Osprey, FL Homes

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$42,500
570 Blackburn Point Rd Unit CASEY 11, Osprey, FL 34229

Dry boat slip for sale at Osprey Harbor Village, hurricane-protected dry storage with top-tier amenities! Keep your boat safe from Floridas unpredictable weather while enjoying all the benefits of a full-service marina. Located just before the swing bridge to Casey Key at ICW Marker 33 (north of the Blackburn Point Bridge), this slip fits boats up to 33L x 9.5W x 6.5H. With valet boat service,

Daniel Treiman MICHAEL SAUNDERS & COMPANY

570 Blackburn Point Rd Unit CASEY 11, Osprey, FL 34229
/2
$550,000 Sold Feb 19, 2026

494 Meadow Sweet Cir, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 1,791 Sq Ft
- Built 1997
Last Sold Summary
- 8% Below List Price
- $307/SF
- 7 Days On Market
Current Estimated Value $565,251

Last Listing Agent Carlos Saramago EXIT KING REALTY

494 Meadow Sweet Cir, Osprey, FL 34229

/42
Est $590,748 Not Listed For Sale

564 Crane Prairie Way, Osprey, FL 34229
- 4 Beds
- 3 Baths
- 2,079 Sq Ft
- Built 2005
564 Crane Prairie Way, Osprey, FL 34229

Last Sold Summary
- $284/SF
- 69 Days On Market
Last Sold Price $590,000

Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

/76
$950,000 Pending
- 4 Beds
- 3 Baths
- 2,921 Sq Ft
1016 Scherer Way, Osprey, FL 34229

Under contract-accepting backup offers. BEAUTIFUL INSIDE and exceptionally well maintained, this Rivendell home offers the kind of upgrades, efficiency, and outdoor living that are becoming increasingly hard to find. This Luxurious home is situated on a large beautifully landscaped, lake front lot with a Southeast Exposure overlooking Oscar Scherer State park! The interior layout is spacious and

Rachel Tritschler RE/MAX ALLIANCE GROUP

1016 Scherer Way, Osprey, FL 34229
/2
$520,000 Sold Dec 30, 2025

447 Oak Point Rd, Osprey, FL 34229
- 4 Beds
- 3 Baths
- 2,688 Sq Ft
- Built 1994
Last Sold Summary
- 5% Below List Price
- $193/SF
- 49 Days On Market
Current Estimated Value $521,855

Last Listing Agent Priscilla Adams COMPASS FLORIDA LLC

447 Oak Point Rd, Osprey, FL 34229

/3
Est $649,039 Not Listed For Sale

6100 Jessie Harbor Dr Unit 403, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,630 Sq Ft
- Built 2005
6100 Jessie Harbor Dr Unit 403, Osprey, FL 34229

Last Sold Summary
- 10% Below List Price
- $276/SF
- 108 Days On Market
Last Sold Price $725,000

Last Listing Agent Mark Quire KELLER WILLIAMS ON THE WATER S

/58
$3,750,000
- 4 Beds
- 4.5 Baths
- 4,781 Sq Ft
1042 N Casey Key Rd, Osprey, FL 34229

One or more photo(s) has been virtually staged. Exceptional Waterfront Estate on North Casey Key. Set along the coveted shores of North Casey Key, this exceptional waterfront residence presents a rare opportunity to experience the very best of coastal Florida living. Nestled within the sought-after Palmer neighborhood and lovingly maintained by the same discerning owners since 1999, the home

Brandy Sheldon COLDWELL BANKER REALTY

1042 N Casey Key Rd, Osprey, FL 34229
/2
$318,000 Sold Apr 30, 2025

115 Villa Dr Unit 115, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,411 Sq Ft
- Built 1972
Last Sold Summary
- 16% Below List Price
- $225/SF
- 125 Days On Market
Current Estimated Value $303,383

