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Osprey Homes For Sale & Osprey FL Real Estate

Home For Sale $959,000

View 21 Bayhead Ln Osprey FL
View Details 92 Photos
View 21 Bayhead Ln Osprey FL
View 21 Bayhead Ln Osprey FL
View 21 Bayhead Ln Osprey FL
On Market For 2 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2216

  • Year Built

    2002

  • $/SqFt

    $433

There are two 18 hole championship golf courses, 12 HarTru tennis courts, 4 pickleball courts, croquet and many social activities. Membership is required. MLS#A4627082. MICHAEL SAUNDERS & COMPANY.

Home For Sale $380,000

View 214 Patterson Ave Osprey FL
View Details 34 Photos
View 214 Patterson Ave Osprey FL
View 214 Patterson Ave Osprey FL
View 214 Patterson Ave Osprey FL
On Market For 7 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1092

  • Year Built

    2004

  • $/SqFt

    $348

Live the Florida oasis lifestyle you’ve always dreamed of! MLS#A4629150. RE/MAX ALLIANCE GROUP.

Home For Sale $950,000

View 186 Turquoise Ln Osprey FL
View Details 90 Photos
View 186 Turquoise Ln Osprey FL
View 186 Turquoise Ln Osprey FL
View 186 Turquoise Ln Osprey FL
On Market For 10 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2294

  • Year Built

    2002

  • $/SqFt

    $414

Add in a celebrated social calendar, and you know you have found the perfect place to live an incredible lifestyle on the gorgeous Gulf Coast. MLS#A4627843. COLDWELL BANKER REALTY.

Home For Sale $550,000

View 555 Meadow Sweet Cir Osprey FL
View Details 3 Photos
View 555 Meadow Sweet Cir Osprey FL
View 555 Meadow Sweet Cir Osprey FL
On Market For 14 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1680

  • Year Built

    1997

  • $/SqFt

    $327

It's all taken care of as well as the large heated swimming pool which is a few footsteps from your back door. It's a real charmer! MLS#TB8319113. JACK KELLER INC.

Home For Sale $4,495,000

View Details 82 Photos
*POTENTIAL GREAT VALUE
On Market For 18 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    9081

  • Year Built

    2003

  • $/SqFt

    $495

Membership is required and there is NO WAITLIST for GOLF or SOCIAL Membership. **ENJOY THE 3D VIRTUAL TOUR** MLS#A4627698. GENEROUS PROPERTY.

Home For Sale $799,000

View Details 50 Photos
On Market For 19 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2767

  • Year Built

    1998

  • $/SqFt

    $289

HOA fee is only $270.00 annually. New roof in 2019! MLS#A4627306. COLDWELL BANKER REALTY.

Pended $1,295,000

View Details 72 Photos
On Market For 19 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2844

  • Year Built

    1988

  • $/SqFt

    $455

Membership is required and there is NO WAITLIST for GOLF or SOCIAL Membership. **ENJOY THE 3D VIRTUAL TOUR** MLS#A4626406. GENEROUS PROPERTY.

Home For Sale $959,000

View Details 56 Photos
On Market For 21 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1402

  • Year Built

    1966

  • $/SqFt

    $684

A community marina offers boat slips for property owners, and the canal was dredged in 2024 for average depth of 4 feet for entire boat basin Newer drainfiield, impact windows, septic pipes relined, re piped above, not much else to do, immaculate, furnished a possibility. MLS#N6135122. KELLER WILLIAMS REALTY GOLD.

Home For Sale $951,000

View Details 100 Photos
*POTENTIAL GREAT VALUE
On Market For 22 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    3183

  • Year Built

    2005

  • $/SqFt

    $299

Don't miss out on this rare opportunity to embrace the essence of coastal living in Osprey. Your dream home awaits! MLS#A4627320. KELLER WILLIAMS ON THE WATER.

Home For Sale $599,000

Reduced By $16,000
View Details 79 Photos
On Market For 25 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1862

  • Year Built

    1990

  • $/SqFt

    $322

The community is less than a mile from the Gulf of Mexico, and is proximate to Blackburn Point Marina, County park with boat launch, shopping, entertainment, dining, the Legacy Trail and the Gulf beaches. MLS#A4626269. COMPASS FLORIDA LLC.

Home For Sale $699,000

View Details 76 Photos
On Market For 26 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2431

  • Year Built

    1995

  • $/SqFt

    $288

(Some Furniture available outside of contract) MLS#A4626386. COLDWELL BANKER REALTY.

