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Property Description
Under construction and designed for the ultimate boating lifestyle, this exceptional 5- bedroom, 7-bath residence is ideally positioned on a deep water canal in the highly desirable Longboat Key Estates community. Offering over 4,500 square feet of refined, resort-style living, the home is built to latest hurricane building standards with solid block construction and hurricane-impact windows and doors. Seamlessly blending indoor and outdoor living, the southwest-facing canal-front pool captures breathtaking views stretching across Sarasota Bay to the Gulf of Mexico. An elevated lanai with intricate ceiling details features a fully equipped outdoor kitchen-perfect for entertaining while enjoying spectacular sunset skies. Boating enthusiasts will appreciate the brand-new seawall and direct access to the bay, making it effortless to explore the surrounding waters. The beach is just a short stroll away, adding to the home's appeal. There is also a private Tiki Hut on the beach for the association members and a fishing dock on the bay. With construction already underway, buyers have a unique opportunity to personalize final finishes and tailor the home to their vision. Conveniently located just a short drive from the upscale shopping and dining of St. Armands Circle, the vibrant arts and culture of Sarasota, and the world-renowned beaches of Longboat Key, this property offers the perfect blend of luxury, location, and lifestyle.
Full Property Details
Full Property Details for 530 Jessmyth Dr
General
- Price: $5,985,000
- HOA FEE: $375/month
- HOA FEE FREQ.: Annually
- Taxes: $14,092 (2025)
- Status: Active
- Type: Lots/Land
- Source: MidFloridaRegionalMLS
- MLS ID: A4691731
- Updated: 5/1/2026
- Added to Site: 4 day(s) ago
Location
- Area: 34228 - Longboat Key
- County: Sarasota
- Development Name: 34228 - Longboat Key
- Subdivision: LONGBOAT KEY ESTATES
- Driving Directions: North on Longboat Key drive, right on Royal, then left on Jesmyth
- Direction Faces: Northwest
Community
- Community Name: 34228 - Longboat Key
- Community Features: Dock, Beach Area
- Association: Yes
- Assoc. Name: SANDY SULLENBERGER
- Assoc. Fees Include: Private Road
Utilities
- Sewer: Public Sewer
- Water: Public
- Utility Description: Cable TV Available, Fire Hydrant, Phone Available, Sewer Connected, Water Connected
Structural Information
- Current Bldg. Use: Residential
Lot Features
- Lot Size (Acres): 0.28
- Lot Size (Sq. Ft.): 12,103
- Lot Size: 12103
- Lot Dimensions: 192 x 67
- Frontage: City Street
- Street/Road Desc.: Paved
Financial Considerations
- Price Per Acre: $21,375,000
- Association Fee: $4,500
- Assoc Fee Freq.: Annually
- Assoc Fee Desc.: Required
- Tax Amount: $14,092
- Tax Year: 2025
Disclosures and Reports
- Ownership: Fee Simple
- Special Conditions: None
- Legal Description: LOT 2 & W 1/2 OF LOT 3 DESC AS BEG AT SW COR OF LOT 3 TH ELY ALG WATERS EDGE 49.62 FT TH N-6- 49-W 114.83 FT TH S-58-05-W 54.8 FT TH S-6-49-E 91.5 FT TO POB BLK D LONGBOAT KEY ESTATES
- Flood Zone Info: AE
- APN: 2050017
- Property ID: 2050017
- Block/Lot/Section: D
Listed by Beach House Real Estate Llc
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Schools
Schools serving 530 Jessmyth Dr
School District:Sarasota County School District
| Name | Grades | Distance |
|---|---|---|
Southside Elementary School, Sarasota, FL 1901 Webber Street, Sarasota, FL 34239 | PK-5 | 8.5 mi |
Booker Middle School 2250 Myrtle Street, Sarasota, FL 34234 | 6-8 | 7.1 mi |
Booker High School 3201 North Orange Avenue, Sarasota, FL 34234 | 9-12 | 6.2 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 530 Jessmyth Dr
Date
Details
Price
Change
Source
5/01/2026
Listed
$5,985,000
470%
MLS
11/30/2021
Sold
$1,050,000
—
Public Record
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Tax History
Tax History for 530 Jessmyth Dr
Year
Property Taxes
Change
Tax Assessment
Change
2024
$14,442
—
$1,034,900
-2%
2024
$14,442
-5%
$1,057,100
-5%
2023
$15,282
48%
$1,113,700
36%
2021
$10,343
-28%
$819,200
-20%
2022
$14,286
38%
$1,021,200
97%
2021
$10,343
39%
$517,500
9%
2019
$7,462
-2%
$476,300
-1%
2018
$7,632
18%
$482,790
10%
2017
$6,488
4%
$438,900
6%
2016
$6,249
15%
$414,500
23%
2015
$5,415
17%
$335,940
10%
2014
$4,614
3%
$305,400
3%
2013
$4,463
—
$297,500
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 530 Jessmyth Dr
530 Jessmyth Drive, Longboat Key, FL 34228 (MLS# A4691731) is a Lots/Land property with a lot size of 0.28 acres. 530 Jessmyth Drive is currently listed for $5,985,000 and was received on May 01, 2026. Want to learn more about 530 Jessmyth Drive? Do you have questions about finding other Lots/Land real estate for sale in Longboat Key? You can browse all Longboat Key real estate or contact a Coldwell Banker agent to request more information.

