2020 Harbourside Dr #442, photo 1
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Overview

2 bd2 ba1,192 sqftCondominium
TypeCondominium
HOA + condo dues$1,848/mo
Built1984
Living area1,192 sqft
Price / sqft$586

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Pricing, comps, HOA, the neighborhood. Answers before you fill out anything.

About this home

Ceiling Fans(s)Kitchen/Family Room ComboSolid Surface CountersThermostatBalconySidewalkBuyer Approval RequiredClubhouse

2020 Harbourside Dr #442 is a 1984-built home in Fairway Bay 2 Ph 1, Longboat Key. Inside you'll find 2 bedrooms, 2 bathrooms, and 1,192 square feet of living space. Listed at $699,000 (about $586/sqft), 45 days on market. Flood zone AE - confirm flood insurance requirements with your lender. HOA runs $1,379 annually. Condo dues run $1,733 monthly.

From the listing

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.

The essentials

Built
1984
Price / sqft
$586
On market
45 days
Annual tax
$7,658
HOA + condo dues
$1,848/mo
Flood zone
AE
Type
Condominium

At a glance

Condo
5 stories · 1984
Waterfront
Bay/Harbor
Community pool
Fitness center too
Private balcony
Outdoor space
1,192 sqft
Living area

Payment

Est. monthly payment
$6,482/mo
Down payment (20%)
$139,800
Property taxes
$638/mo
HOA + condo dues
$1,848/mo
Rate assumed
6.8% · 30 yr
View full breakdown

Details

Type
Condominium
Year Built
1984
Lot
-
Cooling
Central Air
Heating
Central, Electric
Parking
Circular Driveway, Common, Driveway, Ground Level, Guest, Off Street, Open
Waterfront
Bay/Harbor
Days on Market
45
Ceiling Fans(s)
Kitchen/Family Room Combo
Solid Surface Counters
Thermostat
Balcony
Sidewalk
Buyer Approval Required
Clubhouse
Fitness Center
Gated Community - Guard
Pool
Sidewalks
Tennis Court(s)
Street Lights
Built-in Oven
Dishwasher
Disposal
Dryer
Electric Water Heater
Freezer
Refrigerator
Washer
Elementary
Southside Elementary
Middle
Booker Middle
High
Booker High

Districts can re-zone, so verify directly with the district before relying on these.

Flood Zone AE
Annual Tax (2025)
$7,658
Parcel #
0008022050

Taxes reflect the most recent assessment in the MLS feed. Actual tax owed can vary, so confirm with the county property appraiser before closing.

Subdivision
Fairway Bay 2 Ph 1
County
Sarasota
MLS Area
34228 - Longboat Key
Lot Size
-
PavedPrivate
HOA + condo dues
$1,848/mo
$115/mo HOA plus $1,733/mo condo dues
Nat Veal

Price history

Date
Event
Price
8/28/2026
Listed for sale
Source: Stellar MLS #A4705717
$699,000
$586/sqft

Neighborhood

2020 Harbourside Dr #442
Longboat Key, FL, 34228 · 34228 - Longboat Key

Market insights

Offer Insights

Choose an offer strength

List price: $699,000
$660,000 – $699,000
94.3% – 100% of listTops out right at the list price
80% of listList price
69 of the last 136 condo closings in 34228 landed at this number or higher (51%). The median one sat 86 days before it went under contract, and this one is on day 45.

Sample: 136 closed condo sales in 34228 over the last 8 months, Stellar MLS. A starting point, not a guarantee.

Talk through an offer with our team

Calculator

Est. monthly payment
$6,481/mo
Principal & interest$3,646
Property taxes$638
Insurance$350
HOA$1,848
Down payment20% · $139,800
Interest rate6.80%
Loan term

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Property taxes are this home's actual annual bill from the MLS, divided by twelve. Insurance estimated at 0.60%. HOA includes any condo dues reported on the listing. Rate defaults to 6.8% on a 30-year fixed. Tap a pencil to use your own numbers. Estimates only, not a loan quote.

Quick answers.

Price

$699,000

$586 per sq ft

Beds and baths

2 beds, 2 baths

Size

1,192 sq ft

Time on market

45 days

Year built

1984

Monthly payment

About $6,482/mo

That is 20% down on a 30-year fixed at 6.8%, plus the home's $7,658 annual tax bill, insurance, and $1,848/mo in HOA and condo dues.

HOA + condo dues

$1,848/mo

$115/mo HOA plus $1,733/mo condo dues. Managed by Nat Veal.

Flood zone

Zone AE

That is a high-risk designation, so a lender will normally require flood insurance. Confirm the current rate before you write an offer.

Offer

What should I offer?

Have another question?

Brokered byMICHAEL SAUNDERS & COMPANYListing agent: Steve WalterListing data from Stellar MLS, MLS# A4705717.

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