Last Listing Agent EJ Stukenborg KELLER WILLIAMS ON THE WATER S

115 Villa Dr Unit 115, Osprey, FL 34229

/85
Est $985,810 Not Listed For Sale

184 Park Trace Blvd, Osprey, FL 34229
- 5 Beds
- 4.5 Baths
- 3,420 Sq Ft
- Built 2003
184 Park Trace Blvd, Osprey, FL 34229

Last Sold Summary
- 1% Above List Price
- $287/SF
- 52 Days On Market
Last Sold Price $980,000

Last Listing Agent Mark Klecka COLDWELL BANKER REALTY

/62
$349,000
- 2 Beds
- 2 Baths
- 1,400 Sq Ft
2251 Jessie Harbor Dr, Osprey, FL 34229

**1ST FLOOR END UNIT CONDO with WATER VIEW and PRIVATE 1-CAR GARAGE, WEST OF TRAIL! BRING YOUR BOAT & KAYAK for DIRECT ACCESS TO INTRACOASTAL WATERWAY and GULF OF MEXICO (No Bridges)** Featuring 2 BEDS and 2 FULL BATHS, this LIGHT AND BRIGHT, 1ST FLOOR END UNIT dwelling features an Impressive Kitchen with Granite counters, Stainless Steel appliances and solid wood cabinets while the Spacious

Mark Lyda GENEROUS PROPERTY

2251 Jessie Harbor Dr, Osprey, FL 34229
/2
$155,000 Sold Feb 24, 2026

300 Tropic Dr, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,031 Sq Ft
- Built 1986
Last Sold Summary
- 3% Below List Price
- $150/SF
- 54 Days On Market
Last Listing Agent Heidi Lionetti WHITE SANDS REALTY GROUP FL

300 Tropic Dr, Osprey, FL 34229

/2
Est $1,594,856 Not Listed For Sale

738 N MacEwen Dr, Osprey, FL 34229
- 5 Beds
- 5.5 Baths
- 4,614 Sq Ft
- Built 2003
738 N MacEwen Dr, Osprey, FL 34229

Last Sold Summary
- 10% Above List Price
- $314/SF
- 193 Days On Market
Last Sold Price $1,450,000

Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

/34
$630,000
- 3 Beds
- 3 Baths
- 1,840 Sq Ft
408 Park Trace Blvd, Osprey, FL 34229

Welcome to your own private oasis in Park Trace Estates, a stunning 3-bedroom, 3-bath single-family home overlooking water with unobstructed views of the Legacy Trail and Oscar Scherer State Park. Located in a desirable community minutes from Pine View School, healthcare, and beaches, this residence is perfectly designed for indoor-outdoor living. The heart of the home is a beautiful central

Jennie Lascelle PREFERRED SHORE LLC

408 Park Trace Blvd, Osprey, FL 34229
/2
$1,150,000 Sold May 28, 2025

327 Sea Anchor Dr, Osprey, FL 34229
- 2 Beds
- 3 Baths
- 2,521 Sq Ft
- Built 1981
Last Sold Summary
- 7% Below List Price
- $456/SF
- 20 Days On Market
Current Estimated Value $1,144,626

Last Listing Agent Lisa Napolitano DOUGLAS ELLIMAN

327 Sea Anchor Dr, Osprey, FL 34229

/2
Est $1,202,223 Not Listed For Sale

110 N Creek Ln, Osprey, FL 34229
- 3 Beds
- 3.5 Baths
- 4,071 Sq Ft
- Built 2002
110 N Creek Ln, Osprey, FL 34229

Last Sold Summary
- $295/SF
- 8 Days On Market
Last Sold Price $1,200,000

Last Listing Agent Tina Timmons ROSEBAY INTERNATIONAL REALTY, INC

/46
$515,000
- 3 Beds
- 2 Baths
- 1,293 Sq Ft
742 Harms Dr, Osprey, FL 34229

Beautifully renovated and now offered at a newly reduced price, this turnkey property is a fantastic opportunity with motivated sellers. Set on just over half an acre along a private, tree-lined street the home is surrounded by lush tropical landscaping that creates a peaceful and secluded feel. Inside you’ll find a spacious layout with modern finishes and seamless indoor-outdoor living with a

