Windward Passage Condos for Sale

Windward Passage: Waterfront Living Close to Siesta Key Village

by Hunt Brothers Realty

Windward Passage is a boutique waterfront condominium community at the north end of Siesta Key, offering expansive views across Big Pass while keeping Siesta Key Village close by. Located at 4708 and 4712 Ocean Boulevard, the community combines a relatively small number of residences with waterfront scenery, a heated pool, private balconies, garage parking, and convenient access to dining, shopping, beaches, and the north bridge to mainland Sarasota.

Current property information identifies approximately 22 residences in two buildings constructed in 1981. The community's position overlooking Big Pass creates views that can include the Gulf of Mexico, Lido Key, passing boats, and portions of the Sarasota skyline, depending on the individual residence.

For buyers exploring Windward Passage condos with Hunt Brothers Realty, the combination of waterfront living and proximity to Siesta Key Village is one of the community's most important distinctions.

Quick Answers About Windward Passage

Question	Quick Answer
Where is Windward Passage?	4708 and 4712 Ocean Boulevard at the northern end of Siesta Key in Sarasota, Florida
Is Windward Passage waterfront?	Yes. The property directly overlooks Big Pass and the Gulf waters at the north end of Siesta Key
How large is the community?	Current community sources identify approximately 22 residences in two buildings
When was Windward Passage built?	1981
Does Windward Passage have a pool?	Yes. Current community information identifies a heated waterfront swimming pool
Does Windward Passage have garages?	Yes. Current listings identify garage parking, including two-car garage arrangements with some residences
Is Siesta Key Village nearby?	Yes. Windward Passage is positioned just north of Siesta Key Village, making Village dining and shopping convenient from the community

Where Is Windward Passage on Siesta Key?

Windward Passage occupies a distinctive position along Ocean Boulevard at the northern end of Siesta Key. The two buildings are located at 4708 and 4712 Ocean Boulevard, where the island faces Big Pass.

Big Pass separates the northern end of Siesta Key from Lido Key and provides a broad waterfront setting with regular boating activity. Depending on the residence and orientation, views can extend across the water toward Lido Key and the Sarasota skyline.

The location also puts owners near the north end of Siesta Key Village and within convenient reach of the Siesta Drive bridge, an important consideration for buyers who expect to travel regularly between the island and mainland Sarasota.

Big Pass Is the Centerpiece of the Waterfront Setting

Windward Passage is defined by its relationship with Big Pass. Rather than looking across a narrow canal or interior bay, residences can have broad views across an active coastal waterway connecting Sarasota Bay with the Gulf of Mexico.

Boats moving through the pass become part of the scenery, while the position of Lido Key and mainland Sarasota creates a layered waterfront view. Current listings describe Gulf, Big Pass, Lido Key, and downtown Sarasota views from individual residences.

Views vary substantially according to building, floor, orientation, and the individual residence. Buyers who consider a particular view essential should evaluate it directly from the condo they are considering.

Siesta Key Village Is Close to Home

One of the strongest lifestyle advantages of Windward Passage is its proximity to Siesta Key Village.

Current community sources place the Village roughly half a mile from Windward Passage. That puts restaurants, shops, cafés, and other Village businesses close enough that walking or biking may be practical for some residents, depending on route, weather, mobility, and personal preference.

This creates an appealing contrast. Windward Passage sits at the quieter end of Ocean Boulevard overlooking the water, while the commercial activity of Siesta Key Village remains nearby.

A Heated Waterfront Pool Adds to the Setting

Windward Passage includes a heated community swimming pool positioned near the waterfront.

Landscaped grounds extend between the residential buildings and the water, creating an outdoor common area where the waterfront remains part of the experience even when residents are not inside their condos.

Amenity condition, operating rules, and availability can change. Buyers should verify current information with the condominium association when particular amenities are important to their purchasing decision.

What Are the Condos Like at Windward Passage?

Windward Passage is a comparatively small condominium community. Current community information identifies approximately 22 residences across two buildings constructed in 1981.

Typical residences have historically been described in the range of approximately 1,600 to 2,300 square feet, although individual properties can be larger. A current four-bedroom penthouse listing, for example, contains more than 3,900 square feet of interior living area. Buyers should therefore verify the recorded square footage and configuration of the particular condo rather than relying on a community-wide range.

Current and historical listings show two-bedroom, three-bedroom, and larger configurations. Private terraces or balconies are important features in many residences because they extend the living area toward the waterfront views.

