Osprey, FL Homes

/41
$699,000
- 3 Beds
- 2 Baths
- 1,736 Sq Ft
14041 Bellagio Way Unit 415, Osprey, FL 34229

A boater's dream. Enjoy waterfront living in this luxury penthouse unit with breathtaking views of the Intracoastal Waterway located in the premier gated community of The Villas at Bellagio. Upon entering the home, you are greeted by the inviting foyer leading down the art gallery-like hallway to the open family room and kitchen area. This three-bedroom, two-bathroom unit has many wonderful

Stephen Hachey FLAT FEE MLS REALTY

14041 Bellagio Way Unit 415, Osprey, FL 34229
/2
$85,000 Sold Jul 01, 2025

570 Blackburn Point Rd Unit 7, Osprey, FL 34229
- Built 2006
Last Sold Summary
- 11% Below List Price
- 336 Days On Market
Current Estimated Value $83,200

Last Listing Agent Troy Gager BRIGHT REALTY

570 Blackburn Point Rd Unit 7, Osprey, FL 34229

/20
Est $632,260 Not Listed For Sale

1323 Thornapple Dr, Osprey, FL 34229
- 4 Beds
- 3 Baths
- 2,336 Sq Ft
- Built 2003
1323 Thornapple Dr, Osprey, FL 34229

Last Sold Summary
- 6% Below List Price
- $287/SF
- 163 Days On Market
Last Sold Price $670,000

Last Listing Agent Stacey Fout LPT REALTY LLC (DB)

/70
$699,000
- 2 Beds
- 2.5 Baths
- 1,950 Sq Ft
260 Hidden Bay Dr Unit B-304, Osprey, FL 34229

The Boca Residence: Spacious Living & Resort StyleDiscover a condominium that offers the true scale and functionality of a private home. The Boca floor plan features a thoughtfully designed two-bedroom plus den, two-and-a-half-bathroom layout, perfect for those who want the ease of condo living without sacrificing space. Whether you are looking for a full-time residence or a spacious seasonal

Janice Martin ENGEL & VOELKERS VENICE DOWNTOWN

260 Hidden Bay Dr Unit B-304, Osprey, FL 34229
/2
$505,000 Sold Jul 08, 2025

622 Pine Ranch Rd E, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 2,302 Sq Ft
- Built 1995
Last Sold Summary
- 26% Below List Price
- $219/SF
- 50 Days On Market
Current Estimated Value $520,912

Last Listing Agent Terri Persing PARADISE EXCLUSIVE INC

622 Pine Ranch Rd E, Osprey, FL 34229

/39
Est $525,006 Not Listed For Sale

2271 Jessie Harbor Dr Unit 2203, Osprey, FL 34229
- 3 Beds
- 2.5 Baths
- 2,006 Sq Ft
- Built 2006
2271 Jessie Harbor Dr Unit 2203, Osprey, FL 34229

Last Sold Summary
- 8% Below List Price
- $284/SF
- 52 Days On Market
Last Sold Price $570,000

Last Listing Agent Michelle Crabtree PREMIER SOTHEBY'S INTERNATIONAL REALTY

/63
$785,000
- 3 Beds
- 3 Baths
- 2,594 Sq Ft
393 N Point Rd Unit 401, Osprey, FL 34229

This beautifully updated 3 bedroom, 3 bath residence with a den offers exceptional space, style, and privacy in Meridian at The Oaks Preserve. The home features a redesigned kitchen with new appliances and granite countertops, a newer A/C system, and rich wood flooring throughout. As an end unit, it enjoys abundant natural light, and the expansive screened balcony—with electric hurricane

Steve Abbe COLDWELL BANKER REALTY

393 N Point Rd Unit 401, Osprey, FL 34229
/2
$385,000 Sold Apr 16, 2025

329 Bay Vista Ave, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,346 Sq Ft
- Built 1963
Last Sold Summary
- 14% Below List Price
- $286/SF
- 244 Days On Market
Current Estimated Value $395,122

