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Osprey Homes For Sale & Osprey FL Real Estate

Home For Sale $1,695,000

Stunning home with a tile roof, paver driveway, lush landscaping, and serene water views at 402 Walls Way, Osprey, FL 34229
View Details 80 Photos
Beautiful home featuring a brick driveway and an attached three-car garage at 402 Walls Way, Osprey, FL 34229
Stunning home showcasing meticulous landscaping, a brick driveway, and a serene, tree-lined backdrop at 402 Walls Way, Osprey, FL 34229
Covered outdoor living space featuring brick flooring, ceiling fans, and an inviting ambiance at 402 Walls Way, Osprey, FL 34229
On Market For 2 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3464

  • Year Built

    2014

  • $/SqFt

    $489

Situated in the heart of South Sarasota, The Oaks Club is home to 2 championship golf courses, has a world class tennis program, a state-of-the-art WellFit center, exceptional dining options, and a myriad of recreational and social activities. COLDWELL BANKER REALTY.

Home For Sale $779,900

Charming single-story home featuring mature landscaping and a well-maintained driveway leading to a two-car garage at 826 Oak Briar Ln, Osprey, FL 34229
View Details 67 Photos
Inviting screened-in patio with comfortable seating overlooking a private pool and well-kept backyard at 826 Oak Briar Ln, Osprey, FL 34229
Attractive home entrance with a modern front door, decorative stone landscaping, and charming outdoor seating at 826 Oak Briar Ln, Osprey, FL 34229
Expansive aerial view of the property showcasing its lush landscaping and well-maintained surroundings at 826 Oak Briar Ln, Osprey, FL 34229
On Market For 6 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2589

  • Year Built

    2003

  • $/SqFt

    $301

Because success should feel like a getaway—live the vacation lifestyle every day here at 826 Oak Briar Lane. PREFERRED SHORE LLC.

Home For Sale $659,000

Charming single Gathering home with lush landscaping and a two-car garage, in a desirable neighborhood at 51 Webb St, Osprey, FL 34229
View Details 61 Photos
Gorgeous aerial view of neighborhood featuring beautiful waterfront views and lush landscapes under clear blue skies at 51 Webb St, Osprey, FL 34229
Beautiful aerial view of waterfront community with picturesque coastlines and homes surrounded by lush greenery at 51 Webb St, Osprey, FL 34229
Charming single-story home with a well-manicured lawn, screened entrance, and an attached two-car garage at 51 Webb St, Osprey, FL 34229
On Market For 8 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2130

  • Year Built

    1978

  • $/SqFt

    $309

Don't miss this opportunity to own a piece of paradise—schedule your private showing today! FINE PROPERTIES.

Home For Sale $1,100,000

Charming single-story home with well-manicured lawn and a paver driveway leading to an attached two-car garage at 742 Shadow Bay Way, Osprey, FL 34229
View Details 61 Photos
Paver driveway leading to charming single-story home with well-manicured lawn and an attached two-car garage at 742 Shadow Bay Way, Osprey, FL 34229
Attractive single-story home featuring manicured landscaping, a paver driveway, and a welcoming double-door entryway at 742 Shadow Bay Way, Osprey, FL 34229
Inviting entryway with double doors and manicured landscaping, offering a glimpse of the well-maintained property at 742 Shadow Bay Way, Osprey, FL 34229
*POTENTIAL GREAT VALUE
On Market For 10 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3321

  • Year Built

    2002

  • $/SqFt

    $331

This is a rare opportunity to own a beautifully updated home in one of Osprey’s most desirable communities. Schedule your private showing today. RE/MAX ALLIANCE GROUP.

Pended $929,000

Charming two-story home with a lush, landscaped yard and a spacious driveway at 851 E Bay St, Osprey, FL 34229
View Details 58 Photos
Stunning aerial view of a landscaped home with lush greenery and a circular driveway at 851 E Bay St, Osprey, FL 34229
Birds eye view of a home surrounded by lush trees and a large, green lawn at 851 E Bay St, Osprey, FL 34229
A serene pond with lily pads, a statue, and a gentle waterfall feature at 851 E Bay St, Osprey, FL 34229
On Market For 11 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2329

  • Year Built

    2002

  • $/SqFt

    $399

Ideally Located close to Area Beaches including #1-Rated SIESTA BEACH, the Popular LEGACY BIKE TRAIL, #1-Rated PINE VIEW SCHOOL, Shopping, Downtown Sarasota and Venice cultural venues, and all that Florida’s Gulf Coast Living has to offer. GENEROUS PROPERTY.

Home For Sale $4,750,000

Stunning aerial view of a beachfront estate with turquoise waters and a sandy beach at 1049 N Casey Key Rd, Osprey, FL 34229
View Details 64 Photos
Long driveway leading up to this luxurious house with lush greenery at 1049 N Casey Key Rd, Osprey, FL 34229
This beautiful home has mature trees, a dock and easy access to the Gulf of Mexico! at 1049 N Casey Key Rd, Osprey, FL 34229
Sun-filled living room featuring a fireplace and an expansive view of the tropical outdoors at 1049 N Casey Key Rd, Osprey, FL 34229
On Market For 12 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2582

  • Year Built

    1990

  • $/SqFt

    $1,840

Experience the ultimate coastal lifestyle and make this paradise yours. PREMIER SOTHEBYS INTL REALTY.

