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
Community
Winding CypressQuestions about this home?
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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
The source of this real property information is the copyrighted and proprietary database compilation of the M.L.S. of Naples, Inc. Copyright 2026 M.L.S. of Naples, Inc. All rights reserved. The accuracy of this information is not warranted or guaranteed. This information should be independently verified if any person intends to engage in a transaction in reliance upon it.
Displayed under License No. SL3295589.
Property taxes for a new owner
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.
| Name | Miles | ETA |
|---|---|---|
| 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 |
| Name | Miles | ETA |
|---|---|---|
| Nearest beach access: Naples Beach at 8th Ave. S. | 13 mi | 29 min |
| Naples Municipal Beach and Pier | 13.4 mi | 30 min |
| Tigertail Beach Park | 13.7 mi | 32 min |
| Lowdermilk Park | 14.2 mi | 31 min |
| Via Miramar Beach | 15.8 mi | 35 min |
| Clam Pass Park | 18.9 mi | 36 min |
| Vanderbilt Beach Park | 21.7 mi | 40 min |
| Delnor-Wiggins Pass State Park | 23.6 mi | 41 min |
| Barefoot Beach Preserve | 28.3 mi | 45 min |
| Bonita Beach | 28.5 mi | 45 min |
| Lovers Key State Park | 33.2 mi | 55 min |
| Name | Miles | ETA |
|---|---|---|
| Gulfshore Playhouse | 12.1 mi | 26 min |
| Sugden Community Theatre | 12.3 mi | 27 min |
| Artis—Naples | 18.7 mi | 35 min |
| Music & Arts Community Center | 39.8 mi | 56 min |
| Barbara B. Mann Performing Arts Hall | 44.1 mi | 63 min |
| Name | Miles | ETA |
|---|---|---|
| Sugden Regional Park | 9.3 mi | 21 min |
| Paradise Coast Sports Complex | 9.7 mi | 23 min |
| Naples Botanical Garden | 10 mi | 24 min |
| Baker Park | 12.3 mi | 27 min |
| Cambier Park | 12.4 mi | 27 min |
| Gordon River Greenway Park | 13.5 mi | 28 min |
| Naples Zoo | 13.7 mi | 30 min |
| Fred W. Coyle Freedom Park | 14.9 mi | 29 min |
| North Collier Regional Park | 20.8 mi | 38 min |
| Big Corkscrew Island Regional Park | 24.1 mi | 45 min |
| Corkscrew Swamp Sanctuary | 29.7 mi | 54 min |
| Name | Miles | ETA |
|---|---|---|
| Physicians Regional Collier Blvd. | 4.4 mi | 13 min |
| NCH Baker Downtown | 13 mi | 29 min |
| Physicians Regional Pine Ridge Rd. | 14.6 mi | 28 min |
| NCH North Naples Hospital | 21.3 mi | 36 min |
| Name | Miles | ETA |
|---|---|---|
| Marco Island Executive Airport (MKY) | 10.2 mi | 26 min |
| Naples Airport (APF) | 12 mi | 27 min |
| Southwest Florida International Airport (RSW) | 41.1 mi | 59 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.
Zone D Collier
Called in the fourth wave, for stronger storms.
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.
Flood zones, evacuation, and insurance are explained in the Risk, Resilience & Insurance chapter of the 2027 Naples Buyer’s Guide.
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.”
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