NOT LISTED FOR SALE

7239 Live Oak Dr Naples, FL 34114

Winding Cypress Neighborhood

Estimated Value: $1,326,000 - $1,544,000

4 Beds
4 Baths
3,656 Sq Ft
$401/Sq Ft Est. Value

Sale Details

Date Sold: May 2, 2022

Last sale price $1,610,000 $440 Per Sq Ft

Est. 9% decrease in value since last sale

Current estimated payment $9,466 / mo

285 Days on Market

Highlights

  • Lake Front
  • Gated with Attendant
  • Sitting Area In Primary Bedroom
  • Community Cabanas
  • Media Room
  • Floor-to-Ceiling Windows

About This Home

As of May 2022

H2469 - Welcome to Winding Cypress! Recently renovated Gourmet Kitchen with top of the line appliances: Miele, Wolfe & Sub-Zero (gas range, refrigerator, double oven, wine cooler, coffee station, steam oven), Generac 22KW Generator, 2 Trane A/C's, Super Screen picture window w/ Beautiful lake views, shiplap accent walls & ceilings for that beachy feel and for peace of mind, Hurricane Impact Doors & Windows. Winding Cypress is a new resort style community that has a community center with resort style pool, tennis, pickleball, exercise room, sidewalks, dog park and of course a poolside bar/restaurant.

Last Agent to Sell the Property

Momma Bee Fagan

Coldwell Banker Realty Listed on: 04/28/2021

Coldwell Banker Realty

Last Buyer's Agent

Dawn Conard

Realty One Group MVP

Home Details

Home Type

  • Single Family

Est. Annual Taxes

  • $9,233

Year Built

  • Built in 2016

Lot Details

  • 11,761 Sq Ft Lot
  • Lot Dimensions are 57 x 135 x 119 x 135
  • Lake Front
  • Southeast Facing Home
  • Gated Home
  • Paved or Partially Paved Lot
  • Sprinkler System

HOA Fees

  • $380 Monthly HOA Fees

Parking

  • 3 Car Attached Garage
  • Automatic Garage Door Opener

Home Design

  • Concrete Block With Brick
  • Stucco
  • Tile

Interior Spaces

  • 3,656 Sq Ft Home
  • 2-Story Property
  • 3 Ceiling Fans
  • Ceiling Fan
  • Single Hung Windows
  • Floor-to-Ceiling Windows
  • Bay Window
  • Entrance Foyer
  • Family or Dining Combination
  • Media Room
  • Den
  • Loft
  • Screened Porch
  • Lake Views

Kitchen

  • Breakfast Bar
  • Built-In Double Oven
  • Gas Cooktop
  • Ice Maker
  • Dishwasher
  • Kitchen Island
  • Built-In or Custom Kitchen Cabinets
  • Disposal

Flooring

  • Carpet
  • Tile

Bedrooms and Bathrooms

  • 4 Bedrooms
  • Sitting Area In Primary Bedroom
  • Primary Bedroom on Main
  • Split Bedroom Floorplan
  • In-Law or Guest Suite
  • 4 Full Bathrooms
  • Dual Sinks
  • Shower Only

Laundry

  • Laundry Room
  • Washer
  • Laundry Tub

Home Security

  • Monitored
  • High Impact Windows
  • High Impact Door

Pool

  • Screened Pool
  • Concrete Pool
  • Heated In Ground Pool
  • Heated Spa
  • In Ground Spa
  • Saltwater Pool
  • Screened Spa

Outdoor Features

  • Patio
  • Outdoor Kitchen

Schools

  • Manatee Elementary School
  • Manatee Middle School
  • Lely High School

Utilities

  • Central Heating and Cooling System
  • Cooling System Mounted In Outer Wall Opening
  • Power Generator
  • High Speed Internet
  • Cable TV Available

Listing and Financial Details

  • Assessor Parcel Number 82679001704

Community Details

Overview

  • $1,000 Secondary HOA Transfer Fee
  • Mandatory home owners association

Amenities

  • Restaurant
  • Clubhouse
  • Community Library

Recreation

  • Pickleball Courts
  • Bocce Ball Court
  • Exercise Course
  • Community Cabanas
  • Community Pool or Spa Combo
  • Dog Park
  • Bike Trail

Security

  • Gated with Attendant

Home Details

Home Type

Single Family

Est. Annual Taxes

$9,233

Year Built

Built in 2016

Lot Details

0.27 Acres

HOA Fees

$380 per month

Parking

3

Listing Details

  • Legal Description: WINDING CYPRESS PHASE ONE LOT 50
  • Property Type: Residential
  • Table: Residential
  • Building Design: Single Family
  • Building Description: 2 Story
  • Storm Protection: Impact Resistant Doors, Impact Resistant Windows
  • Year Built: 2016
  • Special Features: None
  • Property Sub Type: Detached
  • Stories: 2

