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Osprey Homes For Sale & Osprey FL Real Estate

Home For Sale $1,220,000

View 3933 Waypoint Ave Osprey FL
View Details 52 Photos
View 3933 Waypoint Ave Osprey FL
View 3933 Waypoint Ave Osprey FL
View 3933 Waypoint Ave Osprey FL
On Market Today

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2391

  • Year Built

    2016

  • $/SqFt

    $510

Don’t miss out on this rare opportunity to experience Sarasota living at its finest! MLS#A4615178. PREMIER SOTHEBYS INTL REALTY.

Home For Sale $939,000

View 637 Crane Prairie Way Osprey FL
View Details 53 Photos
View 637 Crane Prairie Way Osprey FL
View 637 Crane Prairie Way Osprey FL
View 637 Crane Prairie Way Osprey FL
On Market For 4 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2504

  • Year Built

    2004

  • $/SqFt

    $375

Embrace everyday luxury and adventure in Osprey's premier community of Willowbend – your slice of paradise awaits. MLS#N6133515. CENTURY 21 SCHMIDT REAL ESTATE.

Home For Sale $759,000

View 463 Park Trace Blvd Osprey FL
View Details 64 Photos
View 463 Park Trace Blvd Osprey FL
View 463 Park Trace Blvd Osprey FL
View 463 Park Trace Blvd Osprey FL
On Market For 4 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2153

  • Year Built

    2002

  • $/SqFt

    $353

Priced to sell, this home is a must-see. Schedule your private showing today! MLS#A4614408. KELLER WILLIAMS ISLAND LIFE REAL ESTATE.

Home For Sale $650,000

View 825 Oak Pond Dr Osprey FL
View Details 63 Photos
View 825 Oak Pond Dr Osprey FL
View 825 Oak Pond Dr Osprey FL
View 825 Oak Pond Dr Osprey FL
On Market For 9 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2229

  • Year Built

    1996

  • $/SqFt

    $292

**Click on Virtual Tour 1 For a 3D Tour** MLS#N6133406. ENGEL & VOELKERS VENICE DOWNTOWN.

Home For Sale $1,895,000

View Details 58 Photos
On Market For 12 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3464

  • Year Built

    2014

  • $/SqFt

    $547

Membership is required and there is NO WAITLIST for GOLF or SOCIAL Membership. **ENJOY THE 3D VIRTUAL TOUR** MLS#A4613147. GENEROUS PROPERTY.

Home For Sale $600,000

View Details 39 Photos
On Market For 14 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1867

  • Year Built

    1996

  • $/SqFt

    $321

Centrally located, this home offers convenient access to the area's picturesque gulf beaches, A-rated schools, the scenic Legacy Trail, Oscar Scherer State Park, and an abundance of shopping, dining, and entertainment options. MLS#A4611341. KELLER WILLIAMS CLASSIC GROUP.

Home For Sale $950,000

View Details 49 Photos
On Market For 15 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2513

  • Year Built

    1987

  • $/SqFt

    $378

Southbay Yacht & Racquet Club - Schedule your private tour today and experience firsthand the exceptional living this home offers. MLS#A4612015. COLDWELL BANKER SARASOTA CENT..

Pended $1,280,000

View Details 1 Photo
On Market For 23 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    3048

  • Year Built

    1996

  • $/SqFt

    $420

Experience luxury and tranquility in this exquisite home in The Oaks Clubside. MLS#A4612348. KELLER WILLIAMS ON THE WATER S.

Home For Sale $1,100,000

View Details 51 Photos
On Market For 25 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3060

  • Year Built

    2002

  • $/SqFt

    $359

Park Trace Estates - A treasured lifestyle awaits you & yours, right here, right now!! ! MLS#N6133208. BRIGHT REALTY.

Home For Sale $1,100,000

Reduced By $70,000
View Details 31 Photos
On Market For 32 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2928

  • Year Built

    2002

  • $/SqFt

    $376

Rivendell The Woodlands - Award winning Pine View High School is within walking distance and was voted the #1 High School in the entire state of Florida!! ! MLS#N6133115. RESULTS REALTY GROUP LLC.