Home For Sale $1,690,000

View Details 54 Photos
On Market For 28 Days

  • Bedrooms

    3

  • Full Bath(s)

    4

  • Sq. Ft.

    3905

  • Year Built

    1986

  • $/SqFt

    $433

**ENJOY THE 3D VIRTUAL TOUR and AERIAL VIDEO** MLS#A4626405. GENEROUS PROPERTY.

Home For Sale $1,850,000

View Details 100 Photos
On Market For 31 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    3118

  • Year Built

    2016

  • $/SqFt

    $593

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 for social events, The Oaks is truly Sarasota’s premier golf and country club. MLS#A4623628. COLDWELL BANKER REALTY.

Home For Sale $625,000

Reduced By $25,000
View Details 64 Photos
*POTENTIAL GREAT VALUE
On Market For 48 Days

  • Bedrooms

    2

  • Full Bath(s)

    3

  • Sq. Ft.

    2837

  • Year Built

    1992

  • $/SqFt

    $220

Don’t let this one get away. MLS#A4625066. KELLER WILLIAMS ON THE WATER S.

Home For Sale $559,000

View Details 52 Photos
On Market For 49 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1850

  • Year Built

    2005

  • $/SqFt

    $302

Willowbend - Located in a preferred X flood zone and no CDD fees. MLS#A4625047. PREMIER SOTHEBYS INTL REALTY.

Pended $774,900

View Details 55 Photos
On Market For 49 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2328

  • Year Built

    2005

  • $/SqFt

    $333

Located in a preferred X flood zone without a CDD fee. MLS#A4625125. PREMIER SOTHEBYS INTL REALTY.

Home For Sale $925,000

View Details 100 Photos
On Market For 56 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    2310

  • Year Built

    2001

  • $/SqFt

    $400

A Golf equity or Social membership is required with a real estate purchase. MLS#A4624476. MICHAEL SAUNDERS & COMPANY.

Home For Sale $699,000

Reduced By $30,000
View Details 56 Photos
On Market For 62 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2658

  • Year Built

    2002

  • $/SqFt

    $263

Being centrally located, enjoy all the amenities Sarasota and Venice have, including arts, entertainment, championship golf, restaurants and shopping. MLS#A4624141. FLORIDA HOME TEAM LLC.

Pended $794,000

View Details 57 Photos
On Market For 37 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2441

  • Year Built

    2003

  • $/SqFt

    $325

Rivendell The Woodlands - If you envision paradise, this property presents an intriguing opportunity. MLS#N6134417. PREMIER SOTHEBYS INTL REALTY.

Pended $745,000

View Details 93 Photos
On Market For 53 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2369

  • Year Built

    1990

  • $/SqFt

    $314

Schedule your private showing today and fall in love with the lifestyle that 356 South Creek Drive has to offer. MLS#A4623302. MICHAEL SAUNDERS & COMPANY.

Home For Sale $1,795,000

View Details 62 Photos
On Market For 69 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    4241

  • Year Built

    1991

  • $/SqFt

    $423

**ENJOY THE 3D VIRTUAL TOUR and AERIAL VIDEO** MLS#A4621683. GENEROUS PROPERTY.

Home For Sale $550,000

Reduced By $25,000
View Details 39 Photos
On Market For 72 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2116

  • Year Built

    1995

  • $/SqFt

    $260

Schedule your private showing today and enjoy Florida living at its finest! MLS#A4620117. RE/MAX ALLIANCE GROUP.

Home For Sale $449,900

View Details 53 Photos
On Market For 76 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1648

  • Year Built

    1995

  • $/SqFt

    $273

Make this fabulous property your new home! You will love living here! MLS#A4622317. COLDWELL BANKER SARASOTA CENT..

Home For Sale $3,995,000

Reduced By $255,000
View Details 93 Photos
On Market For 77 Days

  • Bedrooms

    4

  • Full Bath(s)

    5

  • Sq. Ft.

    4535

  • Year Built

    1975

  • $/SqFt

    $881



This one-of-a-kind property offers luxury, privacy, and the ultimate Florida lifestyle—don’t miss the opportunity to make it yours! MLS#N6134456. CORNERSTONE R.E OF SW FL.

Pended $519,999

Reduced By $57,721
View Details 55 Photos
*POTENTIAL GREAT VALUE
On Market For 77 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2222

  • Year Built

    1994

  • $/SqFt

    $234

Bay Oaks Estates - We can't wait to accept your offer :-) MLS#N6134458. KELLER WILLIAMS ISLAND LIFE REAL ESTATE.

