Osprey, FL Homes

/95
$5,495,000
- 4 Beds
- 5.5 Baths
- 6,308 Sq Ft
730 Sarabay Rd, Osprey, FL 34229

Premier Intracoastal Estate in Osprey4 Bedrooms | 6 Bathrooms | 6,308 Sq. Ft. | 2 Waterfront AcresA rare opportunity to own two acres of private waterfront property in Sarasota, 730 Sarabay is aconvergence of residential luxury and unparalleled waterfront living. The two-story home sits atthe end of a long drive behind a gated entrance and tranquil pond. With approximately 100

Debbie Baraona ROBERT SLACK LLC

730 Sarabay Rd, Osprey, FL 34229
/2
$325,000 Sold Jan 17, 2025

51 MacEwen Dr Unit 20, Osprey, FL 34229
- 1 Bed
- 1 Bath
- 623 Sq Ft
- Built 1990
Last Sold Summary
- $522/SF
- 0 Days On Market
Current Estimated Value $285,560

Last Listing Agent Mark Lyda GENEROUS PROPERTY

51 MacEwen Dr Unit 20, Osprey, FL 34229

/96
Est $1,061,622 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,594 Sq Ft
385 N Point Rd Unit 501, Osprey, FL 34229

385 N Point Rd Unit 501, Osprey, FL 34229

/8
$750,000
- Land
- 0.47 Acre
- $1,595,745 per Acre
147 Osprey Point Dr, Osprey, FL 34229

Your dream homesite awaits! This lot is located within the Oaks Bayside, one of Southwest Florida‘s most exclusive private, gated communities. This amazing property is near the community dock and fountain and is surrounded by some of the most grand and luxurious homes in the entire gulf coast region. The Oaks Club boasts 2 Championship Golf Courses, 12 Har-Tru Tennis Courts (4 lighted), State Of

Mick Jordan BRIGHT REALTY

147 Osprey Point Dr, Osprey, FL 34229
/2
$395,000 Sold Jun 16, 2025

109 Burney Rd, Osprey, FL 34229
- 2 Beds
- 1.5 Baths
- 714 Sq Ft
- Built 1959
Last Sold Summary
- 8% Below List Price
- $553/SF
- 50 Days On Market
Current Estimated Value $381,621

Last Listing Agent Lori Madden MANGROVE REALTY ASSOCIATES

109 Burney Rd, Osprey, FL 34229

/73
Est $429,237 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,599 Sq Ft
291 Hidden Bay Dr Unit 201, Osprey, FL 34229

291 Hidden Bay Dr Unit 201, Osprey, FL 34229

/19
$129,500
- 2 Beds
- 1 Bath
- 600 Sq Ft
26 Siesta Cir W, Osprey, FL 34229

Just Move In ... Affordable Fully furnished 2-bedroom home with central air is located in an active 55 and over community Located in the heart of Osprey with nearby shopping and dining and easy access to nearby Siesta Key Beach, Casey Key and Nokomis Beach along with The Legacy Bike trail and Oscer Scherer State Park. The Arbors Mobile Home Park with Low Hoa Fees offers a heated community pool

Gary Hoskins COLDWELL BANKER REALTY

26 Siesta Cir W, Osprey, FL 34229
/2
$700,000 Sold Oct 08, 2025

826 Oak Briar Ln, Osprey, FL 34229
- 4 Beds
- 3 Baths
- 2,589 Sq Ft
- Built 2003
Last Sold Summary
- 10% Below List Price
- $270/SF
- 160 Days On Market
Last Listing Agent Peter LaSalle PREFERRED SHORE LLC

826 Oak Briar Ln, Osprey, FL 34229

/33
Est $406,304 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,599 Sq Ft
293 Hidden Bay Dr Unit 201, Osprey, FL 34229

293 Hidden Bay Dr Unit 201, Osprey, FL 34229

/73
$1,800,000 Pending
- 3 Beds
- 3 Baths
- 2,778 Sq Ft
409 N Point Rd Unit 1003, Osprey, FL 34229

