Listing Provided Courtesy of John R Wood Properties
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.
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
MLS #:
226000537
Status:
Active
Beds:
3
Baths:
2
Type:
Villa – Attached
Subtype:
Villa Attached
Subdivision:
WINDING CYPRESS
Neighborhood:
windingcypress
Listed Date:
Jan 11, 2026
Finished Sq Ft:
1,554
Total Sq Ft:
1,934
Year Built:
2015
See this Listing
Schools
Interior
Appliances
Gas Cooktop, Dishwasher, Disposal, Dryer, Grill – Gas, Microwave, Range, Refrigerator, Refrigerator/Freezer, Refrigerator/Icemaker, Self Cleaning Oven, Washer
Bathrooms
2 Full Bathrooms
Cooling
Ceiling Fan(s), Central Electric
Flooring
Carpet, Tile
Heating
Central Electric
Laundry Features
Laundry Tub
Exterior
Architectural Style
Ranch, Villa Attached
Association 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
Community Features
Clubhouse, Park, Pool, Dog Park, Fitness Center, Sidewalks, Street Lights, Tennis Court(s), Gated
Construction Materials
Concrete Block, Stucco
Exterior Features
Screened Lanai/Porch, Built In Grill
Other Structures
Tennis Court(s)
Parking Features
Driveway Paved, Attached
Parking Spots
2
Roof
Tile
Security Features
Security System, Smoke Detector(s), Gated Community
Financial
HOA Fee
$6,220
Tax Year
2024
Taxes
$4,578
Map
Community
- Address7176 Live Oak DR NAPLES FL
- SubdivisionWINDING CYPRESS
- CityNAPLES
- CountyCollier
- Zip Code34114
Market Summary
Current real estate data for Villa – Attached in NAPLES as of Feb 03, 2026
449
Villa – Attached Listed
114
Avg DOM
397
Avg $ / SqFt
$721,283
Avg List Price
Property Summary
- Located in the WINDING CYPRESS subdivision, 7176 Live Oak DR NAPLES FL is a Villa – Attached for sale in NAPLES, FL, 34114. It is listed for $550,000 and features 3 beds, 2 baths, and has approximately 1,554 square feet of living space, and was originally constructed in 2015. The current price per square foot is $354. The average price per square foot for Villa – Attached listings in NAPLES is $397. The average listing price for Villa – Attached in NAPLES is $721,283. To schedule a showing of MLS#226000537 at 7176 Live Oak DR in NAPLES, FL, contact your Carney Realty & Associates, Inc. agent at 239-574-1965.
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