Osprey, FL Homes

/73
$1,575,000
- 4 Beds
- 3 Baths
- 3,486 Sq Ft
20 Bayhead Ln, Osprey, FL 34229

A rare opportunity to own a significantly newer, custom-built residence inside the exclusive The Oaks Club Preserve, where most surrounding homes were built decades earlier. Completed in 2017 and set on a lakefront lot in a non-flood zone, this move-in-ready, hurricane-secure home offers a level of modern construction, privacy, and peace of mind seldom found in this exclusive community. In

Lielei Wahlmann EXP REALTY LLC

20 Bayhead Ln, Osprey, FL 34229
/15
$3,500 per month
- 3 Beds
- 2 Baths
- 1,648 Sq Ft
- House for Rent
2068 Preymore St, Osprey, FL 34229

Welcome home to this charming and beautifully maintained 3-bedroom, 2-bath residence located on a great community. Step inside to a spacious open floor plan featuring a generous great room, a dedicated dining area, and a large primary suite. Cathedral ceilings, pocket sliding doors, and fluid room transitions create an airy atmosphere perfect for easy living and entertaining. The bright, eat-in

Kenia Rivas PREFERRED SHORE LLC

2068 Preymore St, Osprey, FL 34229
/2
$1,405,000 Sold Jul 11, 2025

282 Shell Midden Ct, Osprey, FL 34229
- 3 Beds
- 4.5 Baths
- 3,699 Sq Ft
- Built 1992
Last Sold Summary
- 17% Below List Price
- $380/SF
- 128 Days On Market
Current Estimated Value $1,478,213

Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

282 Shell Midden Ct, Osprey, FL 34229

/22
Est $276,638 Not Listed For Sale

101 Navigation Cir Unit 101, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,135 Sq Ft
- Built 2014
101 Navigation Cir Unit 101, Osprey, FL 34229

Last Sold Summary
- 12% Below List Price
- $278/SF
- 80 Days On Market
Last Sold Price $315,000

Last Listing Agent Kimberly Stanford REALNET FLORIDA REAL ESTATE

/72
$2,250,000
- 4 Beds
- 3.5 Baths
- 4,012 Sq Ft
433 E MacEwen Dr, Osprey, FL 34229

An exceptionally well maintained 4,012sf residence with 4 bedrooms 3 full and a half baths situated on the interior Heron golf course on a 0.61 acre lot in the private Oaks Club community. It has golf course and water views and 24 hr gated security. This custom golf course home was built by esteemed builder Arthur Rutenberg. It represents Rutenberg at his very best - stylish elegance, superior

Mark Lyda GENEROUS PROPERTY

433 E MacEwen Dr, Osprey, FL 34229
/39
$2,850 per month
- 3 Beds
- 2 Baths
- House for Rent
4429 Conchfish Ln, Osprey, FL 34229

Steps from Pine View School, Florida's #1 public school, with 2,008 sq. ft. of living space, this home features brand-new thick waterproof laminate wood flooring in all bedrooms and closets, an ocean-inspired guest bathroom, and tile throughout the main living areas for easy maintenance.Enjoy the covered lanai overlooking a private backyard, perfect for relaxing or entertaining, and take

JIA SONG Jia Song Realty

4429 Conchfish Ln, Osprey, FL 34229
/2
$1,330,000 Sold Jan 07, 2026

401 N Point Rd Unit 901, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,594 Sq Ft
- Built 2003
Last Sold Summary
- 24% Below List Price
- $513/SF
- 764 Days On Market
Current Estimated Value $1,302,735

Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

401 N Point Rd Unit 901, Osprey, FL 34229

/40
Est $295,120 Not Listed For Sale

163 Explorer Dr Unit 103, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,244 Sq Ft
- Built 2014
163 Explorer Dr Unit 103, Osprey, FL 34229

Last Sold Summary
- 14% Below List Price
- $276/SF
- 28 Days On Market
Last Sold Price $343,000

Last Listing Agent Lita Sciturro Smith LITA SCITURRO-SMITH LIC. REAL ESTATE BROKER

/73
$2,495,000
- 3 Beds
- 3.5 Baths
- 4,519 Sq Ft
852 MacEwen Dr, Osprey, FL 34229

