7255 Live Oak Dr Naples, FL 34114
Winding Cypress NeighborhoodEstimated payment $4,150/month
Highlights
- Fitness Center
- Lake View
- Pond
- Gated with Attendant
- Clubhouse
- Attic
About This Home
This home has just been freshly painted inside and out. professionally painted kitchen and bath cabinets, nice private south waterview , screened lanai able to enlarge or expand with a pool. Previous owner had a great workshop in garage with 8 overhead lights, addition dual media cat5/rg6 charging station for a Tesla , framed peg boards for hanging tools , custom storage cabinets and a pull down staircase for added storage. Home features 2 bedrooms 2 baths plus den a whole house generator and attached manual and electric storm shutters. Remaining furniture in home is staying. Live Oak is a beautiful mature tree lined street on cul de sac and just a short walk to the amenity center, dog park or community garden .Rarely will you find a single family home at this price in Winding Cypress . Great Value ! Winding Cypress amenity center offers so much within its gates, its own Shady Palm restaurant, resort pool , gym , bocci and pickleball courts, dog park , walking trails and so much more. Winding Cypress is a gated community located just mins to 75, downtown and Marco Island. Photos to be uploaded on 1/24
Listing Agent
Linda Covino
Royal Shell Real Estate, Inc. License #448500405 Listed on: 01/23/2026
Home Details
Home Type
- Single Family
Est. Annual Taxes
- $5,242
Year Built
- Built in 2015
Lot Details
- 7,187 Sq Ft Lot
- Lot Dimensions are 53 x 135 x 53 x 135
- Home has North and South Exposure
- Rectangular Lot
HOA Fees
- $554 Monthly HOA Fees
Parking
- 2 Car Attached Garage
- Driveway
Home Design
- Tile Roof
- Stucco
Interior Spaces
- 1,659 Sq Ft Home
- 1-Story Property
- Partially Furnished
- Electric Shutters
- Double Hung Windows
- Combination Dining and Living Room
- Den
- Screened Porch
- Tile Flooring
- Lake Views
- Pull Down Stairs to Attic
- Security Gate
Kitchen
- Self-Cleaning Oven
- Electric Cooktop
- Microwave
- Ice Maker
- Dishwasher
- Disposal
Bedrooms and Bathrooms
- 2 Bedrooms
- Split Bedroom Floorplan
- 2 Full Bathrooms
- Shower Only
- Separate Shower
Laundry
- Dryer
- Washer
Outdoor Features
- Pond
- Screened Patio
- Lanai
Utilities
- Central Air
- Heating System Uses Gas
- Underground Utilities
- Tankless Water Heater
- High Speed Internet
- Cable TV Available
Listing and Financial Details
- Tax Lot 46
- Assessor Parcel Number 82679001623
Community Details
Overview
- Association fees include management, insurance, irrigation water, legal/accounting, ground maintenance, reserve fund, road maintenance, sewer, street lights, security
- Association Phone (239) 261-3440
- Winding Cypress Subdivision
Amenities
- Restaurant
- Clubhouse
- Community Library
Recreation
- Pickleball Courts
- Bocce Ball Court
- Fitness Center
- Community Pool
- Community Spa
- Dog Park
- Trails
Security
- Gated with Attendant
- Card or Code Access
Map
Home Values in the Area
Average Home Value in this Area
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 | $5,488 | $371,291 | -- | -- |
| 2024 | $5,202 | $360,827 | -- | -- |
| 2023 | $5,202 | $350,317 | $0 | $0 |
| 2022 | $4,709 | $340,114 | $0 | $0 |
| 2021 | $4,734 | $330,208 | $0 | $0 |
| 2020 | $4,651 | $325,649 | $0 | $0 |
| 2019 | $4,587 | $318,327 | $0 | $0 |
| 2018 | $4,427 | $312,392 | $0 | $0 |
| 2017 | $4,372 | $305,967 | $0 | $0 |
| 2016 | $4,297 | $299,674 | $0 | $0 |
| 2015 | $263 | $22,500 | $0 | $0 |
Property History
| Date | Event | Price | List to Sale | Price per Sq Ft |
|---|---|---|---|---|
| 04/30/2026 04/30/26 | Pending | -- | -- | -- |
| 03/25/2026 03/25/26 | Price Changed | $599,900 | -6.3% | $362 / Sq Ft |
| 03/02/2026 03/02/26 | Price Changed | $639,900 | -5.9% | $386 / Sq Ft |
| 02/23/2026 02/23/26 | Price Changed | $679,900 | -2.9% | $410 / Sq Ft |
| 02/02/2026 02/02/26 | Price Changed | $699,900 | -2.8% | $422 / Sq Ft |
| 01/23/2026 01/23/26 | For Sale | $719,900 | -- | $434 / Sq Ft |
Purchase History
| Date | Type | Sale Price | Title Company |
|---|---|---|---|
| Warranty Deed | $352,580 | Pgp Title |
Mortgage History
| Date | Status | Loan Amount | Loan Type |
|---|---|---|---|
| Open | $334,951 | New Conventional |
Source: Florida Gulf Coast Multiple Listing Service
MLS Number: 226002887
APN: 82679001623
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Ask me questions while you tour the home.