Home For Sale $11,750,000

Elegant two-story home featuring mature trees, a circular driveway, and a well-manicured lawn with lush landscaping at 1216 N Casey Key Rd, Osprey, FL 34229
View Details 60 Photos
Breathtaking aerial view of an estate home with pool, a private dock, and stunning ocean views at 1216 N Casey Key Rd, Osprey, FL 34229
Beautiful outdoor living area with a large pool, patio, and lush landscaping, perfect for entertaining and relaxation at 1216 N Casey Key Rd, Osprey, FL 34229
Stately home with brick driveway, elegant landscaping, and mature trees for privacy and curb appeal at 1216 N Casey Key Rd, Osprey, FL 34229
On Market For 16 Days

  • Bedrooms

    5

  • Full Bath(s)

    6

  • Sq. Ft.

    8050

  • Year Built

    1999

  • $/SqFt

    $1,460

North Casey Key is a haven of exclusivity and serenity, minutes from shopping, world-class golf, tennis and dining. PREMIER SOTHEBYS INTL REALTY.

Home For Sale $774,900

Lovely home features a paved driveway, tile roof, lush landscaping, and an attached two-car garage at 866 Placid Lake Dr, Osprey, FL 34229
View Details 62 Photos
Lovely home at twilight features a paved driveway, tile roof, lush landscaping, and an attached two-car garage at 866 Placid Lake Dr, Osprey, FL 34229
Charming single-story home with a paved driveway, tile roof, two-car garage, and professionally landscaped yard at 866 Placid Lake Dr, Osprey, FL 34229
Up close shot of the home's mailbox with number plaque and a partial view of the home and two-car garage at 866 Placid Lake Dr, Osprey, FL 34229
On Market For 11 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2171

  • Year Built

    2002

  • $/SqFt

    $357

Rivendell The Woodlands - This Osprey location provides convenient access to the Legacy Trail, pristine beaches, and the vibrant cultural scenes of Sarasota and Venice. KELLER WILLIAMS ON THE WATER S.

Home For Sale $2,995,000

Stunning aerial view of an exclusive waterfront home with lush landscaping and a private lake at 49 Osprey Point Dr, Osprey, FL 34229
View Details 95 Photos
Elegant home featuring manicured landscaping, a neutral facade, and a welcoming entrance at 49 Osprey Point Dr, Osprey, FL 34229
Beautiful home featuring a stone walkway leading to a striking entryway and modern design at 49 Osprey Point Dr, Osprey, FL 34229
Zen courtyard with stone fountain, pebble ground cover, and serene views through floor to ceiling windows at 49 Osprey Point Dr, Osprey, FL 34229
On Market For 18 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3953

  • Year Built

    1989

  • $/SqFt

    $758

At 49 Osprey Point Drive, every detail has been meticulously crafted for those who seek refined living and unparalleled elegance. MICHAEL SAUNDERS & COMPANY.

Home For Sale $1,200,000

Expansive aerial view of a home with a screened pool surrounded by lush greenery at 201 Eaglenook Way, Osprey, FL 34229
View Details 88 Photos
Entrance sign to Pine Ranch framed by lush landscaping at 201 Eaglenook Way, Osprey, FL 34229
Charming home featuring a well-manicured front yard with a welcoming red front door at sunset at 201 Eaglenook Way, Osprey, FL 34229
Inviting screened-in pool with a built-in spa, tiled trim, and poolside seating at 201 Eaglenook Way, Osprey, FL 34229
*POTENTIAL GREAT VALUE
On Market For 18 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3379

  • Year Built

    1992

  • $/SqFt

    $355

For property video, 3-D walk thru and floor plan please visit https://hub.allanglesrem.com/view/?s=1989285&nohit=1 WILLIAM RAVEIS REAL ESTATE.

Home For Sale $1,390,000

Stunning two-story home featuring a three-car garage, beautiful landscaping, and a brick paved driveway at 820 Placid Lake Dr, Osprey, FL 34229
View Details 69 Photos
Beautiful two-story house with a paved driveway, three-car garage, lush landscaping, and warm, inviting lighting at 820 Placid Lake Dr, Osprey, FL 34229
Beautiful two-story house featuring a three-car garage, lush landscaping, and a patterned brick driveway at 820 Placid Lake Dr, Osprey, FL 34229
Charming front entrance with a beautiful double-door, decorative plants, and a tiled walkway at 820 Placid Lake Dr, Osprey, FL 34229
*POTENTIAL GREAT VALUE
On Market For 19 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3938

  • Year Built

    2002

  • $/SqFt

    $353

Rivendell The Woodlands - Don't miss this rare opportunity to own a stunning lakefront retreat in Woodlands at Rivendell! LOYD ROBBINS & CO. LLC.

Home For Sale $875,000

Charming home features a lush landscaped yard and a welcoming brick pathway to the front door at 402 Pine Ranch East Rd, Osprey, FL 34229
View Details 30 Photos
Relaxing backyard pool with an attached jacuzzi, brick pavers, and a screened enclosure at 402 Pine Ranch East Rd, Osprey, FL 34229
Bright kitchen with an island, white tiled floors, cabinetry and lots of natural light at 402 Pine Ranch East Rd, Osprey, FL 34229
Updated kitchen boasts an island, tiled backsplash, and stainless steel appliances at 402 Pine Ranch East Rd, Osprey, FL 34229
On Market For 14 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2887

  • Year Built

    1995

  • $/SqFt

    $303

This Is Being Sold As Is With Right To Inspect. CARON REALTY INC.

