$809,900
- 3 Beds
- 2 Baths
- 1,296 sqft
4440 Smugglers Dr, Captiva, FL 33924
Est. Refi. Payment $5,326/mo*
Refinance Your HomeCurrently Off Market - Sold Nov 15, 2024 for $805,000
Home Value
Trulia Estimate
$810KSince last month
Increased$3K (+0.4%)Since last year
Increased$71K (+9.7%)Since last sale
Increased$5K (+0.6%)Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.
Trulia Estimate
The of this home's value increased by +141% in the last 10 years
| Month | Estimated value |
|---|---|
2026 | |
| September 2026 | $810K |
| August 2026 | $807K |
| July 2026 | $793K |
| June 2026 | $763K |
| May 2026 | $739K |
| April 2026 | $722K |
| March 2026 | $711K |
| February 2026 | $720K |
| January 2026 | $733K |
2025 | |
2024 | |
2023 | |
2022 | |
2021 | |
2020 | |
2019 | |
2018 | |
2017 | |
2016 | |
Comparable sales
These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.10 | Single-Family Home | $974,000 | 08/27/26 | 3 | 3.5 | 1,608 | |
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 | |
0.46 | Single-Family Home | $1,034,999 | 08/19/26 | 3 | 2 | 1,823 | |
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 | |
0.27 | 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 |
Nearby home prices
Get a sense of expected prices in the area by checking the value of nearby homes.Address | Distance | Price | Bed | Bath | Sqft | Status |
|---|---|---|---|---|---|---|
0.02 | - | - | - | - | Off Market | |
0.06 | $1,299,000 | 3 | 3.5 | 2,481 | For Sale | |
0.05 | - | - | - | - | Off Market | |
0.03 | $95,000 | - | - | - | Recently Sold | |
0.08 | $1,381,500 | 3 | 4 | 1,920 | Recently Sold | |
0.04 | $1,425,000 | 4 | 3 | 2,358 | For Sale | |
0.05 | $130,000 | - | - | - | For Sale | |
0.10 | $595,000 | - | - | - | For Sale | |
0.09 | - | - | - | - | Off Market | |
0.08 | $170,000 | - | - | - | For Sale | |
0.13 | $450,000 | - | - | - | For Sale |
Local Information
-- mins to
Home Highlights
Single-Family Home
Built in 1985
1,296 sqft
$625/sqft
Open Parking
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). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $809,900.
Last check for updates: about 4 hours 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

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 |
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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 |
Price and Tax history
| Date | Event | Price |
|---|---|---|
Nov 15, 2024 Source: Florida Gulf Coast MLS #224031216 | Sold | $805,000 |
Oct 24, 2024 Source: SWFLMLS #224031216 | Pending | $895,000 |
Sep 5, 2024 Source: SWFLMLS #224031216 | PriceChange | $895,000 Price decreased by 4% |
Jun 29, 2024 Source: SWFLMLS #224031216 | PriceChange | $929,000 Price decreased by 6% |
Apr 5, 2024 Source: SWFLMLS #224031216 | Listed For Sale | $989,000 |
Dec 29, 2016 Source: Florida Gulf Coast MLS #216062347 | Sold | $315,000 |
Oct 5, 2016 Source: Agent Provided | PriceChange | $339,000 Price decreased by 5% |
Aug 12, 2016 Source: Agent Provided | PriceChange | $355,000 Price decreased by 3% |
Mar 19, 2016 Source: Agent Provided | PriceChange | $365,000 Price decreased by 9% |
Nov 23, 2015 Source: Agent Provided | PriceChange | $399,000 Price decreased by 6% |
May 16, 2015 Source: Agent Provided | Listed For Sale | $425,000 |
Jul 22, 2014 Source: Agent Provided | ListingRemoved | $425,000 |
Oct 28, 2013 Source: Agent Provided | Listed For Sale | $425,000 |
Jan 2, 2013 Source: N/A | Sold | $188,000 |
Dec 22, 2012 Source: Agent Provided | Pending | $184,900 |
Nov 7, 2012 Source: Agent Provided | Listed For Sale | $184,900 |
Jun 1, 2001 Source: N/A | Sold | $159,000 |
Sep 8, 2000 Source: N/A | Sold | $160,000 |
Sep 4, 1996 Source: N/A | Sold | $90,000 |
Jan 23, 1995 Source: N/A | Sold | $45,000 |
| Year | Property tax | Tax assessment |
|---|---|---|
| 2025 | $11,623 | $791,075 |
Home facts updated by county records
Market trends in Captiva
Last updated August 2026
Avg. sale price
—
Sale-to-List Price
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Price per sq ft
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Available listings
85
Around this home
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.
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections

IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.
Frequently asked questions about 4440 Smugglers Dr
- What is 4440 Smugglers Dr estimated to be worth?Trulia's estimated value for 4440 Smugglers Dr in Captiva, FL is $809,900.
- What is the price history for 4440 Smugglers Dr?4440 Smugglers Dr in Captiva, FL last sold for $805,000 in November 2024.
- What are the closest schools to 4440 Smugglers Dr?The closest schools to 4440 Smugglers Dr in Captiva, FL are Bonita Springs High School (rated 4/10), Cypress Lake High School (rated 5/10), Dunbar High School (rated 2/10).
- Does 4440 Smugglers Dr have air conditioning?Yes, 4440 Smugglers Dr in Captiva, FL has air conditioning.
- Does 4440 Smugglers Dr have a pool?Yes, 4440 Smugglers Dr in Captiva, FL has a pool.
- Does 4440 Smugglers Dr have laundry facilities?Yes, 4440 Smugglers Dr in Captiva, FL has in-unit laundry.

