Osprey, FL Homes

/80
$2,995,000
- 4 Beds
- 4 Baths
- 4,359 Sq Ft
662 Fernwalk Ln, Osprey, FL 34229

**FANTASTIC, FULLY RENOVATED ESTATE with LAKE / GARDEN VIEW is situated on a SERENE, INTERIOR, CUL-DE-SAC lot with NO FLOOD concern (Zone “X”) behind the Secure Gates of the highly sought after Bayside neighborhood within The Oaks Country Club community, just steps from Little Sarasota Bay. An Expansive Floorplan entails 4-BEDs plus 4-FULL BATHS while a full list of EXCEPTIONAL FEATURES is

Mark Lyda GENEROUS PROPERTY

662 Fernwalk Ln, Osprey, FL 34229
/33
$3,695 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
$285,000 Sold May 30, 2025
- 1,255 Sq Ft
- $227/SF
- 112 Days On Market
- 2 Beds
- 2 Baths
- Built 1985
7102 Jessie Harbor Dr, Osprey, FL 34229

Spectacular views in all directions at highly desired Blackburn Harbor in Osprey. Tucked back and surrounded by mature and well groomed grounds you’ll park in your private under building parking space near your own large secured storage unit. Elevators take you up to Unit 71 where you’ll immediately appreciate the opportunity to utilize the covered outdoor space at the condo entrance to enjoy

Chris Rankin RE/MAX PALM REALTY

7102 Jessie Harbor Dr, Osprey, FL 34229

/46
Est $616,357 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,004 Sq Ft
2007 Cordes St, Osprey, FL 34229

2007 Cordes St, Osprey, FL 34229

/82
$4,195,000
- 4 Beds
- 6 Baths
- 9,081 Sq Ft
854 MacEwen Dr, Osprey, FL 34229

One or more photo(s) has been virtually staged. **NEWLY RENOVATED, SPACIOUS, GOLF COURSE ESTATE** Boasts OVER 9,000sf and is situated 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 Room w/ Wet Bar, Loft, Balcony, etc. and even includes highly coveted,

Mark Lyda GENEROUS PROPERTY

854 MacEwen Dr, Osprey, FL 34229
/36
$7,200 per month
- 3 Beds
- 2.5 Baths
- 1,839 Sq Ft
- Townhouse for Rent
101 Woodland Place, Osprey, FL 34229

Now AVAILABLE FOR LEASE WINTER SEASON 2026 at PINE RUN Condominiums in Osprey, Florida! 3BR/2.5BA Location! Location! West of the Trail, Pine Run is a waterfront tropical oasis of 20+ acres of wooded Florida landscape. This spacious corner unit townhouse is well FURNISHED. Beautifully decorated and full of light and color with vaulted ceiling in the main Great Room. Custom designed Kitchen is

Patrice Ivan WAGNER REALTY

101 Woodland Place, Osprey, FL 34229
/2
$855,000 Sold May 30, 2025
- 2,235 Sq Ft
- $383/SF
- 211 Days On Market
- 3 Beds
- 3.5 Baths
- Built 2006
14021 Bellagio Way Unit 311, Osprey, FL 34229

Immerse yourself in the incredible views of Little Sarasota Bay & the Intracoastal waterway from this 3rd floor beautiful & spacious condominium. This upgraded end unit features 3 ensuite bedrooms, plus den, half bath & interior laundry room. The kitchen is a cook's delight with premium granite, upgraded wood cabinets & stainless steel appliances. The Primary bedroom offers expansive bay views &

Kristin O'Connor GULF TO BAY SOTHEBY'S INTERNAT

14021 Bellagio Way Unit 311, 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

/62
$1,795,000
- 3 Beds
- 3.5 Baths
- 4,241 Sq Ft
909 MacEwen Dr, Osprey, FL 34229

**STUNNING GOLF COURSE ESTATE in the Highly Sought-After OAKS COUNTRY CLUB Community** situated on an Over Half Acre Lot overlooking the 12th Fairway of the interior, HERON GOLF COURSE. With its delightful curb appeal and manicured landscape, this splendid residence offers 3 BEDROOMS + Spacious Executive Office/Study, 3 FULL and 1 HALF BATHS, High Ceilings, Crown Moldings, Gas Fireplace,

Mark Lyda GENEROUS PROPERTY

909 MacEwen Dr, 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
/62
$560,000 Sold May 29, 2025
- 1,935 Sq Ft
- $289/SF
- 68 Days On Market
- 3 Beds
- 2 Baths
- Built 1984
221 Sorrento Dr, Osprey, FL 34229

Discover your slice of paradise in the highly sought-after boating community of Sorrento Shores. This meticulously maintained and updated 3 bedroom, 2 bath home offers an unapparelled blend of comfort, convenience, and outdoor living, all west of Hwy 41.Key Features. *** Prime location: Nestled in Sorrento Shores, just minutes from Nokomis Beach, Oscar Scherer State Park, and an array of dining

Glenn Davis COLDWELL BANKER SARASOTA CENT.

