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Osprey Homes For Sale & Osprey FL Real Estate

Home For Sale $625,000

Charming home features an archway entrance and lush landscaping enhancing the curb appeal at 553 Meadow Sweet Cir, Osprey, FL 34229
View Details 47 Photos
Inviting front yard with mature trees, lush landscaping, and well-maintained lawn at 553 Meadow Sweet Cir, Osprey, FL 34229
Quiet tree-lined street showcases homes with mature landscaping at 553 Meadow Sweet Cir, Osprey, FL 34229
Bright foyer with wood-look flooring, a glass paneled front door, and an orange accent stool at 553 Meadow Sweet Cir, Osprey, FL 34229
On Market Today

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1761

  • Year Built

    2001

  • $/SqFt

    $355

Plus, enjoy access to the community pool and clubhouse for fun and relaxation. MICHAEL SAUNDERS & COMPANY.

Home For Sale $750,000

Charming single-story home boasts a tile roof, well-manicured lawn, and a spacious three-car garage at 463 Park Trace Blvd, Osprey, FL 34229
View Details 60 Photos
Stunning aerial view of a home with pool, screened lanai and lake frontage in a beautiful community at 463 Park Trace Blvd, Osprey, FL 34229
Inviting home entrance features a well-maintained lawn, lush garden beds and covered front entryway at 463 Park Trace Blvd, Osprey, FL 34229
Bright dining room flows into living spaces with a view to the lanai and pool at 463 Park Trace Blvd, Osprey, FL 34229
On Market For 3 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2153

  • Year Built

    2002

  • $/SqFt

    $348

Enjoy the perfect balance of luxury and comfort in a prime location for years to come. PREMIER SOTHEBYS INTL REALTY.

Home For Sale $797,000

Relaxing screened lanai with comfortable seating, outdoor kitchen, and pool overlooking a serene lake view at 521 Habitat Blvd, Osprey, FL 34229
View Details 54 Photos
Charming home featuring a well-maintained lawn, manicured shrubs, and a clay tile roof, offering great curb appeal at 521 Habitat Blvd, Osprey, FL 34229
Beautiful aerial view of a home with a red tile roof, lush landscaping, and a serene lake at 521 Habitat Blvd, Osprey, FL 34229
Gorgeous pool and spa area enclosed with a screen, offering lake views at 521 Habitat Blvd, Osprey, FL 34229
On Market For 3 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2266

  • Year Built

    2003

  • $/SqFt

    $352

Living here is not just a lifestyle, it’s an artful experience. PREMIER SOTHEBYS INTL REALTY.

Home For Sale $3,750,000

Stunning aerial view of a waterfront home with a private pool and beautiful coastal landscape near the ocean at 1042 N Casey Key Rd, Osprey, FL 34229
View Details 71 Photos
Charming two-story home featuring a lush landscaped front yard, a two-car garage, and a cozy covered porch at 1042 N Casey Key Rd, Osprey, FL 34229
Expansive aerial view of the meticulously maintained property with a screened-in pool and lush tropical landscaping at 1042 N Casey Key Rd, Osprey, FL 34229
Beautiful two-story home featuring a well-manicured lawn and mature tropical landscaping with lush palm trees at 1042 N Casey Key Rd, Osprey, FL 34229
On Market For 12 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    4781

  • Year Built

    1995

  • $/SqFt

    $784

A truly special home....ready to begin its next chapter. COLDWELL BANKER REALTY.

Home For Sale $999,000

Beautiful aerial view of a modern home with a circular driveway, well-manicured landscaping, and a gray roof at 238 Lookout Point Dr, Osprey, FL 34229
View Details 38 Photos
Charming home featuring an American flag, stone accents, mature palms, and a lush, landscaped front yard at 238 Lookout Point Dr, Osprey, FL 34229
Paver driveway leading to a home with a two-car garage, landscaped yard, and modern architecture at 238 Lookout Point Dr, Osprey, FL 34229
Welcoming front entryway with double doors, accent chairs, and a brick paver walkway with a custom design at 238 Lookout Point Dr, Osprey, FL 34229
On Market For 12 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2676

  • Year Built

    1981

  • $/SqFt

    $373

Whether you're an avid boater, a tennis enthusiast, or someone who simply loves the charm of coastal living, this community has something extraordinary to offer. COLDWELL BANKER REALTY.

