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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.
Property Details
Price: $550,000
Sq Ft: 1,554
($354 per sqft)
Bedrooms: 3
Bathrooms: 2
City: Naples
County: Collier
Type: Single Family
Development: Winding Cypress
Virtual Tour/Floorplan:
View
Year Built: 2015
Listing Number: 226000537
Status Code: A-Active
Taxes: $4,578.04
Tax Year: 2024
Garage:
2
Furnishings: Negotiable
Pets Allowed: With Approval
Interior Features:
Bar
Built-In Cabinets
Custom Mirrors
Foyer
Laundry Tub
Smoke Detectors
Walk-In Closet(s)
Window Coverings
Amenities:
Basketball Court
Barbecue
Bike And Jog Path
Bocce Court
Clubhouse
Park
Pool
Community Room
Spa/Hot Tub
Dog Park
Fitness Center
Pickleball
Play Area
Sidewalk
Streetlight
Tennis Court(s)
Underground Utility
Financial Information:
Taxes: $4,578.04
Tax Year: 2024
Master Association Fees: $1,455.00
Association Fee: $6,220.00
Exterior Features:
Screened Lanai/Porch
Built In Grill
Equipment:
Auto Garage Door
Cooktop - Gas
Dishwasher
Disposal
Dryer
Generator
Grill - Gas
Microwave
Range
Refrigerator
Refrigerator/Freezer
Refrigerator/Icemaker
Security System
Self Cleaning Oven
Smoke Detector
Washer
View:
Landscaped Area
Additional Information:
Building Description: Dsl/Cable Available
Building Design: Villa Attached
Community Type: Gated
MLS Area: Na37 - East Collier S/O 75 E/O 9
Total Floors: 1
Water: Central
Construction: Concrete Block, Stucco
Foreclosure: No
Short Sale: No
Date Listed: 2026-01-26 20:17:03
Pool: No
Pool Type: Community
Private Spa: No
Furnished: Negotiable
Kitchen Description: Pantry
Windows: Window Coverings
Parking: Driveway Paved, Attached
Garage Spaces: 2
Flooring: Carpet, Tile
Roof: Tile
Heating: Central Electric
Cooling: Ceiling Fan(S), Central Electric
Fireplace: No
Storm Protection: Shutters Electric, Shutters - Manual
Security: Security System, Smoke Detector(S), Gated Community
Laundry: Laundry Tub
Irrigation: Central
55+ Community: No
Pets: With Approval
Restrictions: Deeded
Maintenance: Fidelity Bond, Lawn/Land Maintenance, Legal/Accounting, Manager, Rec Facilities, Security, Street Lights, Street Maintenance, Trash Removal
Rear Exposure: Se
Lot Desc.: Oversize
Amenities: Basketball Court, Barbecue, Bike And Jog Path, Bocce Court, Clubhouse, Park, Pool, Community Room, Spa/Hot Tub, Dog Park, Fitness Center, Pickleball, Play Area, Sidewalk, Streetlight, Tennis Court(S), Underground Utility
Map of 7176 Live Oak Dr, Naples, FL 34114
Listing Courtesy Of: John R Wood Properties
David@ThinkNaples.com