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
/2
$842,190 Sold Dec 04, 2024
- 2,203 Sq Ft
- $382/SF
- 48 Days On Market
- 3 Beds
- 3 Baths
- Built 2000
385 N Point Rd Unit 403, Osprey, FL 34229

**STUNNINGLY UPDATED CONDO with MARVELOUS VIEW** This Spacious unit of over 2200sf features 3-Beds & 3-Baths, Open Floorplan plus Separate Dining Room (or possible Den/Flex area) 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 BEAUTIFULLY RENOVATED interior

Mark Lyda GENEROUS PROPERTY

385 N Point Rd Unit 403, Osprey, FL 34229

/69
Est $685,536 Not Listed For Sale
- 4 Beds
- 2 Baths
- 2,144 Sq Ft
521 Bayshore Dr, Osprey, FL 34229

521 Bayshore Dr, Osprey, FL 34229

/39
$725,000
- 3 Beds
- 2 Baths
- 1,994 Sq Ft
1212 Windward Dr, Osprey, FL 34229

Peace of Mind & Prime Location! Nestled in the sought-after Southbay Yacht & Racquet Club—a premier waterfront community with its own 170-slip marina on the Intracoastal—this high-elevation home (18+ ft, Flood Zone X – no flood insurance required!) offers exceptional value and lifestyle. Impact-Rated Windows, New Roof (2023), and $10,000 Paint Credit Included! Priced Below Recent $780K Appraisal

Mark Lyda GENEROUS PROPERTY

1212 Windward Dr, Osprey, FL 34229
/2
$759,000 Sold Dec 03, 2024
- 2,328 Sq Ft
- $326/SF
- 15 Days On Market
- 4 Beds
- 3 Baths
- Built 2005
513 Habitat Blvd, Osprey, FL 34229

Nestled within the charming landscape community of Willowbend, this exquisite four-bedroom, three-bath home designed by Lee Wetherington Homes is a true work of art. Ideally positioned on a corner lot with abundance of landscaping this Ashley floor plan has a stunning paver-trimmed drive and walkway that leads to a stunning residence. Step inside to discover a home filled with light, luxurious

Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

513 Habitat Blvd, Osprey, FL 34229

/96
Est $1,665,878 Not Listed For Sale
- 4 Beds
- 4.5 Baths
- 3,857 Sq Ft
627 N MacEwen Dr, Osprey, FL 34229

627 N MacEwen Dr, Osprey, FL 34229

/57
$289,000 Open Sat 1PM - 3PM
- 2 Beds
- 2 Baths
- 1,729 Sq Ft
304 Pine Run Dr, Osprey, FL 34229

HUGE PRICE REDUCTION " LOWEST Price In The Community - Your Opportunity To Add Your Personal Touch! Charming Coastal Retreat in the Heart of Osprey Welcome to 304 Pine Run Dr., a beautifully architecturally designed property nestled in the sought-after Pine Run community in Osprey, FL. Surrounded by lush tropical landscaping and just minutes from the Gulf Coast’s pristine beaches, this residence

Derek Edwards KELLER WILLIAMS ON THE WATER S

304 Pine Run Dr, Osprey, FL 34229
/2
$98,000 Sold Nov 28, 2024
- 104 Days On Market
570 Blackburn Point Rd Unit Siesta 40, Osprey, FL 34229

Desirable inside storage first floor boat rack. Take the stress out of boating and eliminate the boat ramps. This first class facility offers Full service amenities including deli, ice, drinks, bait, work racks, water, electric, fillet tables, pump out, detailing services and a host of other on site amenities. The building is fully enclosed and is hurricane rated. Unlimited in/out service that

David Babel BRIGHT REALTY

570 Blackburn Point Rd Unit Siesta 40, Osprey, FL 34229

/3
Est $237,561 Not Listed For Sale
- 2 Beds
- 2 Baths
- 858 Sq Ft
110 Oak St, Osprey, FL 34229

110 Oak St, Osprey, FL 34229

/100
$6,950,000
- 4 Beds
- 5.5 Baths
- 5,397 Sq Ft
144 N Casey Key Rd, Osprey, FL 34229

Priced reduced! Welcome to this extraordinary waterfront estate on exclusive Casey Key, showcasing panoramic views of Little Sarasota Bay and vistas of the Gulf of Mexico. Built to the latest hurricane standards with impact-rated windows and doors, this home is a true fortress of safety and resilience. Designed for both comfort and sophistication, this 4-bedroom, 5.5-bathroom estate spans over

Mark Coppens EXP REALTY LLC

144 N Casey Key Rd, Osprey, FL 34229
/2
$1,225,000 Sold Nov 27, 2024
- 2,680 Sq Ft
- $457/SF
- 101 Days On Market
- 3 Beds
- 3 Baths
- Built 2006
3621 N Point Rd Unit 601, Osprey, FL 34229

