4440 Smugglers Dr
Captiva, FL 33924
3 Beds
2 Baths
1,296 sqft
3 Beds
2 Baths
1,296 sqft
Local Information
- Map ViewExplore the area around 4440 Smugglers Dr.
- Schools1 Preschool School1 Elementary School1 Middle School6 High Schools
- Shop & Eat
-- mins to
Home Highlights
Property Type
Single-Family Home
Year Built
1985
Living Area
1,296 sqft
Price/Sqft
$612
Parking
Open Parking
HOA
None
About this House
FANTASTIC North Captiva Island Opportunity! Prime Rental Opportunity! Welcome to Your Own Private Island Oasis, Great Island Location, Peaceful, One Story, Heated Pool Home surrounded by a Mature Lush and Tropical Landscape. Great Short Term Vacation Rental Property with Upcoming Bookings in Place. Optimal Mid Island Location with Very Short Walk or Golf Cart Ride to the Beach or to the Island Club at North Captiva and all it has to offer! Lovely Island Full Time Residence, Perfect Island Vacation Rental or Combination! Prime Busy and Operating Short Term Vacation Rental. Vibrant Eclectic Kitchen with All Appliances in Place, Plenty of Countertop and Cabinet Space. Large Front Open Balcony and Outdoor Space for Entertaining and Enjoyment. Multiple Sets of French Doors to bring the Outdoors In! Vaulted Bright Main Living and Dining Area. Vaulted Main Bedroom with French Doors to the Open Balcony. SQ Footage includes 860 SQ FT+ in the Upper Living Area consisting of 2 Bedrooms (1 King and 1 Bunk Room with 2 Twins and a Full) and 2 Full Baths with Showers. Additional Finished Lower Level of 432 SQ FT+ with 1 Queen Bedroom with French Doors Out to the Inground Pool, 1 Half Bath, Inside Laundry, and a Large Owners Bonus Room, Storage Room, or another Guest Bedroom! Inside Laundry Closet offers Full Size Washer and Dryer. Private Well and Septic not shared. Being Sold Turnkey Furnished! Nestled Among the Palm Trees "Smugglers Hideaway" is an Island Home that you will want to consider! Fantastic Rental History and Consistent Regular Visits by Owner. Bring Your Offers!
4440 Smugglers Dr, Captiva, FL 33924 is a 3 bedroom, 2 bathroom, 1,296 sqft single-family home built in 1985. It last sold for $805,000 on Nov 15, 2024 (10% below the $895,000 asking price). It is currently off market. The Trulia Estimate is $792,700, with a rent estimate of $6,475/month.
Home Details for 4440 Smugglers Dr
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MLS Status: Closed |
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Beds & Baths Number of Bedrooms: 3Number of Bathrooms: 2Number of Bathrooms (full): 2 |
Dimensions and Layout Living Area: 1296 Square Feet |
Appliances & Utilities Utilities: Cable Available, High Speed Internet AvailableAppliances: Dryer, Dishwasher, Ice Maker, Microwave, Range, Refrigerator, RefrigeratorWithIce Maker, WasherDishwasherDryerLaundry: Washer Hookup,Dryer Hookup,InsideMicrowaveRefrigeratorWasher |
Heating & Cooling Heating: Central,ElectricHas CoolingAir Conditioning: Central Air,Ceiling Fan(s),ElectricHas HeatingHeating Fuel: Central |
Fireplace & Spa No Spa |
Windows, Doors, Floors & Walls Window: Other, Window CoveringsDoor: French DoorsFlooring: Laminate, Tile |
Levels, Entrance, & Accessibility Number of Stories: 1Floors: Laminate, Tile |
View Has a ViewView: Landscaped, Pool |
Room & Shared Space Shared space is furnished |
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Exterior Home Features Roof: ShinglePatio / Porch: Balcony, Deck, Open, PorchExterior: Deck, None, Outdoor ShowerFoundation: Pillar/Post/PierHas a Private Pool |
Parking & Garage Number of Carport Spaces: 1Number of Covered Spaces: 1Has a CarportNo GarageHas Open ParkingParking Spaces: 1Parking: Driveway,Unpaved,Attached Carport |
Pool Pool: Fiberglass, Electric Heat, Heated, In Ground, Outside Bath AccessPool |
Frontage Waterfront: NoneRoad Surface Type: UnimprovedNot on Waterfront |
Water & Sewer Sewer: Septic Tank |
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Cumulative Days on Market: 224 |
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Year Built Year Built: 1985 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Other,Stilt |
