Osprey, FL Homes

/53
$650,000
- 4 Beds
- 2 Baths
- 1,893 Sq Ft
745 Fordingbridge Way, Osprey, FL 34229

Welcome to this beautiful home in the sought-after Rivendell community. The curb appeal is evident as you drive up to this home, from the landscape and the paver driveway to the beautiful front door. As you step inside the wide foyer, your view extends out through the sliders leading out to the pool and lanai. This well-maintained updated residence combines a bright, inviting interior designed

Janet Oberholtzer MICHAEL SAUNDERS & COMPANY

745 Fordingbridge Way, Osprey, FL 34229
/2
$479,000 Sold Sep 10, 2025

26 Bay Acres Ave, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 1,904 Sq Ft
- Built 1971
Last Sold Summary
- $252/SF
- 6 Days On Market
Current Estimated Value $506,993

Last Listing Agent Erica Giesler RE/MAX ALLIANCE GROUP

26 Bay Acres Ave, Osprey, FL 34229

/25
Est $546,846 Not Listed For Sale

543 Meadow Sweet Cir, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 1,981 Sq Ft
- Built 2001
543 Meadow Sweet Cir, Osprey, FL 34229

Last Sold Summary
- 8% Below List Price
- $299/SF
- 52 Days On Market
Last Sold Price $592,500

Last Listing Agent Mary Jo Violett Michael Saunders

/13
$548,000
- 4 Beds
- 2 Baths
- 1,861 Sq Ft
4428 Conchfish Ln, Osprey, FL 34229

Chic Modern Escape in the Heart of Palms at Casey Key! This charming residence is located in a flood zone that is not considered a high-risk zone (Zone X) and features four spacious bedrooms and two full bathrooms, along with a two car garage and a large driveway for additional parking. Step into the kitchen, and you'll find elegant quartz countertops, upgraded 42" Timberlake latte cabinets, a

Mariana Georgieva HORIZON REALTY INTERNATIONAL

4428 Conchfish Ln, Osprey, FL 34229
/2
$766,000 Sold Aug 08, 2025

127 Park Trace Blvd, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 2,463 Sq Ft
- Built 2003
Last Sold Summary
- $311/SF
- 2 Days On Market
Current Estimated Value $758,488

Last Listing Agent Kim Azar-Calka MICHAEL SAUNDERS & COMPANY

127 Park Trace Blvd, Osprey, FL 34229

/64
Est $252,898 Not Listed For Sale

224 Woodland Dr, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,325 Sq Ft
- Built 1980
224 Woodland Dr, Osprey, FL 34229

Last Sold Summary
- 18% Below List Price
- $234/SF
- 133 Days On Market
Last Sold Price $310,000

Last Listing Agent Priscilla Adams COMPASS FLORIDA LLC

/61
$474,900
- 3 Beds
- 2 Baths
- 1,883 Sq Ft
7303 Jessie Harbor Dr Unit 7303, Osprey, FL 34229

PENTHOUSE CONDO IN WATERFRONT COMMUNITY!Experience luxury coastal living in this spacious 3-bedroom, 2-bath penthouse condo, perfectly situated on a tranquil canal with dockage and direct, bridge-free access to the Intracoastal Waterway and the Gulf. This impressive 3rd-floor residence features an open floor plan with expansive rooms, plantation shutters, and three private balconies—ideal for

Toy Coxey KW COASTAL LIVING

7303 Jessie Harbor Dr Unit 7303, Osprey, FL 34229
/2
$512,500 Sold Apr 07, 2025

1152 Beachcomber Ct Unit 15, Osprey, FL 34229
- 3 Beds
- 2.5 Baths
- 2,147 Sq Ft
- Built 2005
Last Sold Summary
- 10% Below List Price
- $239/SF
- 34 Days On Market
Current Estimated Value $486,098

Last Listing Agent Jennifer Bright BRIGHT REALTY

1152 Beachcomber Ct Unit 15, Osprey, FL 34229

/50
Est $1,031,143 Not Listed For Sale

206 Four Knot Ln, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 2,411 Sq Ft
- Built 1991
206 Four Knot Ln, Osprey, FL 34229

Last Sold Summary
- 55% Above List Price
- $276/SF
- 78 Days On Market
Last Sold Price $665,000

Last Listing Agent Peggy Lewis COLDWELL BANKER SARASOTA CENT.

