The Landings Racquet Club entrance sign beside a landscaped canal and residences.

Oyster Bay, The Landings & South West of the Trail

Oyster Bay, The Landings and the neighborhoods south of Sarasota’s traditional West of Trail corridor offer an established residential setting between Sarasota Bay, Roberts Bay and Tamiami Trail. The area combines waterfront estates, large interior homesites, gated communities, mid-century homes and increasingly sophisticated new construction, with convenient access to Siesta Key, The Field Club, Southside Village, downtown Sarasota, Sarasota Memorial Hospital and nearby shopping and dining.

Oyster Bay, The Landings & South West of the Trail

Established Sarasota Living Between the Bay and Siesta Key

South of Sarasota’s better-known in-town West of Trail neighborhoods, the residential landscape becomes broader, greener and, in many places, more private.

This larger area includes Oyster Bay, The Landings and a collection of smaller subdivisions west of South Tamiami Trail, including portions of Field Club Estates, South Highland, Johnson Estates, Kentwood Estates and surrounding streets. Rather than functioning as one unified neighborhood, these communities form a connected residential corridor where buyers often compare properties across subdivision lines.

What ties them together is location.

Siesta Key sits only minutes to the west, downtown Sarasota and Southside Village are easily reached to the north, and everyday conveniences are unusually close. The Landings Shopping Center provides groceries, restaurants and neighborhood services, while Sarasota Memorial Hospital, Trader Joe’s, Walt’s Fish Market and other established Sarasota destinations are within a short drive.

That range is one of the area’s greatest strengths.

702

Residences in The Landings

280

Acres in The Landings

1925

Field estate construction begins

1957

Estate becomes The Field Club

0.78 acre

Direct-bay Red Rock Way example

Why Buyers Love Oyster Bay, The Landings & South West of the Trail

Space and privacy, close to the city.

This part of Sarasota appeals to buyers who want space and privacy without moving far from the city.

Homesites are often larger than those found closer to downtown, mature trees remain an important part of the landscape, and many streets feel distinctly residential. Yet Siesta Key, Southside Village, Sarasota Memorial Hospital, downtown Sarasota and everyday shopping remain close.

Architectural diversity adds another advantage. Buyers can choose an original mid-century home and renovate it, purchase a completely reimagined residence, build new on an established lot, or seek out a larger custom property that already reflects contemporary Sarasota living.

Oyster Bay adds the prestige and visual character of an established neighborhood organized around water and The Field Club. The Landings offers something different: controlled access, winding private streets, preserved natural areas and an optional racquet-club lifestyle.

The surrounding South West of Trail streets fill in the space between them, often without the uniformity or restrictions of a master-planned community.

For waterfront buyers, the possibilities are equally varied. Sarasota Bay frontage, tidal waterways, canals and interior lakes can all appear within the broader area, creating very different relationships with the water.

The common thread is location: a mature residential corridor positioned remarkably close to both Sarasota’s urban conveniences and Siesta Key.

Siesta KeySouthside VillageThe Field ClubThe Landings

The Story Behind Oyster Bay, The Landings & South West of the Trail

A history that predates its neighborhoods.

The history of this area predates most of its present-day neighborhoods.

1920s to 1957

The Field Estate

During the 1920s, Stanley and Sara Field established their winter estate along Roberts Bay. Architect David Adler designed the property as a substantial waterfront “great house,” incorporating the bay and surrounding landscape into the estate. Construction began in 1925 and was completed two years later.

In 1957, the Field property was purchased by a group of Sarasota residents and transformed into the private Field Club rather than being subdivided for residential development. The estate remains one of the area’s most important architectural and historical landmarks.

Postwar to Today

Neighborhoods Take Shape

Oyster Bay Estates began developing around this established landscape during the early postwar period. Its curving street pattern, lakes and waterfront sites reflect a different era of Sarasota planning than the rigid grids found in many older neighborhoods.

The Landings arrived later and introduced a more comprehensively planned model. Its gated road network, residential enclaves, mangrove preserves and recreational facilities created a community that feels much more self-contained than Oyster Bay or the surrounding West of Trail streets.

