14

Studio to 3 Bedroom Homes for Sale in Winding Cypress

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  • /41

    $534,500

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

    7658 Jacaranda Ln, Naples, FL 34114

    This beautiful Winding Cypress Serenity Villa home offers 1,554 sq. ft. of comfort with 2 bedroom plus den, 2 bathrooms, screened lanai, and a 2-car garage. It features multiple quality upgrades including stainless appliances with both gas and electric connectivity for the stove, 22" porcelain tile on the diagonal throughout, plantation shutters, Quartz countertops in kitchen and bathrooms, den

    Bob Lashenka Downing Frye Realty Inc.

    7658 Jacaranda Ln, Naples, FL 34114
  • /49

    $925,000

    • 3 Beds
    • 2 Baths
    • 2,094 Sq Ft

    6699 Pennyroyal Dr, Naples, FL 34114

    Perfection is the only way to describe this home! It shows like a model as it has been rarely lived in since built barely three years ago. Welcome to the desirable Pulte/DiVosta Mystique Model located in the popular amenity rich community of Winding Cypress. This waterfront property sits on a dead-end cul-de-sac and is loaded with owner and builder upgrades. It's impeccably decorated and

    Theresa Bocka William Raveis Real Estate

    6699 Pennyroyal Dr, Naples, FL 34114
  • /40

    $959,900

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

    6787 Pennyroyal Dr, Naples, FL 34114

    Move in Ready 3 year old 3 bdrm den 2bath Mystic model at Winding Cypress. Here are some of the reasons we are we different from the rest . widened paved driveway comfortablly fitting 2 cars side by side, corner lot for privacy, beautiful long lake view on WC largest lakes, 4ft extended garage for larger vehicles plus overhead storage with Mini a/c split in garage. whole house generator, impact

    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
  • /48

    $600,000

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

    7167 Live Oak Dr, Naples, FL 34114

    Rare villa opportunity in Winding Cypress! This turnkey, fully furnished villa sits on an extra-large, ultra-private lot with exceptional spacing between neighbors, creating a peaceful and open feel that is hard to find. The backyard is a retreat, featuring a saltwater private pool framed by mature cypress trees, colorful landscaping and wide natural preserve views. Inside, the home offers

    Taylor Smith Premier Sotheby's Int'l Realty

    7167 Live Oak Dr, Naples, FL 34114
  • /43

    $819,000 Pre-Foreclosure

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

    7057 Live Oak Dr, Naples, FL 34114

    Winding Cypress – Resort-Style Living in Naples - Priced to sell!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, 3 bedrooms plus a den, 2 full baths, and an open-concept floor plan, this home is designed for

    Craig Jerabeck Premiere Plus Realty Company

    7057 Live Oak Dr, Naples, FL 34114
  • /37

    $639,900 Open House 1/11

    • 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

    Theresa Bocka William Raveis Real Estate

    7248 Live Oak Dr, Naples, FL 34114
  • /36

    $925,000

    • 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
  • /48

    $1,160,000 Open Sun 1PM - 4PM

    • 3 Beds
    • 3 Baths
    • 2,496 Sq Ft

    7520 Blackberry Dr, Naples, FL 34114

    Introducing a luxury estate with landscaped privacy corner lot home in Winding Cypress with pool and spa. Step into elegance with this stunning Pinnacle model estate home, set in the prestigious, gated community of Winding Cypress. This home stands out with its soaring raised tray ceilings, rare privacy and spacious yard, impact glass for peace of mind, and an expansive open layout filled with

    Taylor Smith Premier Sotheby's Int'l Realty

    7520 Blackberry Dr, Naples, FL 34114
  • /41

    $749,900

    • 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

    • 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

    $1,188,000 Open Sun 1PM - 4PM

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

    7457 Winding Cypress Dr, Naples, FL 34114

    The Martin Ray Floor Plan is PRIVACY-PRIVACY-a REAL Piece of Florida Paradise. An exceptional model styled home on a premium lot withrare, unobstructed views of the lake and the Preserve. This residence offers unmatched privacy and outdoor living, with twostandout features: an expansive screened lanai with custom accent lighting, saltwater, heatedpool, plus an outdoor dry bar with

    Beth M Abraham Gulf Coast International Prop

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

    $639,000 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
  • /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

Home Trends in Winding Cypress, FL

Housing Trends

Median Sale Price
$850,000
Median Single Family Sale Price
$855,000
Median Townhouse Sale Price
$707,000
Median 2 Bedroom Sale Price
$534,500
Average Price Per Sq Ft
$425
Number of Homes for Sale
16
Last 12 months Home Sales
81
Months of Supply
2.40
Median List Price
$900,000
Median Change From 1st List Price
9%
Median Home Sale Price YoY Change
0%
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