Winding Cypress Homes

/45
$998,000
- 4 Beds
- 3 Baths
- 3,036 Sq Ft
6825 Greenbriar Ct, Naples, FL 34114

Spacious & Immaculate accurately describe this outstanding retreat in the sought-after community of Winding Cypress. This rare, two-story Mystique footprint boasts 4 bedrooms, 3 full baths, a large den/office, and over 3160 square feet of adjusted living space, 3036 square feet under air. This residence was one of the last built in the community, 3 years new, and shows like a model home. Located

Theresa Bocka

William Raveis Real Estate

(239) 488-2755

6825 Greenbriar Ct, Naples, FL 34114
Explore Winding Cypress
/20
$3,790 per month
- 2 Beds
- 2 Baths
- 1,555 Sq Ft
- House for Rent
7662 Jacaranda Ln, Naples, FL 34114

Property Id: 957106Escape from stress in this clean, like-new ELEGANT POOL VILLA, completely updated & FURNISHED. Incomparably upgraded for our discriminating guests. #Lease Options||Available May 2026||6-12 Month Lease$3,990/month + utilities||14+ Month LeaseBest Value $3,790/month + utilitiesLonger stays enjoy substantially lower monthly

7662 Jacaranda Ln, 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 $1,267,560

Last Listing Agent Kendra Hoefs Realty One Group MVP

6839 Winding Cypress Dr, Naples, FL 34114

/20
Est $559,677 Not Listed For Sale

7591 Jacaranda Ln, Naples, FL 34114
- 2 Beds
- 2 Baths
- 1,554 Sq Ft
- Built 2016
7591 Jacaranda Ln, Naples, FL 34114

Last Sold Summary
- 4% Above List Price
- $346/SF
- 26 Days On Market
- Last Sold Price $537,000
- May 01, 2025
Last Listing Agent william Romano Keller Williams Marco Realty

/14
$615,000 Pending
- 2 Beds
- 2 Baths
- 1,685 Sq Ft
7248 Live Oak Dr, Naples, FL 34114

PRICE IMPROVEMENT - This charming model is the perfect fit featuring an inviting open-floor concept where natural light streams through the windows. The kitchen boasts granite counters, stainless appliances and a center island and extra storage for everyday use and easy entertaining. The pantry closet has plenty of space for all of your staple goods. Tile floors are throughout much of the space.

Theresa Bocka

William Raveis Real Estate

(239) 456-3829

7248 Live Oak 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 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 of then ... and then some!

Dali Mihajlovic ALL IN PROPERTY MANAGEMENT LLC

7052 Live Oak 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 $639,110

Last Listing Agent Kendra Hoefs Realty One Group MVP

7717 Jacaranda Ln, Naples, FL 34114

/46
Est $531,101 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
- 13% Below List Price
- $393/SF
- 58 Days On Market
- Last Sold Price $610,000
- Mar 15, 2024
Last Listing Agent Jim Cunnyngham Premier Sotheby's Int'l Realty

/47
$949,900 Pending
- 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 2 baths with full showers , primary bath with custom mirrors. custom closet , plantation shutters mini a/c in garage, whole house water

Linda Covino Royal Shell Real Estate, Inc.

6844 Winding Cypress Dr, Naples, FL 34114
/39
$15,000 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 $764,103

Last Listing Agent Craig Jerabeck Premiere Plus Realty Company

7057 Live Oak Dr, Naples, FL 34114

/50
Est $1,076,226 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
- 8% Below List Price
- $471/SF
- 63 Days On Market
- Last Sold Price $1,175,000
- Aug 07, 2024
Last Listing Agent Gabriele H. Vretta John R Wood Properties

/47
$935,000
- 3 Beds
- 2 Baths
- 2,076 Sq Ft
6787 Pennyroyal Dr, Naples, FL 34114

Set 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 International Realty

6787 Pennyroyal 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
/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 $1,195,789

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

7597 Blackberry Dr, Naples, FL 34114

/44
Est $592,504 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
- 20% Below List Price
- $464/SF
- 104 Days On Market
- Last Sold Price $740,000
- Apr 23, 2024
Last Listing Agent Kimberly Hill Schulz Realty LLC

/50
$989,000 Pending
- 2 Beds
- 2 Baths
- 2,036 Sq Ft
7545 Geranium Way, Naples, FL 34114

