Harbour Oaks Bay Isles | Danielle Gladding & Co. | Danielle Gladding & Co. Realty

Harbour Oaks is one of the earliest neighborhoods within Bay Isles, and it remains one of the best values behind the gate on a cost-per-square-foot basis. The villas here are substantial — three bedrooms, 2,100 square feet or more, with vaulted ceilings, skylights, and a private two-car garage — and thirty-nine of them back directly onto the Harbourside Golf Course, with open views from large terraces and, for many, private pools and spas.

I’m Danielle Gladding, of Danielle Gladding & Co. Realty, and I know Harbour Oaks from the inside — I live in Bay Isles, in Queens Harbour, and have been a Realtor since 1981 and a broker since 1987. With Alison Kanter, I help buyers understand where genuine value sits in a neighborhood like this. This is the accurate, resident’s guide.

Substantial Villas, Real Value

Harbour Oaks offers an array of styles and floor plans — single-story, two-story, and stacked villas — which gives buyers genuine choice. What they share is scale and quality: three bedrooms, 2,100 square feet or more of living space, vaulted ceilings, skylights, and a private two-car garage in every villa. On a cost-per-square-foot basis, Harbour Oaks is consistently one of the best values in Bay Isles and on Longboat Key, which is a large part of its enduring appeal.

On the Harbourside Golf Course

Thirty-nine of the Harbour Oaks villas back up to the Longboat Key Club’s Harbourside Golf Course, presenting beautiful open views from large terraces — and many of these homes have private pools and spas of their own. For buyers who want a golf-course outlook and outdoor living without the scale or upkeep of a single-family estate, this is a rare combination inside the gates.

A Settled, Social Community

Harbour Oaks has a community pool and spa, lush landscaping, and a location less than a mile from Longboat Key’s Town Center. The neighborhood’s Social Committee keeps it genuinely connected — beach parties, poolside gatherings, holiday celebrations, and destination dinners in the greater Sarasota area. And the community is remarkably stable: annual turnover averages less than 5%, with many original owners still in residence. That kind of long-term ownership tells you something real about how it feels to live here.

The Bay Isles Privileges Come Standard

Like every home inside the gates, a Harbour Oaks villa carries the shared Bay Isles privileges — deeded access to the private Bay Isles Beach Club on the Gulf at 2111 Gulf of Mexico Drive, and the 24-hour guarded community gate. A private Gulf beach and gated security, standard with a value-priced golf-course villa, is much of what makes Harbour Oaks so compelling.

The due diligence we walk every Harbour Oaks buyer through

Harbour Oaks is one of the earliest Bay Isles neighborhoods, so on any villa here we look closely at systems age, roof and exterior condition, and any planned capital work, alongside the association’s reserve study and assessment history. Whether a specific villa backs the golf course, and whether it has a private pool and spa, materially affects both value and carrying cost — so we confirm that lot by lot. Alison leads this scrutiny villa by villa, so you know exactly what you are buying.

Who Harbour Oaks Is Really For

After decades guiding buyers through Sarasota’s premier addresses, we find Harbour Oaks 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, 2,100+ square feet, vaulted ceilings, and a private two-car garage — at one of the best price-per-square-foot values in Bay Isles.

• A golf-course outlook matters, and a large terrace over the Harbourside course appeals to you.

• You would like the option of a private pool and spa without the scale of a single-family estate.

• A settled, social, low-turnover community with an active Social Committee fits how you want to live.

• 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 spent decades in this market — she knows which Harbour Oaks villas back the golf course, which have been updated, and how the neighborhood holds its value. On one of the earliest communities in Bay Isles, that firsthand knowledge is the difference between a good buy and an expensive surprise. 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 Oaks is the value 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, which back the golf course, 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 Oaks in Bay Isles?

Harbour Oaks is one of the earliest neighborhoods within the gated Bay Isles on Longboat Key, made up of single-story, two-story, and stacked villas. Each villa offers three bedrooms, 2,100 square feet or more, vaulted ceilings, skylights, and a private two-car garage, and is considered one of the best values in Bay Isles on a cost-per-square-foot basis.

Do Harbour Oaks villas have golf course views?

Thirty-nine of the Harbour Oaks villas back up to the Longboat Key Club’s Harbourside Golf Course, presenting open views from large terraces, and many of these homes have private pools and spas. The golf-course setting, combined with the value pricing, is a large part of the neighborhood’s appeal.

Do Harbour Oaks homes have private garages?

Yes — each Harbour Oaks villa includes a private two-car garage, along with three bedrooms and 2,100 square feet or more of living space. That combination of space, storage, and value is unusual inside a gated luxury community like Bay Isles.

Is Harbour Oaks a stable community?

Harbour Oaks is a notably stable, low-turnover community, with annual turnover averaging less than 5% and many original owners still in residence. Its Social Committee hosts beach parties, poolside gatherings, holiday celebrations, and destination dinners, giving the neighborhood a genuinely connected character.

What amenities does Harbour Oaks offer?

Harbour Oaks has a community pool and spa and lush landscaping, and sits less than a mile from Longboat Key’s Town Center. 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 a good real estate agent for Harbour Oaks in Bay Isles?

A good agent for Harbour Oaks is one who can explain how the single-story, two-story and stacked villa types differ on maintenance, resale and daily livability, because they are priced against each other and they should not be. That agent should be candid about what the vaulted-ceiling layouts require to update, and should be clear that the Bay Isles Beach Club conveys while a Longboat Key Club golf membership is a separate buy-in. 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.