Winding Cypress Homes

• 

  

  

  /49

  $799,000

  • 3 Beds
  • 2 Baths
  • 2,198 Sq Ft

  7445 Winding Cypress Dr, Naples, FL 34114

  Welcome to this beautifully appointed 3-bedroom, 2-bathroom + den home in the vibrant and sought-after community of Winding Cypress in Naples. Perfectly positioned on a prime lakefront lot, this residence offers serene, long water views that extend to the untouched beauty of the preserve beyond. Thoughtfully designed for both comfort and style, this home features tall interior doorways, an

  

  Drayton Herold

  KW Elevate Luxury

  (239) 439-4013

  7445 Winding Cypress Dr, Naples, FL 34114
• 

  

  

  /39

  $6,500 per month

  • 4 Beds
  • 3 Baths
  • 3,077 Sq Ft
  • House for Rent

  7763 Winding Cypress Dr, Naples, FL 34114

  Annual Rental available for immediate occupancy. Turnkey Furnished, and ready for you to enjoy. This 2 story Summerwood model home with Breathtaking Pool and Spa offers a spectacular open floor plan. This home has a very large, beautiful Gourmet kitchen with Dining area, generous Great room with baby Grand Piano, 3 Bedrooms, 3 bathrooms on the main floor, 1 bedroom, 1 bathroom, plus a very large

  

  Melanie Listrom

  REMAX Affinity Mercato

  (239) 323-6669

  7763 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
• 

  

  

  /46

  Est $612,217 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,554 Sq Ft

  7694 Jacaranda Ln, Naples, FL 34114

  7694 Jacaranda Ln, Naples, FL 34114
• 

  

  

  /46

  $1,395,000 Open Sun 1PM - 4PM

  • 3 Beds
  • 3 Baths
  • 2,496 Sq Ft

  7788 Winding Cypress Dr, Naples, FL 34114

  Nestled within an exclusive gated community and surrounded by a serene nature preserve, this elegant 3-bedroom, 3-bathroom home with a spacious den/office is the epitome of refined Florida living. The open, airy floor plan flows seamlessly, with high ceilings and large windows that capture abundant natural light and offer unobstructed views of the lush preserve behind the home. This home has

  Justine Hine Royal Shell Real Estate, Inc.

  7788 Winding Cypress Dr, Naples, FL 34114
• 

  

  /11

  $5,500 per month

  • 3 Beds
  • 2.5 Baths
  • 2,123 Sq Ft
  • House for Rent

  6690 Pennyroyal Dr, Naples, FL 34114

  Stunning and spacious, this 2 car garage, 3-bedroom, 2.5-bathroom home built in 2020 offers luxury living with high-end upgrades throughout and located in the sought after amenity rich community of Winding Cypress. This turnkey property comes beautifully furnished with high-end décor and a fully stocked gourmet kitchen, allowing you to move right in and start enjoying your new home from day one.

  Aimee O'Connor Coldwell Banker Realty

  6690 Pennyroyal Dr, 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 countertops, crown

  Kendra Hoefs Realty One Group MVP

  7686 Jacaranda Ln, Naples, FL 34114
• 

  

  /44

  Est $704,497 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,594 Sq Ft

  7682 Jacaranda Ln, Naples, FL 34114

  7682 Jacaranda Ln, Naples, FL 34114
• 

  

  /34

  $999,000 Open Sun 1PM - 3PM

  • 3 Beds
  • 2 Baths
  • 2,100 Sq Ft

  6787 Pennyroyal Dr, Naples, FL 34114

  Beautiful like new mystique contemporary home. 24x24 gorgeous marble look tile floor, custom wood moldings featuring beams in trey ceiling in gathering room, upgraded kitchen back splash and faucet , custom wood hallway, decorative wood wall design in master bedroom with oversized shower and upgraded shower heads, custom master closet, design. laundry room with plenty of cabinets and storage

  Linda Covino Royal Shell Real Estate, Inc.

  6787 Pennyroyal Dr, Naples, FL 34114
• 

  

  /47

  $3,800 per month

  • 2 Beds
  • 2 Baths
  • 1,554 Sq Ft
  • Apartment for Rent

  7674 Jacaranda Ln, Naples, FL 34114

  Attached villa in the highly sought after community of Winding Cypress. This home boasts 2 bedrooms plus a en which can be used as a 3rd bedroom, 2 full bathrooms and a 2 car garage. Well maintained and fully furnished including household items (kitchen, linens, etc.) The community is situated off of Collier Blvd close to US41 (Tamiami Trl) which is a 15 minute drive to either downtown Naples

  Michelle Sproviero William Raveis Real Estate

  7674 Jacaranda Ln, Naples, FL 34114
• 

  

  /27

  $530,000 Sold Jun 20, 2025

  • 1,554 Sq Ft
  • $341/SF
  • 229 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 hurricane

  Mike Miller Berkshire Hathaway FL Realty

  7702 Jacaranda Ln, Naples, FL 34114
• 

  

  /36

  Est $672,980 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,554 Sq Ft

  7627 Jacaranda Ln, Naples, FL 34114

  7627 Jacaranda Ln, Naples, FL 34114
• 

  

