood Properties

7683 Winding Cypress Dr, Naples, FL 34114

/38
Est $1,565,107 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
$544,000 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
/43
$890,000 Sold Mar 28, 2025
- 2,107 Sq Ft
- $422/SF
- 3 Days On Market
- 3 Beds
- 2 Baths
- Built 2018
7556 Winding Cypress Dr, Naples, FL 34114

Discover luxury living in this modern and bright single-family Martin Ray home, located in the resort-style community of Winding Cypress. With 2,107 square feet of living space, this open concept 3-bedroom plus den, 2-bathroom home offers a harmonious blend of elegance and functionality. Natural light and coffered ceiling details create a bright and airy atmosphere while modern design and neutral

Kimberly Springer Orchid Realty International

7556 Winding Cypress Dr, Naples, FL 34114

/51
Est $1,439,287 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,515 Sq Ft
6907 Cocoplum St, Naples, FL 34114

6907 Cocoplum St, Naples, FL 34114

/48
$900,000
- 2 Beds
- 2 Baths
- 1,901 Sq Ft
6848 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

Kendra Hoefs Realty One Group MVP

6848 Winding Cypress Dr, Naples, FL 34114
/47
$615,000 Sold Mar 24, 2025
- 1,554 Sq Ft
- $396/SF
- 330 Days On Market
- 2 Beds
- 2 Baths
- Built 2016
7113 Live Oak Dr, Naples, FL 34114

BIG PRICE REDUCTION! THIS IS ONE OF THE LOWEST PRICED VILLA POOL HOME! Discover this stunning 3-bedroom, 2-bathroom villa with a 2-car garage and a luxurious gas heated pool that is ideally situated on a premium pie-shaped lot adjacent to nature preserve and near to the vibrant Winding Cypress Amenity Center is the perfect place to make your own paradise. The flex room offers endless

James Trzyna Realty One Group MVP

7113 Live Oak Dr, Naples, FL 34114

/50
Est $1,074,801 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,152 Sq Ft
6818 Greenbriar Ct, Naples, FL 34114

6818 Greenbriar Ct, Naples, FL 34114

/43
$925,000
- 3 Beds
- 2 Baths
- 2,230 Sq Ft
7211 Live Oak Dr, Naples, FL 34114

Welcome to your personal retreat in Winding Cypress, where resort-style living meets sophisticated comfort! This magnificent Summerville Extended model by Pulte is move-in ready and offers an unparalleled blend of privacy, elegance, and stunning lake views. Perfectly positioned on an oversized, pie-shaped lot with no homes behind, you’ll enjoy serene tranquility and an open vista.Entertain with

Felicia Saraceno eXp Realty LLC

7211 Live Oak Dr, Naples, FL 34114
/49
$775,000 Sold Mar 11, 2025
- 1,804 Sq Ft
- $430/SF
- 117 Days On Market
- 2 Beds
- 2 Baths
- Built 2021
6852 Winding Cypress Dr, Naples, FL 34114

This pristine Abbeyville home in Winding Cypress has it all and is not to be missed! Built in 2021, this property has a fresh neutral palate and features a spacious open split bedroom floor plan with 2 bedrooms + den + sunroom and 2 full bathrooms. The 2-car garage has upgraded features including AC, an insulated garage door, a 4' extension, and extra lighting. 10' ceilings add to the

Ashley Prescott DomainRealty.com LLC

6852 Winding Cypress Dr, Naples, FL 34114

/43
Est $1,102,093 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,148 Sq Ft
6695 Pennyroyal Dr, Naples, FL 34114

6695 Pennyroyal Dr, Naples, FL 34114

/81
$895,000
- 3 Beds
- 2 Baths
- 2,107 Sq Ft
6763 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, this stunning home comes with a TRANSFERRABLE FLOOD POLICY. The heart of the home is a

Ryan Finnegan COLDWELL BANKER SUNSTAR REALTY

6763 Winding Cypress Dr, Naples, FL 34114
/50
$850,000 Sold Feb 27, 2025
- 2,867 Sq Ft
- $296/SF
- 23 Days On Market
- 3 Beds
- 3 Baths
- Built 2016
7073 Live Oak Dr, Naples, FL 34114

Welcome to the award-winning Martin Ray home in the prestigious and centrally located Winding Cypress resort community in Naples. This exceptional home features an expansive lanai set on a protected and private preserve, with room for a pool, providing the perfect space to enjoy the serene Florida sunshine. Inside, the bright and airy ambiance is enhanced by a newly enlarged center island with

Taylor Smith Premier Sotheby's Int'l Realty

7073 Live Oak Dr, Naples, FL 34114

/50
Est $679,757 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,544 Sq Ft
7611 Jacaranda Ln, Naples, FL 34114

7611 Jacaranda Ln, Naples, FL 34114

/42
$537,000
- 2 Beds
- 2 Baths
- 1,554 Sq Ft
7642 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

Scott Bertha Downing Frye Realty Inc.

