Osprey, FL Homes

/99
$629,000

$70K PRICE DROP
- 3 Beds
- 3 Baths
- 2,203 Sq Ft
401 N Point Rd Unit 603, Osprey, FL 34229

Virtually Staged. This incredible offering has everything you need to live a luxury condominium lifestyle in comfort and ease; 3 bedrooms, 3 full baths, a formal dining room and a 2ND FLOOR PRIVATE 2 CAR GARAGE! Add to this, gorgeous views from almost every room, and you have found a well-priced gem in Meridian at The Oaks Preserve to enjoy all the Gulf Coast has to offer. Take the private

Steve Abbe COLDWELL BANKER REALTY

401 N Point Rd Unit 603, Osprey, FL 34229
/2
$689,000

Sold Mar 06, 2026

162 Willow Bend Way, Osprey, FL 34229
- 4 Beds
- 3 Baths
- 2,661 Sq Ft
- Built 2004
Last Sold Summary
- $259/SF
- 4 Days On Market
Current Estimated Value $687,454

Last Listing Agent Kim Azar-Calka MICHAEL SAUNDERS & COMPANY

162 Willow Bend Way, Osprey, FL 34229

Not Listed For Sale

0 N Point Rd Unit A11454780, Osprey, FL 34229
0 N Point Rd Unit A11454780, Osprey, FL 34229

Last Sold Summary
- 218 Days On Market
Last Listing Agent Jennifer Arciniegas Cuadra Group LLC

/45
$474,000

$61K PRICE DROP
- 3 Beds
- 2 Baths
- 1,874 Sq Ft
447 N Shore Dr, Osprey, FL 34229

Classic and cool, this Sorrento Shores beauty blends true Old Florida charm with all the modern updates you actually want, perfectly positioned West of the Trail near the sparkling Intracoastal Waterway. What’s been at the top of your list — move-in ready, a spacious lot, no flood zone, boat/RV parking, optional low HOA, no CDD fees, community marina access, an A+ school district, or quick access

Lauren Sisco COLDWELL BANKER SARASOTA CENT.

447 N Shore Dr, Osprey, FL 34229
/2
$525,000

Sold Dec 04, 2025

1313 Thornapple Dr, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,082 Sq Ft
- Built 2003
Last Sold Summary
- 3% Below List Price
- $252/SF
- 8 Days On Market
Current Estimated Value $530,852

Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

1313 Thornapple Dr, Osprey, FL 34229

/24
Est $281,908

Not Listed For Sale

4224 Expedition Way Unit 105, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,135 Sq Ft
- Built 2016
4224 Expedition Way Unit 105, Osprey, FL 34229

Last Sold Summary
- 0 Days On Market
Last Listing Agent Randal Longo KEYS REALTY REDEFINED LLC

/66
$655,000

Pending
- 3 Beds
- 3 Baths
- 2,251 Sq Ft
816 Shadow Bay Way, Osprey, FL 34229

Set within Rivendell's 400 acres of lakes, preserves, and open spaces, this Osprey pool home checks the boxes buyers rarely find together: a quiet, established neighborhood, a long list of owner-completed upgrades, and no CDD fees. If you're looking for a move-in-ready foundation you can personalize over time, this one deserves a look.Major upgrades include:• NEW ROOF and GARAGE DOOR

Anne Pfitzenreiter COLDWELL BANKER SARASOTA CENT.

816 Shadow Bay Way, Osprey, FL 34229
/2
$765,000

Sold Jan 30, 2026

385 N Point Rd Unit 404, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,778 Sq Ft
- Built 2000
Last Sold Summary
- 17% Below List Price
- $275/SF
- 142 Days On Market
Current Estimated Value $796,090

Last Listing Agent Mark Lyda GENEROUS PROPERTY

385 N Point Rd Unit 404, Osprey, FL 34229

/4
Est $52,681

Not Listed For Sale

570 Blackburn Point Rd Unit 1-SIES, Osprey, FL 34229
- Studio
- 45,244 Sq Ft
570 Blackburn Point Rd Unit 1-SIES, Osprey, FL 34229

Last Sold Summary
- 21 Days On Market
Last Listing Agent Christopher Pelletier CHRISTOPHER PELLETIER BROKER

/11
$575,000
- Land
- 17,424 Sq Ft
- $1,437,500 per Acre
143 Osprey Point Dr, Osprey, FL 34229

One of the last available homesites in The Oaks Bayside. Almost 1/2 acre, at 17,647-square-feet, this exceptional lot presents a rare opportunity to build a custom luxury residence in one of Sarasota's most established and prestigious gated communities.Located behind the 24-hour staffed gates of The Oaks Bayside, this desirable homesite is ready to be transformed into the home you've always