Home For Sale $430,000

Charming yellow home featuring a screened-in porch and well-maintained landscaping at 109 Burney Rd, Osprey, FL 34229
View Details 56 Photos
Aerial view showcasing the property's location near the water and retail area at 109 Burney Rd, Osprey, FL 34229
Charming home with lush landscaping, a carport, and a welcoming driveway at 109 Burney Rd, Osprey, FL 34229
A glimpse of the property's driveway, surrounded by lush, mature landscaping at 109 Burney Rd, Osprey, FL 34229
On Market For 22 Days

  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    714

  • Year Built

    1959

  • $/SqFt

    $602

Don't miss this unique opportunity—schedule your private showing today! MANGROVE REALTY ASSOCIATES.

Home For Sale $910,000

Charming single-story home with a tile roof, lush landscaping, and a three-car garage at 608 Crane Prairie Way, Osprey, FL 34229
View Details 62 Photos
Beautiful aerial view of several homes backing onto a tranquil pond surrounded by lush greenery at 608 Crane Prairie Way, Osprey, FL 34229
Gorgeous aerial view of a home next to a lake in a neighborhood at 608 Crane Prairie Way, Osprey, FL 34229
Overhead shot of houses with pools in a lakeside community, highlighting landscaping at 608 Crane Prairie Way, Osprey, FL 34229
On Market For 23 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2678

  • Year Built

    2005

  • $/SqFt

    $340

This home and its surroundings offer an abundance of features and amenities—truly a must-see! GULF SHORES REALTY.

Home For Sale $625,000

Charming one-story home featuring a red tile roof, lush landscaping, and a well-manicured front yard at 221 Sorrento Dr, Osprey, FL 34229
View Details 41 Photos
This home includes a large driveway, perfect for multiple vehicles, and a classic, neutral color palette at 221 Sorrento Dr, Osprey, FL 34229
Elegant front door with decorative glass and sidelights, complemented by a welcoming rug at 221 Sorrento Dr, Osprey, FL 34229
Cozy outdoor patio with brick flooring, surrounded by lush tropical landscaping and comfortable seating at 221 Sorrento Dr, Osprey, FL 34229
On Market For 24 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1935

  • Year Built

    1984

  • $/SqFt

    $323

Don't miss your chance to live the Florida lifestyle you've been dreaming of. Schedule your showing today. COLDWELL BANKER SARASOTA CENT..

Home For Sale $285,000

Charming home featuring a cozy front porch, lush landscaping, and great curb appeal at 452 Patterson Ave, Osprey, FL 34229
View Details 40 Photos
Inviting home exterior with well-maintained landscaping, carport, and ample parking space at 452 Patterson Ave, Osprey, FL 34229
Well-maintained exterior showing front yard with tropical landscaping, providing a serene setting at 452 Patterson Ave, Osprey, FL 34229
Inviting home exterior with lush landscaping, and stone walkway leading to a cozy porch at 452 Patterson Ave, Osprey, FL 34229
On Market For 24 Days

  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    520

  • Year Built

    1949

  • $/SqFt

    $548

Move-in ready as a primary residence, winter getaway or annual/seasonal rental. BRIGHT REALTY.

Home For Sale $1,675,000

Beautiful single-story home featuring lush landscaping, gray tile roof, and a welcoming red double-door entrance at 20 Bayhead Ln, Osprey, FL 34229
View Details 78 Photos
Aerial shot of the pool area, showcasing screened-in pool, patio furniture and serene backyard pond at 20 Bayhead Ln, Osprey, FL 34229
Expansive aerial perspective of the property, highlighting its position near a tranquil pond and surrounding greenery at 20 Bayhead Ln, Osprey, FL 34229
Overhead view showcasing the home's location, complete with a pond, mature trees, and neighboring residences at 20 Bayhead Ln, Osprey, FL 34229
On Market For 30 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3486

  • Year Built

    2017

  • $/SqFt

    $480

Don’t miss this opportunity to own a piece of paradise—schedule your private tour today! SARASOTA LAND AND HOMES LLC.

Home For Sale $549,500

Inviting home with well-manicured landscaping, tile roof, and a two-car garage on a sunny day at 574 Crane Prairie Way, Osprey, FL 34229
View Details 51 Photos
Charming home with a tile roof, lush lawn, and manicured landscaping creating curb appeal at 574 Crane Prairie Way, Osprey, FL 34229
Close-up of the front entrance featuring a brick walkway, glass front door, and a two-car garage at 574 Crane Prairie Way, Osprey, FL 34229
Screened-in pool with brick trim and an umbrella table set surrounded by lush greenery at 574 Crane Prairie Way, Osprey, FL 34229
On Market For 30 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1850

  • Year Built

    2005

  • $/SqFt

    $297

Willowbend - Enjoy the benefits of being in a preferred X flood zone with no CDD fees, making this residence a blend of beauty, comfort and convenience. PREMIER SOTHEBYS INTL REALTY.