Home For Sale $3,350,000

Reduced By $150,000
View Details 89 Photos
*POTENTIAL GREAT VALUE
On Market For 33 Days

  • Bedrooms

    5

  • Full Bath(s)

    6

  • Sq. Ft.

    6863

  • Year Built

    1992

  • $/SqFt

    $488

Schedule a viewing today and step into a lifestyle defined by comfort, elegance, and unparalleled beauty. MLS#A4611882. WHITE SANDS REALTY GROUP FL.

Pended $1,900,000

View Details 100 Photos
On Market For 36 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    4368

  • Year Built

    1998

  • $/SqFt

    $435

Located in south Sarasota, the community is minutes from nationally ranked Pine View School, and close to the Legacy Bike Trail, world renowned area beaches and all the shopping, dining and cultural offerings of downtown Sarasota. MLS#A4610759. COLDWELL BANKER REALTY.

Home For Sale $1,795,000

View Details 73 Photos
On Market For 36 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    4001

  • Year Built

    1983

  • $/SqFt

    $449

Call now to schedule a private showing! MLS#A4611113. KELLER WILLIAMS ON THE WATER S.

Home For Sale $650,000

Reduced By $35,000
View Details 31 Photos
On Market For 35 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2102

  • Year Built

    2002

  • $/SqFt

    $309

Rivendell The Woodlands - Culturally rich downtown Sarasota and charming Venice are moments away along with many public Gulf beaches. MLS#A4611383. RE/MAX ALLIANCE GROUP.

Pended $550,000

View Details 56 Photos
*POTENTIAL GREAT VALUE
On Market For 37 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2204

  • Year Built

    2002

  • $/SqFt

    $250

Rivendell The Woodlands - This is the lifestyle that you expect from living on the Gulf Coast. MLS#A4609381. REALTY BY DESIGN LLC.

Home For Sale $865,000

View Details 40 Photos
On Market For 38 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2358

  • Year Built

    2001

  • $/SqFt

    $367

Membership is required and available. **MUST SEE! ** MLS#A4611066. COLDWELL BANKER REALTY.

Home For Sale $962,500

View Details 78 Photos
On Market For 43 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2176

  • Year Built

    1997

  • $/SqFt

    $442

Don’t miss your chance to explore this exclusive offering—schedule your private showing today! MLS#A4610560. FINE PROPERTIES.

Home For Sale $1,549,000

View Details 100 Photos
*POTENTIAL GREAT VALUE
On Market For 45 Days

  • Bedrooms

    4

  • Full Bath(s)

    5

  • Sq. Ft.

    4406

  • Year Built

    1989

  • $/SqFt

    $352

The Oaks has two 18-hole championship golf courses, 12 HAR-TRU tennis courts maintained to tournament standards, 4 of which are lighted, bocce and pickleball courts, a junior Olympic community pool, and a wide variety of dining, recreational and social offerings. MLS#A4610414. COLDWELL BANKER REALTY.

Home For Sale $6,500,000

View Details 38 Photos
On Market For 48 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    3086

  • Year Built

    1916

  • $/SqFt

    $2,106

The allure of this locale is undeniable, as Casey Key Road was recently acclaimed as the most impressive street nationwide, underscoring the unparalleled status of this magical barrier island. MLS#N6132859. AYERS AND ASSOCIATES REAL ESTATE.

Home For Sale $1,285,000

Reduced By $14,000
View Details 50 Photos
On Market For 48 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3160

  • Year Built

    2005

  • $/SqFt

    $407

Located near "The Oaks" and “Stoney Brook” Country Clubs, beautiful beaches, nature trails, and more, this remarkable home seamlessly blends functionality, refinement, and the coveted Florida lifestyle. MLS#A4610275. RE/MAX ALLIANCE GROUP.