Because the condos are individually owned, interior finishes and improvements vary. Kitchens, bathrooms, flooring, windows and doors, mechanical equipment, hurricane protection, and other improvements should be evaluated for the specific residence.

Private Balconies Put the Water Views Front and Center

Private outdoor space is particularly meaningful in a waterfront condominium, and Windward Passage residences are known for terraces or balconies oriented toward the surrounding views.

Current listings emphasize broad Gulf and Big Pass vistas from both living areas and outdoor spaces. Floor-to-ceiling sliders in some residences help connect interior rooms with the water outside.

Balcony dimensions, orientation, enclosure, railings, storm protection, and views vary by unit, so buyers should verify those details for the individual residence.

Garage Parking Is an Unusual Convenience for Island Condo Living

Current Windward Passage property information identifies garage parking, with multiple listings describing two-car garage arrangements associated with individual residences.

For condominium buyers, enclosed garage parking can matter for vehicle storage, convenience, and day-to-day use, particularly when comparing Windward Passage with properties offering only surface or carport parking.

Parking rights can be unit-specific. Buyers should verify the garage spaces legally associated with the residence, guest-parking provisions, vehicle restrictions, storage rights, and applicable association rules.

The North Bridge Makes Mainland Sarasota Convenient

Windward Passage's north Siesta Key location matters for more than proximity to the Village.

The Siesta Drive bridge provides the northern connection between Siesta Key and mainland Sarasota. Windward Passage is positioned conveniently for reaching that bridge without first traveling the length of Midnight Pass Road.

For owners who regularly travel to downtown Sarasota, mainland shopping, medical services, cultural destinations, or Sarasota Bradenton International Airport, access to the north bridge can be a practical consideration when comparing different parts of Siesta Key.

Beach Access Is Still Part of the Siesta Key Lifestyle

Windward Passage is primarily distinguished by its Big Pass waterfront setting, but owners remain close to Siesta Key's Gulf beaches.

Public beach access points are available elsewhere along the island, while Siesta Beach provides the larger public beach environment farther south.

Buyers should distinguish between waterfront frontage at Windward Passage and access to a traditional sandy Gulf beach. The community's primary waterfront experience is its position overlooking Big Pass.

A Smaller Community Creates a Different Condo Experience

With approximately 22 residences, Windward Passage is considerably smaller than many of Siesta Key's large condominium communities.

That scale affects both lifestyle and ownership. There are fewer residences sharing the property, but there are also fewer owners among whom common expenses may be allocated. The financial implications cannot be determined from unit count alone.

Buyers should evaluate the association budget, reserves, insurance, assessments, maintenance responsibilities, and capital plans rather than assuming that a smaller condominium necessarily means lower or higher ownership costs.

Who Might Put Windward Passage on Their Shortlist?

Windward Passage may deserve a closer look from buyers prioritizing:

Direct waterfront living on Big Pass
Expansive Gulf and water views from select residences
Proximity to Siesta Key Village
A smaller condominium community
Larger condominium floor plans
Private balconies or terraces
A heated waterfront swimming pool
Garage parking
Convenient access to the Siesta Drive bridge
Access to Siesta Key beaches, dining, and shopping

Waterfront Ownership Makes Due Diligence Important

The waterfront location that makes Windward Passage distinctive also makes property-specific due diligence particularly important.

Buyers should investigate current flood information, association insurance, unit-owner insurance, building condition, seawall and waterfront components, roofs, windows and doors where applicable, elevators, reserves, assessments, completed capital projects, anticipated work, and any structural inspection or reserve information applicable to the condominium.

The original 1981 construction date does not establish the present condition of either building or an individual residence. Renovations, maintenance histories, storm-related improvements, structural work, and building systems can differ considerably over time.

Inspection findings, structural conditions, waterfront components, flood exposure, and anticipated repairs should be evaluated using current property-specific information. Buyers should involve the appropriate licensed inspector, structural engineer, contractor, insurance professional, association representative, or other qualified specialist when individualized evaluation is necessary.

Insurance and Flood Information Should Be Evaluated Before Purchasing

Insurance is an important part of evaluating a condominium directly on a coastal waterway.

Buyers should review available association insurance information and understand how the master policy relates to coverage needed for the individual residence. Improvements, personal property, intended occupancy, and rental use can also affect insurance needs.

Insurance availability, coverage, exclusions, deductibles, premiums, and flood considerations can vary substantially by property. Buyers should obtain property-specific quotes and review coverage with a qualified insurance professional before making a purchasing decision.

