Winding Cypress Homes

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  /48

  $1,190,000 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

  (239) 396-4003

  7520 Blackberry Dr, Naples, FL 34114
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  Explore Winding Cypress

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  /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

  (239) 758-7803

  6779 Pennyroyal Dr, Naples, FL 34114
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  /33

  $750,000 Sold Sep 10, 2025

  • 1,685 Sq Ft
  • $445/SF
  • 143 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2015

  7128 Lily Way, Naples, FL 34114

  Thoughtful price improvements, upgraded finishes throughout, an expanded kitchen island & a rare 4-foot extension in the garage sets this home apart - topped off by a stunning private pool overlooking the lake. This property offers exceptional appeal. This is a stunning Abbeyville home in Winding Cypress, a move-in ready! This immaculate residence is a must-see, featuring a fresh neutral palette,

  Kate Pentelow Premiere Plus Realty Company

  7128 Lily Way, Naples, FL 34114
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  /46

  Est $596,716 Not Listed For Sale

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

  7694 Jacaranda Ln, Naples, FL 34114

  7694 Jacaranda Ln, Naples, FL 34114
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  /50

  $825,000

  • 3 Beds
  • 2 Baths
  • 2,230 Sq Ft

  7049 Live Oak Dr, Naples, FL 34114

  Enjoy resort-style living in this Winding Cypress community near 5th Avenue and Marco Island. This home features a private pool, sunroom and the community’s largest covered lanai. Designed for year-round comfort, it offers a new air-conditioning system with additional cooling in the primary suite, impact glass throughout, and natural gas for efficiency and gourmet cooking. Inside, the oversized

  

  Taylor Smith

  Premier Sotheby's Int'l Realty

  (239) 392-1442

  7049 Live Oak Dr, Naples, FL 34114
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  /41

  $8,000 per month

  • 3 Beds
  • 2 Baths
  • 2,086 Sq Ft
  • House for Rent

  6718 Pennyroyal Dr, Naples, FL 34114

  ** NICELY FURNISHED 3 BEDROOM PLUS A DEN - BATH SINGLE FAMILY HOME IN WINDING CYPRESS WITH RESORT-STYLE LIVING IN NAPLES, FLORIDA ** LONG-TERM TENANT FOR OCTOBER 2025 OR SEASONAL TENANT READY ** BEST AMENITIES AT WINDING CYPRESS **Welcome to Winding Cypress, one of Naples' premier gated communities, where luxury meets nature and every day feels like a vacation. This beautifully furnished

  Cheri Anne DeMonico Premier Property Management

  6718 Pennyroyal Dr, Naples, FL 34114
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  /46

  $975,000 Sold Sep 09, 2025

  • 2,496 Sq Ft
  • $391/SF
  • 293 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 2019

  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 John R. Wood Properties

  7788 Winding Cypress Dr, Naples, FL 34114
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  /50

  Est $1,131,876 Not Listed For Sale

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

  7628 Winding Cypress Dr, Naples, FL 34114

  7628 Winding Cypress Dr, Naples, FL 34114
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  /48

  $529,000

  • 2 Beds
  • 2 Baths
  • 1,574 Sq Ft

  7638 Jacaranda Ln, Naples, FL 34114

  Introducing the incredibly rare Winding Cypress model, the Cressida villa, now available with expansive private yard and lanai space. This unique villa features a dedicated private front entrance and an expanded foyer, complemented by an open yet defined living concept. The home boasts a wealth of builder-installed upgrades, including granite finishes, high-end porcelain floors, a glass-tiled

  

  Taylor Smith

  Premier Sotheby's Int'l Realty

  (239) 539-4020

  7638 Jacaranda Ln, Naples, FL 34114
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  /49

  $6,500 per month

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

  7627 Jacaranda Ln, Naples, FL 34114

  Light, bright and beautifully updated 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 size bed and den has a queen size Murphy bed. Spacious attached 2-car garage. Water filter system purifies all water throughout the villa. Sit back and relax with your coffee in the morning or

  Amber Jasper Grice Realty Inc

  7627 Jacaranda Ln, Naples, FL 34114
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  /49

  $674,000 Sold Aug 19, 2025

  • 2,198 Sq Ft
  • $307/SF
  • 65 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2016

  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

  7445 Winding Cypress Dr, Naples, FL 34114
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  /44

  Est $676,473 Not Listed For Sale

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

  7682 Jacaranda Ln, Naples, FL 34114

  7682 Jacaranda Ln, Naples, FL 34114
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  /50

  $665,000 Pending

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

  7773 Jacaranda Ln, Naples, FL 34114

  On a premium oversized lot, this beautifully upgraded villa offers one of the most stunning sunset water views in all of Winding Cypress. The extended screened lanai features a panoramic no-see-um screen, heated saltwater pool, and a fully equipped outdoor kitchen with a five-burner Bull Grill, stainless steel sink, premium refrigerator, and a 42-inch lighted vent hood, an entertainer’s dream and

  

  Taylor Smith

  Premier Sotheby's Int'l Realty

  (239) 448-8471

  7773 Jacaranda Ln, Naples, FL 34114
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  /46

  $6,800 per month

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

  7631 Jacaranda Ln, Naples, FL 34114

  Beautiful two bedrooms 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 armoire for clothing . Spacious attached 2-car garage. Relax on the spacious lanai that overlooks the private pool and peaceful lake

