• Skip to primary navigation
  • Skip to main content
  • Skip to primary sidebar
  • Skip to footer

The Wendy Lynn Group: Sarasota Homes and Condos

The Wendy Lynn Group - www.SarasotaHomesandCondos.com

  • Advanced Home Search
  • Areas
  • Featured Listings
    • Sold Listings
  • Selling
    • Market Report
  • Blog
  • About
    • Wendy Lynn
    • Josh Lynn
    • Testimonials
  • Contact
  • Email
  • Facebook
  • Instagram
  • LinkedIn
  • Phone
  • Pinterest
  • Twitter
  • YouTube
You are here: Home / Oaks Clubside Homes for Sale | Osprey Florida

Oaks Clubside Homes for Sale | Osprey Florida

Oaks Clubside is an elegant luxury home community located within The Oaks Club in Osprey. Known for its championship golf course views, mature landscaping, and spacious homesites, Oaks Clubside offers an upscale residential setting in one of Sarasota County’s most respected private country club communities. Buyers searching for luxury real estate in West of the Trail often consider Oaks Clubside for its privacy, natural beauty, and convenient location between Sarasota and Venice.

The Oaks Club features two championship golf courses and a well-established reputation for refined living. Homes in Oaks Clubside are positioned around the golf course and scenic preserves, creating a peaceful atmosphere with beautiful year-round views.

Explore more Osprey homes for sale to compare similar golf and luxury communities located near Casey Key and the Intracoastal Waterway.

Homes in Oaks Clubside

Homes in Oaks Clubside are custom-built luxury residences offering spacious floor plans, high ceilings, and well-designed indoor and outdoor living spaces. Many properties feature private swimming pools, expansive lanais, gourmet kitchens, and architectural details inspired by Mediterranean and contemporary Florida design.

The neighborhood is known for its large homesites, tree-lined streets, and golf course views. Buyers appreciate the established character of the community along with the prestige associated with living within The Oaks Club.

Community Amenities

  • Located within The Oaks Club
  • Private golf and country club community
  • Championship golf courses
  • Clubhouse dining
  • Tennis courts
  • Fitness center
  • Gated entry
  • Mature landscaping
  • Golf course views
  • West of the Trail location

Location

Oaks Clubside is located in Osprey, just west of US-41 and conveniently positioned between Sarasota and Venice. The community offers easy access to shopping, dining, and outdoor recreation throughout the Gulf Coast region.

The location allows residents to enjoy a quiet residential setting while still being close to many of the cultural and lifestyle amenities Sarasota County provides.

Nearby Beaches and Attractions

Oaks Clubside is located a short drive from Casey Key, where residents can enjoy Gulf beaches, boating, and waterfront dining. The nearby Intracoastal Waterway offers additional opportunities for boating and water activities.

Shopping, dining, and cultural attractions can be found in nearby Sarasota and Venice.

Similar Communities

  • Oaks Bayside – Luxury homes located within The Oaks Club near the Intracoastal Waterway.
  • Oaks Preserve – Maintenance-free luxury homes within The Oaks Club.
  • Sorrento Shores – West of the Trail neighborhood offering waterfront homes.
  • Bayside – Private waterfront community overlooking Little Sarasota Bay.
  • Southbay Yacht & RC – Marina community featuring boating amenities.

Oaks Clubside Homes for Sale | Osprey Florida

299 TURQUOISE LANE OSPREY FL 34229
New Listing - 3 weeks on site
1 / 79
$739,000
Single Family Residence For Sale
Active
3
BEDS
2
TOTAL BATHS
2,328
SQFT
299 TURQUOISE LANE
OSPREY, FL 34229
EMERALD WOODS AT OAKS 03 PH 02 Subdivision
916 MACEWEN DRIVE OSPREY FL 34229
New Listing - 4 weeks on site
1 / 97
$1,900,000
Single Family Residence For Sale
Active
5
BEDS
8
TOTAL BATHS
5,986
SQFT
916 MACEWEN DRIVE
OSPREY, FL 34229
OAKS 2 PH 2 Subdivision
401 N POINT ROAD 504 OSPREY FL 34229
Price Change - a week ago
1 / 54
$795,000
Condominium For Sale
Active
3
BEDS
3
TOTAL BATHS
2,778
SQFT
401 N POINT ROAD 504
OSPREY, FL 34229
MERIDIAN AT THE OAKS PRESERVE Subdivision
143 OSPREY POINT DRIVE OSPREY FL 34229
1 / 11
$575,000
Land For Sale
Active
0.4
ACRES
SARASOTA
COUNTY
143 OSPREY POINT DRIVE
OSPREY, FL 34229
 
