$940,000
$210K PRICE DROP
- 4 Beds
- 3 Baths
- 3,036 Sq Ft
6825 Greenbriar Ct, Naples, FL 34114
Theresa Bocka
William Raveis Real Estate
(239) 488-2755
912
Winding Cypress Homes
-
6825 Greenbriar Ct, Naples, FL 34114
-
$7,000 Per Month
- 2 Beds
- 2 Baths
- 1,542 Sq Ft
- House for Rent
7631 Jacaranda Ln, Naples, FL 34114
7631 Jacaranda Ln, Naples, FL 34114Beautiful 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
-
$905,000
Sold May 22, 20267545 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 $975,204
Last Listing Agent Nina Llorca Coldwell Banker Realty
7545 Geranium Way, Naples, FL 34114 -
Est $565,525
Not Listed For Sale7694 Jacaranda Ln, Naples, FL 34114
- 2 Beds
- 2 Baths
- 1,554 Sq Ft
- Built 2019
Last Sold Summary
- 58 Days On Market
-
$949,900
- 3 Beds
- 2 Baths
- 2,100 Sq Ft
6844 Winding Cypress Dr, Naples, FL 34114
6844 Winding Cypress Dr, Naples, FL 34114Linda Covino Royal Shell Real Estate, Inc.
-
$3,500 Per Month
- 2 Beds
- 2 Baths
- 1,555 Sq Ft
- House for Rent
7662 Jacaranda Ln, Naples, FL 34114
7662 Jacaranda Ln, Naples, FL 34114Property Id: 957106Escape from stress in this clean, like-new ELEGANT POOL VILLA, completely updated & FURNISHED. Incomparably upgraded for our discriminating guests. #Lease Options||Available June 2026||6-Month Lease June - Nov 2026$3,500/month + utilities||6-10-Month Lease Spanning High Season$4,347/month + utilities||11-12-Month
(708) 998-5200
-
$1,260,000
Sold Nov 21, 20256839 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 $1,275,623
Last Listing Agent Kendra Hoefs Realty One Group MVP
6839 Winding Cypress Dr, Naples, FL 34114 -
Est $1,040,362
Not Listed For Sale7628 Winding Cypress Dr, Naples, FL 34114
- 3 Beds
- 3 Baths
- 2,496 Sq Ft
- Built 2018
Last Sold Summary
- 63 Days On Market
-
$935,000
- 3 Beds
- 2 Baths
- 2,076 Sq Ft
6787 Pennyroyal Dr, Naples, FL 34114
6787 Pennyroyal Dr, Naples, FL 34114Michelle Thomas Premier Sotheby's International Realty
-
$3,800 Per Month
- 2 Beds
- 2 Baths
- 1,554 Sq Ft
- Apartment for Rent
7674 Jacaranda Ln, Naples, FL 34114
7674 Jacaranda Ln, Naples, FL 34114Available after July 10th, 2026: 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
Michelle Sproviero William Raveis Real Estate
-
$635,000
Sold Apr 09, 20267717 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 $630,040
Last Listing Agent Kendra Hoefs Realty One Group MVP
7717 Jacaranda Ln, Naples, FL 34114 -
Est $624,863
Not Listed For Sale7682 Jacaranda Ln, Naples, FL 34114
- 2 Beds
- 2 Baths
- 1,594 Sq Ft
- Built 2018
Last Sold Summary
- 104 Days On Market
-
$585,000
$15K PRICE DROP Pending- 2 Beds
- 2 Baths
- 1,554 Sq Ft
7733 Jacaranda Ln, Naples, FL 34114
7733 Jacaranda Ln, Naples, FL 34114Jeff Waldman Premiere Plus Realty Company
-
$11,500 Per Month
- 3 Beds
- 2 Baths
- 1,805 Sq Ft
- House for Rent
7567 Winding Cypress Dr, Naples, FL 34114
7567 Winding Cypress Dr, Naples, FL 34114From 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
-
$580,000
