7775 Winding Cypress Dr. – #226037594

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7775 Winding Cypress Dr., Naples, FL 34114

$990,000 For Sale

Beds
4
Baths
3
Sq Ft
3,206
Built
2019

Open house · Sunday, November 15 · 2–4 p.m.

MLS# 226037594 20 days on market

Fees & taxes

Annual fees
$6,656
One-time fees
$1,330
Seller’s 2025 taxes
$8,560

Questions about this home?
Ask about this home or arrange a tour.

Listing description

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

Building & ownership

Ownership
Single Family
Furnishings
Unfurnished
Building style
Two Story, Single Family
Floor plan
Great Room, Split Bedrooms, 2 Story
Construction
Concrete Block, Stucco
Roof
Tile
Lot size
0.2 acres
Lot description
Across From Waterfront, Cul-De-Sac

Interior

Features
Built-In Cabinets, French Doors, Pantry, Smoke Detectors, Wired for Sound, Walk-In Closet(s), Window Coverings
Flooring
Carpet, Tile
Cooling
Ceiling Fan(s), Central Electric
Additional rooms
Den - Study, Great Room, Guest Bath, Guest Room, Home Office, Laundry in Residence, Media Room, Screened Lanai/Porch

Kitchen & dining

Kitchen
Gas Available, Island, Pantry
Appliances
Gas Cooktop, Dishwasher, Disposal, Double Oven, Dryer, Microwave, Range, Refrigerator/Icemaker, Self Cleaning Oven, Wall Oven, Washer

Outdoor & view

View
Lake, Landscaped Area, Preserve
Rear exposure
Northeast
Exterior
Screened Lanai/Porch, Outdoor Kitchen
Storm protection
Shutters Electric, Shutters - Manual, Shutters - Screens/Fabric

Parking

Garage
Yes
Car port
No
Spots
2
Description
Driveway Paved, Attached

Pool & spa

Private pool
Yes
Private spa
Yes
Community pool
Yes
Pool description
Community, Below Ground, Concrete, Gas Heat, Salt Water
Spa description
Community, Below Ground

Waterfront

Waterfront
Yes
Description
Lake
Gulf access
No
Boat / dock
None

Community amenities

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
Golf
No Golf Available
Elevator
None

What the fees cover

Maintenance
Cable, Insurance, Internet/WiFi Access, Irrigation Water, Lawn/Land Maintenance, Legal/Accounting, Manager, Rec Facilities, Repairs, Reserve, Security, Street Lights, Street Maintenance

Pets & leasing

Pets allowed
With Approval
Number allowed
3
Weight limit
150 lbs
Leases per year
3
Minimum lease
30 days
Restrictions
Architectural, Deeded, No Commercial

Additional details

Parcel number
82679019822
Potential short sale
No

Listing last updated November 13, 2026

Listing courtesy of William Raveis Real Estate · 239-231-3380

Property taxes for a new owner

Estimated property taxes about $12,000 a year at the county’s value of this home and its 1.04% tax rate, including $2,486 in charges not based on value, no exemptions applied

On the county’s 2026 roll, the seller’s bill is about $8,600, lower because of a homestead exemption and a capped assessment, which end when the home sells.

If you make this home your primary residence, a homestead exemption would lower this figure. If you have also had a Florida homestead in any of the last three years, you may be able to carry up to $500,000 of its capped-value savings to this home, which Florida calls “portability.” Both are applied for with the Property Appraiser by March 1.

How a new owner’s property taxes are set is explained in the Costs & Taxes chapter of the 2027 Naples Buyer’s Guide.

Estimated from the Collier County Property Appraiser’s 2026 value of this home and its tax rate, plus its 2025 charges not based on value from the Collier County Tax Collector’s roll. The county sets a new value each January 1, so a new owner’s first full bill can differ.

Destinations & driving times from 7775 Winding Cypress Dr

Every destination named here is described in the Destinations chapter of the 2027 Naples Buyer’s Guide.

Driving times are estimated from this home’s location, using OpenStreetMap road data.

Dining & Shopping near 7775 Winding Cypress Dr. – #226037594, by driving distance
NameMilesETA
Fifth Avenue South 12.1 mi 26 min
Third Street South 13.3 mi 30 min
Coastland Center 14.2 mi 31 min
Venetian Village 16.4 mi 35 min
Waterside Shops 18.4 mi 34 min
Galleria Shoppes at Vanderbilt 18.6 mi 35 min
Mercato 20.8 mi 39 min
Miromar Outlets 30.5 mi 46 min
Coconut Point 31.3 mi 49 min
Gulf Coast Town Center 34.9 mi 49 min

Flood zones & evacuation

Two different things, measured by two different agencies. Evacuation zones are about storm surge and who leaves first. Flood zones are FEMA’s insurance rating, and they vary from home to home.

Hurricane evacuation zone

Zone D Collier

Called in the fourth wave, for stronger storms.

Called firstCalled last
FEMA flood zone

Zone AE

1% annual chance, with a set base flood elevation

The lot is inside a Special Flood Hazard Area, where a federally backed mortgage requires flood insurance.

FEMA flood maps and Collier County Emergency Management. A revised Collier County flood map is in preparation and may change these zones.

A starting point, not a determination. Your lender will require its own flood zone determination before closing, and your insurer will normally require an elevation certificate — a surveyor’s measurement of how high the building actually sits — before quoting. Those documents govern; this does not replace either. Zones can also be amended individually through FEMA.

Flood zones, evacuation, and insurance are explained in the Risk, Resilience & Insurance chapter of the 2027 Naples Buyer’s Guide.

Flood zones across Winding Cypress

Jeffrey Waldman

Jeffrey Waldman

REALTOR® and Owner, Naples Abodes

Call (239) 450-3763 Text (239) 450-3763

Florida License SL3295589

“By far, Jeff has been the best.”
Ray & Diane Kolodziej

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