/48
$895,000
- 3 Beds
- 3 Baths
- 2,283 Sq Ft
172 Sea Anchor Dr, Osprey, FL 34229

Amazing home with many improvements ideally located in a sought-after marina community. This beautifully updated 3-bedroom 3 bath residence has been thoughtfully enhanced for comfort, style and easy living. It's tucked inside a lively marina community where every day feels like vacation. This home features modern updates throughout. Newly remodeled kitchen, new master bath, luxury vinyl flooring,

Sharon Lewis GOLF & BAY PROPERTIES LLC

172 Sea Anchor Dr, Osprey, FL 34229
/2
$625,000 Sold Nov 07, 2025

594 Pine Ranch Rd E, Osprey, FL 34229
- 3 Beds
- 2.5 Baths
- 2,298 Sq Ft
- Built 1997
Last Sold Summary
- 4% Below List Price
- $272/SF
- 51 Days On Market
Current Estimated Value $613,684

Last Listing Agent Dan Henson DALTON WADE INC

594 Pine Ranch Rd E, Osprey, FL 34229

/59
Est $1,173,404 Not Listed For Sale

384 S Creek Ct, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 3,811 Sq Ft
- Built 1982
384 S Creek Ct, Osprey, FL 34229

Last Sold Summary
- 49% Above List Price
- $206/SF
- 71 Days On Market
Last Sold Price $785,000

Last Listing Agent Brandi Furlan KW COASTAL LIVING III

/4
$115,000
570 Blackburn Point Rd Unit LONGBOAT 43, Osprey, FL 34229

This slip will house a boat with the maximum dimensions of 27.5'L x 11'W x 11.5'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.

David Babel BRIGHT REALTY

570 Blackburn Point Rd Unit LONGBOAT 43, Osprey, FL 34229
/2
$160,000 Sold Mar 03, 2026

216 Palm Air Dr, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,055 Sq Ft
- Built 1983
Last Sold Summary
- 2% Below List Price
- $152/SF
- 71 Days On Market
Last Listing Agent Todd Goodman KELLER WILLIAMS ON THE WATER S

216 Palm Air Dr, Osprey, FL 34229

/99
Est $670,403 Not Listed For Sale

801 Oak Briar Ln, Osprey, FL 34229
- 4 Beds
- 3 Baths
- 2,330 Sq Ft
- Built 2004
801 Oak Briar Ln, Osprey, FL 34229

Last Sold Summary
- 11% Below List Price
- $322/SF
- 6 Days On Market
Last Sold Price $750,000

Last Listing Agent Christopher Costello RE/MAX PALM

/23
$650,000
- 3 Beds
- 2 Baths
- 2,103 Sq Ft
120 Candyce Dr, Osprey, FL 34229

This is your chance to own a true waterfront property in the highly desirable Osprey area and transform it into your dream coastal retreat. Situated on a canal with direct access to the Intracoastal Waterway, this home offers an unbeatable location for boating enthusiasts and anyone seeking the ultimate Florida lifestyle. The property itself needs some love, but that’s exactly what makes it such

Michelle Ward COMPASS FLORIDA LLC

120 Candyce Dr, Osprey, FL 34229
/2
$745,000 Sold Jan 16, 2026

640 Crane Prairie Way, Osprey, FL 34229
- 3 Beds
- 2.5 Baths
- 2,534 Sq Ft
- Built 2005
Last Sold Summary
- 3% Below List Price
- $294/SF
- 23 Days On Market
Current Estimated Value $749,544

Last Listing Agent Jay Mitchell COLDWELL BANKER REALTY

640 Crane Prairie Way, Osprey, FL 34229

/57
Est $647,646 Not Listed For Sale

6100 Jessie Harbor Dr Unit 201, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,630 Sq Ft
- Built 2005
6100 Jessie Harbor Dr Unit 201, Osprey, FL 34229

Last Sold Summary
- 11% Below List Price
- $276/SF
- 222 Days On Market
Last Sold Price $725,000

Last Listing Agent Bernadette Caswell Michael Saunders

/15
$41,000
570 Blackburn Point Rd Unit 42, Osprey, FL 34229

Welcome to OSPREY HARBOR VILLAGE. This boat rackominium was built as a category 3 hurricane-rated building. Store your boat out of the sun and protected from the harsh Florida weather. This 3rd-level rack measures 28'L x 12'W x 8.5'H and can accommodate a boat with dimensions of 28'L x 11'W x ~6.5'H (measure height from the keel to the highest fixed point on the boat). This rackominium features

