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Naples Florida Winding Cypress Homes Under Contract

Naples Florida Real Estate

Winding Cypress Naples Real Estate

Homes For Sale16$500K - $1.8M
Sold ( Past 6 Months )31$499K - $1.8M
Last updated at 8:53am 05/08/2026

Pending with Contingencies
$599,000

MLS# 226006762

7121 Live Oak Dr, Naples, FL 34114

Homes - 1,554 ft² / 1,898 ft² - 2 Car Garage

2+Den / 2 Baths / Spa

Built 2016

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 dining area, creating a refined yet inviting atmosphere. The kitchen is both elegant and functional, featuring 42" white cabinetry, granite countertops, tile backsplash, undercabinet lighting, and stainless-steel appliances—ideal for everyday living and entertaining alike. A flexible den with French doors provides the option for a private home office, media room, or additional guest space. Seamless indoor-outdoor living is achieved through the expansive custom lanai, designed for entertaining with an outdoor kitchen complete with gas grill, refrigerator, and sink, an above-ground HotSprings hot tub with beautiful outdoor furnishings including a dining table for six, over-sized parasol umbrellas that provide shade, and picture-frame lanai screens that showcase peaceful preserve surroundings. Additional highlights include a whole-house gas generator, two-car garage, and plantation shutters. Winding Cypress is a natural gas community thoughtfully designed around preserved natural beauty and an active, social lifestyle. At its heart is an impressive clubhouse with a heated resort-style pool and spa, poolside dining at The Shady Palm, state-of-the-art fitness center, library, and community gathering rooms. Other amenities include pickleball and tennis courts, bocce courts, dog parks, a community garden, and scenic walking and nature trails. Known for its welcoming atmosphere and beautifully maintained grounds, Winding Cypress offers a true sense of community while remaining conveniently close to everything Naples has to offer. A six-passenger well-maintained golf cart is included for effortless access throughout the neighborhood.

PROPERTY DETAILS:

Community Name: Winding Cypress
Community Type: Gated
Amenities: Bike And Jog Path, Bocce Court, Pool, Community Room, Spa/Hot Tub, Dog Park, Fitness Center, Library, Pickleball, Restaurant, Sidewalk, Streetlight, Tennis Court(s), Underground Utility
Building Design: Ranch, Single Family
Building Desc: 1 Story/Ranch
Living Area: 1,554 ft²
Total Area: 1,898 ft²
View: Landscaped Area, Preserve
Unit Floor: 1
Total Floors: 1
Parking: Driveway Paved, Attached
Garage Spaces: 2
Construction: Concrete Block, Stucco
Exterior Features: Screened Lanai/Porch, Built In Grill, Outdoor Kitchen
Roof: Tile
Private Pool: Community
Private Spa: Community, Above Ground
Floor Description: Carpet, Tile, Wood
Interior Features: Closet Cabinets, Coffered Ceiling(s), French Doors, Laundry Tub, Pantry, Tray Ceiling(s), Walk-In Closet(s), Window Coverings
Pets: Limits
Units in Building: 2
On Site Since: 02/11/2026
Irrigation: Central
Water: Central
Equipment: Auto Garage Door, Dishwasher, Disposal, Dryer, Generator, Grill - Gas, Microwave, Range, Refrigerator/Icemaker, Washer
Floor Plan Type: Split Bedrooms
Furnished Desc: Turnkey
Maintenance: Lawn/Land Maintenance, Legal/Accounting, Manager, Rec Facilities, Reserve, Security, Street Lights, Street Maintenance
Min Days of Lease: 30
Leases Per Year: 3
Rear Exposure: NW
Restrictions: Architectural, Deeded, No Commercial, No RV
Acres: 0.15
Lot Desc: Regular
Lot Left: 135
Lot Right: 135
Lot Back: 60
Lot Frontage: 347
Master HOA Fee: $1,455 Quarterly
Transfer Fee: $1,050
Total Annual Recurring Fees: $6,220
Taxes: $7,561
Tax Year: 2025
Total One Time Fees: $1,300

THIS PROPERTY IS COURTESY OF:

John R Wood Properties

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AREA SPECIALIST:


Helen Mikhailova
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Certified Luxury Home Marketing Specialist
Helen Mikhailova

AREA Specialist, REALTOR®
Broker Associate
GRI - Graduate Realtor Institute
CLHMS - Certified Luxury Home Marketing Specialist
Million Dollar GUILD
SRS - Seller Representative Specialist
Residential Interior Designer Certification
Five Star Real Estate Agent 2020-2025 Award

Luxury of Naples Group at Premiere Plus Realty

Phone: (239) 217-6283

Websitehttps://www.realtyofnaples.com

Bio

Helen Mikhailova is a highly accomplished Real Estate Broker with a Graduate Real Estate Institute (GRI) designation, a Luxury Home Marketing Specialist certification, and a newly earned Residential Interior Designer Certification. Fluent in English, Ukrainian, and Russian, Helen's multilingual abilities, business acumen, and global travel experience make her an exceptional choice for clients from diverse backgrounds.

Since 2005, Helen has called Naples home and has been helping clients navigate the real estate market since 2011. Her 14+ years of experience in real estate have equipped her with the expertise and insight to guide clients through every stage of the buying or selling process.

With a Master’s Degree in Mathematics, Helen brings a unique analytical perspective to real estate, ensuring clients receive informed, data-driven guidance. Her dedication to excellence has earned her recognition as a 5-star Agent from 2020 to 2023, and again in 2025, a testament to her commitment to client satisfaction and outstanding results.

"I love working with people and seeing their joy when a deal closes. Real estate allows me to connect with individuals, build meaningful relationships, and help them achieve their goals. Every day is different, exciting, and rewarding—it’s why I love what I do."

Helen’s deep knowledge of Naples and its unique communities comes from nearly two decades of living in the area. Her extensive travels enable her to confidently compare Naples to some of the world’s finest destinations. "Naples is one of the most sophisticated, attractive, and relaxing towns I’ve ever experienced. I am proud to call it my home and to help others do the same."

Helen specializes in creating stress-free, enjoyable real estate experiences for her clients. Whether working with locals or newcomers to sunny Florida, she excels at making the process seamless and satisfying.

"Through clear communication and a personalized approach, I help my clients turn their vision of living in beautiful, sunny Naples into reality."

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