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Winding Cypress Homes

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  • /31

    $599,900

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

    7156 Live Oak Dr, Naples, FL 34114

    Welcome to your private paradise in the highly sought-after, resort-style community of Winding Cypress! This TURNKEY FURNISHED true 3-bedroom, 2-bathroom villa offers the ultimate blend of luxury, comfort, and effortless living is move-in ready for your immediate enjoyment.The 2-car attached garage—complete with convenient overhead storage racks and additional utility sink—offer great

    Agent Photo

    Theresa Bocka

    William Raveis Real Estate

    7156 Live Oak Dr, Naples, FL 34114
  • /20

    $3,900 Per Month

    • 2 Beds
    • 2 Baths
    • 1,555 Sq Ft
    • House for Rent

    7662 Jacaranda Ln, Naples, FL 34114

    Property Id: 957106 Like-new EXECUTIVE POOL VILLA, completely updated & FURNISHED. Incomparably upgraded in highly sought Winding Cypress! === ANNUAL, MID-TERM, & SHORT-TERM OPTIONS === ANNUAL RATES: FEES, UTILITIES APPLY. TAX-EXEMPT. - 12-Month $4,250/mo - 18-Month $4,150/mo - 24-Month $4,000/mo

    7662 Jacaranda Ln, Naples, FL 34114
  • /2

    $1,025,000

    Sold Jun 25, 2026

    7631 Winding Cypress Dr, Naples, FL 34114

    • 4 Beds
    • 2 Baths
    • 2,186 Sq Ft
    • Built 2018

    Last Sold Summary

    • 7% Below List Price
    • $469/SF
    • 0 Days On Market

    Current Estimated Value $1,076,001

    Last Listing Agent Comp Agent Marco Island Area Association Of Realtor

    7631 Winding Cypress Dr, Naples, FL 34114
    • /11

      Est $507,243

      Not Listed For Sale

      7650 Jacaranda Ln, Naples, FL 34114

      • 2 Beds
      • 2 Baths
      • 1,579 Sq Ft
      • Built 2018
      7650 Jacaranda Ln, Naples, FL 34114

      Last Sold Summary

      • 61 Days On Market

  • /50

    $1,400,000

    • 4 Beds
    • 4.5 Baths
    • 3,464 Sq Ft

    7759 Winding Cypress Dr, Naples, FL 34114

    Welcome to one of the most prestigious, stately, and expansive offerings throughout the entire, always-desirable community of Winding Cypress. This exclusive Stonewater Model, with a full 2nd floor of living space, is a DiVosta Builder's flagship luxury home and a very rare find. This property sits on the most exceptional 1/4 acre lot with a spectacular large lake view and full preserve backdrop

    Agent Photo

    Theresa Bocka

    William Raveis Real Estate

    7759 Winding Cypress Dr, Naples, FL 34114
  • /45

    $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 den 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 or

    Michelle Sproviero William Raveis Real Estate

    7674 Jacaranda Ln, Naples, FL 34114
  • /38

    $565,000

    Sold Jul 14, 2026

    7733 Jacaranda Ln, Naples, FL 34114

    • 2 Beds
    • 2 Baths
    • 1,554 Sq Ft
    • Built 2018

    Last Sold Summary

    • 6% Below List Price
    • $364/SF
    • 101 Days On Market

    Current Estimated Value $581,124

    Last Listing Agent Jeff Waldman Premiere Plus Realty Company

    7733 Jacaranda Ln, Naples, FL 34114
    • /50

      Est $1,246,852

      Not Listed For Sale

      7675 Winding Cypress Dr, Naples, FL 34114

      • 3 Beds
      • 3 Baths
      • 2,496 Sq Ft
      • Built 2020
      7675 Winding Cypress Dr, Naples, FL 34114

      Last Sold Summary

      • 161 Days On Market

  • /47

    $949,900

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

    6844 Winding Cypress Dr, Naples, FL 34114

    Welcome to newest and last phase of homes built in 2020 in the vibrant well maintained community of Winding Cypress. Located just off Collier and 41 and minutes to 75 , Marco Island and downtown NaplesThis summer wood model is sure to please with 3 bdrms den and 2 baths with full showers , primary bath with custom mirrors. custom closet , plantation shutters mini a/c in garage, whole house

    Linda Covino Royal Shell Real Estate, Inc.