221 Sorrento Dr, Osprey, FL 34229

/2
Est $326,418 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,244 Sq Ft
4219 Frontier Ln Unit 105, Osprey, FL 34229

4219 Frontier Ln Unit 105, Osprey, FL 34229

/43
$780,250 New Construction
- 3 Beds
- 2 Baths
- 1,937 Sq Ft
280 Hidden Bay Dr Unit 202, Osprey, FL 34229

READY FOR IMMEDIATE OCCUPANCY!Modern Elegance at Edgewater: A Luxurious Haven Overlooking Little Sarasota BayStep into a world of contemporary sophistication with this new construction condominium nestled in the eminent enclave of Edgewater at Hidden Bay. Boasting 1937 square feet, this meticulously crafted residence offers three bedrooms, two bathrooms, and an inviting office space for your

Mike Aveni KELLER WILLIAMS ISLAND LIFE REAL ESTATE

280 Hidden Bay Dr Unit 202, Osprey, FL 34229
/74
$7,900 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
$1,150,000 Sold May 28, 2025
- 2,521 Sq Ft
- $456/SF
- 20 Days On Market
- 2 Beds
- 3 Baths
- Built 1981
327 Sea Anchor Dr, Osprey, FL 34229

In the sought-after Southbay Yacht & Racquet Club, one of the premier boating communities on the southwest coast of Florida, this stunning home offers the ultimate in luxury living. With a community-owned marina and an expansive open layout, this property creates an ideal setting for relaxation and entertaining. This updated residence boasts volume ceilings, two fireplaces, built-in cabinetry and

Lisa Napolitano PREMIER SOTHEBYS INTL REALTY

327 Sea Anchor Dr, Osprey, FL 34229

/24
Est $341,406 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,135 Sq Ft
4224 Expedition Way Unit 105, Osprey, FL 34229

4224 Expedition Way Unit 105, Osprey, FL 34229

/57
$1,595,000 New Construction
- 3 Beds
- 3.5 Baths
- 2,913 Sq Ft
360 N Point Rd, Osprey, FL 34229

**DON’T WAIT TO BUILD!** EXQUISITE, NEWLY-CONSTRUCTED and NEVER LIVED-IN, SPANISH MISSION STYLE home behind the Secure Gates of the COVETED, OAKS PRESERVE Country Club Neighborhood on Sarasota Bay waters offers superb attention to detail. This Custom-Built residence boasts 3 EN SUITE BEDROOMS + 3 FULL and 1 HALF BATHS and a desirable Open Floorplan concept. A well-equipped Chef’s Kitchen

Mark Lyda GENEROUS PROPERTY

360 N Point Rd, 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
$85,000 Sold May 23, 2025
- 959 Sq Ft
- $89/SF
- 87 Days On Market
- 2 Beds
- 2 Baths
- Built 1978
199 Palm Air Dr, Osprey, FL 34229

MOTIVATED SELLER, BRING ALL OFFERS!!! Handyman special in a great location, the recent hurricane damaged the carport, shed, and Florida room. Priced for plenty of equity after repairs are made. The highly sought-after Arbors Mobile Home Park in Osprey is where location truly matters! This mobile home offers a perfect blend of comfort and convenience. With 2 bedrooms, 2 baths, and an inviting

Allison Bollero KELLER WILLIAMS ISLAND LIFE REAL ESTATE

199 Palm Air Dr, Osprey, FL 34229

/4
Est $54,892 Not Listed For Sale
- Studio
- 45,244 Sq Ft
570 Blackburn Point Rd Unit 1-SIES, Osprey, FL 34229

570 Blackburn Point Rd Unit 1-SIES, Osprey, FL 34229

/70
$479,000 Pending
- 3 Beds
- 2 Baths
- 1,904 Sq Ft
26 Bay Acres Ave, Osprey, FL 34229

