$599,000
2 Bed 2 Bath SingleFamilyResidence for Sale in WINDING CYPRESS, FL
7121 Live Oak Drive, Naples, FL, 34114
About this home
Nestled within the gated, amenity-rich community of Winding Cypress, this thoughtfully designed turnkey furnished two-bedroom plus den, two-bath residence offers an exceptional blend of comfort, quality, and relaxed Florida living. The open floor plan is enhanced by wood flooring throughout the main living areas, along with crown molding, and a distinctive coffered ceiling in the living and dining area, creating a refined yet inviting atmosphere. The kitchen is both elegant and functional, featuring 42" white cabinetry, granite countertops, tile backsplash, undercabinet lighting, and stainless-steel appliances—ideal for everyday living and entertaining alike. A flexible den with French doors provides the option for a private home office, media room, or additional guest space. Seamless indoor-outdoor living is achieved through the expansive custom lanai, designed for entertaining with an outdoor kitchen complete with gas grill, refrigerator, and sink, an above-ground HotSprings hot tub with beautiful outdoor furnishings including a dining table for six, over-sized parasol umbrellas that provide shade, and picture-frame lanai screens that showcase peaceful preserve surroundings. Additional highlights include a whole-house gas generator, two-car garage, and plantation shutters. Winding Cypress is a natural gas community thoughtfully designed around preserved natural beauty and an active, social lifestyle. At its heart is an impressive clubhouse with a heated resort-style pool and spa, poolside dining at The Shady Palm, state-of-the-art fitness center, library, and community gathering rooms. Other amenities include pickleball and tennis courts, bocce courts, dog parks, a community garden, and scenic walking and nature trails. Known for its welcoming atmosphere and beautifully maintained grounds, Winding Cypress offers a true sense of community while remaining conveniently close to everything Naples has to offer. A six-passenger well-maintained golf cart is included for effortless access throughout the neighborhood.
Property details
- Type
- SingleFamilyResidence
- Year built
- 2016
- Interior
- 1,554 sqft
- Lot size
- 6,534 sqft
- Acreage
- 0.15 acres
- Garage
- 2 car
- Days on market
- 76
- Total association fees
- $5,764/yr (~$480/mo)
- CDD
- None
- Est. taxes (1.4%)
- $8,386/yr
- Flood zone (area est.)
- Not available
- Storm protection
- Impact Windows/Doors, Shutters
- Exposure
- Northwest
- Waterfront
- No
- Gulf access
- No
- Gulf access type
- N/A
- Pool
- No
- Spa
- Yes
- 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 |
|---|---|---|---|---|---|
| 7248 Live Oak Drive | May 2026 | $595,000 | 2/2 | 1,685 | $353 |
| 7255 Live Oak Drive | Apr 2026 | $599,900 | 2/2 | 1,659 | $362 |
| 8612 Genova Court | May 2026 | $599,000 | 3/2 | 1,542 | $388 |
| 8748 Querce Court | Aug 2025 | $545,000 | 3/2 | 1,429 | $381 |
| Average | 4 comps | $584,725 | $371 |
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 $50,000 (7.9%) from the original list price.
| Jun 12, 2026 | Sold | $580,000 |
| Apr 6, 2026 | Price reducedfrom $615,000 | $599,000 |
| Feb 11, 2026 | Listed | $630,000 |
The good, the trade-offs & the location
- Built 2016 — post-2002 Florida wind codes (typically lower insurance)
- Storm protection: Impact Windows/Doors, Shutters
- 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.