Home For Sale $1,685,000

Waterfront home featuring a private dock, a swimming pool, lush landscaping and gorgeous palm trees at 364 El Greco Dr, Osprey, FL 34229
View Details 50 Photos
Well-maintained front yard with lush landscaping and a circular driveway leading to the home at 364 El Greco Dr, Osprey, FL 34229
Sprawling neighborhood showcasing canal, waterfront living, lush landscaping and beautiful homes at 364 El Greco Dr, Osprey, FL 34229
Balcony with seating overlooking the canal and lush landscaping with beautiful views at 364 El Greco Dr, Osprey, FL 34229
On Market For 33 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2402

  • Year Built

    1964

  • $/SqFt

    $701

Whether you're observing dolphins and manatees from your deck or enjoying the vibrant local arts scene, this residence embodies the waterfront frame for an exceptional life. PREMIER SOTHEBYS INTL REALTY.

Home For Sale $525,000

Reduced By $40,000

Charming single-story home featuring lush landscaping, including palm trees, shrubbery, and colorful flowers at 564 Meadow Sweet Cir, Osprey, FL 34229
View Details 55 Photos
Beautiful home showcasing a well-maintained driveway, complemented by verdant landscaping and mature trees at 564 Meadow Sweet Cir, Osprey, FL 34229
Inviting front entrance featuring a brick walkway, charming bench, and views of the home's facade at 564 Meadow Sweet Cir, Osprey, FL 34229
Spacious living room with hardwood floors, and an open concept layout ideal for modern living at 564 Meadow Sweet Cir, Osprey, FL 34229
On Market For 37 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1808

  • Year Built

    2003

  • $/SqFt

    $290

It is a great space to sit down with your favorite book and simply relax. PREMIER SOTHEBYS INTL REALTY.

Home For Sale $2,395,000

Beautiful beach house featuring palm trees and ocean views at sunset at 140 N Casey Key Rd, Osprey, FL 34229
View Details 83 Photos
Bright living room with high ceilings, large windows, and a view of the water at 140 N Casey Key Rd, Osprey, FL 34229
Open floor plan featuring living room connected to the kitchen and high ceilings at 140 N Casey Key Rd, Osprey, FL 34229
Spacious living room with large windows and a view of the water and outdoor deck at 140 N Casey Key Rd, Osprey, FL 34229
On Market For 39 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2473

  • Year Built

    1985

  • $/SqFt

    $968

Experience the ultimate in island living—schedule your private tour today! KELLER WILLIAMS ON THE WATER.

Pended $975,000

Charming home featuring a well-manicured lawn and mature landscaping with an architectural window feature at 128 Sea Anchor Dr, Osprey, FL 34229
View Details 80 Photos
Breathtaking aerial view of a home, nestled in a lush, green neighborhood with a screened pool and waterfront access at 128 Sea Anchor Dr, Osprey, FL 34229
Bright, inviting living room with a soaring ceiling, large windows, travertine floors, and an adjacent mezzanine at 128 Sea Anchor Dr, Osprey, FL 34229
Inviting living room featuring travertine floors, soaring ceiling, large windows and neutral decor at 128 Sea Anchor Dr, Osprey, FL 34229
On Market For 28 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2677

  • Year Built

    1978

  • $/SqFt

    $364

Southbay Yacht & Racquet Club - Don't miss the chance to experience this exceptional waterfront lifestyle. PREMIER SOTHEBYS INTL REALTY.

Home For Sale $1,995,000

Breathtaking aerial view of waterfront home at sunset, showcasing lush landscaping and water access at 525 S Shore Dr, Osprey, FL 34229
View Details 64 Photos
Stunning home featuring a well-manicured lawn and a circular driveway enhancing its curb appeal at 525 S Shore Dr, Osprey, FL 34229
Expansive aerial view of a luxury estate with a waterfront location and manicured grounds at 525 S Shore Dr, Osprey, FL 34229
Inviting front entrance with elegant stone accents, manicured garden, and a modern doorway at 525 S Shore Dr, Osprey, FL 34229
On Market For 41 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2315

  • Year Built

    1972

  • $/SqFt

    $862

Info available about ability to add a dock. COLDWELL BANKER REALTY.

Home For Sale $1,995,000

Elegant home showcasing a circular paver driveway, lush landscaping, and a three-car garage at 67 Sugar Mill Dr, Osprey, FL 34229
View Details 93 Photos
Charming one-story home features arched windows, a red door, and well-manicured landscaping at 67 Sugar Mill Dr, Osprey, FL 34229
Overhead view of the home with screened lanai, nestled amidst lush trees and greenery at 67 Sugar Mill Dr, Osprey, FL 34229
A captivating aerial view shows a neighborhood with a lake and ocean in the distance at 67 Sugar Mill Dr, Osprey, FL 34229
On Market For 31 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    4020

  • Year Built

    1989

  • $/SqFt

    $496

The furniture in the home is from a staging company and is not owned by the seller and not for sale MAPP REALTY & INVESTMENT CO.

Pended $785,000

Beautifully landscaped home with brick paved driveway, mature palm trees, and tile roof at 779 Fordingbridge Way, Osprey, FL 34229
View Details 40 Photos
Aerial view of coastal community highlighting location of home, beaches, and nearby amenities at 779 Fordingbridge Way, Osprey, FL 34229
Aerial view of house showing pool, landscaping, backyard, and outdoor space at 779 Fordingbridge Way, Osprey, FL 34229
Home floor plan showing layout of bedrooms, bathrooms, living areas, and garage at 779 Fordingbridge Way, Osprey, FL 34229
On Market For 37 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2154

  • Year Built

    2002

  • $/SqFt

    $364

Rivendell The Woodlands - Rivendell is just minutes to world class sand beaches of Siesta Key and Nokomis beach, Oscar Scherer state park, Legacy bike trail Bay Street park junction, shopping plaza, dining, and adjacent to the nationally recognized public 2-12 Pine View school for gifted students (contact Sarasota County Schools for details) RE/MAX ALLIANCE GROUP.

