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$699,000

Active

2020 Harbourside Dr #442, Longboat Key, FL 34228

2 beds Β· 2 baths Β· 1,192 sq ft

Listing courtesy of MICHAEL SAUNDERS & COMPANY Β· MLS# A4705717

41 days on market

Refreshed from the Stellar MLS feed . This listing’s MLS record last changed .

About this home

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 bathroomsβ€”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.

Facts

Property type
Condominium
Year built
1984
Bathrooms
2 full
Living area
1,192 sqft
Waterfront
Yes Β· 325 ft
Water access
Bay/Harbor, Beach, Canal - Saltwater
Water view
Yes
Private pool
No
Exposure
Southwest
Furnished
Unfurnished
Flood zone
AE
CDD
No
55+ community
No
Annual taxes
$7,658/yr
Monthly fees
$1,963/mo
Listed
Aug 28, 2026
MLS #
A4705717

Estimate the monthly payment

Estimate by Lasbury Tracy Realty β€” not a loan offer

Starting figures for 2020 HARBOURSIDE DR #442. Everything below is editable.

AssumptionNot a quoted rate. Ask a lender what you actually qualify for today.

From this listingThe seller's most recent annual tax bill as reported to the MLS. Your bill will differ β€” Florida reassesses on sale and homestead caps reset.

Editable estimateA placeholder, not a quote. On the Gulf Coast this is the line item most likely to be wrong: premiums swing on roof age, wind mitigation, elevation, and carrier appetite. Get a real quote before you rely on this number.

Starts at $0Deliberately zero until you enter a figure β€” we will not inflate a payment with a guess. Many homes here need it; ask us for the property's flood zone and the current policy's premium.

From this listingMonthly association fee as reported to the MLS. Confirm what it includes, and ask about special assessments.

AssumptionNot applied β€” your down payment is 20% or more.

Estimated total monthly payment

$6,718

$3,535 of that is principal & interest. 47% is taxes, insurance and fees β€” which is why those inputs matter more here than the rate does.

Principal & interest
$3,535
Property taxes
$638
Homeowners insurance
$583
Flood insurance
$0
HOA / condo fees
$1,963
Mortgage insurance (PMI)
$0
Total per month
$6,718

Over the life of the loan

Loan amount
$559,200
Down payment
$139,800
Total interest
$713,229
Principal + interest paid
$1,272,429
Paid off in
2056

Interest is the exact schedule total for a fixed-rate loan held to term and assumes no extra payments. Taxes, insurance and fees are not included in these lifetime figures because they change every year.

Calculated on this page from the figures above β€” nothing is sent anywhere and no lender is quoting you. Figures are estimates for planning only, not a pre-approval, commitment to lend, or a statement of the taxes and insurance you will actually be charged. Lasbury Tracy Realty Inc. is a real estate brokerage, not a lender or an insurance agent.

Take a tour

Pick a day that suits you β€” a licensed Lasbury Tracy agent confirms personally, usually within minutes. No account needed.

2020 Harbourside Dr #442, Longboat Key, FL 34228

Listing courtesy of MICHAEL SAUNDERS & COMPANY Β· MLS# A4705717 Β· Active

How would you like to see it?
Which day?
What time of day?

In person Β· Thu, Oct 29 Β· Morning (9-12)

No account, no obligation. Prefer to talk? (941) 474-5585

Where this home is

Opens on aerial β€” on this coast the canal, the lot and the neighbours answer more questions than a street grid does.

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Listing information is provided in part by Stellar MLS, as distributed by MLS GRID. Based on information submitted to the MLS as of Oct 28, 2026, 10:24 PM (ET). All data is obtained from various sources and may not have been verified by broker or MLS. All information provided is deemed reliable but is not guaranteed and should be independently verified. 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. Some IDX listings have been excluded from this website.

Lasbury Tracy Realty Inc. Β· [email protected]