Seller's Agent in 2025
Kendra Hoefs
Realty One Group MVP
(239) 770-3345
33 in this area
57 Total Sales
6839 Winding Cypress Dr Naples, FL 34114
Winding Cypress Neighborhood
3
Beds
3
Baths
2,515
Sq Ft
9,583
Sq Ft Lot
Highlights
- Lake Front
- Concrete Pool
- Gated Community
- Fitness Center
- Solar Power System
- Clubhouse
About This Home
As of November 2025This Pinnacle floorplan is situated on the largest lake in the neighborhood and features 3 bedrooms, a den, 3 bathrooms, a pool and spa, and a 3-car garage. The open-concept layout includes a dramatic zero-corner slider that seamlessly connects indoor and outdoor living spaces. Peace of mind comes with a whole-home generator and impact-resistant windows and doors. Inside, you'll find extensive upgrades throughout. The kitchen boasts built-in appliances and a spacious island—perfect for entertaining. Additional highlights include soaring tray ceilings, crown molding in the den and entry, and tile flooring throughout. The air-conditioned 3-car (extended by 4 ft) garage offers ample storage with custom shelving and a built-in workbench. Outdoors, the heated pool and spa are powered by both gas and solar, a smart, energy-efficient combination. The expansive outdoor kitchen, hurricane screens for added protection, and generous deck space create an ideal setting for sunset views. Other exterior features include lush landscaping with low-voltage lighting, an extra-wide driveway (recently sealed), a custom designed screened-in entryway, and panoramic wide lake views. Winding Cypress is a natural gas community with resort-style amenities! Dine at Shady Palm, the onsite restaurant, or enjoy pickleball, bocce, tennis, a state-of-the-art fitness center, a resort-style pool, a community garden, and even 2 dog parks for your furry friend. This pet-friendly community allows rentals, has low fees, and boasts a prime location—convenient to Marco Island, 5th Avenue, and I-75.
Home Details
Home Type
- Single Family
Est. Annual Taxes
- $10,690
Year Built
- Built in 2021
Lot Details
- 9,583 Sq Ft Lot
- 65 Ft Wide Lot
- Lake Front
- Rectangular Lot
HOA Fees
- $554 Monthly HOA Fees
Parking
- 3 Car Attached Garage
Home Design
- Concrete Block With Brick
- Concrete Foundation
- Stucco
- Tile
Interior Spaces
- Property has 1 Level
- Crown Molding
- Cathedral Ceiling
- Combination Dining and Living Room
- Den
- Library
- Screened Porch
- Tile Flooring
- Lake Views
- Fire and Smoke Detector
Kitchen
- Self-Cleaning Oven
- Grill
- Gas Cooktop
- Microwave
- Dishwasher
- Kitchen Island
- Disposal
Bedrooms and Bathrooms
- 3 Bedrooms
- Split Bedroom Floorplan
- 3 Full Bathrooms
Laundry
- Laundry in unit
- Dryer
- Washer
Eco-Friendly Details
- Solar Power System
Pool
- Concrete Pool
- Solar Heated In Ground Pool
- Heated Spa
- In Ground Spa
- Gas Heated Pool
- Solar Heated Spa
Outdoor Features
- Outdoor Kitchen
- Attached Grill
Utilities
- Central Air
- Heating Available
- Underground Utilities
- Power Generator
- Gas Available
Listing and Financial Details
- Assessor Parcel Number 82679021027
Community Details
Overview
- Winding Cypress Subdivision
- Mandatory home owners association
Amenities
- Restaurant
- Clubhouse
Recreation
- Tennis Courts
- Pickleball Courts
- Bocce Ball Court
- Fitness Center
- Community Pool
- Community Spa
- Dog Park
- Bike Trail
Security
- Gated Community
Ownership History
Date
Name
Owned For
Owner Type
Purchase Details
Listed on
Jul 2, 2025
Closed on
Nov 21, 2025
Sold by
Oleary Edward J and Oleary Revocable Trust
Bought by
Defibaugh Jerold J and Hollander Linda J
Seller's Agent
Kendra Hoefs
Realty One Group MVP
Buyer's Agent
Diane Mato
Premier Sotheby's Int'l Realty
List Price
$1,350,000
Sold Price
$1,260,000
Premium/Discount to List
-$90,000
-6.67%
Views
31
Home Financials for this Owner
Home Financials are based on the most recent Mortgage that was taken out on this home.
