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Naples Florida Winding Cypress Homes for Sale

Naples Florida Real Estate

Winding Cypress Naples Real Estate

Homes For Sale19$510K - $1.6M
Sold ( Past 6 Months )26$500K - $1.6M
Last updated at 6:26pm 02/05/2026

$639,900
Decrease*
$10K

MLS# 225072028

7248 Live Oak Dr, Naples, FL 34114

Homes - 1,685 ft² / 2,034 ft² - 2 Car Garage

2+Den / 2 Baths

Built 2016

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 floors are throughout much of the space. There's a den/flex room with french doors that can be used as an additional bedroom when needed or office, hobby or quiet sitting room. Additional guest bedroom and bathroom with combined tub and shower and granite topped vanity offers privacy for your family and guests. The laundry room features a spacious storage area with shelving for your all your supplies. There are storage racks in the two car garage to house your coolers for the beach. Be sure to take time to relax and enjoy your morning beverage and the beautiful sunsets on the screened lanai that overlooks the OVERSIZED lot with mature landscaping complete with an outdoor kitchen with grill, sink, and fridge for your convenience. Winding Cypress is a sought after, gated community and is appreciated for its active, social lifestyle and world class amenities. It’s nestled within 800 acres of natural preserve and 80 acres of serene lakes teeming with migratory wildlife. Head over to the clubhouse with state-of-the-art fitness center, locker rooms with showers, movement room for classes, internet café, event room, catering kitchen, resort-style pool with spa and cabanas, restaurant with bar, firepit, pickleball, tennis and bocce courts. Take the pups to play in the dog park. Walk or ride your bike on the many paths including the peaceful preserve boardwalk. If gardening is your passion, there is a community garden to grow your favorite vegetables. HOA management and friendly staff are onsite to assist and coordinate regular events for all to enjoy. Minutes from beaches, golfing, fishing, boating, shopping, and cultural activities. It's time to enjoy the Florida lifestyle!

PROPERTY DETAILS:

Community Name: Winding Cypress
Community Type: Gated
Amenities: Bike And Jog Path, Bocce Court, Cabana, Clubhouse, Pool, Community Room, Spa/Hot Tub, Dog Park, Fitness Center, Internet Access, Library, Pickleball, Restaurant, Sidewalk, Streetlight, Tennis Court(s)
Building Design: Ranch, Single Family
Building Desc: 1 Story/Ranch
Living Area: 1,685 ft²
Total Area: 2,034 ft²
View: Landscaped Area, Privacy Wall
Unit Floor: 1
Total Floors: 1
Parking: Driveway Paved, Attached
Garage Spaces: 2
Construction: Concrete Block, Stucco
Exterior Features: Screened Lanai/Porch, Outdoor Kitchen
Roof: Tile
Private Pool: Community
Private Spa: Community
Floor Description: Carpet, Tile
Interior Features: Built-In Cabinets, French Doors, Laundry Tub, Pantry, Smoke Detectors, Walk-In Closet(s), Window Coverings
Pets: Limits
Units in Building: 1
On Site Since: 10/01/2025
Irrigation: Reclaimed
Water: Central
Equipment: Auto Garage Door, Dishwasher, Disposal, Dryer, Grill - Gas, Microwave, Range, Refrigerator/Freezer, Self Cleaning Oven, Smoke Detector, Washer
Floor Plan Type: Split Bedrooms
Furnished Desc: Unfurnished
Maintenance: Lawn/Land Maintenance, Manager, Rec Facilities, Repairs, Reserve, Security, Street Lights, Street Maintenance
Min Days of Lease: 30
Leases Per Year: 3
Rear Exposure: SE
Restrictions: Architectural, Deeded, No Commercial, No RV
Acres: 0.16
Lot Desc: Oversize
Lot Left: 135
Lot Right: 135
Lot Back: 50
Lot Frontage: 50
HOA Fees: $1,543 Quarterly
Transfer Fee: $1,050
Total Annual Recurring Fees: $6,652
Taxes: $4,978
Tax Year: 2025
Golf Type: No Golf Available

THIS PROPERTY IS COURTESY OF:

William Raveis Real Estate

IMAGES:

LOCATION:

AREA SPECIALIST:


Helen Mikhailova
2025 Five Star Real Estate Agent

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."

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 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.

The data relating to real estate for sale/lease on this web site come in part from a cooperative data exchange program of the multiple listing service (MLS) in which this real estate firm (Broker) participates. The properties displayed may not be all of the properties in the MLS's database, or all of the properties listed with Brokers participating in the cooperative data exchange program. Properties listed by Brokers other than this Broker are marked with either the listing Broker's logo or name or the MLS name or a logo provided by the MLS. Detailed information about such properties includes the name of the listing Brokers. Information provided is thought to be reliable but is not guaranteed to be accurate; you are advised to verify facts that are important to you. No warranties, expressed or implied, are provided for the data herein, or for their use or interpretation by the user. The Florida Association of Realtors and its cooperating MLSs do not create, control or review the property data displayed herein and take no responsibility for the content of such records. Federal law prohibits discrimination on the basis of race, color, religion, sex, handicap, familial status or national origin in the sale, rental or financing of housing.

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