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You are here: Home / Bayside Homes for Sale | Osprey Florida

Bayside Homes for Sale | Osprey Florida

Bayside in Osprey is an intimate waterfront community overlooking Little Sarasota Bay and located just minutes from Casey Key. This private neighborhood offers a limited collection of luxury single-family homes in one of the most desirable coastal settings in Sarasota County. Buyers looking for newer construction near the water are often drawn to Bayside for its combination of elegant architecture, natural surroundings, and convenient location.

Positioned just north of Blackburn Point Road, Bayside provides a quiet residential atmosphere while still offering easy access to nearby shopping, dining, and Gulf Coast recreation. The community blends upscale living with scenic preserve and bay views, making it an appealing option for buyers seeking a refined coastal lifestyle in Osprey.

Explore more Osprey homes for sale to compare nearby waterfront and luxury communities located between Sarasota and Venice.

Homes in Bayside

Bayside features thoughtfully designed single-family homes with spacious floor plans, open living areas, and architectural styling inspired by coastal Mediterranean influences. Many homes include gourmet kitchens, expansive primary suites, large windows, and covered lanais designed to take advantage of the surrounding preserve and bay views.

With a limited number of homesites, the neighborhood maintains a peaceful and private setting. Many residences are positioned to capture views of Little Sarasota Bay or protected natural areas, creating a distinctive residential environment that balances luxury and nature.

Community Amenities

  • Waterfront community overlooking Little Sarasota Bay
  • Limited collection of luxury homes
  • Nature preserves and green space
  • Walking trails
  • Kayak launch access
  • Community boardwalk
  • Dock access opportunities
  • Fire pit gathering area
  • Scenic bay and preserve views
  • Convenient access to Blackburn Point Road

Location

Bayside is located in Osprey just north of Blackburn Point Road, offering convenient access to the Tamiami Trail corridor and nearby Gulf Coast destinations. Residents enjoy a central location between Sarasota and Venice, along with easy access to shopping, dining, and outdoor recreation.

The neighborhood’s coastal position allows homeowners to enjoy both privacy and proximity to beaches, marinas, and nature preserves throughout Sarasota County.

Nearby Beaches and Attractions

Bayside is located just minutes from the beaches of Casey Key and nearby waterfront destinations in Nokomis and Osprey. Outdoor enthusiasts also appreciate the convenient access to local parks, boating opportunities, and scenic coastal landscapes that define this part of Southwest Florida.

Similar Communities

  • Sorrento Shores – Waterfront neighborhood located near Blackburn Point and Casey Key.
  • Bay Oaks – Established community featuring larger homesites and mature landscaping.
  • Oaks Bayside – Luxury homes located within The Oaks Club near Little Sarasota Bay.
  • Southbay Yacht & RC – Marina community offering boating access and clubhouse amenities.
  • Blackburn Harbor – Waterfront residences with Intracoastal access.

Bayside Homes for Sale | Osprey Florida

97 SUGAR MILL DRIVE OSPREY FL 34229
Open House Sun, May 17, 1 PM
1 / 61
$1,950,000
Single Family Residence For Sale
Active
5
BEDS
6
TOTAL BATHS
4,885
SQFT
97 SUGAR MILL DRIVE
OSPREY, FL 34229
OAKS Subdivision
449 WEBBS COVE OSPREY FL 34229
New Listing - 2 weeks on site
1 / 97
$2,650,000
Single Family Residence For Sale
Active
4
BEDS
4
TOTAL BATHS
5,287
SQFT
449 WEBBS COVE
OSPREY, FL 34229
OAKS Subdivision
662 FERNWALK LANE OSPREY FL 34229
1 / 73
$2,850,000
Single Family Residence For Sale
Active
4
BEDS
4
TOTAL BATHS
4,359
SQFT
662 FERNWALK LANE
OSPREY, FL 34229
OAKS Subdivision
25 SUGAR MILL DRIVE OSPREY FL 34229
Price Change - 2 weeks ago
1 / 74
$1,550,000
Single Family Residence For Sale
Active
3
BEDS
4
TOTAL BATHS
3,066
SQFT
25 SUGAR MILL DRIVE
OSPREY, FL 34229
OAKS Subdivision
75 OSPREY POINT DRIVE OSPREY FL 34229
Open House Sun, May 17, 12 PM
1 / 92
$1,695,000
Single Family Residence For Sale
Active
4
BEDS
4
TOTAL BATHS
4,001
SQFT
75 OSPREY POINT DRIVE
OSPREY, FL 34229
OAKS Subdivision
49 OSPREY POINT DRIVE OSPREY FL 34229
Price Change - 2 weeks ago
1 / 96
$2,399,000
Single Family Residence For Sale
Active
4
BEDS
4
TOTAL BATHS
3,953
SQFT
49 OSPREY POINT DRIVE
OSPREY, FL 34229
OAKS Subdivision
422 BLUE GARDEN LANE OSPREY FL 34229
Price Change - 2 weeks ago
1 / 100
$1,550,000
Single Family Residence For Sale
Active
3
BEDS
4
TOTAL BATHS
3,872
SQFT
422 BLUE GARDEN LANE
OSPREY, FL 34229
OAKS Subdivision

Frequently Asked Questions

Where is Bayside located?