Home For Sale $745,000

Charming single-story home with a well-manicured lawn and mature trees shading the entrance at 104 Park Trace Blvd, Osprey, FL 34229
View Details 23 Photos
Enjoy a refreshing swim in this screened-in pool surrounded by lush greenery and lounge chairs at 104 Park Trace Blvd, Osprey, FL 34229
Beautiful home featuring a manicured lawn, mature trees, and a brick-lined driveway at 104 Park Trace Blvd, Osprey, FL 34229
Elegant home entrance with a brick pathway, arched doorway, and well-maintained landscaping at 104 Park Trace Blvd, Osprey, FL 34229
On Market For 12 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2557

  • Year Built

    2002

  • $/SqFt

    $291

Don’t miss this perfect blend of elegance and Florida lifestyle in Osprey! Schedule your tour today. KW COASTAL LIVING III.

Home For Sale $669,000

Charming single-story home with a well-manicured lawn, beautiful landscaping, and welcoming covered front porch at 750 Anna Hope Ln, Osprey, FL 34229
View Details 41 Photos
Inviting single-story home with lush landscaping, a well-manicured lawn, and charming covered entryway at 750 Anna Hope Ln, Osprey, FL 34229
Welcoming front porch with seating area, and a view of the front door with sidelight, transom, and sidelight window at 750 Anna Hope Ln, Osprey, FL 34229
Elegant dining room featuring a glass table, striped chairs, chandelier, and natural light from the large window at 750 Anna Hope Ln, Osprey, FL 34229
On Market For 12 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2135

  • Year Built

    2000

  • $/SqFt

    $313

Additionally, magnificent white sandy beaches, vibrant arts and culture scenes, shopping, and the incredible Oscar Scherer State Park are all within easy reach. COLDWELL BANKER REALTY.

Home For Sale $597,000

Charming single-story home boasts a well-manicured lawn, brick driveway and a tile roof at 1313 Thornapple Dr, Osprey, FL 34229
View Details 40 Photos
Charming single-story home boasts a well-manicured lawn, brick driveway and a tile roof at 1313 Thornapple Dr, Osprey, FL 34229
Bright foyer with neutral walls, decor, tile flooring, and a view into the living area at 1313 Thornapple Dr, Osprey, FL 34229
Bright foyer with neutral walls, decor, tile flooring, and a view of the front door at 1313 Thornapple Dr, Osprey, FL 34229
On Market For 12 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2082

  • Year Built

    2003

  • $/SqFt

    $287

It's easy to perfect the art of living when you live within a work of art. PREMIER SOTHEBYS INTL REALTY.

Home For Sale $3,900,000

Stunning waterfront home with lush landscaping, beautiful water views, and a grand, columned entrance at 112 Osprey Point Dr, Osprey, FL 34229
View Details 76 Photos
Elegant estate with stately columns, a private balcony, and meticulously manicured landscaping at 112 Osprey Point Dr, Osprey, FL 34229
Waterfront estate with an amazing water view, lush landscaping, and a serene pond nearby at 112 Osprey Point Dr, Osprey, FL 34229
Aerial view of waterfront estate with beautiful landscaping, private dock, and access to open water at 112 Osprey Point Dr, Osprey, FL 34229
*IS BANK OWNED
On Market For 13 Days

  • Bedrooms

    4

  • Full Bath(s)

    5

  • Sq. Ft.

    8635

  • Year Built

    1989

  • $/SqFt

    $452

This exceptional property is ready for your private tour at your convenience. KARA MONEY LLC.

Home For Sale $679,600

Stunning single-Gathering home showcasing lush landscaping and a charming exterior at 622 Pine Ranch East Rd, Osprey, FL 34229
View Details 45 Photos
Stunning aerial view of the property showcasing the community, nearby golf course, and ocean views at 622 Pine Ranch East Rd, Osprey, FL 34229
Inviting single-Gathering home with well-maintained landscaping and a two-car garage at 622 Pine Ranch East Rd, Osprey, FL 34229
An aerial view shows the house with a brown roof and screened in pool, surrounded by lush landscaping at 622 Pine Ranch East Rd, Osprey, FL 34229
On Market For 17 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2302

  • Year Built

    1995

  • $/SqFt

    $295

Bay Oaks Estates - If it is time for shopping and dining visit St. Armands Circle and also Venice downtown where you might just be treated to one of our many festivals or go north to Downtown Sarasota where there is so much more to explore. PARADISE EXCLUSIVE INC.