Home For Sale $749,000

Reduced By $50,000

An aerial view of a home with a red tile roof, a screened-in pool, and lush landscaping at 1426 Landview Ln, Osprey, FL 34229
View Details 46 Photos
A charming single-story home with lush landscaping, a driveway, and a two-car garage at 1426 Landview Ln, Osprey, FL 34229
A close-up of the front entrance featuring an arched window, a pathway, and manicured shrubbery at 1426 Landview Ln, Osprey, FL 34229
A well-staged living room with vaulted ceilings, neutral colors, and a view of the pool at 1426 Landview Ln, Osprey, FL 34229
On Market For 44 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2513

  • Year Built

    1987

  • $/SqFt

    $298

It is more than just a place to live; it is a lifestyle waiting to be embraced. COLDWELL BANKER REALTY.

Home For Sale $1,700,000

Aerial view of a luxurious home nestled in a waterfront community at 282 Shell Midden Ct, Osprey, FL 34229
View Details 100 Photos
Impressive two-story home with a grand entrance and manicured landscaping at 282 Shell Midden Ct, Osprey, FL 34229
Elegant home with a three-car garage and inviting walkway at 282 Shell Midden Ct, Osprey, FL 34229
Stunning home showcasing a spacious driveway and lush landscaping at 282 Shell Midden Ct, Osprey, FL 34229
On Market For 48 Days

  • Bedrooms

    3

  • Full Bath(s)

    4

  • Sq. Ft.

    3699

  • Year Built

    1992

  • $/SqFt

    $460

Club membership is required with homeownership. COLDWELL BANKER REALTY.

Home For Sale $769,000

Reduced By $30,000

Stunning waterfront home with lush landscaping, spacious driveway and beautiful terracotta tile roof at 146 Willow Bend Way, Osprey, FL 34229
View Details 70 Photos
Beautiful waterfront home featuring lush landscaping, spacious driveway and terracotta tile roof at 146 Willow Bend Way, Osprey, FL 34229
Gorgeous aerial view of waterfront home in a residential neighborhood at 146 Willow Bend Way, Osprey, FL 34229
Beautiful aerial view of waterfront home with lush landscaping at 146 Willow Bend Way, Osprey, FL 34229
On Market For 48 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2540

  • Year Built

    2002

  • $/SqFt

    $303

Schedule your showing today and make this beautiful life yours! PREMIER SOTHEBYS INTL REALTY.

Home For Sale $2,350,000

Reduced By $350,000

Attractive home with a large, paved driveway and lush landscaping at 18 N Casey Key Rd, Osprey, FL 34229
View Details 49 Photos
Inviting entryway with a pergola and tropical landscaping at 18 N Casey Key Rd, Osprey, FL 34229
Aerial view of waterfront property with canal access at 18 N Casey Key Rd, Osprey, FL 34229
Wide aerial view of property, showing house and large lot at 18 N Casey Key Rd, Osprey, FL 34229
On Market For 51 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1977

  • Year Built

    1973

  • $/SqFt

    $1,189

Close to shopping, restaurants, golf, tennis, recreational amenities, and just a short drive to vibrant cities of Sarasota and Venice. PREMIER SOTHEBYS INTL REALTY.

Pended $1,025,000

Aerial view of waterfront home with private dock and lush landscaping at 505 S Shore Dr, Osprey, FL 34229
View Details 34 Photos
Aerial view showcasing a waterfront home's location and neighborhood at 505 S Shore Dr, Osprey, FL 34229
An aerial view of a waterfront property, highlighting its location and canal access at 505 S Shore Dr, Osprey, FL 34229
Aerial view highlighting a waterfront home's expansive lot and canal views at 505 S Shore Dr, Osprey, FL 34229
On Market For 51 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2301

  • Year Built

    1980

  • $/SqFt

    $445

Sorrento Shores - Call now to see this gem! COLDWELL BANKER REALTY.

Pended $2,495,000

Stunning curb appeal! This home features a beautiful tile walkway leading to the entrance at 230 Osprey Point Dr, Osprey, FL 34229
View Details 69 Photos
Inviting pool area with a covered lanai and comfortable seating at 230 Osprey Point Dr, Osprey, FL 34229
Elegant living room with hardwood floors, fireplace, and ample natural light at 230 Osprey Point Dr, Osprey, FL 34229
Gourmet kitchen boasting granite countertops and stainless steel appliances at 230 Osprey Point Dr, Osprey, FL 34229
On Market For 44 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    3586

  • Year Built

    2014

  • $/SqFt

    $696

**ENJOY THE 3D VIRTUAL TOUR and AERIAL VIDEO** GENEROUS PROPERTY.

Home For Sale $1,099,000

Beautiful two-story home with a manicured lawn and palm trees at 366 S Creek Ct, Osprey, FL 34229
View Details 46 Photos
Two-story house with a lush green lawn, palm trees, and a brick driveway at 366 S Creek Ct, Osprey, FL 34229
Inviting front porch with double doors, a bench, and comfortable seating at 366 S Creek Ct, Osprey, FL 34229
Bright and airy entryway with double doors and a stylish console table at 366 S Creek Ct, Osprey, FL 34229
On Market For 51 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2775

  • Year Built

    2004

  • $/SqFt

    $396

This home is in the "X" flood zone so flood insurance is optional. KELLER WILLIAMS ON THE WATER S.