Joe Cleary RE/MAX ALLIANCE GROUP

570 Blackburn Point Rd Unit 42, Osprey, FL 34229
/2
$1,100,000 Sold Apr 23, 2025

229 Lookout Point Dr, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,388 Sq Ft
- Built 2013
Last Sold Summary
- $461/SF
- 1 Day On Market
Current Estimated Value $1,088,985

Last Listing Agent Valerie Dall'acqua PREMIER SOTHEBY'S INTERNATIONAL REALTY

229 Lookout Point Dr, Osprey, FL 34229

/2
Est $692,394 Not Listed For Sale

401 N Point Rd Unit 401, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,594 Sq Ft
- Built 2003
401 N Point Rd Unit 401, Osprey, FL 34229

Last Sold Summary
- 7% Below List Price
- $287/SF
- 17 Days On Market
Last Sold Price $745,000

Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

/36
$429,500
- 3 Beds
- 2 Baths
- 1,300 Sq Ft
352 Glenwood Ave, Osprey, FL 34229

Beautifully Maintained 3-Bedroom Home with No HOA or Deed Restrictions Welcome to this immaculate 3-bedroom, 2-bath home, newly built in 2021 and perfectly located just minutes from top-rated beaches, shopping, dining, and entertainment. This move-in-ready home offers a clean, modern design with a spacious open floor plan that’s ideal for both relaxing and entertaining. Enjoy cooking in the

Kano Keller WHITE SANDS REALTY GROUP FL

352 Glenwood Ave, Osprey, FL 34229
/2
$832,000 Sold Apr 14, 2025

14041 Bellagio Way Unit 313, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 1,988 Sq Ft
- Built 2006
Last Sold Summary
- 10% Below List Price
- $419/SF
- 178 Days On Market
Current Estimated Value $738,741

Last Listing Agent Megan George PREMIER SOTHEBYS INTL REALTY

14041 Bellagio Way Unit 313, Osprey, FL 34229

/96
Est $1,011,656 Not Listed For Sale

385 N Point Rd Unit 501, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,594 Sq Ft
- Built 2000
385 N Point Rd Unit 501, Osprey, FL 34229

Last Sold Summary
- 16% Below List Price
- $463/SF
- 0 Days On Market
Last Sold Price $1,200,000

Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

/4
$36,000
570 Blackburn Point Rd Unit Siesta 26, Osprey, FL 34229

This slip will house a boat with the maximum dimensions of 35.5' length, 10' width and 6' height 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

David Babel BRIGHT REALTY

570 Blackburn Point Rd Unit Siesta 26, Osprey, FL 34229
/2
$215,000 Sold Nov 12, 2025

158 Edgewood Dr, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,480 Sq Ft
- Built 2014
Last Sold Summary
- 9% Below List Price
- $145/SF
- 12 Days On Market
Last Listing Agent Renee Marquiss NEXTHOME IN THE SUN

158 Edgewood Dr, Osprey, FL 34229

/73
Est $399,832 Not Listed For Sale

291 Hidden Bay Dr Unit 201, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,599 Sq Ft
- Built 2000
291 Hidden Bay Dr Unit 201, Osprey, FL 34229

Last Sold Summary
- 18% Below List Price
- $303/SF
- 7 Days On Market
Last Sold Price $485,000

Last Listing Agent Terri Lindsay LINDSAY LEASING LLC

/23
$4,750,000 Pending
- 4 Beds
- 4 Baths
- 3,462 Sq Ft
854 N Casey Key Rd, Osprey, FL 34229

On the quiet and coveted stretch of North Casey Key, where century-old oaks meet the shoreline, and the land unfolds uninterrupted from Gulf to bay, this extraordinary 1.5-acre estate offers a rare opportunity to steward one of the island’s most incredible homesites. With 180 feet of private Gulf frontage and exceptional depth across to the intercoastal, the property is defined by its scale,

Charles Ruck POTTER TRINITY

854 N Casey Key Rd, Osprey, FL 34229
/2
$710,000 Sold May 09, 2025

710 Shadow Bay Way, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,533 Sq Ft
- Built 2002
Last Sold Summary
- 11% Below List Price
- $280/SF
- 117 Days On Market
Current Estimated Value $727,661

Last Listing Agent Veronica Manes MICHAEL SAUNDERS & COMPANY

710 Shadow Bay Way, Osprey, FL 34229

/33
Est $367,535 Not Listed For Sale

293 Hidden Bay Dr Unit 201, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,599 Sq Ft
- Built 2000
293 Hidden Bay Dr Unit 201, Osprey, FL 34229

Last Sold Summary
- 21% Below List Price
- $292/SF
- 18 Days On Market
Last Sold Price $467,500

Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

/84
$170,000 Pending
- 2 Beds
- 2 Baths
- 1,151 Sq Ft
316 Tropic Dr, Osprey, FL 34229

Welcome to easy Florida living in The Arbors of Osprey! This charming 2-bedroom, 2-bath mobile home offers generous space, some updates, and a vibrant 55+ lifestyle in one of the area’s most convenient locations. Step inside to find a formal living room accented with built-in features, plus a dedicated dining room perfect for entertaining or everyday meals. The home boasts spacious room sizes

Karen Geiger COLDWELL BANKER SARASOTA CENT.

