Osprey, FL Homes

/70
$2,249,900
- 5 Beds
- 3.5 Baths
- 3,236 Sq Ft
180 Lookout Point Dr, Osprey, FL 34229

One or more photo(s) has been virtually staged. Welcome to 180 Lookout Point Drive in the sought-after Southbay Yacht & Racquet Club with deep water marina and available boat slips, the opportunity to walk to your boat in a deep water marina with your home resting safely in Flood Zone X (where flood insurance is not even required by lenders) doesn't come along often. This is an extraordinary

Katy McBrayer PREMIER SOTHEBY'S INTERNATIONAL REALTY

180 Lookout Point Dr, Osprey, FL 34229
/2
$1,700,000 Sold Jun 12, 2025

525 S Shore Dr, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,315 Sq Ft
- Built 1972
Last Sold Summary
- 15% Below List Price
- $734/SF
- 108 Days On Market
Current Estimated Value $1,652,487

Last Listing Agent Andree Huffine COLDWELL BANKER REALTY

525 S Shore Dr, Osprey, FL 34229

/2
Est $999,873 Not Listed For Sale

434 N Shore Dr, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,932 Sq Ft
- Built 1989
434 N Shore Dr, Osprey, FL 34229

Last Sold Summary
- 11% Above List Price
- $307/SF
- 254 Days On Market
Last Sold Price $900,000

Last Listing Agent Victoria Stultz ENGEL + VOELKERS SARASOTA

/92
$850,000
- 3 Beds
- 2 Baths
- 2,246 Sq Ft
21 Bayhead Ln, Osprey, FL 34229

Looking for a home you can fall in love with? The search is over! Once you see this thoughtfully updated, impeccably maintained 3 bedroom, 2 bath home in The Oaks Preserve you will know you have found your home-sweet-home. From the moment you pull up to the pavered driveway, the care taken to maintain this property is evident. Walk past the two-car garage to the pretty, double front doors with

Steve Abbe COLDWELL BANKER REALTY

21 Bayhead Ln, Osprey, FL 34229
/2
$750,000 Sold Dec 30, 2025

523 Habitat Blvd, Osprey, FL 34229
- 4 Beds
- 3 Baths
- 2,314 Sq Ft
- Built 2003
Last Sold Summary
- 5% Below List Price
- $324/SF
- 122 Days On Market
Current Estimated Value $745,010

Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

523 Habitat Blvd, Osprey, FL 34229

/29
Est $2,160,980 Not Listed For Sale

162 Puesta Del Sol, Osprey, FL 34229
- 4 Beds
- 4.5 Baths
- 4,747 Sq Ft
- Built 2003
162 Puesta Del Sol, Osprey, FL 34229

Last Sold Summary
- 6% Below List Price
- $485/SF
- 3 Days On Market
Last Sold Price $2,300,000

Last Listing Agent Drew Russell Michael Saunders

/58
$399,000
- 2 Beds
- 2 Baths
- 1,479 Sq Ft
291 Hidden Bay Dr Unit 102, Osprey, FL 34229

In the lush and serene grounds of this private and peaceful community is a best-kept secret with a name that says it all. Within Hidden Bay, this condominium gem resides in a spot on the community lake with a stunning view and soothing sound of waterfalls from your own enclosed lanai. Fully furnished with mostly all new furniture in the owners’ suite, including a new king-size mattress, living

Pat McMillan PREMIER SOTHEBY'S INTERNATIONAL REALTY

291 Hidden Bay Dr Unit 102, Osprey, FL 34229
/2
$799,000 Sold Mar 09, 2026

529 Habitat Blvd, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,617 Sq Ft
- Built 2003
Last Sold Summary
- $305/SF
- 2 Days On Market
Current Estimated Value $793,545

Last Listing Agent Todd Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

529 Habitat Blvd, Osprey, FL 34229

/84
Est $1,392,858 Not Listed For Sale

513 S Creek Dr, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,556 Sq Ft
- Built 1980
513 S Creek Dr, Osprey, FL 34229