**CHARMING and PRIVATE, GOLF COURSE ESTATE** is located behind the Secure Gates of the highly sought after Oaks Country Club community and offers a Lovely, Golf Course View of the 17th Fairway of the interior, Heron Golf Course. This Spacious, Light and Bright, Open Floorplan of OVER 4500sf entails 3-BEDS, 3 FULL and 1 HALF BATHS, Study/Den, Bonus Room / Entertaining area with Fireplace and

Mark Lyda GENEROUS PROPERTY

852 MacEwen Dr, Osprey, FL 34229
/53
$5,000 per month
- 2 Beds
- 2.5 Baths
- 1,950 Sq Ft
- Condo for Rent
260 Hidden Bay Dr Unit B-504, Osprey, FL 34229

Annual Turnkey Furnished or short term seasonal Penthouse on the Bay! If you want mesmerizing views of intracoastal waterway, Little Sarasota Bay, Casey Key, and the Gulf of Mexico in a beautiful, comfortable and roomy penthouse, then this could be your next home. This natural light filled delight is 2 bedrooms, each with en suite bathroom, separate office with large closet and glass French

Henry Rossi RENT SARASOTA

260 Hidden Bay Dr Unit B-504, Osprey, FL 34229
/2
$962,500 Sold Aug 07, 2025

742 Shadow Bay Way, Osprey, FL 34229
- 4 Beds
- 3 Baths
- 3,321 Sq Ft
- Built 2002
Last Sold Summary
- 12% Below List Price
- $290/SF
- 115 Days On Market
Current Estimated Value $936,907

Last Listing Agent Reeny Kaney RE/MAX ALLIANCE GROUP

742 Shadow Bay Way, Osprey, FL 34229

/34
Not Listed For Sale

201 Palm Air Dr, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 959 Sq Ft
- Built 1980
201 Palm Air Dr, Osprey, FL 34229

Last Sold Summary
- $162/SF
- 119 Days On Market
Last Sold Price $155,000

Last Listing Agent Roxane Solowey BERKSHIRE HATHAWAY HOMESERVICE

/60
$1,995,000
- 3 Beds
- 3 Baths
- 3,029 Sq Ft
401 N Point Rd Unit 1001, Osprey, FL 34229

**Rarely available 10th-floor penthouse corner residence offering 3,029 square feet with sweeping Gulf and Bay views.** Ideally situated behind the secure gates of the highly sought-after Preserve neighborhood within The Oaks Country Club, this exceptional condo features 3 Bedrooms plus Den, 3 Full Baths, Private 2-Car Garage, and climate-controlled storage. The open-concept floor plan is

Mark Lyda GENEROUS PROPERTY

401 N Point Rd Unit 1001, Osprey, FL 34229
/44
$6,500 per month
- 3 Beds
- 3 Baths
- 2,266 Sq Ft
- House for Rent
521 Habitat Blvd, Osprey, FL 34229

Stylish 3BR Pool Home w/ Office – 10 Mins to Beach ****SEASONAL RENTAL ONLY**** 90 Day minimum stay, Peak Season at $8,900/mo plus fees; Off Season at $6,500/mo plus fees. NOTE: Jan, Feb and March 2027 are Not Available. Your Gulf Coast getaway awaits at this beautifully furnished 3-bedroom, 3-bath pool home in the scenic Willowbend community of Osprey, FL. Ideal for mid-term stays, this spacious

Dave Holt PMI SOUTHWEST FLORIDA

521 Habitat Blvd, Osprey, FL 34229
/2
$210,000 Sold Oct 22, 2025

480 Blackburn Point Rd Unit 4, Osprey, FL 34229
- Built 2006
Last Sold Summary
- 7% Below List Price
- 5 Days On Market
Current Estimated Value $208,977

Last Listing Agent Daniel Treiman MICHAEL SAUNDERS & COMPANY

480 Blackburn Point Rd Unit 4, Osprey, FL 34229

/46
Est $561,208 Not Listed For Sale

2007 Cordes St, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 2,004 Sq Ft
- Built 2023
2007 Cordes St, Osprey, FL 34229

Last Sold Summary
- 1% Above List Price
- $276/SF
- 15 Days On Market
Last Sold Price $554,000