Experience refined Naples living in this impeccably maintained, fully furnished residence in the prestigious gated community of Winding Cypress. Featuring two bedrooms plus a den, two baths, plus an extended additional den leading to the waterfront pool area, and an extended 2-car garage; this home has been thoughtfully designed and is move-in ready - blending comfort, elegance, and effortless

Nina Llorca Coldwell Banker Realty

7545 Geranium Way, 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
/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 $875,883

Last Listing Agent Kendra Hoefs Realty One Group MVP

7355 Mockingbird Ct, Naples, FL 34114

/43
Est $880,629 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
- 1% Below List Price
- $422/SF
- 3 Days On Market
- Last Sold Price $890,000
- Mar 28, 2025
Last Listing Agent Kimberly Springer Orchid Realty International

/47
$1,099,000
- 4 Beds
- 2 Baths
- 2,186 Sq Ft
7631 Winding Cypress Dr, Naples, FL 34114

This beautifully designed and impeccably maintained home offers the perfect blend of elegance and comfortable Naples living. Featuring the highly sought-after Summerwood floor plan with a spacious Great Room extension, the open layout creates an impressive, light-filled space perfect for entertaining guests or relaxing with family after a day exploring beautiful Naples, FL. The gourmet kitchen

Jeff Waldman Premiere Plus Realty Company

7631 Winding Cypress Dr, Naples, FL 34114
/46
$7,000 per month
- 2 Beds
- 2 Baths
- 1,542 Sq Ft
- House 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
/2
$530,000 Sold Jun 23, 2025

7702 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 $546,515

Last Listing Agent Comp Agent Marco Island Area Association Of Realtor

7702 Jacaranda Ln, Naples, FL 34114

/36
Est $581,701 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
- 14% Below List Price
- $434/SF
- 91 Days On Market
- Last Sold Price $675,000
- May 23, 2024
Last Listing Agent Frank Schultz Premiere Plus Realty Company

/53
$900,000 Open Sun 12PM - 3PM
- 3 Beds
- 2 Baths
- 2,186 Sq Ft
7679 Winding Cypress Dr, Naples, FL 34114

Welcome to this beautifully designed residence located within one of Naples' most desirable gated communities. The open-concept floor plan is enhanced by volume and tray ceilings, crown molding, plantation shutters throughout, and an extended driveway, adding both elegance and curb appeal. The spacious kitchen features granite countertops, a gas cooktop, wall oven, and ample cabinetry—making it

Joseph Bartos Premiere Plus Realty Company

7679 Winding Cypress Dr, Naples, FL 34114
/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 $600,804

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

7785 Jacaranda Ln, Naples, FL 34114

/42
Est $672,965 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
- 2% Below List Price
- $409/SF
- 20 Days On Market
- Last Sold Price $690,000
- Nov 08, 2024
Last Listing Agent Gabriele H. Vretta John R Wood Properties

/36
$875,000 Pending
- 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
/27
$675,000 Sold May 30, 2025

7742 Jacaranda Ln, Naples, FL 34114
- 2 Beds
- 2 Baths
- 1,554 Sq Ft
- Built 2019
Last Sold Summary
- 6% Below List Price
- $434/SF
- 47 Days On Market
Current Estimated Value $661,035

Last Listing Agent Bob Bailey R L Bailey Realty Inc.

7742 Jacaranda Ln, Naples, FL 34114

/49
Est $1,270,581 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
- 15% Below List Price
- $593/SF
- 56 Days On Market
- Last Sold Price $1,495,000
- Jan 21, 2025
Last Listing Agent Theresa Bocka William Raveis Real Estate

/48
$1,050,000
- 3 Beds
- 3 Baths
- 3,196 Sq Ft
6678 Pennyroyal Dr, Naples, FL 34114

This 2 Story Mystique Model, located in the desireable community of Winding Cypress, absolutely has to be seen to appreciate all that it offers. Instead of using AI to draft a lofty, fluffy, low information description of this home, we are just going to just list a few of the features and upgrades of this 3-year-new beauty! WHOLE HOUSE GENERATOR, HEATED SALTWATER POOL W/SPA & WATER FEATURE,

Paul Bocka William Raveis Real Estate

6678 Pennyroyal Dr, Naples, FL 34114
/42
$855,000 Sold Jul 11, 2025

6906 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 $898,679

Last Listing Agent Terence Trombetti Berkshire Hathaway FL Realty

6906 Winding Cypress Dr, Naples, FL 34114

/29
Est $724,713 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
- 5% Above List Price
- $369/SF
- 17 Days On Market
- Last Sold Price $692,500
- Jan 16, 2024
Last Listing Agent Jeri Neuhaus Capri Realty