Last Sold Summary
- 5% Above List Price
- $518/SF
- 13 Days On Market
Last Sold Price $1,325,000

Last Listing Agent Brandi Furlan KW COASTAL LIVING III

/99
$1,345,000 Pending
- 4 Beds
- 3 Baths
- 3,303 Sq Ft
137 Osprey Point Dr, Osprey, FL 34229

Under contract-accepting backup offers. Although built in the 20th century, this home looks as authentic as the French manor house it was modeled after. The façade features a soft, light-colored stucco exterior accented by rustic stonework, creating a warm and inviting presence. Gracefully arched windows and classic dormers enhance the wooden shingle roof, which is crowned by two stately chimneys

Steve Abbe COLDWELL BANKER REALTY

137 Osprey Point Dr, Osprey, FL 34229
/2
$550,000 Sold Mar 23, 2026

510 Latitude Ln, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 2,298 Sq Ft
- Built 2004
Last Sold Summary
- 13% Below List Price
- $239/SF
- 125 Days On Market
Current Estimated Value $600,651

Last Listing Agent Marisa Marino BRIGHT REALTY

510 Latitude Ln, Osprey, FL 34229

/2
Est $210,456 Not Listed For Sale

120 Woodland Place Unit 120, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,325 Sq Ft
- Built 1979
120 Woodland Place Unit 120, Osprey, FL 34229

Last Sold Summary
- $158/SF
- 100 Days On Market
Last Sold Price $210,000

Last Listing Agent Maurice Menager Michael Saunders

/95
$1,380,000 Open Sat 12PM - 2PM
- 3 Beds
- 2 Baths
- 1,824 Sq Ft
365 S Shore Dr, Osprey, FL 34229

Wake up to ever-changing INTRACOASTAL VIEWS – SUNSETS dancing across the water, BOATS gliding by, and untouched wildlife. Set on an EXTRA-DEEP WATER FRONT LOT with GULF ACCESS, this exceptional residence offers a rare blend of privacy, sweeping WATERFRONT views, timeless COASTAL DESIGN, and a DOCK WITH A 10,000LB BOAT LIFT that places open water just minutes away. A BOATERS PARADISE, this refined

Lisa Asaro EXIT KING REALTY

365 S Shore Dr, Osprey, FL 34229
/2
$715,000 Sold Mar 17, 2026

319 Park Trace Blvd, Osprey, FL 34229
- 4 Beds
- 3 Baths
- 2,551 Sq Ft
- Built 2000
Last Sold Summary
- 5% Below List Price
- $280/SF
- 33 Days On Market
Current Estimated Value $747,103

Last Listing Agent Megan George PREMIER SOTHEBYS INTL REALTY

319 Park Trace Blvd, Osprey, FL 34229

/2
Est $692,032 Not Listed For Sale

1192 Mallard Marsh Dr, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,695 Sq Ft
- Built 2002
1192 Mallard Marsh Dr, Osprey, FL 34229

Last Sold Summary
- 5% Above List Price
- $245/SF
- 191 Days On Market
Last Sold Price $660,000

Last Listing Agent Marie Fogarty M H FOGARTY AND COMPANY LLC

/7
$269,999
- Land
- 0.13 Acre
- $2,076,915 per Acre
456 Washington Ave, Osprey, FL 34229

Owner Financing is Available. Prime Land at 456 Washington Ave, Osprey, FL 34229 – A Rare Gem Near Historic Spanish Point & Selby Gardens. Don’t miss out on this incredible opportunity to own a prime piece of land at 456 Washington Ave, located in the heart of Osprey, FL. Surrounded by natural beauty and rich history, this property is just moments from the renowned Historic Spanish Point and the

Mike Vo FLOTACAL

456 Washington Ave, Osprey, FL 34229
/2
$1,160,000 Sold Apr 15, 2025

131 Tina Island Dr, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 1,787 Sq Ft
- Built 1978
Last Sold Summary
- 7% Below List Price
- $649/SF
- 10 Days On Market
Current Estimated Value $1,148,712

