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$699,000
New Listing

2020 HARBOURSIDE DRIVE 442
LONGBOAT KEY, FL 34228

For Sale|Condominium|Active
2
Beds
2
Total Baths
2
Full Baths
1,192
SqFt
$586
/SqFt
1984
Built
Subdivision:
FAIRWAY BAY 2 PH 1
County:
Sarasota
Call Now: 941-376-4580
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941-376-4580
2020 HARBOURSIDE DRIVE 4422020 HARBOURSIDE DRIVE 4422020 HARBOURSIDE DRIVE 4422020 HARBOURSIDE DRIVE 442
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Monthly Payment (Est.)

$3,189
Calculator powered by Showcase IDX, a Constellation1 Company. Copyright ©2026 Information is deemed reliable but not guaranteed.

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.

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Listing Snapshot
Price 
$699,000
Days On Site 
0 Days
Bedrooms 
2
Inside Area (SqFt) 
1,192 sqft
Total Baths 
2
Full Baths 
2
Partial Baths 
N/A
Lot Size 
N/A
Year Built 
1984
MLS® Number 
A4705717
Status 
Active
Property Tax 
$7,658.4
HOA/Condo/Coop Fees 
$229.83 monthly
Sq Ft Source 
Public Records
Friends & Family
Recent Activity
13 hours agoListing updated with changes from the MLS®
14 hours agoListing first seen on site
General Features
Attached Garage 
Yes
Direction Faces 
Southwest
Foundation 
Pillar/Post/PierSlab
Levels 
One
Number Of Stories 
5
Parking 
Circular DrivewayCommonDrivewayGuestOff StreetOpenAttached
Pets 
Yes
Property Sub Type 
Condominium
Security 
Fire Sprinkler SystemGated CommunitySecurity GateSmoke Detector(s)
Sewer 
Public Sewer
SqFt Total 
1312
Utilities 
Cable AvailableCable ConnectedElectricity ConnectedSewer ConnectedUnderground UtilitiesWater Connected
Water Source 
PrivatePublic
Zoning 
PD
Interior Features
Appliances 
DishwasherDisposalDryerElectric Water HeaterFreezerRefrigeratorWasher
Cooling 
Central Air
Flooring 
CarpetTile
Furnished 
Unfurnished
Heating 
CentralElectric
Interior 
Elevator
Laundry Features 
Laundry Closet
Bedroom 2 
Dimensions - 12x11Level - FirstFeatures - Ceiling Fan(s)
Great Room 
Dimensions - 26x15Level - First
Kitchen 
Dimensions - 19x9Level - First
Master Bedroom 
Dimensions - 16x15Level - FirstFeatures - Ceiling Fan(s)
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Exterior Features
Construction Details 
ConcreteStucco
Exterior 
Balcony
Lot Features 
PavedPrivateWaterfront
Roof 
Built-UpConcreteMembrane
View 
Water
Waterfront 
Yes
Waterfront Features 
Beach Access
Waterview 
Water
Community Features
Association Amenities 
ClubhouseElevator(s)Fitness CenterGatedPoolRecreation FacilitiesSecurityTennis Court(s)Trail(s)
Association Fee 
$1379.0
Association Fee Frequency 
Annually
Additional Association Fee 
$1379.0
Additional Association Fee Frequency 
Annually
Community Features 
GatedClubhouseFitness CenterPoolSidewalksTennis Court(s)Street Lights
MLS Area 
34228 - Longboat Key
Township 
36S
Financing Terms Available 
CashConventional
Roads 
Asphalt
Schools
School District
Unknown
Elementary School
Southside Elementary
Middle School
Booker Middle
High School
Booker High
Listing courtesy of MICHAEL SAUNDERS & COMPANY (941) 809-0907



Listing information is provided by Participants of the Stellar MLS. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Properties displayed may be listed or sold by various participants in the MLS Copyright 2026, Stellar MLS.
Last checked: 2026-09-18 05:59 AM EDT

Neighborhood & Commute
Source: Walkscore
Disclosure: Community information and market data powered by Constellation Data Labs. Information is deemed reliable but not guaranteed.
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