Osprey, FL Homes

/46
$1,049,000
- 4 Beds
- 3 Baths
- 2,775 Sq Ft
366 S Creek Ct, Osprey, FL 34229

Welcome home to the highly sought after gated waterfront community of South Creek in Osprey FL! This gorgeous home has a nearly COMPLETELY RENOVATED interior with an open and bright kitchen, separate living and dining spaces, and dinette off the kitchen and family room. The home features 4 bedrooms, 3 bathrooms, and a heated pool/spa with covered lanai. There are luxury touches everywhere

EJ Stukenborg KELLER WILLIAMS ON THE WATER S

366 S Creek Ct, Osprey, FL 34229
/31
$2,500 per month
- 3 Beds
- 2.5 Baths
- 1,950 Sq Ft
- Condo for Rent
260 Hidden Bay Dr Unit B-202, Osprey, FL 34229

Edgewater at Hidden Bay Annual Rental available now. UNFURNISHED. This pristine 3-bedroom (no extra den), 2.5-bath condo features a spacious lanai, offering a glimpse of the bay over the serene preserve views—perfect for enjoying breathtaking sunsets. King murphy bed in 2nd guest room, living room wall unit and patio furniture are included. Additional details that make this unit feel more like a

Terri Lindsay LINDSAY LEASING LLC

260 Hidden Bay Dr Unit B-202, Osprey, FL 34229
/2
$390,000 Sold Apr 15, 2025
- 1,334 Sq Ft
- $292/SF
- 21 Days On Market
- 2 Beds
- 2 Baths
- Built 1970
441 N Shore Dr, Osprey, FL 34229

Bring your BOAT or RV and store ON YOUR LOT. West of the Trail! Welcome home to Sorrento Shores, nestled perfectly between the vibrant communities of Sarasota and Venice, yet tucked away from the hustle and bustle of city life in the charming town of Osprey. This sought-after neighborhood offers spacious lots, a relaxed atmosphere, and the added bonus of low HOA fees and no CDD to worry

Dawn Barnett EXIT KING REALTY

441 N Shore Dr, Osprey, FL 34229

/34
Not Listed For Sale
- 2 Beds
- 2 Baths
- 959 Sq Ft
201 Palm Air Dr, Osprey, FL 34229

201 Palm Air Dr, Osprey, FL 34229

/43
$997,000
- 3 Beds
- 3 Baths
- 2,344 Sq Ft
3904 Waypoint Ave, Osprey, FL 34229

This stunning Taylor Morrison Lazio floor plan residence offers an exceptional blend of luxury and tranquility in a desirable West of Trail gated bayfront community. With breathtaking views of the sparkling lake and direct access to the bay, residents can enjoy picturesque sunsets and serenity of daily wildlife sightings. Newer sparkling pool and spa surrounded in pavers. The home features a

Tamara Currey PREMIER SOTHEBYS INTL REALTY

3904 Waypoint Ave, Osprey, FL 34229
/11
$2,200 per month
- 2 Beds
- 2 Baths
- 1,135 Sq Ft
- Condo for Rent
4223 Frontier Ln, Osprey, FL 34229

This 1,135-square-foot condo features 2 bedrooms, 2 bathrooms, and a 1-car garage and will be available for an annual lease starting June 1, 2025. First and last month’s rent, along with a security deposit (3x $2,200), are required before move-in. A credit and background check is required, with a $50 application fee per person. Rent includes water, sewer, trash, access to amenities and exterior

Anna Bridinger PELICAN REALTY CORP

4223 Frontier Ln, Osprey, FL 34229
/2
$1,160,000 Sold Apr 15, 2025
- 1,787 Sq Ft
- $649/SF
- 10 Days On Market
- 3 Beds
- 2 Baths
- Built 1978
131 Tina Island Dr, Osprey, FL 34229

Welcome to your dream waterfront oasis! This exquisite 3-bedroom, 2-bathroom residence offers unparalleled water views and mesmerizing sunsets from the expansive pool deck. The generous outdoor living area is perfect for hosting gatherings or enjoying peaceful moments by the canal. The thoughtfully designed split-bedroom layout ensures privacy, making it ideal for accommodating guests or family

Sarah McGuire WHITE SANDS REALTY GROUP FL

131 Tina Island Dr, Osprey, FL 34229

/46
Est $594,147 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,004 Sq Ft
2007 Cordes St, Osprey, FL 34229

2007 Cordes St, Osprey, FL 34229

/62
$660,000
- 3 Beds
- 3 Baths
- 2,055 Sq Ft
385 N Point Rd Unit 402, Osprey, FL 34229

**BEAUTIFULLY UPDATED CONDO with MARVELOUS VIEW** features 3-BEDS and 3-FULL BATH, 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 Impressively Renovated interior which boasts Engineered Hardwood and designer Wood Plank Tile flooring, Plantation