316 Tropic Dr, Osprey, FL 34229
/2
$1,500,000 Sold Dec 12, 2025

325 Osprey Point Dr, Osprey, FL 34229
- 3 Beds
- 4.5 Baths
- 3,905 Sq Ft
- Built 1986
Last Sold Summary
- 11% Below List Price
- $384/SF
- 12 Days On Market
Current Estimated Value $1,510,455

Last Listing Agent Mark Lyda GENEROUS PROPERTY

325 Osprey Point Dr, Osprey, FL 34229

/40
Est $1,768,073 Not Listed For Sale

1787 S Creek Dr, Osprey, FL 34229
- 3 Beds
- 2.5 Baths
- 2,567 Sq Ft
- Built 1990
1787 S Creek Dr, Osprey, FL 34229

Last Sold Summary
- 4% Above List Price
- $662/SF
- 42 Days On Market
Last Sold Price $1,700,000

Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

/77
$388,000 Pending
- 2 Beds
- 2 Baths
- 1,574 Sq Ft
124 Revolution Way, Osprey, FL 34229

Under contract-accepting backup offers. The only available home in the community with a 2 Car Garage! Welcome to Bay Street Village, a charming, beach-close, gated community in sought-after Osprey. This rarely available First-Floor residence features an oversized two-car garage with exceptional space for vehicles, bikes, kayaks, and all your Florida adventure gear. Ideally situated on a quiet

James Briley COLDWELL BANKER REALTY

124 Revolution Way, Osprey, FL 34229
/2
$285,000 Sold Mar 24, 2026

2043 Cordes St, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 1,186 Sq Ft
- Built 1957
Last Sold Summary
- 5% Below List Price
- $240/SF
- 44 Days On Market
Current Estimated Value $286,885

Last Listing Agent Travis Matthews PREFERRED SHORE LLC

2043 Cordes St, Osprey, FL 34229

/68
Est $982,797 Not Listed For Sale

501 Velasquez Dr, Osprey, FL 34229
- 3 Beds
- 4 Baths
- 3,028 Sq Ft
- Built 1975
501 Velasquez Dr, Osprey, FL 34229

Last Sold Summary
- 2% Below List Price
- $330/SF
- 56 Days On Market
Last Sold Price $1,000,000

Last Listing Agent Randy Owens COLDWELL BANKER REALTY

/45
$515,350
- 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
$113,000 Sold Feb 17, 2026

26 Siesta Cir W, Osprey, FL 34229
- 2 Beds
- 1 Bath
- 600 Sq Ft
- Built 1968
Last Sold Summary
- 13% Below List Price
- $188/SF
- 55 Days On Market
Last Listing Agent Gary Hoskins COLDWELL BANKER REALTY

26 Siesta Cir W, Osprey, FL 34229

/40
Est $511,925 Not Listed For Sale

510 Meadow Sweet Cir, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 1,788 Sq Ft
- Built 2001
510 Meadow Sweet Cir, Osprey, FL 34229

Last Sold Summary
- 12% Below List Price
- $324/SF
- 19 Days On Market
Last Sold Price $580,000

Last Listing Agent Mary Jo Violett Michael Saunders

/73
$2,495,000
- 5 Beds
- 5.5 Baths
- 4,261 Sq Ft
479 S Creek Dr, Osprey, FL 34229

Positioned on South Creek just off the Intracoastal Waterway with beautiful views and over 130 FEET of WATERFRONT, this 5-bedroom, 5.5-bath coastal estate offers over 4,261 square feet of refined waterfront living anchored by a truly spectacular backyard oasis. The heated saltwater PebbleTec pool, featuring an impressive 10-FOOT DEPTH, is paired with a separate spa and framed by elegant

Michelle Hupp KELLER WILLIAMS ISLAND LIFE REAL ESTATE

479 S Creek Dr, Osprey, FL 34229

Showing Results 201 - 240, Page 6 of 18

Florida Sarasota County Osprey

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