Home For Sale $997,000

Charming single-story home with a well-manicured lawn, mature tree, and white exterior paint at 172 Sea Anchor Dr, Osprey, FL 34229
View Details 49 Photos
Inviting front entrance with bright blue door, manicured landscaping, and freshly cut green grass at 172 Sea Anchor Dr, Osprey, FL 34229
Open-concept living room featuring stylish gray furniture and elegant white marble flooring at 172 Sea Anchor Dr, Osprey, FL 34229
Bright and airy living room with a contemporary gray sofa, marble floors, and kitchen views at 172 Sea Anchor Dr, Osprey, FL 34229
On Market For 17 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2283

  • Year Built

    1977

  • $/SqFt

    $437

Southbay Yacht & Racquet Club - Come live the true Florida lifestyle! GOLF & BAY PROPERTIES LLC.

Home For Sale $599,000

Charming single-story home featuring light blue shutters, a well-manicured lawn, and a concrete driveway at 104 Shoreland Dr, Osprey, FL 34229
View Details 39 Photos
Charming single-story home featuring light blue shutters, a well-manicured lawn, and a concrete driveway at 104 Shoreland Dr, Osprey, FL 34229
Inviting entryway with light wood-look floors, lots of natural light, decorative mirror and accent table at 104 Shoreland Dr, Osprey, FL 34229
Spacious living room featuring a stone fireplace, plush sectional sofa, and sliding glass doors at 104 Shoreland Dr, Osprey, FL 34229
On Market For 23 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2363

  • Year Built

    1956

  • $/SqFt

    $253

Towns End Shores - Don't wait to schedule your showing today! OAKSTRAND REALTY.

Home For Sale $549,000

Charming single-story home with a well-manicured lawn, complemented by lush tropical landscaping and an attached two-car garage at 1363 New Forest Ln, Osprey, FL 34229
View Details 24 Photos
Spacious living room featuring tile floors, a tray ceiling, and sliding glass doors leading to an outdoor patio at 1363 New Forest Ln, Osprey, FL 34229
Inviting foyer with tile flooring, a stylish light fixture, and a view into adjacent rooms, enhancing the home's openness at 1363 New Forest Ln, Osprey, FL 34229
Neutral bedroom with carpet flooring, a ceiling fan, and a window offering natural light and views of the outdoors at 1363 New Forest Ln, Osprey, FL 34229
On Market For 23 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1738

  • Year Built

    2002

  • $/SqFt

    $316

Rivendell The Woodlands - Rivendell, a picturesque community known for its extensive green spaces, parks and 24 serene lakes! RE/MAX PLATINUM.

Home For Sale $815,000

Stunning single story home featuring a red tile roof, neutral paint, manicured landscaping and a circular driveway at 901 Reflection Way, Osprey, FL 34229
View Details 38 Photos
Charming home featuring lush lawn, mature trees, decorative landscaping and a brick-lined driveway and walkway at 901 Reflection Way, Osprey, FL 34229
Aerial view of a single story home with a red tile roof, circular driveway, mature trees and lush landscaping at 901 Reflection Way, Osprey, FL 34229
Inviting single story home with a red tile roof, neutral paint, manicured landscaping and a circular driveway at 901 Reflection Way, Osprey, FL 34229
On Market For 25 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2443

  • Year Built

    2002

  • $/SqFt

    $334

Don’t miss the opportunity to own this exceptional home in one of the area's most desirable communities! GENEROUS PROPERTY.