  /46

  $1,099,000

  • 3 Beds
  • 2 Baths
  • 2,185 Sq Ft

  6767 Pennyroyal Dr, Naples, FL 34114

  Wow! This beautifully designed and meticulously maintained home checks all the right boxes. Featuring the highly desirable Summerwood floor plan with Great Room extension, it is perfect for entertaining or simply relaxing at home after a nice day out in beautiful Naples, FL. The kitchen features upgraded appliances, quartz countertops, an oversized island and walk-in pantry. The two guest

  Jeff Waldman Premiere Plus Realty Company

  6767 Pennyroyal Dr, Naples, FL 34114
• 

  

  /35

  $5,950 per month

  • 3 Beds
  • 2 Baths
  • 2,100 Sq Ft
  • House for Rent

  6856 Winding Cypress Dr, Naples, FL 34114

  Gorgeous kitchen with an oversized island is open to the bright and airy great room as well as your very own private pool and spa! Sliding doors fold all the way back allowing for fabulous inside/outside entertaining. The chef's dream kitchen offers GAS cooking, a huge pantry and counter island seating. Your private pool and spa is heated by gas as well! Be sure to notice the unique lighting

  Maureen Vita Berkshire Hathaway FL Realty

  6856 Winding Cypress Dr, 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
• 

  

  /29

  Est $749,476 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,878 Sq Ft

  7244 Live Oak Dr, Naples, FL 34114

  7244 Live Oak Dr, Naples, FL 34114
• 

  

  /48

  $1,199,000 Open Sun 1PM - 4PM

  • 3 Beds
  • 3 Baths
  • 2,496 Sq Ft

  7520 Blackberry Dr, Naples, FL 34114

  Introducing a luxury estate site 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

  Taylor Smith Premier Sotheby's Int'l Realty

  7520 Blackberry Dr, Naples, FL 34114
• 

  

  /19

  $7,000 per month

  • 2 Beds
  • 2 Baths
  • 1,654 Sq Ft
  • House for Rent

  6787 Winding Cypress Dr, Naples, FL 34114

  Home away from home! Enjoy a newly built, barely lived in home, in one of the most amenity rich communities in all of Naples. Featuring 2 Bedrooms + Den, 2 Full Bathrooms, screened-in lanai, 10' foot ceilings, and a large open floor plan, this property has everything one needs in order to ensure a relaxing, comfortable, and entertaining/active stay. Winding Cypress is a vibrant community offering

  Ryan Gaumer William Raveis Real Estate

  6787 Winding Cypress Dr, 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, PAVER SIDEWALKS

  Theresa Bocka William Raveis Real Estate

  6854 Greenbriar Ct, Naples, FL 34114
• 

  

  /39

  Est $908,792 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,089 Sq Ft

  6828 Winding Cypress Dr, Naples, FL 34114

  6828 Winding Cypress Dr, Naples, FL 34114
• 

  

  /30

  $949,000

  • 3 Beds
  • 2 Baths
  • 2,188 Sq Ft

  7451 Blackberry Dr, Naples, FL 34114

  Located in the highly sought-after community of Winding Cypress, this beautifully updated 3-bedroom, 2-bath home offers a perfect blend of luxury, comfort, and breathtaking lake views. Surrounded by 800 acres of natural preserve and 80 acres of serene lakes, this home provides a tranquil lifestyle immersed in nature, with access to all the incredible amenities this community has to offer.Inside,

  Brandi Chapman Downing Frye Realty Inc.

  7451 Blackberry Dr, Naples, FL 34114
• 

  

  /50

  $9,500 per month

  • 3 Beds
  • 3 Baths
  • 2,272 Sq Ft
  • House for Rent

  6779 Pennyroyal Dr, Naples, FL 34114

  A stunning new pool and outdoor lanai, complement this exquisitely designed home, which offers tranquil views of the lake. This property features three bedrooms plus a den and three bathrooms, making it ideal for vacationing. The interior boasts a bright and airy coastal contemporary style with an open floor plan.This is a perfect vacation rental!

  Patricia Moreno Naples Homes and Rentals Inc

  6779 Pennyroyal 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
• 

  

  /41

  Est $1,564,247 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,515 Sq Ft

  6880 Cocoplum St, Naples, FL 34114

  6880 Cocoplum St, Naples, FL 34114
• 

  

  /46

  $1,000,000 Open Sun 1PM - 4PM

  • 3 Beds
  • 2 Baths
  • 2,186 Sq Ft

  7679 Winding Cypress Dr, Naples, FL 34114

  Imagine waking up each morning in your dream home,Nestled in one of Naples' most sought-after gated communities. As you walk into this beautiful home you are greeted with the open-concept floor plan that welcomes you, with the warmth of granite countertops and the added upgrades of a gas stove and wall oven in your chef-inspired kitchen. Your home is more than just a place to live, it’s a

  Joseph Bartos Premiere Plus Realty Company

  7679 Winding Cypress Dr, Naples, FL 34114
• 

  

