Mediterranean / spanish home featuring a tile roof, stucco siding, decorative driveway, and a garage

1 / 49

7255 Live Oak Dr., Naples, FL 34114

$599,900 Sold

Beds
2
Baths
2
Sq Ft
1,659
Built
2015

MLS# 226002887 Listed at $599,900 Sold April 30, 2026

Fees & taxes

Annual fees
$6,648
One-time fees
$1,330
Seller’s 2024 taxes
$5,242

Community

Winding Cypress

Questions about this home?
Ask about this home or what available homes are like it.

Ask about this home

Listing description

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

Property details

Building & ownership

Ownership
Single Family
Furnishings
Partially
Building style
Ranch, Single Family
Floor plan
Split Bedrooms
Construction
Concrete Block, Stucco
Roof
Tile
Lot size
0.165 acres
Lot description
Regular

Interior

Features
Pull Down Stairs
Flooring
Tile
Cooling
Central Electric
Bedroom details
First Floor Bedroom
Additional rooms
Den - Study, Laundry in Residence, Screened Lanai/Porch

Kitchen & dining

Kitchen
Gas Available
Appliances
Electric Cooktop, Dishwasher, Disposal, Dryer, Microwave, Refrigerator/Icemaker, Self Cleaning Oven, Tankless Water Heater, Washer
Dining
Dining - Living

Outdoor & view

View
Lake
Rear exposure
South
Exterior
Screened Lanai/Porch
Storm protection
Shutters Electric, Shutters - Manual

Parking

Garage
Yes
Car port
No
Spots
2
Description
Driveway Paved, Attached

Pool & spa

Private pool
No
Private spa
No
Community pool
Yes
Pool description
Community
Spa description
Community

Waterfront

Waterfront
No
Description
None
Gulf access
No
Canal
None
Boat / dock
None

Community amenities

Amenities
Bike And Jog Path, Bocce Court, Clubhouse, Pool, Spa/Hot Tub, Dog Park, Fitness Center, Internet Access, Library, Pickleball, Restaurant, Sidewalk, Streetlight, Underground Utility
Golf
No Golf Available
Elevator
None
Security
Gated Community

What the fees cover

Maintenance
Insurance, Irrigation Water, Lawn/Land Maintenance, Legal/Accounting, Manager, Reserve, Security, Sewer, Street Lights, Street Maintenance

Pets & leasing

Pets allowed
Yes
Leases per year
3
Minimum lease
30 days
Restrictions
No Commercial, No RV

Additional details

Parcel number
82679001623
Potential short sale
No

Listing last updated May 1, 2026

Listing courtesy of Royal Shell Real Estate, Inc. · 239-261-9101

Broker Reciprocity Program

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.

Destinations & driving times from 7255 Live Oak 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.

Dining & Shopping near 7255 Live Oak Dr., Naples, FL 34114 – #226002887, by driving distance
NameMilesETA
Fifth Avenue South 10.6 mi 21 min
Third Street South 11.7 mi 24 min
Coastland Center 12.7 mi 25 min
Venetian Village 14.8 mi 29 min
Waterside Shops 17.2 mi 30 min
Galleria Shoppes at Vanderbilt 17.4 mi 30 min
Mercato 19.6 mi 34 min
Miromar Outlets 29.3 mi 41 min
Coconut Point 30 mi 44 min
Gulf Coast Town Center 33.7 mi 45 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.

Hurricane evacuation zone

Zone D Collier

Called in the fourth wave, for stronger storms.

Called firstCalled last
FEMA flood zone

Zone AE

1% annual chance, with a set base flood elevation

The building 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.

A starting point, not a determination. Your lender will require its own flood zone determination before closing, and your insurer will normally require an elevation certificate — a surveyor’s measurement of how high the building actually sits — before quoting. Those documents govern; this does not replace either. Zones can also be amended individually through FEMA.

Flood zones, evacuation, and insurance are explained in the Risk, Resilience & Insurance chapter of the 2027 Naples Buyer’s Guide.

Flood zones across Winding Cypress

Jeffrey Waldman

Jeffrey Waldman

REALTOR® and Owner, Naples Abodes

Call (239) 450-3763 Text (239) 450-3763

Florida License SL3295589

“We would recommend him to anyone.”
Frank & Vicki Vavricka

Ask me about this home

How should I reply?

Or book a call with me

Pick a day and a time that suit you and I will call.