Home For Sale $1,595,000

Charming one story home with brick driveway, lush green yard, and mature trees at 228 Saint James Park, Osprey, FL 34229
View Details 100 Photos
Aerial view of home on the golf course near the water, with serene landscaping at 228 Saint James Park, Osprey, FL 34229
Beautiful aerial view of home on golf course, surrounded by lush landscaping and water views at 228 Saint James Park, Osprey, FL 34229
Beautiful aerial view of home, with enclosed pool, near the water and surrounded by golf course at 228 Saint James Park, Osprey, FL 34229
On Market For 29 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2425

  • Year Built

    1997

  • $/SqFt

    $658

And The Oaks Club has been designated a Platinum Club of America and an Emerald Club, signifying its standing among the finest country clubs in Florida and the nation. Schedule a showing today! MICHAEL SAUNDERS & COMPANY.

Home For Sale $1,000,000

Charming single-story home with a well-manicured lawn, mature landscaping, and a three-car garage at 1085 Mallard Marsh Dr, Osprey, FL 34229
View Details 72 Photos
Stunning lakefront property featuring a tile roof, well-manicured lawn and three-car garage at 1085 Mallard Marsh Dr, Osprey, FL 34229
Aerial view showcasing waterfront property with lush landscaping and stunning lake views at 1085 Mallard Marsh Dr, Osprey, FL 34229
Inviting front entrance with pillars, a decorative door, and lush landscaping with palm tree at 1085 Mallard Marsh Dr, Osprey, FL 34229
On Market For 29 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3011

  • Year Built

    2001

  • $/SqFt

    $332

A generous three-car garage adds to the home's appeal. MICHAEL SAUNDERS & COMPANY.

Home For Sale $525,000

An aerial view of a single-Gathering home surrounded by lush trees near the bay area at 519 Bayview Ave, Osprey, FL 34229
View Details 63 Photos
Charming single-story home featuring a two-car garage, well-maintained landscaping, and a inviting walkway at 519 Bayview Ave, Osprey, FL 34229
Canal with multiple boats docked, surrounded by lush greenery and a view of a large waterfront home at 519 Bayview Ave, Osprey, FL 34229
Side view features an outdoor shed, spacious driveway, and mature landscaping in a well-maintained yard at 519 Bayview Ave, Osprey, FL 34229
On Market For 31 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1550

  • Year Built

    1987

  • $/SqFt

    $339

Overall, this property presents an ideal opportunity to immerse oneself in the coastal charm and tranquility of the area, with its well-maintained exterior, spacious layout, and wealth of amenities. COLDWELL BANKER REALTY.

Pended $1,299,000

Stunning two-story home with lush landscaping and a three-car garage, nestled among mature trees at 223 Saint James Park, Osprey, FL 34229
View Details 88 Photos
Beautiful home exterior with mature landscaping, a brick driveway and an attached three-car garage at 223 Saint James Park, Osprey, FL 34229
Inviting front porch featuring classic columns, brick flooring, and an elegant front door at 223 Saint James Park, Osprey, FL 34229
Spacious covered porch with brick flooring and views of manicured landscaping at 223 Saint James Park, Osprey, FL 34229
On Market For 36 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    3321

  • Year Built

    1991

  • $/SqFt

    $391

The Oaks is proud to be a Platinum Club of America and holds a renowned 5-Star rating. RE/MAX ALLIANCE GROUP.

Home For Sale $699,000

Attractive single-story home boasts a well-manicured lawn, mature landscaping, and inviting curb appeal at 241 Willow Bend Way, Osprey, FL 34229
View Details 64 Photos
Charming single-story home features a well-manicured lawn and mature landscaping, creating inviting curb appeal at 241 Willow Bend Way, Osprey, FL 34229
Beautiful one-story home with well-maintained landscaping, a tile roof, and lush greenery, providing a welcoming curb appeal at 241 Willow Bend Way, Osprey, FL 34229
Attractive one-story home with well-maintained landscaping, a tile roof, and lush greenery, providing a welcoming curb appeal at 241 Willow Bend Way, Osprey, FL 34229
On Market For 37 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2298

  • Year Built

    2000

  • $/SqFt

    $304

Additional highlights include a versatile den ideal for a home office or guest space. MICHAEL SAUNDERS & COMPANY.