Avg. Annual Appreciation
10.35%
Purchase Details
Closed on
Jan 26, 2023
Sold by
Oleary Gail P and Oleary Edward J
Bought by
Oleary Revocable Trust
Purchase Details
Listed on
Dec 15, 2020
Closed on
Feb 24, 2021
Sold by
Divosta Homes Lp
Bought by
Oleary Gail P and Oleary Edward J
Seller's Agent
Matthew Peacock
MVP Realty Associates LLC
Buyer's Agent
Debbie Coats
Downing Frye Realty Inc.
List Price
$826,580
Sold Price
$815,000
Premium/Discount to List
-$11,580
-1.4%
Home Financials for this Owner
Home Financials are based on the most recent Mortgage that was taken out on this home.
Avg. Annual Appreciation
9.66%
Original Mortgage
$365,000
Interest Rate
2.7%
Mortgage Type
New Conventional
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Home Values in the Area
Average Home Value in this Area
Purchase History
| Date | Type | Sale Price | Title Company |
|---|---|---|---|
| Warranty Deed | $1,260,000 | None Listed On Document | |
| Warranty Deed | -- | -- | |
| Warranty Deed | $815,000 | Pgp Title |
Source: Public Records
Mortgage History
| Date | Status | Loan Amount | Loan Type |
|---|---|---|---|
| Previous Owner | $365,000 | New Conventional |
Source: Public Records
Property History
| Date | Event | Price | List to Sale | Price per Sq Ft | Prior Sale |
|---|---|---|---|---|---|
| 11/21/2025 11/21/25 | Sold | $1,260,000 | -6.7% | $501 / Sq Ft | |
| 09/16/2025 09/16/25 | Pending | -- | -- | -- | |
| 07/02/2025 07/02/25 | For Sale | $1,350,000 | +65.6% | $537 / Sq Ft | |
| 02/24/2021 02/24/21 | Sold | $815,000 | -1.8% | $328 / Sq Ft | View Prior Sale |
| 01/27/2021 01/27/21 | Pending | -- | -- | -- | |
| 01/22/2021 01/22/21 | Price Changed | $829,580 | +0.4% | $333 / Sq Ft | |
| 12/15/2020 12/15/20 | For Sale | $826,580 | -- | $332 / Sq Ft |
Source: Naples Area Board of REALTORS®
Tax History
| Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
|---|---|---|---|---|
| 2025 | $10,690 | $867,682 | -- | -- |
| 2024 | $10,622 | $843,228 | -- | -- |
| 2023 | $10,622 | $818,668 | $0 | $0 |
| 2022 | $10,284 | $794,823 | $220,915 | $573,908 |
| 2021 | $2,956 | $36,495 | $0 | $0 |
| 2020 | $2,151 | $33,177 | $33,177 | $0 |
| 2019 | $2,073 | $26,021 | $26,021 | $0 |
Source: Public Records
Agents Affiliated with this Home
-
Kendra Hoefs
-
Diane Mato
Buyer's Agent in 2025
Diane Mato
Premier Sotheby's Int'l Realty
(239) 777-7358
4 in this area
64 Total Sales
-
M
Seller's Agent in 2021
Matthew Peacock
MVP Realty Associates LLC
-
Debbie Coats
D
Buyer's Agent in 2021
Debbie Coats
Downing Frye Realty Inc.
(239) 370-9622
2 in this area
11 Total Sales
Map
Source: Naples Area Board of REALTORS®
MLS Number: 225060759
APN: 82679021027
Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.
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.
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