    6844 Winding Cypress Dr, Naples, FL 34114
  • /46

    $7,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,542 Sq Ft
    • Apartment 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
  • /50

    $905,000

    Sold May 22, 2026

    7545 Geranium Way, Naples, FL 34114

    • 2 Beds
    • 2 Baths
    • 2,036 Sq Ft
    • Built 2018

    Last Sold Summary

    • 8% Below List Price
    • $444/SF
    • 45 Days On Market

    Current Estimated Value $946,458

    Last Listing Agent Nina Llorca Coldwell Banker Realty

    7545 Geranium Way, Naples, FL 34114
    • /46

      Est $550,785

      Not Listed For Sale

      7694 Jacaranda Ln, Naples, FL 34114

      • 2 Beds
      • 2 Baths
      • 1,554 Sq Ft
      • Built 2019
      7694 Jacaranda Ln, Naples, FL 34114

      Last Sold Summary

      • 58 Days On Market

  • /42

    $940,000

    $20K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,076 Sq Ft

    6727 Pennyroyal Dr, Naples, FL 34114

    This meticulously maintained Mystique features 3 bedrooms + den, 2 bathrooms, 2 car garage with a pool and spa overlooking a lake! This home is situated on a spacious corner lot making it ideal for privacy while maintaining a stunning lake view. The turnkey designer furnishings have hardly been used and it's a pet free home. Outside the private oasis features a spa with waterfall, plenty of

    Kendra Hoefs Realty One Group MVP

    6727 Pennyroyal Dr, Naples, FL 34114
  • /24

    $11,500 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
  • /50

    $1,260,000

    Sold Nov 21, 2025

    6839 Winding Cypress Dr, Naples, FL 34114

    • 3 Beds
    • 3 Baths
    • 2,515 Sq Ft
    • Built 2021

    Last Sold Summary

    • 7% Below List Price
    • $501/SF
    • 76 Days On Market

    Current Estimated Value $1,255,190

    Last Listing Agent Kendra Hoefs Realty One Group MVP

    6839 Winding Cypress Dr, Naples, FL 34114
    • /50

      Est $1,041,165

      Not Listed For Sale

      7628 Winding Cypress Dr, Naples, FL 34114

      • 3 Beds
      • 3 Baths
      • 2,496 Sq Ft
      • Built 2018
      7628 Winding Cypress Dr, Naples, FL 34114

      Last Sold Summary

      • 63 Days On Market

  • /39

    $725,000

    $75K PRICE DROP Pending
    • 3 Beds
    • 2 Baths
    • 2,078 Sq Ft

    7022 Live Oak Dr, Naples, FL 34114

    Welcome to your beautiful Summerwood floor plan home ... Enjoy Florida living in this IMPECCABLY maintained STUNNING home featuring 3 bedrooms, den/sitting room, 2 full bathrooms. Enjoy a spacious living room which is open to the gourmet kitchen featuring a NATURAL GAS range, a large pantry and an island, with ample prep space, for gathering with friends and family. There is tile flooring

    Kathy Friedle John R. Wood Properties

    7022 Live Oak Dr, Naples, FL 34114
  • /46

    $10,500 Per Month

    • 3 Beds
    • 2 Baths
    • 2,185 Sq Ft
    • House for Rent

    6767 Pennyroyal Dr, Naples, FL 34114

    Beautifully furnished 3+Den single family home in the highly sought-after, gated community of Winding Cypress in Naples. This thoughtfully appointed home offers a comfortable and stylish escape, perfect for enjoying the Southwest Florida lifestyle during season. The residence features an open-concept layout filled with natural light, a well-equipped kitchen ideal for entertaining, and inviting

    Lauren Wells Premier Sotheby's Int'l Realty

    6767 Pennyroyal Dr, Naples, FL 34114
  • /44

    $635,000

    Sold Apr 09, 2026

    7717 Jacaranda Ln, Naples, FL 34114

    • 2 Beds
    • 2 Baths
    • 1,554 Sq Ft
    • Built 2017

    Last Sold Summary

    • 4% Below List Price
    • $409/SF
    • 12 Days On Market

    Current Estimated Value $630,340

    Last Listing Agent Kendra Hoefs Realty One Group MVP

    7717 Jacaranda Ln, Naples, FL 34114
    • /44

      Est $600,916

      Not Listed For Sale

      7682 Jacaranda Ln, Naples, FL 34114

      • 2 Beds
      • 2 Baths
      • 1,594 Sq Ft
      • Built 2018
      7682 Jacaranda Ln, Naples, FL 34114

      Last Sold Summary

      • 104 Days On Market

  • /50

    $1,349,500

    • 3 Beds
    • 3 Baths
    • 2,634 Sq Ft

    7478 Winding Cypress Dr, Naples, FL 34114

    BRING OFFERS! Welcome to this highly upgraded Infinity Model, a rare offering in the prestigious Winding Cypress community of Naples. Built by renowned DiVosta Builders, this residence is one of only three Infinity Models within a community of more than 750 homes, making it an exceptionally unique opportunity. Featuring an extra-wide three-car garage with a dedicated third bay ideal for a golf

    Austin Kellam Coldwell Banker Realty

    7478 Winding Cypress Dr, Naples, FL 34114
  • /41

    $4,200 Per Month

    • 4 Beds
    • 3 Baths
    • 2,461 Sq Ft
    • House for Rent

    7103 Lily Way, Naples, FL 34114

    Beautiful turnkey furnished single-family home available now for an annual lease in the sought-after gated community of Winding Cypress. Built in 2015, this spacious residence features 4 bedrooms, 3 bathrooms, and a versatile upstairs loft, offering plenty of room for comfortable living and entertaining. Enjoy an open and inviting floor plan with stylish furnishings and move-in-ready convenience.