75 OSPREY POINT DRIVE OSPREY FL 34229
Price Change - 6 days ago
1 / 70
$1,595,000
Single Family Residence For Sale
Active
4
BEDS
4
TOTAL BATHS
4,001
SQFT
75 OSPREY POINT DRIVE
OSPREY, FL 34229
OAKS Subdivision
360 N POINT ROAD OSPREY FL 34229
1 / 49
$1,495,000
Single Family Residence For Sale
Active
3
BEDS
4
TOTAL BATHS
2,913
SQFT
360 N POINT ROAD
OSPREY, FL 34229
OAKS Subdivision
216 OSPREY POINT DRIVE OSPREY FL 34229
1 / 31
$695,000
Land For Sale
Active
0.59
ACRES
SARASOTA
COUNTY
216 OSPREY POINT DRIVE
OSPREY, FL 34229
OAKS Subdivision
101 OSPREY POINT DRIVE OSPREY FL 34229
1 / 65
$4,790,000
Single Family Residence For Sale
Active
4
BEDS
6
TOTAL BATHS
5,087
SQFT
101 OSPREY POINT DRIVE
OSPREY, FL 34229
OAKS Subdivision
103 BISHOPS COURT ROAD OSPREY FL 34229
1 / 55
$749,000
Single Family Residence For Sale
Active
3
BEDS
2
TOTAL BATHS
2,034
SQFT
103 BISHOPS COURT ROAD
OSPREY, FL 34229
OAKS Subdivision
619 OAK RIVER COURT OSPREY FL 34229
1 / 42
$609,900
Single Family Residence For Sale
Active Under Contract
3
BEDS
2
TOTAL BATHS
2,047
SQFT
619 OAK RIVER COURT
OSPREY, FL 34229
BAY OAKS ESTATES Subdivision
156 BISHOPS COURT ROAD OSPREY FL 34229
Open House Sun, Aug 30, 1 PM
1 / 84
$1,289,000
Single Family Residence For Sale
Active
3
BEDS
4
TOTAL BATHS
3,112
SQFT
156 BISHOPS COURT ROAD
OSPREY, FL 34229
OAKS Subdivision
51 MACEWEN DRIVE 12 OSPREY FL 34229
1 / 71
$275,000
Condominium For Sale
Active
1
BED
1
TOTAL BATH
623
SQFT
51 MACEWEN DRIVE 12
OSPREY, FL 34229
OAKS Subdivision
97 SUGAR MILL DRIVE OSPREY FL 34229
Open House Sat, Aug 22, 12 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
409 NORTH POINT ROAD 401 OSPREY FL 34229
1 / 90
$560,000
Condominium For Sale
Active
3
BEDS
3
TOTAL BATHS
2,594
SQFT
409 NORTH POINT ROAD 401
OSPREY, FL 34229
MERIDIAN AT THE OAKS PRESERVE Subdivision
51 MAC EWEN DRIVE 14 OSPREY FL 34229
1 / 19
$285,000
Condominium For Sale
Active
1
BED
1
TOTAL BATH
595
SQFT
51 MAC EWEN DRIVE 14
OSPREY, FL 34229
OAKS Subdivision
51 MACEWEN DRIVE 5 OSPREY FL 34229
1 / 44
$235,000
Condominium For Sale
Active
1
BED
1
TOTAL BATH
595
SQFT
51 MACEWEN DRIVE 5
OSPREY, FL 34229
WINDSOR LODGE AT THE OAKS Subdivision
448 E MACEWEN DRIVE OSPREY FL 34229
1 / 52
$2,100,000
Single Family Residence For Sale
Active Under Contract
4
BEDS
4
TOTAL BATHS
3,768
SQFT
448 E MACEWEN DRIVE
OSPREY, FL 34229
OAKS Subdivision
3621 N POINT ROAD 301 OSPREY FL 34229
Price Change - a week ago
1 / 95
$525,000
Condominium For Sale
Active
3
BEDS
3
TOTAL BATHS
2,680
SQFT
3621 N POINT ROAD 301
OSPREY, FL 34229
MERIDIAN AT THE OAKS PRESERVE Subdivision
409 N POINT ROAD 601 OSPREY FL 34229
1 / 63
$1,250,000
Condominium For Sale
Active
3
BEDS
3
TOTAL BATHS
2,594
SQFT
409 N POINT ROAD 601
OSPREY, FL 34229
MERIDIAN AT THE OAKS PRESERVE Subdivision
401 N POINT ROAD 1001 OSPREY FL 34229
1 / 60
$1,995,000
Condominium For Sale
Active
3
BEDS
3
TOTAL BATHS
3,029
SQFT
401 N POINT ROAD 1001
OSPREY, FL 34229
MERIDIAN AT THE OAKS PRESERVE Subdivision

