14865 Captiva Dr
Captiva, FL 33924
4 Beds
4 Baths
2,964 sqft
4 Beds
4 Baths
2,964 sqft
Local Information
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Description
Happy Daze is a beautiful 4-bedroom, 4-bath home set amidst tropical vegetation in Captiva's fun & quaint "village." Offering a multitude of options to enjoy all that Captiva has to offer, it's a short distance from a host of fun destinations. Close to the world-renown beaches for a day in the surf, listen to live music in one of the many outdoor dining venues, splash a paddleboard into the Gulf, or take a golf cart on a scenic tour, the fun times are as endless as the stars in the warm night sky. This inviting home offers stunning wood floors throughout, an open kitchen great for entertaining, soaring ceilings & a fireplace in the living room, and an enclosed den/office that doubles as an extra sleeping space. The lanai overlooks the private pool & spa framed by the lush greenery. For outdoor entertaining, there's a ping pong table, pool table & covered seating. Whether you are making the islands your home or earning great income through vacation rentals, this is the ideal Captiva retreat.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.
Home Highlights
Parking
Garage
Outdoor
Porch, Patio, Deck, Pool
View
No Info
HOA
None
Price/Sqft
No Info
Listed
No Info
Home Details for 14865 Captiva Dr
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Heating & Cooling Heating: Forced Air, ElectricAir ConditioningCooling System: CentralHeating Fuel: Forced Air |
Levels, Entrance, & Accessibility Stories: 3Floors: Tile, Hardwood |
Interior Details Number of Rooms: 8Types of Rooms: Dining RoomCeiling Fan |
Appliances & Utilities DishwasherDryerMicrowaveRefrigeratorWasher |
Fireplace & Spa FireplaceHot Tub or Spa |
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Exterior Home Features Roof: MetalDeckExterior: Vinyl, Wood, MetalPatioPorchSprinkler System |
Pool Pool |
Parking & Garage GarageParking Spaces: 2Parking: Garage Attached |
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Year Built Year Built: 2001Year Updated: 2001 |
Property Type / Style Property Type: Single Family HomeArchitecture: Colonial |
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Furnished |
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Units in Building: 1 |
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Lot Area: 7710 sqft |
Price History for 14865 Captiva Dr
| Date | Price | Event | Source |
|---|---|---|---|
| 11/29/2021 | $1,450,000 | Sold | Florida Gulf Coast MLS #221001593 |
| 09/29/2021 | $1,699,000 | Pending | Florida Gulf Coast MLS #221001593 |
| 01/08/2021 | $1,699,000 | Listed For Sale | Florida Gulf Coast MLS #221001593 |
| 01/01/2021 | ListingRemoved | Local MLS | |
| 06/12/2019 | $1,699,000 | Listed For Sale | Agent Provided |
| 10/22/2018 | $1,699,000 | ListingRemoved | Agent Provided |
| 06/29/2018 | $1,699,000 | Listed For Sale | Agent Provided |
| 02/25/2008 | $2,000,000 | ListingRemoved | N/A |
| 03/26/2007 | $2,000,000 | Listed For Sale | N/A |
| 05/28/2004 | $1,415,000 | Sold | N/A |
| 10/17/2000 | $400,000 | Sold | N/A |
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Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $21,871 |
| Assessment | $1,605,432 |
Home facts updated by county records
Comparable Sales for 14865 Captiva Dr
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.21 | Single-Family Home | $2,512,000 | 07/22/25 | 4 | 4 | 3,418 | |
0.25 | Single-Family Home | $2,900,000 | 08/07/25 | 4 | 4 | 2,622 | |
0.33 | Single-Family Home | $2,300,000 | 06/09/25 | 4 | 4 | 2,080 | |
0.11 | Single-Family Home | $1,200,000 | 03/18/26 | 3 | 3 | 1,126 | |
0.25 | Single-Family Home | $1,337,500 | 11/21/25 | 3 | 2 | 2,138 | |
0.22 | Single-Family Home | $638,600 | 04/21/26 | 5 | 5.5 | 3,555 | |
0.26 | Single-Family Home | $1,450,000 | 04/16/26 | 2 | 2 | 2,218 | |
0.27 | Single-Family Home | $1,286,000 | 11/06/25 | 3 | 2 | 1,622 | |
0.23 | Single-Family Home | $1,255,000 | 08/01/25 | 2 | 2 | 1,633 | |
0.04 | Single-Family Home | $1,050,000 | 03/06/26 | 2 | 2 | 1,176 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.
