7775 Winding Cypress Dr, Naples, Florida 34114
Overview
- 226037594
- Single Family Residence, Residential
- 4
- 3
- 2
- 3206 Sqft
- 0.2 Acres
- 2019
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.
What Will You Pay to Insure This Property?
Annual insurance estimates for this ZIP code, property type, and price tier. SWFL-specific breakdown.
SELLING?
We Are ONE % Commission.
Realty of Naples FL
When you list at 1% commission with Realty of Naples, Scott handles your sale personally — not a call center, not a junior agent. 35 years of Naples negotiation experience working every offer to your bottom line.
The valuation is free, the conversation is free, and there's zero obligation. The only thing you risk by reaching out is finding out how much more than 1% commission you've been paying.
8515 Chase Preserve Dr, Naples, Florida 34113
8515 Chase Preserve DR, 34113, Naples, LELY RESORTResidential - Single Family Residence
2730 2nd St Ne, Naples, Florida 34120
2730 2nd NE ST, 34120, Naples, GOLDEN GATE ESTATESResidential - Single Family Residence
718 Regency Reserve Cir 3104, Naples, Florida 34119
718 Regency Reserve CIR, 34119, Naples, VINEYARDSResidential - Low Rise (1-3)
What Does the HOA Actually Cost — and Cover?
Your true monthly payment goes well beyond the mortgage. Here's the full picture including HOA, taxes, and insurance.
Estimated Annual Property Tax — This Property
Based on Collier County millage rates and Florida exemption rules.
Around this property
How Far Is Everything from This Property?
Real drive times calculated from this address — not straight-line distance.
What Will This Home Actually Cost Over 5 & 10 Years?
Beyond the mortgage — taxes, insurance, HOA, maintenance, and projected equity. Pre-filled from this listing.
SELLING?
We Are ONE % Commission.
Realty of Naples FL
When you list at 1% commission with Realty of Naples, Scott handles your sale personally — not a call center, not a junior agent. 35 years of Naples negotiation experience working every offer to your bottom line.
The valuation is free, the conversation is free, and there's zero obligation. The only thing you risk by reaching out is finding out how much more than 1% commission you've been paying.
1% Total Commission On The Sale Of Your Home
Everything a full-service brokerage does to make your home stand out — for a 1% commission.
1
Photo Enhancement
Professional editing brings every photo to life — balanced exposure, corrected color, bright skies, and rich, true-to-life detail, finished to a magazine standard. Those first images decide whether a buyer clicks through or scrolls past. We make sure yours stop the scroll.
2
Drone Photography
Aerial photography captures the lot, the rooflines, the water or golf views, and the surrounding neighborhood. For waterfront, golf course, and acreage properties, drone imagery is often the deciding factor — showcasing proximity to the Gulf, canal access, or a private setting in a single frame.
3
Virtual Staging
Empty rooms are digitally furnished with tasteful, realistic furniture and decor, helping buyers picture themselves in the space. Staged homes consistently sell faster and for more, and virtual staging delivers that advantage at a fraction of the cost of physical staging. We tailor each room to the buyer most likely to purchase.
4
3D Virtual Tours
Immersive, interactive walkthroughs let buyers explore every room on their own time, from anywhere in the country. With a true sense of layout, flow, and scale, a 3D tour pre-qualifies interest. For our many Northeast clients moving to Southwest Florida, it's often the tool that lets them decide on a home they've never set foot in.
5
Cinematic Storytelling
Professionally produced video tours walk buyers through the home and the lifestyle around it. We craft each video as a story — pacing the reveal of key spaces, highlighting the features buyers care about most, and capturing the feel of the home. This is the content that gets shared, saved, and remembered, extending your listing's reach far beyond the MLS.
6
Luxury Presentation
Your home is presented with the polish high-end buyers expect — refined layouts, premium imagery, and placement built to stand out. From the headline copy to the order of the photos, every detail is intentional, designed to communicate value and justify your asking price. For luxury and estate properties we expand into print exposure, magazine features, and dedicated campaigns.
Who Lives Here — and What Has the Market Done?
Demographics and 5-year price trends for this area. Key data for buyers relocating from the Northeast.
Days on Market & Price History
Listing activity for this property.
Schools Serving This Property
Public school assignments for this address based on ZIP code boundaries.
Price Per Sq Ft — How Does This Home Compare?
Flood Risk Assessment — This Property
Hurricane Risk Assessment — This Property
Historical storm track data and risk scoring for this ZIP code.
Estimate Your Monthly Payment
Pre-filled with data from this listing. Adjust any field.
Interested in this property?
Realty of Naples represents buyers and sellers across Southwest Florida at 1% commission. Whether you want to schedule a showing or list your own home, our team saves you tens of thousands compared to a traditional brokerage.
127 Washington AVE, FORT MYERS BEACH FL 33931
- $518,250
- 0.1113 Acres
- Residential Lot, Land
17731 Canal Cove Ct, Fort Myers Beach, Florida 33931
- $625,000
- Beds: 3
- Baths: 2
- Garage: 1
- 0.163 Acres
- Manufactured Home, Residential
Details
-
Property ID 226037594
-
Price $990,000
-
Property Size 3206 Sqft
-
Land Area 0.2 Acres
-
Bedrooms 4
-
Bathrooms 3
-
Garages 2
-
Year Built 2019
-
Property Status Active, For Sale
-
Property Type Single Family Residence, Residential
Additional details
-
Association Fee 6656
-
Roof Tile
-
Cooling Ceiling Fan(s), Central Electric
-
Heating Central Electric, Natural Gas, Zoned
-
Flooring Carpet, Tile
-
County Collier
-
Property Type Residential
-
Pool Community, Below Ground, Concrete, Gas Heat, Salt Water
-
Parking Driveway Paved, Attached
-
Community Features Clubhouse, Pool, Dog Park, Fitness Center, Restaurant, Sidewalks, Street Lights, Tennis Court(s), Gated
-
Waterfront Lake
-
Architectural Style Two Story, Single Family
- Scott Cowan