Beautifully updated and meticulously maintained 3 bedroom, 3 bath penthouse in Meridian at The Oaks Preserve. Offering a two car garage, 8’ solid core doors & roll down shutters on the screened balcony. The views are gorgeous. The Meridian has a residents-only pool, spa and work out room. Located in the heart of south Sarasota, The Oaks offers 2 championship golf courses, a world-class tennis

Steve Abbe COLDWELL BANKER REALTY

409 N Point Rd Unit 1003, Osprey, FL 34229
/2
$245,000 Sold Apr 21, 2025

225 Woodland Dr, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,316 Sq Ft
- Built 1980
Last Sold Summary
- 18% Below List Price
- $186/SF
- 103 Days On Market
Current Estimated Value $239,154

Last Listing Agent Priscilla Adams COMPASS FLORIDA LLC

225 Woodland Dr, Osprey, FL 34229

/40
Est $1,544,440 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,567 Sq Ft
1787 S Creek Dr, Osprey, FL 34229

1787 S Creek Dr, Osprey, FL 34229

/11
$699,000
- 3 Beds
- 2 Baths
- 2,058 Sq Ft
110 Pine Ave, Osprey, FL 34229

Heart of Osprey, this remodeled 3-bedroom, 2-bathroom pool home with huge yard, bring your RV and all your toys. Lots of room for storage. Enjoy sunsets, steps to fishing pier, kayak launch, Spanish Pointe, Oscar Scherer State Park, and Pine View School. No restrictions. Move-in ready enjoying the Florida lifestyle! For outdoor enthusiasts, this location is unbeatable. Launch your kayak or

Marisa Marino BRIGHT REALTY

110 Pine Ave, Osprey, FL 34229
/2
$832,750 Sold Apr 10, 2025

280 Hidden Bay Dr Unit 303, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 1,937 Sq Ft
- Built 2025
Last Sold Summary
- $430/SF
- 27 Days On Market
Current Estimated Value $815,264

Last Listing Agent Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

280 Hidden Bay Dr Unit 303, Osprey, FL 34229

/68
Est $967,837 Not Listed For Sale
- 3 Beds
- 4 Baths
- 3,028 Sq Ft
501 Velasquez Dr, Osprey, FL 34229

501 Velasquez Dr, Osprey, FL 34229

/47
$650,000
- 4 Beds
- 3 Baths
- 2,557 Sq Ft
104 Park Trace Blvd, Osprey, FL 34229

Welcome to this elegant and spacious luxury pool home offering over 2,500 square feet of refined living in one of the most desirable communities along the Gulf Coast. With a freshly painted exterior, stunning hardwood floors throughout, and an exceptional layout designed for both comfort and style, this residence is move-in ready and perfectly suited for modern living. Boasting four bedrooms,

Lisa Morreale PREMIER SOTHEBY'S INTERNATIONAL REALTY

104 Park Trace Blvd, Osprey, FL 34229
/2
$2,327,000 Sold Jun 18, 2025

654 Trenton Way, Osprey, FL 34229
- 4 Beds
- 3.5 Baths
- 3,582 Sq Ft
- Built 1990
Last Sold Summary
- 5% Below List Price
- $650/SF
- 86 Days On Market
Current Estimated Value $2,218,451

Last Listing Agent Mark Lyda GENEROUS PROPERTY

654 Trenton Way, Osprey, FL 34229

/40
Est $515,439 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,788 Sq Ft
510 Meadow Sweet Cir, Osprey, FL 34229

510 Meadow Sweet Cir, Osprey, FL 34229

/100
$2,350,000
- 3 Beds
- 2.5 Baths
- 3,738 Sq Ft
393 N Point Rd Unit 1002, Osprey, FL 34229

Experience Unmatched Luxury in this Meridian Penthouse! Welcome to the epitome of luxury living at Meridian at The Oaks Preserve. This stunning 3 bedroom, 2.5 bath penthouse offers a private 2-car garage and is designed for the discerning buyer who values quality, elegance, and an unparalleled location. From sunrise to dramatic color-drenched sunsets over the Gulf, your days will be filled with