Home For Sale $1,195,000

Expansive aerial view of the community with waterfront access and lush landscaping at 3921 Waypoint Ave, Osprey, FL 34229
View Details 80 Photos
Charming single-story home boasts lush landscaping, paver driveway, and tile roof at 3921 Waypoint Ave, Osprey, FL 34229
Screened-in pool area with a beautiful in-ground pool, jacuzzi, and lovely brick patio surrounded by green landscaping at 3921 Waypoint Ave, Osprey, FL 34229
This outdoor space is perfect for entertaining, offering a kitchen, bar, and outdoor seating area with ceiling fans at 3921 Waypoint Ave, Osprey, FL 34229
On Market For 38 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2316

  • Year Built

    2016

  • $/SqFt

    $516

Watch Both The Virtual Tour & The 360 Photo Tour - Don'T Delay - Schedule A Showing Today!! ! WHITE SANDS REALTY GROUP FL.

Home For Sale $2,390,000

Reduced By $5,000

Beautiful single-story home with lush landscaping, mature shade trees, and a circular driveway at 600 Eagle Watch Ln, Osprey, FL 34229
View Details 85 Photos
Elegant front entryway with arched windows and double doors flanked by white columns at 600 Eagle Watch Ln, Osprey, FL 34229
Bright foyer featuring double doors with decorative glass and light hardwood floors at 600 Eagle Watch Ln, Osprey, FL 34229
Sunlit bedroom with hardwood floors, wood shuttered windows and crown molding at 600 Eagle Watch Ln, Osprey, FL 34229
On Market For 39 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    3681

  • Year Built

    1992

  • $/SqFt

    $649

This is a rare chance to step into a like-new home on one of the premier lots in Southwest Sarasota’s most established and visually striking neighborhoods. COLDWELL BANKER REALTY.

Pended $1,200,000

Inviting single-story home featuring mature landscaping, a well manicured lawn, and a neutral color palette at 142 Dory Ln, Osprey, FL 34229
View Details 48 Photos
Welcoming single-story home featuring mature landscaping, a well manicured lawn, and a neutral color palette at 142 Dory Ln, Osprey, FL 34229
Charming front entrance with decorative landscaping leading to the front door and a stone tile walkway at 142 Dory Ln, Osprey, FL 34229
Inviting foyer with tiled floors, high ceilings, statement blue accent wall, and a decorative wood double door at 142 Dory Ln, Osprey, FL 34229
On Market For 41 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2531

  • Year Built

    1984

  • $/SqFt

    $474

Don't miss your chance to own a piece of Paradise! Professional photos coming soon. GOLF & BAY PROPERTIES LLC.

Home For Sale $2,500,000

Elegant two-story home featuring a lush green lawn, manicured landscaping, and a stately entrance at 340 Osprey Point Dr, Osprey, FL 34229
View Details 72 Photos
Close-up view of a home's entrance featuring columns, a double door, manicured shrubs and landscaping at 340 Osprey Point Dr, Osprey, FL 34229
Inviting living room with a large white sectional, custom cabinets, and an open floor plan at 340 Osprey Point Dr, Osprey, FL 34229
Open-concept living space with a fireplace, a TV, and custom cabinets with a beverage bar at 340 Osprey Point Dr, Osprey, FL 34229
*POTENTIAL GREAT VALUE
On Market For 42 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    6001

  • Year Built

    1998

  • $/SqFt

    $417

Don’t miss your chance to own this exceptional estate—schedule your private tour today and experience the luxury of life at The Oaks Bayside. RE/MAX ALLIANCE GROUP.

Home For Sale $715,000

Reduced By $14,000

Charming single-story home with a well-maintained lawn and inviting curb appeal, nestled beneath lush trees at 110 Pine Ave, Osprey, FL 34229
View Details 11 Photos
Expansive living area featuring neutral walls and tile flooring, offering a blank canvas for personalization at 110 Pine Ave, Osprey, FL 34229
Sunlit living space showcases modern flooring and a convenient breakfast bar, ideal for entertaining and daily living at 110 Pine Ave, Osprey, FL 34229
Elegant bathroom featuring a double vanity with contemporary fixtures, framed mirrors, and stylish lighting at 110 Pine Ave, Osprey, FL 34229
On Market For 42 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2058

  • Year Built

    1977

  • $/SqFt

    $347

Whether you're looking for a family home, a. vacation retreat, or a profitable rental property BRIGHT REALTY.

