Osprey, FL Homes

/99
$1,385,000
- 3 Beds
- 3.5 Baths
- 3,112 Sq Ft
156 Bishopscourt Rd, Osprey, FL 34229

This stunning 3 bedroom, 3.5 bath home, designed by the renowned architect Frank Folsom Smith, stands out with its unique design. The charming Cape Cod style sets the stage for comfortable, graceful living. The home, with beautiful wood floor throughout the main living areas, features a Sonos stereo sound system. The backyard, overlooking the preserve, and offering a lovely sunset exposure, is a

Steve Abbe COLDWELL BANKER REALTY

156 Bishopscourt Rd, 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
/2
$640,000 Sold Jun 20, 2025
- 2,590 Sq Ft
- $247/SF
- 119 Days On Market
- 3 Beds
- 3 Baths
- Built 1999
455 Park Trace Blvd, Osprey, FL 34229

CURRENTLY BEST VALUE IN OSPREY! Premium Lakefront lot with Stunning Views from Nearly Every Room! Discover the perfect blend of comfort, convenience, and breathtaking views in this Park Trace Estates beauty. This home features a NEW ROOF (Jan. 2024,) New Energy efficient A/C (May 2024) and brand new pool pump and motor (March 2025), AND...newly refurbished patio and pool deck in April. Ideally

Kim Azar-Calka MICHAEL SAUNDERS & COMPANY

455 Park Trace Blvd, Osprey, FL 34229

/24
Est $592,982 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,975 Sq Ft
2001 Cordes St, Osprey, FL 34229

2001 Cordes St, Osprey, FL 34229

/68
$1,375,000 Open Sun 1PM - 4PM
- 3 Beds
- 2 Baths
- 2,850 Sq Ft
17 Bayhead Ln, Osprey, FL 34229

Welcome to an exquisitely revitalized estate set amidst a stunning landscape that is sure to impress. Located “West of Trail” in The Oaks Preserve, you will experience an unparalleled country club lifestyle on Florida’s Gulf Coast. As you step through the grand front entry, you are welcomed by a blend of contemporary sophistication and modern luxury, transforming this residence into a true

Ashley LeRoy CORNERSTONE R.E OF SW FL

17 Bayhead Ln, Osprey, FL 34229
/74
$7,500 per month
- 3 Beds
- 2 Baths
- 2,058 Sq Ft
- Condo for Rent
14041 Bellagio Way Unit 316, Osprey, FL 34229

NOW AVAILABLE FOR APRIL AND OFF-SEASON MONTHS 2025 AND JAN-APRIL 2026! 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 floor end unit. Upon

Chrissie Cummings JENNETTE PROPERTIES INC

14041 Bellagio Way Unit 316, Osprey, FL 34229
/2
$395,000 Sold Jun 16, 2025
- Land
- 0.52 Acre
- $759,615 per Acre
- 30 Days On Market
109 Burney Rd, Osprey, FL 34229

Build your dream home on this HALF ACRE lot situated on a quiet dead-end street with no neighboring homes on 3 sides. This property offers a rare sense of seclusion and tranquility, perfect for those seeking a peaceful retreat. The property includes a well-maintained home with two bedrooms, one and a half bathrooms, an outdoor shower, three large sheds, two extra-long driveways, perfect for

Lori Madden MANGROVE REALTY ASSOCIATES

109 Burney Rd, Osprey, FL 34229

/48
Est $376,224 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,574 Sq Ft
123 Revolution Way Unit 101, Osprey, FL 34229

123 Revolution Way Unit 101, Osprey, FL 34229

/87
$995,000
- 3 Beds
- 2 Baths
- 2,606 Sq Ft
105 Turquoise Ln, Osprey, FL 34229

Welcome to Emerald Woods, a desired cul-de-sac within The Oaks Preserve, and this private LeeWetherington custom home that will check all the boxes, and more. Situated on one of thelargest lots and surrounded by preserve for privacy, you’ll find essence and elegance as thecolor palette interplays with natural light, and the southern facing lanai and pool will be whereyou can enjoy