Under contract-accepting backup offers. Discover this hidden gem in the sought-after waterfront community in Bay Acres, positioned West of the Trail with direct access to the Intracoastal Waterway situated on .037 acres that is completely fenced in for privacy! This beautifully renovated home has 3 spacious bedrooms and 2 bathrooms across 1,904 sqft, offering a split bedroom floor plan for

Erica Giesler RE/MAX ALLIANCE GROUP

26 Bay Acres Ave, 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
$665,000 Sold May 23, 2025
- 1,922 Sq Ft
- $346/SF
- 125 Days On Market
- 3 Beds
- 3 Baths
- Built 1964
123 Tina Island Dr, Osprey, FL 34229

Spectacular lot and setting for home priced under county tax appraisal. This is your opportunity to own a waterfront property in the Sorrento Shores neighborhood in Osprey. This 3 bedroom, 3 bath pool home is ready for its new owners to renovate the property with cosmetic updates to create your new dream space. This property is a great investment for you to enjoy your future activities and

Glenn Davis COLDWELL BANKER SARASOTA CENT.

123 Tina Island Dr, Osprey, FL 34229

/12
Est $24,730 Not Listed For Sale
- Studio
- 45,244 Sq Ft
570 Blackburn Point Rd Unit 9-LIDO, Osprey, FL 34229

570 Blackburn Point Rd Unit 9-LIDO, Osprey, FL 34229

/53
$649,995 Pending
- 4 Beds
- 3 Baths
- 2,256 Sq Ft
695 Rivendell Blvd, Osprey, FL 34229

Under contract-accepting backup offers. Welcome to 695 Rivendell Boulevard in Osprey, Florida – a beautifully maintained home offering comfort, style, and an unbeatable location. Just minutes from the Gulf Coast’s renowned beaches, shopping, and dining, this property features a host of recent upgrades designed for modern living. Hurricane protection includes a new garage door (2018) and Jansen

Dan Henson DALTON WADE INC

695 Rivendell Blvd, 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
$1,020,000 Sold May 22, 2025
- 2,909 Sq Ft
- $351/SF
- 14 Days On Market
- 3 Beds
- 3 Baths
- Built 1986
284 Lookout Point Dr, Osprey, FL 34229

Welcome to the much sought after Southbay Yacht and Racquet Club!!! You can be on vacation all year long with the private marina that has 172 boat slips that can accommodate yachts up to 55 feet. This one of a kind private marina will also accommodate personal water crafts and kayaks too!!. Our boat slip rentals are based on availability with a very attractive quarterly fee as compared to other

Carol Thompson ROYAL PALM REALTY

284 Lookout Point Dr, Osprey, FL 34229

/50
Est $577,842 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,004 Sq Ft
2006 Preymore St, Osprey, FL 34229

2006 Preymore St, Osprey, FL 34229

/100
$1,550,000
- 3 Beds
- 2.5 Baths
- 2,611 Sq Ft
462 E MacEwen Dr, Osprey, FL 34229

This completely remodeled home in The Oaks Clubside, set on nearly an acre of mature, meticulously landscaped grounds, is pure perfection. Nestled behind the gates of The Oaks Clubside, this residence is a masterful blend of classic elegance and contemporary sophistication. Arriving at the property, you are greeted by a striking full-circle driveway—a graceful approach that not only enhances the

Steve Abbe COLDWELL BANKER REALTY

462 E MacEwen Dr, Osprey, FL 34229
/47
$5,000 per month
- 2 Beds
- 2 Baths
- 1,568 Sq Ft
- Condo for Rent
293 Hidden Bay Dr Unit 203, Osprey, FL 34229

AVAILABLE ANNUAL OR 2026 SEASON. TURNKEY FURNISHED RENTAL! GATED, WATER VIEWS! WATERFRONT COMMUNITY IN OSPREY! 2 Bedroom 2 bath plus den. Den has French doors. Lots of light from this second-floor end unit condo. Front door has disappearing screen for fresh Air. TURNKEY FURNISHED. Completely renovated. NO CARPET. Porcelain tile thru out. Granite counters and high ceilings. Front loading washer &

Alba Lange WAGNER REALTY

293 Hidden Bay Dr Unit 203, Osprey, FL 34229
/2
$835,000 Sold May 21, 2025
- 2,214 Sq Ft
- $377/SF
- 42 Days On Market
- 3 Beds
- 3.5 Baths
- Built 2006
14021 Bellagio Way Unit 410, Osprey, FL 34229