Pended $989,000

Expansive property with a screened pool, set amidst lush greenery and serene lake views at 336 Pine Ranch East Rd, Osprey, FL 34229
View Details 63 Photos
Charming single-story home with arched windows, manicured lawn, and inviting entryway at 336 Pine Ranch East Rd, Osprey, FL 34229
Inviting single-story home features a well-kept lawn and an attractive entryway at 336 Pine Ranch East Rd, Osprey, FL 34229
Lovely single-story home nestled among mature trees, boasting a spacious front lawn at 336 Pine Ranch East Rd, Osprey, FL 34229
On Market For 44 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2705

  • Year Built

    1989

  • $/SqFt

    $366

A property this rarely available—with unparalleled privacy, natural beauty, and proximity to top schools and beaches—won’t last long. Schedule your showing today! PREFERRED SHORE LLC.

Home For Sale $367,000

Reduced By $8,000

Charming single-story home featuring a one-car garage and a beautifully landscaped front yard with colorful flowers at 240 Patterson Ave, Osprey, FL 34229
View Details 38 Photos
Delightful home exterior with a manicured garden, featuring flowering shrubs and a stepping stone walkway to the entryway at 240 Patterson Ave, Osprey, FL 34229
Inviting covered porch with tiled flooring, decorative plants, and a bright orange front door, offering a warm welcome at 240 Patterson Ave, Osprey, FL 34229
Charming front porch with plants, white gravel, and a red door, creating an inviting entrance at 240 Patterson Ave, Osprey, FL 34229
On Market For 44 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1360

  • Year Built

    1982

  • $/SqFt

    $270

Don’t miss this opportunity to enjoy Florida living at its best with space to store your toys and easy access to the area's top attractions. COLDWELL BANKER REALTY.

Home For Sale $965,000

Charming home featuring a paved driveway, manicured landscaping, and exterior lighting at 13 Bayhead Ln, Osprey, FL 34229
View Details 62 Photos
Relaxing pool area with screened enclosure offering serene views of nature at 13 Bayhead Ln, Osprey, FL 34229
Bright, all-white kitchen with marble countertops and tiled floor at 13 Bayhead Ln, Osprey, FL 34229
Elegant bathroom with double vanity, granite countertop and a walk-in shower at 13 Bayhead Ln, Osprey, FL 34229
On Market For 44 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    2310

  • Year Built

    2001

  • $/SqFt

    $418

**PLEASE ENJOY VIEWING the 3D VIRTUAL TOUR** GENEROUS PROPERTY.

Pended $659,000

Stunning aerial view of a home with a tile roof, paver driveway, lush landscaping, and a serene lake backdrop at 519 Habitat Blvd, Osprey, FL 34229
View Details 52 Photos
Charming single-story home featuring manicured landscaping, a paver driveway, and a welcoming entrance with a blue door at 519 Habitat Blvd, Osprey, FL 34229
Beautiful aerial view showcasing the home's location near a lake, surrounded by lush greenery and well-maintained landscaping at 519 Habitat Blvd, Osprey, FL 34229
Expansive aerial view of a community with homes nestled around a scenic lake, showcasing the property's prime location at 519 Habitat Blvd, Osprey, FL 34229
On Market For 39 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2234

  • Year Built

    2003

  • $/SqFt

    $295

Living in this work of art makes perfecting the art of living effortless. PREMIER SOTHEBYS INTL REALTY.

Pended $1,100,000

Charming single-story home with lush landscaping, including vibrant flowers and mature trees, under a sunny sky at 284 Lookout Point Dr, Osprey, FL 34229
View Details 91 Photos
Aerial view of a home showcasing its terracotta roof, lush landscaping, and well-maintained grounds in a neighborhood at 284 Lookout Point Dr, Osprey, FL 34229
A beautiful home showcasing its terracotta roof, screened-in pool, and well-manicured lawn in a tropical setting at 284 Lookout Point Dr, Osprey, FL 34229
Aerial view of a screened-in pool and spa combo surrounded by a brick patio and lush greenery at 284 Lookout Point Dr, Osprey, FL 34229
On Market For 32 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2909

  • Year Built

    1986

  • $/SqFt

    $378

Southbay Yacht & Racquet Club - A very social and friendly neighborhood or private if you like. ROYAL PALM REALTY.

