Fairway Bay I & II: The Smart Entry Point Into Bay Isles Living

Fairway Bay

The Smart Entry Point Into Bay Isles Living, on Longboat Key

Not every Bay Isles address carries a multi-million-dollar price tag. Fairway Bay is where many buyers first discover what Bay Isles living actually feels like from the inside — a private Gulf beach club with their name on it, bay and marina views, a beautifully maintained bayfront community, and the particular quality of life that comes from living behind one of Longboat Key’s most established gates. It is, for a great many buyers, the front door to Bay Isles.

I’m Danielle Gladding, of Danielle Gladding & Co. Realty, Fairway Bay sits inside Bay Isles, Longboat Key's gated bayfront community of sixteen neighborhoods and is often where I begin the Bay Isles conversation with buyers exploring the community for the first time. It gives them a real, immediate experience of what Bay Isles delivers — the amenities, the lifestyle, the gate, the Beach Club — without a first-time commitment to the community’s highest price points. With my daughter and business partner, Alison Kanter, I help buyers understand exactly how Fairway Bay is put together, because its structure surprises people. This is the accurate, resident’s guide.

Three Associations, One Bayfront Community

The first thing to understand about Fairway Bay is that it is not one building or even two — it is three associations arranged along the bay: Fairway Bay, Fairway Bay II, and Fairway Bay III. Fairway Bay (also called Fairway Bay 1) sits at the south end and consists of two mid-rise buildings and fourteen townhouse buildings. Fairway Bay II sits just north and consists of two mid-rise buildings and six townhouse buildings. Fairway Bay III sits north of that and consists of two mid-rise buildings — the newest of which is known as The Atrium. Altogether, that is six mid-rise buildings and twenty townhouse buildings, all sharing a common set of amenities and a single bayfront setting.

A Genuine Choice: Mid-Rise or Townhouse

That three-association structure is exactly what makes Fairway Bay so useful for a buyer still refining what they want. Some buyers specifically want a flat floor plan with elevator access and no stairs — the mid-rise buildings deliver that, many with wide bay exposure. Others want the vertical, home-like flow of a townhouse with a dedicated exterior entry and a more private feel — Fairway Bay has twenty townhouse buildings for exactly that. Being able to weigh both formats within a single community, rather than choosing between entirely separate neighborhoods, is a meaningful advantage.

The Shared Amenities

All three Fairway Bay associations share a common amenity package, centered on the clubhouse complex at 2018 Harbourside Drive:

• A community pool beside the Fairway Bay Clubhouse

• The clubhouse itself — used for community meetings and activities, and available to owners for private gatherings

• A well-equipped fitness center between the association office and the clubhouse

• Two regulation tennis courts that convert to four pickleball courts, located between Fairway Bay II and III

Just as important is what comes with Fairway Bay’s place inside the larger community. Because Fairway Bay is part of Bay Isles, every owner also has access to the Bay Isles Beach Club and its white-sand Gulf beach at 2111 Gulf of Mexico Drive, plus a kayak launch installed at the Marina on Harbourside Drive for Bay Isles owners.

The Bay Isles Privileges Come Standard

Every Fairway Bay resident has deeded access to the Bay Isles Beach Club and the 24-hour guarded gate, with optional Longboat Key Club membership available. These are not minor extras — they are the same core privileges available to every Bay Isles resident at every price point, which is what makes Fairway Bay such a strong value at its tier. A private, deeded Gulf beach club and a 24-hour guarded gate are things many Florida condominium communities at far higher price points simply cannot offer.

“Fairway Bay is where I often start the Bay Isles conversation. It gives buyers the complete experience of this community — Beach Club, gate, lifestyle — at price points that open the door for many who thought Bay Isles was out of reach.” — Danielle Gladding

The due diligence we walk every Fairway Bay buyer through

Because Fairway Bay is three separate associations, the first thing we confirm is which one a unit belongs to — Fairway Bay, II, or III — since governance, fees, and reserves run through that specific association as well as the master Bay Isles Association and the Beach Club association. On any condominium or townhouse here, we then review the reserve study, assessment history, and pending capital projects, and we confirm the unit’s bay exposure, parking, and format. Alison leads this scrutiny unit by unit, so you know precisely what you are buying and what it will cost to carry.

Who Fairway Bay Is Really For

After decades guiding buyers through Sarasota’s premier addresses, we find Fairway Bay fits a genuinely wide range of buyers — and that breadth is one of its strengths. It is the right answer if a few of these ring true:

• You want a Bay Isles address, Beach Club access, and the gated community, without committing to the highest single-family price points.