Home For Sale $975,000

Reduced By $125,000
View Details 93 Photos
On Market For 47 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2888

  • Year Built

    2002

  • $/SqFt

    $338

Rivendell The Woodlands - This lovely home has a serene Florida feel with its privacy and tropical beauty surrounding you. MLS#A4609658. COLDWELL BANKER REALTY.

Home For Sale $3,100,000

View Details 100 Photos
On Market For 51 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4937

  • Year Built

    1999

  • $/SqFt

    $628

Featuring two championship golf courses, lighted pickleball courts, 12 HAR-TRU tennis courts (5 lighted), a state-of-the-art fitness center, croquet lawn, and a vast array of dining and social options, the Oaks is situated close to the gorgeous local beaches, and all the shopping, cultural and recreational offerings of Downtown Sarasota. MLS#A4609703. COLDWELL BANKER REALTY.

Pended $799,900

View Details 55 Photos
On Market For 20 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2388

  • Year Built

    2002

  • $/SqFt

    $335

The community is conveniently located a short drive from the Legacy Bike Trail, Oscar Scherer State Park, world-famous Siesta Key Beach, Casey Key, Nokomis and Venice Beaches, as well as casual and upscale dining, shopping, and the nationally recognized Pine View School. MLS#A4609741. RE/MAX PLATINUM REALTY.

Home For Sale $1,490,000

View Details 90 Photos
On Market For 53 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3526

  • Year Built

    2001

  • $/SqFt

    $423

A community your will be proud to call home. MLS#A4606078. CARON REALTY INC.

Pended $299,900

Reduced By $20,000
View Details 42 Photos
*POTENTIAL GREAT VALUE
On Market For 54 Days

  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    987

  • Year Built

    1981

  • $/SqFt

    $304

If you have ever dreamed of living in a charming Florida oasis, 319 Patterson is the home for you! MLS#A4609331. DALTON WADE INC.

Home For Sale $2,100,000

View Details 89 Photos
*POTENTIAL GREAT VALUE
On Market For 58 Days

  • Bedrooms

    5

  • Full Bath(s)

    6

  • Sq. Ft.

    4885

  • Year Built

    1990

  • $/SqFt

    $430

Last but not least a wrap-around second floor balcony that sets the stage for pure elegance. Brand New roof installed 2024! ! MLS#A4608902. COLDWELL BANKER REALTY.

Home For Sale $1,339,000

Reduced By $50,000
View Details 62 Photos
On Market For 63 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2844

  • Year Built

    1988

  • $/SqFt

    $471

Social or Golf Membership is required at the Oaks. MLS#A4608440. SOLUTIONS REALTY.

Home For Sale $525,000

Reduced By $25,000
View Details 41 Photos
On Market For 65 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1334

  • Year Built

    1970

  • $/SqFt

    $394

Some of the photos have been virtually staged. Schedule a showing today! MLS#N6132543. PELICAN REALTY CORP.

Pended $810,000

Reduced By $85,000
View Details 68 Photos
*POTENTIAL GREAT VALUE
On Market For 46 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2837

  • Year Built

    1998

  • $/SqFt

    $286

Schedule your viewing today and experience the best of Florida living in South Creek. MLS#A4607404. EXP REALTY LLC.

Home For Sale $2,999,000

Reduced By $401,000
View Details 91 Photos
On Market For 84 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2473

  • Year Built

    1985

  • $/SqFt

    $1,213

Whether you purchase this home for entertainment or relaxation, you need to schedule a viewing. MLS#T3505796. LPT REALTY.

Home For Sale $925,000

Reduced By $40,000
View Details 26 Photos
On Market For 78 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2015

  • Year Built

    1986

  • $/SqFt

    $459

Southbay Yacht & Racquet Club - Southbay offers the active Florida lifestyle you'll love. MLS#A4605059. HORIZON REALTY INTERNATIONAL.

