Discover effortless luxury in this lovely villa—your private oasis in a premier gated Naples community, Winding Cypress. This inviting 2-bedroom + den, 2-bath home delivers exceptional comfort and versatility with a bright, open layout designed for effortless living and entertaining. Step into the expansive Great Room with high ceilings, creating an open, airy vibe—perfect for gathering with friends or unwinding after a day out in Naples. The chef's kitchen impresses with premium quartz countertops, solid wood soft-close cabinets, and natural gas cooking. High-traffic porcelain tile flooring flows seamlessly throughout the entire villa, paired with smooth-finish walls for a clean, modern, low-maintenance aesthetic. The flexible den, enclosed by beautiful glass panel doors, adapts effortlessly as a home office or third bedroom. Both bedrooms feature generous walk-in closets, and the bathrooms showcase floor-to-ceiling porcelain tile, glass showers, and spa-like sophistication. The master bath elevates your routine with a dramatic full-wall custom mirror and elegant drop-down designer lighting. Outside, this premium lot offers generous spacing between villas and captivating views over the community's second-largest lake—where serene water vistas create an unparalleled sense of tranquility and timeless appeal. The west-facing orientation captures breathtaking sunsets reflecting off the shimmering waters, while the south-facing exposure floods the interior with natural light. Plenty of space awaits an extended lanai or private pool, all enhanced by the soothing backdrop of the lake. Built for peace of mind: impact windows and doors boost energy efficiency, reduce noise, and lower insurance premiums—no flood insurance required in FEMA Zone X. Appliances, A/C, and water heater have performed flawlessly since new. Fiber optic connectivity ensures ultra-fast internet and seamless 4K streaming. Natural gas powers cooking, drying, hot water, and preps for a whole-home generator. Nestled in gated Winding Cypress—praised as Naples' best lifestyle value with remarkably low HOA fees that cover comprehensive maintenance (lawn care, irrigation, community upkeep) plus full access to extensive high-end amenities—you'll embrace the pet-friendly lifestyle with two dedicated dog parks, miles of scenic walking/biking trails across 800+ acres of preserved natural land, and a vibrant social calendar with events curated by the on-site activities director. Resort-style perks include the on-site Shady Palm Café for casual dining and drinks, state-of-the-art fitness center with movement/yoga room, sparkling resort pool and spa, lighted tennis and pickleball courts, bocce courts, community garden, fire pit, and more—all accessible by foot, bike, or golf cart. Conveniently located between downtown Naples and Marco Island, you're minutes from pristine beaches, upscale shopping, and fine dining. Paradise is calling.
Pending
$585,000
7733 Jacaranda LN, NAPLES, FL 34114
2beds
1,554sqft
Single Family Residence
Built in 2018
5,227 Square Feet Lot
$-- Zestimate®
$376/sqft
$521/mo HOA
What's special
Elegant drop-down designer lightingNatural gas cookingSolid wood soft-close cabinetsSpa-like sophisticationGlass showers
- 140 days |
- 21 |
- 0 |
Zillow last checked:
Listing updated:
Listed by:
Jeffrey Waldman, PA 239-537-3334,
Premiere Plus Realty Company
Source: SWFLMLS,MLS#: 226006913
Originating MLS: Naples
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 2
- Bathrooms: 2
- Full bathrooms: 2
Rooms
- Room types: Den - Study, Great Room, Guest Bath, Screened Lanai/Porch, 2 Bedrooms Plus Den
Primary bedroom
- Dimensions: 16 x 12
Bedroom
- Dimensions: 14 x 10
Den
- Dimensions: 11 x 10
Dining room
