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107 Results

Osprey Homes For Sale & Osprey FL Real Estate

Home For Sale $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 83 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 4 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 4 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
Inviting outdoor space features a covered patio with a bar and seating area at 3921 Waypoint Ave, Osprey, FL 34229
Scenic walkway to the water with lush landscaping at 3921 Waypoint Ave, Osprey, FL 34229
On Market For 4 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 $2,395,000

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 6 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    3681

  • Year Built

    1992

  • $/SqFt

    $651

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 $199,000

Reduced By $100,900

Charming yellow home with a pink door, paved driveway, and lush tropical landscaping at 234 Patterson Ave, Osprey, FL 34229
View Details 5 Photos
Charming yellow home with a pink door, well-maintained lawn, and beautiful curb appeal at 234 Patterson Ave, Osprey, FL 34229
Yellow house with pink door, lush landscaping, and a cozy, inviting exterior at 234 Patterson Ave, Osprey, FL 34229
Charming yellow home with palm trees and a whimsical garden display for a tropical feel at 234 Patterson Ave, Osprey, FL 34229
*POTENTIAL GREAT VALUE
On Market For 6 Days

  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1173

  • Year Built

    1979

  • $/SqFt

    $170

Your beach life is about to begin! KELLER WILLIAMS ISLAND LIFE REAL ESTATE.

Pended $1,100,000

Stunning single-story home featuring lush landscaping, mature palm trees, and a paver driveway at 229 Lookout Point Dr, Osprey, FL 34229
View Details 51 Photos
Beautiful front entrance of a home, adorned with tropical landscaping and a paver driveway at 229 Lookout Point Dr, Osprey, FL 34229
Bright living room featuring hardwood floors, neutral decor, and a view of the pool at 229 Lookout Point Dr, Osprey, FL 34229
Open-concept living space with hardwood floors, and seamless flow to kitchen and outdoor area at 229 Lookout Point Dr, Osprey, FL 34229
On Market For 6 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2388

  • Year Built

    2013

  • $/SqFt

    $461

Everything the Florida lifestyle has to offer can be found right here! PREMIER SOTHEBYS INTL REALTY.

Home For Sale $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 8 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
On Market For 9 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 $729,000

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 9 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2058

  • Year Built

    1977

  • $/SqFt

    $354

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 11 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 $375,000

Single-story home with an arched entryway, landscaped yard and a cozy, welcoming feel at 240 Patterson Ave, Osprey, FL 34229
View Details 39 Photos
Single-story home features a clean facade with an attached garage and tidy landscaping at 240 Patterson Ave, Osprey, FL 34229
Well-maintained single-story home with an attached garage and neatly arranged front yard at 240 Patterson Ave, Osprey, FL 34229
Charming single-story home with a well-manicured lawn and inviting curb appeal at 240 Patterson Ave, Osprey, FL 34229
*POTENTIAL GREAT VALUE
On Market For 11 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1608

  • Year Built

    1982

  • $/SqFt

    $233

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 11 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    2310

  • Year Built

    2001

  • $/SqFt

    $418

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

Home For Sale $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 10 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.

Home For Sale $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 9 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 $525,000

Charming single-story home featuring a white picket fence, manicured landscaping, and an attached two-car garage at 544 Meadow Sweet Cir, Osprey, FL 34229
View Details 50 Photos
Inviting entrance featuring double glass doors, decorative wrought iron accents, and a decorative ceramic flower pot at 544 Meadow Sweet Cir, Osprey, FL 34229
Inviting home entrance featuring a secure screen door, number '544', and exterior light fixture at 544 Meadow Sweet Cir, Osprey, FL 34229
Foyer with seating, decorative wall art, and beautiful double doors to let the sun shine in at 544 Meadow Sweet Cir, Osprey, FL 34229
On Market For 13 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1700

  • Year Built

    2001

  • $/SqFt

    $309

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

Home For Sale $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 17 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 18 Days

  • Bedrooms

    6

  • Full Bath(s)

    6

  • Sq. Ft.

