$724,000
2020 Harbourside Drive
Longboat Key, FL 34228
Listing updated: June 24, 2026 at 3:28 PM ET
Listing courtesy of Coldwell Banker Realty · Bruce Myer · MLS #A4696667 · Active · 941-383-6411Property type
Year built
Price / sq ft
HOA dues
Day on market
Garage space
Flood zone
About this home
Located on the 5th-floor penthouse level of Fairway Bay, this corner 2BR/2BA residence offers beautiful views of Sarasota Bay, the downtown skyline, manicured grounds, pool, and mangrove channels. Garage parking, a rare and desirable feature on Longboat Key, adds to the appeal. From the moment you enter, a wall of sliders draws your eye through the living room to the bay beyond. Tile floors run through the main living areas, and the open layout includes a spacious living room with a flexible bump-out area ideal for extra seating, a reading nook, or workspace. The dining area flows to the kitchen, which features a functional layout, breakfast bar, and adjoining eat-in area with sliders opening to the side terrace. The primary suite offers bay views, built-ins, a walk-in closet, direct terrace access, and a bath with dual vanities, separate water closet, and excellent potential for updating. The guest bedroom is comfortable and includes an en suite bath. The corner terrace extends the living space outdoors, offering a peaceful setting from morning light on the water to the evening glow of downtown. One of the true highlights of Bay Isles living is deeded private beach access through the Bay Isles Beach Club, a resident-only Gulf-front retreat with an on-site attendant, covered gathering and picnic areas, restrooms, changing rooms, barbecue grills, volleyball court, and beach accessory storage. Fairway Bay residents also enjoy 24-hour gated security, tennis courts, fitness facilities, walking paths, and the benefits of Bay Isles living. Optional Longboat Key Club memberships offer access, depending on category, to championship golf, Har-Tru tennis, private dining, beach and pool club facilities, spa, fitness center, wellness studio, club events, and marina amenities. Deepwater slips may also be available separately.
Local Insight
At $502/sqft for a 1984 waterfront unit, you're getting below-market pricing for Longboat Key's Gulf Coast location, but the age means you should budget for potential updates and carefully review what the "water access" actually entails—whether it's direct Gulf frontage or bay-side with shared amenities. The AE flood zone designation is standard for waterfront here, but confirm flood insurance costs since that's a real annual expense that changes the true cost of ownership. Fairway Bay is an older, ungated community without HOA, which offers flexibility but less resort-style infrastructure than the island's newer private developments—worth visiting to see if the trade-off between independence and amenities fits your lifestyle.
AI-generated insight based on listing data and neighborhood context. Verify independently.
Estimated monthly payment
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 history1 days on market
- Status: ActiveJun 23, 2026
- Listed$724,000Jun 23, 2026
- Price increased$724,000
Facts & features
- Property type
- Residential
- Sub type
- Condominium
- Status
- Active
- Days on market
- 1
- Subdivision
- Fairway Bay 2 Ph 1
- County
- Sarasota
- Year built
- 1984
- Living area
- 1,442 sq ft
- Price/sq ft
- $502
- Building area
- 1,652 sq ft (Public Records)
- Lot size
- 0 sq ft
- Lot category
- Non-Applicable
- Flood zone
- AE
- Garage
- 1 spaces
- Annual taxes
- $9,366 (2025)
- Parcel #
- 0008022060
- Zoning
- PD
- MLS #
- A4696667
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Interior Details
- Bedrooms
- 2
- Full bathrooms
- 2
- Flooring
- Carpet, Tile
- Appliances
- Dishwasher, Disposal, Dryer, Electric Water Heater, Microwave, Range, Refrigerator, Washer
- Interior features
- Built-in Features
- Laundry
- Inside
- Stories / Levels
- One
- Direction faces
- West
Heating & Cooling
- Heating
- Central, Electric
- Cooling
- Central Air
Parking
- Garage spaces
- 1
- Attached garage
- Yes
- Parking features
- Basement
HOA & Financial
- Total monthly fees
- $1,848/mo
- Total annual fees
- $22,179
- HOA name
- Advanced Management
- CDD
- No
- Min lease term
- 2 Months
- Listing terms
- Cash, Conventional
- Ownership
- Fee Simple
- Available for lease
- Yes
- Lease restrictions
- Yes
- Additional lease restrictions
- See Documents
- Approval process
- See Documents
Exterior & Construction
- Exterior features
- Sliding Doors, Tennis Court(s)
- Construction materials
- Concrete, Stucco
- Roof
- Other
- Foundation
- Pillar/Post/Pier
- Waterfront
- Yes
- Water access
- Yes
- Water view
- Yes
- Road surface
- Paved
Utilities
- Sewer
- Public Sewer
- Water source
- Private
- Utilities
- Electricity Connected, Sewer Connected, Underground Utilities, Water Connected
Community
- Pets allowed
- Yes
Room Details
| Room | Level | Dimensions |
|---|---|---|
| Living Room | First | 21x18 |
| Kitchen | First | 9x18 |
| Dining Room | First | 14x7 |
| Primary Bedroom | First | 14x18 |
| Bedroom 2 | First | 12x11 |
| Balcony/Porch/Lanai | First | 15x9 |
| Den | First | 7x9 |
| Balcony/Porch/Lanai | First | 15x6 |
Listing Details
- Listing date
- 2026-06-23
- On market date
- 2026-06-23
- Original list price
- $724,000
- Occupant type
- Vacant
- MLS area
- 34228 - Longboat Key
- Listing AOR
- Sarasota - Manatee
- Status changed
- 2026-06-23
- Tax legal description
- UNIT 457 BLDG M-4 FAIRWAY BAY 2 PHASE 1
Flood risk
FEMA Special Flood Hazard Area (1% annual-chance / “100-year” floodplain). Flood insurance is generally required by mortgage lenders.
Source: FEMA flood zone reported on the listing. Confirm current designation at FEMA Flood Map Service Center.
Location
Directions
From St. Armands Circle, exit the circle heading north on N Boulevard of the Presidents / FL-789. Cross the New Pass Bridge onto Longboat Key and continue straight as the road becomes Gulf of Mexico Drive / FL-789. Turn right onto Bay Isles Parkway and proceed through the Bay Isles guard gate. After the gate, continue about half a mile; the 2020 Harbourside Drive building will be on your right. Use guest parking when you arrive.
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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 24, 2026 at 3:28 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.
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