Last Listing Agent Lee Brewer RE/MAX

/73
$2,850,000
- 4 Beds
- 4 Baths
- 4,359 Sq Ft
662 Fernwalk Ln, Osprey, FL 34229

**EXCEPTIONAL, FULLY RENOVATED, COUNTRY CLUB ESTATE HOME OFFERING TRANQUIL LAKE AND GARDEN VIEWS** ideally positioned on a serene interior cul-de-sac lot in Flood Zone X (no flood insurance required). Located behind the secure gates of the highly sought-after Bayside neighborhood within The Oaks Country Club, just steps from Little Sarasota Bay. This expansive residence features 4 Bedrooms and 4

Mark Lyda GENEROUS PROPERTY

662 Fernwalk Ln, Osprey, FL 34229
/87
$6,950 per month
- 3 Beds
- 2 Baths
- 2,143 Sq Ft
- Condo for Rent
5100 Jessie Harbor Dr Unit 504, Osprey, FL 34229

CLOSE TO NOKOMIS BEACH! BOOKED JAN/FEB/MAR 2027. AVAILABLE APR 2027 $6,950/MONTH. Beautiful direct waterfront 5th Floor condo located in Blackburn Harbor Residences with breathtaking panoramic water views of Little Sarasota Bay, which can be seen from the living room, kitchen, primary bedroom suite, and spacious balcony! The condo comes turnkey furnished and has 3 bedrooms (3rd bedroom was

Chrissie Cummings JENNETTE PROPERTIES INC

5100 Jessie Harbor Dr Unit 504, Osprey, FL 34229
/2
$980,000 Sold Dec 09, 2025

385 N Point Rd Unit 903, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,778 Sq Ft
- Built 2000
Last Sold Summary
- 11% Below List Price
- $353/SF
- 41 Days On Market
Current Estimated Value $1,011,978

Last Listing Agent Ryan Ackerman COLDWELL BANKER REALTY

385 N Point Rd Unit 903, Osprey, FL 34229

/5
Not Listed For Sale

0 N Point Rd Unit A11454780, Osprey, FL 34229
0 N Point Rd Unit A11454780, Osprey, FL 34229

Last Sold Summary
- 218 Days On Market
Last Sold Price $850,000

Last Listing Agent Jennifer Arciniegas Cuadra Group LLC

/74
$1,695,000
- 3 Beds
- 3.5 Baths
- 3,066 Sq Ft
25 Sugar Mill Dr, Osprey, FL 34229

METICULOUSLY MAINTAINED AND THOUGHTFULLY UPDATED, THIS EXCEPTIONAL RESIDENCE IS PRIVATELY SITUATED ON A SERENE LOT WITH BEAUTIFUL GARDEN AND PRESERVE VIEWS. Located in Flood Zone “X” (no flood insurance required), the home is tucked behind the secure gates of the highly sought-after Bayside neighborhood within The Oaks Country Club, just steps from Little Sarasota Bay. The home offers 3 En Suite

Mark Lyda GENEROUS PROPERTY

25 Sugar Mill Dr, Osprey, FL 34229
/33
$2,595 per month
- 2 Beds
- 3.5 Baths
- 1,890 Sq Ft
- Townhouse for Rent
60 Bishops Court Rd Unit 114, Osprey, FL 34229

This is a rare opportunity to rent a luxury, unfurnished townhome located in the heart of the Oaks Preserve. Showcasing charming architectural details and quality finishes, this traditional-style home offers an inviting floor plan with two bedrooms, each featuring its own en-suite bath. The gracious living and dining areas flow seamlessly into a spacious and private outdoor living space that

Heidi Thompson STRINGER MANAGEMENT INC

60 Bishops Court Rd Unit 114, Osprey, FL 34229
/2
$340,000 Sold May 08, 2025

294 Hidden Bay Dr Unit 103, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,568 Sq Ft
- Built 2001
Last Sold Summary
- 20% Below List Price
- $217/SF
- 166 Days On Market
Current Estimated Value $334,658

Last Listing Agent Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

294 Hidden Bay Dr Unit 103, Osprey, FL 34229

/2
Est $302,555 Not Listed For Sale

4219 Frontier Ln Unit 105, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,244 Sq Ft
- Built 2019
4219 Frontier Ln Unit 105, Osprey, FL 34229