Bayside is located in Osprey, Florida just north of Blackburn Point Road overlooking Little Sarasota Bay.

What type of homes are available in Bayside?

Bayside features luxury single-family homes with spacious floor plans and coastal architectural styling.

Is Bayside a waterfront community?

Yes, Bayside is a waterfront neighborhood with many homes enjoying views of Little Sarasota Bay and nearby preserves.

How close is Bayside to the beach?

Bayside is located a short drive from Casey Key and nearby Gulf Coast beaches.

What makes Bayside unique?

Bayside offers a limited number of luxury homes in a private waterfront setting near some of the most desirable coastal destinations in Sarasota County.

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The Wendy Lynn Group Sarasota exp Realty



  • 1300 Main Street, Sarasota, FL 34236

  • 941-421-7375

  • info@sunnysarasotahomes.com

Osprey Neighborhoods

  • Bay Oaks
  • Bay Street
  • Bayside
  • Bellagio Harbor
  • Blackburn Harbor
  • Cordes Cove
  • Heron Bay Club
  • Hidden Bay
  • Oaks Bayside
  • Oaks Clubside
  • Oaks Preserve
  • Osprey Harbor Village
  • Palms at Casey Key
  • Park Trace Estates
  • Pine Run
  • Rivendell
  • Sorrento Shores
  • South Creek
  • Southbay Yacht & RC
  • Willowbend

Areas We Serve

  • Anna Maria
  • Bird Key
  • Bradenton
  • Bradenton Beach
  • Casey Key
  • Cortez
  • Downtown Sarasota
  • Ellenton
  • Englewood
  • Golden Gate
  • Holmes Beach
  • Lakewood Ranch
  • Lido Key
  • Longboat Key
  • Myakka City
  • Nokomis
  • North Port
  • Osprey
  • Palmer Ranch
  • Palmetto
  • Parrish
  • Sarasota
  • Siesta Key
  • South Hillsborough
  • Terra Ceia
  • University Park
  • Venice
  • West of the Trail

Things to do in Osprey Florida

https://www.youtube.com/watch?v=JJT1XzDeJLU

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The Wendy Lynn Group Sarasota exp Realty

  • 1300 Main Street, Sarasota, FL 34236
  • 941-421-7375
  • info@sunnysarasotahomes.com

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Wendy_Realtor avatar Wendy Lynn @Wendy_Realtor ·
42m 2055260683525132314

Ellenton continues expanding with both affordability and accessibility advantages.,#EllentonFlorida,

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Explore Ellenton homes for sale, neighborhoods, and real estate options in this growing Manatee County community near Bradenton and the Manatee River.

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Wendy_Realtor avatar Wendy Lynn @Wendy_Realtor ·
14 May 2054898333865378296

Waterfront demand in Sarasota County remains steady across multiple price points.,#WaterfrontHomes,

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Waterfront Homes for Sale in Manatee and Sarasota County

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www.sunnysarasotahomes.com

Wendy_Realtor avatar Wendy Lynn @Wendy_Realtor ·
13 May 2054535904849453500

Every market cycle presents opportunity for those paying attention.,#MarketUpdate,https://www.wendylynngroup.com/market-report.php

Wendy_Realtor avatar Wendy Lynn @Wendy_Realtor ·
12 May 2054245559041683870

🛌 2 🛀 3 🚘 1
📍 2 bed | 3 bath | 1 car

It was our pleasure to help get this one sold!
Need to Sell Yours? Just Say "WEN" 941-421-7375

https://rma.reviews/miaw5pd5sccc

...
#sold #wendylynngroup #realtor #sarasota #bradenton #srq #lwr #realestate #lakewoodranch...

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Wendy_Realtor avatar Wendy Lynn @Wendy_Realtor ·
12 May 2054173520729399306

Bradenton Beach offers waterfront living with a laid-back coastal atmosphere.,#BradentonBeach,

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Bradenton Beach Florida Homes for Sale and Condos

Bradenton Beach homes for sale including island homes, waterfront properties, and beach condos on Anna Maria Island.

www.sunnysarasotahomes.com

Wendy_Realtor avatar Wendy Lynn @Wendy_Realtor ·
11 May 2053811133580980389

Testing the market rarely produces the strongest result. Positioning does.,#HomeSelling,https://www.wendylynngroup.com/seller/valuation/

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