Sold Jun 12, 20267121 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 $588,816
Last Listing Agent Julie Blanton John R Wood Properties
7121 Live Oak Dr, Naples, FL 34114 -
Est $842,137
Not Listed For Sale7556 Winding Cypress Dr, Naples, FL 34114
- 3 Beds
- 2 Baths
- 2,107 Sq Ft
- Built 2018
Last Sold Summary
- 3 Days On Market
-
$1,099,000
Pending- 4 Beds
- 2 Baths
- 2,186 Sq Ft
7631 Winding Cypress Dr, Naples, FL 34114
7631 Winding Cypress Dr, Naples, FL 34114Jeff Waldman Premiere Plus Realty Company
-
$10,500 Per Month
- 3 Beds
- 2 Baths
- 2,185 Sq Ft
- House for Rent
6767 Pennyroyal Dr, Naples, FL 34114
6767 Pennyroyal Dr, Naples, FL 34114Beautifully 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
-
$625,000
Sold Apr 14, 20267057 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 $643,334
Last Listing Agent Craig Jerabeck Premiere Plus Realty Company
7057 Live Oak Dr, Naples, FL 34114 -
Est $597,844
Not Listed For Sale7627 Jacaranda Ln, Naples, FL 34114
- 2 Beds
- 2 Baths
- 1,554 Sq Ft
- Built 2017
Last Sold Summary
- 91 Days On Market
-
$499,900
$129K PRICE DROP Pending- 2 Beds
- 2 Baths
- 1,574 Sq Ft
7638 Jacaranda Ln, Naples, FL 34114
7638 Jacaranda Ln, Naples, FL 34114Taylor Smith Premier Sotheby's Int'l Realty
-
$8,000 Per Month
- 4 Beds
- 3 Baths
- 2,461 Sq Ft
- House for Rent
7103 Lily Way, Naples, FL 34114
7103 Lily Way, Naples, FL 34114Beautiful turnkey furnished single-family home in the sought-after gated community of Winding Cypress, available now in the off-season or during season. 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
Maria Sloboda Downing Frye Realty Inc.
-
$1,175,000
Sold Sep 22, 20257597 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 $1,199,129
Last Listing Agent Robert Crovo Premier Sotheby's Int'l Realty
7597 Blackberry Dr, Naples, FL 34114 -
Est $638,364
Not Listed For Sale7256 Live Oak Dr, Naples, FL 34114
- 3 Beds
- 2 Baths
- 1,685 Sq Ft
- Built 2015
Last Sold Summary
- 20 Days On Market
-
$960,000
Open Sun 1PM - 4PM- 3 Beds
- 2 Baths
- 2,076 Sq Ft
6727 Pennyroyal Dr, Naples, FL 34114
6727 Pennyroyal Dr, Naples, FL 34114Kendra Hoefs Realty One Group MVP
-
$15,000 Per Month
- 4 Beds
- 3 Baths
- 3,077 Sq Ft
- House for Rent
7763 Winding Cypress Dr, Naples, FL 34114
7763 Winding Cypress Dr, Naples, FL 34114Seasonal 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
-
$875,000
Sold Dec 15, 20257355 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 $879,319
Last Listing Agent Kendra Hoefs Realty One Group MVP
7355 Mockingbird Ct, Naples, FL 34114 -
Est $1,264,252
Not Listed For Sale6883 Cocoplum St, Naples, FL 34114
- 3 Beds
- 3 Baths
- 2,519 Sq Ft
- Built 2021
Last Sold Summary
- 56 Days On Market
-
$750,000
$50K PRICE DROP- 3 Beds
- 2 Baths
- 2,078 Sq Ft
7022 Live Oak Dr, Naples, FL 34114
7022 Live Oak Dr, Naples, FL 34114Kathy Friedle John R. Wood Properties
-
$9,000 Per Month
- 2 Beds
- 2 Baths
- 1,685 Sq Ft
- House for Rent
7052 Live Oak Dr, Naples, FL 34114