FOR SALETimothy Drobnyk, Premier Sotheby's Int'l Realty
FOR SALEOPEN THU, 10-1PMPhaidra A McDermott, Kingfisher Real Estate Inc.
FOR SALE
3D VIEWSue Plein, Kingfisher Real Estate Inc.
FOR SALE3D VIEWLeane T Suarez, John R. Wood Properties
FOR SALE3D VIEWBabs Maughan, John R. Wood Properties
FOR SALE3D VIEWKaren Bell, Michael Saunders & Company
FOR SALEMary Ann Cowart, Royal Shell Real Estate, Inc.
FOR SALE3D VIEWKaren Bell, Michael Saunders & Company
FOR SALE0.47 ACRESStephanie Bissett, Premier Sotheby's Int'l Realty
Assigned Schools
These are the assigned schools for 14865 Captiva Dr.
- Fort Myers High School
- 9-12
- Public
- 1760 Students
5/10GreatSchools 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
9/10GreatSchools 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 AverageThe staff exploits the total lack of accountability. Administration targets students and families as retaliation for complaints. Under leadership of the previous principal the school received a grade A for 5 out of 7 years. With the current principal at the reigns, the school has never received an A, yet they are the 2nd highest paid principal in the district. This principal takes liberties that are not within her authority, yet the district provides no accountability. While the administration is terrible at this school, it is a product of the school board and district's example of zero accountability. Consequences for noncompliance with policies only exist for students and parents.Parent Review2y ago - Estero High School
- 9-12
- Public
- 1581 Students
4/10GreatSchools RatingParent Rating AverageGreat school with great teachers and administrators.Parent Review1y 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
3/10GreatSchools RatingParent Rating Average
No reviews available for this school. 
Check out schools near 14865 Captiva 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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Apartments for Rent
APPLY INSTANTLYFURNISHED
See more homes for rent inCaptiva
Homes for sale near 14865 Captiva Dr
- Karen Bell, Michael Saunders & Company
- Babs Maughan, John R. Wood Properties
- Karen Bell, Michael Saunders & Company
0.26 ACRESLeane T Suarez, John R. Wood Properties
Babs Maughan, John R. Wood Properties
0.34 ACRESPhaidra A McDermott, Kingfisher Real Estate Inc.
NEW CONSTRUCTION0.58 ACRESTracy A Walters, Royal Shell Real Estate, Inc.- OPEN THU, 10-1PMPhaidra A McDermott, Kingfisher Real Estate Inc.
Alan Garcia, American Realty Of Captiva
See more homes for sale inCaptiva
Off Market Homes Near 14865 Captiva Dr
SOLDMAY 21, 2026Kingfisher Real Estate, Inc.
SOLDMAY 21, 2026Phaidra A McDermott, Kingfisher Real Estate Inc.
SOLDMAY 12, 2026Babs Maughan, John R. Wood Properties
SOLDAPR 29, 2026Jennifer McSorley, Pfeifer Realty Group LLC
SOLDAPR 21, 2026Babs Maughan, John R. Wood Properties
SOLDAPR 21, 2026Kelsey Smith, Kingfisher Real Estate Inc.
SOLDAPR 16, 2026Mary Ann Cowart, Royal Shell Real Estate, Inc.
SOLDAPR 2, 2026Babs Maughan, John R. Wood Properties
SOLDAPR 1, 2026Pfeifer Realty Group LLC- See more homes for sale inCaptiva
Homes for rent near 14865 Captiva Dr
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14865 Captiva Dr, Captiva, FL 33924 is a 4 bedroom, 2,964 sqft single-family home built in 2001. This property is not currently available for sale. 14865 Captiva Dr was last sold on Nov 29, 2021 for $1,450,000. The current Trulia Estimate for 14865 Captiva Dr is $1,961,800.