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Naples Florida Winding Cypress Homes for Sale

Naples Florida Real Estate

Winding Cypress Naples Real Estate

Homes For Sale18$529K - $1.6M
Sold ( Past 6 Months )26$475K - $1.4M
Last updated at 2:39am 12/08/2025

$1,188,000
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MLS# 225067825

7457 Winding Cypress Dr, Naples, FL 34114

Homes - 2,166 ft² / 2,470 ft² - 2 Car Garage

3+Den / 2 Baths / Pool

Built 2017

The Martin Ray Floor Plan is PRIVACY-PRIVACY-PRIVACY. An exceptional model styled home on a premium lot with rare, unobstructed views of the lake and the Preserve. This residence offers unmatched privacy and outdoor living, with two standout features: an expansive screened lanai with custom accent lighting, saltwater, heated pool, plus an outdoor dry bar with refrigerator and cabinetry—all designed to create your own private resort overlooking nature. Inside, every detail reflects model-quality craftsmanship. The home showcases a chef’s kitchen with Alexa-linked gas 5 Burner stove/oven, upgraded cabinetry with pull-out drawers, upgraded appliances. A butler’s wine bar with under cabinet lighting cabinetry, upgraded wine dual temp refrigerator, pantry shelving, adds elegance and convenience. Additional upgrades include custom wall features, garage hallway bench with storage unit, and abundant built-in closet storage. The primary suite is highlighted by a custom walk-in closet with cabinetry, blending function and style. Custom front and lanai accent lighting enhance both curb appeal and evening ambiance. Winding Cypress is one of Naples’ premier resort-style communities, surrounded by 800 acres of protected preserve and 80 acres of lakes. Residents enjoy a zero-entry resort pool and spa, the Shady Palm Café with full-service bar and grill, a state-of-the-art fitness center, pickleball and tennis courts, dog park, community garden, walking/biking trails, and a full social calendar curated by the on-site activities’ director. All of this is just minutes from downtown Naples, Marco Island, beaches, world-class golf, shopping, and dining—yet with the peace and seclusion of a preserve setting. This is more than a home; it is a rare lifestyle opportunity combining privacy, luxury, and nature in perfect harmony.

PROPERTY DETAILS:

Community Name: Winding Cypress
Community Type: Gated, Tennis
Amenities: Beauty Salon, Bike And Jog Path, Clubhouse, Pool, Spa/Hot Tub, Concierge, Dog Park, Fitness Center, Hobby Room, Internet Access, Library, Pickleball, Private Membership, Restaurant, Sidewalk, Streetlight, Tennis Court(s)
Building Design: Ranch, Single Family
Building Desc: 1 Story/Ranch
Living Area: 2,166 ft²
Total Area: 2,470 ft²
View: Lake, Landscaped Area, Preserve
Total Floors: 1
Parking: Driveway Paved, Attached
Garage Spaces: 2
Construction: Concrete Block, Poured Concrete, Stucco
Exterior Features: Screened Lanai/Porch
Roof: Tile
Private Pool: Community, Salt Water
Private Spa: Community
Floor Description: Tile
Interior Features: Built-In Cabinets, Closet Cabinets, Custom Mirrors, Foyer, French Doors, Pantry, Pull Down Stairs, Smoke Detectors, Vaulted Ceiling(s), Walk-In Closet(s), Wet Bar
Pets: With Approval
On Site Since: 10/10/2025
Irrigation: Assessment Paid
Water: Assessment Paid
Equipment: Auto Garage Door, Cooktop - Gas, Dishwasher, Disposal, Dryer, Microwave, Refrigerator/Freezer, Self Cleaning Oven, Smoke Detector, Wall Oven, Washer, Wine Cooler
Floor Plan Type: Great Room, Split Bedrooms
Furnished Desc: Negotiable
Maintenance: Manager, Street Lights, Street Maintenance
Min Days of Lease: 3
Leases Per Year: 30
Rear Exposure: E
Elementary School: Manatee Elementary School
Middle School: Manatee Middle School
High School: Lely High School
Restrictions: Architectural
Acres: 0.19
Lot Desc: Zero Lot Line
Lot Left: 135
Lot Right: 135
Lot Back: 34
Lot Frontage: 56
Master HOA Fee: $1,558 Quarterly
Transfer Fee: $1,050
Total Annual Recurring Fees: $6,682
Taxes: $4,601
Tax Year: 2024
Golf Type: No Golf Available

THIS PROPERTY IS COURTESY OF:

Gulf Coast International Prop

IMAGES:

LOCATION:

AREA SPECIALIST:


Oleg Mikhailov
Oleg Mikhailov

Area Specialist, REALTOR®
Broker Associate
GRI - Graduate Realtor Institute

Luxury of Naples Group at Premiere Plus Realty

Phone: (239) 280-1237

Websitehttps://www.realtyofnaples.com

Bio

Oleg Mikhailov has been a Naples resident since 1999 and is deeply familiar with the neighborhoods of Naples, Bonita Springs, and Marco Island. His extensive local knowledge allows him to expertly assist you in finding the perfect home for your family’s unique needs. With Oleg as your Real Estate Broker, you can trust that his dedication and expertise will make your experience seamless and enjoyable.

In addition to his real estate career, Oleg is an experienced engineer. This technical expertise enhances his ability to evaluate properties, providing valuable insights into a home’s structure and potential. His engineering background, combined with his work as a financial consultant for global real estate projects and business development programs, equips him with a rare skill set that ensures you’re getting the best advice and support in every transaction.

Outside of his professional career, Oleg was part of a professional auto racing team and has earned several international sports awards. His racing experience has honed his attention to detail and focus, qualities that translate directly to his work in real estate. His stress-free approach, paired with his guiding principle—a happy client is the most important thing—ensures that you’ll have a positive and rewarding experience.

Whether you’re buying or selling, Oleg Mikhailov is committed to making your real estate journey smooth, successful, and satisfying.

CONTACT / REQUEST APPOINTMENT:


In order to better assist our clients, we need to know as much as possible relating to: you, your situation, your needs, what you are looking for, and how we can best assist you. Please be as detailed as possible, for if you are vague, we may miss something - thus, not providing the best service possible. Your satisfaction is our top priority. By providing your phone number, you consent to receive communications, including but not limited to text messages and phone calls, from Luxury Of Naples Group regarding your inquiries, appointments, updates, or other services. Message and data rates may apply. You can opt-out at any time by replying STOP to any text message or contacting us.
Thank you! We look forward to the opportunity to earn your trust and your business.








Broker Reciprocity LogoThis property is courtesy of Gulf Coast International Prop.

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