Interior Features

  • Furnished Description: Unfurnished
  • Numberof Ceiling Fans: 3
  • Price Per Sq Ft: 440.37
  • Total Floors: 2
  • Additional Rooms: Guest Bath, Guest Room, Laundry in Residence, Loft, Media Room, Screened Lanai/Porch, Den/Study
  • Estimated Living Area: 3656
  • Full Bathrooms: 4
  • Total Bathrooms: 4.00
  • Bedroom Description: First Floor Bedroom, Master BR Ground, Master BR Sitting Area
  • Bedrooms: 4+Den
  • Total Bedrooms: 4
  • Dining Room: Breakfast Bar, Family Dining
  • Equipment: Auto Garage Door, Cooktop - Gas, Dishwasher, Disposal, Double Oven, Generator, Range, Refrigerator, Refrigerator/Icemaker, Steam Oven, Wall Oven, Washer
  • Flooring: Carpet, Tile
  • Floor Plan: Split Bedrooms, 2 Story
  • Interior Amenities: Built-In Cabinets, Foyer, High Speed Available, Laundry Tub
  • Kitchen: Island
  • Primary Bathroom: Dual Sinks, Shower Only
  • Windows: Bay, Impact Resistant, Single Hung

Exterior Features

  • Gulf Access: No
  • Private Pool: Yes
  • Private Spa: Yes
  • Roof: Tile
  • Construction: Concrete Block
  • Irrigation: Reclaimed
  • Road: Paved Road
  • View: Lake
  • Exterior Features: Outdoor Kitchen, Patio, Sprinkler Auto
  • Exterior Finish: Stucco
  • Private Pool Type: Below Ground, Concrete, Heated Gas, Salt Water System, Screened
  • Private Spa Type: Below Ground, Concrete, Heated Gas, Screened
  • Waterfront Type: Lake

Garage/Parking

  • Garage Description: Attached
  • Garage Spaces: 3
  • Parking: Driveway Paved

Utilities

  • Cable Available: Yes
  • Cooling: Ceiling Fans, Central Electric, Wall Unit
  • Heat: Central Electric
  • Security: Monitored Alarm, Gated, Guard At Gate, Private Security System (Leased)
  • Sewer: Central
  • Water: Central

Condo/Co-op/Association

  • Approval: Application Fee, Buyer
  • Management: Professional
  • Mandatory HOA: Yes
  • Restrictions: No Commercial
  • Sub Condo Name: WINDING CYPRESS
  • HOA Fees: 1140
  • HOA Fee Frequency: Quarterly
  • Maintenance: Irrigation Water, Lawn/Land Maintenance, Legal/Accounting, Manager, Recreational Facilities, Reserve, Security, Street Lights, Street Maintenance, Trash Removal

Association/Amenities

  • Pets: No Approval Needed
  • Development: Winding Cypress
  • Amenities: Bike And Jog Path, Bocce Court, Cabana, Clubhouse, Community Pool, Community Spa/Hot tub, Dog Park, Exercise Room, Internet Access, Library, Pickleball, Restaurant, Sidewalk
  • Community Type: Gated

Fee Information

  • Transfer Fees: 1000.00
  • Application Fee: 50.00

Schools

  • Elementary School: Manatee Elementary
  • High School: Lely High School
  • Middle School: Manatee Middle School

Lot Info

  • Builder Product: No
  • Section: 35
  • Total Area: 5000
  • Waterfront: Yes
  • Acres: 0.2700
  • Rear Exposure: Southeast
  • Lot Description: Oversize
  • Lot Dimensions: 57 X 135 X 119 X 135
  • Parcel Number: 82679001704

Rental Info

  • Lease Limits: Yes
  • Leases Per Year: 4
  • Min Days Of Lease: 90

Tax Info

  • Tax Description: County Only, Homestead
  • Tax District Type: Community Development District
  • Taxes: 9233.00

Ownership History

We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.