Mark Lyda GENEROUS PROPERTY

385 N Point Rd Unit 402, Osprey, FL 34229
/20
$3,099 per month
- 3 Beds
- 3.5 Baths
- 2,416 Sq Ft
- House for Rent
591 Oak Bay Dr, Osprey, FL 34229

Mint-condition, immaculate pool home nestled within an exclusive Osprey, FL community. This pristine 3-bedroom, 3.5-bath residence boasts over 2,400 sq. ft. of elegant living space, offering a perfect blend of style and comfort. Step into a spacious layout featuring a gourmet kitchen, expansive family room, and formal living and dining areas. Each bedroom is a private suite, ensuring ultimate

John Michailidis REAL PROPERTY MANAGEMENT

591 Oak Bay Dr, Osprey, FL 34229
/2
$700,000 Sold Apr 15, 2025
- 2,504 Sq Ft
- $280/SF
- 69 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2004
521 Luminary Blvd, Osprey, FL 34229

This stunning Lee Wetherington home, in the prestigious Willowbend community of Osprey, showcases the natural beauty of Florida through its beautifully designed Stanford, rarely available floor plan. Home has a 22-kilowatt whole-house generator. Set against the backdrop of a sparkling lake, the residence features a great room, dining area, kitchen, dinette, owner’s suite all benefiting from one

Tamara Currey PREMIER SOTHEBYS INTL REALTY

521 Luminary Blvd, 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

/49
$1,285,000
- 4 Beds
- 3.5 Baths
- 3,160 Sq Ft
135 N Creek Ln, Osprey, FL 34229

Experience the ideal blend of tranquility and convenience in this exquisite residence, designed by renowned builder Robert Guengerich as his sanctuary. Set at the end of a serene cul-de-sac and surrounded by mature oak trees, this remarkable home offers a peaceful retreat while remaining close to everything you may need. Upon entry, you'll be captivated by the grand 13-foot ceilings, elegant

carlos santos PREMIER SOTHEBYS INTL REALTY

135 N Creek Ln, Osprey, FL 34229
/20
$1,695 per month
- 1 Bed
- 1 Bath
- 595 Sq Ft
- Condo for Rent
51 MacEwen Dr Unit 14, Osprey, FL 34229

Windsor Lodge in The Oaks - Gorgeous turnkey furnished studio apartment available now for lease! This charming 595 sq ft second-floor studio is located in the desirable Windsor Lodge within the exclusive Oaks community. It features top-of-the-line finishes, all brand new, and is accessible by both elevator and stairs. The unit includes a full kitchen equipped with a full-size refrigerator,

Terri Lindsay LINDSAY LEASING LLC

51 MacEwen Dr Unit 14, Osprey, FL 34229
/2
$879,352 Sold Apr 15, 2025
- 1,937 Sq Ft
- $454/SF
- 14 Days On Market
- 3 Beds
- 2 Baths
- Built 2024
280 Hidden Bay Dr Unit 402, Osprey, FL 34229

One or more photo(s) has been virtually staged. Under Construction. Photos are a representation of multiple floor plans in the building. Watch the most breathtaking sunsets from your private extra-large, screened-in balcony as you look out across the bay to the barrier island of Casey Key! Centrally located between historic Venice and vibrant downtown Sarasota is Edgewater at Hidden Bay. This

Thomas Netzel PREMIER SOTHEBYS INTL REALTY

280 Hidden Bay Dr Unit 402, Osprey, FL 34229

/2
Est $359,471 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

/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
/21
$2,100 per month
- 2 Beds
- 2 Baths
- 1,135 Sq Ft
- Condo for Rent
116 Revolution Way Unit 116, Osprey, FL 34229

ONE MONTH FREE RENT with a 24-MONTH LEASE - Ask about our security deposit alternative to help with the upfront move in cost! You are just going to love this stunning, 2-bedroom, 2-bathroom condo located in Osprey! Located in the gated community of Bay Street, it iclose to Sarasota's top-rated, and nationally recognized, Pine View School. This second floor unit is situated on a quiet cul-de-sac,

Christopher Plemenos

116 Revolution Way Unit 116, Osprey, FL 34229
/2
$832,000 Sold Apr 14, 2025
- 1,988 Sq Ft
- $419/SF
- 178 Days On Market
- 3 Beds
- 2 Baths
- Built 2006
14041 Bellagio Way Unit 313, Osprey, FL 34229

Welcome to the highly desirable community of The Villas at Osprey Harbor! This light and bright end unit with a private entrance is loaded with recent, tasteful updates including a fully renovated kitchen in 2022 with high end rift cut white oak custom cabinetry and a quartz breakfast bar, induction stove, updated baths, 24-by-24 porcelain tile, lighting, fans, fresh paint throughout, a coffee