Home For Sale $583,000

Aerial view of a beautiful home in a desirable neighborhood with a lake at 531 Latitude Ln, Osprey, FL 34229
View Details 51 Photos
Single-story home with attached garage and lush landscaping at 531 Latitude Ln, Osprey, FL 34229
Bird's eye view of a house and neighborhood with a lake at 531 Latitude Ln, Osprey, FL 34229
Aerial view showing home's location in a waterfront community at 531 Latitude Ln, Osprey, FL 34229
On Market For 46 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1857

  • Year Built

    2004

  • $/SqFt

    $314

The property is also free of CDD fees and is in a preferred X flood zone, making it an ideal blend of luxury, convenience and security. PREMIER SOTHEBYS INTL REALTY.

Pended $450,000

Reduced By $25,000

Single-story house with a light-colored exterior, a two-car garage, and nicely landscaped yard at 441 N Shore Dr, Osprey, FL 34229
View Details 27 Photos
Aerial view showing the property's location in a residential neighborhood near the water at 441 N Shore Dr, Osprey, FL 34229
Bright and airy living room with tiled floors, comfortable seating, and a dining area at 441 N Shore Dr, Osprey, FL 34229
Spacious living room with tiled floors, sliding doors leading to a screened-in patio at 441 N Shore Dr, Osprey, FL 34229
On Market For 50 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1334

  • Year Built

    1970

  • $/SqFt

    $337

One or more photo(s) has been virtually staged. EXIT KING REALTY.

Home For Sale $3,150,000

Beautiful 1-story home with a tile roof and lush landscaping at 662 Fernwalk Ln, Osprey, FL 34229
View Details 80 Photos
Luxury home nestled in a quiet neighborhood with water views at 662 Fernwalk Ln, Osprey, FL 34229
Inviting pool and spa area with screened enclosure and patio furniture at 662 Fernwalk Ln, Osprey, FL 34229
Spacious living room featuring hardwood floors and a cozy fireplace at 662 Fernwalk Ln, Osprey, FL 34229
On Market For 52 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    4684

  • Year Built

    1989

  • $/SqFt

    $673

**ENJOY THE 3D VIRTUAL TOUR and AERIAL VIDEO** GENEROUS PROPERTY.

Pended $289,000

Reduced By $10,000

Charming single-story home with a well-maintained front yard and a classic suburban aesthetic at 208 Pennsylvania Ave, Osprey, FL 34229
View Details 26 Photos
Aerial view of a property showcasing its location within a residential neighborhood near a lake at 208 Pennsylvania Ave, Osprey, FL 34229
High-angle view shows the property surrounded by lush greenery and nearby amenities at 208 Pennsylvania Ave, Osprey, FL 34229
Bird's-eye view of a house with surrounding greenery and street access on a sunny day at 208 Pennsylvania Ave, Osprey, FL 34229
On Market For 52 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    900

  • Year Built

    1963

  • $/SqFt

    $321

Turn-key and ready to move in, New paint FLAT FEE MLS REALTY.

Home For Sale $1,164,000

Reduced By $25,000

Aerial view of two-story home with tile roof, landscaping, and water views at 3904 Waypoint Ave, Osprey, FL 34229
View Details 43 Photos
Tan house with tile roof, landscaping, and two-car garage at 3904 Waypoint Ave, Osprey, FL 34229
Aerial view of a single Gathering home with a two-car garage and lush landscaping at 3904 Waypoint Ave, Osprey, FL 34229
Wide aerial view of waterfront community with single Gathering home highlighted at 3904 Waypoint Ave, Osprey, FL 34229
On Market For 53 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2344

  • Year Built

    2016

  • $/SqFt

    $497

With its prime location on a quiet cul-de-sac, this home promises an incredible lifestyle enriched by the natural beauty of its surroundings. PREMIER SOTHEBYS INTL REALTY.

Home For Sale $900,000

Reduced By $75,000

Charming single-story home with stone accents, a tile roof, and well-maintained landscaping at 1237 Flying Bridge Ln, Osprey, FL 34229
View Details 70 Photos
Sparkling screened-in pool and spa with lush tropical landscaping at 1237 Flying Bridge Ln, Osprey, FL 34229
Inviting front entrance with patterned tile and lush landscaping at 1237 Flying Bridge Ln, Osprey, FL 34229
Bright and airy entryway with a tiled floor and neutral color palette at 1237 Flying Bridge Ln, Osprey, FL 34229
On Market For 52 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2045

  • Year Built

    1978

  • $/SqFt

    $440

Conveniently located between Sarasota and Venice with shopping, dining, beaches and more, close a hand. PAT WILLIAMS REALTY, LLC.