7642 Jacaranda Ln, Naples, FL 34114
/37
$720,000 Sold Feb 13, 2025
- 1,910 Sq Ft
- $377/SF
- 265 Days On Market
- 2 Beds
- 2 Baths
- Built 2015
7247 Live Oak Dr, Naples, FL 34114

JUST REDUCED AND PRICED TO SELL! Welcome to one of the most desirable neighborhoods in Naples. Winding Cypress boasts resort style living with pickleball, tennis, bocci, large gym, movement room, library, internet cafe, banquet room with kitchen, restaurant, and resort style pool with waterfall and lap lane. Currently the only Summerwood model for sale with peaceful panoramic water and preserve

Kati Bepko Coldwell Banker Realty

7247 Live Oak Dr, Naples, FL 34114

/35
Est $922,848 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

/33
$825,000
- 2 Beds
- 2 Baths
- 1,685 Sq Ft
7128 Lily Way, Naples, FL 34114

** PRICE REDUCTION ** Stunning Abbeyville home in Winding Cypress is 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 &

Kate Pentelow Premiere Plus Realty Company

7128 Lily Way, Naples, FL 34114
/34
$650,000 Sold Feb 13, 2025
- 2,230 Sq Ft
- $291/SF
- 376 Days On Market
- 3 Beds
- 2 Baths
- Built 2015
7267 Live Oak Dr, Naples, FL 34114

Best-Valued Single-Family Home with Quality Finishes and Resort-Style Amenities in Winding Cypress! This beautifully crafted 3-bedroom, 2-bathroom home, complete with a private office, is the best-valued single-family residence in the desirable Winding Cypress community. Thoughtfully designed with quality finishes, this home features tile flooring throughout, plantation shutters, crown molding,

Heidi Varsames John R Wood Properties

7267 Live Oak Dr, Naples, FL 34114

/38
Est $970,941 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

/33
$585,000
- 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 Krol Marzucco Real Estate

7176 Live Oak Dr, Naples, FL 34114
/40
$710,000 Sold Jan 21, 2025
- 1,685 Sq Ft
- $421/SF
- 11 Days On Market
- 2 Beds
- 2 Baths
- Built 2016
7263 Live Oak Dr, Naples, FL 34114

WOW! HERE IS A GORGEOUS RESIDENCE THAT WAS PROFESSIONALLY DECORATED AND IS IN PRISTINE CONDITION. THE HOME HAS A RESORT STYLE LARGE PAVER DECK SALT WATER POOL WITH A PICTURE FRAME SCREENED LANAI. ENJOY AN EXPANSIVE DECK AREA TO RELAX, SOAK UP THE SUN, OR JUST TAKE IN THE STUNNING LAKE VIEW. THE GOURMET KITCHEN HAS STATE OF THE ART APPLIANCES, QUARTZ COUNTERS, TILE BACK SPLASH WITH HAND CRAFTED

Tony Walter Island Realty Marco

7263 Live Oak Dr, Naples, FL 34114

/35
Est $806,458 Not Listed For Sale
- 4 Beds
- 3 Baths
- 1,805 Sq Ft
7103 Lily Way, Naples, FL 34114

7103 Lily Way, Naples, FL 34114

/41
$549,000
- 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

Anne Lashenka Downing Frye Realty Inc.

7658 Jacaranda Ln, Naples, FL 34114
/49
$1,495,000 Sold Jan 21, 2025
- 2,519 Sq Ft
- $593/SF
- 56 Days On Market
- 3 Beds
- 3 Baths
- Built 2021
6883 Cocoplum St, Naples, FL 34114

This popular DiVosta Pinnacle Model is situated in the amenity rich community of Winding Cypress. It is possible to purchase this beauty furnished or turnkey furnished as negotiated and agreed upon. This property is a one owner home that's loaded with builder and owner upgrades to include: custom tile plank flooring throughout, 12'+ coffered/tray ceilings with crown molding and custom detail

Theresa Bocka William Raveis Real Estate

6883 Cocoplum St, Naples, FL 34114

/48
Est $993,041 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,998 Sq Ft
7123 Lily Way, Naples, FL 34114

7123 Lily Way, Naples, FL 34114

/41
$640,000
- 3 Beds
- 2 Baths
- 1,544 Sq Ft
7167 Live Oak Dr, Naples, FL 34114

Don't miss your chance to own a Serenity Turnkey Pool Villa in the highly sought-after Winding Cypress community! This meticulously designed residence boasts 3 bedrooms, 2 bathrooms, and a 2-car garage, offering both comfort and style.Step outside to your private outdoor oasis, complete with a tranquil waterfall feature, electrically heated salt pool, built-in speakers, and serene

Kendra Hoefs Realty One Group MVP

7167 Live Oak Dr, Naples, FL 34114
/50
$785,000 Sold Dec 18, 2024
- 1,774 Sq Ft
- $443/SF
- 67 Days On Market
- 2 Beds
- 2 Baths
- Built 2021
6792 Bromeliad Dr, Naples, FL 34114

