Winding Cypress Naples Homes for Sale

The Crown Jewel of Winding Cypress! This RARELY available Stonewater floor plan with a TRUE 3-CAR GARAGE is a standout, offering an exceptional blend of luxury, privacy, and breathtaking views. A custom pool with picture-screen enclosure takes full advantage of the highly desirable SOUTHWEST EXPOSURE, showcasing long lake views and spectacular sunsets. Designed for seamless indoor-outdoor living, this home features a custom outdoor kitchen and a convenient half-pool bath upgrade. Inside, every detail has been thoughtfully enhanced with designer upgrades, including 18” x 36” tile throughout and a custom wall unit with a heat-generating fireplace. The split floor plan maximizes privacy, with all three bedrooms in separate areas of the home. Guest areas can be closed off with pocket doors, creating a private suite-like feel with access to their own bathroom. For peace of mind, this home features a whole-house generator, IMPACT GLASS throughout, and push-button hurricane shutters make storm protection effortless for the lanai. Located in Winding Cypress, a natural gas, low-fee, resort-style community, this home sits on an oversized, private lot on a cul-de-sac street. Perfectly situated between Marco Island and downtown Naples, residents enjoy easy access to world-class dining, shopping, and beaches—all within a golf-cart-friendly community. World-class amenities include a heated resort-style pool with a unique walk-in entrance—allowing effortless access—plus lap lanes, a hot tub, poolside cabanas, and a gas fire pit area. The Shady Palm Café, a covered outdoor restaurant, bar, and grill, provides the perfect place to unwind—whether dining al fresco or gathering for a drink. The expansive clubhouse features a large fitness center, movement studio, library, card room, and event room—all managed by an on-site Activities Director and full time property management. Outdoor enthusiasts will love exploring this 1,100-acre community, where over 800 acres of preserve are woven with miles of scenic sidewalks and a picturesque boardwalk leading to a bird-wading overlook. Enjoy a game of pickleball, bocce, or tennis. Additional amenities include separate dog parks for small and large dogs and a members-only community garden for those who enjoy growing their own vegetables. Don’t miss this rare opportunity to own a home that blends luxury, privacy, and resort-style living—schedule your private tour today!

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:

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This property is courtesy of William Raveis Real Estate.

*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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