Meanwhile, neighborhoods such as South Highland, Field Club Estates, Johnson Estates and Kentwood continued to evolve individually. Older cottages and ranch homes remain, but renovation and redevelopment have steadily introduced larger contemporary properties.

That ongoing evolution is now one of the defining characteristics of South West of the Trail: historic Sarasota estates, postwar neighborhoods, gated communities, waterfront properties and modern architecture all coexist within the same remarkably well-located residential corridor.

Homes & Amenities

Several generations of Sarasota residential development.

The housing throughout Oyster Bay, The Landings and the broader South West of the Trail area reflects several generations of Sarasota residential development. The area includes:

Florida ranch homes

Mid-century residences

Traditional estates

Coastal cottages

Extensively renovated older homes

Contemporary custom construction

Waterfront estates

Villas and townhomes within The Landings

Example	Setting	Details
Restored 1950s cottage	South Highland	Approximately 1,000 sq. ft. on a compact homesite
Newly completed custom contemporary home	South Highland	Exceeding 3,000 sq. ft.
2025 residence	Kentwood Estates	Approximately 0.45 acre with nearly 4,000 sq. ft. of living area and a four-car garage
Red Rock Way property	Direct Sarasota Bay	Approximately 0.78 acre directly on Sarasota Bay
The Landings	Gated community	Approximately 280 acres and 702 residences, including detached homes, villas and townhomes

Representative examples drawn from within the area.

Architecture

Postwar Homes to Contemporary Construction

The architecture is equally varied. Original postwar homes and Florida ranches remain throughout the area, alongside renovated mid-century residences, traditional estates, coastal architecture and substantial contemporary construction. In South Highland, for example, a restored 1950s cottage may sit only blocks from a newly completed custom contemporary home exceeding 3,000 square feet.

Established Neighborhood

Oyster Bay

Oyster Bay illustrates this evolution particularly well. Residential development began in the early 1950s, and the neighborhood now contains everything from older ranch homes and renovated cottages to large modern estates. The original Oyster Bay Estates plat also reveals the neighborhood’s distinctive planning around curving streets, freshwater lakes, a yacht basin and Sarasota Bay rather than a simple rectangular street grid. Some Oyster Bay properties occupy substantial interior lots beneath mature trees. Others front lakes, tidal waterways or Sarasota Bay itself. The differences can be considerable, which means waterfront orientation, water depth, bridges, dockage and seawall condition should always be evaluated for the individual property.

Historic Landmark

The Field Club

The neighborhood’s relationship with The Field Club is another defining element. The club occupies the former winter estate of Stanley and Sara Field, designed by noted Chicago architect David Adler and built beginning in 1925. The estate became The Field Club in 1957 and was later placed on the National Register of Historic Places. The Field Club remains a separate private organization, however. Ownership in Oyster Bay or the surrounding neighborhoods does not automatically include club membership.

Guard-Gated Community

The Landings

Immediately to the south, The Landings offers a very different version of West of Trail living. The gated community encompasses approximately 280 acres and 702 residences, including detached homes, villas and townhomes, with winding streets, mature landscaping, nature preserves and extensive mangrove areas. Unlike the surrounding open neighborhoods, The Landings is controlled through guarded entrances and private roads. Tree canopies, larger homesites, cul-de-sacs and landscaped streets give the community a more secluded character despite its position directly beside shopping, restaurants and Tamiami Trail.

Nature

Nature at The Landings

Nature is an unusually important part of the experience. Walking trails extend toward Roberts Bay and the Intracoastal Waterway, with community features that include a fishing pier, kayak launch, gazebo, butterfly garden and preserved mangrove habitat.

Optional Membership

The Landings Racquet Club

An optional membership to The Landings Racquet Club adds tennis, pickleball, swimming, fitness and social facilities. Current property information describes eight Har-Tru tennis courts, a heated pool, fitness facilities and clubhouse amenities, although club offerings and membership terms should be confirmed directly.