Building Construction Materials: Other, Wood Siding, Wood Frame |
Property Information Condition: ResaleParcel Number: 0545211700002.0330 |
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Price List Price: $895,000 |
Status Change & Dates Off Market Date: Fri Nov 15 2024Possession Timing: Close Of Escrow |
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Direction & Address City: Upper CaptivaCommunity: CASTAWAY KEY |
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Building Area Building Area: 3251 Square Feet |
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Community Features: Non-GatedUnits in Building: 1 |
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HOA Fee Includes: NoneAssociation for this Listing: Florida Gulf CoastNo HOA |
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Lot Area: 9374.112 sqft |
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Listing Terms: All Financing Considered, Cash |
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Business Information Ownership: Single Family |
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Furnished |
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Mls Number: 224031216Living Area Range Units: Square FeetAbove Grade Unfinished Area Units: Square FeetBelow Grade Unfinished Area Units: Square FeetUniversal Property Id: US-12071-N-05452117000020330-R-N |
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HOA Amenities: Other,Management |
Last check for updates: about 1 hour ago
Listed by Amy Ivey, (239) 462-9614
Swept Away Realty
Bought with: Christine Maier, (239) 410-9233, RE/MAX Trend
Originating MLS: Florida Gulf Coast
Source: Florida Gulf Coast MLS, MLS#224031216
Price History for 4440 Smugglers Dr
| Date | Price | Event | Source |
|---|---|---|---|
| 11/15/2024 | $805,000 | Sold | Florida Gulf Coast MLS #224031216 |
| 10/24/2024 | $895,000 | Pending | SWFLMLS #224031216 |
| 09/05/2024 | $895,000 | PriceChange | SWFLMLS #224031216 |
| 06/29/2024 | $929,000 | PriceChange | SWFLMLS #224031216 |
| 04/05/2024 | $989,000 | Listed For Sale | SWFLMLS #224031216 |
| 12/29/2016 | $315,000 | Sold | Florida Gulf Coast MLS #216062347 |
| 10/05/2016 | $339,000 | PriceChange | Agent Provided |
| 08/12/2016 | $355,000 | PriceChange | Agent Provided |
| 03/19/2016 | $365,000 | PriceChange | Agent Provided |
| 11/23/2015 | $399,000 | PriceChange | Agent Provided |
| 05/16/2015 | $425,000 | Listed For Sale | Agent Provided |
| 07/22/2014 | $425,000 | ListingRemoved | Agent Provided |
| 10/28/2013 | $425,000 | Listed For Sale | Agent Provided |
| 01/02/2013 | $188,000 | Sold | N/A |
| 12/22/2012 | $184,900 | Pending | Agent Provided |
| 11/07/2012 | $184,900 | Listed For Sale | Agent Provided |
| 06/01/2001 | $159,000 | Sold | N/A |
| 09/08/2000 | $160,000 | Sold | N/A |
| 09/04/1996 | $90,000 | Sold | N/A |
| 01/23/1995 | $45,000 | Sold | N/A |
Market trends in Captiva
Last updated June 2026
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
94
7MoM
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Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $11,623 |
| Assessment | $791,075 |
Home facts updated by county records
Comparable Sales for 4440 Smugglers Dr
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.20 | Single-Family Home | $905,000 | 12/08/25 | 3 | 2 | 1,522 | |
0.19 | Single-Family Home | $1,254,500 | 04/30/26 | 3 | 3 | 1,601 | |
0.04 | Single-Family Home | $1,350,000 | 09/26/25 | 4 | 3 | 2,358 | |
0.40 | Single-Family Home | $1,300,000 | 04/03/26 | 3 | 2 | 1,584 | |
0.08 | Single-Family Home | $1,381,500 | 07/13/26 | 3 | 4 | 1,920 | |
0.39 | Single-Family Home | $653,000 | 07/14/26 | 2 | 2 | 936 | |
0.55 | Single-Family Home | $692,000 | 05/13/26 | 2 | 2 | 1,038 | |
0.27 | Single-Family Home | $1,430,000 | 01/06/26 | 3 | 3 | 2,211 | |
0.49 | Single-Family Home | $945,000 | 03/27/26 | 3 | 3 | 2,072 | |
0.15 | Single-Family Home | $892,000 | 07/17/26 | 6 | 3.5 | 2,021 |
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Assigned Schools
These are the assigned schools for 4440 Smugglers Dr.