Home For Sale $564,900

Reduced By $74,100
View Details 30 Photos
On Market For 87 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1977

  • Year Built

    1995

  • $/SqFt

    $286

Bay Oaks Estates - With Siesta and Nokomis Beaches nearby, you'll have endless opportunities to soak up the sun, swim in the crystal-clear waters, or simply unwind and take in the breathtaking views. MLS#A4605531. RE/MAX ALLIANCE GROUP.

Home For Sale $450,000

Reduced By $45,000
View Details 55 Photos
On Market For 92 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1304

  • Year Built

    1972

  • $/SqFt

    $345

Great location in proximity to restaurants, shopping, Oscar Scherer State Park, Legacy Trail, Casey Key, Siesta Key, downtown Venice, and the world famous beaches of Florida's Gulf Coast! ! MLS#A4605082. UKEEPCOMMISSION REAL ESTATE.

Home For Sale $1,995,000

View Details 95 Photos
On Market For 94 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3912

  • Year Built

    1989

  • $/SqFt

    $510

Club membership is required with homeownership. MLS#A4603094. COLDWELL BANKER REALTY.

Home For Sale $995,000

View Details 76 Photos
On Market For 97 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    3182

  • Year Built

    1996

  • $/SqFt

    $313

Membership is required, either social or golf, and it's all waiting for you to enjoy the wonderful lifestyle convenient to everything Sarasota has to offer. MLS#A4604256. COLDWELL BANKER SARASOTA CENT..

Home For Sale $3,995,000

View Details 80 Photos
On Market For 97 Days

  • Bedrooms

    4

  • Full Bath(s)

    5

  • Sq. Ft.

    5453

  • Year Built

    1986

  • $/SqFt

    $733

**ENJOY THE 3D VIRTUAL TOUR and AERIAL VIDEO** MLS#A4600730. GENEROUS PROPERTY.

Home For Sale $655,000

Reduced By $15,000
View Details 40 Photos
On Market For 97 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2100

  • Year Built

    2002

  • $/SqFt

    $312

Rivendell The Woodlands - Located minutes from beaches, Oscar Scherer State Park and Legacy Trail. MLS#A4604523. MICHAEL SAUNDERS & COMPANY.

Home For Sale $999,000

Reduced By $101,000
View Details 79 Photos
*POTENTIAL GREAT VALUE
On Market For 101 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    4031

  • Year Built

    1978

  • $/SqFt

    $248

Visit this home now to see its full potential for yourself MLS#A4603906. COLDWELL BANKER REALTY.

Home For Sale $1,689,900

View Details 45 Photos
On Market For 107 Days

  • Bedrooms

    3

  • Full Bath(s)

    4

  • Sq. Ft.

    3905

  • Year Built

    1986

  • $/SqFt

    $433

**ENJOY THE 3D VIRTUAL TOUR and AERIAL VIDEO** MLS#A4601618. GENEROUS PROPERTY.

Pended $795,000

Reduced By $44,000
View Details 29 Photos
On Market For 103 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2326

  • Year Built

    2004

  • $/SqFt

    $342

Rivendell The Woodlands - This home located in the preferred flood zone X. MLS#A4602936. RE/MAX ALLIANCE GROUP.

Pended $799,999

Reduced By $55,001
View Details 69 Photos
On Market For 111 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2695

  • Year Built

    2002

  • $/SqFt

    $297

Rivendell The Woodlands - There is also a heated community pool maintained by the Association.This property is minutes away from the nationally recognized Sarasota County public gifted Pine View School . MLS#A4602604. M H FOGARTY AND COMPANY LLC.

Pended $700,000

Reduced By $75,000
View Details 69 Photos
On Market For 110 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2335

  • Year Built

    1992

  • $/SqFt

    $300

Don’t miss the opportunity to make 17 Bayhead Lane your place to enjoy an amazing Florida lifestyle. MLS#A4602140. MICHAEL SAUNDERS & COMPANY.

Home For Sale $599,000

Reduced By $61,000
View Details 50 Photos
On Market For 106 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2165

  • Year Built

    2004

  • $/SqFt

    $277

Hurricane shutters and a central vacuum system are included. MLS#A4602443. PREMIER SOTHEBYS INTL REALTY.

