20

Winding Cypress Homes for Sale

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  • /35

    $1,645,000

    • 4 Beds
    • 4 Baths
    • 3,656 Sq Ft

    7247 Clamshell Ln, Naples, FL 34114

    Rarely available, highly sought after 4-Bedroom home in prestigious Winding Cypress, with uninterrupted water and preserve views (no homes) both front and back, heavily upgraded and designed to mirror the model home. Over 3,600 sq ft of luxurious living in a small enclave, just a couple of minutes’ walk from the amenity center, yet removed from community density — delivering luxury, privacy,

    Sheila Kumar Real Broker, LLC

    7247 Clamshell Ln, Naples, FL 34114
  • /50

    $989,000 Open Sun 1PM - 4PM

    • 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
  • /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
  • /50

    $850,000

    • 3 Beds
    • 2 Baths
    • 2,188 Sq Ft

    7460 Blackberry Dr, Naples, FL 34114

    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 with gas stove, brand new LG

    Angelica Andrews Premier Sotheby's Int'l Realty

    7460 Blackberry Dr, Naples, FL 34114
  • /38

    $599,999

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

    7733 Jacaranda Ln, Naples, FL 34114

    Discover effortless luxury in this impeccably maintained villa—your private oasis in Naples' premier gated community, Winding Cypress. This inviting 2-bedroom + den, 2-bath home delivers exceptional comfort and versatility. Both bedrooms feature generous walk-in closets. The guest suite offers true privacy with a hallway pocket door that creates a secluded en-suite retreat. Bathrooms showcase

    Jeff Waldman Premiere Plus Realty Company

    7733 Jacaranda Ln, Naples, FL 34114
  • /33

    $630,000

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

    7121 Live Oak Dr, Naples, FL 34114

    Nestled within the gated, amenity-rich community of Winding Cypress, this thoughtfully designed turnkey furnished 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

    Julie Blanton John R Wood Properties

    7121 Live Oak Dr, Naples, FL 34114
  • /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 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
  • /50

    $649,000

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

    7639 Jacaranda Ln, Naples, FL 34114

    Sunset water views stretch across a sparkling long lake from your private pool and spa, creating a breathtaking backdrop for everyday living and entertaining from the fully equipped natural gas outdoor kitchen. This beautifully maintained home stands out with major recent upgrades including a brand new AC system (2026), new washer and dryer, new hot water heater, and new carpet, offering peace of

    Taylor Smith Premier Sotheby's Int'l Realty

    7639 Jacaranda Ln, Naples, FL 34114
  • /50

    $845,000

    • 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
  • /49

    $639,900 Open Sun 1PM - 2:30PM

    • 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, addition dual media cat5/rg6 charging station for a Tesla , framed peg boards for hanging tools , custom storage cabinets and a pull

    Linda Covino Royal Shell Real Estate, Inc.

    7255 Live Oak Dr, Naples, FL 34114
  • /53

    $949,000

    • 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

    $1,499,900

    • 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
  • /45

    $1,050,000 Open Sun 1PM - 4PM

    • 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
  • /36

    $1,098,000

    • 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. This is not your typical rear lanai view, It is an Actual Expansive Preserve View! 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

    Beth M Abraham Gulf Coast International Prop

    7457 Winding Cypress Dr, Naples, FL 34114
  • /36

    $634,999

    • 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
  • /41

    $698,500

    • 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
  • /36

    $875,000 Open Sun 1PM - 4PM

    • 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
  • /37

    $825,000

    • 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
  • /38

    $919,000

    • 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
  • /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

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 with minimal transit options. 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 $900,000. If you put a 20% down payment of $180,000 and had a 30-year fixed mortgage with an interest rate of 6.11%, your estimated principal and interest payment would be $4,370 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, 34102, 34113, 34103 and 34112.
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 12% in the last 12 months.

Home Trends in Winding Cypress, FL

Housing Trends

Median Sale Price
$858,000
Median Single Family Sale Price
$858,500
Median Townhouse Sale Price
$602,500
Median 2 Bedroom Sale Price
$556,000
Average Price Per Sq Ft
$417
Number of Homes for Sale
20
Last 12 months Home Sales
93
Months of Supply
2.60
Median List Price
$900,000
Median Change From 1st List Price
9%
Median Home Sale Price YoY Change
1%
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