Osprey, FL Homes

/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
/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
$559,500 Sold Apr 04, 2025
- 2,165 Sq Ft
- $258/SF
- 56 Days On Market
- 3 Beds
- 2 Baths
- Built 2004
1219 Chalet Ct, Osprey, FL 34229

This stunning Lee Wetherington-built home in Osprey's Willowbend community beautifully combines Florida's natural charm with elegant living. The desirable Willow floor plan borders a wide greenbelt with tasteful landscaping that enhances its curb appeal. The enlarged lanai offers a serene private space, just a short distance to the community's heated pool and spa. Inside, the home showcases

Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

1219 Chalet Ct, Osprey, FL 34229

/61
Est $420,665 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

/4
$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
/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
$1,051,025 Sold Apr 04, 2025
- 1,937 Sq Ft
- $543/SF
- 2 Days On Market
- 3 Beds
- 2 Baths
- Built 2024
280 Hidden Bay Dr Unit 502, Osprey, FL 34229

One or more photo(s) has been virtually staged. Under Construction. Penthouse-level unit with unparalleled panoramic water views of Sarasota Bay and the Gulf of Mexico. A condominium with a view like this is seldom offered for sale and the top floor equals top views! Watch the most breathtaking sunsets from your private, extra-large, screened-in balcony on the fifth and top floor of this

Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

280 Hidden Bay Dr Unit 502, Osprey, FL 34229

/59
Est $426,163 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

/83
$1,235,000 Pending
- 2 Beds
- 3 Baths
- 2,521 Sq Ft
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
/55
$2,400 per month
- 2 Beds
- 2 Baths
- 1,479 Sq Ft
- Condo for Rent
291 Hidden Bay Dr Unit 102, Osprey, FL 34229

This lease is available starting MAY 2025. This spacious first floor unit is fully furnished, with two bedrooms and two bathrooms. The view overlooks a tranquil pond. Hidden Bay condominium is a 12-acre, gated community on Sarasota Bay in Osprey with beautiful views of Casey Key.The community includes a clubhouse that features a fully-stocked library, an entertainment/media room, kitchen,

Anthony DeLuca AUDREY RAIN RENTALS, INC

291 Hidden Bay Dr Unit 102, Osprey, FL 34229
/2
$600,000 Sold Apr 03, 2025
- 1,975 Sq Ft
- $304/SF
- 86 Days On Market
- 4 Beds
- 2 Baths
- Built 1996
818 Oak Pond Dr, Osprey, FL 34229

This is your Dream Home! Upgrades galore and ready to move-in. 4 Bedrooms 2 baths with sparkling caged pool and stunning new paver brick deck (2022), oversize covered lanai, outdoor shower, in a very private setting. NEW ROOF in 2019, NEW AC in 2019, whole house RE-PLUMBED in 2021. Enjoy the exquisite Ivory tone PORCELAIN TILE FLOORS throughout most of the home. NEW GRANITE COUNTERS in kitchen

Jacqueline Middleton SUNSET REALTY

818 Oak Pond Dr, Osprey, FL 34229

/4
Est $30,404 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

/60
$3,750,000
- 4 Beds
- 4.5 Baths
- 4,781 Sq Ft
1042 N Casey Key Rd, Osprey, FL 34229

EXCEPTIONAL WATERFRONT RESIDENCE on the exclusive island of North Casey Key is a rare opportunity to own a piece of coastal Florida. Nestled in the sought-after Palmer neighborhood, this home has been lovingly maintained by the same discerning owners since 1999—a testament to the pride, care, and attention poured into every detail over the years. Set on an expansive 0.68-acre lot with 131 feet of

Brandy Sheldon COLDWELL BANKER REALTY

1042 N Casey Key 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 February 1, 2025 thru July 31, 2025*** 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
$237,000 Sold Mar 31, 2025
- Land
- 0.97 Acre
- $244,330 per Acre
- 34 Days On Market
14 Old Venice Rd, Osprey, FL 34229

Great opportunity to purchase a 1 acre parcel close to town with many possibilities. The property has been cleared of all structures and out buildings. The approximate 1 acre parcel is ready to build in the town of Osprey. Property is close to Pine View school and minutes to the beaches. The Legacy trail and Oscar Scherer State park are near by. Shopping, restaurants, and Medical offices are also

Glenn Davis COLDWELL BANKER SARASOTA CENT.