Rosalie Phillips MICHAEL SAUNDERS & COMPANY

105 Turquoise Ln, Osprey, FL 34229
/68
$21,000 per month
- 4 Beds
- 6 Baths
- 9,081 Sq Ft
- House for Rent
854 MacEwen Dr, Osprey, FL 34229

**RENTAL OPPORTUNITY (unfurnished)** SPACIOUS, LUXURIOUS and BEAUTIFULLY RENOVATED, GOLF COURSE ESTATE situated behind the SECURE GATES of The Oaks Country Club Community, Boasting OVER 9,000sf and located on a prominent, private cul de sac lot of Over 3/4 Acres. Expansive room abounds in this LIGHT and BRIGHT Open Floorplan consisting of 4 Beds + 4/2 Baths + Office/Library + Home Theater + Game

Mark Lyda GENEROUS PROPERTY

854 MacEwen Dr, Osprey, FL 34229
/2
$720,000 Sold Jun 16, 2025
- 2,320 Sq Ft
- $310/SF
- 130 Days On Market
- 4 Beds
- 3 Baths
- Built 2005
518 Luminary Blvd, Osprey, FL 34229

Discover the perfect blend of comfort and sophistication in this meticulously maintained home located in the highly desirable Willowbend community. The striking architecture of the Ashley floor plan, complete with a rare three-car garage with epoxy floor, enhances the property’s curb appeal. Enjoy peace of mind with hurricane impact-rated doors, windows and sliders throughout the residence. Step

Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

518 Luminary Blvd, Osprey, FL 34229

/61
Est $385,947 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,574 Sq Ft
4185 Frontier Ln Unit 102, Osprey, FL 34229

4185 Frontier Ln Unit 102, Osprey, FL 34229

/95
$900,000
- 3 Beds
- 3 Baths
- 2,778 Sq Ft
401 N Point Rd Unit 304, Osprey, FL 34229

Give yourself the gift of refined living in this expansive 2,778 square foot residence—the largest non-penthouse floor plan available in Meridian at The Oaks Preserve. Every detail in this meticulously maintained, and beautifully updated condominium has been thoughtfully designed to offer comfort, sophistication, and versatility, making it the perfect sanctuary for luxury living every day! Step

Steve Abbe COLDWELL BANKER REALTY

401 N Point Rd Unit 304, 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 NOVEMBER 2025 THRU JANUARY 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
$725,000 Sold Jun 13, 2025
- 2,678 Sq Ft
- $271/SF
- 75 Days On Market
- 4 Beds
- 3 Baths
- Built 2005
608 Crane Prairie Way, Osprey, FL 34229

One or more photo(s) has been virtually staged. Exceptional Opportunity on this Newly Priced Gem with stunning views and privacy! Discover your dream home in this stunning 2,678 square foot Wyndham model by Lee Wetherington, one of the largest in the maintenance-free community of Willowbend in Osprey. The owner has added improvements in excess of $150K since their purchase and has been lovingly

Linda Williams GULF SHORES REALTY

608 Crane Prairie Way, Osprey, FL 34229

/59
Est $374,374 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,574 Sq Ft
99 Explorer Dr Unit 102, Osprey, FL 34229

99 Explorer Dr Unit 102, Osprey, FL 34229

/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
/25
$4,500 per month
- 3 Beds
- 2 Baths
- 1,528 Sq Ft
- Condo for Rent
152 Navigation Cir Unit 107, Osprey, FL 34229

Seasonal and short term rental Get out of the cold and into the sunshine in this newer 3/2 condo in the gated community of Bay Street Village in Osprey. This condo is an end unit with an open floor plan for ease of entertaining and family time. The extra windows flood the unit with natural sun light. The kitchen is a natural gathering point with solid wooden cabinetry, topped with slab granite

