Oyster Bay Landings Sarasota is an exclusive gated waterfront community located within the prestigious West of the Trail area of Sarasota, Florida. Tucked away along Rebecca Lane and Kenilworth Street near Roberts Bay, this intimate neighborhood features just 14 original homesites, custom luxury residences, and private boating opportunities. Its landscaped entrance, brick-paved street, waterfront surroundings, and proximity to The Field Club create a distinctive residential setting near some of Sarasota’s most desirable coastal destinations.
Unlike larger master-planned communities, Oyster Bay Landings was developed as a boutique enclave where individual homeowners could create custom residences suited to their preferences. Architectural styles range from traditional coastal and West Indies-inspired estates to contemporary waterfront designs. Many homesites offer deeded docking privileges along protected waterways connecting to Roberts Bay and the Intracoastal Waterway. With convenient access to Siesta Key, shopping, restaurants, and Downtown Sarasota, Oyster Bay Landings combines waterfront privacy with a central Sarasota location.
Oyster Bay Landings Luxury Homes & Estates
Oyster Bay Landings consists of a limited collection of custom luxury homes and residential homesites. Unlike subdivisions with standardized builder floor plans, properties throughout the neighborhood reflect individual architectural designs, construction periods, and homeowner preferences.
The community includes waterfront estates featuring expansive living areas, private outdoor retreats, landscaped courtyards, and boating facilities. Home sizes and configurations vary considerably, with some custom residences offering more than 4,000 square feet of living space.
Depending on the individual property, features may include:
- Custom three-, four-, and five-bedroom floor plans
- Single-story and multilevel luxury residences
- Open-concept living and dining areas
- Expansive great rooms and entertaining spaces
- Gourmet kitchens with premium appliances
- Generous primary bedroom suites
- Home offices, studies, and bonus rooms
- High ceilings and custom architectural details
- Floor-to-ceiling windows and expansive glass doors
- Private courtyard swimming pools and spas
- Covered lanais and outdoor kitchens
- Multiple-car garages
- Custom landscaping and private gardens
- Waterfront terraces and outdoor entertaining areas
- Deeded dock slips associated with individual homesites
- Smart home technology and hurricane protection in select properties
Because construction and design vary throughout the community, buyers should evaluate individual floor plans, building materials, storm protection, renovation histories, and waterfront improvements when comparing available properties.
Custom Architecture & Modern Waterfront Designs
Oyster Bay Landings features an attractive mixture of architectural styles rather than a uniform collection of homes.
Traditional residences may feature West Indies-inspired architecture, tile roofs, landscaped courtyards, and covered outdoor living areas. Other properties showcase contemporary architecture with clean lines, expansive windows, and open interior layouts.
One notable example is a contemporary residence at 1401 Kenilworth Street, designed by Sarasota architectural firm Sweet Sparkman and completed in 2024. The home incorporates extensive glass, modern architectural lines, and a design emphasizing natural light and connections to the surrounding landscape.
This architectural variety contributes to Oyster Bay Landings’ appeal among buyers seeking distinctive custom construction in an established waterfront location.
Private Pools, Courtyards & Outdoor Living
Many Oyster Bay Landings residences are designed around outdoor living. Private swimming pools, spas, landscaped courtyards, and covered entertaining areas allow homeowners to enjoy Sarasota’s coastal climate throughout the year.
Select properties include expansive sliding glass doors that connect interior gathering spaces with outdoor terraces and pool areas.
Other homes feature tropical gardens, decorative fountains, outdoor kitchens, and private seating areas.
Because the community contains individually designed residences, these features vary by property and are not shared neighborhood amenities.
Oyster Bay Landings Waterfront & Boating Amenities
One of Oyster Bay Landings’ greatest attractions is its protected waterfront setting and availability of deeded boating privileges. The community was developed with an emphasis on convenient access to Roberts Bay and Sarasota’s surrounding waterways.