Pended $2,599,000

View Details 96 Photos
On Market For 79 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    5153

  • Year Built

    1999

  • $/SqFt

    $504

Oaks - Note: The Oaks Club Membership Is Required - Please Refer To Club Documents For Details. MLS#A4621942. RE/MAX ALLIANCE GROUP.

Home For Sale $325,000

View Details 31 Photos
On Market For 85 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1120

  • Year Built

    1957

  • $/SqFt

    $290

Call today for more information and to discuss setback details! MLS#A4621675. KELLER WILLIAMS REALTY SELECT.

Home For Sale $1,100,000

View Details 60 Photos
On Market For 90 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3011

  • Year Built

    2001

  • $/SqFt

    $365

Close to everything, beaches, restaurants, downtown Sarasota as well as downtown Venice, the Legacy Trail, Oscar Sherer State Park and so much more. MLS#A4620960. MICHAEL SAUNDERS & COMPANY.

Home For Sale $1,099,000

Reduced By $176,000
View Details 89 Photos
On Market For 91 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    3093

  • Year Built

    1977

  • $/SqFt

    $355

Make sure to see the attached video (make sure to turn the volume on) of the community Southbay Yacht & Raquet Club where this lovely home is located. MLS#A4620572. WATERSIDE REALTY LLC.

Home For Sale $888,000

Reduced By $42,000
View Details 76 Photos
On Market For 91 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2837

  • Year Built

    1998

  • $/SqFt

    $313

Don't miss out on this Awesome home - Schedule your viewing today! MLS#A4619602. COASTAL LUXURY PARTNERS, INC..

Home For Sale $2,295,000

View Details 63 Photos
On Market For 100 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3896

  • Year Built

    1989

  • $/SqFt

    $589

Membership is required and there is NO WAITLIST for GOLF or SOCIAL Membership. **ENJOY THE 3D VIRTUAL TOUR** MLS#A4619185. GENEROUS PROPERTY.

Pended $865,000

Reduced By $34,000
View Details 55 Photos
On Market For 106 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2408

  • Year Built

    2004

  • $/SqFt

    $359

Rivendell The Woodlands - The Legacy Trail, a scenic route for biking and walking, is practically at your doorstep, as is Pine View School, and Albee Road provides quick access to Nokomis Beach on the Gulf of Mexico. MLS#T3545413. REDFIN CORPORATION.

Home For Sale $2,950,000

Reduced By $250,000
View Details 37 Photos
On Market For 119 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2862

  • Year Built

    1979

  • $/SqFt

    $1,031

Sorrento Shores - This unique waterfront estate embodies the best of Florida living and offers a rare opportunity to own a slice of paradise on the bay. MLS#A4617786. EXP REALTY LLC.

Home For Sale $1,595,000

View Details 57 Photos
On Market For 120 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2913

  • Year Built

    2023

  • $/SqFt

    $548

One or more photo(s) has been virtually staged. **ENJOY THE 3D VIRTUAL TOUR** MLS#A4617671. GENEROUS PROPERTY.

Home For Sale $1,075,000

Reduced By $100,000
View Details 35 Photos
On Market For 120 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2112

  • Year Built

    1975

  • $/SqFt

    $509

This is the waterfront opportunity you have been waiting for... MLS#A4616602. COLDWELL BANKER SARASOTA CENT..

Home For Sale $649,900

Reduced By $79,100
View Details 72 Photos
On Market For 126 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2340

  • Year Built

    2005

  • $/SqFt

    $278

Centrally located in Osprey within a short distance to beaches, restaurants & shopping. MLS#A4617437. COLDWELL BANKER SARASOTA CENT..

Home For Sale $1,500,000

View Details 36 Photos
On Market For 127 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3541

  • Year Built

    1997

  • $/SqFt

    $424

Bring your clothes & live happily in this incredibly comforting home. Cheers & welcome home! MLS#G5084149. ILLUSTRATED PROPERTIES LLC (CO.

Home For Sale $449,900

View Details 19 Photos
*POTENTIAL GREAT VALUE
On Market For 127 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1758

  • Year Built

    1962

  • $/SqFt

    $256

This is a great opportunity to own a home in one of the most popular “west of the Trail” communities in the Sarasota area. Schedule your private tour today. MLS#A4617457. RE/MAX ALLIANCE GROUP.