Pended $1,235,000

Stunning aerial view of a home near a marina, boasting lush landscaping and a pristine tile roof at 327 Sea Anchor Dr, Osprey, FL 34229
View Details 83 Photos
Charming single-story home featuring a brick driveway, mature landscaping, and a tile roof at 327 Sea Anchor Dr, Osprey, FL 34229
Inviting living room with a fireplace, colorful rug, and sliding doors to the outdoor living space at 327 Sea Anchor Dr, Osprey, FL 34229
Relaxing outdoor living area with comfortable seating overlooking the pool and lush landscaping at 327 Sea Anchor Dr, Osprey, FL 34229
On Market For 50 Days

  • Bedrooms

    2

  • Full Bath(s)

    3

  • Sq. Ft.

    2521

  • Year Built

    1981

  • $/SqFt

    $490

Don't miss your opportunity to make it yours! PREMIER SOTHEBYS INTL REALTY.

Home For Sale $2,900,000

Stately home with lush landscaping, circular drive, and elegant architectural details at twilight at 236 Saint James Park, Osprey, FL 34229
View Details 88 Photos
Tranquil backyard featuring a private pool, spa, and an outdoor dining area perfect for entertaining at 236 Saint James Park, Osprey, FL 34229
Elegant foyer with marble floors, a grand chandelier, and a view of the staircase at 236 Saint James Park, Osprey, FL 34229
Spacious main bedroom with a four-poster bed, sitting area, and large windows with natural light at 236 Saint James Park, Osprey, FL 34229
On Market For 51 Days

  • Bedrooms

    6

  • Full Bath(s)

    6

  • Sq. Ft.

    6246

  • Year Built

    1986

  • $/SqFt

    $464

Membership at The Oaks is required. MICHAEL SAUNDERS & COMPANY.

Home For Sale $5,300,000

Elegant home exterior boasts manicured landscaping, striking columns, and a welcoming double door entrance at 101 Osprey Point Dr, Osprey, FL 34229
View Details 37 Photos
Beautiful home featuring a covered entrance, manicured shrubs, and symmetrical design elements at 101 Osprey Point Dr, Osprey, FL 34229
Charming home showcasing a columned entrance, well-maintained landscaping, and classic architectural details at 101 Osprey Point Dr, Osprey, FL 34229
Inviting home with a covered entrance, shutters, manicured shrubs, and meticulously kept grounds at 101 Osprey Point Dr, Osprey, FL 34229
On Market For 55 Days

  • Bedrooms

    4

  • Full Bath(s)

    5

  • Sq. Ft.

    5087

  • Year Built

    1985

  • $/SqFt

    $1,042

Club membership is required with homeownership. COLDWELL BANKER REALTY.

Home For Sale $1,650,000

Reduced By $45,000

Stunning home with a tile roof, paver driveway, lush landscaping, and serene water views at 402 Walls Way, Osprey, FL 34229
View Details 79 Photos
Beautiful home featuring a brick driveway and an attached three-car garage 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
Inviting outdoor patio features brick pavers, a dining area, and a view of the pool surrounded by lush landscaping at 402 Walls Way, Osprey, FL 34229
On Market For 58 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3464

  • Year Built

    2014

  • $/SqFt

    $476

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 $649,000

Reduced By $10,000

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 63 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2130

  • Year Built

    1978

  • $/SqFt

    $305

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
On Market For 65 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3321

  • Year Built

    2002

  • $/SqFt

    $331

Buyers are encouraged to verify all information independently. RE/MAX ALLIANCE GROUP.

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 67 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 71 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 66 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 $2,795,000

Reduced By $200,000

Stunning home exterior featuring lush landscaping, elegant design, and inviting entrance at 49 Osprey Point Dr, Osprey, FL 34229
View Details 95 Photos
Bright living room with high ceilings, fireplace, and comfortable seating areas at 49 Osprey Point Dr, Osprey, FL 34229
Spacious living room with stylish decor, modern design, and comfortable seating 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 73 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3953

  • Year Built

    1989

  • $/SqFt

    $707

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

Charming home featuring a landscaped front yard, brick accents, and a welcoming red front door at sunset at 201 Eaglenook Way, Osprey, FL 34229
View Details 88 Photos
Aerial view of home featuring a screened-in pool surrounded by lush, mature landscaping 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
Pine Ranch community sign surrounded by trees and landscaping at 201 Eaglenook Way, Osprey, FL 34229
On Market For 73 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 $1,100,000

Reduced By $290,000

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 74 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3938

  • Year Built

    2002

  • $/SqFt

    $279

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

Pended $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 75 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.

