Skip to main content
  • Featured Listings
    • Property Types
    • Golf Course Homes
    • Tennis Communities
    • Waterfront
    • Pickleball Communities
    • Mid-Century Homes
    • Modern Homes
    • Airbnb Properties
    • Sarasota School of Architecture
    • Condominiums
    • Townhouses
    • Villas
    • Green Homes
    • New Construction
    • Commercial Property
    • Communities
    • Shop by Sarasota County School District
    • Downtown Sarasota
    • Longboat Key
    • Lakewood Ranch
    • West of Trail
    • Lido Shores
    • Arlington Park & South Gate
    • Lido Key
    • The Landings
    • Siesta Key
    • 34231 Zip Code
    • Casey Key
    • Palmer Ranch
    • Osprey
    • Central Sarasota
    • Southbay
    • Pinecraft | Alta Vista
    • Nokomis
    • The Meadows
    • Venice
    • East of 75
    • About us
    • Contact
    • Featured Listings
  • Join AW&Co
    • My Dashboard
    • My Homes
    • Favorites
    • Saved Searches
    • Messages
    • Preferences
    • Sign Out
  • Sign In
941.350.1220
Sidebar Open Sidebar Close Explore

Communities

  • 34231 Homes
  • 34236 Homes
  • 34237 Homes
  • 34239 Homes
  • Alta Vista, Paver Park, and Ringling Park
  • Arielle
  • Arlington and Southgate
  • Avondale
  • Bayou Oaks
  • Bayview
  • Bee Ridge
  • Bellevue Terrace
  • Bird Key
  • Casey Key
  • Cherokee Park
  • Downtown Sarasota
  • East of 75
  • Granada
  • Gulf Gate Estates
  • Harbor Acres
  • Heritage Oaks
  • Hudson Bayou
  • Kensington Park
  • Lake Sarasota
  • Lakewood Ranch
  • The Landings
  • Laurel Oak
  • Laurel Park
  • Along The Legacy Trail
  • Lido Key
  • Lido Shores
  • Longboat Key
  • McClellan Park
  • The Meadows
  • Nokomis
  • North Downtown Sarasota
  • The Oaks
  • Osprey
  • Palmer Ranch
  • Pinecraft
  • Ridge Wood Heights
  • San Remo
  • Sarasota Heights
  • Sarasota Springs
  • Serenoa
  • Siesta Key
  • South Gate Ridge
  • South Poinsettia
  • South Sarasota
  • Southbay Yacht and Racquet Community
  • St. Armands
  • Stoneybrook
  • TPC Prestancia
  • Tuttle Ave Area of North Sarasota
  • University Park
  • Venetian Golf and River Club
  • Venice, Venice Island, and South Venice
  • West of 75
  • West of the Trail
Home
Communities
Osprey

Homes for Sale in Osprey, Fl

Sort by:
329 Bay Vista Avenue, OSPREY

$399,000

↓ $20,000

329 Bay Vista Avenue, OSPREY

2 Beds 2 Baths 1,346 SqFt Residential MLS® # A4699464
1819 Highland Road, OSPREY

$319,000

1819 Highland Road, OSPREY

2 Beds 3 Baths 1,240 SqFt Residential MLS® # A4703963
4304 Expedition Way Way 105, OSPREY

$318,000

↓ $10,000

4304 Expedition Way Way 105, OSPREY

3 Beds 2 Baths 1,528 SqFt Residential MLS® # N6143250
4213 Expedition Way 107, OSPREY

$317,000

↓ $3,000

4213 Expedition Way 107, OSPREY

3 Beds 2 Baths 1,430 SqFt Residential MLS® # A4698337
4296 Expedition Way 104, OSPREY

$299,990

4296 Expedition Way 104, OSPREY

2 Beds 2 Baths 1,135 SqFt Residential MLS® # A4694926
4226 Frontier Lane 103, OSPREY

$299,000

↓ $20,000

4226 Frontier Lane 103, OSPREY

2 Beds 2 Baths 1,135 SqFt Residential MLS® # A4687965
1801 Highland Road, OSPREY

$289,900

↓ $10,000

1801 Highland Road, OSPREY

2 Beds 2 Baths 1,165 SqFt Residential MLS® # N6140508
108 Woodland Place 108, OSPREY

$285,000

↑ $100,000

108 Woodland Place 108, OSPREY

2 Beds 2 Baths 1,316 SqFt Residential MLS® # A4699279
51 Mac Ewen Drive 14, OSPREY

$285,000

51 Mac Ewen Drive 14, OSPREY

1 Bed 1 Bath 595 SqFt Residential MLS® # A4690371
51 Macewen Drive 12, OSPREY

$275,000

51 Macewen Drive 12, OSPREY

1 Bed 1 Bath 623 SqFt Residential MLS® # A4690540
New
109 Woodland Place, OSPREY

$255,000

109 Woodland Place, OSPREY

2 Beds 2 Baths 1,223 SqFt Residential MLS® # A4705745
Open House
116 Woodland Place 116, OSPREY

$249,900

↓ $5,000

116 Woodland Place 116, OSPREY

2 Beds 2 Baths 1,325 SqFt Residential
Sat, Sep 26th, 2026 @ 1pm - 3pm
MLS® # A4696616
Arrow Left Prev
1 3 4 5 6 7
Next Arrow right
Albert Wooster & Co Logo

Featured Communities

  • New Construction
  • Golf Course Homes
  • West of Trail Homes
  • East Of Trail Homes
  • 34231 Homes
  • Sarasota School of Architecture Homes

Buyers & Sellers

  • Search Listings
  • Mortgage Calculator
  • Request Valuation
  • Seller's Guide
  • Buyer's Guide

Information

  • About Us
  • Search Listings
  • Sarasota Activities Directory
  • Contact Us

Albert Wooster & Co.

Boutique Concierge Realtors

Phone: 941.350.1220
Office Address: 2912 Bee Ridge Rd.
Sarasota, FL 34239

Email: WoosterFLA@gmail.com
Brokerage ID: BK3139453

Twitter Facebook LinkedIn Youtube

© 2026 Real Estate Webmasters All Rights Reserved.
SitemapPrivacy Policy
Real Estate Webmasters will open a new window

All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified.

Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.

Listing data comes from My Florida Regional MLS DBA Stellar MLS.

Listing information last updated on September 22nd, 2026 at 2:37am CDT.