Frequently Asked Questions

Where is Oaks Clubside located?

Oaks Clubside is located in Osprey, Florida within The Oaks Club golf and country club community.

What type of homes are available in Oaks Clubside?

Oaks Clubside features luxury custom single-family homes with golf course and preserve views.

Is Oaks Clubside located West of the Trail?

Yes, Oaks Clubside is located in the desirable West of the Trail area near the Intracoastal Waterway.

Does Oaks Clubside offer golf access?

The community is located within The Oaks Club, offering championship golf courses and country club amenities.

How close is Oaks Clubside to the beach?

Oaks Clubside is located a short drive from Casey Key and other Gulf Coast beaches.

Primary Sidebar

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

Footer

The Wendy Lynn Group Sarasota exp Realty

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

Connect with Us!

  • Email
  • Facebook
  • Instagram
  • LinkedIn
  • Phone
  • Pinterest
  • Twitter
  • YouTube

Wendy Lynn on X

Wendy_Realtor avatar

Wendy Lynn

@Wendy_Realtor ·
12h 2090049916240306459

Balanced markets reward decisiveness. Hesitation can be expensive.,#MarketStrategy,https://www.wendylynngroup.com/market-report.php

Wendy_Realtor avatar

Wendy Lynn

@Wendy_Realtor ·
18 Aug 2089687535572164661

Architectural character often commands stronger buyer attachment than square footage.,#ArchitecturalHomes,

Image for twitter card

Manatee & Sarasota County Homes for Sale by Architectural Style

Homes of Manatee & Sarasota County by Architectural Style. Search Contemporary, Mediterranean, Ranch, Historic, Key West and many others.

www.sunnysarasotahomes.com

Wendy_Realtor avatar

Wendy Lynn

@Wendy_Realtor ·
17 Aug 2089325159886790899

"If your home hasn�t attracted qualified showings, the strategy needs adjustment.",#HomeSelling,https://www.wendylynngroup.com/seller/valuation/

Wendy_Realtor avatar

Wendy Lynn

@Wendy_Realtor ·
14 Aug 2088238004405956892

"Sarasota�s diversity � urban, suburban, and coastal � creates layered market behavior.",#Sarasota,

Image for twitter card

Sarasota Florida Homes for Sale | Neighborhoods & Condos

Explore Sarasota FL homes for sale including waterfront properties, golf communities, downtown condos & popular neighbor...

www.sunnysarasotahomes.com

Wendy_Realtor avatar

Wendy Lynn

@Wendy_Realtor ·
13 Aug 2087875595069788341

Luxury buyers are rarely rate-driven; they are lifestyle-driven.,#LuxuryRealEstate,

Image for twitter card

Luxury Homes & Condos in Manatee & Sarasota County

Luxury Homes for Sale & Condos in Manatee & Sarasota County

www.sunnysarasotahomes.com

Wendy_Realtor avatar

Wendy Lynn

@Wendy_Realtor ·
12 Aug 2087513202116448642

Inventory growth does not eliminate demand � it refines it.,#MarketInsight,https://www.wendylynngroup.com/market-report.php

Search Our Site

  • © 2010–2026
  • SARASOTA HOMES & CONDOS SITEMAP
  • HOME PAGE