Home For Sale $850,000

Reduced By $45,000

Charming home featuring a red roof, lush landscaping, and a welcoming entrance, complemented by a paved driveway and palm trees at 424 Cezanne Dr, Osprey, FL 34229
View Details 53 Photos
Bird's-eye view of a house and surrounding neighborhood at 424 Cezanne Dr, Osprey, FL 34229
Open dining area with kitchen access and tile floors at 424 Cezanne Dr, Osprey, FL 34229
Bright dining room with access to a screened porch at 424 Cezanne Dr, Osprey, FL 34229
On Market For 54 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    2945

  • Year Built

    1975

  • $/SqFt

    $289

Welcome home to your slice of paradise! MICHAEL SAUNDERS & COMPANY.

Home For Sale $1,325,000

Reduced By $75,000

Attractive two-story house with three-car garage, manicured landscaping, and a circular driveway at 135 N Creek Ln, Osprey, FL 34229
View Details 49 Photos
Luxury home with pool, situated in a residential neighborhood near water at 135 N Creek Ln, Osprey, FL 34229
Community overview featuring a golf course, water features, and numerous houses at 135 N Creek Ln, Osprey, FL 34229
Beautiful house with a three-car garage, palm trees, and well-maintained landscaping at 135 N Creek Ln, Osprey, FL 34229
On Market For 57 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3160

  • Year Built

    2005

  • $/SqFt

    $419

Experience the pinnacle of Florida living in this exceptional home. PREMIER SOTHEBYS INTL REALTY.

Home For Sale $769,900

Reduced By $10,100

Single-story house with tile roof, attached garage, and landscaped yard at 1212 Windward Dr, Osprey, FL 34229
View Details 39 Photos
An aerial view showcasing a home's location within a residential community at 1212 Windward Dr, Osprey, FL 34229
An aerial view of a single story home with a red tile roof in a residential neighborhood at 1212 Windward Dr, Osprey, FL 34229
Bright kitchen boasts white cabinets, tile floors, and ample counter space at 1212 Windward Dr, Osprey, FL 34229
On Market For 58 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1994

  • Year Built

    1982

  • $/SqFt

    $386

Southbay is just minutes from nationally ranked Pine View School, the Legacy Bike Trail, area Beaches and all that Gulf Coast living has to offer. GENEROUS PROPERTY.

Home For Sale $579,000

Two-story elevated home with carport and tropical landscaping at 0 Westview Dr, Osprey, FL 34229
View Details 21 Photos
Two-story elevated home with carport, showcasing the rear at 0 Westview Dr, Osprey, FL 34229
Two-story elevated home with carport, showcasing the side at 0 Westview Dr, Osprey, FL 34229
Two-story elevated home with carport, showcasing the side at 0 Westview Dr, Osprey, FL 34229
On Market For 60 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1600

  • Year Built

    2025

  • $/SqFt

    $362

Towns End Shores - Don’t miss the chance to make your dream home a reality in a setting that truly has it all. KELLER WILLIAMS ON THE WATER S.

Home For Sale $2,450,000

Luxury home with pool and lush landscaping on a golf course at 654 Trenton Way, Osprey, FL 34229
View Details 85 Photos
Resort-style backyard oasis with pool, fire pit, and patio at 654 Trenton Way, Osprey, FL 34229
Inviting freeform pool and spa with covered patio and sunset views at 654 Trenton Way, Osprey, FL 34229
Relaxing fire pit area with comfortable seating in the backyard at 654 Trenton Way, Osprey, FL 34229
On Market For 61 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3582

  • Year Built

    1990

  • $/SqFt

    $684

**ENJOY THE 3D VIRTUAL TOUR and AERIAL VIDEO** GENEROUS PROPERTY.

Home For Sale $6,950,000

Reduced By $445,000

Luxury waterfront home with pool and private dock at sunset at 144 N Casey Key Rd, Osprey, FL 34229
View Details 100 Photos
Private dock leading to a luxury waterfront home at 144 N Casey Key Rd, Osprey, FL 34229
Luxury waterfront home community with private docks at 144 N Casey Key Rd, Osprey, FL 34229
Grand waterfront home with elegant stone and blue exterior at 144 N Casey Key Rd, Osprey, FL 34229
On Market For 65 Days

  • Bedrooms

    4

  • Full Bath(s)

    5

  • Sq. Ft.

    5397

  • Year Built

    2003

  • $/SqFt

    $1,288

This is more than a home; it’s a sanctuary where luxury meets tranquility, and a legacy waiting to be claimed. Schedule your private showing today. EXP REALTY LLC.

Pended $1,250,000

Aerial view of waterfront home with private dock and pool at 131 Tina Island Dr, Osprey, FL 34229
View Details 44 Photos
House with circular driveway, waterfront property, and lush landscaping at 131 Tina Island Dr, Osprey, FL 34229
Single-story home with a white garage door, lush landscaping, and a circular driveway at 131 Tina Island Dr, Osprey, FL 34229
Inviting entryway with a decorative arch, white columns, and a walkway at 131 Tina Island Dr, Osprey, FL 34229
On Market For 35 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1787

  • Year Built

    1978

  • $/SqFt

    $699

Call today to schedule your private showing. WHITE SANDS REALTY GROUP FL.

