2020 Harbourside Drive, FL2020 Harbourside Drive, FL2020 Harbourside Drive, FL
Stellar MLS
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$4,995

2020 Harbourside Drive

Longboat Key, FL 34228

Listing updated: June 25, 2026 at 11:09 PM ET

Active
Stellar MLSListing courtesy of Vive Realty · Jeffrey Swanson · MLS #A4695127 · Active · 941-600-8162
2
Beds
2
Baths
1,270
Sq Ft
3.9
Acres
1984
Built
WaterfrontWater access3.9 acres$4/sqft360° tour
Condominium

Property type

1984

Year built

169,941 sqft

Lot size

$4

Price / sq ft

No HOA

HOA dues

28

Days on market

1

Garage space

About this home

Experience luxury island living in this beautifully remodeled 2-bedroom, 2-bath residence located in the highly sought-after Fairway Bay community within Bay Isles on Longboat Key. Available for immediate occupancy, this turnkey furnished coastal retreat offers flexible lease terms from 6 to 12 months. Step inside to discover a bright and open floor plan featuring upscale contemporary finishes, , updated flooring, a stunning modern kitchen with premium appliances, and elegantly renovated bathrooms. The spacious primary suite provides a peaceful retreat, while the second bedroom offers comfortable accommodations for guests or an ideal home office. Expansive living spaces and a private balcony create the perfect setting to relax and enjoy the Florida lifestyle. Residents of Fairway Bay enjoy an exceptional array of resort-style amenities, including a heated community pool, a beautifully maintained clubhouse, and a fully equipped fitness center. Tennis and pickleball enthusiasts will appreciate access to two regulation tennis courts that can also be configured into four pickleball courts, offering year-round recreation just steps from home. As part of the exclusive Bay Isles community, residents also enjoy access to the private Bay Isles Beach Club, featuring deeded Gulf-front beach access with some of Longboat Key's most beautiful sand beaches. The Beach Club offers gated parking, picnic areas, grills, restrooms, and the perfect setting to enjoy spectacular Gulf sunsets. Outdoor enthusiasts will also appreciate access to the Bay Isles marina area and kayak launch with direct access to Sarasota Bay. Ideally situated on Longboat Key, this residence is just minutes from St. Armands Circle, Longboat Key Club, championship golf courses, waterfront dining, marinas, boutique shopping, and the cultural attractions of downtown Sarasota. Whether you're seeking a seasonal retreat or an extended island stay, this residence offers the perfect combination of luxury, convenience, and coastal living. Available immediately with lease terms ranging from 6 to 12 months.

Estimated monthly payment

Principal & interest$25
Property taxes$5
Home insurance (est.)$2

Estimate only. Taxes use the listing's reported amount where available; insurance is a Florida-average estimate. Your actual payment will vary — run a full calculation or talk to a lender.

Price & listing history28 days on market

  1. Status: Active
    May 28, 2026
  2. Listed$5,950
    May 28, 2026
  3. Price reduced$4,995

Facts & features

Property type
Residential Lease
Sub type
Condominium
Status
Active
Days on market
28
Subdivision
Fairway Bay 2 Ph 1
County
Sarasota
Year built
1984
Living area
1,270 sq ft
Price/sq ft
$4
Lot size
169,941 sq ft
Garage
1 spaces
Parcel #
0008022053
MLS #
A4695127

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Interior Details

Bedrooms
2
Full bathrooms
2
Appliances
Convection Oven, Cooktop, Dishwasher, Disposal, Dryer, Electric Water Heater, Ice Maker, Microwave, Range, Refrigerator, Washer
Interior features
Ceiling Fans(s), Living Room/Dining Room Combo, Thermostat
Laundry
Inside
Stories / Levels
One

Heating & Cooling

Heating
Central
Cooling
Central Air

Parking

Garage spaces
1
Attached garage
No

HOA & Financial

Total monthly fees
$0/mo
Total annual fees
$0
HOA name
JT
Min lease term
6 Months

Exterior & Construction

Exterior features
Tennis Court(s)
Waterfront
Yes
Water access
Yes
Water view
Yes
Road surface
Asphalt

Community

Pets allowed
No

Room Details

RoomLevelDimensions
KitchenFirst

Listing Details

Listing date
2026-05-28
On market date
2026-05-28
Original list price
$5,950
Occupant type
Vacant
MLS area
34228 - Longboat Key
Listing AOR
Sarasota - Manatee
Status changed
2026-05-28

Location

Directions

From I-75, take University Parkway west toward Sarasota/Longboat Key. Continue onto Gulf of Mexico Drive through St. Armands Circle and follow Gulf of Mexico Drive north onto Longboat Key. Turn into the Bay Isles entrance and continue to Bay Harbour. The residence is located at 2020 Harbourside Drive, Unit 446.

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MLS GRID

Listings courtesy of Stellar MLS as distributed by MLS GRID

IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Based on information submitted to the MLS GRID as of June 25, 2026 at 11:09 PM ET. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

All or a portion of the multiple listing information is provided by Stellar MLS, from a copyrighted compilation of listings. The compilation of listings and each individual listing are © 2026 Stellar MLS. All rights reserved.

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