Sell Your Home
Get a free home valuation
Contact
Tell us about your needs

2020 HARBOURSIDE DRIVE UNIT 442

Condo/Co-op For Sale
$699,000

BTC: 8.73750000

ETH: 279.60000000

7 days
Waterfront
2 bds
2 ba
1,192 sqft

Overview

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.

Location

Details

Type:
Residential
Parking:
Circular Driveway / Common / Driveway / Ground Level / Guest / Off Street / Open
Year Built:
1984
Lot:
No Data
Heating:
Central / Electric
Price/sqft:
$586
Cooling:
Central Air
HOA:
$1,379

Valuation

Our model vs. what's actually selling nearby.
Estimate
$598,750
$371K – $1.3M
Confidence Low
List vs. estimate
$100K above estimate
List $699,000 · +16.7%
Our model says this listing is priced above recent comparable activity. Room to negotiate.
Price per sq ft
$586
-4.2% vs. city median $612
Based on
45 MLS comparables
Median of recent comparable listings. Sold comps use closing price, active listings use list price.

Highlights

Annual tax
$7,658
2025
HOA
$1,379/yr
24-Hour Guard, Common Area Taxes, Community Pool
View
Water
Waterfront
Bay/Harbor Front, Canal Front
Pets
Allowed
All facts and features
  • Flooring

    • Carpet

    • Porcelain Tile

    Heating

    • Central

    • Electric

    Cooling

    • Central Air

    Appliances

    • Built-In Oven

    • Dishwasher

    • Disposal

    • Dryer

    • Electric Water Heater

    • Freezer

    • Refrigerator

    • Washer

    Other interior features

    • Ceiling Fan(s)

    • Kitchen/Family Room Combo

    • Solid Surface Counters

    • Thermostat

    Bedrooms and bathrooms

    • Bedrooms: 2

    • Full bathrooms: 2

  • Parking

    • Circular Driveway

    • Common

    • Driveway

    • Ground Level

    • Guest

    • Off Street

    • Open

    Property

    • Levels: One

    • Exterior Features: Balcony / Sidewalk / Sliding Doors

    Other Property Information

    • Parcel Number: 0008022050

    • Zoning: PD

  • Type and style

    • Property Type: Residential

    • Property Sub Type: Condominium

  • Utility

    • Cable Connected

    • Electricity Connected

    • Public

    • Sewer Connected

    • Street Lights

    • Underground Utilities

    • Water Connected

  • Other financial information

    • HOA: $1,379

    • HOA Frequency: Annually

    • Annual tax amount: $7,658

  • Source details

    • MLS ID: A4705717

    Other facts

    • Construction Materials: Concrete / Stucco

    • Foundation Details: Pillar/Post/Pier / Slab

    • Laundry Features: Laundry Closet

    • Window Features: Shades

    • Direction Faces: Southwest

    • Waterfront: Yes

    • Water Body Name: SARASOTA BAY & BAY ISLES CANAL

    • Attached Garage: Yes

    • Living Area: 1192

    • Water Source: Private / Public

    • Subdivision Name: FAIRWAY BAY 2 PH 1

Private inquiry
Talk to the advisor on this listing.
Floor plans, HOA docs, off-market comparables, scheduling a private showing — one message, direct to the local specialist.

More like this

New
For Sale
$489,900
1 bds · 1 ba · 528 sqft
SEA HORSE BEACH RESORT, LONGBOAT KEY
3453 GULF OF MEXICO DRIVE UNIT 242
For Sale
$499,000
Condo/Co-op
2 bds · 2 ba · 1,072 sqft
LONGBOAT HARBOUR, LONGBOAT KEY
4370 CHATHAM DRIVE UNIT 304
For Sale
$799,000
Condo/Co-op
2 bds · 2 ba · 1,590 sqft
FAIRWAY BAY 1, LONGBOAT KEY
1906 HARBOURSIDE DRIVE UNIT 303
For Sale
$520,000
Condo/Co-op
2 bds · 2 ba · 1,072 sqft
LONGBOAT HARBOUR, LONGBOAT KEY
4310 FALMOUTH DRIVE UNIT 307
For Sale
$624,900
Condo/Co-op
2 bds · 2 ba · 1,186 sqft
LONGBOAT ARMS, LONGBOAT KEY
3320 GULF OF MEXICO DRIVE UNIT 206C
For Sale
$835,000
House
3 bds · 2 ba · 2,478 sqft
HARBOUR OAKS 2, LONGBOAT KEY
2321 HARBOUR OAKS DRIVE
For Sale
$725,000
Condo/Co-op
2 bds · 2 ba · 1,194 sqft
BAY HARBOUR APTS, LONGBOAT KEY
448 GULF OF MEXICO DRIVE UNIT A104
-$11K
For Sale
$689,000
Condo/Co-op
2 bds · 2 ba · 1,260 sqft
PORTOBELLO, LONGBOAT KEY
3240 GULF OF MEXICO DRIVE UNIT B504

Market around this address

Live counts in the same area.
View all

The multiple listing information is provided by the Stellar MLS from a copyrighted compilation of listings. The compilation of listings and each individual listing are ©2026-present Stellar MLS. All Rights Reserved. The information provided is for consumers' personal, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. All properties are subject to prior sale or withdrawal. All information provided is deemed reliable but is not guaranteed accurate, and should be independently verified. Listing courtesy of: MICHAEL SAUNDERS & COMPANY