Located on the south end of building V in Meridian at The Oaks Preserve, this 3 bedroom, 3 bath residence is an incredible find. Enter through the secure lobby, go up the private elevator and step through the double doors and you will see how special this unit is. The first thing you will notice is the rich expanse of the hand rubbed walnut flooring. Meticulously maintained and offered turnkey

Steve Abbe COLDWELL BANKER REALTY

3621 N Point Rd Unit 601, Osprey, FL 34229

/11
Est $832,340 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,591 Sq Ft
226 Saint James Park, Osprey, FL 34229

226 Saint James Park, Osprey, FL 34229

/42
$695,000
- 3 Beds
- 3 Baths
- 2,590 Sq Ft
455 Park Trace Blvd, Osprey, FL 34229

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 situated between Oscar Scherer

Kim Azar-Calka MICHAEL SAUNDERS & COMPANY

455 Park Trace Blvd, Osprey, FL 34229
/58
$9,350,000 Sold Nov 27, 2024
- 6,997 Sq Ft
- $1336/SF
- 291 Days On Market
- 6 Beds
- 7.5 Baths
- Built 1992
1544 N Casey Key Rd, Osprey, FL 34229

Along the beaches of Casey Key, a private gated road leads to the exclusive northern end of this coveted barrier island. Sited on nearly 2.5 acres and 150 feet of private beach front, lies a spectacular estate home that has been shared and enjoyed by one family for generations. Designed by renowned architect Timothy Siebert, the property was thoughtfully planned as a gathering place. Wrapped

Valerie Dall'acqua PREMIER SOTHEBY'S INTERNATIONAL REALTY

1544 N Casey Key Rd, Osprey, FL 34229

/69
Est $290,936 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,223 Sq Ft
128 Woodland Dr, Osprey, FL 34229

128 Woodland Dr, Osprey, FL 34229

/68
$2,150,000
- 3 Beds
- 3 Baths
- 4,191 Sq Ft
85 Sugar Mill Dr, Osprey, FL 34229

**STUNNINGLY DESIGNED and UPDATED -- ARCHITECTURAL ESTATE in the coveted OAKS BAYSIDE Country Club Neighborhood** on Little Sarasota Bay waters features 3 BEDS plus DEN/OFFICE, 3 FULL BATHS and incredible detail throughout including beautiful crown moldings, volume ceilings, hardwood floors, wainscoting, plantation shutters, LED lighting accents and MORE! NEW ROOF (2020). The CHEF’s KITCHEN

Mark Lyda GENEROUS PROPERTY

85 Sugar Mill Dr, Osprey, FL 34229
/2
$535,000 Sold Nov 25, 2024
- 2,778 Sq Ft
- $193/SF
- 577 Days On Market
- 3 Beds
- 3 Baths
- Built 2000
385 N Point Rd Unit 304, Osprey, FL 34229

One or more photo(s) has been virtually staged. Don’t pass up the opportunity to live the country club lifestyle in comfort and ease in this well-priced unit, with lots of living space, in Meridian at The Oaks Preserve. Spacious, bright and clean, with lovely wood floors, this property is waiting for you to make it your own. With a master bedroom suite, a 2nd junior suite, a third bedroom, a den

Steve Abbe COLDWELL BANKER REALTY

385 N Point Rd Unit 304, Osprey, FL 34229

/56
Est $2,304,621 Not Listed For Sale
- 5 Beds
- 6 Baths
- 4,998 Sq Ft
680 N MacEwen Dr, Osprey, FL 34229

680 N MacEwen Dr, Osprey, FL 34229

/54
$824,000 Open Sat 1PM - 3PM
- 4 Beds
- 3 Baths
- 3,091 Sq Ft
790 Shadow Bay Way, Osprey, FL 34229

Brand New Tile Roof March 2025. Experience the ultimate in serene living within the picturesque Woodlands of Rivendell, where this stunning residence seamlessly combines the beauty of nature with modern comforts. Bordered by a preserve at the rear and flanked by mature trees across the street, it offers the perfect sanctuary for those seeking tranquility amidst lush greenery. The curb appeal is

Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

790 Shadow Bay Way, Osprey, FL 34229
/2
$450,000 Sold Nov 21, 2024
- 2,222 Sq Ft
- $203/SF
- 47 Days On Market
- 3 Beds
- 2 Baths
- Built 1994
619 Pine Ranch Rd E, Osprey, FL 34229