14 Old Venice Rd, 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

/40
$597,000 Open Sun 1PM - 3PM
- 3 Beds
- 3 Baths
- 2,082 Sq Ft
1313 Thornapple Dr, Osprey, FL 34229

Stunning finishes welcome you to this enchanting Lee Wetherington-built residence located in Willowbend. Incredibly light and bright home has been perfected by discerning sellers with unending attention to details. Notably: Crown molding, extensive trim molding, Plantation Shutters, Tray Ceilings, tile on diagonal and wood flooring. This Extended Cypress floor plan is the best use of space,

Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

1313 Thornapple Dr, 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
$885,000 Sold Mar 31, 2025
- 2,100 Sq Ft
- $421/SF
- 115 Days On Market
- 3 Beds
- 3 Baths
- Built 1997
236 Hidden Bay Dr Unit 504, Osprey, FL 34229

One or more photo(s) has been virtually staged. Waterfront resort-style living in a gated community with breathtaking panoramic views over Little Sarasota Bay. This fifth-level end unit, with elevator access, has been tastefully remodeled. It offers three bedrooms, three full en-suite baths, a screened/glassed-in lanai for entertaining, all while watching spectacular sunsets over the Intracoastal

Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

236 Hidden Bay Dr Unit 504, 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

/41
$669,000
- 4 Beds
- 2 Baths
- 2,135 Sq Ft
750 Anna Hope Ln, Osprey, FL 34229

Impeccable style and effortless grace define this Rivendell home, which stands as a testament to refined living. Nestled in the serene beauty of Osprey, this four-bedroom property is bathed in soft sunlight and encapsulates the tranquility of its surroundings. The architectural brilliance of this residence is evident as soon as you step inside, greeted by a sprawling great room that serves as the

Stephanie Church COLDWELL BANKER REALTY

750 Anna Hope Ln, 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
$324,000 Sold Mar 28, 2025
- 1,430 Sq Ft
- $227/SF
- 34 Days On Market
- 3 Beds
- 2 Baths
- Built 2017
76 Explorer Dr Unit 104, Osprey, FL 34229

Location Location Location! Welcome home to this beautifully upgraded 3-bedroom, 2-bath end unit, perfectly positioned in a sought-after, pet-friendly gated community. Built for peace of mind, this condo features sturdy block stucco construction and hurricane-impact windows and doors, ensuring both durability and security. Step inside and feel the spaciousness of the open-concept design,

Pan Steele, GRI COLDWELL BANKER REALTY

76 Explorer Dr Unit 104, Osprey, FL 34229

/13
Est $919,667 Not Listed For Sale
0 Cezanne Dr Unit A4556644, Osprey, FL 34229

0 Cezanne Dr Unit A4556644, Osprey, FL 34229

/23
$745,000
- 4 Beds
- 3 Baths
- 2,557 Sq Ft
104 Park Trace Blvd, Osprey, FL 34229

Welcome to your dream home in beautiful Osprey, Florida inside PARK TRACE! This expansive 2557 sqft residence boasts 4 bedrooms and 3 bathrooms, designed for modern living and comfort. The master suite, located on the right side, offers a private oasis, while the other bedrooms are conveniently situated on the opposite side for maximum privacy.Step inside to an open-concept kitchen, perfect for

Jose Hugo Martinez KW COASTAL LIVING III

104 Park Trace Blvd, 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 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 & dryer

Alba Lange WAGNER REALTY

293 Hidden Bay Dr Unit 203, Osprey, FL 34229
/2
$1,350,000 Sold Mar 28, 2025
- 2,778 Sq Ft
- $486/SF
- 11 Days On Market
- 3 Beds
- 3 Baths
- Built 2004
409 N Point Rd Unit 704, Osprey, FL 34229

Enjoy luxury condo living at its finest. A rare offering, this 3 bedroom, 3 bath residence enjoys a spacious floor plan seldom available. Besides an incredible master suite, large guest bedrooms and modern bathrooms, it has a formal dining room, an office/den and an open great room with adjoining kitchen and breakfast nook. From the moment you step off your private elevator and enter, you will

Steve Abbe COLDWELL BANKER REALTY

409 N Point Rd Unit 704, Osprey, FL 34229

/29
Est $526,485 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,680 Sq Ft
313 Sorrento Dr, Osprey, FL 34229

313 Sorrento Dr, Osprey, FL 34229

/37
$269,000
- 2 Beds
- 2 Baths
- 1,379 Sq Ft
754 Pine Run Dr Unit 754, Osprey, FL 34229

Rarely available ground-floor 2-bedroom, 2-bath model with a standout location and layout that offers a truly one-of-a-kind living experience. This unique floorplan is centered around a private open-air atrium, accessible through 8-foot glass doors on three sides, filling the home with natural light and a seamless connection to the outdoors. From the south bedroom wing, you can look through walls

Sasha Volosevych CALL IT CLOSED INTL REALTY

754 Pine Run Dr Unit 754, Osprey, FL 34229
/2
$745,000 Sold Mar 27, 2025
- 2,594 Sq Ft
- $287/SF
- 17 Days On Market
- 3 Beds
- 3 Baths
- Built 2003
401 N Point Rd Unit 401, Osprey, FL 34229