Pended $1,195,000

Reduced By $100,000
View Details 80 Photos
On Market For 114 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2573

  • Year Built

    1989

  • $/SqFt

    $464

The Oaks Club is a Platinum Club of America, Emerald Club of the World and Elite Distinguished Club of the World, and is minutes to Sarasota’s award winning beaches, downtown’s cultural arts, and shopping. MLS#A4601227. COLDWELL BANKER SARASOTA CENT..

Home For Sale $625,000

Reduced By $14,900
View Details 76 Photos
On Market For 116 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2165

  • Year Built

    2004

  • $/SqFt

    $289

Schedule your private showing today and experience luxury living at its finest! MLS#N6131596. RE/MAX PALM REALTY OF VENICE.

Home For Sale $1,095,000

View Details 64 Photos
On Market For 48 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2855

  • Year Built

    1997

  • $/SqFt

    $384

There is no shortage of shopping and dining options as well. Schedule your showing today! MLS#A4600972. ROSEBAY INTERNATIONAL REALTY INC.

Home For Sale $600,000

Reduced By $99,000
View Details 52 Photos
*POTENTIAL GREAT VALUE
On Market For 122 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2312

  • Year Built

    1997

  • $/SqFt

    $260

Put this one on the top of your list! MLS#A4599768. COLDWELL BANKER REALTY.

Home For Sale $525,000

View Details 63 Photos
On Market For 124 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1604

  • Year Built

    2000

  • $/SqFt

    $327

Community Clubhouse with generous-size pool is a short walk up the street and the beach is only 2 stoplights away! ! MLS#A4600898. FLORIDA HOME TEAM LLC.

Home For Sale $1,099,900

Reduced By $100,000
View Details 36 Photos
On Market For 125 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2932

  • Year Built

    1989

  • $/SqFt

    $375

Schedule your private showing today and make this slice of paradise yours! MLS#N6131393. ENGEL + VOELKERS SARASOTA.

Home For Sale $699,500

Reduced By $29,500
View Details 51 Photos
On Market For 125 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2125

  • Year Built

    2002

  • $/SqFt

    $329

Rivendell The Woodlands - Top-rated Pine View School is a short distance. MLS#A4599840. PREMIER SOTHEBYS INTL REALTY.

Viewing HOMES 1 to 50 of 69

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 727-247-2363 and speak with one of our real estate consultants.

Popular Homes

City
Avg Price
Median Price
Available
Distressed
Reduced
Avg DOM
Anna Maria
$3,724,203
$2,900,000
86
0.0%
53.5%
165

Bradenton
$743,855
$580,000
1437
0.5%
58.7%
84

Bradenton Beach
$4,851,294
$3,950,000
31
0.0%
35.5%
133

Cortez
$1,709,915
$1,500,000
13
0.0%
23.1%
60

Ellenton
$528,731
$478,560
51
0.0%
66.7%
91

Englewood
$821,049
$479,000
418
1.0%
62.4%
109

Holmes Beach
$3,313,545
$2,199,000
97
1.0%
60.8%
140

Lakewood Ranch
$1,187,238
$805,000
309
0.3%
66.0%
97

Longboat Key
$3,803,620
$2,445,000
86
0.0%
58.1%
130

Myakka City
$1,011,565
$794,900
35
0.0%
74.3%
108

Nokomis
$1,096,374
$600,000
309
0.0%
54.4%
103

North Port
$402,581
$379,000
1063
0.8%
59.3%
123

Palmetto
$530,878
$421,990
404
2.2%
55.9%
85

Parrish
$530,358
$457,792
744
0.1%
51.5%
87

Sarasota
$1,492,811
$758,495
1588
0.6%
54.0%
97

Terra Ceia
$1,947,998
$2,124,500
6
0.0%
66.7%
94

Venice
$614,074
$539,600
848
0.7%
61.2%
97

EasyStreet

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