Last Listing Agent Colette Jay HORIZON REALTY INTERNATIONAL

329 Bay Vista Ave, Osprey, FL 34229

/2
Est $572,576 Not Listed For Sale

511 Latitude Ln, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 2,165 Sq Ft
- Built 2004
511 Latitude Ln, Osprey, FL 34229

Last Sold Summary
- 3% Above List Price
- $257/SF
- 133 Days On Market
Last Sold Price $557,000

Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

/82
$1,250,000
- 5 Beds
- 3.5 Baths
- 3,481 Sq Ft
296 Pine Ranch Trail, Osprey, FL 34229

**THIS PROPERTY QUALIFIES FOR A LENDER INCENTIVE (up to $8,000) IF USING PREFERRED LENDER. INQUIRE FOR MORE DETAILS.** & SELLER IS OFFERING A $25,000.00 CREDIT toward rate buy down/closing cost with acceptable contract. Welcome to your private retreat nestled in one of Osprey’s most desirable enclaves. This beautifully situated home rests on a lush greenbelt lot that borders the fairways of a

Deborah Frederick ASHTON LAKES REALTY INC

296 Pine Ranch Trail, Osprey, FL 34229
/2
$640,000 Sold Sep 25, 2025

6 Bay Acres Ave, Osprey, FL 34229
- 1,887 Sq Ft
- Built 1997
Last Sold Summary
- 7% Below List Price
- $339/SF
- 48 Days On Market
Current Estimated Value $634,083

Last Listing Agent Bogdan Osipov OSIPOV GROUP REAL ESTATE

6 Bay Acres Ave, Osprey, FL 34229

/46
Est $1,049,372 Not Listed For Sale

423 S Creek Dr, Osprey, FL 34229
- 4 Beds
- 3.5 Baths
- 3,107 Sq Ft
- Built 1992
423 S Creek Dr, Osprey, FL 34229

Last Sold Summary
- 7% Above List Price
- $315/SF
- 1 Day On Market
Last Sold Price $980,000

Last Listing Agent Claude Pierre CP REALTY INTERNATIONAL

/71
$539,000 Pending
- 4 Beds
- 2 Baths
- 2,186 Sq Ft
1036 Oak Meadow Ln Unit 3A, Osprey, FL 34229

Welcome to this attractive St. Charles floor plan found in the desirable Woodlands at Rivendell community! This charming home sits on a large corner lot directly across from the heated community pool and is within easy reach of the highly ranked Pine View School for the Gifted (Grades:2-12). Built in 2001, this well-maintained home features four bedrooms, or three bedrooms plus den with closet,

Helena Nordstrom PREMIER SOTHEBY'S INTERNATIONAL REALTY

1036 Oak Meadow Ln Unit 3A, Osprey, FL 34229
/2
$315,000 Sold Apr 24, 2025

214 Patterson Ave, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 1,092 Sq Ft
- Built 2004
Last Sold Summary
- 17% Below List Price
- $288/SF
- 147 Days On Market
Current Estimated Value $308,674

Last Listing Agent Lisa Bouck, PA RE/MAX ALLIANCE GROUP

214 Patterson Ave, Osprey, FL 34229

/54
Est $804,179 Not Listed For Sale

216 Windward Dr, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,575 Sq Ft
- Built 1982
216 Windward Dr, Osprey, FL 34229

Last Sold Summary
- 3% Above List Price
- $304/SF
- 62 Days On Market
Last Sold Price $782,500

Last Listing Agent Sharon Lewis GOLF & BAY PROPERTIES LLC

/96
$2,500,000
- 4 Beds
- 3.5 Baths
- 3,953 Sq Ft
49 Osprey Point Dr, Osprey, FL 34229

Nestled in the prestigious gated enclave of The Oaks Bayside in Sarasota, this Sedona-inspired retreat was recently updated from wall to wall creating a like brand new home. The estate seamlessly blends modern luxury, comfort, and serenity. With almost 4,000 SQF and boasting 4 generously sized bedrooms and 3 1/2 baths, this residence has been thoughtfully renovated with the finest finishes,