  /29

  $12,000 per month

  • 3 Beds
  • 2 Baths
  • 1,805 Sq Ft
  • House for Rent

  7567 Winding Cypress Dr, Naples, FL 34114

  From the moment you arrive at the stunning entry, Winding Cypress invites you into this wonderful community. This natural gas, resort-style community, remaining almost 2/3 preserve, welcomes you with a streetscape of superb views and new homes designed for the way you live. This premier Naples location offers highly attractive fees for the variety of world-class amenities right in your own

  Dave Garafola Reed Property Mgt. & Sales

  7567 Winding Cypress Dr, 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
• 

  

  /50

  Est $1,009,981 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
• 

  

  /47

  $975,000 Open Sun 1PM - 4PM

  • 3 Beds
  • 2 Baths
  • 2,094 Sq Ft

  6699 Pennyroyal Dr, Naples, FL 34114

  Welcome to this Winding Cypress beauty! Why wait months to build and spend twice as much to get less in a home and amenities. This 2022 built classic Mystique Model has everything you'll ever need in a home and is located in Naples best hidden secret.....Winding Cypress! Located on a private, quiet, dead-end cul-de-sac, this home has many builder upgrades. The home is impeccably decorated and

  Theresa Bocka William Raveis Real Estate

  6699 Pennyroyal Dr, Naples, FL 34114
• 

  

  /35

  $8,500 per month

  • 3 Beds
  • 2 Baths
  • 2,175 Sq Ft
  • House for Rent

  6694 Pennyroyal Dr, Naples, FL 34114

  Unwind in this brand new, pristine vacation rental. Revel in the allure of a splendid pet-friendly home with a dazzling outdoor lanai, designed for the ultimateoutdoor living experience. This residence boasts abundant natural light, a refreshing coastal contemporary interior, and an inviting open floor plan. With three bedrooms plus a versatile office you'll have ample space to accommodate

  Jocelyn Lujen Coldwell Banker Realty

  6694 Pennyroyal Dr, 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
• 

  

  /48

  Est $1,027,204 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,107 Sq Ft

  6846 Greenbriar Ct, Naples, FL 34114

  6846 Greenbriar Ct, Naples, FL 34114
• 

  

  /49

  $985,000 Open Sun 1PM - 4PM

  • 3 Beds
  • 3 Baths
  • 2,158 Sq Ft

  6754 Pennyroyal Dr, Naples, FL 34114

  From the moment you drive into the beautiful community of Winding Cypress you will feel welcomed. The stunning entry to this picturesque enclave will be a place you can truly call HOME! This is a natural gas, resort-style community, with over 2/3rds of the neighborhood remaining a preserve! You are surrounded by nature, yet close to wonderful dining options, gourmet grocers, and lots of fun

  Chip Harris Coldwell Banker Realty

  6754 Pennyroyal Dr, Naples, FL 34114
• 

  

  /43

  $7,000 per month

  • 2 Beds
  • 2 Baths
  • 1,542 Sq Ft
  • Condo for Rent

  7631 Jacaranda Ln, Naples, FL 34114

  Beautiful two bedroom plus den, two bath attached villa pool home in the amenity rich gated community of Winding Cypress. Main bedroom has a king bed, second bedroom has a queen bed and den has a full size pullout couch that sleeps 2 and includes a full wardrobe armor for clothing . Spacious attached 2-car garage. Relax on the spacious lanai that overlooks the private pool with peaceful lake

  Amber Jasper Grice Realty Inc

  7631 Jacaranda Ln, 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
• 

  

  /34

  Est $1,004,245 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,094 Sq Ft

  6723 Pennyroyal Dr, Naples, FL 34114

  6723 Pennyroyal Dr, Naples, FL 34114
• 

  

  /46

  $999,900

  • 3 Beds
  • 2 Baths
  • 2,198 Sq Ft

  7355 Mockingbird Ct, Naples, FL 34114

  Welcome to your new home in Winding Cypress, a vibrant community in the heart of Southeast Naples. Surrounded by 800 acres of lush preserves and 80 acres of peaceful lakes, this is the ideal setting to enjoy a serene, nature-filled lifestyle. Yet, with Downtown Naples and the iconic 5th Avenue—one of America’s most beautiful streets—just 20 minutes away, you’ll always be close to the best of city

  Mike Zecchino The Agency Naples

  7355 Mockingbird Ct, Naples, FL 34114
• 

  

  /25

  $12,000 per month

  • 3 Beds
  • 3 Baths
  • 2,128 Sq Ft
  • House for Rent

  6770 Pennyroyal Dr, Naples, FL 34114

  This newly completed and spacious PET FRIENDLY home offers 3 bedrooms (King, King & 2 Twins) plus a den that is equipped with a queen-size murphy bed. This home is full of entertaining options that allow you to bring the extended family along. With its open floor plan as well as zero-corner sliders that blend the interior seating with the outside kitchen and bar. As soon as you drive through the

  Ryan Buchalter William Raveis Real Estate

  6770 Pennyroyal 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
• 

  

  /43

  Est $1,042,785 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,884 Sq Ft

  6762 Pennyroyal Dr, Naples, FL 34114

  6762 Pennyroyal Dr, Naples, FL 34114

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