Home For Sale $429,900

Reduced By $20,000
View Details 43 Photos
On Market For 102 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1346

  • Year Built

    1963

  • $/SqFt

    $319

Bay Acres - Electric bill for a full year 2023 was $636.28 MLS#A4617047. HORIZON REALTY INTERNATIONAL.

Home For Sale $1,725,000

Reduced By $75,000
View Details 100 Photos
On Market For 147 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4614

  • Year Built

    2003

  • $/SqFt

    $374

Initiation Fees Going Up On 2/1/2025. Buy Now Before The Increase! MLS#A4615296. COLDWELL BANKER REALTY.

Home For Sale $797,900

Reduced By $27,100
View Details 63 Photos
On Market For 147 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2314

  • Year Built

    2003

  • $/SqFt

    $345

While a short distance from the Intracoastal and Gulf of Mexico, this home is in a preferred X flood zone. MLS#A4615081. PREMIER SOTHEBYS INTL REALTY.

Home For Sale $1,875,000

Reduced By $20,000
View Details 58 Photos
On Market For 159 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3464

  • Year Built

    2014

  • $/SqFt

    $541

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 $550,000

Reduced By $50,000
View Details 39 Photos
On Market For 160 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1867

  • Year Built

    1996

  • $/SqFt

    $295

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 $885,000

Reduced By $65,000
View Details 47 Photos
On Market For 162 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2513

  • Year Built

    1987

  • $/SqFt

    $352

Southbay Yacht & Racquet Club - (Note: One or more photos have been virtually staged.) MLS#A4612015. COLDWELL BANKER SARASOTA CENT..

Pended $995,000

Reduced By $175,000
View Details 31 Photos
On Market For 124 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2928

  • Year Built

    2002

  • $/SqFt

    $340

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 $1,395,000

Reduced By $154,000
View Details 100 Photos
On Market For 178 Days

  • Bedrooms

    4

  • Full Bath(s)

    5

  • Sq. Ft.

    3906

  • Year Built

    1989

  • $/SqFt

    $357

The Oaks has two 18-hole championship golf courses, 12 HAR-TRU tennis courts maintained to tournament standards, 5 of which are lighted, bocce and lighted pickleball courts, a club pool, and a wide variety of dining. NEW ROOF 2022. MLS#A4610414. COLDWELL BANKER REALTY.

Home For Sale $5,500,000

Reduced By $1,000,000
View Details 38 Photos
*POTENTIAL GREAT VALUE
On Market For 193 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    3086

  • Year Built

    1916

  • $/SqFt

    $1,782

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 $1,800,000

Reduced By $300,000
View Details 89 Photos
*POTENTIAL GREAT VALUE
On Market For 205 Days

  • Bedrooms

    5

  • Full Bath(s)

    6

  • Sq. Ft.

    4885

  • Year Built

    1990

  • $/SqFt

    $368

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 $995,000

View Details 76 Photos
On Market For 244 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. MICHAEL SAUNDERS & COMPANY.

Pended $3,995,000

View Details 81 Photos
On Market For 244 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.

Viewing HOMES 1 to 50 of 61

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
$4,553,304
$3,472,500
28
0.0%
35.7%
154

Bradenton
$738,895
$582,640
1285
0.6%
52.2%
94

Bradenton Beach
$4,048,635
$3,295,000
13
0.0%
61.5%
222

Cortez
$1,758,100
$1,519,500
10
0.0%
30.0%
76

Ellenton
$549,759
$535,000
29
0.0%
48.3%
104

Englewood
$566,905
$439,450
388
0.8%
48.5%
97

Holmes Beach
$3,350,800
$2,295,000
35
0.0%
40.0%
141

Lakewood Ranch
$1,131,622
$828,132
268
0.4%
56.0%
97

Longboat Key
$5,415,111
$3,447,500
54
1.9%
29.6%
130

Myakka City
$1,022,703
$775,000
34
0.0%
55.9%
126

Nokomis
$821,806
$599,000
288
0.7%
55.2%
107

North Port
$392,329
$365,000
1019
1.1%
51.2%
121

Palmetto
$479,582
$410,495
382
0.8%
58.1%
85

Parrish
$507,307
$437,500
833
0.6%
62.1%
92

Sarasota
$1,319,841
$690,000
1446
0.6%
46.2%
99

Terra Ceia
$1,598,980
$1,999,999
5
0.0%
20.0%
75

Venice
$584,562
$521,755
766
0.3%
50.1%
98

EasyStreet

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