Harbour Circle Bay Isles | Danielle Gladding & Co.

Developed in the late 1980s, Harbour Circle is a villa neighborhood inside Bay Isles on Longboat Key. It's a community of contemporary Spanish-style villas at the very north end of South Bay Isles — 42 homes in all, mostly three-bedroom, two-and-a-half-bath villas ranging from roughly 2,187 to 2,966 square feet. It is maintenance-free, yet residents own the land their villa sits on, so several homes have private pools as well. With the Harbourside Golf Course as its backyard, Harbour Circle is one of the most visible communities in Bay Isles, seen from both Gulf of Mexico Drive and Bay Isles Parkway.

I’m Danielle Gladding, of Danielle Gladding & Co. Realty, and I know Harbour Circle from the inside — I live in Bay Isles, in Queens Harbour, and have worked this market since 1981. With my daughter and business partner, Alison Kanter, I help buyers understand what this Spanish-style, land-owned villa community really offers. This is the accurate, resident’s guide.

Forty-Two Spanish-Style Villas

Harbour Circle consists of 42 villas, mostly three-bedroom, two-and-a-half-bath homes ranging from approximately 2,187 to 2,966 square feet — substantial, single-level-oriented living in a contemporary Spanish architectural style. Developed in the late 1980s at the very north end of South Bay Isles, the community has a distinctive, cohesive look that makes it one of the most recognizable in Bay Isles.

Maintenance-Free — But You Own Your Land

Here is the distinction that matters most at Harbour Circle: it is a maintenance-free community, with a shared community pool and spa, yet residents own the land their villa sits on. That land ownership is unusual within a maintenance-free structure, and it is why several homes have their own private pools in addition to the community pool. Buyers get the lock-and-leave ease of maintenance-free living with a degree of ownership and flexibility that most maintenance-free communities do not offer.

The Harbourside Golf Course as a Backyard

Harbour Circle calls the Longboat Key Club’s Harbourside Golf Course its backyard, and its prominent position — visible from both Gulf of Mexico Drive and Bay Isles Parkway — gives it real presence. For buyers who want a golf-course setting with a distinctive architectural identity, this is a rare combination inside the gates.

A Friendly, Diverse Community

Harbour Circle is known as a very friendly community with residents of all ages and backgrounds. Neighbors gather for seasonal barbecues on the pool deck and usually celebrate the holidays with an organized dinner at a local restaurant. And like every home inside the gates, a Harbour Circle villa carries the shared Bay Isles privileges — deeded access to the private Bay Isles Beach Club on the Gulf, and the 24-hour guarded community gate.

The due diligence we walk every Harbour Circle buyer through

Harbour Circle’s maintenance-free-but-land-owned structure is unusual, so we confirm exactly what the association maintains versus what the owner is responsible for, alongside the reserve study and assessment history. On late-1980s villas, we also look at systems age, roof and exterior condition, and whether a specific home has a private pool. Alison leads this scrutiny villa by villa, so you know exactly what you are buying and what it will cost to carry.

Who Harbour Circle Is Really For

After decades guiding buyers through Sarasota’s premier addresses, we find Harbour Circle fits a clear kind of buyer. It is the right answer if a few of these ring true:

• You want a substantial villa — three bedrooms, 2,187 to 2,966 square feet — with a distinctive Spanish architectural character.

• Maintenance-free living appeals to you, but so does owning the land your home sits on.

• A golf-course setting on the Harbourside course, with the option of a private pool, fits how you want to live.

• A friendly, diverse, socially active community matters to your daily life.

• The deeded private Gulf beach and 24-hour gate are part of the lasting value you are looking for.

Why It Helps to Have a Broker on the Inside

Danielle lives inside Bay Isles and has been working this market since 1981 — she knows how Harbour Circle’s land-owned, maintenance-free structure actually works, which villas have private pools, and how the community sits on the golf course. That firsthand knowledge is the difference between assuming and knowing on a community this distinctive. Alison brings the other half: the analytical, villa-by-villa due-diligence discipline that keeps a purchase grounded in the documents rather than the brochure. Instinct and evidence, balancing each other completely.

A Private Conversation Costs Nothing

If Harbour Circle is the community you have your eye on — or you want a clear read on whether it fits you versus another part of Bay Isles — 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 villas are worth your time, how the land-owned structure works, 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 Harbour Circle in Bay Isles?

Harbour Circle at Longboat Key is a community of 42 contemporary Spanish-style villas at the north end of South Bay Isles, inside the gated Bay Isles community. Developed in the late 1980s, it consists mostly of three-bedroom, two-and-a-half-bath villas ranging from about 2,187 to 2,966 square feet, backing the Longboat Key Club’s Harbourside Golf Course.

How many homes are in Harbour Circle?

Harbour Circle has 42 villas, mostly three-bedroom, two-and-a-half-bath homes ranging from approximately 2,187 to 2,966 square feet. Its cohesive Spanish architectural style makes it one of the most visible and recognizable communities in Bay Isles.

Is Harbour Circle maintenance-free?

Yes — Harbour Circle is a maintenance-free community with a shared community pool and spa, but residents own the land their villa sits on. That land ownership is unusual within a maintenance-free structure and is why several homes also have private pools of their own.

Does Harbour Circle have golf course views?

Harbour Circle calls the Longboat Key Club’s Harbourside Golf Course its backyard, giving the community a golf-course setting with a distinctive architectural identity. Its prominent position is visible from both Gulf of Mexico Drive and Bay Isles Parkway.

What is the community like at Harbour Circle?

Harbour Circle is a very friendly community with residents of all ages and backgrounds, who gather for seasonal barbecues on the pool deck and organized holiday dinners at local restaurants. As part of Bay Isles, residents also have deeded access to the private Bay Isles Beach Club on the Gulf and the 24-hour guarded community gate.

Who is the best real estate agent for Harbour Circle in Bay Isles?

The best agent for Harbour Circle is one who can explain what an intimate villa community means for both resale and daily life: few units, infrequent turnover, and an association with a smaller reserve base carrying the same building systems as a larger one. That agent should compare the three-bedroom layouts candidly rather than treating them as interchangeable, and should be clear about what conveys inside the Bay Isles gates. Danielle Gladding & Co. Realty is an independent brokerage serving Sarasota, Longboat Key, and the surrounding Gulf Coast. Danielle Gladding lives in Queens Harbour inside Bay Isles, has been a licensed Florida Realtor since 1981 and a broker since 1987, and holds the Certified Waterfront Specialist and Certified Residential Listing Specialist designations.