Broader Area

South West of the Trail

Outside Oyster Bay and The Landings, the broader South West of the Trail area becomes even more eclectic. Along streets such as Field Road, Kenilworth Street, Worrington Street, Camino Real and Red Rock, buyers encounter smaller cottages, large estate lots, renovated mid-century houses, contemporary custom homes, guesthouses and occasional direct-bay properties.

Range of Sizes

From Compact Cottages to Bayfront Sites

The size variation can be striking. A South Highland cottage may occupy approximately 1,000 square feet on a compact homesite, while nearby Field Club Estates and Oyster Bay properties can sit on parcels approaching half an acre or more. At the water’s edge, the scale expands further: a Red Rock Way property occupies approximately 0.78 acre directly on Sarasota Bay, illustrating the large bayfront sites that can still be found within this southern West of Trail corridor. Buyers are not choosing among variations of the same house or development. They may be comparing a mid-century ranch, a renovated cottage, a contemporary estate, a gated Landings residence or a direct-bay property within only a few minutes of one another.

Homes Across Generations

In Oyster Bay and surrounding subdivisions, buyers may encounter original Florida ranch homes, remodeled mid-century residences, traditional estates, coastal cottages and increasingly substantial contemporary construction. Homesites also vary considerably, from compact interior parcels to lots approaching half an acre or more. Oyster Bay Estates includes both interior and waterfront settings, while nearby Field Club Estates, South Highland, Johnson Estates and Kentwood contribute additional variety in lot size, architecture and age.

That variety creates very different ownership opportunities. An older home may appeal because of its mature landscaping, larger lot and renovation potential, while newer construction may offer impact glass, current building standards, open interiors, larger garages, outdoor kitchens and integrated pool areas. A fully reimagined Oyster Bay residence, for example, can bear little resemblance to its original postwar configuration, while new homes continue to appear on established neighborhood streets.

Pools and outdoor living are common throughout the area. Screened lanais, covered terraces, outdoor kitchens, guesthouses, courtyards and mature tropical gardens appear frequently, particularly on larger properties.

Waterfront Homes

Waterfront homes introduce another level of property-specific analysis. Depending on location, a residence may front Sarasota Bay, a canal, lagoon, lake or other connected waterway. Private docks are found with select properties, but boating conditions can vary significantly by water depth, bridge clearance, dock configuration and route to open water. Large direct-bay parcels also exist, including properties with substantial Sarasota Bay frontage.

The Landings: Nature & Recreation

The Landings offers a more structured ownership environment. Its approximately 702 residences include detached homes, villas and townhomes within a guard-gated setting of winding private streets, mature landscaping and preserved natural areas. The Racquet Club is optional rather than automatically included with every residence, and current offerings, dues and membership terms should be confirmed directly with the club.

Guard-gated entrances

Private roads

Nature preserves

Extensive mangrove areas

Walking trails toward Roberts Bay and the Intracoastal Waterway

Fishing pier

Kayak launch

Gazebo

Butterfly garden

Optional Racquet Club: eight Har-Tru tennis courts

Optional Racquet Club: heated pool, pickleball and fitness

Optional Racquet Club: clubhouse amenities

Homes in The Landings

Single-family homes in The Landings frequently feature private pools, screened lanais, two- or three-car garages, courtyards and mature landscaping. Architecture varies from original 1980s Florida designs to extensively renovated homes and later custom construction.

Outside The Landings

For residents outside The Landings, the broader neighborhood itself provides much of the lifestyle. The Field Club, Landings Shopping Center, Siesta Key, Southside Village, Sarasota Memorial Hospital and downtown Sarasota are all nearby, while the surrounding residential streets remain considerably quieter than Sarasota’s urban core.

Lifestyle Policies

What to know before you buy.

Because this guide combines several separate subdivisions and communities, there is no single set of ownership rules applying throughout the area.