As you can see from the photos, this is a wonderful property in an ideal location -- it really is a beautiful neighborhood! As you can also see from the photos, it presents as spacious, clean, and fresh given the fact that it has the original kitchen, baths, and floors from 1994, and the pool will likely need resurfacing. Brand new tile roof, 8/15/2018! As the new owner will likely remodel the

John Michailidis KELLER WILLIAMS ISLAND LIFE REAL ESTATE

619 Pine Ranch Rd E, Osprey, FL 34229

/24
Est $849,665 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,448 Sq Ft
130 N Creek Ln, Osprey, FL 34229

130 N Creek Ln, Osprey, FL 34229

/44
$910,000
- 3 Beds
- 2 Baths
- 2,271 Sq Ft
293 Turquoise Ln, Osprey, FL 34229

**STUNNING, UPDATED, MAINTENANCE-FREE Home is located in EMERALD WOODS, behind the Secure Gates of the Distinguished OAKS PRESERVE Neighborhood. Offering 3-Beds (or 2-Beds plus Den), 2-Baths and 2-Car Garage, Premium finishes abound throughout this home and include a Chef’s Kitchen, Tray Ceilings, Crown Moldings, Beautiful Luxury Vinyl Wood Plank, Plantation Shutters, an Oversized, Owner’s

Mark Lyda GENEROUS PROPERTY

293 Turquoise Ln, Osprey, FL 34229
/2
$845,000 Sold Nov 21, 2024
- 2,408 Sq Ft
- $351/SF
- 61 Days On Market
- 4 Beds
- 3 Baths
- Built 2004
1031 Scherer Way, Osprey, FL 34229

The furnishing are available for purchase (with some exceptions) with a separate contract.This completely renovated 4 bed/3 bath home offers one level luxury living in the beautiful Rivendell community! (a full list of improvements that includes new roof and new HVAC is available). This is a uniquely private location with the preserve behind you, and mature trees on either side with a

Steven Weiss REDFIN CORPORATION

1031 Scherer Way, Osprey, FL 34229

/65
Est $583,004 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,188 Sq Ft
599 Pine Ranch East Rd, Osprey, FL 34229

599 Pine Ranch East Rd, Osprey, FL 34229

/64
$724,900
- 4 Beds
- 3 Baths
- 2,298 Sq Ft
644 Rivendell Blvd, Osprey, FL 34229

Optional Turnkey! Built in 2001, this home features high tray ceilings and a smart, functional layout.The formal living and family rooms, along with the en-suite primary bedroom, open to the lanai. The dining room includes custom built-ins, while two guest bedrooms share a hall bathroom. A private in-law suite, currently used as an office, has its own bathroom and lanai access.The kitchen, with

Veronica Manes MICHAEL SAUNDERS & COMPANY

644 Rivendell Blvd, Osprey, FL 34229
/2
$750,000 Sold Nov 20, 2024
- 1,950 Sq Ft
- $385/SF
- 153 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2019
260 Hidden Bay Dr Unit B-504, Osprey, FL 34229

PENTHOUSE PARADISE WITH GORGEOUS SUNSET WATER VIEWS!3/2.5 Condo including storage room and garage parking.Welcome to Edgewater at HIDDEN BAY, where LUXURY meets flexibility! This spacious modern 2019 PENTHOUSE condominium has been masterfully designed with Category 5 hurricane resilience and boasts a beautifully converted FLEX room that now serves as a spacious third bedroom complete

Diane Wacha LPT REALTY, LLC

260 Hidden Bay Dr Unit B-504, Osprey, FL 34229

/44
Est $1,147,203 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,534 Sq Ft
315 Sea Anchor Dr, Osprey, FL 34229

315 Sea Anchor Dr, Osprey, FL 34229

/46
$749,000
- 4 Beds
- 3 Baths
- 2,320 Sq Ft
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
/2
$850,000 Sold Nov 19, 2024
- 2,933 Sq Ft
- $290/SF
- 33 Days On Market
- 4 Beds
- 3 Baths
- Built 2004
995 Scherer Way, Osprey, FL 34229

Walk to Pine View School from this magnificent spacious home! 4 bedrooms, 3 baths and an office. The large living areas are further enhanced with custom multi-tiered tray ceilings. Open, airy, light and bright, 3 sets of sliding glass doors lead from all the main living areas to the welcoming pool and spa on the lanai. Even when you're not lounging on the lanai or in the pool or spa, the 21

Ellen Ross BRIGHT REALTY

995 Scherer Way, Osprey, FL 34229

/27
Est $431,938 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,724 Sq Ft
1811 Highland Rd, Osprey, FL 34229