Steve Abbe COLDWELL BANKER REALTY

393 N Point Rd Unit 1002, Osprey, FL 34229
/2
$2,925,000 Sold Sep 23, 2025

550 Dove Pointe, Osprey, FL 34229
- 4 Beds
- 5.5 Baths
- 7,842 Sq Ft
- Built 2006
Last Sold Summary
- 11% Below List Price
- $373/SF
- 63 Days On Market
Current Estimated Value $2,862,689

Last Listing Agent Jennifer Linehan MICHAEL SAUNDERS & COMPANY

550 Dove Pointe, Osprey, FL 34229

/52
Est $2,381,384 Not Listed For Sale
- 5 Beds
- 8 Baths
- 5,521 Sq Ft
134 Marys Chapel Ct, Osprey, FL 34229

134 Marys Chapel Ct, Osprey, FL 34229

/43
$674,000
- 4 Beds
- 2 Baths
- 2,145 Sq Ft
819 Shadow Bay Way, Osprey, FL 34229

A new 2025 roof. This stunning 2,145-square-foot pool home is in the premier community of Rivendell. Live so beautifully! This maintenance-free, tropically landscaped corner lot home has been eloquently updated and maintained. Featuring four bedrooms, formal dining room, two baths, two-car garage, fenced-in backyard, beautiful pool and lanai, and tile throughout most of the home. The inviting

Crystal Cosby, LLC PREMIER SOTHEBYS INTL REALTY

819 Shadow Bay Way, Osprey, FL 34229
/2
$2,100,000 Sold Mar 26, 2025

703 N MacEwen Dr, Osprey, FL 34229
- 4 Beds
- 3.5 Baths
- 4,641 Sq Ft
- Built 2007
Last Sold Summary
- 16% Below List Price
- $452/SF
- 95 Days On Market
Current Estimated Value $1,992,362

Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

703 N MacEwen Dr, Osprey, FL 34229

/41
Est $566,105 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 1,944 Sq Ft
506 Oak Bay Dr, Osprey, FL 34229

506 Oak Bay Dr, Osprey, FL 34229

/34
$699,900 Pending
- 4 Beds
- 2 Baths
- 2,434 Sq Ft
866 Oak Briar Ln, Osprey, FL 34229

Under contract-accepting backup offers. **NEW ROOF** Welcome to the highly desirable Park Trace Estates where residents enjoy low HOA fees! This beautiful pool home is move-in ready and features a split floor plan with three bedrooms and a 4th-bedroom/office giving you lots of space and flexibility. Many upgrades include pool resurfacing and tile, solar pool heater, pool pump, pool filter, AC,

Brian Leakeas COLDWELL BANKER REALTY

866 Oak Briar Ln, Osprey, FL 34229
/2
$1,500,000 Sold Jul 08, 2025

269 Pine Ranch Trail, Osprey, FL 34229
- 4 Beds
- 3.5 Baths
- 3,572 Sq Ft
- Built 1997
Last Sold Summary
- 16% Below List Price
- $420/SF
- 76 Days On Market
Current Estimated Value $1,462,447

Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

269 Pine Ranch Trail, Osprey, FL 34229

/79
Est $1,343,418 Not Listed For Sale
- 4 Beds
- 3 Baths
- 3,521 Sq Ft
1236 Yacht Harbor Dr, Osprey, FL 34229

1236 Yacht Harbor Dr, Osprey, FL 34229

/70
$2,299,900
- 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
$579,000 Sold Jan 16, 2025

1327 Thornapple Dr, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 2,165 Sq Ft
- Built 2003
Last Sold Summary
- 2% Below List Price
- $267/SF
- 16 Days On Market
Current Estimated Value $572,851

Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

1327 Thornapple Dr, Osprey, FL 34229

/45
Est $2,729,106 Not Listed For Sale
- 3 Beds
- 3 Baths
- 3,202 Sq Ft
349 Yacht Harbor Dr, Osprey, FL 34229