- Fort Myers High School
- 9-12
- Public
- 1760 Students
6/10GreatSchools RatingParent Rating AverageIf your child is not part of the I.B program forget about it . That’s all they care about . They have duel enrollment which allows students to graduate with h.s diploma and get AA degree but the school could care less about those students. 2025 graduation ceremony didn’t have one thing listed about duel enrollment .Parent Review1y ago - The Sanibel School
- PK-8
- Public
- 213 Students
10/10GreatSchools RatingParent Rating AverageThe Sanibel School is truly a gem where students thrive academically, creatively, and personally. The school fosters an environment of excellence, supported by a dedicated team of educators who go above and beyond to ensure every child succeeds. From the innovative STEAM programs to their exceptional environmental education initiatives, students are engaged in hands-on, meaningful learning experiences that prepare them for the future. What sets Sanibel School apart is the incredible community and parent support. Families are deeply involved, collaborating with teachers to enhance the learning environment. Local organizations, like Ding Darling, SCCF, Sanibel Sea School, and CROW partner with the school, enriching students' experiences and providing unique opportunities beyond the classroom. The connection between the school and the Sanibel community creates a nurturing and dynamic atmosphere where students are empowered to grow into confident, curious, and responsible individuals.Sanibel School is more than just a place of learning; it’s a community hub that values education, creativity, and environmental stewardship. The school’s commitment to student success and the overwhelming support from parents and the local community make it an exemplary educational institution.Parent Review1y ago - Cypress Lake High School
- 9-12
- Public
- 1328 Students
5/10GreatSchools RatingParent Rating AverageGreat school when I attended. Administration could’ve been better but overall great school. Hope it’s still exceptionalOther Review3w ago - Estero High School
- 9-12
- Public
- 1581 Students
4/10GreatSchools RatingParent Rating AverageGreat school with great teachers and administrators.Parent Review2y ago - South Fort Myers High School
- 9-12
- Public
- 1619 Students
2/10GreatSchools RatingParent Rating AverageI think it is a very good school, they keep the student busy in all areas. Teacher have very good values, and they are very good example to the student. I had kids there, my older one just graduated and the other one is in 10 Grade.Parent Review11y ago - Dunbar High School
- 9-12
- Public
- 1695 Students
2/10GreatSchools RatingParent Rating AverageThe principal plays favorites with his employees. For instance, one, long time, hard working employee can be entirely overlooked and placed in new position to be replaced by a less educated and older choice from the principal. When the principal and/or school board members fail their best and brightest younger teachers, it's the students who will untimely fail.Other Review2y ago - Bonita Springs High School
- 9-12
- Public
- 1475 Students
4/10GreatSchools RatingParent Rating Average
No reviews available for this school. 
Check out schools near 4440 Smugglers Dr.
What Locals Say about Captiva
At least 3 Trulia users voted on each feature.
100 % Say people would walk alone at night
89 % Say it's walkable to restaurants
82 % Say there's wildlife
78 % Say parking is easy
75 % Say it's quiet
69 % Say it's dog friendly
67 % Say they plan to stay for at least 5 years
67 % Say car is needed
56 % Say there's holiday spirit
50 % Say streets are well-lit
50 % Say kids play outside
43 % Say yards are well-kept
38 % Say it's walkable to grocery stores
25 % Say there are sidewalks
20 % Say neighbors are friendly
14 % Say there are community events
Sourced by Trulia users. Learn more about our methodology.
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