Jonathan Abrams MICHAEL SAUNDERS & COMPANY

49 Osprey Point Dr, Osprey, FL 34229
/2
$489,000 Sold Jul 03, 2025

328 Woods Point Rd, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,862 Sq Ft
- Built 1990
Last Sold Summary
- $263/SF
Current Estimated Value $484,442

Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

328 Woods Point Rd, Osprey, FL 34229

/82
Est $897,878 Not Listed For Sale

682 Clear Creek Dr, Osprey, FL 34229
- 5 Beds
- 3 Baths
- 3,900 Sq Ft
- Built 2002
682 Clear Creek Dr, Osprey, FL 34229

Last Sold Summary
- 5% Below List Price
- $244/SF
- 39 Days On Market
Last Sold Price $950,000

Last Listing Agent Carlo Costantini DAVE JONES REALTY, LLC

/93
$649,500
- 3 Beds
- 2 Baths
- 2,505 Sq Ft
186 Windward Dr, Osprey, FL 34229

Price was reduced over $100,000!!! Went pending immediately and then the buyers couldn't secure financing. It is now BACK ON MARKET as of 3/19 and NO INSPECTIONS HAVE BEEN DONE! Located in the desirable Southbay Yacht & Racquet Club, this 3-bedroom, 2-bath residence offers a split bedroom layout, unique community amenities, NEW ROOF in 2022, and plenty of room for a private pool. As you enter the

Brittany Coleman KELLER WILLIAMS ON THE WATER S

186 Windward Dr, Osprey, FL 34229
/2
$425,000 Sold Oct 29, 2025

264 Woods Point Rd, Osprey, FL 34229
- 2 Beds
- 3 Baths
- 2,837 Sq Ft
- Built 1992
Last Sold Summary
- 35% Below List Price
- $150/SF
- 368 Days On Market
Current Estimated Value $437,146

Last Listing Agent Mark Midyett KELLER WILLIAMS ON THE WATER S

264 Woods Point Rd, Osprey, FL 34229

/45
Est $626,560 Not Listed For Sale

752 Sarabay Rd Unit 2, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,574 Sq Ft
- Built 1981
752 Sarabay Rd Unit 2, Osprey, FL 34229

Last Sold Summary
- 10% Below List Price
- $442/SF
- 1 Day On Market
Last Sold Price $695,000

Last Listing Agent Beth Dilley ASCENDIA REAL ESTATE

/99
$1,095,000
- 4 Beds
- 3 Baths
- 2,770 Sq Ft
403 Longbow Trail, Osprey, FL 34229

Welcome to this beautifully maintained 4 bed, 3 bath property nestled on a 2-acre lot in one of Osprey's most desirable communities Pine Ranch. Located 15 minutes from Siesta Key and Nokomis Beach and is within a short distance from the nationally top-rated Pine View School, #1 High School in Florida and the natural beauty of the Legacy Trail. This charming home offers a perfect blend of comfort,

Edward Bieker DALTON WADE INC

403 Longbow Trail, Osprey, FL 34229
/2
$665,000 Sold May 23, 2025

123 Tina Island Dr, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 1,922 Sq Ft
- Built 1964
Last Sold Summary
- 11% Below List Price
- $346/SF
- 125 Days On Market
Current Estimated Value $683,713

Last Listing Agent Glenn Davis COLDWELL BANKER SARASOTA CENT.

