Harbourside Drive, Longboat Key, FL

Everything we know about Harbourside Drive in Longboat Key: what is for sale, what has sold, what the homes are like and which communities the street runs through — from the MLS record and county parcel data, refreshed nightly.

9 homes sit on Harbourside Drive in Longboat Key, FL (ZIP 34228), built 1984–1984, a typical 2,224 sq ft with 3 bedrooms. 44 are for sale right now from $189,000 to $1,995,000. 21 closed in the last 12 months at a median of $635,000. Homes that sold since 2023 went for a median $825,000.

For sale on Harbourside Drive now

2450 Harbourside Drive #244, home for sale on Harbourside Drive
$1,995,000
3 bd · 3.5 ba · 3,083 sq ft · built 1990
2450 Harbourside Drive #244
Listing courtesy of MICHAEL SAUNDERS & COMPANY
2450 Harbourside Drive #234, home for sale on Harbourside Drive
$1,800,000
3 bd · 3 ba · 3,383 sq ft · built 1990
2450 Harbourside Drive #234
Listing courtesy of MICHAEL SAUNDERS & COMPANY
1916 Harbourside Drive #804, home for sale on Harbourside Drive
$1,599,000
4 bd · 3 ba · 2,846 sq ft · built 1982
1916 Harbourside Drive #804
Listing courtesy of MICHAEL SAUNDERS & COMPANY
2141 Harbourside Drive #1203, home for sale on Harbourside Drive
$1,450,000
3 bd · 2.5 ba · 2,204 sq ft · built 1984
2141 Harbourside Drive #1203
Listing courtesy of PREMIER SOTHEBY'S INTERNATIONAL REALTY
2550 Harbourside Drive #334, home for sale on Harbourside Drive
$1,400,000
3 bd · 3 ba · 3,083 sq ft · built 1990
2550 Harbourside Drive #334
Listing courtesy of COLDWELL BANKER REALTY
2550 Harbourside Drive #333, home for sale on Harbourside Drive
$1,395,000
3 bd · 2.5 ba · 3,067 sq ft · built 1990
2550 Harbourside Drive #333
Listing courtesy of INVESTMENTS IN SARASOTA
1906 Harbourside Drive #303, home for sale on Harbourside Drive
$799,000
2 bd · 2.5 ba · 1,590 sq ft · built 1982
1906 Harbourside Drive #303
Listing courtesy of COLDWELL BANKER REALTY
2020 Harbourside Drive #442, home for sale on Harbourside Drive
$699,000
2 bd · 2 ba · 1,192 sq ft · built 1984
2020 Harbourside Drive #442
Listing courtesy of MICHAEL SAUNDERS & COMPANY
1920 Harbourside Drive #1003, home for sale on Harbourside Drive
$624,900
2 bd · 2.5 ba · 1,690 sq ft · built 1982
1920 Harbourside Drive #1003
Listing courtesy of COLDWELL BANKER REALTY
2600 Harbourside Drive #O-13/14, home for sale on Harbourside Drive
$600,000
2600 Harbourside Drive #O-13/14
Listing courtesy of LBRE LLC
2600 Harbourside Drive #B-16, home for sale on Harbourside Drive
$500,000
· built 1985
2600 Harbourside Drive #B-16
Listing courtesy of LBRE LLC
2600 Harbourside Drive #C13, home for sale on Harbourside Drive
$489,500
2600 Harbourside Drive #C13
Listing courtesy of FINE PROPERTIES
2600 Harbourside Drive #C11, home for sale on Harbourside Drive
$479,500
· built 1983
2600 Harbourside Drive #C11
Listing courtesy of MICHAEL SAUNDERS & COMPANY
2800 Harbourside Drive #D-16, home for sale on Harbourside Drive
$425,000
· built 1985
2800 Harbourside Drive #D-16
Listing courtesy of LBRE LLC
2600 Harbourside Drive #L-05, home for sale on Harbourside Drive
$425,000
· built 1985
2600 Harbourside Drive #L-05
Listing courtesy of LBRE LLC
2600 Harbourside Drive #L-11, home for sale on Harbourside Drive
$425,000
· built 1985
2600 Harbourside Drive #L-11
Listing courtesy of LBRE LLC
2600 Harbourside Dr #B-06, home for sale on Harbourside Drive
$425,000
· built 1985
2600 Harbourside Dr #B-06
Listing courtesy of LBRE LLC
2600 Harbourside Dr #B-08, home for sale on Harbourside Drive
$425,000
2600 Harbourside Dr #B-08
Listing courtesy of LBRE LLC
2600 Harbourside Drive #R-13, home for sale on Harbourside Drive
$400,000
· built 1985
2600 Harbourside Drive #R-13
Listing courtesy of LBRE LLC
2600 Harbourside Drive #R-07, home for sale on Harbourside Drive
$400,000
· built 1985
2600 Harbourside Drive #R-07
Listing courtesy of LBRE LLC
2600 Harbourside Drive #B-13, home for sale on Harbourside Drive
$400,000
2600 Harbourside Drive #B-13
Listing courtesy of LBRE LLC
2800 Harbourside Drive #E-21, home for sale on Harbourside Drive
$385,000
· built 1985
2800 Harbourside Drive #E-21
Listing courtesy of LBRE LLC
2600 Harbourside Drive #J-09, home for sale on Harbourside Drive
$380,000
· built 1985
2600 Harbourside Drive #J-09
Listing courtesy of LBRE LLC
2600 Harbourside Drive #L-03, home for sale on Harbourside Drive
$375,000
· built 1985
2600 Harbourside Drive #L-03
Listing courtesy of LBRE LLC