Steve Abbe COLDWELL BANKER REALTY

143 Osprey Point Dr, Osprey, FL 34229
/2
$1,325,000

Sold Jun 16, 2026

140 Sugar Mill Dr, Osprey, FL 34229
- 4 Beds
- 4 Baths
- 3,286 Sq Ft
- Built 1989
Last Sold Summary
- 24% Below List Price
- $403/SF
- 54 Days On Market
Current Estimated Value $1,344,333

Last Listing Agent Monica Verinder COLDWELL BANKER REALTY

140 Sugar Mill Dr, Osprey, FL 34229

/12
Est $23,840

Not Listed For Sale

570 Blackburn Point Rd Unit 9-LIDO, Osprey, FL 34229
- Studio
- 45,244 Sq Ft
570 Blackburn Point Rd Unit 9-LIDO, Osprey, FL 34229

Last Sold Summary
- 69 Days On Market
Last Listing Agent Stephen Mason PREFERRED SHORE LLC

/16
$309,950

$25K PRICE DROP
- 2 Beds
- 2 Baths
- 1,593 Sq Ft
108 Villa Dr Unit 108, Osprey, FL 34229

Come for the investment, stay for the lifestyle! Discover an exceptional waterfront opportunity in Sorrento Shores, a quiet, pet-friendly community of just 28 homes, ideally located minutes from Nokomis Beach, I-75, and the nationally recognized Pine View School.Whether you're looking for a Florida retreat, investment property, or your own year-round coastal home, this spacious, detached

Dr. Richard Gaspar LOKATION

108 Villa Dr Unit 108, Osprey, FL 34229
/2
$175,000

Sold Feb 23, 2026

216 Glenwood Ave, Osprey, FL 34229
- 2 Beds
- 1 Bath
- 732 Sq Ft
- Built 1989
Last Sold Summary
- 30% Below List Price
- $239/SF
- 64 Days On Market
Current Estimated Value $195,060

Last Listing Agent Kristen Wheat COMPASS FLORIDA LLC

216 Glenwood Ave, Osprey, FL 34229

/50
Est $534,924

Not Listed For Sale

2006 Preymore St, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 2,004 Sq Ft
- Built 2023
2006 Preymore St, Osprey, FL 34229

Last Sold Summary
- 10 Days On Market
Last Listing Agent Lee Brewer RE/MAX ALLIANCE GROUP

/2
$699,000
- Land
- 23,958 Sq Ft
- $1,270,909 per Acre
410 Blue Garden Ln, Osprey, FL 34229

Exceptional opportunity to build your dream estate in The Oaks, one of South Sarasota’s most prestigious gated golf and country club communities. Situated on a rare cul-de-sac lot, this generous parcel offers privacy, mature landscaping, and an ideal canvas for a custom residence. Enjoy convenient access to world-class amenities including championship golf, tennis and pickleball facilities, a

Mark Grigoli ELITE PROPERTIES LLC

410 Blue Garden Ln, Osprey, FL 34229
/2
$227,000

Sold Dec 15, 2025

111 Woodland Place, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,316 Sq Ft
- Built 1979
Last Sold Summary
- 7% Below List Price
- $172/SF
- 81 Days On Market
Current Estimated Value $223,774

Last Listing Agent Priscilla Adams COMPASS FLORIDA LLC

111 Woodland Place, Osprey, FL 34229

/2
Est $284,706

Not Listed For Sale

128 Navigation Cir Unit 103, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,244 Sq Ft
- Built 2016
128 Navigation Cir Unit 103, Osprey, FL 34229

Last Sold Summary
- 5 Days On Market
Last Listing Agent Tim Weller EXIT KING REALTY

/70
$1,595,000

$54K PRICE DROP Pre-Foreclosure
- 4 Beds
- 4 Baths
- 4,001 Sq Ft
75 Osprey Point Dr, Osprey, FL 34229

Offered at a price approaching the value of the two buildable lots alone, this architect-designed estate represents one of the most compelling opportunities currently available in The Oaks.Nestled beneath majestic oak trees and surrounded by exceptional privacy, this architecturally significant residence was designed by and as the personal home of renowned architect Bo MacEwen. The

Steve Abbe COLDWELL BANKER REALTY

75 Osprey Point Dr, Osprey, FL 34229
/2
$700,000

Sold May 27, 2026

665 Crane Prairie Way, Osprey, FL 34229
- 4 Beds
- 3 Baths
- 2,306 Sq Ft
- Built 2003
Last Sold Summary
- 3% Below List Price
- $304/SF
- 37 Days On Market
Current Estimated Value $699,944