Henry Rossi RENT SARASOTA

152 Navigation Cir Unit 107, Osprey, FL 34229
/2
$235,000 Sold Jun 13, 2025
- 1,223 Sq Ft
- $192/SF
- 144 Days On Market
- 2 Beds
- 2 Baths
- Built 1979
109 Woodland Place, Osprey, FL 34229

Welcome to 109 Woodland Place, a serene retreat nestled within the lush, natural surroundings of the Pine Run community in Osprey, Florida. This charming 2-bedroom, 2-bathroom condominium offers 1,223 square feet of thoughtfully designed living space, seamlessly blending comfort with the beauty of its environment. As you enter, you’ll be greeted by soaring ceilings and an open floor plan that

Derek Edwards KELLER WILLIAMS ON THE WATER S

109 Woodland Place, Osprey, FL 34229

/42
Not Listed For Sale
- 2 Beds
- 2 Baths
- 673 Sq Ft
36 Siesta Cir W, Osprey, FL 34229

36 Siesta Cir W, Osprey, FL 34229

/45
$479,900
- 2 Beds
- 2 Baths
- 1,574 Sq Ft
780 Sarabay Rd Unit 16, Osprey, FL 34229

Boater's Paradise! Welcome to Heron Bay Club, an exclusive enclave of just 25 uniquely designed villas situated on 11 acres along the Little Sarasota Bay. This spacious 2-bedroom, 2-bath villa features a versatile bonus room—perfect for a home office, den, or even a guest bedroom. Inside, you'll find a thoughtfully updated interior with a renovated kitchen featuring raised panel maple cabinetry

Mark Segreto RMS ELITE PROPERTIES

780 Sarabay Rd Unit 16, Osprey, FL 34229
/21
$2,300 per month
- 2 Beds
- 2 Baths
- 1,244 Sq Ft
- Property for Rent
184 Explorer Dr Unit 184, Osprey, FL 34229

Property available for $2300 from April 1,2024 till November 30,2024. Tenant pays electricity and internet. Available for season 2024/2025 for $4500. If you are looking for the perfect Florida lifestyle, this is it. Conveniently located between Sarasota and Venice with #1 Siesta Key beach close by, this darling two-bedroom, two-bath, impeccably maintained, property move-in ready. Located on the

Claudia Dybala DALTON WADE INC

184 Explorer Dr Unit 184, Osprey, FL 34229
/2
$685,000 Sold Jun 12, 2025
- 2,203 Sq Ft
- $311/SF
- 5 Days On Market
- 3 Beds
- 3 Baths
- Built 2000
385 N Point Rd Unit 503, Osprey, FL 34229

Experience luxury coastal living in this 5th-floor condo, offering breathtaking water and Preserve views that rival those of higher floors. This residence in Meridian at The Oaks Preserve features 3 bedrooms, 3 full baths, and a dining room, all enhanced with new furnishings. Offered turnkey, all it needs is for you to move in and start living a carefree lifestyle on Florida’s gorgeous Gulf

Steve Abbe COLDWELL BANKER REALTY

385 N Point Rd Unit 503, Osprey, FL 34229

/4
Est $30,614 Not Listed For Sale
- Studio
- 45,244 Sq Ft
570 Blackburn Point Rd Unit 28, Osprey, FL 34229

570 Blackburn Point Rd Unit 28, Osprey, FL 34229

/38
$959,000
- 3 Beds
- 2.5 Baths
- 2,676 Sq Ft
238 Lookout Point Dr, Osprey, FL 34229

Nestled in the heart of Southbay Yacht & Racquet Club, this exquisitely renovated and impeccably maintained residence offers an enviable lifestyle for those who cherish the water. The journey begins at the inviting brick paver entry, guiding you into a gracious foyer that sets the tone for the home's elegant charm. Upon entering, you are welcomed by a spacious great room featuring new tile

