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2020 Harbourside Drive , #442

Longboat Key, FL 34228
  • $699,000
  • STATUS: Active
  • ON SITE: 26 Days
  • MLS #: A4705717
$699,000
  • 2
    BEDS
  • N/A
    ACRES
  • 2
    BATHS
  • 0
    1/2 BATHS
  • 1,192
    SQFT
  • $586
    $/SQFT
Neighborhood:
Type:
Condo
Built:
1984
County:
Area:

School Information

Elementary School:
Middle School:
High School:

Description

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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© 2026 My Florida Regional MLS DBA Stellar MLS. All rights reserved. All listings displayed pursuant to IDX. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided for consumers personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Data last updated 2026-10-13T23:43:02.883.
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2020 Harbourside Drive , #442 Longboat Key, FL 34228

  • Price: $699,000
  • Status: Active
  • On Site: 26 Days
  • MLS #: A4705717
2
Beds
2
Baths
0
½ Baths
N/A
Acres
1,192
SQFT
$586
$/SQFT
1984
Built
Neighborhood:
Fairway Bay 2 Ph 1
County:
Sarasota
Area:
Longboat Key
Elementary School:
Southside Elementary
Middle School:
Booker Middle
High School:
Booker High
Property Description
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.
Exterior Features

Attached Garage Yn Yes Carport Yn No Construction Materials ConcreteStucco Direction Faces Southwest Exterior Features BalconySidewalkSliding Doors Foundation Details Pillar/Post/PierSlab Open Parking YN Yes Parking Features Circular DrivewayCommonDrivewayGround LevelGuestOff StreetOpen Pool Private Yn No Road Frontage Type Street PavedPrivate Road Road Surface Type PavedAsphalt Roof Built-UpConcreteMembrane Spa YN No View Water Water Access Bay/HarborBeachCanal - Saltwater Water Access Yn Yes Water Body Name SARASOTA BAY & BAY ISLES CANAL Water Extras Minimum Wake ZoneNo Wake ZoneRiprap Water Extras Yn Yes Water View Bay/Harbor - FullIntracoastal Waterway Water View Yn Yes Waterfront Features Bay/Harbor FrontCanal FrontBay/Harbor Waterfront Yn Yes

Interior Features

Additional Rooms Great RoomInside Utility Appliances Built-In OvenDishwasherDisposalDryerElectric Water HeaterFreezerRefrigeratorWasher Building Area Total 1312 Building Elevator Yn Yes Cooling Central Air Cooling YN Yes Fireplace Yn No Flooring CarpetPorcelain Tile Furnished Unfurnished Heating CentralElectric Heating YN Yes Interior Features Ceiling Fan(s)Kitchen/Family Room ComboSolid Surface CountersThermostat Laundry Features Laundry Closet Levels One Sewer Public Sewer Stories Total 5 Water Source PrivatePublic Window Features Shades

Property Features

Additional Lease Restrictions See Association Docs Additional Parcels YN No Approval Process See Association Docs Association Amenities ClubhouseElevator(s)Fitness CenterGatedLobby Key RequiredPickleball Court(s)PoolRecreation FacilitiesSecurityTennis Court(s)Trail(s) Association Approval Required Yn Yes Association Fee 1379 Association Fee Frequency Annually Association Fee Includes 24-Hour GuardCommon Area TaxesCommunity PoolEscrow Reserves FundInsuranceMaintenance StructureMaintenance GroundsManagerPool MaintenancePrivate RoadRecreational FacilitiesSecurity Association Fee Monthly Amount 114.92 Association Fee Requirement Required Association Fee2 1379 Association Fee2 Frequency Annually Association Montly Maint Amt Add To Hoa 0 Association Yn Yes Building Name Number M-4 Cdd Yn No Community Features Bay/Harbor FrontCanal FrontBuyer Approval RequiredClubhouseFitness CenterGated Community - GuardPoolSidewalksTennis Court(s) Condo Fee Monthly Amount 1733 Condo Fees 5200 Condo Fees Term Quarterly Condo Land Included Yn No Down Payment Resource Yes Flood Zone Code AE Floor Number 4 Garage Yn No Homestead Yn No Lease Considered YN Yes Lease Restrictions YN Yes Listing Terms CashConventional Max Pet Weight 35 Minimum Lease 2 Months New Construction Yn No Number Of Pets 1 Occupant Type Vacant Ownership Condominium Pet Restrictions See Association Docs Pet Size Small (16-35 Lbs.) Pets Allowed Yes Property Attached YN No Property Condition Completed Property Sub Type Condominium Security Features Fire Sprinkler SystemGated CommunitySecurity GateSmoke Detector(s) Senior Community Yn No Special Listing Conditions None Sw Subdiv Community Name Fairway Bay Tax Annual Amount 7658.4 Total Annual Fees 23558 Total Monthly Fees 1963.17 Utilities Cable ConnectedElectricity ConnectedPublicSewer ConnectedStreet LightsUnderground UtilitiesWater Connected Yrs Of Owner Prior To Leasing Re No Zoning PD


Listing information © 2026 My Florida Regional MLS DBA Stellar MLS..
Listing provided courtesy of MICHAEL SAUNDERS & COMPANY: 941-383-7591.



© 2026 My Florida Regional MLS DBA Stellar MLS. All rights reserved. All listings displayed pursuant to IDX. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided for consumers personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Data last updated 2026-10-13T23:43:02.883.
 
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