Homes in ZIP Code 34229

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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
$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 $307,180

Last Listing Agent EJ Stukenborg KELLER WILLIAMS ON THE WATER S

115 Villa Dr Unit 115, Osprey, FL 34229

/2
Est $640,242 Not Listed For Sale

385 N Point Rd Unit 602, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,055 Sq Ft
- Built 2000
385 N Point Rd Unit 602, Osprey, FL 34229

Last Sold Summary
- 2% Below List Price
- $316/SF
- 174 Days On Market
Last Sold Price $650,000

Last Listing Agent Matt Buttner LIST NOW REALTY, LLC

/83
$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. If your dream is to create a place where generations can gather, relax, and make lasting memories, this Casey Key estate is ready to welcome you home. Set on 0.68 acres with 131 feet of Sarasota Bay frontage, this 4 bed 4.5 bath retreat offers room to spread out, unwind, and connect indoors and out. Each bedroom opens to the outdoors with bay

Brandy Sheldon COLDWELL BANKER REALTY

1042 N Casey Key Rd, 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 $506,089 Not Listed For Sale

515 Oak Bay Dr, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 1,977 Sq Ft
- Built 1995
515 Oak Bay Dr, Osprey, FL 34229

Last Sold Summary
- 1% Below List Price
- $259/SF
- 116 Days On Market
Last Sold Price $512,500

Last Listing Agent Thomas Cail RE/MAX

/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
$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 $1,117,395

Last Listing Agent Lisa Napolitano DOUGLAS ELLIMAN

327 Sea Anchor Dr, Osprey, FL 34229

/34
Est $594,698 Not Listed For Sale

1358 Thornapple Dr, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 2,163 Sq Ft
- Built 2003
1358 Thornapple Dr, Osprey, FL 34229

Last Sold Summary
- 2% Below List Price
- $280/SF
- 86 Days On Market
Last Sold Price $605,000

Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

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

Under contract-accepting backup offers. 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

Jennie Lascelle PREFERRED SHORE LLC

408 Park Trace Blvd, 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 $649,680

Last Listing Agent Kim Azar-Calka MICHAEL SAUNDERS & COMPANY

455 Park Trace Blvd, Osprey, FL 34229

/42
Est $552,166 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
- 6% Below List Price
- $284/SF
- 69 Days On Market
Last Sold Price $590,000

Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

/59
$585,000 Pending
- 4 Beds
- 2 Baths
- 2,133 Sq Ft
711 Shadow Bay Way, Osprey, FL 34229

Under contract-accepting backup offers. Condition, Condition, Condition – AND Location, Location, Location!! This house is a real gem! Immaculate and beautifully updated, it features 4 bedrooms (or 3 plus a den with a closet) in a split plan that provides privacy for owners and guests. When you sit on the front porch of this contemporary style home, you’ll enjoy an uninterrupted front yard, since

Susan Keal MICHAEL SAUNDERS & COMPANY

711 Shadow Bay Way, 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 $924,801

Last Listing Agent Ryan Skrzypkowski COLDWELL BANKER REALTY

392 Park Trace Blvd, Osprey, FL 34229

/3
Est $645,696 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
- 11% 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

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

Under contract-accepting backup offers. 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

Tiffany Stonis EXP REALTY LLC

742 Harms Dr, 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

/85
Est $949,494 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
- 3% Below List Price
- $287/SF
- 52 Days On Market
Last Sold Price $980,000

Last Listing Agent Mark Klecka COLDWELL BANKER REALTY

/41
$179,900 Open Sun 2PM - 4PM
- 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
/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 $168,802

Last Listing Agent Priscilla Adams COMPASS FLORIDA LLC

767 Pine Run Dr, Osprey, FL 34229

/2
Est $1,531,641 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
- 6% Above List Price
- $314/SF
- 193 Days On Market
Last Sold Price $1,450,000

Last Listing Agent Steve Abbe 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
$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 $3,639,473

Last Listing Agent Courtney Green PREMIER SOTHEBYS INTL REALTY

1049 N Casey Key Rd, Osprey, FL 34229

/2
Est $1,209,428 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
- 1% Above List Price
- $295/SF
- 8 Days On Market
Last Sold Price $1,200,000

Last Listing Agent Tina Timmons ROSEBAY INTERNATIONAL REALTY, INC

/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
/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 $619,359

Last Listing Agent Dan Henson DALTON WADE INC

695 Rivendell Blvd, Osprey, FL 34229

/2
Est $950,455 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
- 5% Below List Price
- $380/SF
Last Sold Price $999,500

Last Listing Agent Susanne Losso COLDWELL BANKER REALTY

/83
$1,299,000
- 3 Beds
- 3.5 Baths
- 3,112 Sq Ft
156 Bishopscourt Rd, Osprey, FL 34229

This stunning three-bedroom, 3.5 bath home, designed by the renowned architect Frank Folsom Smith, stands out with its unique design. This charming Cape Cod sets the stage for comfortable, gracious living, enjoying private preserve views. A Sonos sound system plays throughout this gorgeous home! Sit back and enjoy a peaceful afternoons and twilight dinners on the lovely newly screened Florida

Steve Abbe COLDWELL BANKER REALTY

156 Bishopscourt Rd, 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 $545,672

Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

1219 Chalet Ct, Osprey, FL 34229

/2
Est $1,781,012 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
- 8% Above List Price
- $306/SF
- 12 Days On Market
Last Sold Price $1,650,000

Last Listing Agent Jamie Mullis COLDWELL BANKER REALTY

/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
$1,197,000 Sold May 30, 2025

223 Saint James Park, Osprey, FL 34229
- 3 Beds
- 5 Baths
- 3,321 Sq Ft
- Built 1991
Last Sold Summary
- 8% Below List Price
- $360/SF
- 20 Days On Market
Current Estimated Value $1,152,747

Last Listing Agent John Hockenberry RE/MAX ALLIANCE GROUP

223 Saint James Park, Osprey, FL 34229

/2
Est $251,053 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
- 15% Below List Price
- $224/SF
Last Sold Price $295,000

Last Listing Agent Stellar Non-Member Agent FL_MFRMLS

/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
$520,000 Sold Nov 14, 2025

708 Anna Hope Ln, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 2,133 Sq Ft
- Built 2002
Last Sold Summary
- 5% Below List Price
- $244/SF
- 8 Days On Market
Current Estimated Value $524,784

Last Listing Agent Julien Collet PINEYWOODS REALTY LLC

708 Anna Hope Ln, Osprey, FL 34229

/25
Est $546,388 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
- 7% Below List Price
- $275/SF
- 113 Days On Market
Last Sold Price $585,000

Last Listing Agent Janet Oberholtzer Michael Saunders

/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
/62
$560,000 Sold May 29, 2025

221 Sorrento Dr, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 1,935 Sq Ft
- Built 1984
Last Sold Summary
- 10% Below List Price
- $289/SF
- 68 Days On Market
Current Estimated Value $550,807

Last Listing Agent Glenn Davis COLDWELL BANKER SARASOTA CENT.

221 Sorrento Dr, Osprey, FL 34229

/79
Est $569,852 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
- 16% Below List Price
- $304/SF
- 16 Days On Market
Last Sold Price $675,000

Last Listing Agent Priscilla Adams COMPASS FLORIDA LLC

/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

Showing Results 441 - 480, Page 12 of 18

Florida Sarasota County Osprey 34229

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Homes in ZIP Code 34229

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