Tiffany Stonis EXP REALTY LLC

742 Harms Dr, Osprey, FL 34229
/2
$640,000 Sold Jun 20, 2025

455 Park Trace Blvd, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,590 Sq Ft
- Built 1999
Last Sold Summary
- 15% Below List Price
- $247/SF
- 119 Days On Market
Current Estimated Value $661,601

Last Listing Agent Kim Azar-Calka MICHAEL SAUNDERS & COMPANY

455 Park Trace Blvd, Osprey, FL 34229

/2
Est $993,523 Not Listed For Sale

146 Yacht Harbor Dr, Osprey, FL 34229
- 3 Beds
- 2.5 Baths
- 2,627 Sq Ft
- Built 1986
146 Yacht Harbor Dr, Osprey, FL 34229

Last Sold Summary
- 1% Below List Price
- $380/SF
Last Sold Price $999,500

Last Listing Agent Susanne Losso COLDWELL BANKER REALTY

/41
$179,900 Open House 4/12
- 2 Beds
- 2 Baths
- 1,152 Sq Ft
238 Palm Air Dr, Osprey, FL 34229

AN ARBORS BEAUTY in one of Florida’s most-sought-after 55+ parks. You won’t believe how BIG and BEAUTIFUL this home is !! Over 1,152 square feet of centrally-cooled comfort. Large living room. New laminate flooring. A chef’s kitchen. Comfy throughout. 2 LANAIS: (1) Front lanai with new windows and new tile flooring; (2) Side lanai is carpeted, screened and ready for relaxing. Both lanais add more

John Alexander FINE PROPERTIES

238 Palm Air Dr, Osprey, FL 34229
/2
$880,000 Sold Jan 30, 2026

392 Park Trace Blvd, Osprey, FL 34229
- 4 Beds
- 3 Baths
- 2,802 Sq Ft
- Built 2001
Last Sold Summary
- 6% Below List Price
- $314/SF
- 32 Days On Market
Current Estimated Value $871,172

Last Listing Agent Ryan Skrzypkowski COLDWELL BANKER REALTY

392 Park Trace Blvd, Osprey, FL 34229

/2
Est $1,874,429 Not Listed For Sale

676 Eagle Watch Ln, Osprey, FL 34229
- 5 Beds
- 5.5 Baths
- 5,399 Sq Ft
- Built 1992
676 Eagle Watch Ln, Osprey, FL 34229

Last Sold Summary
- 14% Above List Price
- $306/SF
- 12 Days On Market
Last Sold Price $1,650,000

Last Listing Agent Jamie Mullis COLDWELL BANKER REALTY

/45
$649,000 Pending
- 3 Beds
- 2.5 Baths
- 2,292 Sq Ft
659 Rivendell Blvd, Osprey, FL 34229

Under contract-accepting backup offers. Located within The Woodlands at Rivendell, this meticulously maintained single-family residence offers a sophisticated balance of comfort, functionality, and tranquil natural surroundings. Backing to a serene lake and protected preserve, the home enjoys exceptional privacy and peaceful water views. Designed with an open, split-bedroom floor plan, the

Stephanie Church COLDWELL BANKER REALTY

659 Rivendell Blvd, Osprey, FL 34229
/2
$85,000 Sold May 23, 2025

199 Palm Air Dr, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 959 Sq Ft
- Built 1978
Last Sold Summary
- 15% Below List Price
- $89/SF
- 87 Days On Market
Last Listing Agent Allison Bollero KELLER WILLIAMS ISLAND LIFE REAL ESTATE

199 Palm Air Dr, Osprey, FL 34229

/2
Est $253,741 Not Listed For Sale

104 Woodland Place, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,316 Sq Ft
- Built 1979
104 Woodland Place, Osprey, FL 34229