/36
$1,098,000
- 3 Beds
- 2 Baths
- 2,166 Sq Ft
7457 Winding Cypress Dr, Naples, FL 34114

Rare opportunity in Winding Cypress this Marten Ray Model Home, Turnkey home fully upgraded, move-in ready home on a premium lot with unobstructed lake and protected preserve views. Experience complete privacy and a resort-style outdoor setting in one of Naples’ most desirable communities. Experience one of the most desirable homes in Winding Cypress, offering a rare combination of premium lot,

Beth Abraham Gulf Coast International Prop

7457 Winding Cypress Dr, Naples, FL 34114
/46
$975,000 Sold Sep 09, 2025

7788 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 $1,061,492

Last Listing Agent Justine Hine John R. Wood Properties

7788 Winding Cypress Dr, Naples, FL 34114

/50
Est $748,757 Not Listed For Sale

6792 Bromeliad Dr, Naples, FL 34114
- 2 Beds
- 2 Baths
- 1,774 Sq Ft
- Built 2021
6792 Bromeliad Dr, Naples, FL 34114

Last Sold Summary
- 5% Below List Price
- $443/SF
- 67 Days On Market
- Last Sold Price $785,000
- Dec 18, 2024
Last Listing Agent Nancy Bjork John R. Wood Properties

/38
$585,000
- 2 Beds
- 2 Baths
- 1,554 Sq Ft
7733 Jacaranda Ln, Naples, FL 34114

Discover effortless luxury in this lovely villa—your private oasis in a premier gated Naples community, Winding Cypress. This inviting 2-bedroom + den, 2-bath home delivers exceptional comfort and versatility with a bright, open layout designed for effortless living and entertaining. Step into the expansive Great Room with high ceilings, creating an open, airy vibe—perfect for gathering with

Jeff Waldman Premiere Plus Realty Company

7733 Jacaranda Ln, Naples, FL 34114
/50
$858,000 Sold Jan 16, 2026

6856 Winding Cypress Dr, Naples, FL 34114
- 3 Beds
- 2 Baths
- 2,076 Sq Ft
- Built 2021
Last Sold Summary
- 5% Below List Price
- $413/SF
- 81 Days On Market
Current Estimated Value $863,509

Last Listing Agent Brian Stolliker BERKSHIRE HATHAWAY HOMESERVICES FLORIDA REALTY

6856 Winding Cypress Dr, Naples, FL 34114

/49
Est $761,928 Not Listed For Sale

6852 Winding Cypress Dr, Naples, FL 34114
- 2 Beds
- 2 Baths
- 1,804 Sq Ft
- Built 2021
6852 Winding Cypress Dr, Naples, FL 34114

Last Sold Summary
- 2% Below List Price
- $430/SF
- 117 Days On Market
- Last Sold Price $775,000
- Mar 11, 2025
Last Listing Agent Ashley Prescott DomainRealty.com LLC

/48
$499,900
- 2 Beds
- 2 Baths
- 1,574 Sq Ft
7638 Jacaranda Ln, Naples, FL 34114

OPPORTUNITY AWAITS – LOWEST PRICE AVAILABLE! Welcome to the largest villa model in Winding Cypress, featuring a rare private front entrance and expanded foyer that sets the tone for this thoughtfully designed home. This spacious 2-bedrooms and massive den offers an open yet defined living concept with abundant natural light and seamless indoor-outdoor flow. Enjoy a long list of builder upgrades

Taylor Smith Premier Sotheby's Int'l Realty

7638 Jacaranda Ln, Naples, FL 34114

Showing Results 1 - 40, Page 1 of 18

Florida Collier County Naples Winding Cypress

Learn more about living in Winding Cypress

Home Trends in Winding Cypress, FL

On average, homes in Winding Cypress, Naples sell after 129 days on the market compared to the national average of 56 days. The median sale price for homes in Winding Cypress, Naples over the last 12 months is $835,000, down 2% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$835,000

Median Single Family Sale Price

$858,250

Median Townhouse Sale Price

$575,000

Median 2 Bedroom Sale Price

$537,000

Average Price Per Sq Ft

$417

Number of Homes for Sale

Last 12 months Home Sales

Months of Supply

1.90

Median List Price

$900,000

Median Change From 1st List Price

Median Home Sale Price YoY Change

-2%

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Winding Cypress Homes

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Housing Trends