Stephanie Church COLDWELL BANKER REALTY

238 Lookout Point Dr, Osprey, FL 34229
/2
$1,700,000 Sold Jun 12, 2025
- 2,315 Sq Ft
- $734/SF
- 108 Days On Market
- 3 Beds
- 3 Baths
- Built 1972
525 S Shore Dr, Osprey, FL 34229

This redesigned mid-century styled 3-bedroom Bayfront home has been fully remastered with entertaining in mind. The stunning outdoor oasis says it all, with a panoramic view pool cage, a large, covered area, outdoor kitchen, and an amazing pool and spa featuring a stone waterfall and propane-fueled fire sconces. The pool cage was recently rescreened with no see um screen. Inside, the split

Andree Huffine COLDWELL BANKER REALTY

525 S Shore Dr, Osprey, FL 34229

/68
Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,247 Sq Ft
273 Sun Air Cir, Osprey, FL 34229

273 Sun Air Cir, Osprey, FL 34229

/72
$970,000
- 4 Beds
- 3 Baths
- 3,011 Sq Ft
1085 Mallard Marsh Dr, Osprey, FL 34229

Welcome to lakefront perfection—nothing to do but relax and enjoy. This beautifully updated Rutenberg Homes residence in the Woodlands at Rivendell offers over 3,000 sq ft of stylish living space, just 2 miles from the Gulf of Mexico.The home features 4 bedrooms, 3 baths, and an upstairs bonus room, with extensive 2023 updates including elegant ceramic tile flooring, a chef’s kitchen, modern

Veronica Manes MICHAEL SAUNDERS & COMPANY

1085 Mallard Marsh Dr, Osprey, FL 34229
/2
$3,525,000 Sold Jun 06, 2025
- 5,279 Sq Ft
- $668/SF
- 124 Days On Market
- 5 Beds
- 5 Baths
- Built 2007
275 Lookout Point Dr, Osprey, FL 34229

This stunning waterfront residence in Southbay Yacht and Racquet Club is a gem on Florida’s Gulf Coast where boats are accommodated in a deep-water marina for low fees. Boasting over 135 feet of water frontage and surrounded by lush tropical landscaping and majestic Royal Palms. Its refined curb appeal sets it apart as a one-of-a-kind property. The custom John Cannon home features a grand double

Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

275 Lookout Point Dr, Osprey, FL 34229

/24
Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,055 Sq Ft
338 Tropic Dr, Osprey, FL 34229

338 Tropic Dr, Osprey, FL 34229

/67
$1,045,000
- 2 Beds
- 2 Baths
- 2,071 Sq Ft
227 Saint James Park, Osprey, FL 34229

**TURNKEY FURNISHED, ELEGANT and TRADITIONAL ESTATE by Famed Architect, Bo MacEwen, on the Single Largest 0.32 Acre Cul De Sac Lot in the Popular SAINT JAMES PARK neighborhood in The Oaks Country Club. NEW ROOF (2024), HURRICANE IMPACT WINDOWS and SLIDING DOORS, FLOOD ZONE “X500”. Overlooking the Eagle Golf Course and Ideally Located near the Clubhouse and Campus of World Class Amenities, this

Mark Lyda GENEROUS PROPERTY

227 Saint James Park, Osprey, FL 34229
/2
$640,000 Sold Jun 04, 2025
- 2,234 Sq Ft
- $286/SF
- 15 Days On Market
- 3 Beds
- 3 Baths
- Built 2003
519 Habitat Blvd, Osprey, FL 34229

This exquisite three-bedroom, three-bath-plus-den home by Lee Wetherington Homes exemplifies intelligent design and beauty in the community of Willowbend. The Savannah floor plan is a rare great room plan with one of the few natural gas fireplaces in the neighborhood. This is the focal point of the home with stacked flagstone and a beautiful mantel flanked in shelving. The residence features an

Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

519 Habitat Blvd, Osprey, FL 34229

/79
Est $655,097 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,937 Sq Ft
250 Hidden Bay Dr Unit A203, Osprey, FL 34229