- Dimensions: 12 x 14
Garage
- Dimensions: 21 x 19
Kitchen
- Dimensions: 9 x 11
Other
- Dimensions: 11 x 14
Living room
- Dimensions: 17 x 14
Heating
- Central
Cooling
- Central Air
Appliances
- Included: Dishwasher, Disposal, Dryer, Microwave, Range, Refrigerator/Freezer, Refrigerator/Icemaker, Self Cleaning Oven, Washer
- Laundry: Inside
Features
- Built-In Cabinets, Custom Mirrors, French Doors, Pantry, Smoke Detectors, Walk-In Closet(s), Window Coverings, Den - Study, Great Room, Guest Bath, Laundry in Residence, Screened Lanai/Porch
- Flooring: Tile
- Doors: French Doors, Impact Resistant Doors
- Windows: Window Coverings, Impact Resistant Windows
- Has fireplace: No
Interior area
- Total structure area: 1,914
- Total interior livable area: 1,554 sqft
Property
Parking
- Total spaces: 2
- Parking features: Driveway, Attached
- Attached garage spaces: 2
- Has uncovered spaces: Yes
Features
- Stories: 1
- Patio & porch: Patio, Screened Lanai/Porch
- Pool features: Community
- Spa features: Community
- Has view: Yes
- View description: Lake
- Has water view: Yes
- Water view: Lake
- Waterfront features: Lake
- Frontage type: Lakefront
Lot
- Size: 5,227 Square Feet
- Features: Irregular Lot, Oversize
Details
- Additional structures: Tennis Court(s)
- Parcel number: 82679017840
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: 2018
Utilities & green energy
- Gas: Natural
- Water: Central
Community & HOA
Community
- Features: Clubhouse, Pool, Dog Park, Fitness Center, Restaurant, Sidewalks, Street Lights, Tennis Court(s), Gated
- Security: Smoke Detector(s), Gated Community
- Subdivision: WINDING CYPRESS
HOA
- Has HOA: Yes
- Amenities included: Bocce Court, Clubhouse, Pool, Community Room, Spa/Hot Tub, Dog Park, Fitness Center, Internet Access, Library, Pickleball, Private Membership, Restaurant, Sidewalk, Streetlight, Tennis Court(s), Underground Utility
- HOA fee: $6,248 annually
Location
- Region: Naples
Financial & listing details
- Price per square foot: $376/sqft
- Tax assessed value: $477,902
- Annual tax amount: $4,607
- Date on market: 2/14/2026
- Lease term: Buyer Finance/Cash
Estimated market value
Not available
Estimated sales range
Not available
Not available
Price history
| Date | Event | Price |
|---|---|---|
| 5/26/2026 | Pending sale | $585,000$376/sqft |
Source: | ||
| 3/28/2026 | Price change | $585,000-2.5%$376/sqft |
Source: | ||
| 2/14/2026 | Listed for sale | $599,999+332.5%$386/sqft |
Source: | ||
| 9/30/2020 | Sold | $138,725-61.8%$89/sqft |
Source: Public Record Report a problem | ||
| 2/8/2018 | Sold | $363,075$234/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $4,800 +4.5% | $315,750 +2.9% |
| 2024 | $4,594 +72.5% | $306,851 +3% |
| 2023 | $2,664 -2.6% | $297,914 +3% |
| 2022 | $2,734 -0.8% | $289,237 +3% |
| 2021 | $2,758 +2.5% | $280,813 +1.4% |
| 2020 | $2,692 +1.9% | $276,936 +2.3% |
| 2019 | $2,641 +137.6% | $270,710 +176.9% |
| 2018 | $1,112 -52.2% | $97,769 +404.5% |
| 2017 | $2,325 | $19,378 |
Find assessor info on the county website
Monthly payment
Est. payment$--/mo
Payment breakdown
Explore the cost of this home by adjusting the details. Changes won't be saved.All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
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Climate risks
Neighborhood: Winding Cypress
Nearby schools
GreatSchools rating
- 7/10Lely Elementary SchoolGrades: PK-5Distance: 3.4 mi
- 7/10Manatee Middle SchoolGrades: 6-8Distance: 1 mi
- 5/10Lely High SchoolGrades: 9-12Distance: 3.5 mi
A local agent can set up tours, give advice and negotiate with sellers.
A local lender can help you make sure your offer is ready when you are.
- Florida
- Collier County
- Naples
- 34114
- Winding Cypress
- 7733 Jacaranda LN