Recent sales on Harbourside Drive

AddressSoldClosedBeds / bathsSq ft
2600 Harbourside Drive #I-09$275,0002026-09-30— / ——
2600 Harbourside Drive #N-05$210,0002026-09-29— / ——
1918 Harbourside Drive #902$1,235,0002026-07-172 / 2.51,748
2110 Harbourside Drive #536$725,0002026-06-263 / 2.02,031
1930 Harbourside Drive #145$515,0002026-06-032 / 2.01,270
1932 Harbourside Drive #254$530,0002026-06-032 / 2.01,192
1904 Harbourside Drive #204$850,0002026-05-283 / 3.02,135
1912 Harbourside Drive #602$496,5002026-05-222 / 2.51,590
2120 Harbourside Drive #628$1,650,0002026-05-043 / 3.02,616
1916 Harbourside Drive #803$642,0002026-04-162 / 2.51,626
1932 Harbourside Drive #217$590,0002026-04-062 / 2.01,442
2600 Harbourside Drive #N10$180,0002026-03-18— / ——
2120 Harbourside Drive #612$655,0002026-03-063 / 2.02,039
1928 Harbourside Drive #1403$635,0002026-03-022 / 2.51,590
1904 Harbourside Drive #202$419,5002026-02-272 / 2.51,590
2110 Harbourside Drive #558$1,100,0002026-02-172 / 2.52,550
1904 Harbourside Drive #201$815,0002026-02-123 / 3.02,135
2120 Harbourside Drive #617$740,0002026-01-153 / 2.02,039
1930 Harbourside Drive #136$605,0002025-12-302 / 2.01,270
2110 Harbourside Drive #522$715,0002025-12-183 / 2.02,039
1930 Harbourside Drive #142$470,0002025-10-242 / 2.01,192

The homes on Harbourside Drive

Built by decade: 1980s 9.

Last recorded sales (parcel record)

AddressSoldDateBuiltSq ft
2203 Harbourside Drive$725,0002025-05-3019842,352
2211 Harbourside Drive$1,036,1002024-05-1719842,219
2233 Harbourside Drive Unit 203$825,0002023-07-1119842,224
2161 Harbourside Drive$475,0002014-11-2119842,224
2159 Harbourside Drive$501,0002010-02-2619842,219
2020 Harbourside Dr Unit 424 425$540,0002009-11-0219842,462
2213 Harbourside Drive$645,0002006-08-3119842,224
2245 Harbourside Drive$670,0002006-04-2419842,219
2223 Harbourside Drive$545,0002005-04-2519842,224

Communities along Harbourside Drive

How to read this

Home counts, build years, sizes and last sales come from the county parcel record joined to MLS history; listings and 12-month closings from the live MLS feeds as of October 14, 2026. Listings appear courtesy of the listing brokerage under IDX rules; information deemed reliable but not guaranteed. See also all 237 homes for sale in Longboat Key, homes for sale in 34228.

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Common questions

How many homes are on Harbourside Drive in Longboat Key?

9 homes in the parcel and MLS record, built between 1984 and 1984.

Are there homes for sale on Harbourside Drive?

44 listed right now, from $189,000.

What do homes on Harbourside Drive sell for?

The median closing over the last 12 months was $635,000.