$615,000
2 Bed 2 Bath SingleFamilyResidence for Sale in WINDING CYPRESS, FL
7248 Live Oak Drive, Naples, FL, 34114
About this home
This charming model is the perfect fit featuring an inviting open-floor concept where natural light streams through the windows. The kitchen boasts granite counters, stainless appliances and a center island and extra storage for everyday use and easy entertaining. The pantry closet has plenty of space for all of your staple goods. Tile floors are throughout much of the space. There's a den/flex room with french doors that can be used as an additional bedroom when needed or office, hobby or quiet sitting room. Additional guest bedroom and bathroom with combined tub and shower and granite topped vanity offers privacy for your family and guests. The laundry room features a spacious storage area with shelving for your all your supplies. There are storage racks in the two car garage to house your coolers for the beach. Be sure to take time to relax and enjoy your morning beverage and the beautiful sunsets on the screened lanai that overlooks the OVERSIZED lot with mature landscaping complete with an outdoor kitchen with grill, sink, and fridge for your convenience. Winding Cypress is a sought after, gated community and is appreciated for its active, social lifestyle and world class amenities. It’s nestled within 800 acres of natural preserve and 80 acres of serene lakes teeming with migratory wildlife. Head over to the clubhouse with state-of-the-art fitness center, locker rooms with showers, movement room for classes, internet café, event room, catering kitchen, resort-style pool with spa and cabanas, restaurant with bar, firepit, pickleball, tennis and bocce courts. Take the pups to play in the dog park. Walk or ride your bike on the many paths including the peaceful preserve boardwalk. If gardening is your passion, there is a community garden to grow your favorite vegetables. HOA management and friendly staff are onsite to assist and coordinate regular events for all to enjoy. Minutes from beaches, golfing, fishing, boating, shopping, and cultural activities. It's time to enjoy the Florida lifestyle!
Property details
- Type
- SingleFamilyResidence
- Year built
- 2016
- Interior
- 1,685 sqft
- Lot size
- 6,969.6 sqft
- Acreage
- 0.16 acres
- Garage
- 2 car
- Days on market
- 191
- Total association fees
- $6,174/yr (~$515/mo)
- CDD
- None
- Est. taxes (1.4%)
- $8,610/yr
- Flood zone (area est.)
- Not available
- Storm protection
- None listed
- Exposure
- Southeast
- Waterfront
- No
- Gulf access
- No
- Gulf access type
- N/A
- Pool
- No
- Spa
- No
- Natural gas
- Yes
- Water
- Public
- Sewer
- Public Sewer
- New construction
- No
- Pets
- Call, Conditional
- County
- Collier
Total association fees sums the core association dues the MLS feed provides (HOA, condo/master association, and land lease), normalized to a yearly figure. These are separate from and additional to specialty charges — mandatory club or food-and-beverage minimums, special assessments, and rec-lease fees — which the IDX feed does not carry. Always confirm the full fee schedule with the HOA or listing agent.
Maintenance included in the fee
What the association dues cover, per the MLS. Confirm the full schedule with the HOA.
Amenities
Based on the $/sqft of 4 comparable homes sold nearby in the last 12 months. Indicative, not an appraisal.
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Recently sold nearby
Closed comparable sales within ~1 mile in the last 12 months — similar price, size, beds/baths, and age.
| Address | Sold | Sold price | Beds/Baths | Sq ft | $/sqft |
|---|---|---|---|---|---|
| 7255 Live Oak Drive | Apr 2026 | $599,900 | 2/2 | 1,659 | $362 |
| 7121 Live Oak Drive | Jun 2026 | $580,000 | 2/2 | 1,554 | $373 |
| 7370 Mockingbird Court | Dec 2025 | $645,000 | 2/2 | 1,805 | $357 |
| 8612 Genova Court | May 2026 | $599,000 | 3/2 | 1,542 | $388 |
| Average | 4 comps | $605,975 | $370 |
Market trends — Naples
Median of closed MLS sales each month over the available window. Months with too few sales are omitted; the range extends automatically as more sales close.
Live area medians from the MLS · see all listings. Indicative, not an appraisal.
Price & status history
Down $54,900 (8.4%) from the original list price.
| May 22, 2026 | Sold | $595,000 |
| Mar 21, 2026 | Price reducedfrom $634,999 | $615,000 |
| Oct 1, 2025 | Listed | $649,900 |
The good, the trade-offs & the location
- Built 2016 — post-2002 Florida wind codes (typically lower insurance)
- 2-car garage
Straight-line distances to major SWFL amenities — approximate; actual drive times vary.
Nearby schools
Get more information on their programs, scores, and extracurriculars on each school's page · browse the full schools directory.
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Listing information is provided in part by the Florida Gulf Coast Multiple Listing Service (MLS) through its Broker Reciprocity / Internet Data Exchange (IDX) program. Properties displayed may be listed by brokerages other than SWFL Relocation Team. Data is deemed reliable but is not guaranteed accurate by the MLS or this brokerage and should be independently verified. Fees, flood zones, taxes, square footage, and school assignments are estimates from the feed and must be confirmed. © 2026 SWFL Relocation Team. All rights reserved.