Pets	Generally property- or association-specific; The Landings and individual subdivisions may have their own rules
Leasing	Varies by subdivision and property; Sarasota County regulations and applicable association documents should be reviewed
Association Structure	Varies significantly; The Landings has mandatory community governance, while surrounding neighborhoods may have optional, mandatory or no association depending on the subdivision
Buyer Approval	Required in certain communities, including The Landings
Parking	Primarily private driveways and garages for single-family homes; villas and townhomes may have community-specific arrangements
Renovations / Construction	Subject to applicable association requirements, deed restrictions, Sarasota County permitting and zoning
Exterior Changes	Property- and association-specific
Waterfront Improvements	Docks, lifts, seawalls and other improvements are subject to property rights and applicable governmental permitting
Racquet Club Membership	Optional at The Landings
Security	The Landings is guard-gated; surrounding Oyster Bay and South West of Trail neighborhoods generally have different access arrangements

Association rules, fees, services, pet policies, leasing restrictions, construction procedures, and amenity operations may change. Buyers should verify all current information directly with the Association and any applicable governmental authority.

The distinction between subdivisions is important. Oyster Bay East, for example, has its own required association structure and maintenance provisions, while other Oyster Bay properties may have optional or different association arrangements.

Frequently Asked Questions

Everything buyers ask us first.

Where are Oyster Bay, The Landings & South West of the Trail?

They are located west of South Tamiami Trail in south Sarasota, generally between Sarasota Bay and Roberts Bay to the west and Tamiami Trail to the east. The area sits south of Sarasota’s traditional in-town West of Trail neighborhoods and north of the Stickney Point Road corridor.

Are Oyster Bay and The Landings the same community?

No. Oyster Bay is an established collection of residential subdivisions and streets centered around The Field Club and Sarasota Bay. The Landings is a separate, guard-gated residential community immediately to the south, with private roads, common natural areas and its own association structure.

What is meant by “South West of the Trail”?

For this guide, the term refers to the broader collection of residential neighborhoods west of South Tamiami Trail surrounding Oyster Bay and The Landings, including areas such as South Highland, Field Club Estates, Johnson Estates and Kentwood Estates. It is a geographic grouping rather than one formal subdivision.

What types of homes are available?

The area includes Florida ranch homes, mid-century residences, traditional estates, coastal cottages, extensively renovated older homes, contemporary custom construction, waterfront estates, and villas and townhomes within The Landings.

Are there newer homes?

Yes. Redevelopment and infill construction have introduced substantial new contemporary homes throughout Oyster Bay and the surrounding West of Trail streets. A 2025 Kentwood Estates residence, for example, was built on approximately 0.45 acre with nearly 4,000 square feet of living area and a four-car garage, illustrating the scale of some newer construction in the area.

Are there large lots?

Yes. Lot sizes vary significantly, but many established properties occupy approximately one-quarter to one-half acre, with some waterfront and estate properties larger still. Field Club Estates and Oyster Bay include especially notable examples of larger residential parcels.

Are there waterfront homes?

Yes. Select properties offer direct Sarasota Bay frontage, while others may face canals, lagoons, interior lakes or connected waterways. Waterfront characteristics should always be investigated for the individual property.

Can homeowners have private docks?

Some waterfront properties have private docks or other boating improvements. Dock rights, water depth, seawall condition, bridge clearances and permitting should be evaluated individually because conditions vary significantly throughout the area.

Does The Landings have boat docks?

The Landings provides waterfront access through its nature-trail area, including a fishing pier and kayak launch, but it should not be treated as a conventional marina community with individual boat slips for every residence.

What amenities are available in The Landings?

The Landings provides a guard-gated environment, private streets, preserved natural areas, walking trails, kayak access and a fishing pier. Optional membership at The Landings Racquet Club adds recreational amenities including tennis, pickleball, swimming, fitness and clubhouse facilities.

Is Landings Racquet Club membership required?

No. Membership is optional and separate from basic residential ownership within The Landings.

What is The Field Club?

The Field Club is a private Sarasota club located on a historic waterfront estate within the Oyster Bay area. Its presence is an important part of the neighborhood’s identity, but club membership is separate from homeownership and should not be assumed to accompany a property.

Are there homeowners associations?

It depends entirely on the property. The Landings has a mandatory association structure and controlled access. Certain smaller Oyster Bay subdivisions also have their own associations, while some surrounding neighborhoods have optional associations or no mandatory HOA.

