$1,450,000
4 Bed Pool Home for Sale in Upper Captiva
4490 Oyster Shell Drive, Upper Captiva, FL, 33924
About this home
High-performing, income-producing vacation rental on one of North Captiva Island's premier streets. Privately nestled among mature tropical landscaping, this beautifully maintained 4-bedroom, 3.5-bath island retreat offers over 2,300 sq ft of thoughtfully designed living space and a proven history of strong rental performance. Guests are drawn to the resort-style outdoor living, featuring an exceptionally large private pool, hot tub and outdoor shower, multiple entertaining areas, and a spectacular southwest-facing third-floor lanai that fully opens to the living room, creating a seamless indoor/outdoor living experience. Two en-suite bedrooms, a bunk room with a third bath, and a fourth queen suite provide ideal accommodations for owners and guests alike. Recent upgrades include Hardie Plank siding, two HVAC systems, Trex decking, a Brazilian hardwood pool deck, a cargo/luggage lift, and a paver driveway. A rare opportunity to own a turnkey island property that combines exceptional rental income, lush tropical privacy, premium outdoor amenities, and one of North Captiva's most desirable locations.
Property details
- Type
- SingleFamilyResidence
- Year built
- 2005
- Interior
- 2,262 sqft
- Lot size
- 8,842.68 sqft
- Acreage
- 0.20 acres
- Garage
- None
- Days on market
- 25
- Total association fees
- None
- CDD
- None
- Est. taxes (1.4%)
- $20,300/yr
- Flood zone (area est.)
- Not available
- Storm protection
- Impact Windows/Doors
- Exposure
- North
- Waterfront
- No
- Gulf access
- No
- Gulf access type
- N/A
- Pool
- Yes
- Spa
- Yes
- Natural gas
- No
- Water
- Well
- Sewer
- Septic Tank
- New construction
- No
- Pets
- Yes
- County
- Lee
Amenities
We rate a home against recently SOLD homes within ~1 mile that match on size, beds/baths, and age. This home doesn't have enough close comparables in the last 12 months for a reliable read, ask Rick for a personalized CMA.
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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 |
|---|---|---|---|---|---|
| 4460 Smugglers Drive | Sep 2025 | $1,350,000 | 4/3 | 2,358 | $573 |
| 551 Gulf Lane | Jan 2026 | $1,430,000 | 3/3 | 2,211 | $647 |
| Average | 2 comps | $1,390,000 | $610 |
Market trends, Upper Captiva
Live area medians from the MLS · see all listings. Indicative, not an appraisal.
Price & status history
Down $13,050,000 (90%) from the original list price.
| Aug 24, 2026 | Back on market | |
| Jul 20, 2026 | Price reducedfrom $14,500,000 | $1,450,000 |
| Jul 20, 2026 | Listed | $14,500,000 |
The good, the trade-offs & the location
- Built 2005 — post-2002 Florida wind codes (typically lower insurance)
- Private pool
- Storm protection: Impact Windows/Doors
- No garage listed
Straight-line distances to major SWFL amenities, approximate; actual drive times vary.
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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.