Pended $799,000

Reduced By $111,000

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 64 Photos
Paver patio and lush landscaping overlooking the serene water view creates a relaxing outdoor space at 608 Crane Prairie Way, Osprey, FL 34229
Beautiful aerial view of several homes backing onto a tranquil pond surrounded by lush greenery at 608 Crane Prairie Way, Osprey, FL 34229
Detailed floor plan illustrating layout of bedrooms, bathrooms, living areas, and outdoor spaces at 608 Crane Prairie Way, Osprey, FL 34229
On Market For 78 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2678

  • Year Built

    2005

  • $/SqFt

    $298

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

Pended $585,000

Reduced By $40,000

Charming single-story home featuring a well-manicured lawn, mature landscaping, and a long driveway at 221 Sorrento Dr, Osprey, FL 34229
View Details 62 Photos
Charming single-story home featuring a well-manicured lawn, mature landscaping, and a front yard at 221 Sorrento Dr, Osprey, FL 34229
Inviting front porch with a blue door, featuring tile flooring and cozy seating for outdoor relaxation at 221 Sorrento Dr, Osprey, FL 34229
Charming front porch with tile flooring and a cozy bench for outdoor relaxation at 221 Sorrento Dr, Osprey, FL 34229
On Market For 79 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1935

  • Year Built

    1984

  • $/SqFt

    $302

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 $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 88 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 $2,100,000

Reduced By $295,000

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 94 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2473

  • Year Built

    1985

  • $/SqFt

    $849

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

Home For Sale $1,899,000

Reduced By $96,000

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 96 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2315

  • Year Built

    1972

  • $/SqFt

    $820

and is home to top-rated beaches, restaurants, cycling trails, county and state parks and local airports. Dock application is in process. 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 86 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 $699,900

Reduced By $99,100

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 89 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2513

  • Year Built

    1987

  • $/SqFt

    $279

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 103 Days

  • Bedrooms

    3

  • Full Bath(s)

    4

  • Sq. Ft.

    3699

  • Year Built

    1992

  • $/SqFt

    $460

Club membership is required with homeownership. COLDWELL BANKER REALTY.

Viewing HOMES 1 to 50 of 90

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 407-252-3959 and speak with one of our real estate consultants.

Popular Homes

City
Avg Price
Median Price
Available
Distressed
Reduced
Avg DOM
Anna Maria
$3,931,079
$3,125,000
78
0.0%
46.2%
110

Bradenton
$755,359
$599,900
1684
0.7%
58.3%
88

Bradenton Beach
$3,486,639
$2,895,000
28
0.0%
57.1%
143

Cortez
$1,504,585
$1,497,000
20
0.0%
40.0%
79

Ellenton
$563,332
$509,450
58
1.7%
63.8%
77

Englewood
$676,410
$475,000
655
0.8%
61.4%
106

Holmes Beach
$2,878,568
$1,950,000
124
1.6%
46.0%
96

Lakewood Ranch
$973,508
$701,265
466
0.0%
69.1%
108

Longboat Key
$3,973,265
$2,495,000
143
0.7%
53.8%
117

Myakka City
$1,940,033
$1,393,000
33
0.0%
45.5%
118

Nokomis
$1,085,100
$599,000
409
0.2%
63.6%
115

North Port
$381,707
$359,900
1150
1.1%
60.9%
124

Palmetto
$563,425
$416,990
453
0.9%
66.9%
79

Parrish
$508,523
$444,900
1033
0.8%
60.5%
89

Sarasota
$1,451,221
$755,470
2136
0.3%
58.8%
94

Terra Ceia
$1,552,556
$1,092,500
16
6.2%
68.8%
117

Venice
$594,144
$515,000
1148
0.4%
65.6%
106

EasyStreet

Call to Schedule a Showing

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