Megan George PREMIER SOTHEBYS INTL REALTY

14041 Bellagio Way Unit 313, Osprey, FL 34229

/24
Est $352,313 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
$1,199,000 Open Sun 1PM - 3PM
- 4 Beds
- 3 Baths
- 2,925 Sq Ft
120 Lookout Point Dr, Osprey, FL 34229

Spacious Custom built home featuring an oversized corner yard, High Ceilings, Updated Kitchen and Bathrooms, Family Room with Wood Burning Fireplace, 3 Bedrooms, 3 Full Baths and a Bonus Room/ 4th Bedroom upstairs. Entertain in the Large Lanai with Outdoor Kitchen overlooking the Pool and wide Greenbelt view. The Stylish and Durable new Metal Roof will protect you for years to come, full

Sharon Lewis GOLF & BAY PROPERTIES LLC

120 Lookout Point 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
/2
$275,000 Sold Apr 11, 2025
- 900 Sq Ft
- $306/SF
- 33 Days On Market
- 3 Beds
- 2 Baths
- Built 1963
208 Pennsylvania Ave, Osprey, FL 34229

PRICED to SELL! Incredible Opportunity, Don\'t miss this one! Nice 3Br 2Ba single family home on large fenced corner lot in Osprey, Florida near Venice Beach. NO HOA! Large lot with plenty of space for additions, RV or Boat parking, swimming pool, etc. One of the best deals in the area! Turn-key and ready to move in, New paint

Stephen Hachey FLAT FEE MLS REALTY

208 Pennsylvania Ave, Osprey, FL 34229

/4
Est $55,862 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

/62
$599,000
- 3 Beds
- 3 Baths
- 2,000 Sq Ft
232 Hidden Bay Dr Unit 504, Osprey, FL 34229

Price drastically reduced!Located in the Hidden Bay community in Osprey with views of Little Sarasota Bay and the Intracoastal Waterway, this stunning corner unit comes with a private 2-car garage!The unit offers 2000 sq ft of living area with 3 full bedroom suites with en-suite bathrooms for privacy and convenience. The spacious balcony has both screens and sliding doors to the outside and

Helena Nordstrom PREMIER SOTHEBYS INTL REALTY

232 Hidden Bay Dr Unit 504, Osprey, FL 34229
/30
$2,200 per month
- 1 Bed
- 1 Bath
- 623 Sq Ft
- Condo for Rent
51 MacEwen Dr Unit 12, Osprey, FL 34229

For Lease at THE OAKS CLUB WINDSOR LODGE. Private sanctuary rarely available for rent at one of Sarasota's most exclusive private country clubs. This lovely sunny Second floor end unit is fully turnkey furnished and ready for MOVE IN. Completely updated one bedroom, resort suite style studio, condominium with sweeping Water Views of the Lakefront of the 18th fairway on the Eagle Course. A

Patrice Ivan WAGNER REALTY

51 MacEwen Dr Unit 12, Osprey, FL 34229
/2
$832,750 Sold Apr 10, 2025
- 1,937 Sq Ft
- $430/SF
- 27 Days On Market
- 3 Beds
- 2 Baths
- Built 2025
280 Hidden Bay Dr Unit 303, Osprey, FL 34229

One or more photo(s) has been virtually staged. Under Construction. Photos are for demonstration purposes only and may not reflect the actual unit or floor plan. Witness the most breathtaking sunsets from your private, extra-large screened-in balcony as you gaze out across the bay to the barrier island of Casey Key! Centrally between historic Venice and vibrant downtown Sarasota is Edgewater at

Thomas Netzel PREMIER SOTHEBYS INTL REALTY

280 Hidden Bay Dr Unit 303, Osprey, FL 34229

/12
Est $25,168 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

/57
$569,000
- 2 Beds
- 2 Baths
- 1,574 Sq Ft
784 Sarabay Rd, Osprey, FL 34229

Welcome to Your Waterfront Villa in Osprey, Florida!Discover the ultimate seasonal retreat in this beautifully updated 2-bedroom, 2-bathroom single-story villa, designed for stress-free living. Nestled in a private 25-unit secluded community, this waterfront gem offers not only stunning views but also a lifestyle of unparalleled ease and simplicity.Key Features:Move in ready: Move in with ease

Peggy Lewis COLDWELL BANKER SARASOTA CENT.