    Maria Sloboda Downing Frye Realty Inc.

    7103 Lily Way, Naples, FL 34114
  • /33

    $580,000

    Sold Jun 12, 2026

    7121 Live Oak Dr, Naples, FL 34114

    • 2 Beds
    • 2 Baths
    • 1,554 Sq Ft
    • Built 2016

    Last Sold Summary

    • 8% Below List Price
    • $373/SF
    • 121 Days On Market

    Current Estimated Value $589,134

    Last Listing Agent Julie Blanton John R Wood Properties

    7121 Live Oak Dr, Naples, FL 34114
    • /43

      Est $840,756

      Not Listed For Sale

      7556 Winding Cypress Dr, Naples, FL 34114

      • 3 Beds
      • 2 Baths
      • 2,107 Sq Ft
      • Built 2018
      7556 Winding Cypress Dr, Naples, FL 34114

      Last Sold Summary

      • 3 Days On Market

  • /50

    $834,999

    $64K PRICE DROP Pending
    • 3 Beds
    • 2 Baths
    • 2,188 Sq Ft

    7460 Blackberry Dr, Naples, FL 34114

    Paradise at your fingertips. This modern three-bedroom plus den residence in the prestigious resort style living gated community of Winding Cypress, offers a bright, expansive open floor plan, breathtaking lake views, ceramic tile throughout and a gorgeous and functional updated kitchen featuring solid maple shaker cabinetry, premium hardware, and spacious pantry. This residence is also equipped

    Angelica Andrews Premier Sotheby's International Realty

    7460 Blackberry Dr, Naples, FL 34114
  • /39

    $14,500 Per Month

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

    7763 Winding Cypress Dr, Naples, FL 34114

    Seasonal Rental available for 2027. 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 loft on the

    Melanie Listrom REMAX Affinity Mercato

    7763 Winding Cypress Dr, Naples, FL 34114
  • /43

    $625,000

    Sold Apr 14, 2026

    7057 Live Oak Dr, Naples, FL 34114

    • 3 Beds
    • 2 Baths
    • 2,230 Sq Ft
    • Built 2016

    Last Sold Summary

    • 24% Below List Price
    • $280/SF
    • 152 Days On Market

    Current Estimated Value $645,227

    Last Listing Agent Craig Jerabeck John R Wood Properties

    7057 Live Oak Dr, Naples, FL 34114
    • /36

      Est $595,686

      Not Listed For Sale

      7627 Jacaranda Ln, Naples, FL 34114

      • 2 Beds
      • 2 Baths
      • 1,554 Sq Ft
      • Built 2017
      7627 Jacaranda Ln, Naples, FL 34114

      Last Sold Summary

      • 91 Days On Market

  • /48

    $799,900

    • 3 Beds
    • 2 Baths
    • 2,086 Sq Ft

    6820 Winding Cypress Dr, Naples, FL 34114

    Beautifully upgraded 2021 Mystique model in desirable Phase 3 of Winding Cypress! this 3-bedroom =den home features a custom built in entertainment center with designer gas fireplace ,built in bar, whole-house generator, storm screens, decorative stone exterior, landscape uplighting, and more. the open floor plan with zero corner sliding doors is perfect for entertaining while the private

    Linda Covino Royal Shell Real Estate, Inc.

    6820 Winding Cypress Dr, Naples, FL 34114
  • /50

    $9,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,685 Sq Ft
    • House for Rent

    7052 Live Oak Dr, Naples, FL 34114

    LUXURY WINDING CYPRESS VACATION RENTAL IN NAPLES FLORIDA / BACKYARD OASIS WITH A PRACTICE PUTTING GREEN, INFINITY SPA, FIRE TABLE AND OVERSIZED HEATED POOL. NOW BOOKING SEASON 2027 7052 Live Oak Drive is Your Private Southwest Florida Escape. The ideal home for vacation getaways or extended stays all year round. This 2 Bed, 2 Bath Home with a Den / Office offers 2 King Beds and all the comforts