1811 Highland Rd, Osprey, FL 34229

/51
$625,000
- 3 Beds
- 2 Baths
- 2,559 Sq Ft
566 Oak Bay Dr, Osprey, FL 34229

Welcome to Bay Oaks Estates. This 3-bedroom 2 bath plus den is a classic Florida home featuring a pool with mosaic inspired ocean theme. And with no one behind you and no houses in front offers plenty of privacy. Oh, I almost forgot this home offers a wood burning fire place for those couple of cold nights a year, lol. New roof September 2022 newer water heater. This secluded community is only

Greg Walters SARABAY REAL ESTATE INC

566 Oak Bay Dr, Osprey, FL 34229
/2
$975,000 Sold Nov 15, 2024
- 2,411 Sq Ft
- $404/SF
- 3 Beds
- 2 Baths
- Built 1991
206 Four Knot Ln, Osprey, FL 34229

3-br, 2-bath, 2-car garage with heated enclosed pool located in Southbay Yacht and Racquet Club. Beautifully landscaped, irrigation, from court yard, fire pit patio.

Stellar Non-Member Agent Stellar Non-Member Office

206 Four Knot Ln, Osprey, FL 34229

/46
Est $1,624,568 Not Listed For Sale
- 3 Beds
- 3 Baths
- 3,740 Sq Ft
345 S Shore Dr, Osprey, FL 34229

345 S Shore Dr, Osprey, FL 34229

/75
$1,649,000
- 4 Beds
- 4 Baths
- 4,001 Sq Ft
75 Osprey Point Dr, Osprey, FL 34229

Welcome to 75 Osprey Point, a residence that epitomizes timeless elegance and thoughtful design within the prestigious Oaks Bayside. On two expansive lots totaling over three-quarters of an acre, this architectural estate was originally designed by renowned architect Bo MacEwen, the visionary behind The Oaks iconic clubhouse. A harmonious blend of traditional sophistication and modern updates

Joel Schemmel PREMIER SOTHEBY'S INTERNATIONAL REALTY

75 Osprey Point Dr, Osprey, FL 34229
/2
$770,000 Sold Nov 15, 2024
- 2,153 Sq Ft
- $358/SF
- 134 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2002
463 Park Trace Blvd, Osprey, FL 34229

Welcome to your dream home in Osprey and Park Trace Estates, one of South Sarasota's most intimate and picturesque custom home communities. This stunning 3-bedroom, 2 and 1/2-bathroom pool home has a Brand New Roof with a 15 year transferrable warranty and a Brand New Hot Water Heater! It features an open floor plan on an oversized lot with a breathtaking lake view. As you step inside, high

Tina Renta KELLER WILLIAMS ISLAND LIFE REAL ESTATE

463 Park Trace Blvd, Osprey, FL 34229

/32
Est $357,818 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,397 Sq Ft
112 Villa Dr, Osprey, FL 34229

112 Villa Dr, Osprey, FL 34229

/61
$247,400 Open Sat 11AM - 1PM
- 2 Beds
- 2 Baths
- 1,223 Sq Ft
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
/2
$770,000 Sold Nov 14, 2024
- 1,943 Sq Ft
- $396/SF
- 401 Days On Market
- 3 Beds
- 2 Baths
- Built 2001
232 Hidden Bay Dr Unit 602, Osprey, FL 34229

Live on the TOP FLOOR & ENJOY UNBELIEVABLE WATER & SUNSET VIEWS ALL YEAR round with an air-conditioned sunroom overlooking the water. IMPACT WINDOWS/DOORS for peace of mind. Seller relocation is your lucky day with this PRICE IMPROVED, partially furnished penthouse condo.A 3 Bedroom, 2 Bath Baypoint Vista Condo just under 2000 sqft. The sprawling open floor plan showcases a

Kelly Pankiw ENGEL & VOELKERS VENICE DOWNTOWN

232 Hidden Bay Dr Unit 602, Osprey, FL 34229

/60
Est $484,226 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,229 Sq Ft
455 N Shore Dr, Osprey, FL 34229

455 N Shore Dr, Osprey, FL 34229

/62
$449,900
- 2 Beds
- 2 Baths
- 1,400 Sq Ft
2251 Jessie Harbor Dr, Osprey, FL 34229

**1ST FLOOR END UNIT CONDO with WATER VIEW and PRIVATE 1-CAR GARAGE, WEST OF TRAIL! BRING YOUR BOAT & KAYAK for DIRECT ACCESS TO INTRACOASTAL WATERWAY and GULF OF MEXICO (No Bridges)** Featuring 2 BEDS and 2 FULL BATHS, this LIGHT AND BRIGHT, 1ST FLOOR END UNIT dwelling features an Impressive Kitchen with Granite counters, Stainless Steel appliances and solid wood cabinets while the Spacious

Mark Lyda GENEROUS PROPERTY

2251 Jessie Harbor Dr, Osprey, FL 34229

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