Erin McGoldrick
← INNOVATE Real Estate
Condominium at 2101 HARBOURSIDE DR #1103, LONGBOAT KEY
Condominium at 2101 HARBOURSIDE DR #1103, LONGBOAT KEY, photo 2 of 65
Condominium at 2101 HARBOURSIDE DR #1103, LONGBOAT KEY, photo 3 of 65
Condominium at 2101 HARBOURSIDE DR #1103, LONGBOAT KEY, photo 4 of 65
Condominium at 2101 HARBOURSIDE DR #1103, LONGBOAT KEY, photo 5 of 65
Condominium at 2101 HARBOURSIDE DR #1103, LONGBOAT KEY, photo 6 of 65
Condominium at 2101 HARBOURSIDE DR #1103, LONGBOAT KEY, photo 7 of 65
Condominium at 2101 HARBOURSIDE DR #1103, LONGBOAT KEY, photo 8 of 65
Condominium at 2101 HARBOURSIDE DR #1103, LONGBOAT KEY, photo 9 of 65
Condominium at 2101 HARBOURSIDE DR #1103, LONGBOAT KEY, photo 10 of 65
Condominium at 2101 HARBOURSIDE DR #1103, LONGBOAT KEY, photo 11 of 65
Condominium at 2101 HARBOURSIDE DR #1103, LONGBOAT KEY, photo 12 of 65
Condominium at 2101 HARBOURSIDE DR #1103, LONGBOAT KEY, photo 13 of 65
Condominium at 2101 HARBOURSIDE DR #1103, LONGBOAT KEY, photo 14 of 65
Condominium at 2101 HARBOURSIDE DR #1103, LONGBOAT KEY, photo 15 of 65
Condominium at 2101 HARBOURSIDE DR #1103, LONGBOAT KEY, photo 16 of 65
Condominium at 2101 HARBOURSIDE DR #1103, LONGBOAT KEY, photo 17 of 65
Condominium at 2101 HARBOURSIDE DR #1103, LONGBOAT KEY, photo 18 of 65
Condominium at 2101 HARBOURSIDE DR #1103, LONGBOAT KEY, photo 19 of 65
Condominium at 2101 HARBOURSIDE DR #1103, LONGBOAT KEY, photo 20 of 65
Condominium at 2101 HARBOURSIDE DR #1103, LONGBOAT KEY, photo 21 of 65
Condominium at 2101 HARBOURSIDE DR #1103, LONGBOAT KEY, photo 22 of 65
Condominium at 2101 HARBOURSIDE DR #1103, LONGBOAT KEY, photo 23 of 65
Condominium at 2101 HARBOURSIDE DR #1103, LONGBOAT KEY, photo 24 of 65
Condominium at 2101 HARBOURSIDE DR #1103, LONGBOAT KEY, photo 25 of 65
Condominium at 2101 HARBOURSIDE DR #1103, LONGBOAT KEY, photo 26 of 65
Condominium at 2101 HARBOURSIDE DR #1103, LONGBOAT KEY, photo 27 of 65
Condominium at 2101 HARBOURSIDE DR #1103, LONGBOAT KEY, photo 28 of 65
Condominium at 2101 HARBOURSIDE DR #1103, LONGBOAT KEY, photo 29 of 65
Condominium at 2101 HARBOURSIDE DR #1103, LONGBOAT KEY, photo 30 of 65
Condominium at 2101 HARBOURSIDE DR #1103, LONGBOAT KEY, photo 31 of 65
Condominium at 2101 HARBOURSIDE DR #1103, LONGBOAT KEY, photo 32 of 65
Condominium at 2101 HARBOURSIDE DR #1103, LONGBOAT KEY, photo 33 of 65
Condominium at 2101 HARBOURSIDE DR #1103, LONGBOAT KEY, photo 34 of 65
Condominium at 2101 HARBOURSIDE DR #1103, LONGBOAT KEY, photo 35 of 65
Condominium at 2101 HARBOURSIDE DR #1103, LONGBOAT KEY, photo 36 of 65
Condominium at 2101 HARBOURSIDE DR #1103, LONGBOAT KEY, photo 37 of 65
Condominium at 2101 HARBOURSIDE DR #1103, LONGBOAT KEY, photo 38 of 65
Condominium at 2101 HARBOURSIDE DR #1103, LONGBOAT KEY, photo 39 of 65
Condominium at 2101 HARBOURSIDE DR #1103, LONGBOAT KEY, photo 40 of 65
Condominium at 2101 HARBOURSIDE DR #1103, LONGBOAT KEY, photo 41 of 65
Condominium at 2101 HARBOURSIDE DR #1103, LONGBOAT KEY, photo 42 of 65
Condominium at 2101 HARBOURSIDE DR #1103, LONGBOAT KEY, photo 43 of 65
Condominium at 2101 HARBOURSIDE DR #1103, LONGBOAT KEY, photo 44 of 65
Condominium at 2101 HARBOURSIDE DR #1103, LONGBOAT KEY, photo 45 of 65
Condominium at 2101 HARBOURSIDE DR #1103, LONGBOAT KEY, photo 46 of 65
Condominium at 2101 HARBOURSIDE DR #1103, LONGBOAT KEY, photo 47 of 65
Condominium at 2101 HARBOURSIDE DR #1103, LONGBOAT KEY, photo 48 of 65
Condominium at 2101 HARBOURSIDE DR #1103, LONGBOAT KEY, photo 49 of 65
Condominium at 2101 HARBOURSIDE DR #1103, LONGBOAT KEY, photo 50 of 65
Condominium at 2101 HARBOURSIDE DR #1103, LONGBOAT KEY, photo 51 of 65
Condominium at 2101 HARBOURSIDE DR #1103, LONGBOAT KEY, photo 52 of 65
Condominium at 2101 HARBOURSIDE DR #1103, LONGBOAT KEY, photo 53 of 65
Condominium at 2101 HARBOURSIDE DR #1103, LONGBOAT KEY, photo 54 of 65
Condominium at 2101 HARBOURSIDE DR #1103, LONGBOAT KEY, photo 55 of 65
Condominium at 2101 HARBOURSIDE DR #1103, LONGBOAT KEY, photo 56 of 65
Condominium at 2101 HARBOURSIDE DR #1103, LONGBOAT KEY, photo 57 of 65
Condominium at 2101 HARBOURSIDE DR #1103, LONGBOAT KEY, photo 58 of 65
Condominium at 2101 HARBOURSIDE DR #1103, LONGBOAT KEY, photo 59 of 65
Condominium at 2101 HARBOURSIDE DR #1103, LONGBOAT KEY, photo 60 of 65
Condominium at 2101 HARBOURSIDE DR #1103, LONGBOAT KEY, photo 61 of 65
Condominium at 2101 HARBOURSIDE DR #1103, LONGBOAT KEY, photo 62 of 65
Condominium at 2101 HARBOURSIDE DR #1103, LONGBOAT KEY, photo 63 of 65
Condominium at 2101 HARBOURSIDE DR #1103, LONGBOAT KEY, photo 64 of 65
Condominium at 2101 HARBOURSIDE DR #1103, LONGBOAT KEY, photo 65 of 65
65 photos