  Amber Jasper Grice Realty Inc

  7631 Jacaranda Ln, Naples, FL 34114
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  /50

  $880,000 Sold Aug 18, 2025

  • 2,107 Sq Ft
  • $418/SF
  • 272 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2021

  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. The heart of the home is a spacious, light-filled living area and a large kitchen with

  Ryan Finnegan Coldwell Banker Sunstar Realty

  6763 Winding Cypress Dr, Naples, FL 34114
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  /36

  Est $641,140 Not Listed For Sale

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

  7627 Jacaranda Ln, Naples, FL 34114

  7627 Jacaranda Ln, Naples, FL 34114
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  /36

  $950,000

  • 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
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  /49

  $12,000 per month

  • 3 Beds
  • 3 Baths
  • 2,158 Sq Ft
  • House for Rent

  6754 Pennyroyal Dr, Naples, FL 34114

  AVAILABLE FOR 2026 SEASON!! Step into paradise! ONE SMALL DOG ALLOWED! Built in 2021, this newly decorated and spacious pool home offers 3 bedrooms (King, King & 2 Twins) plus a den and 3 FULL bathrooms. Features include a wonderful open floor plan with zero-corner sliders that bring the outside in! Fabulous screened-in area with heated pool, natural gas, stainless appliances, quartz counters,

  Sam Wells Coldwell Banker Realty

  6754 Pennyroyal Dr, Naples, FL 34114
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  /11

  $830,000 Sold Aug 08, 2025

  • 2,532 Sq Ft
  • $328/SF
  • 253 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 2018

  7544 Winding Cypress Dr, Naples, FL 34114

  Welcome to a beautiful Pinnacle Model in the desirable, amenity rich community of Winding Cypress. This waterfront home. Original owner care is apparent throughout. Builder and owner upgrades include; chef's kitchen with upgraded appliances, sink & faucet, soft close pull out cabinets including under-side lighting, custom quartz countertops, custom plank tile flooring, hurricane impact windows,

  Theresa Bocka William Raveis Real Estate

  7544 Winding Cypress Dr, Naples, FL 34114
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  /29

  Est $737,595 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
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  /37

  $899,000

  • 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
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  /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
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  /48

  $900,000 Sold Aug 07, 2025

  • 1,901 Sq Ft
  • $473/SF
  • 23 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2021

  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
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  /50

  Est $642,433 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,544 Sq Ft

  7611 Jacaranda Ln, Naples, FL 34114

  7611 Jacaranda Ln, Naples, FL 34114
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  /40

  $979,900 Open Sun 1PM - 3PM

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

  6787 Pennyroyal Dr, Naples, FL 34114

  Beautiful 2022 mystique model contemporary home.long corner private lot , beautiful long lake view on one of the largest lakes in WC. Ready for imediate occupancy most furniture has been removed. marble design tile floor, custom wood moldings & beams in trey ceiling in gathering room, upgraded kitchen back splash and faucet ,custom molding in foyer , Custom wall design in master bedroom ,

  Linda Covino Royal Shell Real Estate, Inc.

  6787 Pennyroyal Dr, Naples, FL 34114
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  /35

  $8,500 per month

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

  6694 Pennyroyal Dr, Naples, FL 34114

  ONLY AVAILABLE DURING OFF SEASON.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 ultimate outdoor 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

  Ashley Baird Coldwell Banker Realty

  6694 Pennyroyal Dr, Naples, FL 34114
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  /30

  $885,000 Sold Aug 07, 2025

  • 2,188 Sq Ft
  • $404/SF
  • 82 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2017

  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

  Brandi Chapman Downing Frye Realty Inc.

  7451 Blackberry Dr, Naples, FL 34114
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  /39

  Est $865,801 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
• 

  

  /43

  $885,000

  • 3 Beds
  • 2 Baths
  • 2,230 Sq Ft

  7211 Live Oak Dr, Naples, FL 34114

  Experience Your Best Life at Winding Cypress! Ready to live like you're on vacation every single day? This isn't just a home; it's your personal retreat in the highly sought-after Winding Cypress community. This spectacular Summerville Extended model is meticulously designed for those who crave the perfect blend of resort-style luxury and sophisticated comfort.Imagine waking up to

  Felicia Saraceno eXp Realty LLC

  7211 Live Oak Dr, Naples, FL 34114
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  /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
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  /41

  Est $1,392,703 Not Listed For Sale

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

  6880 Cocoplum St, Naples, FL 34114

  6880 Cocoplum St, Naples, FL 34114
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  /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
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  /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
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  /50

  Est $989,237 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
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  /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
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  /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
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  /48

  Est $1,010,140 Not Listed For Sale

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

  6846 Greenbriar Ct, Naples, FL 34114

  6846 Greenbriar Ct, Naples, FL 34114
• 

  

  /25

  $1,099,000 Pending

  • 3 Beds
  • 3 Baths
  • 2,512 Sq Ft

  7235 Clamshell Ln, Naples, FL 34114

  Location, location! This meticulously maintained and decorated Pinnacle model located on a corner lot with privacy on both sides including a lake and wooded area view is unique! Conveniently located within walking distance to clubhouse! The home features 3 bedrooms plus a den, 3 full baths and 3 car garage in this highly sought after natural gas community of Winding Cypress! This large lanai

  Tommy Ogiba Downing Frye Realty Inc.

  7235 Clamshell Ln, Naples, FL 34114
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  /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
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  /34

  Est $991,400 Not Listed For Sale

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

  6723 Pennyroyal Dr, Naples, FL 34114

  6723 Pennyroyal Dr, Naples, FL 34114

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