Last Sold Summary
- 18% Below List Price
- $297/SF
Last Sold Price $370,000

Last Listing Agent Stellar Non-Member Agent FL_MFRMLS

/49
$1,175,000 Pending
- 3 Beds
- 2.5 Baths
- 2,735 Sq Ft
219 Keel Way, Osprey, FL 34229

Under contract-accepting backup offers. **IMPRESSIVE, METICULOUSLY MAINTAINED, SINGLE-STORY, CUL DE SAC ESTATE in the Highly Sought-After SOUTHBAY Community** offers 3 BEDS, 2 FULL and 1 HALF BATHS plus STUDY/DEN – and is nearly 100% SOLAR-POWERED (details available)! This Custom and Updated home offers many premium features including elegant Bolivian woodwork, beautiful tile floors throughout,

Mark Lyda GENEROUS PROPERTY

219 Keel Way, Osprey, FL 34229
/39
$6,950 per month
- 3 Beds
- 2.5 Baths
- 1,839 Sq Ft
- Townhouse for Rent
101 Woodland Place, Osprey, FL 34229

Price Reduction and Now AVAILABLE FOR LEASE for FEBRUARY through APRIL 2026 at PINE RUN Condominiums in OSPREY, Florida! One month availability. 3BR/2.5BA Great SARASOTA Vacation Location! West of the Trail, Pine Run is an active community set in a tropical oasis of 20+ acres of wooded Florida landscape. This spacious corner unit townhouse is well FURNISHED. Beautifully decorated and full of

Patrice Ivan WAGNER REALTY

101 Woodland Place, Osprey, FL 34229
/2
$235,000 Sold Jun 13, 2025

109 Woodland Place, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,223 Sq Ft
- Built 1979
Last Sold Summary
- 6% Below List Price
- $192/SF
- 144 Days On Market
Current Estimated Value $221,371

Last Listing Agent Derek Edwards KELLER WILLIAMS ON THE WATER S

109 Woodland Place, Osprey, FL 34229

/24
Est $285,682 Not Listed For Sale

4224 Expedition Way Unit 105, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,135 Sq Ft
- Built 2016
4224 Expedition Way Unit 105, Osprey, FL 34229

Last Sold Summary
- 18% Below List Price
- $308/SF
- 0 Days On Market
Last Sold Price $350,000

Last Listing Agent Randal Longo KEYS REALTY REDEFINED LLC

/82
$1,295,000
- 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
/42
$5,900 per month
- 3 Beds
- 3 Baths
- 2,545 Sq Ft
- Condo for Rent
3603 N Point Rd Unit 602, Osprey, FL 34229

**FURNISHED, 3-BED / 3-FULL BATH, Over 2500sf CONDO with FANTASTIC VIEW** features an Open Floorplan and is located behind the Secure Gates of the highly sought after Oaks-Preserve, Country Club neighborhood. As you emerge from your private elevator lobby, you will be enthralled by the Spacious interior which boasts beautiful Crown Moldings, Hardwood Floors, a well-equipped Kitchen with granite

Mark Lyda GENEROUS PROPERTY

3603 N Point Rd Unit 602, Osprey, FL 34229
/55
$480,000 Sold May 14, 2025

564 Meadow Sweet Cir, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 1,808 Sq Ft
- Built 2003
Last Sold Summary
- 15% Below List Price
- $265/SF
- 57 Days On Market
Current Estimated Value $468,493

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

564 Meadow Sweet Cir, Osprey, FL 34229

/4
Est $53,112 Not Listed For Sale

570 Blackburn Point Rd Unit 1-SIES, Osprey, FL 34229
- Studio
- 45,244 Sq Ft
570 Blackburn Point Rd Unit 1-SIES, Osprey, FL 34229

Last Sold Summary
- 11% Below List Price
- $1/SF
- 21 Days On Market
Last Sold Price $60,000

Last Listing Agent Christopher Pelletier CHRISTOPHER PELLETIER BROKER

/75
$2,100,000
- 4 Beds
- 5.5 Baths
- 4,346 Sq Ft
538 Dove Pointe, Osprey, FL 34229

