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Winding Cypress Homes for Sale

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  • /36

    $639,900

    • 2 Beds
    • 2 Baths
    • 1,685 Sq Ft

    7248 Live Oak Dr, Naples, FL 34114

    Single Family home in Winding Cypress -Ready for the season!! 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

    Agent Photo

    Theresa Bocka

    William Raveis Real Estate

    (239) 456-3829

    7248 Live Oak Dr, Naples, FL 34114
  • /45

    $1,050,000

    • 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

    Agent Photo

    Theresa Bocka

    William Raveis Real Estate

    (239) 488-2755

    6825 Greenbriar Ct, Naples, FL 34114
  • /30

    $499,000 Open Sun 1PM - 4PM

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

    7658 Jacaranda Ln, Naples, FL 34114

    Experience luxury living in this beautifully appointed Serenity villa, greats you with LED walkway lighting along the entrance pathway. This property is nestled in one of Naples’ most desirable communities. This home features two spacious bedrooms, two elegant baths, and a flexible den—perfect for a home office, hobby room or additional guest area. The upgraded kitchen is equipped with stainless

    Agent Photo

    Theresa Bocka

    William Raveis Real Estate

    (239) 329-1331

    7658 Jacaranda Ln, Naples, FL 34114
  • /35

    $835,000 Open Sun 1PM - 4PM

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

    7211 Live Oak Dr, Naples, FL 34114

    Over 2200 Sq ft complete with your own POOL this is a great opportunity! Don't waitCheck out this impeccably maintained residence offers an exceptional living experience. The open floor plan features THREE spacious bedrooms, a versatile den or flex room, and two full bathroom. Elegant details include crown molding, tray ceilings, plantation shutters, Hunter Douglas blinds, and updated LVP

    Agent Photo

    Theresa Bocka

    William Raveis Real Estate

    (239) 266-8980

    7211 Live Oak Dr, Naples, FL 34114
  • /47

    $949,900

    • 2 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
  • /53

    $949,000 Open Sun 1PM - 4PM

    • 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
  • /38

    $949,900

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

    6787 Pennyroyal Dr, Naples, FL 34114

    The View !!!!!!!! built in 2022 Move in Ready ! Like new Contemporary style mystique model 3 bdrm den 2bath in Winding Cypress. Location Location with this breathtaking long lake view , last home on street on long landscaped corner affords plenty of privacy.Some of the Upgraded features consist of a widened paved recently sealed driveway comfortably fitting 2 cars side by side, zero clearance

    Linda Covino Royal Shell Real Estate, Inc.

    6787 Pennyroyal Dr, Naples, FL 34114
  • /50

    $943,000

    • 3 Beds
    • 3 Baths
    • 2,150 Sq Ft

    6698 Pennyroyal Dr, Naples, FL 34114

    Discover resort-style living in this rare three-bedroom plus den, three-bath natural gas home in the highly sought-after community of Winding Cypress. Designed for privacy and effortless indoor–outdoor living, it features an oversized fully custom pool with integrated seamless spa and a panoramic barless screen lanai, integrated home theater sound, all overlooking lush, tranquil landscaping. The

    Taylor Smith Premier Sotheby's Int'l Realty

    6698 Pennyroyal Dr, Naples, FL 34114
  • /36

    $899,000

    • 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
  • /50

    $875,000

    • 3 Beds
    • 3 Baths
    • 2,158 Sq Ft

    6754 Pennyroyal Dr, Naples, FL 34114

    This gorgeous Mystique floor plan features 3 bedrooms, a den, a rare 3 full bathrooms, heated pool, and a 2-car garage. Inside the home is loaded with upgrades, impact windows and doors, custom built-in cabinetry in the living & laundry room, crown molding, tray ceilings, recessed lighting, electric blinds, designer hardware and lighting, and abundant storage throughout. Embrace the Florida

    Kendra Hoefs Realty One Group MVP

    6754 Pennyroyal Dr, Naples, FL 34114
  • /37

    $825,000 Open Sun 1PM - 3PM

    • 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
  • /43

    $749,900 Pre-Foreclosure

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

    7057 Live Oak Dr, Naples, FL 34114

    Winding Cypress – PRICE REDUCED TO SELL- Rare opportunity to purchase in this community at this price point. Welcome to your Florida dream home in the sought-after gated community of Winding Cypress! This immaculate residence built in 2016, offers the perfect blend of modern luxury and relaxed coastal living. Featuring 2,230’sq under air, 4 bedrooms or use the 4TH bedroom as a den. Two full