123 Tina Island Dr, Osprey, FL 34229

/2
Est $499,850 Not Listed For Sale

555 Meadow Sweet Cir, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,680 Sq Ft
- Built 1997
555 Meadow Sweet Cir, Osprey, FL 34229

Last Sold Summary
- 4% Below List Price
- $310/SF
- 14 Days On Market
Last Sold Price $520,000

Last Listing Agent Jack Keller JACK KELLER INC

/2
$592,249 New Construction
- 3 Beds
- 2 Baths
- 1,356 Sq Ft
791 S Tamiami Trail Unit 201, Osprey, FL 34229

Under Construction. UNDER CONSTRUCTION -STARTING FROM THE MID $500,000'S. NO FLOOD INSURANCE REQUIRED. NOW TAKING RESERVATIONS ON THIS NEW VENICE ISLAND CONDOMINIUM COMMUNITY KNOW AS ISOLA CASA! 36 CONDOMINIUM UNITS WITHIN 4 SEPARATE BUILDINGS THAT INCLUDE ELEVATORS. THIS UNIT BOASTS 3 BEDROOMS, 2 BATHROOMS WITH A SCREENED LANAI AND HAS A 1-CAR DETACHED GARAGE. (2 BEDROOM AND 2 BATH UNITS ALSO

Laurie Eshleman PRO GROUP REALTY & PROP MGT

791 S Tamiami Trail Unit 201, Osprey, FL 34229
/2
$165,000 Sold Apr 28, 2025

235 Woodland Dr Unit 235, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,223 Sq Ft
- Built 1980
Last Sold Summary
- 17% Below List Price
- $135/SF
- 53 Days On Market
Current Estimated Value $167,225

Last Listing Agent Priscilla Adams COMPASS FLORIDA LLC

235 Woodland Dr Unit 235, Osprey, FL 34229

/87
Est $394,936 Not Listed For Sale

223 Hidden Bay Dr Unit 303, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 1,515 Sq Ft
- Built 1997
223 Hidden Bay Dr Unit 303, Osprey, FL 34229

Last Sold Summary
- 12% Below List Price
- $297/SF
- 131 Days On Market
Last Sold Price $450,000

Last Listing Agent Jessica Bow RE/MAX PALM

/51
$415,000
- 2 Beds
- 2 Baths
- 2,148 Sq Ft
32 Bay Ave, Osprey, FL 34229

Located in the highly sought-after Bay Acres community, this home offers modern upgrades, spacious living, and access to one of the area’s most desirable boating lifestyles. Recent updates include a metal roof, 2018 HVAC system with all-new ductwork, 2022 whole-house re-plumb including sewer lines, underground electric and 200-amp electrical panel, new septic system, water heater, and stainless

Jennifer Pereira LOKATION

32 Bay Ave, Osprey, FL 34229
/2
$475,000 Sold Mar 26, 2026

34 Washington Ave, Osprey, FL 34229
- Land
- 1.07 Acres
- $443,925 per Acre
Last Sold Summary
- 13% Below List Price
- 56 Days On Market
Current Estimated Value $540,959

Last Listing Agent Al Grabo ARCO REALTY GROUP

34 Washington Ave, Osprey, FL 34229

/2
Est $852,645 Not Listed For Sale

1251 Windward Dr, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 2,015 Sq Ft
- Built 1986
1251 Windward Dr, Osprey, FL 34229

Last Sold Summary
- 3% Below List Price
- $434/SF
- 93 Days On Market
Last Sold Price $875,000

Last Listing Agent Lauren Doyle DALTON WADE INC

/8
$15,995
- 1 Bed
- 1 Bath
- 370 Sq Ft
124 Happy Haven Dr Unit 5, Osprey, FL 34229

Happy Haven, a professionally managed, well-maintained manufactured home community, currently has a 370 sq. ft. home with 1 bedrooms and 1 bathrooms for sale. Take advantage of this offer now and live in one of the state's most attractive areas. Call and schedule a viewing of this home and ask about our current promotions!