784 Sarabay Rd, Osprey, FL 34229
/16
$2,200 per month
- 3 Beds
- 2 Baths
- 1,412 Sq Ft
- House for Rent
221 Glenwood Ave, Osprey, FL 34229

Looking for your dream home? Through our seamless leasing process, this beautifully designed home is move-in ready. Our spacious layout is perfect for comfortable living that you can enjoy with your pets too; we’re proud to be pet friendly. Our homes are built using high-quality, eco-friendly materials with neutral paint colors, updated fixtures, and energy-efficient appliances. Enjoy the

Nico Silva Vanegas MAIN STREET RENEWAL LLC

221 Glenwood Ave, Osprey, FL 34229
/2
$925,000 Sold Apr 10, 2025
- 2,166 Sq Ft
- $427/SF
- 31 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2024
280 Hidden Bay Dr Unit 401, Osprey, FL 34229

One or more photo(s) has been virtually staged. Under Construction. Under construction. The photos are a representation of multiple floor plans in the building. Centrally located between historic Venice and vibrant downtown Sarasota is Edgewater at Hidden Bay. The gated, 12-acre resort-style community is nestled on the water’s edge of Little Sarasota Bay in Osprey. The final waterfront building

Thomas Netzel PREMIER SOTHEBYS INTL REALTY

280 Hidden Bay Dr Unit 401, Osprey, FL 34229

/50
Est $522,318 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,004 Sq Ft
2006 Preymore St, Osprey, FL 34229

2006 Preymore St, Osprey, FL 34229

/69
$685,000
- 3 Beds
- 3 Baths
- 2,100 Sq Ft
236 Hidden Bay Dr Unit 301, Osprey, FL 34229

This beautiful 3 bed, 3 full ensuite baths and a 3 car garage home in the heart of Osprey in the desirable waterfront gated Hidden Bay Community. Come home to your own hidden gem and enjoy SPECTACULAR unobstructed views of Sarasota’s Intracoastal Waterway, also known as Little Sarasota Bay, and preserve. Complete with updated PGT WINGUARD IMPACT WINDOWS AND DOORS installed in 2018. This home is

Linda Scheller COLDWELL BANKER REALTY

236 Hidden Bay Dr Unit 301, Osprey, FL 34229
/63
$7,000 per month
- 3 Beds
- 2 Baths
- 1,737 Sq Ft
- House for Rent
543 Pine Ranch Rd E, Osprey, FL 34229

An Ascendia Property! **Available beginning January 15, 2025, for a 90-night minimum stay or longer. The rental rate in the listing does not include additional fees and taxes. The rental rate will be discounted for a long-term lease (6-12 months). Please note, a long-term lease of 6-12 months DOES NOT include utilities such as electric, water, sewer or internet.** This 3-bedroom, 2-bathroom

Beth Dilley ASCENDIA REAL ESTATE

543 Pine Ranch Rd E, Osprey, FL 34229
/2
$400,000 Sold Apr 08, 2025
- 1,574 Sq Ft
- $254/SF
- 115 Days On Market
- 2 Beds
- 2 Baths
- Built 2016
4239 Expedition Way, Osprey, FL 34229

NEW PRICE AND PRICED TO SELL - THE ONLY AVAILABLE 2 CAR GARAGE UNIT LISTED IN THE COMMUNITY! Welcome to Bay Street Village, a highly sought-after gated condominium community in the heart of Osprey. This rarely available FIRST FLOOR, EXTENDED 2-car garage condo offers plenty of space for vehicles and gear, making it ideal for those with an active lifestyle. The beautiful home is being sold

Joe Cleary RE/MAX ALLIANCE GROUP

4239 Expedition Way, Osprey, FL 34229

/17
Est $356,351 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

/48
$685,000
- 3 Beds
- 3 Baths
- 2,055 Sq Ft
409 N Point Rd Unit 502, Osprey, FL 34229

**GORGEOUS VIEW from this Move-In Ready, 5TH FLOOR, 3-BED / 3-BATH, LUXURY CONDO!! The coveted lifestyle of The Oaks Country Club with the convenience and amenities of maintenance-free condominium living come together at this Gorgeous Meridian 5th floor residence. Upon exiting the elevator into the private foyer, step inside and enjoy the breathtaking panoramic preserve, bay and Gulf of Mexico

Mark Lyda GENEROUS PROPERTY

409 N Point Rd Unit 502, Osprey, FL 34229
/74
$8,000 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
$512,500 Sold Apr 07, 2025
- 2,147 Sq Ft
- $239/SF
- 34 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2005
1152 Beachcomber Ct Unit 15, Osprey, FL 34229

Coastal Living at its Finest! Discover this beautifully designed 3 bedroom, 2.5 bath townhouse in the desirable Blackburn Point Marina Community! Enjoy prime location just steps from the Intercoastal Waterway, the Gulf of Mexico, Blackburn State Park, the Blackburn Point Marina, and the beloved Casey Key Fish House and Tiki Bar along with the new Deep Lagoon Restaurant. Step inside to find a

Jennifer Bright BRIGHT REALTY

1152 Beachcomber Ct Unit 15, Osprey, FL 34229

/27
Est $414,462 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

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