    Craig Jerabeck Premiere Plus Realty Company

    7057 Live Oak Dr, Naples, FL 34114
  • /48

    $509,900

    • 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
  • /50

    $665,000

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

    7639 Jacaranda Ln, Naples, FL 34114

    Some of the most stunning sunset water views in all of Winding Cypress can be enjoyed right from your pool and spa overlooking the sparkling long lake, where a fully equipped natural gas outdoor kitchen with a vented hood creates the ultimate setting for entertaining or simply relaxing and taking in the view. Inside, the open floor plan feels light, bright, and inviting with updated flooring and

    Taylor Smith Premier Sotheby's Int'l Realty

    7639 Jacaranda Ln, Naples, FL 34114
  • /62

    $1,599,900

    • 4 Beds
    • 4 Baths
    • 3,350 Sq Ft

    7072 Live Oak Dr, Naples, FL 34114

    Welcome to this stunning Tangerly Oak model home, thoughtfully designed with space, style, and Florida living in mind. This expansive 4-bedroom residence with a generous loft offers a flexible floor plan ideal for both everyday living and hosting guests, all enhanced by beautiful designer upgrades throughout. Step outside to an exceptional outdoor living space featuring a large covered lanai,

    Reilly McGregor Harborview Realty Inc

    7072 Live Oak Dr, Naples, FL 34114
  • /33

    $630,000

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

    7121 Live Oak Dr, Naples, FL 34114

    Situated within the gated, amenity-rich community of Winding Cypress, this thoughtfully designed two-bedroom plus den, two-bath residence offers an exceptional blend of comfort, quality, and relaxed Florida living. The open floor plan is enhanced by wood flooring throughout the main living areas, along with crown molding, and a distinctive coffered ceiling in the living and dining area, creating

    Julie Blanton John R Wood Properties

    7121 Live Oak Dr, Naples, FL 34114
  • /39

    $550,000

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

    7176 Live Oak Dr, Naples, FL 34114

    Welcome to effortless, refined living in the highly desirable Winding Cypress community. Set on the largest homesite in the neighborhood, this impeccably upgraded 3-bedroom, 2-bath villa offers exceptional privacy, expansive outdoor space, and a true lock-and-leave lifestyle. Furnishings are negotiable, making this a flexible opportunity for both full-time and seasonal residents. Designed for

    David Burke John R Wood Properties

    7176 Live Oak Dr, Naples, FL 34114
  • /41

    $739,900

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

    7670 Jacaranda Ln, Naples, FL 34114

    Discover refined living with this beautifully appointed villa in Winding Cypress, where luxury and comfort meet in perfect balance. Designed for those who appreciate both elegance and ease, this home offers an unparalleled lifestyle inside and out.Arriving fully furnished and enhanced by the sellers’ two-seater Club Car golf cart, this property delivers a true move-in ready experience. Every

    Sean Smuk Coldwell Banker Realty

    7670 Jacaranda Ln, Naples, FL 34114
  • /16

    $529,000 Open Sun 1PM - 4PM

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

    7602 Jacaranda Ln, Naples, FL 34114

    Welcome to this meticulous light and bright two bedroom plus den, two bathroom property located in the preserve style, amenity rich community of Winding Cypress. Featuring stainless steel appliances, roomy kitchen, in residence laundry room with newer washer and dryer, screened in lanai, and open floor plan this home has multiple indoor and outdoor spaces for entertaining guests and hosting

    Taylor Miller Coldwell Banker Realty

    7602 Jacaranda Ln, Naples, FL 34114
  • /35

    $1,155,000 Open House 2/22

    • 3 Beds
    • 2 Baths
    • 2,166 Sq Ft

    7457 Winding Cypress Dr, Naples, FL 34114

    FINALLY, your own PRIVATE & SERENE OASIS, you’ll never get tired of. Not some angled or cropped view- just Actual Expansive Preserve Views! This exceptional setting provides a rare sense of seclusion and tranquility, creating an authentic Florida paradise lifestyle. This is a unique residence in Winding Cypress. This residence offers unmatched privacy and outdoor living, with exceptional standout

    Beth M Abraham Gulf Coast International Prop

    7457 Winding Cypress Dr, Naples, FL 34114
  • /44

    $610,000 Open Sun 1PM - 3PM

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

    7690 Jacaranda Ln, Naples, FL 34114

    Set against private garden views with tranquil eastern exposure, this beautifully appointed villa in Winding Cypress offers a peaceful retreat and effortless indoor-outdoor living. Featuring two bedrooms plus a den, two baths, and a two-car garage, this thoughtfully designed residence combines quiet luxury with meticulous updates in one of Naples' most dynamic lifestyle communities. The screened