Last Sold Summary
- 14% Below List Price
- $224/SF
Last Sold Price $295,000

Last Listing Agent Stellar Non-Member Agent FL_MFRMLS

/98
$1,590,000
- 3 Beds
- 4.5 Baths
- 4,364 Sq Ft
76 Osprey Point Dr, Osprey, FL 34229

COMPLETELY UPGRADED IS NOT AN EXAGGERATION! This Bo MacEwen–designed 3-bedroom, 4.5-bath home has been updated from top (RE-TILED ROOF) to bottom, with new luxury flooring surfaces throughout and over $650,000 in renovations. No expense was spared in creating a refined, sophisticated residence that still feels warm and inviting. This home truly shows like new, and a full upgrade list is available

Steve Abbe COLDWELL BANKER REALTY

76 Osprey Point Dr, Osprey, FL 34229
/66
$155,000 Sold May 15, 2025

767 Pine Run Dr, Osprey, FL 34229
- 1 Bed
- 1 Bath
- 736 Sq Ft
- Built 1973
Last Sold Summary
- $211/SF
- 4 Days On Market
Current Estimated Value $151,326

Last Listing Agent Priscilla Adams COMPASS FLORIDA LLC

767 Pine Run Dr, Osprey, FL 34229

/25
Est $554,283 Not Listed For Sale

846 Oak Pond Dr, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 2,126 Sq Ft
- Built 1995
846 Oak Pond Dr, Osprey, FL 34229

Last Sold Summary
- 5% Below List Price
- $275/SF
- 113 Days On Market
Last Sold Price $585,000

Last Listing Agent Janet Oberholtzer Michael Saunders

/91
$1,999,999 Pending
- 3 Beds
- 3.5 Baths
- 2,473 Sq Ft
140 N Casey Key Rd, Osprey, FL 34229

Now offered under $2M on the coveted Casey Key barrier island, this elevated waterfront retreat captures sweeping open-bay views the moment you walk through the door. Positioned along the Intracoastal Waterway, the home offers a front-row seat to boating activity, kayaking, coastal birds, and even dolphins gliding across the water - while remaining just far enough away to enjoy peaceful privacy.

Rhonda Carder EXP REALTY LLC

140 N Casey Key Rd, Osprey, FL 34229
/2
$4,040,000 Sold Jan 05, 2026

1049 N Casey Key Rd, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,582 Sq Ft
- Built 1990
Last Sold Summary
- 15% Below List Price
- $1,565/SF
- 212 Days On Market
Current Estimated Value $3,690,599

Last Listing Agent Courtney Green PREMIER SOTHEBYS INTL REALTY

1049 N Casey Key Rd, Osprey, FL 34229

/79
Est $571,983 Not Listed For Sale

587 Meadow Sweet Cir, Osprey, FL 34229
- 3 Beds
- 2.5 Baths
- 2,217 Sq Ft
- Built 1996
587 Meadow Sweet Cir, Osprey, FL 34229

Last Sold Summary
- 15% Below List Price
- $304/SF
- 16 Days On Market
Last Sold Price $675,000

Last Listing Agent Priscilla Adams COMPASS FLORIDA LLC

/96
$3,250,000
- 3 Beds
- 3.5 Baths
- 2,665 Sq Ft
14401 Masthead Dr, Osprey, FL 34229

Unobstructed bayfront views and refined coastal luxury define this exceptional waterfront residence in the gated Bayside community. Custom-built in 2017 by Rob Allegra and ideally positioned on a private cul-de-sac between Sarasota and Venice, this home offers a rare opportunity to experience the best of Florida’s Gulf Coast lifestyle. Sweeping views of the Bay and Intracoastal Waterway greet you

Mackenzie Longueuil MICHAEL SAUNDERS & COMPANY

14401 Masthead Dr, Osprey, FL 34229
/2
$625,000 Sold Jul 26, 2025

695 Rivendell Blvd, Osprey, FL 34229
- 4 Beds
- 3 Baths
- 2,256 Sq Ft
- Built 2001
Last Sold Summary
- 4% Below List Price
- $277/SF
- 1 Day On Market
Current Estimated Value $633,363