Neighborhood features include:
- Private gated community entrance
- Just 14 original residential homesites
- Brick-paved residential street
- Custom luxury waterfront residences
- Deeded boat dock privileges associated with homesites
- Protected canal and cove frontage
- Access to Roberts Bay and the Intracoastal Waterway
- Private docks and boat lifts on select properties
- Mature tropical landscaping
- Attractive waterfront surroundings
- Homeowners association governance
- Convenient proximity to The Field Club
- Nearby shopping, dining, and Gulf Coast beaches
Deeded Boat Slips & Roberts Bay Access
Oyster Bay Landings is especially appealing to buyers interested in waterfront ownership and recreational boating.
Property listings have described deeded boat slips associated with individual homesites, including docks equipped with utilities such as electricity and water.
The protected waterways connect with Roberts Bay and the Intracoastal Waterway, allowing boaters to explore Sarasota’s coastal destinations.
However, docking arrangements and navigational conditions should be evaluated individually. Buyers should verify:
- Whether a deeded dock or slip transfers with the property
- Dock location and ownership documentation
- Boat length, beam, and draft limitations
- Water depth and tidal conditions
- Bridge clearance and navigational routes
- Boat lift capacity and permits
- Dock utility connections
- Seawall and waterfront maintenance responsibilities
- Association regulations and insurance requirements
- Any additional docking or marina-related expenses
Although the neighborhood is known for its boating facilities, buyers should not assume every dock accommodates large yachts or that all slips have identical dimensions and water depths.
Private Gated Entrance & Landscaped Setting
Oyster Bay Landings provides controlled access through its private gated entrance, distinguishing it from the surrounding Oyster Bay Estates neighborhood.
Brick-paved streets, mature trees, and established tropical landscaping contribute to the neighborhood’s intimate residential atmosphere.
The limited number of homesites also creates a quieter environment than many larger residential developments.
Oyster Bay Landings HOA Fees & Ownership Considerations
Oyster Bay Landings is a deed-restricted single-family residential community with homeowners association governance.
Association assessments support designated shared community expenses, which may include:
- Private entrance gate maintenance
- Common-area landscaping
- Private road and entrance maintenance
- Shared waterfront improvements where applicable
- Association management
- Common-area insurance
- Reserve funding and designated operating expenses
Unlike condominium ownership, individual homeowners generally remain responsible for their residences, roofs, landscaping, swimming pools, docks, seawalls, and other private improvements, subject to the property’s governing documents.
Buyers should review current HOA assessments, architectural restrictions, reserve funding, waterfront responsibilities, insurance requirements, rental regulations, and any planned neighborhood improvements.
Waterfront Property Considerations
Purchasing a custom waterfront home involves additional considerations beyond those associated with a traditional inland property.
Prospective buyers should evaluate:
- Flood zone designations and flood insurance requirements
- Windstorm insurance and hurricane protection
- Seawall condition and maintenance obligations
- Dock and boat lift inspections
- Waterfront erosion and drainage conditions
- Marine construction permits
- Property elevation and building design
- Roof condition and major mechanical systems
- HOA architectural approval procedures
- Property taxes and applicable assessments
For newer homes, buyers should also review construction permits, warranties, impact protection, and the scope of completed improvements.
Oyster Bay Landings Sarasota Location
Oyster Bay Landings is located along Rebecca Lane and Kenilworth Street in Sarasota’s 34231 ZIP code, west of South Tamiami Trail near Roberts Bay.
The community forms a gated enclave within the larger Oyster Bay Estates area, which is known for its custom waterfront homes, established landscaping, and desirable West of the Trail setting.
One of the neighborhood’s advantages is its proximity to The Field Club, a private waterfront social, tennis, and boating club located nearby.
The Field Club offers eligible members recreational and social amenities, including marina facilities, tennis, swimming, dining, and organized activities. Club membership is separate from Oyster Bay Landings homeownership and is not automatically included with a property purchase.
Nearby South Tamiami Trail offers grocery stores, restaurants, pharmacies, specialty retailers, and everyday conveniences.
The neighborhood is also convenient to Southside Village and Sarasota Memorial Hospital, while Downtown Sarasota provides additional cultural attractions, waterfront dining, theaters, and entertainment.
Nearby Beaches, Parks & Attractions
Oyster Bay Landings residents enjoy convenient access to waterfront recreation, parks, shopping, cultural attractions, and Sarasota’s Gulf Coast beaches.
The Field Club is a historic private waterfront club located near the community. Eligible members have access to boating, tennis, swimming, dining, and social opportunities, subject to membership requirements.