Date Name Owned For Owner Type

Purchase Details

Closed on
Oct 17, 2025
Sold by
Bought by
Current Estimated Value
$1,467,679

Purchase Details

Listed on
Apr 28, 2021
Closed on
May 2, 2022
Sold by
Bought by
Seller's Agent
Momma Bee Fagan
Coldwell Banker Realty
Buyer's Agent
Dawn Conard
Realty One Group MVP
List Price
$1,490,000
Sold Price
$1,610,000
Premium/Discount to List
$120,000
8.05%

Home Financials for this Owner

Home Financials are based on the most recent Mortgage that was taken out on this home.
Avg. Annual Appreciation
-2.24%

Purchase Details

Closed on
Mar 25, 2016
Sold by
Bought by

Home Financials for this Owner

Home Financials are based on the most recent Mortgage that was taken out on this home.
Original Mortgage
$403,000
Interest Rate
3.65%
Mortgage Type
New Conventional

Purchase Details

Closed on
Mar 1, 2016
Bought by

Home Financials for this Owner

Home Financials are based on the most recent Mortgage that was taken out on this home.
Original Mortgage
$403,000
Interest Rate
3.65%
Mortgage Type
New Conventional
Source: Public Records

Range of Values:

--
Value Increase
--
Percent Increase
--
Adjusted for Inflation
Collateral Analytics

Collateral Analytics Collateral Analytics AVMs (Automated Valuation Model) employ a number of statistical approaches combined with neighborhood-specific comparable selection guarantees the most up-to-date and precise valuations.

Not Available

Collateral Analytics does not have data for the current month. Please view the chart for historical values.

ICE

ICE Mortgage Technology ICE Mortgage Technology’s AVM (Automated Valuation Model) is a state-of-the-art online residential property valuation tool that provides a quick and accurate estimate of the value of almost any home in the U.S.

Not Available

ICE Mortgage Technology does not have data for the current month. Please view the chart for historical values.

First American

First American First American Data & Analytics’ next-generation AVM combines unrivaled data assets with a blended ensemble of valuation models to produce highly accurate, reliable valuations you can trust.

Not Available

First American does not have data for the current month. Please view the chart for historical values.

Quantarium

Quantarium Quantarium’s valuation service, repeatedly proven the industry’s most accurate and comprehensive, is supercharged with a self-learning and auto-tuning AI engine that continually becomes smarter and more accurate as it processes daily inputs from the industry’s leading RE data lake.

Not Available

Quantarium does not have data for the current month. Please view the chart for historical values.

Average Value
Not Available
List Price
Sold Price
Create a Home Valuation Report for This Property
The Home Valuation Report is an in-depth analysis detailing your home's value as well as a comparison with similar homes in the area

Home Values in the Area

Source: Public Records

Average Home Value in this Area

Source: Public Records

Purchase History

We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.

Date Buyer Sale Price Title Company
-- None Listed On Document
$1,610,000 First American Title
$733,401 Pgp Title
$733,100 --
Source: Public Records

Mortgage History

We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.

Date Status Borrower Loan Amount
Previous Owner $403,000
Source: Public Records

Property History

We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.

Date Event Price List to Sale Price per Sq Ft
05/02/2022 05/02/22 Sold $1,610,000 +8.1% $440 / Sq Ft
02/07/2022 02/07/22 Pending -- -- --
02/03/2022 02/03/22 For Sale $1,490,000 -7.5% $408 / Sq Ft
08/04/2021 08/04/21 Off Market $1,610,000 -- --
05/30/2021 05/30/21 Price Changed $1,490,000 -5.4% $408 / Sq Ft
04/28/2021 04/28/21 For Sale $1,575,000 -- $431 / Sq Ft
Source: Naples Area Board of REALTORS®

Tax History

We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.

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 $13,993 $1,187,380 $652,747 $534,633
2024 $12,977 $1,159,817 -- --
2023 $12,977 $1,054,379 $373,418 $680,961
2022 $9,160 $736,434 $0 $0
2021 $9,234 $714,984 $0 $0
2020 $9,048 $705,112 $182,071 $523,041
2019 $9,036 $699,647 $0 $0
2018 $8,786 $686,602 $206,408 $480,194
2017 $8,809 $683,986 $200,549 $483,437
2016 $3,570 $188,832 $0 $0
2015 $263 $22,500 $0 $0
Source: Public Records

Agents Affiliated with this Home

  • Momma Bee Fagan

    Seller's Agent in 2022

    Momma Bee Fagan

    Coldwell Banker Realty

    (239) 304-6136

    1 in this area

    65 Total Sales

    Momma Bee Fagan
    Section Image

  • D

    Buyer's Agent in 2022

    Dawn Conard

    Realty One Group MVP

    (973) 202-0680

    1 in this area

    48 Total Sales

    Dawn Conard
    Section Image
See All Agents

Map

Source: Naples Area Board of REALTORS®

MLS Number: 221036282

Naples Area Board of REALTORS®

APN: 82679001704

Florida Collier County Naples 34114 Winding Cypress

7239 Live Oak Dr, Naples, FL

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.

Naples Area Board of REALTORS® 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.

Nearby Homes
Your Personal Tour Guide

Ask me questions while you tour the home.