**ELEGANT UPDATED RESIDENCE IN THE OAKS | MODERN COMFORT ON A .83-ACRE CORNER LOT** Welcome to 538 Dove Pointe, an exceptional residence in the secure and gated Oaks Country Club community in Osprey, Florida. Set on a generous .83-acre elevated lot, this beautifully landscaped property offers the perfect combination of privacy, sophistication, and modern comfort. Built in 2002, this newer home

Mark Lyda GENEROUS PROPERTY

538 Dove Pointe, Osprey, FL 34229
/74
$7,750 per month
- 3 Beds
- 2 Baths
- 2,058 Sq Ft
- Condo for Rent
14041 Bellagio Way Unit 316, Osprey, FL 34229

AVAILABLE FOR SEASON 2027 - 3 MONTH MIN REQUIRED. MINUTES TO CASEY KEY & NOKOMIS BEACH! Welcome to BELLAGIO at Osprey Harbor Village, offering luxurious waterfront living! This turnkey direct waterfront condo has 3 beds/2 baths plus a den is the perfect place for your next Florida vacation, located in a private gated community. As you step off the elevator, you are basically outside this 3rd

Chrissie Cummings JENNETTE PROPERTIES INC

14041 Bellagio Way Unit 316, Osprey, FL 34229
/2
$350,000 Sold Oct 16, 2025

240 Patterson Ave, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 1,360 Sq Ft
- Built 1982
Last Sold Summary
- 7% Below List Price
- $257/SF
- 157 Days On Market
Current Estimated Value $340,597

Last Listing Agent Janice Melzer Langa COLDWELL BANKER REALTY

240 Patterson Ave, Osprey, FL 34229

/12
Est $24,035 Not Listed For Sale

570 Blackburn Point Rd Unit 9-LIDO, Osprey, FL 34229
- Studio
- 45,244 Sq Ft
570 Blackburn Point Rd Unit 9-LIDO, Osprey, FL 34229

Last Sold Summary
- 11% Below List Price
- $1/SF
- 69 Days On Market
Last Sold Price $27,000

Last Listing Agent Stephen Mason PREFERRED SHORE LLC

/62
$850,000
- 2 Beds
- 2 Baths
- 2,310 Sq Ft
13 Bayhead Ln, Osprey, FL 34229

**IMPRESSIVE, MOVE-IN READY, POOL HOME in the Secure and Coveted OAKS PRESERVE, MAINTENANCE-FREE COMMUNITY** This residence boasts an open floor plan that is ideal for entertaining, along with a screened and spacious outdoor pool area that provides privacy and overlooks a nature preserve. Recent updates include a new kitchen, bathrooms, flooring, fans, a four-year-old roof, a newly pavered

Mark Lyda GENEROUS PROPERTY

13 Bayhead Ln, Osprey, FL 34229
/10
$2,500 per month
- 1 Bed
- 1 Bath
- 623 Sq Ft
- Condo for Rent
51 Mac Ewen Dr Unit 1, Osprey, FL 34229

***AVAILABLE MAY 2026 THRU JULY 2026 AND THEN AGAIN IN NOVEMBER 2026*** Welcome to THE OAK community, it's gated 24/7. private as private can be. Drenched in value and a fantastic community located in South Sarasota. Open plan, easy to show! Close to Siesta Key, Costco restaurants very convenient to all the amenities Sarasota has to offer.

Anthony DeLuca AUDREY RAIN RENTALS, INC

51 Mac Ewen Dr Unit 1, Osprey, FL 34229
/2
$1,285,000 Sold Jun 30, 2025

393 N Point Rd Unit 801, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 3,029 Sq Ft
- Built 2001
Last Sold Summary
- 22% Below List Price
- $424/SF
- 204 Days On Market
Current Estimated Value $1,239,858

Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

393 N Point Rd Unit 801, Osprey, FL 34229

/50
Est $546,327 Not Listed For Sale

2006 Preymore St, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 2,004 Sq Ft
- Built 2023
2006 Preymore St, Osprey, FL 34229

Last Sold Summary
- 2% Above List Price
- $267/SF
- 10 Days On Market
Last Sold Price $535,000

Last Listing Agent Lee Brewer RE/MAX

Showing Results 81 - 120, Page 3 of 18

Florida Sarasota County Osprey

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