Last Listing Agent Sarah McGuire WHITE SANDS REALTY GROUP FL

131 Tina Island Dr, Osprey, FL 34229

/2
Est $556,503 Not Listed For Sale

685 Clear Creek Dr, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 2,204 Sq Ft
- Built 2002
685 Clear Creek Dr, Osprey, FL 34229

Last Sold Summary
- 5% Above List Price
- $240/SF
- 10 Days On Market
Last Sold Price $530,000

Last Listing Agent Brian ODonnell,PLLC REALTY BY DESIGN LLC

/25
$109,000
- 2 Beds
- 2 Baths
- 864 Sq Ft
348 Tropic Dr, Osprey, FL 34229

Perfect Home for a SNOW BIRD OR A "YEAR-ROUNDER "!! The Arbors is the BEST of the Florida sun belt communities. THE ROOF -- New in 2022 with 15-Year Transferable Waranty. THE CARPORT -- New 2023 No leaks. This lovingly maintained manufactured home is in a PET FRIENDLY zone. Your LOW $215/month HOA provides: YOUR Water. YOUR Sewer. YOUR Lawn care. YOUR Cable service. A lucky buyer could move in

John Alexander FINE PROPERTIES

348 Tropic Dr, Osprey, FL 34229
/2
$645,000 Sold Jul 31, 2025

673 Crane Prairie Way, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,223 Sq Ft
- Built 2003
Last Sold Summary
- 13% Below List Price
- $290/SF
- 9 Days On Market
Current Estimated Value $654,342

Last Listing Agent Laura Harris, PA PREMIER SOTHEBYS INTL REALTY

673 Crane Prairie Way, Osprey, FL 34229

/2
Est $902,453 Not Listed For Sale

1200 Mallard Marsh Dr, Osprey, FL 34229
- 4 Beds
- 3 Baths
- 2,928 Sq Ft
- Built 2002
1200 Mallard Marsh Dr, Osprey, FL 34229

Last Sold Summary
- 2% Below List Price
- $316/SF
- 118 Days On Market
Last Sold Price $925,000

Last Listing Agent Sharon Osborne, PA RESULTS REALTY GROUP LLC

/59
$995,000
- 3 Beds
- 3 Baths
- 2,055 Sq Ft
409 N Point Rd Unit 902, Osprey, FL 34229

**A RARE OFFERING, 9TH FLOOR, UPDATED PENTHOUSE with PRIVATE 2-CAR GARAGE** Enjoy the ultimate unobstructed views of Little Sarasota Bay that includes the Gulf of Mexico & Midnight Pass with Casey Key and Siesta Key in the vista. This upper-level Penthouse condo offers a tranquil, quiet residence that transports you to another world high above the preserve and waterways where birds dance and dive

Mark Lyda GENEROUS PROPERTY

409 N Point Rd Unit 902, Osprey, FL 34229
/2
$362,500 Sold Feb 23, 2026

291 Hidden Bay Dr Unit 101, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,599 Sq Ft
- Built 2000
Last Sold Summary
- 9% Below List Price
- $227/SF
- 58 Days On Market
Current Estimated Value $378,063

Last Listing Agent Stephanie Ham PARADISE EXCLUSIVE INC

291 Hidden Bay Dr Unit 101, Osprey, FL 34229

/2
Est $834,875 Not Listed For Sale

1030 Scherer Way, Osprey, FL 34229
- 4 Beds
- 3 Baths
- 2,433 Sq Ft
- Built 2003
1030 Scherer Way, Osprey, FL 34229

Last Sold Summary
- 10% Below List Price
- $380/SF
- 10 Days On Market
Last Sold Price $925,000

Last Listing Agent Kimberly Young BERKSHIRE HATHAWAY HOMESERVICE

/93
$885,000
- 2 Beds
- 2 Baths
- 2,071 Sq Ft
227 Saint James Park, Osprey, FL 34229

