Condominium at 2020 HARBOURSIDE DR #442, LONGBOAT KEY
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$699,000

2020 HARBOURSIDE DR #442
LONGBOAT KEY, FL 34228
Listed by Steve Walter · MICHAEL SAUNDERS & COMPANY
Bedrooms
2
Bathrooms
2
Living area
1,192 sqft
Year built
1984

About this home

Enjoy direct Sarasota Bay views and deeded private beach access from this updated fourth-floor residence in Fairway Bay, an established gated Bay Isles community within the Longboat Key Club setting. Residence #442 at 2020 Harbourside Drive offers 1,312 square feet of bright, airy living space with two bedrooms and two bathrooms—an inviting coastal retreat where the bay becomes part of everyday life. Floor-to-ceiling views from the kitchen, dining area, and living room create a memorable backdrop for daily living and entertaining, while the private balcony is an ideal place to begin the day with a Sarasota Bay sunrise or settle in for the evening as the sky changes over the water. Keep watch for passing boats, coastal birds, and the occasional manatee in the bay below. The residence has been thoughtfully updated with a kitchen featuring granite countertops, a granite breakfast bar, stainless-steel appliances, and a newer microwave. A front-loading LG washer and dryer are included for everyday convenience. Ceramic tile flooring extends throughout the main living areas and guest spaces, while the primary bedroom features warm wood flooring. Fairway Bay offers a resort-inspired waterfront lifestyle with scenic walking paths, a heated swimming pool and spa, fitness facilities, social spaces, tennis courts, and paddle sports. Beyond the bayfront setting, owners enjoy deeded access to the Bay Isles Beach Club, providing a private connection to Longboat Key’s renowned Gulf beaches. It is the best of both waterfront worlds: tranquil Sarasota Bay just outside your door and the Gulf of Mexico’s white-sand shoreline close by. The community’s central island location makes it easy to walk or bike to nearby conveniences, including grocery shopping, pharmacy services, and tennis. For those who wish to expand their recreational options, membership opportunities may be available through the nearby Longboat Key Club, with its golf, tennis, dining, fitness, spa, and full-service deep-water marina amenities. St. Armands Circle is moments away for boutique shopping and acclaimed dining, while downtown Sarasota offers a vibrant extension of the island lifestyle with arts, culture, restaurants, and waterfront attractions. This is a rare opportunity to enjoy a beautifully updated fourth-floor bayfront residence where views, private beach access, resort-style amenities, and the effortless rhythm of Longboat Key living come together.

Highlights

Waterfront

Property details

MLS #
MFRA4705717
Property type
Condominium
Subdivision
FAIRWAY BAY 2 PH 1
Status
Active
Days on market
1
On market date
September 17, 2026
Stories
N/A
Total bathrooms
2
Garage spaces
N/A
Parking spaces
N/A
Lot size
N/A
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Nearby schools

Within 10 miles · public school directory data (NCES)

Elementary
BAY HAVEN SCHOOL OF BASICS PLUS
3.72 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
4.44 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
4.45 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

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Est. monthly payment
$4,359/mo
$139,800 down
$559,200 loan
Principal & interest$3,627
Property tax (est.)$583
Home insurance (est.)$150

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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.