7775 Winding Cypress Dr, Naples, FL 34114
For Sale $990,000
Save Property
Thank you for taking a look at the best value in sought after Winding Cypress! This pristine, 2-Story Summerwood Model, is loaded with options and is located on one of the nicest, private, and quiet lots in the entire community. This amazing home is perfectly situated on a lake's edge with a preserve backdrop. It's on a cul-de-sac with no thru traffic, and miles off of major roadways so it's incredibly quiet, private, with no road noise. If you are looking for a luxurious and functional space to entertain guests, or have them spend some overnights visiting, this is the property for you. Pride of original ownership is clear. With over 3200 square feet there's incredible room to entertain while also providing privacy for visitors. This home boasts 4 bedrooms, 3 full baths, and a large office or flex room that can be used as the new owner desires. The upstairs area is expansive with a huge gathering space that can be used as a theater room, craft area, media room, or office. The upstairs has it's own large bedroom and full bathroom. The 2nd floor also has it's own zoned climate control with a dedicated additional HVAC unit. The upgrades and amenities that this property offers are impressive. These features include: an upgraded kitchen package that adds optional cabinets, quartz counters & premium appliances, plank tile flooring, an incredible extended great room gathering space, built-in saltwater pool w/integral spa, a whole house generator, easy-use accordion shutters, hurricane rated electric shades enclosing the lanai, an outdoor summer kitchen, surround sound ceiling speakers, an upgraded, private owner's suite, built-in closet organizers, convenient interior plantation shutters, and a deep 2 car garage with epoxy flooring and a must have 2nd refrigerator. Winding Cypress is an amenity rich, natural gas community and a hidden gem of Naples. Meet friends and neighbors at the resident's only, full-service restaurant and bar that's conveniently located at the edge of the incredible resort pool. Play pickleball, tennis, or bocce on the premium lighted courts. Take advantage of the world-class fitness center. Enjoy the nature trail boardwalk, dog parks, and community garden. Participate in any of the huge selection of activities that the community and HOA offers. Speaking of the HOA, you will not find a better value for cost anywhere in Naples. It's not even close. The HOA General Manager, Assistant Manager, Activities Director, and Support Staff are all full-time and on site to better assist the residents. Winding Cypress is conveniently located just 10 minutes to the beaches and entertainment on Marco Island, 15 minutes to all that downtown Olde Naples has to offer, 10 minutes to I75, and just 35 minutes to RSW Airport.
Built-In Cabinets
French Doors
Pantry
Smoke Detectors
Wired for Sound
Walk-In Closet(s)
Window Coverings
Bike And Jog Path
Bocce Court
Clubhouse
Pool
Community Room
Dog Park
Fitness Center
Internet Access
Library
Pickleball
Restaurant
Sidewalk
Streetlight
Tennis Court(s)
Underground Utility
Taxes: $8,560.16
Tax Year: 2025
Association Fee: $6,656.00
Association Description: Mandatory
Screened Lanai/Porch
Outdoor Kitchen
Gas Cooktop
Dishwasher
Disposal
Double Oven
Dryer
Microwave
Range
Refrigerator/Icemaker
Self Cleaning Oven
Wall Oven
Washer
Y
Lake
Building Description: Two Story, Single Family
Community Type: Gated
MLS Area: Winding Cypress
Total Square Footage: 3,206
Total Floors: 2
Water: Central
Construction: Concrete Block, Stucco
Date Listed: 2026-10-25 00:00:00
Pool: Y
Pool Description: Community, Below Ground, Concrete, Gas Heat, Salt Water
Private Spa: Y
Furnished: Unfurnished
Kitchen Description: Gas Available, Island, Pantry
Windows: Window Coverings
Parking: Driveway Paved, Attached
Garage Description: Y
Garage Spaces: 2
Attached Garage: Y
Flooring: Carpet, Tile
Roof: Tile
Heating: Central Electric, Natural Gas, Zoned
Cooling: Ceiling Fan(S), Central Electric
Storm Protection: Shutters Electric, Shutters - Manual, Shutters - Screens/Fabric
Security: Smoke Detector(S), Gated Community
Laundry: Laundry In Residence
Irrigation: Central
Pets: With Approval
Restrictions: Architectural, Deeded, No Commercial
Maintenance: Cable, Insurance, Internet/Wi Fi Access, Irrigation Water, Lawn/Land Maintenance, Legal/Accounting, Manager, Rec Facilities, Repairs, Reserve, Security, Street Lights, Street Maintenance
Rear Exposure: Ne
Lot Desc.: Across From Waterfront, Cul-De-Sac
Amenities: Bike And Jog Path, Bocce Court, Clubhouse, Pool, Community Room, Dog Park, Fitness Center, Internet Access, Library, Pickleball, Restaurant, Sidewalk, Streetlight, Tennis Court(S), Underground Utility
Listing Courtesy Of: William Raveis Real Estate
theresa.bocka@raveis.com