Enjoy STUNNING sunsets 365 days a year in this LUXURIOUS WATERFRONT CONDO in Osprey, FL. From the moment you step out of your PRIVATE ELEVATOR and into this PENTHOUSE UNIT you’ll be amazed by the SPECTACULAR VIEWS overlooking Little Sarasota Bay and the Intracoastal Waterway (ICW). This 3 bed/3.5bath, TURNKEY FURNISHED unit, has been freshly painted inside and features newer flooring, crown

Adam Waxler UKEEPCOMMISSION REAL ESTATE

14021 Bellagio Way Unit 410, Osprey, FL 34229

/17
Est $325,774 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,244 Sq Ft
4247 Expedition Way Unit 103, Osprey, FL 34229

4247 Expedition Way Unit 103, Osprey, FL 34229

/66
$710,000 Open Sun 1PM - 4PM
- 3 Beds
- 2 Baths
- 1,937 Sq Ft
250 Hidden Bay Dr Unit A302, Osprey, FL 34229

WHAT A VIEW! Prepare to be captivated by jaw-dropping sunsets from your oversized, private, screened-in balcony, offering unobstructed vistas across Little Sarasota Bay to the peaceful barrier island of Casey Key. Welcome to Edgewater at Hidden Bay — a gated, 12-acre resort-style community perfectly positioned between the charm of historic Venice and the cultural vibrancy of downtown Sarasota.

Merryl Koven COLDWELL BANKER REALTY

250 Hidden Bay Dr Unit A302, Osprey, FL 34229
/66
$155,000 Sold May 15, 2025
- 736 Sq Ft
- $211/SF
- 4 Days On Market
- 1 Bed
- 1 Bath
- Built 1973
767 Pine Run Dr, Osprey, FL 34229

Welcome to 767 Pine Run Drive in sunny Osprey, FL—located between Sarasota and Venice so you can easily enjoy the beaches, shopping, arts and entertainment of both towns. This 736 square-foot home is all about easy living, featuring an open floor plan and soaring ceilings that let in tons of natural light. You’ll love the sun-drenched living and dining areas, with huge sliding doors that open to

Priscilla Adams COMPASS FLORIDA LLC

767 Pine Run Dr, Osprey, FL 34229

/39
Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,664 Sq Ft
169 Edgewood Dr, Osprey, FL 34229

169 Edgewood Dr, Osprey, FL 34229

/47
$725,000
- 3 Beds
- 3 Baths
- 2,484 Sq Ft
5100 Jessie Harbor Dr Unit 701, Osprey, FL 34229

Perched on the top floor of Blackburn Harbor Residences, this 3-bedroom, 3-bath end unit is just under 2500 square feet and offers stunning, unobstructed vistas of the intracoastal waterways and Gulf of Mexico. Located within a gated, amenity-rich community, this condo features an open floor plan with high ceilings, a spacious kitchen, and a living area that seamlessly blends indoor comfort with

Robert Ruiz WILLIAM RAVEIS REAL ESTATE

5100 Jessie Harbor Dr Unit 701, Osprey, FL 34229
/69
$265,000 Sold May 15, 2025
- 1,379 Sq Ft
- $192/SF
- 74 Days On Market
- 2 Beds
- 2 Baths
- Built 1973
360 Pine Run Dr Unit 360, Osprey, FL 34229

Welcome to 360 Pine Run Drive, a stunning residence nestled in the heart of Osprey, FL. This beautifully updated 2-bedroom, 2-bathroom condo spans 1,379 square feet and is the largest of its kind in the community. Designed by the renowned architect Frank Folsom Smith, this home is a masterpiece of the Sarasota School of Architecture, offering a seamless blend of style and functionality.As you

Priscilla Adams COMPASS FLORIDA LLC

360 Pine Run Dr Unit 360, Osprey, FL 34229

/27
Est $381,850 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,581 Sq Ft
4260 Expedition Way Unit 4260, Osprey, FL 34229

4260 Expedition Way Unit 4260, 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
/2
$520,000 Sold May 14, 2025
- 1,700 Sq Ft
- $306/SF
- 7 Days On Market
- 3 Beds
- 2 Baths
- Built 2001
544 Meadow Sweet Cir, Osprey, FL 34229

Welcome to this charming 3-bedroom, 2-bathroom, maintenance-free single-family home in Osprey, Florida!Located in the unique Cottages of Rivendell Community, this neighborhood offers a warm and welcomingenvironment where neighbors become friends from day one. Under the mature trees, you can walk in the shadeeven the warmest day of the year.As you step through the beautiful double doors, you'll be

Zita Bowers MICHAEL SAUNDERS & COMPANY

544 Meadow Sweet Cir, Osprey, FL 34229

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