Last Listing Agent Dan Henson DALTON WADE INC

695 Rivendell Blvd, Osprey, FL 34229

/2
Est $503,456 Not Listed For Sale

230 Burney Rd, Osprey, FL 34229
- 4 Beds
- 3 Baths
- 2,219 Sq Ft
- Built 1985
230 Burney Rd, Osprey, FL 34229

Last Sold Summary
- 30% Above List Price
- $175/SF
- 2 Days On Market
Last Sold Price $388,600

Last Listing Agent Xiaoguang Ruan AAA GLOBAL VENTURES PA

/40
$4,250,000
- 4 Beds
- 4.5 Baths
- 4,389 Sq Ft
324 Bayshore Dr, Osprey, FL 34229

Big bay views surround you from this exquisitely updated waterfront estate. Welcome to 324 Bayshore Drive, a property of nearly half an acre set on a large, open stretch of the bay with easy access to the Intracoastal Waterway. Even more spectacular is the beautiful water and natural beauty of Midnight Pass which is just to the north of this property and sandbar relaxation just a short boat ride

Drew Russell MICHAEL SAUNDERS & COMPANY

324 Bayshore Dr, Osprey, FL 34229
/2
$559,500 Sold Apr 04, 2025

1219 Chalet Ct, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 2,165 Sq Ft
- Built 2004
Last Sold Summary
- 4% Below List Price
- $258/SF
- 56 Days On Market
Current Estimated Value $567,079

Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

1219 Chalet Ct, Osprey, FL 34229

/64
Est $546,189 Not Listed For Sale

128 Villa Dr Unit 128, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,404 Sq Ft
- Built 1978
128 Villa Dr Unit 128, Osprey, FL 34229

Last Sold Summary
- 19% Below List Price
- $480/SF
- 67 Days On Market
Last Sold Price $674,000

Last Listing Agent Raphael Carlisi FINE PROPERTIES

/96
$1,500,000
- 3 Beds
- 3 Baths
- 2,778 Sq Ft
385 N Point Rd Unit 704, Osprey, FL 34229

Experience breathtaking views of the Bay and Gulf from this spacious 3 bedroom, 3 bath end unit, featuring a separate dining room and den. Completely updated and meticulously maintained, this unit is beautifully appointed and custom features abound. A private elevator takes you to a majestic foyer which opens to the great room. Facing west the views are gorgeous from sunrise to sunset. The

Steve Abbe COLDWELL BANKER REALTY

385 N Point Rd Unit 704, Osprey, FL 34229
/2
$545,000 Sold Mar 31, 2026

711 Shadow Bay Way, Osprey, FL 34229
- 4 Beds
- 2 Baths
- 2,133 Sq Ft
- Built 2002
Last Sold Summary
- 9% Below List Price
- $256/SF
- 77 Days On Market
Current Estimated Value $584,390

Last Listing Agent Susan Keal MICHAEL SAUNDERS & COMPANY

711 Shadow Bay Way, Osprey, FL 34229

/70
Est $668,314 Not Listed For Sale

433 S Shore Dr, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 1,868 Sq Ft
- Built 1984
433 S Shore Dr, Osprey, FL 34229

Last Sold Summary
- 1% Above List Price
- $353/SF
- 72 Days On Market
Last Sold Price $660,000

Last Listing Agent Christine Pope Michael Saunders

/65
$6,475,000
- 4 Beds
- 5.5 Baths
- 4,096 Sq Ft
121 N Casey Key Rd, Osprey, FL 34229

Directly on the turquoise waters of the Gulf, this newly remodeled Spanish Mediterranean estate on the north end of Casey Key offers the rare privilege of a private beach just steps from the home. Set on one of Florida’s most exclusive barrier islands, the property enjoys sweeping sunset views, exceptional privacy, and convenient access to the dining, shopping, and cultural attractions of Venice

Lisa Napolitano DOUGLAS ELLIMAN

121 N Casey Key Rd, Osprey, FL 34229

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