7052 Live Oak Dr, Naples, FL 34114LUXURY 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
-
$530,000
Sold Jun 23, 20257702 Jacaranda Ln, Naples, FL 34114
- 2 Beds
- 2 Baths
- 1,554 Sq Ft
- Built 2019
Last Sold Summary
- 4% Below List Price
- $341/SF
- 0 Days On Market
Current Estimated Value $546,111
Last Listing Agent Comp Agent Marco Island Area Association Of Realtor
7702 Jacaranda Ln, Naples, FL 34114 -
Est $731,852
Not Listed For Sale7244 Live Oak Dr, Naples, FL 34114
- 2 Beds
- 2 Baths
- 1,878 Sq Ft
- Built 2016
Last Sold Summary
- 17 Days On Market
-
$975,000
Pending- 3 Beds
- 2 Baths
- 2,107 Sq Ft
7343 Mockingbird Ct, Naples, FL 34114
7343 Mockingbird Ct, Naples, FL 34114Kendra Hoefs Realty One Group MVP
-
$550,000
Sold Mar 30, 20267785 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 $548,370
Last Listing Agent Taylor Smith Premier Sotheby's Int'l Realty
7785 Jacaranda Ln, Naples, FL 34114 -
Est $768,238
Not Listed For Sale6758 Pennyroyal Dr, Naples, FL 34114
- 2 Beds
- 2 Baths
- 1,921 Sq Ft
- Built 2021
Last Sold Summary
- 52 Days On Market
-
$1,349,500
- 3 Beds
- 3 Baths
- 2,634 Sq Ft
7478 Winding Cypress Dr, Naples, FL 34114
7478 Winding Cypress Dr, Naples, FL 34114Austin Kellam Coldwell Banker Realty
-
$855,000
Sold Jul 11, 20256906 Winding Cypress Dr, Naples, FL 34114
- 3 Beds
- 3 Baths
- 2,124 Sq Ft
- Built 2022
Last Sold Summary
- 14% Below List Price
- $403/SF
- 103 Days On Market
Current Estimated Value $892,239
Last Listing Agent Terence Trombetti Berkshire Hathaway FL Realty
6906 Winding Cypress Dr, Naples, FL 34114 -
Est $861,553
Not Listed For Sale6763 Pennyroyal Dr, Naples, FL 34114
- 3 Beds
- 2 Baths
- 2,208 Sq Ft
- Built 2020
Last Sold Summary
- 66 Days On Market
-
$834,999
$64K PRICE DROP Pending- 3 Beds
- 2 Baths
- 2,188 Sq Ft
7460 Blackberry Dr, Naples, FL 34114
7460 Blackberry Dr, Naples, FL 34114Angelica Andrews Premier Sotheby's International Realty
-
$975,000
Sold Sep 09, 20257788 Winding Cypress Dr, Naples, FL 34114
- 3 Beds
- 3 Baths
- 2,496 Sq Ft
- Built 2019
Last Sold Summary
- 37% Below List Price
- $391/SF
- 293 Days On Market
Current Estimated Value $1,027,800
Last Listing Agent Justine Hine John R. Wood Properties
7788 Winding Cypress Dr, Naples, FL 34114
Showing Results 1 - 40, Page 1 of 18
Home Prices in Winding Cypress, FL
The median home sale price in Winding Cypress, Naples is $835,000, down 2% year-over-year. Homes in Winding Cypress sell in 139 days on average, compared to the national average of 58 days.
Home Price Trends
|
Median Sale Price
$835,000
|
Median Single Family Sale Price
$858,500
|
|
Median Townhouse Sale Price
$577,500
|
Median 2 Bedroom Sale Price
$587,500
|
|
Average Price Per Sq Ft
$411
|
Number of Homes for Sale
8
|
|
Last 12 months Home Sales
107
|
Months of Supply
0.90
|
|
Median List Price
$900,000
|
Median Change From 1st List Price
8%
|
|
Median Home Sale Price YoY Change
-2%
|
|
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