Tori Coil Happy Haven

124 Happy Haven Dr Unit 5, Osprey, FL 34229
/2
$200,000 Sold Nov 24, 2025

226 Woodland Dr, Osprey, FL 34229
- 1 Bed
- 1.5 Baths
- 865 Sq Ft
- Built 1980
Last Sold Summary
- $231/SF
Current Estimated Value $188,123

Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

226 Woodland Dr, Osprey, FL 34229

/2
Est $589,405 Not Listed For Sale

817 Placid Lake Dr, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 2,102 Sq Ft
- Built 2002
817 Placid Lake Dr, Osprey, FL 34229

Last Sold Summary
- 6% Below List Price
- $297/SF
- 53 Days On Market
Last Sold Price $625,000

Last Listing Agent Leonard Giarrano RE/MAX

/41
$419,000
- 3 Beds
- 2 Baths
- 1,760 Sq Ft
524 Sarabay Rd, Osprey, FL 34229

Location, Location. In the Heart of Osprey, centrally located in the highly sought-after well-established Bay Acres Community. Lowest priced home west of the Taril. These 3 bedrooms 2 bath ranch home is West of 41 within 10-minute commutes to downtown Sarasota and downtown Venice, Florida. Across the street from Walmart with bus transportation to Sarasota and Venice. You can walk to Walmart, the

Ibetta Giannone SUN N SAND REAL ESTATE LLC

524 Sarabay Rd, Osprey, FL 34229
/2
$285,000 Sold May 30, 2025

7102 Jessie Harbor Dr, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,255 Sq Ft
- Built 1985
Last Sold Summary
- 24% Below List Price
- $227/SF
- 112 Days On Market
Current Estimated Value $265,019

Last Listing Agent Chris Rankin RE/MAX PALM REALTY

7102 Jessie Harbor Dr, Osprey, FL 34229

/61
Est $128,967 Not Listed For Sale

750 Pine Run Dr, Osprey, FL 34229
- 1 Bed
- 1 Bath
- 586 Sq Ft
- Built 1973
750 Pine Run Dr, Osprey, FL 34229

Last Sold Summary
- 22% Below List Price
- $282/SF
- 12 Days On Market
Last Sold Price $165,000

Last Listing Agent Priscilla Adams COMPASS FLORIDA LLC

/70
$899,995 Pending
- 3 Beds
- 4 Baths
- 3,561 Sq Ft
616 Crane Prairie Way, Osprey, FL 34229

Under contract-accepting backup offers. Located in Willowbend, this expansive residence offers a rare blend of space, privacy, and long-term potential, set against tranquil water and preserve views with Oscar Scherer State Park as a stunning natural backdrop. Offering over 3,500 square feet of living space, the home provides exceptional flexibility for buyers looking to personalize a

Matthew Greenland KELLER WILLIAMS ISLAND LIFE REAL ESTATE

616 Crane Prairie Way, Osprey, FL 34229
/2
$295,000 Sold Mar 17, 2026

100 Navigation Cir, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,135 Sq Ft
- Built 2018
Last Sold Summary
- 3% Below List Price
- $260/SF
- 44 Days On Market
Current Estimated Value $300,676

Last Listing Agent Zita Bowers MICHAEL SAUNDERS & COMPANY

100 Navigation Cir, Osprey, FL 34229

/63
Est $1,054,636 Not Listed For Sale

1762 Island Way, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,462 Sq Ft
- Built 1988
1762 Island Way, Osprey, FL 34229

Last Sold Summary
- 4% Below List Price
- $447/SF
- 11 Days On Market
Last Sold Price $1,100,000

Last Listing Agent Roberta Tengerdy, PA PREMIER SOTHEBY'S INTERNATIONAL REALTY

/83
$2,400,000 Pending
- 4 Beds
- 5.5 Baths
- 4,346 Sq Ft
530 N Mac Ewen Dr, Osprey, FL 34229

Under contract-accepting backup offers. Located in the prestigious gated community of The Oaks Golf & Country Club in Osprey (Sarasota area), this elegant single-story residence at 530 N Mac Ewen Drive offers resort-style living with championship golf just steps away. Spanning 4,346 square feet under air and 5,837 square feet under roof on an oversized lot, the home features 4 bedrooms, 5 full

Niall Phelan LPT REALTY, LLC

530 N Mac Ewen Dr, Osprey, FL 34229

Showing Results 561 - 600, Page 15 of 18

Florida Sarasota County Osprey

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

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

Osprey, FL Homes

Real Estate & Homes