349 Yacht Harbor Dr, Osprey, FL 34229

/55
$429,900 Open House 1/04
- 2 Beds
- 2 Baths
- 1,574 Sq Ft
780 Sarabay Rd Unit 16, Osprey, FL 34229

Waterfront Villa - Private Courtyard & 2- Car Garage - Maintenance Free Living. Single story home-like living. Fish off the Pier or sit on the dock & enjoy the sunsets! Welcome to Heron Bay Club, an exclusive enclave of just 25 uniquely designed villas situated on 11 acres along the Little Sarasota Bay across from Casey Key. This spacious 2-bedroom, 2-bath villa features a versatile bonus

Mark Segreto RMS ELITE PROPERTIES

780 Sarabay Rd Unit 16, Osprey, FL 34229
/2
$3,050,000 Sold Aug 15, 2025

5 N Casey Key Rd, Osprey, FL 34229
- 4 Beds
- 3.5 Baths
- 2,380 Sq Ft
- Built 1969
Last Sold Summary
- 27% Below List Price
- $1,282/SF
- 278 Days On Market
Current Estimated Value $2,358,417

Last Listing Agent Kelley Ann Ayers AYERS AND ASSOCIATES REAL ESTATE

5 N Casey Key Rd, Osprey, FL 34229

/50
Est $363,257 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,184 Sq Ft
1821 Highland Rd, Osprey, FL 34229

1821 Highland Rd, Osprey, FL 34229

/38
$640,000 Pending
- 3 Beds
- 2 Baths
- 1,889 Sq Ft
178 Willow Bend Way, Osprey, FL 34229

Move-in ready and impeccably maintained, this stunning 3-bedroom, 2-bath pool home offers exceptional updates and an unbeatable location in the coveted Park Trace Estates. Nearly 2,000 sq. ft. of bright, open living space features a desirable split floor plan, abundant natural light, and a beautifully landscaped, private fenced backyard.Major upgrades deliver true peace of mind:• All-new

Kim Azar-Calka MICHAEL SAUNDERS & COMPANY

178 Willow Bend Way, Osprey, FL 34229
/2
$885,000 Sold Mar 31, 2025

236 Hidden Bay Dr Unit 504, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,100 Sq Ft
- Built 1997
Last Sold Summary
- 7% Below List Price
- $421/SF
- 115 Days On Market
Current Estimated Value $849,486

Last Listing Agent Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

236 Hidden Bay Dr Unit 504, Osprey, FL 34229

/86
Est $1,626,779 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 4,087 Sq Ft
435 E MacEwen Dr, Osprey, FL 34229

435 E MacEwen Dr, Osprey, FL 34229

/92
$900,000
- 3 Beds
- 2 Baths
- 2,216 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
$660,000 Sold Aug 26, 2025

463 Park Trace Blvd, Osprey, FL 34229
- 3 Beds
- 2.5 Baths
- 2,153 Sq Ft
- Built 2002
Last Sold Summary
- 12% Below List Price
- $307/SF
- 63 Days On Market
Current Estimated Value $662,300

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

463 Park Trace Blvd, Osprey, FL 34229

/2
Est $1,063,793 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,968 Sq Ft
1321 Southbay Dr, Osprey, FL 34229

1321 Southbay Dr, Osprey, FL 34229

/8
$700,000
- Land
- 0.24 Acre
- $2,916,667 per Acre
3813 Parrot Bay Ct, Osprey, FL 34229

Nestled within the exclusive community of Osprey, Florida, 3813 Parrot Bay Ct offers a rare opportunity to build your dream home on a premium lot in a tranquil cul-de-sac. This intimate enclave features just nine custom-built home sites, ensuring a private and close-knit neighborhood atmosphere. Best of all, buyers have the freedom to choose any builder to bring their vision to life. For boating

Dawn Merrill COMPASS FLORIDA LLC

3813 Parrot Bay Ct, Osprey, FL 34229

Showing Results 241 - 280, Page 7 of 18

Florida Sarasota County Osprey

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

Find More Real Estate & Homes for Sale by State

Top Cities with Homes For Sale

Top Counties with Homes For Sale

More Real Estate For Sale Near Me

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