Can luxury living and great value go hand and hand? It can with this well priced residence in Meridian at The Oaks Preserve. Nestled above the treetops, this luxury condo is the perfect solution for those who want to live a carefree lifestyle and enjoy all the amenities of Sarasota’s premier golf and country club. With 3 bedrooms, a den and 3 bath, this unit offers room for residents and guests

Steve Abbe COLDWELL BANKER REALTY

401 N Point Rd Unit 401, Osprey, FL 34229

/35
Est $430,148 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,430 Sq Ft
4242 Frontier Ln Unit 106, Osprey, FL 34229

4242 Frontier Ln Unit 106, Osprey, FL 34229

/39
$599,000
- 4 Beds
- 2 Baths
- 2,363 Sq Ft
104 Shoreland Dr, Osprey, FL 34229

Welcome to your coastal retreat! Currently set up as a furnished rental, This recently remodeled 4 bedroom 2 bathroom home offers modern comfort just moments from the water. Step inside to discover a bright, open floor plan with stylish updates throughout. Two large bedrooms lead out to the Lanai, where you can relax in the backyard Oasis featuring a heated spa Pool and outdoor kitchen- perfect

Mackenzie Davis OAKSTRAND REALTY

104 Shoreland Dr, Osprey, FL 34229
/2
$875,585 Sold Mar 27, 2025
- 1,937 Sq Ft
- $452/SF
- 13 Days On Market
- 3 Beds
- 2 Baths
- Built 2024
280 Hidden Bay Dr Unit 403, Osprey, FL 34229

One or more photo(s) has been virtually staged. Under Construction. 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 gated, 12-acre resort-style community is nestled on the water’s edge of

Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

280 Hidden Bay Dr Unit 403, Osprey, FL 34229

/31
Est $574,812 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,004 Sq Ft
4400 Conchfish Ln, Osprey, FL 34229

4400 Conchfish Ln, Osprey, FL 34229

/24
$549,000
- 2 Beds
- 2 Baths
- 1,738 Sq Ft
1363 New Forest Ln, Osprey, FL 34229

Welcome to The Woodlands At Rivendell! This beautiful home is on a large corner lot in the Patio Section of the Woodlands. It has TWO Bedrooms + a DEN, Great Room, double tray ceilings w/ crown molding. The den has double pocket doors! The kitchen is central in the house for entertaining, with plenty of storage, pull-out shelves, and 2 pantries! The Lanai has glimmering water views! Some nice

Pamela Strom RE/MAX PLATINUM

1363 New Forest Ln, Osprey, FL 34229
/2
$2,100,000 Sold Mar 26, 2025
- 4,641 Sq Ft
- $452/SF
- 95 Days On Market
- 4 Beds
- 3.5 Baths
- Built 2007
703 N MacEwen Dr, Osprey, FL 34229

Bathed in natural light, with highly sought after southern lanai exposure, is this stunning and meticulously maintained custom built John Cannon home in The Oaks Clubside. With 4 bedrooms, and 3 full and one half bathrooms, there is room for loved ones and guests, making it ideal for grand entertaining or peaceful and serene poolside relaxation. Enter through the elegant custom etched glass

Steve Abbe COLDWELL BANKER REALTY

703 N MacEwen Dr, Osprey, FL 34229

/43
Est $417,172 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,574 Sq Ft
4317 Expedition Way Unit 101, Osprey, FL 34229

4317 Expedition Way Unit 101, Osprey, FL 34229

/38
$815,000 Open Sat 1PM - 3PM
- 3 Beds
- 2 Baths
- 2,443 Sq Ft
901 Reflection Way, Osprey, FL 34229

LOCATION! LOCATION! Tucked away on a quiet cul-de-sac and resting on a corner lot, this METICULOUSLY MAINTAINED, Custom-built, JOHN CANNON home in exclusive North Creek Estates offers the perfect blend of privacy, luxury, and convenience. With a NEW ROOF (2020), low HOA fees, and 2,443 sq. ft. of thoughtfully designed living space, this 3-Bedroom + Office/Den, 2-Bath residence is MOVE-IN READY

Mark Lyda GENEROUS PROPERTY

901 Reflection Way, Osprey, FL 34229
/2
$925,000 Sold Mar 25, 2025
- 1,937 Sq Ft
- $478/SF
- 0 Days On Market
- 3 Beds
- 2 Baths
- Built 2024
280 Hidden Bay Dr Unit 503, Osprey, FL 34229

One or more photo(s) has been virtually staged. Under Construction. Just available is this rare, penthouse-level unit with unparalleled panoramic water views of Sarasota Bay and the Gulf of Mexico. A condominium with a view like this is seldom offered for sale and the top floor equals top views! Watch the most breathtaking sunsets from your private, extra-large, screened-in balcony on the 5th and

Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

280 Hidden Bay Dr Unit 503, Osprey, FL 34229

/31
Not Listed For Sale
0 Webb St Unit A4546155, Osprey, FL 34229

0 Webb St Unit A4546155, Osprey, FL 34229

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