Thank you for taking a look at the best value in sought after Winding Cypress! This pristine, 2-Story Summerwood Model, is loaded with options and is located on one of the nicest, private, and quiet lots in the entire community. This amazing home is perfectly situated on a lake's edge with a preserve backdrop. It's on a cul-de-sac with no thru traffic, and miles off of major roadways so it's incredibly quiet, private, with no road noise. If you are looking for a luxurious and functional space to entertain guests, or have them spend some overnights visiting, this is the property for you. Pride of original ownership is clear. With over 3200 square feet there's incredible room to entertain while also providing privacy for visitors. This home boasts 4 bedrooms, 3 full baths, and a large office or flex room that can be used as the new owner desires. The upstairs area is expansive with a huge gathering space that can be used as a theater room, craft area, media room, or office. The upstairs has it's own large bedroom and full bathroom. The 2nd floor also has it's own zoned climate control with a dedicated additional HVAC unit. The upgrades and amenities that this property offers are impressive. These features include: an upgraded kitchen package that adds optional cabinets, quartz counters & premium appliances, plank tile flooring, an incredible extended great room gathering space, built-in saltwater pool w/integral spa, a whole house generator, easy-use accordion shutters, hurricane rated electric shades enclosing the lanai, an outdoor summer kitchen, surround sound ceiling speakers, an upgraded, private owner's suite, built-in closet organizers, convenient interior plantation shutters, and a deep 2 car garage with epoxy flooring and a must have 2nd refrigerator. Winding Cypress is an amenity rich, natural gas community and a hidden gem of Naples. Meet friends and neighbors at the resident's only, full-service restaurant and bar that's conveniently located at the edge of the incredible resort pool. Play pickleball, tennis, or bocce on the premium lighted courts. Take advantage of the world-class fitness center. Enjoy the nature trail boardwalk, dog parks, and community garden. Participate in any of the huge selection of activities that the community and HOA offers. Speaking of the HOA, you will not find a better value for cost anywhere in Naples. It's not even close. The HOA General Manager, Assistant Manager, Activities Director, and Support Staff are all full-time and on site to better assist the residents. Winding Cypress is conveniently located just 10 minutes to the beaches and entertainment on Marco Island, 15 minutes to all that downtown Olde Naples has to offer, 10 minutes to I75, and just 35 minutes to RSW Airport.
Property Details
Price: $990,000
Sq Ft: 3,206
($309 per
sqft)
Bedrooms: 4
Bathrooms: 3
City: Naples
County: Collier
Type: Single Family
Development: Winding Cypress
Acres: 0.2000
Year Built: 2019
Listing Number: 226037594
Status Code: A-Active
Taxes: $8,560.16
Tax Year: 2025
Garage:
2
/
Y
Furnishings: Unfurnished
Pets Allowed: With Approval
Interior Features:
Built-In Cabinets
French Doors
Pantry
Smoke Detectors
Wired for Sound
Walk-In Closet(s)
Window Coverings
Amenities:
Bike And Jog Path
Bocce Court
Clubhouse
Pool
Community Room
Dog Park
Fitness Center
Internet Access
Library
Pickleball
Restaurant
Sidewalk
Streetlight
Tennis Court(s)
Underground Utility
Financial Information:
Taxes: $8,560.16
Tax Year: 2025
Association Fee: $6,656.00
Association Description: Mandatory
Exterior Features:
Screened Lanai/Porch
Outdoor Kitchen
Equipment:
Gas Cooktop
Dishwasher
Disposal
Double Oven
Dryer
Microwave
Range
Refrigerator/Icemaker
Self Cleaning Oven
Wall Oven
Washer
View:
Y
Waterfront Description:
Lake
Additional Information:
Building Description: Two Story, Single Family
Community Type: Gated
MLS Area: Winding Cypress
Total Square Footage: 3,206
Total Floors: 2
Water: Central
Construction: Concrete Block, Stucco
Date Listed: 2026-10-25 00:00:00
Pool: Y
Pool Description: Community, Below Ground, Concrete, Gas Heat, Salt Water
Private Spa: Y
Furnished: Unfurnished
Kitchen Description: Gas Available, Island, Pantry
Windows: Window Coverings
Parking: Driveway Paved, Attached
Garage Description: Y
Garage Spaces: 2
Attached Garage: Y
Flooring: Carpet, Tile
Roof: Tile
Heating: Central Electric, Natural Gas, Zoned
Cooling: Ceiling Fan(S), Central Electric
Storm Protection: Shutters Electric, Shutters - Manual, Shutters - Screens/Fabric
Security: Smoke Detector(S), Gated Community
Laundry: Laundry In Residence
Irrigation: Central
Pets: With Approval
Restrictions: Architectural, Deeded, No Commercial
Maintenance: Cable, Insurance, Internet/Wi Fi Access, Irrigation Water, Lawn/Land Maintenance, Legal/Accounting, Manager, Rec Facilities, Repairs, Reserve, Security, Street Lights, Street Maintenance
Rear Exposure: Ne
Lot Desc.: Across From Waterfront, Cul-De-Sac
Amenities: Bike And Jog Path, Bocce Court, Clubhouse, Pool, Community Room, Dog Park, Fitness Center, Internet Access, Library, Pickleball, Restaurant, Sidewalk, Streetlight, Tennis Court(S), Underground Utility
Map of 7775 Winding Cypress Dr, Naples, FL 34114
Listing Courtesy Of: William Raveis Real Estate
theresa.bocka@raveis.com