    Dali Mihajlovic ALL IN PROPERTY MANAGEMENT LLC

    7052 Live Oak Dr, Naples, FL 34114
  • /46

    $1,175,000

    Sold Sep 22, 2025

    7597 Blackberry Dr, Naples, FL 34114

    • 3 Beds
    • 3 Baths
    • 2,496 Sq Ft
    • Built 2017

    Last Sold Summary

    • 9% Below List Price
    • $471/SF
    • 132 Days On Market

    Current Estimated Value $1,161,387

    Last Listing Agent Robert Crovo Premier Sotheby's Int'l Realty

    7597 Blackberry Dr, Naples, FL 34114
    • /42

      Est $653,476

      Not Listed For Sale

      7256 Live Oak Dr, Naples, FL 34114

      • 3 Beds
      • 2 Baths
      • 1,685 Sq Ft
      • Built 2015
      7256 Live Oak Dr, Naples, FL 34114

      Last Sold Summary

      • 20 Days On Market

  • /2

    $575,000

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

    7666 Jacaranda Ln, Naples, FL 34114

    Experience elevated resort-style living in the highly desirable community of Winding Cypress. This impeccably maintained and tastefully updated 2-bedroom plus den, 2-bath villa offers soaring 9’4” ceilings and an attached two-car garage, delivering both comfort and functionality in a truly move-in-ready residence. Thoughtful upgrades include a newer refrigerator and hot water heater, upgraded

    Susan Heller EXP Realty LLC

    7666 Jacaranda Ln, Naples, FL 34114
  • /43

    $875,000

    Sold Dec 15, 2025

    7355 Mockingbird Ct, Naples, FL 34114

    • 3 Beds
    • 2 Baths
    • 2,198 Sq Ft
    • Built 2016

    Last Sold Summary

    • 3% Below List Price
    • $398/SF
    • 4 Days On Market

    Current Estimated Value $873,511

    Last Listing Agent Kendra Hoefs Realty One Group MVP

    7355 Mockingbird Ct, Naples, FL 34114
    • /49

      Est $1,276,426

      Not Listed For Sale

      6883 Cocoplum St, Naples, FL 34114

      • 3 Beds
      • 3 Baths
      • 2,519 Sq Ft
      • Built 2021
      6883 Cocoplum St, Naples, FL 34114

      Last Sold Summary

      • 56 Days On Market

  • /45

    $935,000

    Pending
    • 3 Beds
    • 2 Baths
    • 2,076 Sq Ft

    6787 Pennyroyal Dr, Naples, FL 34114

    On a private corner homesite with breathtaking long lake views, this like-new contemporary residence built in 2022 offers an exceptional blend of style, comfort and modern functionality within the sought-after community of Winding Cypress. Designed with a great room and split-bedroom floor plan, this three-bedroom plus den, two-bath home with a two-car garage showcases light-filled interiors,

    Michelle Thomas Premier Sotheby's Int'l Realty

    6787 Pennyroyal Dr, Naples, FL 34114
  • /48

    $470,000

    Sold Jun 24, 2026

    7638 Jacaranda Ln, Naples, FL 34114

    • 2 Beds
    • 2 Baths
    • 1,574 Sq Ft
    • Built 2017

    Last Sold Summary

    • 25% Below List Price
    • $299/SF
    • 629 Days On Market

    Current Estimated Value $524,363

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

    7638 Jacaranda Ln, Naples, FL 34114
    • /29

      Est $727,109

      Not Listed For Sale

      7244 Live Oak Dr, Naples, FL 34114

      • 2 Beds
      • 2 Baths
      • 1,878 Sq Ft
      • Built 2016
      7244 Live Oak Dr, Naples, FL 34114

      Last Sold Summary

      • 17 Days On Market

  • /50

    $550,000

    Sold Mar 30, 2026

    7785 Jacaranda Ln, Naples, FL 34114

    • 2 Beds
    • 2 Baths
    • 1,574 Sq Ft
    • Built 2018

    Last Sold Summary

    • $349/SF
    • 10 Days On Market

    Current Estimated Value $549,130

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

    7785 Jacaranda Ln, Naples, FL 34114
    • /47

      Est $782,909

      Not Listed For Sale

      6758 Pennyroyal Dr, Naples, FL 34114

      • 2 Beds
      • 2 Baths
      • 1,921 Sq Ft
      • Built 2021
      6758 Pennyroyal Dr, Naples, FL 34114

      Last Sold Summary

      • 52 Days On Market

Showing Results 1 - 40, Page 1 of 18

Home Price Trends

Median Sale Price
$850,000
Median Single Family Sale Price
$858,500
Median Townhouse Sale Price
$577,500
Median 2 Bedroom Sale Price
$595,000
Average Price Per Sq Ft
$409
Number of Homes for Sale
7
Last 12 months Home Sales
105
Months of Supply
0.80
Median List Price
$900,000
Median Change From 1st List Price
8%
Median Home Sale Price YoY Change
0%
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