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
Sold for $599,900
$599,900
7255 Live Oak DR, NAPLES, FL 34114
2beds
1,659sqft
Single Family Residence
Built in 2015
7,187 Square Feet Lot
$600,000 Zestimate®
$362/sqft
$5,641 Estimated rent
Home value
$600,000
$540,000 - $666,000
$5,641/mo
Zestimate® history
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List your homeWhat's special
Screened lanaiNice private south waterviewCustom storage cabinets
Zillow last checked:
Listing updated:
Listed by:
Linda Covino 978-808-3440,
Royal Shell Real Estate, Inc.
Bought with:
Linda Covino
Royal Shell Real Estate, Inc.
Source: SWFLMLS,MLS#: 226002887
Originating MLS: Naples
Originating MLS: NaplesFacts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 2
- Bathrooms: 2
- Full bathrooms: 2
Rooms
- Room types: Den - Study, Screened Lanai/Porch, 2 Bedrooms Plus Den
Bedroom
- Features: First Floor Bedroom
Dining room
- Features: Dining - Living
Kitchen
- Features: Gas Available
Heating
- Natural Gas
Cooling
- Central Air
Appliances
- Included: Electric Cooktop, Dishwasher, Disposal, Dryer, Microwave, Refrigerator/Icemaker, Self Cleaning Oven, Tankless Water Heater, Washer
- Laundry: Washer/Dryer Hookup, Inside
Features
- Pull Down Stairs, Den - Study, Laundry in Residence, Screened Lanai/Porch
- Flooring: Tile
- Windows: Shutters Electric, Shutters - Manual
- Has fireplace: No
Interior area
- Total structure area: 1,750
- Total interior livable area: 1,659 sqft
Property
Parking
- Total spaces: 2
- Parking features: Driveway, Attached
- Attached garage spaces: 2
- Has uncovered spaces: Yes
Features
- Stories: 1
- Patio & porch: Screened Lanai/Porch
- Pool features: Community
- Spa features: Community
- Has view: Yes
- View description: Lake
- Has water view: Yes
- Water view: Lake
- Waterfront features: None
Lot
- Size: 7,187 Square Feet
- Features: Regular
Details
- Parcel number: 82679001623
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Ranch
- Property subtype: Single Family Residence
Materials
- Block, Stucco
- Foundation: Concrete Block
- Roof: Tile
Condition
- New construction: No
- Year built: 2015
Utilities & green energy
- Gas: Natural
- Water: Central
Community & HOA
Community
- Features: Clubhouse, Pool, Dog Park, Fitness Center, Restaurant, Sidewalks, Street Lights, Gated
- Security: Gated Community
- Subdivision: WINDING CYPRESS
HOA
- Has HOA: Yes
- Amenities included: Bike And Jog Path, Bocce Court, Clubhouse, Pool, Spa/Hot Tub, Dog Park, Fitness Center, Internet Access, Library, Pickleball, Restaurant, Sidewalk, Streetlight, Underground Utility
- HOA fee: $6,648 annually
Location
- Region: Naples
Financial & listing details
- Price per square foot: $362/sqft
- Tax assessed value: $636,212
- Annual tax amount: $5,242
- Date on market: 1/23/2026
- Lease term: Buyer Finance/Cash
Price history
| Date | Event | Price |
|---|---|---|
| 4/30/2026 | Sold | $599,900$362/sqft |
Source:  SWFLMLS #226002887 Report a problem | ||
| 4/6/2026 | Pending sale | $599,900$362/sqft |
Source: SWFLMLS #226002887 Report a problem | ||
| 3/25/2026 | Price change | $599,900-6.3%$362/sqft |
Source: SWFLMLS #226002887 Report a problem | ||
| 3/2/2026 | Price change | $639,900-5.9%$386/sqft |
Source: SWFLMLS #226002887 Report a problem | ||
| 2/23/2026 | Price change | $679,900-2.9%$410/sqft |
Source: SWFLMLS #226002887 Report a problem | ||
| 2/2/2026 | Price change | $699,900-2.8%$422/sqft |
Source: SWFLMLS #226002887 Report a problem | ||
| 1/23/2026 | Listed for sale | $719,900$434/sqft |
Source: SWFLMLS #226002887 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $5,488 +4.7% | $371,291 +2.9% |
| 2024 | $5,242 +63.6% | $360,827 +3% |
| 2023 | $3,204 -2.7% | $350,317 +3% |
| 2022 | $3,292 -0.9% | $340,114 +3% |
| 2021 | $3,322 +2.4% | $330,208 +1.4% |
| 2020 | $3,243 +1.9% | $325,649 +2.3% |
| 2019 | $3,183 +2.4% | $318,327 +1.9% |
| 2018 | $3,110 -29.7% | $312,392 +2.1% |
| 2017 | $4,427 +1.2% | $305,967 +2.1% |
| 2016 | $4,372 +1.8% | $299,674 +1231.9% |
| 2015 | $4,297 | $22,500 |
Find assessor info on the county website
Neighborhood: Winding Cypress
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Nearby schools
GreatSchools rating
- 7/10Lely Elementary SchoolGrades: PK-5Distance: 2.5 mi
- 7/10Manatee Middle SchoolGrades: 6-8Distance: 1.7 mi
- 5/10Lely High SchoolGrades: 9-12Distance: 2.4 mi
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- Florida
- Collier County
- Naples
- 34114
- Winding Cypress
- 7255 Live Oak DR
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