$1,495,000

2101 HARBOURSIDE DR #1103
LONGBOAT KEY, FL 34228
Listed by Steve Walter · MICHAEL SAUNDERS & COMPANY
Bedrooms
3
Bathrooms
2.5
Living area
2,204 sqft
Year built
1984

About this home

3BR/2.5BA, 2,219 sf end-unit villa in gated Harbour Oaks at Bay Isles. Fairway views across hole #3 (White) of the Longboat Key Club golf course, plus a full-sized private heated pool on a large screened lanai. Three sliders open the living spaces to that outdoor room, ideal for gatherings, quiet evenings, and southwest-oriented sunsets over the greens. Renovated in a clean modern-farmhouse style: shiplap fireplace, new lighting and ceiling fans, paneled interior doors with dark hardware, and a wood-and-glass front door. The open, refreshed kitchen flows into the dining area overlooking the pool and golf course. The primary suite is a true retreat with multiple closets including a walk-in, double sinks, a newly tiled glass-enclosed shower, and a bathroom skylight. Two additional bedrooms and a bonus office with golf-course and garden-atrium views give the household room to work, guest, and spread out. Practical updates include a new roof with the assessment paid and a large two-car garage with epoxy floor and organized storage for beach and sports gear. Harbour Oaks residents have use of the private Bay Isles Beach Club on the Gulf (parking available). Longboat Key Club golf, tennis, pickleball, and dining are nearby by optional separate membership; the marina is a short walk, with slips available separately. Move-in ready Longboat Key living: golf-course backdrop, private pool, beach-club access, and lock-and-leave convenience behind the Bay Isles gates. Schedule your private showing and start living the island lifestyle.

