Winding Cypress Naples Homes for Sale

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 relaxed everyday living and easy entertaining, the open floor plan feels light, inviting, and polished without being formal. Thoughtful designer touches throughout create a warm, comfortable atmosphere that flows naturally from indoors to outdoors. The extended screened lanai becomes an everyday retreat, ideal for morning coffee, sunset unwinding, or hosting friends, while the outdoor summer kitchen makes casual gatherings effortless. Peace of mind is a defining feature of this home, with over $100,000 in safety and security upgrades already in place. A whole-house backup generator, advanced security system, hurricane protection, and smart access features allow you to travel or entertain with confidence, knowing everything is covered. Living in Winding Cypress means enjoying a resort-style lifestyle every day. Residents have access to a beautifully appointed clubhouse with on-site dining, resort and lap pools, a jacuzzi, fitness center, tennis, pickleball, bocce courts, and a dog park. The community is surrounded by natural preserves and lakes, creating a serene setting while remaining minutes from shopping, dining, and daily conveniences. This is a rare opportunity to own a premier villa in one of Southeast Naples’ most sought-after gated communities. Priced competitively and offering flexibility on furnishings, this home delivers comfort, security, and lifestyle in one exceptional package.

Oleg Mikhailov

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

Luxury of Naples Group at Premiere Plus Realty

Phone: (239) 280-1237

Website: https://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.

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We need to know what you are actually looking for. Please be as detailed as possible, ie: areas of interest, property type, property size via sq. ft., bedrooms, bathrooms, price range, amenities, view, and any must haves that are key factor that would make the homes we pre-select the perfect choice for you. *

This property is courtesy of John R Wood Properties.

*Just Listed: new properties that came on the market within the last 30 days.
*Decrease/Increase: listing values that are being recorded within the last 30 days.
*Foreclosures/Short Sale: Please note, all properties are subject to bank approval. Buyers must be pre-approved or show proof of funds before submitting an offer.

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