Phillippi Estate Park offers waterfront views along Phillippi Creek, historic buildings, landscaped grounds, walking areas, and community events.
Siesta Key is known for its white quartz-sand beaches, Gulf sunsets, waterfront recreation, and the shops and restaurants of Siesta Key Village.
Southside Village features neighborhood restaurants, cafés, specialty shops, and convenient services near Sarasota Memorial Hospital.
Marie Selby Botanical Gardens offers waterfront botanical collections, tropical gardens, exhibitions, and cultural events.
Downtown Sarasota features theaters, art galleries, museums, waterfront parks, restaurants, and entertainment.
Lido Key offers Gulf beaches, coastal recreation, and convenient access to the shopping and dining destinations of St. Armands Circle.
Travel times depend on traffic, bridge conditions, and seasonal visitor activity.
Similar West of the Trail Waterfront Communities
Buyers interested in Oyster Bay Landings may also want to explore other established Sarasota neighborhoods offering custom luxury homes, waterfront opportunities, boating access, and desirable locations near Sarasota Bay.
- Oyster Bay Estates – The surrounding West of the Trail neighborhood featuring custom waterfront estates, established residences, and homes overlooking Roberts Bay and interior waterways.
- San Remo Estates – An established luxury waterfront neighborhood offering custom homes, private docks, and access to Sarasota’s coastal waterways.
- Harbor Acres – A prestigious Sarasota neighborhood featuring custom waterfront estates, mature landscaping, and convenient access to Downtown Sarasota.
- Southpointe Shores – A waterfront residential neighborhood offering luxury homes, private boating facilities, and access to Little Sarasota Bay.
- Coral Cove – An established coastal neighborhood featuring waterfront and interior residences near Little Sarasota Bay and southern Sarasota attractions.
Oyster Bay Landings Homes for Sale | Sarasota Florida
Explore available Oyster Bay Landings homes for sale in Sarasota, Florida, including custom luxury waterfront estates, contemporary residences, and occasional residential homesites with deeded boating privileges.
With just 14 original homesites, Oyster Bay Landings offers a limited number of resale and individual construction opportunities. Available properties may vary significantly in architectural style, square footage, waterfront features, dock configurations, and interior finishes.
The MLS listings below provide current property details, photographs, pricing, and availability. Buyers should compare HOA regulations, dock rights, navigational access, seawall condition, insurance requirements, and property-specific improvements when evaluating available homes.
Frequently Asked Questions About Oyster Bay Landings Sarasota
Where is Oyster Bay Landings located in Sarasota?
Oyster Bay Landings is located along Rebecca Lane and Kenilworth Street in Sarasota’s 34231 ZIP code, within the West of the Trail area near Roberts Bay and The Field Club. The gated neighborhood is convenient to Siesta Key and Downtown Sarasota.
Is Oyster Bay Landings a gated community?
Yes. Oyster Bay Landings is a private gated neighborhood containing 14 original luxury residential homesites. It is located within the surrounding Oyster Bay Estates area but has its own controlled entrance and neighborhood characteristics.
Do Oyster Bay Landings homes include deeded boat docks?
Oyster Bay Landings is known for deeded boating privileges associated with its waterfront homesites. However, buyers should confirm the specific dock rights, slip dimensions, water depth, permits, and navigational conditions for the property they are considering.
What types of homes are available in Oyster Bay Landings?
Oyster Bay Landings features custom luxury single-family residences with a variety of architectural styles, including coastal, West Indies-inspired, courtyard, and contemporary modern designs. Home sizes, construction dates, and outdoor features vary by property.
Does living in Oyster Bay Landings include The Field Club membership?
No. The Field Club is a separate private waterfront club offering boating, tennis, swimming, dining, and social amenities. Membership is not automatically included with ownership of a home in Oyster Bay Landings.
Interested in Oyster Bay Landings luxury homes for sale? Contact The Wendy Lynn Group at eXp Realty for assistance exploring available waterfront estates, comparing nearby West of the Trail neighborhoods, and understanding dock privileges, HOA regulations, and waterfront ownership considerations. Call 941-421-7375 to begin your Sarasota luxury real estate search.