    Michelle Thomas Premier Sotheby's International Realty

    7690 Jacaranda Ln, Naples, FL 34114
  • /44

    $699,900

    • 2 Beds
    • 2 Baths
    • 1,659 Sq Ft

    7255 Live Oak Dr, Naples, FL 34114

    This home has just been freshly painted inside and out. professionally painted kitchen and bath cabinets, nice private south west waterview , screened lanai able to enlarge or even add a pool. Previous owner had a great workshop in garage with 8 overhead lights, charging station for a Tesla , framed peg boards for hanging tools , custom storage cabinets and a pull down staircase for added

    Linda Covino Royal Shell Real Estate, Inc.

    7255 Live Oak Dr, Naples, FL 34114

Why Live in Winding Cypress

Winding Cypress in Naples is a gated community featuring around 800 homes and villas, predominantly in Coastal Contemporary and Mediterranean Revival styles. Residents enjoy professionally landscaped properties with trimmed lawns and flower-filled gardens. The neighborhood boasts a crime score significantly lower than the national average, providing a safer living environment. Amenities include a clubhouse, pool, dog park, community garden, and courts for tennis, bocce, and pickleball. The community is adjacent to Picayune Strand Forest, offering a boardwalk and picnic area. Golf enthusiasts will find several courses within 4 miles, such as Eagle Creek Golf and Country Club. Boating facilities are available at Tarpon Club Marina and Naples Cruise Club, less than 10 miles away. The Shady Palm Café, located in the clubhouse, is a popular spot for residents, serving food and drinks and hosting neighborhood events. Shopping options are conveniently located 2 miles away at Tamiami Crossing and Shops at Eagle Creek, featuring stores like Walmart, Aldi, and Publix. Highway 41 provides access to Naples, 10 miles away, and Marco Island, 11 miles to the south, with public transit available via Collier Area Transit. The nearest healthcare facility is Physicians Regional on Collier Boulevard, 3 miles away. Schools in the Collier County School District, including Lely Elementary, Manatee Middle, and Lely High, have high ratings. Florida SouthWestern State College - Collier Campus is also nearby, just 4 miles from the community.

Frequently Asked Questions

Is Winding Cypress a good place to live?
Winding Cypress is a good place to live. Winding Cypress is considered very car-dependent and somewhat bikeable. It has a median age of 69. The average household income is $115,017 which is above the national average. College graduates make up 43.4% of residents. A majority of residents in Winding Cypress are home owners, with 12.5% of residents renting and 87.5% of residents owning their home. A local real estate agent serving Winding Cypress can help you decide if this neighborhood is the right one for you. Learn more on our Winding Cypress neighborhood guide.
Is Winding Cypress, FL a safe neighborhood?
Winding Cypress, FL is safer than the average neighborhood in the United States. It received a crime score of 3 out of 10.
How much do you need to make to afford a house in Winding Cypress?
The median home price in Winding Cypress is $899,000. If you put a 20% down payment of $179,800 and had a 30-year fixed mortgage with an interest rate of 6.11%, your estimated principal and interest payment would be $4,360 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $187K a year to afford the median home price in Winding Cypress. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Winding Cypress is $115K.
What are the best public schools in Winding Cypress?
The best public schools that serve Winding Cypress are:
What are the most popular zip codes in Winding Cypress, Naples, FL?
The most popular zip codes in Winding Cypress, Naples, FL include 34114, 34110, 34102, 34113 and 34103.
What are the most popular neighborhoods near Winding Cypress, Naples, FL?
The most popular neighborhoods near Winding Cypress, Naples, FL are Belle Meade, Naples Reserve, Reflection Lakes, South Naples and Fiddler's Creek.
Are home prices dropping in Winding Cypress?
Yes, home prices in Winding Cypress are down 13% in the last 12 months.

Home Trends in Winding Cypress, FL

Housing Trends

Median Sale Price
$850,000
Median Single Family Sale Price
$875,000
Median Townhouse Sale Price
$575,000
Median 2 Bedroom Sale Price
$537,000
Average Price Per Sq Ft
$420
Number of Homes for Sale
21
Last 12 months Home Sales
87
Months of Supply
2.90
Median List Price
$899,000
Median Change From 1st List Price
9%
Median Home Sale Price YoY Change
0%
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