    6246

  • Year Built

    1986

  • $/SqFt

    $464

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

Pended $1,800,000

Stately two-story home with a grand entrance, manicured landscaping and verdant surroundings at 916 Macewen Dr, Osprey, FL 34229
View Details 100 Photos
Elegant two-story home with a symmetrical facade, well-maintained lawn and mature trees at 916 Macewen Dr, Osprey, FL 34229
Close-up of the home's front entrance featuring double doors, sidelights and stately columns at 916 Macewen Dr, Osprey, FL 34229
A grand foyer with a staircase, chandelier, high ceilings, and marble floors at 916 Macewen Dr, Osprey, FL 34229
*POTENTIAL GREAT VALUE
On Market For 6 Days

  • Bedrooms

    5

  • Full Bath(s)

    7

  • Sq. Ft.

    5987

  • Year Built

    1991

  • $/SqFt

    $301

With two distinctly unique 18-hole championship golf courses, 12 HAR-TRU tennis courts (4 lighted), croquet and pickle ball courts, a state-of-the art fitness center, fine and casual dining options, and a wealth of social events, The Oaks is truly Sarasota’s premier golf and country club. COLDWELL BANKER REALTY.

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 22 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 $1,695,000

Stunning home with a tile roof, paver driveway, lush landscaping, and serene water views at 402 Walls Way, Osprey, FL 34229
View Details 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 25 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

Expansive aerial view of the property showcasing its lush landscaping and well-maintained surroundings at 826 Oak Briar Ln, Osprey, FL 34229
View Details 67 Photos
Beautiful single-story home featuring a well-manicured lawn and a spacious driveway leading to a two-car garage 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
Inviting screened-in patio with comfortable seating overlooking a private pool and well-kept backyard at 826 Oak Briar Ln, Osprey, FL 34229
On Market For 28 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 30 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 32 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 33 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 34 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 38 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 33 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 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 40 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 40 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 41 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 $700,000

Reduced By $175,000

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
*POTENTIAL GREAT VALUE
On Market For 36 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2887

  • Year Built

    1995

  • $/SqFt

    $242

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 44 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 $875,000

Reduced By $35,000

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 45 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2678

  • Year Built

    2005

  • $/SqFt

    $327

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

Home For Sale $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 46 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 $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 46 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 $1,625,000

Reduced By $50,000

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 51 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3486

  • Year Built

    2017

  • $/SqFt

    $466

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 52 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 55 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 $495,000

Reduced By $70,000

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 59 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1808

  • Year Built

    2003

  • $/SqFt

    $274

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

Home For Sale $2,345,000

Reduced By $50,000

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 60 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2473

  • Year Built

    1985

  • $/SqFt

    $948

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 50 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 63 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2315

  • Year Built

    1972

  • $/SqFt

    $862

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 53 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 13 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 $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 66 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 70 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 $749,000

Reduced By $50,000

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 70 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2540

  • Year Built

    2002

  • $/SqFt

    $295

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 73 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 $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 66 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 $1,049,000

Reduced By $50,000

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 73 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2775

  • Year Built

    2004

  • $/SqFt

    $378

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

Viewing HOMES 1 to 50 of 107

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 386-801-4854 and speak with one of our real estate consultants.

Popular Homes

City
Avg Price
Median Price
Available
Distressed
Reduced
Avg DOM
Anna Maria
$3,698,256
$2,795,000
83
0.0%
43.4%
104

Bradenton
$756,134
$599,999
1713
0.8%
56.8%
85

Bradenton Beach
$3,586,759
$2,998,500
28
0.0%
53.6%
153

Cortez
$1,529,981
$1,424,500
16
0.0%
37.5%
79

Ellenton
$576,190
$485,000
52
1.9%
65.4%
83

Englewood
$650,912
$471,500
688
0.6%
56.4%
94

Holmes Beach
$2,618,469
$1,750,000
122
1.6%
42.6%
83

Lakewood Ranch
$977,125
$725,000
483
0.0%
66.0%
101

Longboat Key
$3,953,529
$2,475,000
139
0.7%
48.9%
97

Myakka City
$1,966,862
$1,175,000
24
0.0%
50.0%
146

Nokomis
$1,026,811
$599,900
435
0.2%
65.3%
109

North Port
$383,566
$359,900
1242
1.2%
60.4%
115

Palmetto
$536,927
$416,990
448
0.9%
64.7%
80

Parrish
$508,917
$440,000
957
0.5%
62.8%
91

Sarasota
$1,386,564
$750,000
2187
0.3%
55.1%
89

Terra Ceia
$1,538,465
$1,195,000
17
5.9%
70.6%
90

Venice
$602,760
$519,000
1203
0.5%
65.3%
99

EasyStreet

Call to Schedule a Showing

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