Experience the charm and wonderful location of this golf course home on Saint James Park, the leafy and quiet cul-de-sac where you can walk to tennis, golf, pickleball, croquet, heated pool and state of the art fitness center all within The Oaks Country Club, where the luxury lifestyle awaits! This 2 bedroom, 2 bath traditional home overlooks the first hole of the Eagle Golf course, and is being

Rosalie Phillips MICHAEL SAUNDERS & COMPANY

227 Saint James Park, Osprey, FL 34229
/2
$390,000 Sold Apr 15, 2025

441 N Shore Dr, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,334 Sq Ft
- Built 1970
Last Sold Summary
- 18% Below List Price
- $292/SF
- 21 Days On Market
Current Estimated Value $376,333

Last Listing Agent Dawn Barnett EXIT KING REALTY

441 N Shore Dr, Osprey, FL 34229

/55
Est $949,302 Not Listed For Sale

792 Placid Lake Dr, Osprey, FL 34229
- 4 Beds
- 3 Baths
- 3,360 Sq Ft
- Built 2003
792 Placid Lake Dr, Osprey, FL 34229

Last Sold Summary
- 12% Below List Price
- $320/SF
- 2 Days On Market
Last Sold Price $1,075,000

Last Listing Agent Helena Nordstrom PREMIER SOTHEBY'S INTERNATIONAL REALTY

/49
$2,000,000
- 3 Beds
- 2 Baths
- 1,977 Sq Ft
18 N Casey Key Rd, Osprey, FL 34229

Elegantly renovated bayfront retreat on Casey Key and tastefully remodeled in 2012, this stunning bayfront home blends timeless coastal elegance with modern functionality, all in one of the desired locations on Casey Key. Designed for relaxing and entertaining, the open-concept living room, kitchen, and family room offer inviting spaces to gather, while the split floor plan ensures privacy, ideal

Valerie Dall'acqua PREMIER SOTHEBY'S INTERNATIONAL REALTY

18 N Casey Key Rd, Osprey, FL 34229
/2
$2,315,000 Sold Oct 30, 2025

112 Osprey Point Dr, Osprey, FL 34229
- 4 Beds
- 5.5 Baths
- 8,635 Sq Ft
- Built 1989
Last Sold Summary
- 41% Below List Price
- $268/SF
- 156 Days On Market
Current Estimated Value $2,909,004

Last Listing Agent Kara Money KARA MONEY LLC

112 Osprey Point Dr, Osprey, FL 34229

/40
Est $734,232 Not Listed For Sale

669 Crane Prairie Way, Osprey, FL 34229
- 4 Beds
- 3 Baths
- 2,323 Sq Ft
- Built 2003
669 Crane Prairie Way, Osprey, FL 34229

Last Sold Summary
- 15% Below List Price
- $373/SF
- 2 Days On Market
Last Sold Price $867,000

Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

/100
$1,600,000
- 3 Beds
- 3.5 Baths
- 3,872 Sq Ft
422 Blue Garden Ln, Osprey, FL 34229

A grand traditional residence, this 3-bedroom, 3.5-bath home is tucked into lush tropical landscaping on a quiet cul-de-sac in The Oaks Bayside. Double entry doors open to a marble foyer and wood floors that set the tone for quality throughout. Just off the entry, a cozy den with fireplace sits opposite a spacious guest suite. The heart of the home is the light-filled great room, with formal

Steve Abbe COLDWELL BANKER REALTY

422 Blue Garden Ln, Osprey, FL 34229
/2
$665,000 Sold Nov 06, 2025

563 Pine Ranch Rd E, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 2,346 Sq Ft
- Built 1997
Last Sold Summary
- 1% Below List Price
- $283/SF
- 5 Days On Market
Current Estimated Value $658,372

Last Listing Agent Kevin Stanley, P.A. PREMIER SOTHEBYS INTL REALTY

563 Pine Ranch Rd E, Osprey, FL 34229

/2
Est $650,955 Not Listed For Sale

1109 Scherer Way, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 2,125 Sq Ft
- Built 2002
1109 Scherer Way, Osprey, FL 34229