Welcome to Winding Cypress, where modern elegance meets comfort in this stunning Abbeyville model, Pulte home built in 2021. A beautiful lake view frames the backyard of this meticulously maintained, well designed residence featuring two spacious bedrooms plus a versatile den, perfect for a home office or additional guest space. Step inside to discover a thoughtfully laid out floor plan,

Nancy Bjork John R Wood Properties

6792 Bromeliad Dr, Naples, FL 34114

/33
Est $726,584 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,685 Sq Ft
7108 Lily Way, Naples, FL 34114

7108 Lily Way, Naples, FL 34114

/32
$675,000 Open Sun 1PM - 4PM
- 2 Beds
- 2 Baths
- 1,574 Sq Ft
7815 Jacaranda Ln, Naples, FL 34114

PRICE DRASTICALLY REDUCED FOR QUICK SALE!! This beautiful villa in highly sought-after Winding Cypress offers two bedrooms, two baths plus a den along with a two-car air-conditioned garage. 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

Kati Bepko Coldwell Banker Realty

7815 Jacaranda Ln, Naples, FL 34114
/29
$995,000 Sold Nov 15, 2024
- 2,496 Sq Ft
- $399/SF
- 77 Days On Market
- 3 Beds
- 3 Baths
- Built 2016
7063 Winding Cypress Dr, Naples, FL 34114

Ready for immediate occupancy! home is now vacant and has a nice clean open slate to custom this home to your liking .Take a look at this Pinnacle style home located in the sought after community of Winding Cypress features 3 bdrms 3 baths, office and 3 car garage , hurricane protection measures include whole house generator , impact doors and windows and hurricane storm screen on lanai.

Linda Covino Royal Shell Real Estate, Inc.

7063 Winding Cypress Dr, Naples, FL 34114

/22
Est $826,635 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,107 Sq Ft
7006 Live Oak Dr, Naples, FL 34114

7006 Live Oak Dr, Naples, FL 34114

/47
$1,497,500
- 3 Beds
- 3 Baths
- 2,619 Sq Ft
7478 Winding Cypress Dr, Naples, FL 34114

Welcome to this exceptional Infinity Model home, a rare find in the prestigious Winding Cypress community of Naples, Florida. Built by the esteemed DiVosta Builders, this home is one of only three Infinity Models in a community of over 750 residences, making it a truly exclusive opportunity. Designed with elegance and comfort in mind, this property blends high-end finishes, thoughtful upgrades,

Austin Kellam Coldwell Banker Realty

7478 Winding Cypress Dr, Naples, FL 34114
/42
$690,000 Sold Nov 08, 2024
- 1,685 Sq Ft
- $409/SF
- 20 Days On Market
- 3 Beds
- 2 Baths
- Built 2015
7256 Live Oak Dr, Naples, FL 34114

Welcome to this stunning 3-bedroom, 2-bathroom oasis, perfectly designed for both relaxation and entertaining. Step inside to find a beautifully appointed open floor plan featuring elegant crown molding, recessed lighting, and gleaming tile laid on the diagonal, creating a seamless flow throughout the home. The heart of the house is the gourmet kitchen, where you'll be inspired to cook and

Gabriele H. Vretta John R Wood Properties

7256 Live Oak Dr, Naples, FL 34114

/32
Est $507,170 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,554 Sq Ft
7191 Live Oak Dr, Naples, FL 34114

7191 Live Oak Dr, Naples, FL 34114

/44
$830,000 Open Sun 1PM - 4PM
- 3 Beds
- 3 Baths
- 2,496 Sq Ft
7045 Live Oak Dr, Naples, FL 34114

Welcome to the best kept secret in Naples, the community of Winding Cypress. Winding Cypress is a DiVosta neighborhood, loaded with resident amenities, and just minutes to Olde Naples and Marco Island. This beauty is the most popular model, The Pinnacle, and it is being offered at an amazing value in equity! An entertainer's dream home boasting an expansive open floorplan joining a huge great

Theresa Bocka William Raveis Real Estate

7045 Live Oak Dr, Naples, FL 34114
/50
$860,000 Sold Nov 01, 2024
- 2,198 Sq Ft
- $391/SF
- 159 Days On Market
- 4 Beds
- 2 Baths
- Built 2017
7420 Winding Cypress Dr, Naples, FL 34114

Winding Cypress is the ultimate Naples resort community, and this home serves as the ultimate poolside retreat. The long southwest water views seamlessly blend waterfront serenity, preserved nature, and privacy. Adorning the oversized covered lanai is a deluxe outdoor kitchen complete with every conceivable feature and top-grade finishes. This award-winning Summerwood floor plan boasts every

Taylor Smith Premier Sotheby's Int'l Realty

7420 Winding Cypress Dr, Naples, FL 34114

/19
Est $649,076 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,554 Sq Ft
7175 Live Oak Dr, Naples, FL 34114

7175 Live Oak Dr, Naples, FL 34114

/27
$695,000
- 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

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