$599,900
Open Sun 1PM - 4PM
- 3 Beds
- 2 Baths
- 1,554 Sq Ft
7156 Live Oak Dr, Naples, FL 34114
Theresa Bocka
William Raveis Real Estate
889
Winding Cypress Homes
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7156 Live Oak Dr, Naples, FL 34114
-
$3,330 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: 957106 Escape to this clean, like-new EXECUTIVE POOL VILLA, completely updated & FURNISHED. Incomparably upgraded for our discriminating guests. ==== SEPTEMBER 2026 AND ANNUAL OPTIONS STARTING JULY 2027 === || SHORT-TERM RATE: FEES, UTILITIES, AND TAXES APPLY. 1-Month $3,330 (a) SEPTEMBER 2026 ONLY (b) PROMO: 1-month September lease
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$1,025,000
Sold Jun 25, 20267631 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 $1,030,841
Last Listing Agent Comp Agent Marco Island Area Association Of Realtor
7631 Winding Cypress Dr, Naples, FL 34114 -
Est $550,885
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
Last Listing Agent Jim Cunnyngham Premier Sotheby's Int'l Realty
-
$1,200,000
Pending- 3 Beds
- 3 Baths
- 2,789 Sq Ft
6851 Winding Cypress Dr, Naples, FL 34114
6851 Winding Cypress Dr, Naples, FL 34114
Theresa Bocka
William Raveis Real Estate
-
$7,000 Per Month
- 2 Beds
- 2 Baths
- 1,542 Sq Ft
- Apartment 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
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$565,000
Sold Jul 14, 20267733 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 $563,911
Last Listing Agent Jeff Waldman Premiere Plus Realty Company
7733 Jacaranda Ln, Naples, FL 34114 -
Est $1,048,597
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
Last Listing Agent Gabriele H. Vretta John R Wood Properties
-
$1,300,000
Open Sun 1PM - 4PM $100K PRICE DROP- 4 Beds
- 4.5 Baths
- 3,464 Sq Ft
7759 Winding Cypress Dr, Naples, FL 34114
7759 Winding Cypress Dr, Naples, FL 34114
Theresa Bocka
William Raveis Real Estate
-
$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
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$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 $915,709
Last Listing Agent Nina Llorca Coldwell Banker Realty
7545 Geranium Way, Naples, FL 34114 -
Est $611,175
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
Last Listing Agent Kimberly Hill Schulz Realty LLC
-
$940,000
$20K PRICE DROP- 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
-
$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.
-
$1,260,000
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 $1,275,556
Last Listing Agent Kendra Hoefs Realty One Group MVP
6839 Winding Cypress Dr, Naples, FL 34114 -
Est $854,853
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
Last Listing Agent Kimberly Springer Orchid Realty International
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$1,250,000
- 54 Beds
- 3 Baths
- 2,950 Sq Ft
7700 Winding Cypress Dr, Naples, FL 34114
7700 Winding Cypress Dr, Naples, FL 34114Tim Sykes Anchor Real Estate
-
$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
-
$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 $636,665
Last Listing Agent Kendra Hoefs Realty One Group MVP
7717 Jacaranda Ln, Naples, FL 34114 -
Est $604,949
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
Last Listing Agent Frank Schultz Premiere Plus Realty Company
-
$599,900
Pending- 2 Beds
- 2 Baths
- 1,554 Sq Ft
7674 Jacaranda Ln, Naples, FL 34114
7674 Jacaranda Ln, Naples, FL 34114Michelle Sproviero William Raveis Real Estate
-
$14,500 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 March and April 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
Melanie Listrom REMAX Affinity Mercato
-
$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 $575,389
Last Listing Agent Julie Blanton John R Wood Properties
7121 Live Oak Dr, Naples, FL 34114 -
Est $659,476
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
Last Listing Agent Gabriele H. Vretta John R Wood Properties
-
$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
-
$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
-
$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 $661,317
Last Listing Agent Craig Jerabeck John R Wood Properties
7057 Live Oak Dr, Naples, FL 34114 -
Est $893,265
Not Listed For Sale7451 Blackberry Dr, Naples, FL 34114
- 3 Beds
- 2 Baths
- 2,188 Sq Ft
- Built 2017
Last Sold Summary
- 82 Days On Market
Last Listing Agent Brandi Chapman Downing Frye Realty Inc.
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$799,900
Pending- 3 Beds
- 2 Baths
- 2,086 Sq Ft
6820 Winding Cypress Dr, Naples, FL 34114
6820 Winding Cypress Dr, Naples, FL 34114Linda Covino Royal Shell Real Estate, 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 $1,198,359
Last Listing Agent Robert Crovo Premier Sotheby's Int'l Realty
7597 Blackberry Dr, Naples, FL 34114 -
Est $1,276,525
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
Last Listing Agent Theresa Bocka William Raveis Real Estate
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$1,295,000
- 3 Beds
- 3 Baths
- 2,515 Sq Ft
6907 Cocoplum St, Naples, FL 34114
6907 Cocoplum St, Naples, FL 34114Michael Dorobanti Compass Florida LLC
-
$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 $884,953
Last Listing Agent Kendra Hoefs Realty One Group MVP
7355 Mockingbird Ct, Naples, FL 34114 -
Est $747,222
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
Last Listing Agent Jeri Neuhaus Premiere Plus Realty Company
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$575,000
- 2 Beds
- 2 Baths
- 1,574 Sq Ft
7666 Jacaranda Ln, Naples, FL 34114
7666 Jacaranda Ln, Naples, FL 34114Susan Heller EXP Realty LLC
-
$700,000
Sold Aug 07, 20267022 Live Oak Dr, Naples, FL 34114
- 3 Beds
- 2 Baths
- 2,078 Sq Ft
- Built 2016
Last Sold Summary
- 12% Below List Price
- $337/SF
- 123 Days On Market
Current Estimated Value $748,293
Last Listing Agent Kathy Friedle John R. Wood Properties
7022 Live Oak Dr, Naples, FL 34114 -
Est $888,084
Not Listed For Sale6848 Winding Cypress Dr, Naples, FL 34114
- 2 Beds
- 2 Baths
- 1,901 Sq Ft
- Built 2021
Last Sold Summary
- 23 Days On Market
Last Listing Agent Kendra Hoefs Realty One Group MVP
-
$470,000
Sold Jun 24, 20267638 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 $477,822
Last Listing Agent Taylor Smith Premier Sotheby's Int'l Realty
7638 Jacaranda Ln, Naples, FL 34114 -
Est $788,426
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
Last Listing Agent Kendra 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 $553,514
Last Listing Agent Taylor Smith Premier Sotheby's Int'l Realty
7785 Jacaranda Ln, 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 140 days on average, compared to the national average of 55 days.
Home Price Trends
|
Median Sale Price
$835,000
|
Median Single Family Sale Price
$858,500
|
|
Median Townhouse Sale Price
$575,000
|
Median 2 Bedroom Sale Price
$580,000
|
|
Average Price Per Sq Ft
$408
|
Number of Homes for Sale
889
|
|
Last 12 months Home Sales
97
|
Months of Supply
0.90
|
|
Median List Price
$899,500
|
Median Change From 1st List Price
8%
|
|
Median Home Sale Price YoY Change
-2%
|
|
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