4440 Smugglers Dr, Captiva, FL 33924
Property image
Property image
OFF MARKET

$809,900

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 1,296 sqft

4440 Smugglers Dr, Captiva, FL 33924

Est. Refi. Payment $5,326/mo*
Refinance Your Home
Currently Off Market - Sold Nov 15, 2024 for $805,000

Home Value

Trulia Estimate
$810K
Since 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
MonthEstimated 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

  • Map ViewExplore the area around 4440 Smugglers Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School6 High Schools
  • Shop & Eat
-- mins to
Commute Destination

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 23 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

Active Status

MLS Status: Closed

Interior Features

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

Exterior Features

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

Days on Market

Cumulative Days on Market: 224

Property Information

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

Price & Status

Price
List Price: $895,000
Status Change & Dates
Off Market Date: Fri Nov 15 2024Possession Timing: Close Of Escrow

Location

Direction & Address
City: Upper CaptivaCommunity: CASTAWAY KEY

Building

Building Area
Building Area: 3251 Square Feet

Community

Community Features: Non-GatedUnits in Building: 1

HOA

HOA Fee Includes: NoneAssociation for this Listing: Florida Gulf CoastNo HOA

Lot Information

Lot Area: 9374.112 sqft

Offer

Listing Terms: All Financing Considered, Cash

Business

Business Information
Ownership: Single Family

Rental Terms, Policies & Fees

Furnished

Miscellaneous

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

Additional Information

HOA Amenities: Other,Management

Price and Tax history

DateEventPrice
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

Market trends in Captiva

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
Sale-to-List Price
Price per sq ft
Available listings
85

Around this home

The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

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

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.

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