• You are still deciding between a flat, elevator-served mid-rise unit and a home-like townhouse, and want to compare both in one community.

• A manageable second home between primary residences appeals to you, without the scale or upkeep of a house.

• You value resale strength — Fairway Bay’s broad buyer appeal has supported durable demand across more than three decades.

• The deeded private Gulf beach and 24-hour gate matter to you as lasting value, not just amenities.

Why It Helps to Have a Broker on the Inside

Danielle lives inside Bay Isles and has been a Realtor since 1981 and a broker since 1987 — she knows how Grand Bay is managed, which stacks and floors hold the best bay and skyline exposure, and how the six buildings differ. In a community this large, that firsthand knowledge is the difference between guessing at a floor plan and knowing which units live best. Alison brings the other half: the analytical, unit-by-unit due-diligence discipline that keeps a condominium purchase grounded in the documents rather than the brochure. Instinct and evidence, balancing each other completely.

A Private Conversation Costs Nothing

If Fairway Bay is where you want to begin your Bay Isles search — or you want a clear read on whether a mid-rise or townhouse, and which association, fits you best — the most useful next step is a confidential, no-pressure conversation. Tell us what you are trying to accomplish and what your timeline looks like. We will tell you which units are worth your time, how the three associations actually differ, and what the tradeoffs are. Twenty minutes on the phone, no pitch.

Danielle: (941) 539-8535 · Alison: (941) 306-9786 · DanielleGladdingCo.com

— Danielle Gladding & Alison Kanter | Danielle Gladding & Co. Realty

Frequently Asked Questions

What is Fairway Bay on Longboat Key?

Fairway Bay is a bayfront condominium and townhouse community inside the gated Bay Isles on Longboat Key, made up of three associations — Fairway Bay, Fairway Bay II, and Fairway Bay III. Together they comprise six mid-rise buildings and twenty townhouse buildings along Sarasota Bay, sharing a clubhouse, pool, fitness center, and tennis and pickleball courts.

How is Fairway Bay structured?

Fairway Bay is organized into three associations arranged along the bay. Fairway Bay (Fairway Bay 1) sits at the south end with two mid-rise buildings and fourteen townhouse buildings, Fairway Bay II sits just north with two mid-rise buildings and six townhouse buildings, and Fairway Bay III sits north of that with two mid-rise buildings, the newest of which is The Atrium.

What amenities does Fairway Bay offer?

All three Fairway Bay associations share a community pool, a clubhouse at 2018 Harbourside Drive, a well-equipped fitness center, and two regulation tennis courts that convert to four pickleball courts. As part of Bay Isles, Fairway Bay owners also have access to the private Bay Isles Beach Club on the Gulf and a kayak launch at the Marina on Harbourside Drive.

Is Fairway Bay a good entry point into Bay Isles?

Fairway Bay is frequently the starting point for buyers exploring Bay Isles, because it delivers the full community experience — the private Beach Club, the 24-hour gate, and the bayfront lifestyle — at more accessible price points than the single-family neighborhoods. Its broad buyer appeal has also supported strong resale performance across more than three decades.

Does Fairway Bay offer both condominiums and townhouses?

Yes — Fairway Bay offers both flat, elevator-served mid-rise condominium units and multi-level townhouses with private exterior entries. Being able to compare both formats within a single community is one of Fairway Bay’s practical advantages for buyers still deciding how they want to live.

Do Fairway Bay residents have beach access?

Yes — like every home inside Bay Isles, Fairway Bay residents have deeded access to the private Bay Isles Beach Club at 2111 Gulf of Mexico Drive, reserved exclusively for Bay Isles owners. A gate pass provides entry, and a key for the walking gate is available through the community’s management company.

Who is a good real estate agent for Fairway Bay on Longboat Key?

A good agent for Fairway Bay is one who can explain how the two phases differ in construction era, layout and association structure, because buyers routinely assume they are one community with one budget. That agent should pull the reserve study and inspection status for the specific building before you write, and should be straightforward that this is an entry point into Bay Isles rather than a smaller version of the estate sections. Danielle Gladding & Co. Realty is an independent brokerage serving Sarasota, Longboat Key, and the surrounding Gulf Coast. Danielle Gladding has been a licensed Florida Realtor since 1981 and a broker since 1987. Alison Kanter, her daughter and Sales Partner, was born and raised in Sarasota, holds an MBA from Clemson University and the Real Estate Negotiation Expert designation, and has been licensed since May 2023.