Highlights

Private poolFireplace

Property details

MLS #
MFRA4706065
Property type
Condominium
Subdivision
HARBOR OAKS PH I & II
Status
Active
Days on market
1
On market date
September 17, 2026
Stories
N/A
Total bathrooms
2.5
Garage spaces
2
Parking spaces
N/A
Lot size
N/A

Location

Get directions →
Loading map…

Nearby schools

Within 10 miles · public school directory data (NCES)

Elementary
BAY HAVEN SCHOOL OF BASICS PLUS
3.97 mi away · Grades 0-5
Nearest school -- attendance-zone data not available here
4.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
587
Student:teacher ratio
14.7:1
District
SARASOTA
MiddleCharter
SARASOTA SCHOOL OF ARTS/SCIENCES
4.74 mi away · Grades 6-8
Nearest school -- attendance-zone data not available here
2.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
752
Student:teacher ratio
18.8:1
District
SARASOTA
High
BOOKER HIGH SCHOOL
4.68 mi away · Grades 9-12
Nearest school -- attendance-zone data not available here
2.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
1,296
Student:teacher ratio
18.3:1
District
SARASOTA

Walkability

Blended score for LONGBOAT KEY's center: EPA's National Walkability Index (street network, transit, land-use mix) combined with nearby-amenity density. 60% EPA National Walkability Index + 40% nearby-amenity density (Google Places).

49
Somewhat walkable
out of 100
EPA National Walkability Index
9.5 / 20 -- Below average walkable
Nearby-amenity density
50 / 100
Restaurants & cafes6
Grocery stores1
Parks3
Schools1
Transit stops0
Pharmacies2

Mortgage calculator

Estimate only - actual rate and payment depend on your lender, credit, and loan program.

$
%
%
Adjust tax / insurance estimates
% / yr
$
/mo
Est. monthly payment
$9,153/mo
$299,000 down
$1,196,000 loan
Principal & interest$7,757
Property tax (est.)$1,246
Home insurance (est.)$150

Similar homes you might like

765 SAINT JUDES DR N
$1,350,000
765 SAINT JUDES DR N
LONGBOAT KEY, 34228
4 bd·2 ba·1,900 sqft
3 days on market
Waterfront
Listed by Kalison Nix, PREFERRED SHORE LLC
2675 GULF OF MEXICO DR #204
$1,595,000
2675 GULF OF MEXICO DR #204
LONGBOAT KEY, 34228
3 bd·3 ba·2,180 sqft
14 days on market
Waterfront
Listed by Milan Fiser, RE/MAX HARBOR REALTY
2425 GULF OF MEXICO DR #3A
$1,595,000
2425 GULF OF MEXICO DR #3A
LONGBOAT KEY, 34228
2 bd·2 ba·1,639 sqft
16 days on market
Waterfront
Listed by Roger Pettingell, COLDWELL BANKER REALTY
4545 GULF OF MEXICO DR #311
$1,200,000
4545 GULF OF MEXICO DR #311
LONGBOAT KEY, 34228
2 bd·2 ba·1,398 sqft
30 days on market
Waterfront
Listed by Janis Collier, MICHAEL SAUNDERS & COMPANY
7001 GULF OF MEXICO DR #24
$1,299,000
7001 GULF OF MEXICO DR #24
LONGBOAT KEY, 34228
2 bd·2 ba·1,190 sqft
51 days on market
Waterfront
Listed by Michael Seamon, PREMIER SOTHEBY'S INTERNATIONAL REALTY
2675 GULF OF MEXICO DR #203
$1,349,000
2675 GULF OF MEXICO DR #203
LONGBOAT KEY, 34228
2 bd·2 ba·1,896 sqft
7 days on market
Listed by SANDERLING REAL ESTATE
3040 GRAND BAY BLVD #225
$1,349,000
3040 GRAND BAY BLVD #225
LONGBOAT KEY, 34228
3 bd·3.5 ba·2,250 sqft
14 days on market
Waterfront
Listed by Bruce Myer, COLDWELL BANKER REALTY
602 BUTTONWOOD DR
$1,375,000
602 BUTTONWOOD DR
LONGBOAT KEY, 34228
3 bd·3 ba·2,107 sqft
95 days on market
Pool
Listed by COLDWELL BANKER REALTY

Data source: Listing information provided by Stellar MLS (mfrmls) via Trestle/CoreLogic. Last updated 7 days ago.

Information herein deemed reliable but not guaranteed; all measurements, school assignments, HOA fees, taxes, and feature lists are approximate and should be independently verified. Equal Housing Opportunity.