Last Listing Agent Todd Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

665 Crane Prairie Way, Osprey, FL 34229

/17
Est $290,795

Not Listed For Sale

4247 Expedition Way Unit 103, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,244 Sq Ft
- Built 2016
4247 Expedition Way Unit 103, Osprey, FL 34229

Last Sold Summary
- 89 Days On Market
Last Listing Agent Uli Wills WILLS REAL ESTATE LLC

/45
$249,900

$20K PRICE DROP
- 2 Beds
- 2 Baths
- 1,325 Sq Ft
116 Woodland Place Unit 116, Osprey, FL 34229

Ready to make the move to paradise? Here’s your new home! Adorable two bedroom condo refreshed and ready for a new owner to enjoy convenience living. Crisp and clean with new luxury vinyl in the living room, dining room, hallway and entry, plus just freshly painted! Enjoy a bit of character with the shiplap wood wall in the dining room. Bathrooms have been remodeled with upscale appointments such

Pat Williams PAT WILLIAMS REALTY, LLC

116 Woodland Place Unit 116, Osprey, FL 34229
/2
$137,000

Sold Apr 17, 2026

214 Palm Air Dr, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 959 Sq Ft
- Built 1979
Last Sold Summary
- 2% Below List Price
- $143/SF
- 1 Day On Market
Last Listing Agent Garrett Sedlacek KELLER WILLIAMS ON THE WATER S

214 Palm Air Dr, Osprey, FL 34229

/39
Not Listed For Sale

169 Edgewood Dr, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 1,664 Sq Ft
- Built 2016
169 Edgewood Dr, Osprey, FL 34229

Last Sold Summary
- 372 Days On Market
Last Listing Agent Christy Neff MICHAEL SAUNDERS & COMPANY

/46
$449,000

Under Contract
- 3 Beds
- 1 Bath
- 1,173 Sq Ft
429 Patterson Ave, Osprey, FL 34229

Under contract-accepting backup offers. Incredible opportunity with a $10,000 credit to buyers at closing for costs or a rate buy-down! This low-maintenance gem is fully updated with a NEW AC, brand-new ductwork, stylish new counters/backsplash, new dishwasher, and a beautifully refreshed bathroom. The backyard is a private oasis boasting a brand-new 2025 heated saltwater pool and spa. Location

Brent Martin MARCUS & COMPANY REALTY

429 Patterson Ave, Osprey, FL 34229
/2
$2,300,000

Sold Nov 05, 2025

264 Saratoga Ct, Osprey, FL 34229
- 4 Beds
- 3.5 Baths
- 3,857 Sq Ft
- Built 1992
Last Sold Summary
- $596/SF
- 9 Days On Market
Current Estimated Value $2,247,876

Last Listing Agent Mark Lyda GENEROUS PROPERTY

264 Saratoga Ct, Osprey, FL 34229

/2
Est $894,710

Not Listed For Sale

280 Hidden Bay Dr Unit 502, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 1,937 Sq Ft
- Built 2024
280 Hidden Bay Dr Unit 502, Osprey, FL 34229

Last Sold Summary
- 2 Days On Market
Last Listing Agent Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

/36
$2,850,000
- Land
- 4.18 Acres
- $681,818 per Acre
2301 S Tamiami Trail, Osprey, FL 34229

This listing is for 4.2 +/- acres consisting of two parcels that are rectangular in shape, cleared and level. The parcels have 700 +/- linear feet on US 41 (Tamiami Trail). The daily traffic counts that pass by this property are 41,500 vehicles. The property is currently zoned OPI (Office, Professional and Institutional) and RSF 2 (Residential Single Family 3.5 units / acre). There are two full

Michael Gallatin SARABAY REAL ESTATE INC

2301 S Tamiami Trail, Osprey, FL 34229
/2
$358,000

Sold Nov 13, 2025

115 Green St, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,503 Sq Ft
- Built 1990
Last Sold Summary
- 4% Above List Price
- $238/SF
- 5 Days On Market
Current Estimated Value $359,791

Last Listing Agent Robin Leonardi MICHAEL SAUNDERS & COMPANY

115 Green St, Osprey, FL 34229

/27
Est $333,355

Not Listed For Sale

4260 Expedition Way Unit 4260, Osprey, FL 34229
- 3 Beds
- 2.5 Baths
- 1,581 Sq Ft
- Built 2017
4260 Expedition Way Unit 4260, Osprey, FL 34229

Last Sold Summary
- 94 Days On Market
Last Listing Agent Thomas Cail RE/MAX ALLIANCE GROUP

/62
$615,000

$45K PRICE DROP
- 3 Beds
- 3 Baths
- 2,055 Sq Ft
385 N Point Rd Unit 402, Osprey, FL 34229