250 Hidden Bay Dr Unit A203, Osprey, FL 34229

/2
$575,904 New Construction
- 3 Beds
- 2 Baths
- 1,356 Sq Ft
791 S Tamiami Trail Unit 103, Osprey, FL 34229

Pre-Construction. To be built. PRE CONSTRUCTION STARTING FROM $575,904. 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 103, Osprey, FL 34229
/2
$1,197,000 Sold May 30, 2025
- 3,321 Sq Ft
- $360/SF
- 20 Days On Market
- 3 Beds
- 5 Baths
- Built 1991
223 Saint James Park, Osprey, FL 34229

Luxury Clubside Living at The Oaks – featuring Elegance and Comfort! Stunning Clubside residence in the upscale Oaks Club, offering the perfect blend of estate charm and modern luxury. Nestled among grand oak trees with partial lake and full golf course views, this beautifully upgraded home offers 3,321 sq ft of refined living space in one of Sarasota’s most exclusive communities. You’re

John Hockenberry RE/MAX ALLIANCE GROUP

223 Saint James Park, Osprey, FL 34229

/13
Est $817,000 Not Listed For Sale
0 Cezanne Dr Unit A4556644, Osprey, FL 34229

0 Cezanne Dr Unit A4556644, Osprey, FL 34229

/2
$527,904 New Construction
- 2 Beds
- 2 Baths
- 952 Sq Ft
791 S Tamiami Trail Unit 102, Osprey, FL 34229

Pre-Construction. To be built. PRE CONSTRUCTION STARTING FROM $527,904. NO FLOOD INSURANCE REQUIRED. NOW TAKING RESERVATIONS ON THIS NEW VENICE ISLAND CONDOMINIUM COMMUNITY KNOWN AS ISOLA CASA! 36 CONDOMINIUM UNITS WITHIN 4 SEPARATE BUILDINGS THAT INCLUDE ELEVATORS. THIS UNIT BOASTS 2 BEDROOMS, 2 BATHROOMS WITH A SCREENED LANAI AND HAS A 1-CAR DETACHED GARAGE. (3 BEDROOM AND 2 BATH UNITS ALSO

Laurie Eshleman PRO GROUP REALTY & PROP MGT

791 S Tamiami Trail Unit 102, Osprey, FL 34229
/2
$904,900 Sold May 30, 2025
- 2,705 Sq Ft
- $335/SF
- 5 Days On Market
- 4 Beds
- 3 Baths
- Built 1989
336 Pine Ranch Rd E, Osprey, FL 34229

Nestled on a rare one-acre private oasis, this stunning lakefront home in Osprey offers the perfect blend of tranquility and convenience. With mature landscaping, majestic pine trees, and abundant wildlife, this is a true sanctuary—yet you're just minutes from Pine View School (Ranked #18 in the nation), Siesta Key Beach, The Legacy Trail, and US-41. Near I-75, centrally located between Venice

Marco Guadagnini PREFERRED SHORE LLC

336 Pine Ranch Rd E, Osprey, FL 34229

/29
Est $533,342 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,680 Sq Ft
313 Sorrento Dr, Osprey, FL 34229

313 Sorrento Dr, Osprey, FL 34229

/100
$1,250,000 Pending
- 4 Beds
- 3.5 Baths
- 3,479 Sq Ft
1484 Seafarer Dr, Osprey, FL 34229

Under contract-accepting backup offers. Welcome to Southbay Yacht & Racquet Club, one of the Gulf Coast’s most coveted communities—where every day feels like a vacation! Southbay boasts a world-class private marina with 172 deep-water slips, accommodating yachts up to 55 feet, along with personal watercraft and kayaks. Slip rentals are available and offered at a highly competitive rate, making

Seth Westerberg EXP REALTY LLC

1484 Seafarer Dr, Osprey, FL 34229

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