Are rentals permitted?

Rental eligibility varies by subdivision, association and property. Buyers planning rental use should verify the applicable deed restrictions, association rules and Sarasota County regulations before purchasing.

How close is Siesta Key?

Very close. The north and south Siesta Key access routes are only minutes from much of this area, making Siesta Beach and Siesta Key Village readily accessible.

What shopping and dining are nearby?

The Landings Shopping Center is immediately adjacent to the area and includes grocery, dining and neighborhood services. South Tamiami Trail offers additional shopping and restaurants, while Southside Village and downtown Sarasota are a short drive north.

Does The Landings have an official website?

Yes. The Landings of Sarasota is at thelandingsofsarasota.com.

While we make every effort to keep our Community Guides current, association structures, fees, deed restrictions, pet policies, leasing rules, security procedures, club memberships, waterfront rights, dock regulations and municipal requirements may change over time.

Because Oyster Bay, The Landings and South West of the Trail encompass numerous subdivisions and individually governed properties, buyers and sellers should verify all information applicable to the specific property, including association obligations, zoning, flood designation, dock and seawall rights, leasing requirements and construction restrictions, during their due-diligence period.

Buying in Oyster Bay, The Landings & South West of the Trail

Find your home.

Every Oyster Bay, The Landings and South West of the Trail property offers a different ownership experience.

Here, buyers should compare more than architecture and square footage. Subdivision, lot size, renovation history, elevation, flood designation, association structure, garage capacity, outdoor living and proximity to the water can all materially affect both lifestyle and value.

For waterfront properties, the evaluation becomes even more specific. Water depth, dock configuration, seawall condition, bridge clearance and access to Sarasota Bay or Roberts Bay may be just as important as the house itself.

Older homes require a different analysis. Some have been comprehensively renovated, while others retain original systems or layouts and may offer redevelopment potential. Newer construction can introduce modern building standards and larger floor plans but may sit on smaller or differently configured sites.

The Landings adds another set of considerations, including association approval, security, private roads, optional Racquet Club membership and location within the community.

With more than four decades of local experience, Pettingell Professionals helps buyers understand these distinctions and evaluate each property within the broader Sarasota luxury market.

Selling Your Oyster Bay, The Landings & South West of the Trail Home

Tell your home's story.

Today’s luxury buyers begin their search long before they schedule a showing. They compare communities, study neighborhood maps, evaluate locations, and look for reliable information about the details that affect ownership.

That’s why we’ve created one of Sarasota’s most comprehensive luxury condominium and residential community guides.

Our goal is simple. When someone searches for Oyster Bay, The Landings or South West of the Trail, we want them to find the most accurate, informative, and complete resource available. More importantly, we want your home to be part of that discovery.

For sellers, this matters because properties throughout this area can be remarkably different. A home may distinguish itself through direct bay frontage, an oversized homesite, private dock, architectural character, a major renovation, newer construction, proximity to The Field Club, or a particularly desirable location within The Landings.

Those distinctions deserve to be explained rather than reduced to bedroom count and square footage.

Combined with exceptional photography, aerial imagery when appropriate, cinematic video, strategic digital marketing, and more than four decades of experience representing Sarasota and Longboat Key’s finest properties, we position your home where today’s luxury buyers begin their search.

The Pettingell Community Guides

Exceptional real estate decisions begin with exceptional information.

The Pettingell Community Guides were created to provide buyers and sellers with accurate, objective, and thoughtfully researched information about Sarasota and Longboat Key’s most exceptional condominium communities, residential neighborhoods, and waterfront enclaves. Every guide is independently researched, regularly updated, and written to help you understand not only the facts about a community, but also the history, lifestyle, architecture, and details that make it unique. Rather than relying on marketing language or generic descriptions, our goal is to create the most complete and trustworthy resource available for each community we cover.

Whether you’re buying, selling, or simply exploring Sarasota’s luxury real estate market, we hope these guides help you make more informed decisions and discover the communities that best fit your lifestyle.