Last Sold Summary
- 1% Below List Price
- $309/SF
- 61 Days On Market
Last Sold Price $656,000

Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

/19
$422,000
- 2 Beds
- 2 Baths
- 1,725 Sq Ft
1811 Highland Rd, Osprey, FL 34229

PRIVATE NEIGHBORHOOD - Fully Furnished 2 Bedroom Townhouse in the Casey Key area, QUAINT, SPACIOUS 2-CAR Tandem GARAGE + Carport, modern, high ceilings, kitchen upgrades, screened balcony, 2 beds + den; 2 baths; living area and kitchen open plan; community pool Conveniently located between Sarasota, Siesta Key, Venice, and the Gulf Beaches.Walking distance to Casey Key Mainland (Chef Rolfs),

Stephen Hachey REALTY OF RIVERVIEW LLC

1811 Highland Rd, Osprey, FL 34229
/2
$1,500,000 Sold Sep 19, 2025

462 E MacEwen Dr, Osprey, FL 34229
- 3 Beds
- 2.5 Baths
- 2,611 Sq Ft
- Built 1998
Last Sold Summary
- 3% Below List Price
- $574/SF
- 29 Days On Market
Current Estimated Value $1,470,122

Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

462 E MacEwen Dr, Osprey, FL 34229

/2
Est $577,774 Not Listed For Sale

825 Oak Pond Dr, Osprey, FL 34229
- 4 Beds
- 3 Baths
- 2,229 Sq Ft
- Built 1996
825 Oak Pond Dr, Osprey, FL 34229

Last Sold Summary
- 5% Below List Price
- $274/SF
- 25 Days On Market
Last Sold Price $610,000

Last Listing Agent Magda Cetta Whelton ENGEL & VOELKERS VENICE DOWNTOWN

/46
$2,450,000 Pending
- 4 Beds
- 5.5 Baths
- 4,858 Sq Ft
896 MacEwen Dr, Osprey, FL 34229

Under contract-accepting backup offers. This beautiful custom designed home will captivate you from the moment you enter the front door. Located in the extremely sought after Oaks Country Club, this recently renovated home is sure to impress with picturesque views of the golf course. Privacy and entertaining are at the top of the list for this tastefully remodeled home, offering 4 bedrooms and 5

Marisa Marino BRIGHT REALTY

896 MacEwen Dr, Osprey, FL 34229
/2
$290,000 Sold Apr 07, 2025

427 Washington Ave, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 1,120 Sq Ft
- Built 1957
Last Sold Summary
- 11% Below List Price
- $259/SF
- 195 Days On Market
Current Estimated Value $293,845

Last Listing Agent Kelly Jenkins KW COASTAL LIVING II

427 Washington Ave, Osprey, FL 34229

/48
Est $595,138 Not Listed For Sale

522 Meadow Sweet Cir, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 2,424 Sq Ft
- Built 1998
522 Meadow Sweet Cir, Osprey, FL 34229

Last Sold Summary
- 13% Below List Price
- $284/SF
- 145 Days On Market
Last Sold Price $687,500

Last Listing Agent Sandi Tresh RE/MAX

/94
$990,000
- 3 Beds
- 3 Baths
- 2,778 Sq Ft
401 N Point Rd Unit 504, Osprey, FL 34229

FULLY UPDATED • WATER VIEWS • PRIVATE 2-CAR GARAGE • OFFICE/4TH BEDROOM OPTION From the moment the private elevator opens into your foyer, this residence reveals itself as a home crafted with intention, artistry, and a deep appreciation for its natural surroundings. Sunlight fills the space as water and preserve views stretch out beyond the generous lanai—an ever-changing backdrop that greets you

Mary Elizabeth Mock COLDWELL BANKER REALTY

401 N Point Rd Unit 504, Osprey, FL 34229

Showing Results 321 - 360, Page 9 of 18

Florida Sarasota County Osprey

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