**BEAUTIFULLY UPDATED CONDO with MARVELOUS VIEW** features 3-BEDS and 3-FULL BATH, Open Floorplan and is located behind the Secure Gates of the highly sought after Oaks-Preserve, Country Club neighborhood. As you emerge from your private elevator lobby, you will be enthralled by the Impressively Renovated interior which boasts Engineered Hardwood and designer Wood Plank Tile flooring, Plantation

Mark Lyda GENEROUS PROPERTY

385 N Point Rd Unit 402, Osprey, FL 34229
/2
$527,500

Sold Feb 27, 2026

315 Bayshore Dr, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,384 Sq Ft
- Built 1979
Last Sold Summary
- 20% Below List Price
- $221/SF
- 72 Days On Market
Current Estimated Value $558,768

Last Listing Agent Norma Mladineo COLDWELL BANKER REALTY

315 Bayshore Dr, Osprey, FL 34229

/2
Not Listed For Sale

199 Palm Air Dr, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 959 Sq Ft
- Built 1978
199 Palm Air Dr, Osprey, FL 34229

Last Sold Summary
- 87 Days On Market
Last Listing Agent Allison Bollero KELLER WILLIAMS ISLAND LIFE REAL ESTATE

/4
$109,000
570 Blackburn Point Rd Unit 13, Osprey, FL 34229

The slip can hold a boat with the maximum dimensions of 32.5L x 9'W x 9'H. This high-end dry boat storage facility has been hurricane rated. The facility houses 186 boat slips of varying sizes. The marina itself provides a full-service staff to handle all of your boating needs. This includes fuel, bait, ice, deli, drinks, pump out station, work racks supplied with water and electric. There is

David Babel BRIGHT REALTY

570 Blackburn Point Rd Unit 13, Osprey, FL 34229
/2
$520,000

Sold Feb 26, 2026

566 Oak Bay Dr, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 2,559 Sq Ft
- Built 1997
Last Sold Summary
- 2% Below List Price
- $203/SF
- 4 Days On Market
Current Estimated Value $522,572

Last Listing Agent Greg Walters SARABAY REAL ESTATE INC

566 Oak Bay Dr, Osprey, FL 34229

/24
Est $536,859

Not Listed For Sale

2001 Cordes St, Osprey, FL 34229
- 3 Beds
- 2.5 Baths
- 1,975 Sq Ft
- Built 2023
2001 Cordes St, Osprey, FL 34229

Last Sold Summary
- 197 Days On Market
Last Listing Agent Noah Ward EXP REALTY LLC

/44
$875,000

$35K PRICE DROP
- 3 Beds
- 2 Baths
- 2,271 Sq Ft
293 Turquoise Ln, Osprey, FL 34229

**STUNNING, UPDATED, MAINTENANCE-FREE Home is located in EMERALD WOODS, behind the Secure Gates of the Distinguished OAKS PRESERVE Neighborhood. Offering 3-Beds (or 2-Beds plus Den), 2-Baths and 2-Car Garage, Premium finishes abound throughout this home and include a Chef’s Kitchen, Tray Ceilings, Crown Moldings, Beautiful Luxury Vinyl Wood Plank, Plantation Shutters, an Oversized, Owner’s

Mark Lyda GENEROUS PROPERTY

293 Turquoise Ln, Osprey, FL 34229
/2
$540,000

Sold Nov 24, 2025

813 Oak Pond Dr, Osprey, FL 34229
- 4 Beds
- 2 Baths
- 1,981 Sq Ft
- Built 1996
Last Sold Summary
- 4% Below List Price
- $273/SF
- 121 Days On Market
Current Estimated Value $541,032

Last Listing Agent Jeremy Egglefield PREFERRED SHORE LLC

813 Oak Pond Dr, Osprey, FL 34229

/48
Est $348,478

Not Listed For Sale

123 Revolution Way Unit 101, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,574 Sq Ft
- Built 2016
123 Revolution Way Unit 101, Osprey, FL 34229

Last Sold Summary
- 4 Days On Market
Last Listing Agent Tim Weller EXIT KING REALTY

/38
$625,000

$25K PRICE DROP
- 3 Beds
- 2.5 Baths
- 2,045 Sq Ft
12645 Promenade Estates Blvd, Osprey, FL 34238

Welcome to this beautifully cared-for 3-bedroom, 2.5-bath, plus office/den home nestled within the sought-after gated community of Promenade Estates in Palmer Ranch. Thoughtfully designed for both everyday comfort and entertaining, this home offers an open-concept layout with split bedrooms that provide both functionality and privacy. The spacious main living areas create a bright and inviting

Julie Franklin FINE PROPERTIES

12645 Promenade Estates Blvd, Osprey, FL 34238

Showing Results 121 - 160, Page 4 of 18

Florida Sarasota County

How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Osprey, FL Homes

Real Estate & Homes