Home For Sale $2,650,000

Stunning home with lush landscaping, circular drive and elegant portico entry with round columns at 370 Sugar Mill Dr, Osprey, FL 34229
View Details 85 Photos
Inviting pool area with covered patio, outdoor kitchen, and ample seating at 370 Sugar Mill Dr, Osprey, FL 34229
Waterfront property with beautiful landscaping and a prime location at 370 Sugar Mill Dr, Osprey, FL 34229
Beautiful home showcasing tropical landscaping, circular drive and covered front entry at 370 Sugar Mill Dr, Osprey, FL 34229
On Market For 64 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4783

  • Year Built

    1996

  • $/SqFt

    $554

Membership is required and there is NO WAITLIST for GOLF or SOCIAL Membership. GENEROUS PROPERTY.

Home For Sale $725,000

Reduced By $24,900

Attractive single-story home with landscaped yard and palm trees at 455 Park Trace Blvd, Osprey, FL 34229
View Details 40 Photos
Single-story house with lush landscaping and a palm tree in front at 455 Park Trace Blvd, Osprey, FL 34229
Peaceful lakefront view with homes and lush greenery at 455 Park Trace Blvd, Osprey, FL 34229
Serene lake view from a lush, grassy backyard at 455 Park Trace Blvd, Osprey, FL 34229
On Market For 65 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2590

  • Year Built

    1999

  • $/SqFt

    $280

Nestled in a beautifully maintained neighborhood with unusually low HOA fees (under $57 a MONTH), this home offers a rare opportunity to experience waterfront living at an exceptional price! MICHAEL SAUNDERS & COMPANY.

Home For Sale $1,175,000

Reduced By $50,000

Beautiful yellow home with lush landscaping and a large driveway at 227 Saint James Park, Osprey, FL 34229
View Details 67 Photos
Relaxing screened patio with outdoor furniture and view of lush greenery at 227 Saint James Park, Osprey, FL 34229
Aerial view of house and golf course community at 227 Saint James Park, Osprey, FL 34229
Bright yellow house with a large driveway and manicured lawn at 227 Saint James Park, Osprey, FL 34229
On Market For 66 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    2071

  • Year Built

    1986

  • $/SqFt

    $567

Membership is required and there is NO WAITLIST for GOLF or SOCIAL Membership. GENEROUS PROPERTY.

Home For Sale $1,095,000

Reduced By $100,000

Single-story home with a light-colored exterior, a paved driveway, and lush landscaping at 32 Bayhead Ln, Osprey, FL 34229
View Details 100 Photos
An aerial view showcasing a waterfront community and a homesite with mature trees at 32 Bayhead Ln, Osprey, FL 34229
An aerial view showcasing a waterfront community and a homesite with mature trees at 32 Bayhead Ln, Osprey, FL 34229
An aerial view showcasing a waterfront community and a homesite with mature trees at 32 Bayhead Ln, Osprey, FL 34229
On Market For 59 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2570

  • Year Built

    1993

  • $/SqFt

    $426

This home is a must see. MICHAEL SAUNDERS & COMPANY.

Home For Sale $2,150,000

Beautiful one-story home with lush landscaping and a large lawn at 85 Sugar Mill Dr, Osprey, FL 34229
View Details 68 Photos
Luxury home with a spacious lot and water views at 85 Sugar Mill Dr, Osprey, FL 34229
Luxury home with a large driveway and manicured landscaping at 85 Sugar Mill Dr, Osprey, FL 34229
Inviting pool and spa area with covered patio at 85 Sugar Mill Dr, Osprey, FL 34229
On Market For 67 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    4191

  • Year Built

    1991

  • $/SqFt

    $513

Membership is required and there is NO WAITLIST for GOLF or SOCIAL Membership. GENEROUS PROPERTY.

Viewing HOMES 1 to 50 of 98

Area Stats

These statistics are updated daily from the My Florida Regional MLS. For further analysis or to obtain statistics not shown below please call EasyStreet Realty at (813) 464-9973 and speak with one of our real estate consultants.

Popular Homes

City
Avg Price
Median Price
Available
Distressed
Reduced
Avg DOM
Anna Maria
$3,689,801
$2,850,000
83
0.0%
38.6%
89

Bradenton
$761,738
$600,000
1682
0.7%
55.7%
84

Bradenton Beach
$3,587,530
$2,998,000
29
0.0%
34.5%
129

Cortez
$1,434,944
$1,312,000
18
0.0%
44.4%
77

Ellenton
$586,457
$519,000
47
2.1%
51.1%
74

Englewood
$627,622
$469,000
646
0.6%
55.4%
95

Holmes Beach
$2,774,632
$1,985,000
107
1.9%
39.3%
77

Lakewood Ranch
$966,793
$714,995
480
0.0%
66.5%
101

Longboat Key
$4,142,343
$2,500,000
145
0.7%
39.3%
87

Myakka City
$1,525,167
$837,500
28
0.0%
46.4%
130

Nokomis
$1,022,353
$599,900
439
0.5%
63.8%
110

North Port
$382,242
$364,950
1242
1.1%
56.3%
115

Palmetto
$538,955
$425,000
432
0.9%
64.6%
81

Parrish
$506,552
$439,250
962
0.4%
61.7%
89

Sarasota
$1,376,219
$757,800
2145
0.3%
52.6%
88

Terra Ceia
$1,396,727
$1,195,000
15
6.7%
66.7%
78

Venice
$601,004
$515,000
1214
0.4%
61.1%
95

EasyStreet

Call to Schedule a Showing

(813) 464-9973

(813) 464-9973