Review the Condo Budget, Reserves, and Assessments

The view from a Windward Passage condo may be what first captures a buyer's attention, but association finances deserve equal scrutiny before a purchase.

Buyers should review current assessments and what they include, the condominium budget, reserve information, insurance, current or contemplated special assessments, completed capital projects, anticipated work, governing documents, and meeting records.

Florida condominium requirements have changed in recent years, and which requirements apply depends on property-specific facts. Buyers should rely on current Windward Passage documents rather than assumptions based on another Siesta Key condominium.

For additional background, read How to Read a Condo Budget Before Purchasing. Accounting, reserve, legal, insurance, structural, and association questions should be reviewed with the appropriate qualified professionals before they become the basis of a purchasing decision.

Rental and Pet Rules Need Current Verification

Public sources currently conflict on some Windward Passage rental and pet details. Some market sources report a six-month minimum lease and limited leasing frequency, while other online community information reports different restrictions.

The same issue appears with pet policies, where publicly available descriptions are not consistent. Those differences make current association documents especially important.

Buyers should obtain the current declaration, rules, amendments, application materials, and association confirmation before relying on rental or pet rights. If intended rental use materially affects the purchase, legal, tax, lending, insurance, licensing, and financial questions should also be reviewed with the appropriate qualified professionals.

Windward Passage Compared with Other Siesta Key Condos

Windward Passage occupies a different niche from many of Siesta Key's larger beachfront condominium communities.

Its approximately 22 residences create a smaller setting. Big Pass provides the waterfront backdrop. Siesta Key Village is close by, and the north bridge makes mainland access convenient. Individual residences can also be considerably larger than condos found in some of the island's more compact developments.

Other Siesta Key communities may offer larger resort amenity packages, direct sandy beachfront settings, boating facilities, shorter rental periods, or different ownership structures. The right comparison depends on the features that matter to the individual buyer.

For a practical framework, read How to Compare Two Sarasota Condo Buildings from Hunt Brothers Realty.

Questions to Ask When Touring a Windward Passage Condo

What water views does this particular residence have?
How does the floor and building position affect the view?
What renovations have been completed inside the condo?
What hurricane protection is installed?
What garage, parking, and storage rights accompany the residence?
What are the current condominium assessments and what do they include?
What do the current budget and reserve information show?
Are there current or contemplated special assessments?
What major building projects have recently been completed?
What capital projects are planned or being discussed?
What are the current rental restrictions?
What pet rules currently apply?
What insurance and flood information applies to the building and individual residence?
What applicable inspection, engineering, or reserve information is available?

Is Windward Passage Right for You?

Windward Passage combines several characteristics that do not always appear together in a Siesta Key condominium.

The property has direct Big Pass frontage, a heated waterfront pool, a relatively small number of residences, private outdoor spaces, garage parking, and convenient access to Siesta Key Village. Its north-island position also makes the Siesta Drive bridge readily accessible for trips to mainland Sarasota.

For buyers who prioritize broad water views and proximity to Village dining and shopping over a large resort-style amenity package, those characteristics can make Windward Passage particularly worth comparing with other Siesta Key options.

The final decision should depend on the specific residence, its views and condition, current association finances, insurance, flood considerations, ownership costs, parking rights, rules, and how closely the property matches the way you intend to use a Siesta Key home.

Explore Windward Passage Condos with Hunt Brothers Realty

If Big Pass views, larger condominium residences, and proximity to Siesta Key Village put Windward Passage on your shortlist, explore Windward Passage with Hunt Brothers Realty. We can help you evaluate current listings, individual residence characteristics, market activity, and how the community compares with other Siesta Key waterfront properties from a real estate perspective.

You can also explore Sarasota-area communities with Hunt Brothers Realty while comparing beachfront, waterfront, boating, and Village-area condominium options on Siesta Key.

Informational notice: This article provides general real estate and educational information only. It is not individualized legal, financial, tax, insurance, lending, inspection, engineering, construction, flood, title, association, rental, or other professional advice. Condominium rules, rental restrictions, pet policies, assessments, reserves, insurance, flood information, structural conditions, amenities, parking rights, views, and ownership costs can change and vary by residence. Buyers should verify current property-specific information and consult the appropriate qualified real estate professional, lender, insurance agent, Florida real estate attorney, tax professional, inspector, structural engineer, contractor, title professional, condominium association, or other qualified specialist before making a decision requiring individualized guidance.