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$699,900

  • For Sale
  • Active
  • Single Family
  • 2 Beds
  • 2 Full Baths
  • 1,659 Sq. Ft.

Next open house:

Open House: 3:00 PM - 4:00 PM

Sunday 2/22 3:00 PM - 4:00 PM

7255 Live Oak Dr,Naples, FL 34114

7255 Live Oak DrNaplesFL34114

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This home has just been freshly painted inside and out. professionally painted kitchen and bath cabinets, nice private south west waterview , screened lanai able to enlarge or even add a pool. Previous owner had a great workshop in garage with 8 overhead lights, 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 This home is ready for immediate occupancy 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

Full Property Details for 7255 Live Oak Dr

General

  • Price: $699,900
  • HOA FEE: $554/month
  • HOA FEE FREQ.: Quarterly
  • Taxes: (2024)
  • Status: Active
  • Type: Single Family
  • Source: Bonita_Springs
  • MLS ID: 226002887
  • Updated: 2/2/2026
  • Added to Site: 29 day(s) ago

Rental Information

  • Lease/Rent Term: 30
  • Min. Lease (Days): 30

Interior

  • Interior Features: Split Bedrooms, Den - Study, Wired for Data
  • Appliances: Electric Cooktop, Dishwasher, Disposal, Dryer, Microwave, Refrigerator with Icemaker, Self-Cleaning Oven, Tankless Water Heater, Washer
  • Furnishings: Partially
  • Flooring: Tile

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2
  • Primary Bathroom: Shower Only

Bedrooms

  • Total Bedrooms: 2

Other Rooms

  • Dining Room: Dining - Living
  • Laundry: Washer/Dryer Hookup, Inside

Additional Information

  • Shared Amenities: Bike And Jog Path, Bocce Court, Clubhouse, Pool, Community Spa/Hot tub, Dog Park, Fitness Center, Internet Access, Library, Pickleball, Restaurant, Sidewalks, Street Lights, Gated

Exterior

  • Porch/Patio/Deck: Screened Lanai/Porch

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Covered Spaces: 2
  • Parking Features: Driveway Paved, Attached

Location

  • Area: NA37 - East Collier S/O 75 E/O 9
  • County: Collier
  • Subdivision: WINDING CYPRESS
  • Building Name: WINDING CYPRESS
  • Direction Faces: North

Community

  • Association: Yes
  • Assoc. Fees Include: Insurance, Irrigation Water, Maintenance Grounds, Legal/Accounting, Manager, Reserve, Security, Sewer, Street Lights, Street Maintenance
  • Units Assoc/Comm: 766
  • Pets Allowed: Yes
  • Management Type: On-Site

Heating & Cooling

  • Air Conditioning: Yes
  • Cooling Type: Central Electric
  • Heating Type: Natural Gas

Utilities

  • Gas: Natural
  • Sewer: Central
  • Water: Central
  • Cable Available: Yes
  • Utility Description: Underground Utilities, Natural Gas Connected, Cable Available, Natural Gas Available

Structural Information

  • Description/Design: Single Family Residence
  • Exterior Const.: Concrete Block, Stucco
  • Roof: Tile
  • Windows: Double Hung, Shutters Electric, Shutters - Manual
  • Stories/Levels: 1
  • Stories in Building: 1
  • Square Feet: 1,659
  • Sq. Ft. Source: Property Appraiser Office
  • Living Area: 1,659 Sq. Ft.
  • Year Built: 2015

Lot Features

  • Property View: Lake
  • Lot Size (Acres): 0.165
  • Lot Size (Sq. Ft.): 7,187
  • Lot Size Source: Property Appraiser Office
  • Lot Dimensions: 53 x 53 x 135 x 135
  • Frontage: Public Road
  • Frontage Feet: 53
  • Irrigation System: Central
  • Lot Features: Regular
  • Lot Description: Regular

Water Features

  • Water Front Desc.: None, Pond
  • Canal Width: None

Financial Considerations

  • Association Fee: $1,662
  • Assoc Fee Freq.: Quarterly
  • Application Fee: $280
  • Tax Year: 2024
  • Terms: Buyer Finance/Cash

Disclosures and Reports

  • Ownership: Single Family
  • Legal Description: WINDING CYPRESS PHASE ONE LOT 46
  • Property ID: 82679001623
  • Section: 35
  • Lot Number: 46

Listed by Royal Shell Real Estate, Inc.

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Listing agent

— 7255 Live Oak Dr —

  • Royal Shell Real Estate, Inc.

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 7255 Live Oak Dr

School District:Collier County School District
NameGradesDistance
Lely Elementary School
8125 Lely Cultural Parkway, Naples, FL 34113
PK-52.5 mi
Manatee Middle School
1920 Manatee Road, Naples, FL 34114
6-81.7 mi
Lely High School
1 Lely High School Boulevard, Naples, FL 34113
9-122.4 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 7255 Live Oak Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
2/02/2026
Price Reduced
$699,900
-2.78%
MLS
1/23/2026
Listed
$719,900
104.18%
MLS
9/09/2015
Sold
$352,580
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 7255 Live Oak Dr

Year
Property Taxes
Change
Tax Assessment
Change
2025
$5,488
5%
$371,291
3%
2024
$5,242
1%
$360,827
3%
2023
$5,202
10%
$350,317
6%
2021
$4,734
1%
$330,208
-3%
2022
$4,709
-1%
$340,114
4%
2021
$4,734
3%
$325,649
2%
2019
$4,587
4%
$318,327
2%
2018
$4,427
1%
$312,392
2%
2017
$4,372
2%
$305,967
2%
2016
$4,297
1534%
$299,674
1232%
2015
$263
—
$22,500
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by Royal Shell Real Estate, Inc.

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7255 Live Oak Dr, Naples, FL 34114 (MLS# 226002887) is a Single Family property with 2 bedrooms and 2 full bathrooms. 7255 Live Oak Dr is currently listed for $699,900 and was received on January 23, 2026. Want to learn more about 7255 Live Oak Dr? Do you have questions about finding other Single Family real estate for sale in Naples? You can browse all Naples real estate or contact a Coldwell Banker agent to request more information.

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